Silicone-polyether copolymers, sealants comprising silicone-polyether copolymers, and related methods

Abstract

A composition comprising at least one silicone-polyether copolymer having an average formula X g [Z j Y o ] c wherein each X is an independently selected silicone moiety having a particular structure, each Y is an independently selected polyether moiety, each Z is an independently selected organosilicon moiety, subscript c is 1 to 150, subscript g > 1, subscript j is independently 0 or 1, and subscript o is independently 0 or 1, with the proviso that 1 < j + o < 2 in each moiety indicated by subscript c, and there is at least one moiety indicated by subscript c where subscript o is 1. Also disclosed are methods of making the composition and sealants formed therefrom.

Description

[0001] Cross Reference to Related Applications

[0002] This application claims priority to and all advantages of U.S. Provisional Patent Application No. 63 / 338,198, filed May 4, 2022, the contents of which are incorporated herein by reference. TECHNICAL FIELD

[0003] The present invention relates generally to compositions and copolymers, and more particularly to compositions comprising at least one silicone-polyether copolymer, methods of making silicone-polyether copolymers, and sealants comprising silicone-polyether copolymers. BACKGROUND

[0004] Sealants are known in the art and are used in countless end-use applications and environments. The physical and performance properties of sealants, as well as the particular curing mechanisms associated therewith, are generally selected based on the particular end-use application and environment in which the sealant is used. Sealants can be based on a variety of different chemistries and curing mechanisms. For example, sealants can be silicone-based and comprise organopolysiloxanes. Alternatively, sealants can be organic and comprise organic components, such as to form urethanes. Hybrid materials are increasingly used in sealants, which can combine the benefits traditionally associated with silicone-based sealants and organic sealants.

[0005] For example, silane-modified polyethers are increasingly used in sealants as hybrid materials. However, existing silane-modified polyethers have limitations. For example, sealants including conventional silane-modified polyethers have undesirable cure speeds, or cure speeds that cannot be selectively controlled or adjusted based on desired properties. Additionally, maximizing the cure speed of conventional sealants can require high concentrations of catalyst, or otherwise affect the performance properties of the resulting cured product. Thus, it is difficult or impossible to simultaneously optimize cure speed and performance properties. SUMMARY

[0006] A composition comprising at least one silicone-polyether copolymer having an average formula X g [Z j Y o ] c Each X is independently a silicone moiety having one of formula (I) or formula (II):

[0007] (R 1 ) a (R 2 O) 3-a Si-D-SiR 1 2-O-SiR 1 2-D 1 -(I)

[0008] (R 1 ) a (R 2 O) 3-a Si-D 1 -(II)

[0009] wherein each Y is an independently selected polyether moiety, each Z is an independently selected silicone moiety, each R 1 is an independently selected substituted or unsubstituted hydrocarbyl group having from 1 to 18 carbon atoms; each R 2 is an independently selected alkyl group having from 1 to 8 carbon atoms; each D is independently a divalent hydrocarbon group having from 2 to 18 carbon atoms; each D 1 is independently a divalent hydrocarbon group having from 2 to 18 carbon atoms; each subscript a is independently 0 or 1; subscript c is from 1 to 150; subscript g > 1; each subscript j is independently 0 or 1; each subscript o is independently 0 or 1, provided that 1 < j + o < 2 in each moiety indicated by subscript c and there is at least one moiety indicated by subscript c where subscript o is 1. The composition meets at least one of the following conditions: (i) the silicone-polyether copolymer includes at least one silicone moiety X of formula (I) and at least one silicone moiety X of formula (II); and / or (ii) the composition comprises at least one silicone-polyether copolymer (A) where each silicone moiety X has formula (I) and at least one silicone-polyether copolymer (B) where each silicone moiety X has formula (II).

[0010] A method of making a silicone-polyether copolymer is disclosed. The method includes reacting a polyether compound having on average more than one terminal unsaturated group, optionally a chain extending organosilicon compound, a first endblocking organosilicon compound, and a second endblocking organosilicon compound different from the first endblocking organosilicon compound in the presence of a hydrosilylation catalyst to make a composition comprising the at least one silicone-polyether copolymer.

[0011] A sealant is also disclosed. The sealant includes a composition comprising at least one silicone-polyether copolymer and a condensation reaction catalyst.

[0012] A cured product is additionally disclosed. The cured product is formed from the sealant. Further, a composite article and a method of making the composite article are disclosed. The composite article includes a substrate and the cured product disposed on the substrate. The method includes disposing the sealant on the substrate and curing the sealant to produce the cured product on the substrate to make the composite article. BRIEF DESCRIPTION OF DRAWINGS

[0013] Various advantages and aspects of the present disclosure can be understood with reference to the following detailed description when considered in connection with the appended drawings, in which:

[0014] Figure 1 Tack free times (TFT) are shown for sealants from certain embodiments of the present disclosure. DETAILED DESCRIPTION

[0015] A composition comprising at least one silicone-polyether copolymer having an average formula X g [ Z j Y o ] c . Each X is independently a silicone moiety having one of formula (I) or formula (II):

[0016] (R 1 ) a (R 2 O) 3-a Si-D-SiR 1 2-O-SiR 1 2-D 1 -(I)

[0017] (R 1 ) a (R 2 O) 3-a Si-D 1 -(II)

[0018] wherein each Y is an independently selected polyether moiety, and each Z is an independently selected organosilicon moiety, wherein each R 1 is an independently selected substituted or unsubstituted hydrocarbyl group having from 1 to 18 carbon atoms; each R 2 is an independently selected alkyl group having from 1 to 8 carbon atoms; each D is independently a divalent hydrocarbon group having from 2 to 18 carbon atoms; each D 1independently a divalent hydrocarbon group having 2 to 18 carbon atoms; each subscript a is independently 0 or 1 ; subscript c is 1 to 150; subscript g > 1 ; each subscript j is 0 or 1 ; each subscript o is independently 0 or 1, provided that 1 < j + o < 2 in each moiety indicated by subscript c and there is at least one moiety indicated by subscript c where subscript o is 1. The composition meets at least one of the following conditions: (i) the silicone-polyether copolymer includes at least one silicone moiety X of formula (I) and at least one silicone moiety X of formula (II); and / or (ii) the composition comprises at least one silicone-polyether copolymer (A) where each silicone moiety X has formula (I) and at least one silicone-polyether copolymer (B) where each silicone moiety X has formula (II). In one embodiment, the composition can comprise at least one silicone-polyether copolymer where each silicone moiety X has formula (II), but where subscript a is different in each silicone moiety X of formula (II).

[0019] each R 1 are independently selected and can be linear, branched, cyclic, or a combination thereof. Cyclic hydrocarbyl groups include aryl groups as well as saturated or non-conjugated cyclic groups. Cyclic hydrocarbyl groups can be monocyclic or polycyclic. Linear and branched hydrocarbyl groups can independently be saturated or unsaturated. One example of a combination of linear and cyclic hydrocarbyl groups is aralkyl groups. By "substituted" it is meant that one or more hydrogen atoms can be replaced by atoms other than hydrogen (e.g., halogen atoms such as chlorine, fluorine, bromine, etc.), or R 1 carbon atoms within the chain can be replaced by atoms other than carbon, i.e., R 1One or more heteroatoms, such as oxygen, sulfur, nitrogen, and the like, can be included in the chain. Suitable alkyl groups are exemplified by, but not limited to, the following: methyl, ethyl, propyl (e.g., iso-propyl and / or n-propyl), butyl (e.g., iso-butyl, n-butyl, t-butyl, and / or sec-butyl), pentyl (e.g., iso-pentyl, neopentyl, and / or t-pentyl), hexyl, and branched saturated hydrocarbon groups having 6 carbon atoms. Examples of suitable aryl groups have, but are not limited to, the following: phenyl, tolyl, xylyl, naphthyl, benzyl, and dimethylphenyl. Suitable alkenyl groups include ethenyl, allyl, propenyl, isopropenyl, butenyl, isobutenyl, pentenyl, heptenyl, hexenyl, and cyclohexenyl groups. Suitable monovalent halogenated hydrocarbon groups include, but are not limited to, halogenated alkyl groups of 1 to 6 carbon atoms, or halogenated aryl groups of 6 to 10 carbon atoms. Examples of suitable halogenated alkyl groups have, but are not limited to, the above alkyl groups in which one or more hydrogen atoms are replaced by a halogen atom such as F or Cl. For example, fluoromethyl, 2-fluoropropyl, 3,3,3-trifluoropropyl, 4,4,4-trifluorobutyl, 4,4,4,3,3-pentafluorobutyl, 5,5,5,4,4,3,3-heptafluoropentyl, 6,6,6,5,5,4,4,3,3-nonafluorohexyl, and 8,8,8,7,7-pentafluorooctyl, 2,2-difluorocyclopropyl, 2,3-difluorocyclobutyl, 3,4-difluorocyclohexyl, and 3,4-difluoro-5-methylcycloheptyl, chloromethyl, chloropropyl, 2-dichlorocyclopropyl, and 2,3-dichlorocyclopentyl are examples of suitable halogenated alkyl groups. Examples of suitable halogenated aryl groups have, but are not limited to, the above aryl groups in which one or more hydrogen atoms are replaced by a halogen atom such as F or Cl. For example, chlorobenzyl and fluorobenzyl are suitable halogenated aryl groups.

[0020] In certain embodiments, each R 1 is an independently selected alkyl group. In particular embodiments, each R 1 is a methyl group.

[0021] each R 2 is an independently selected alkyl group having 1 to 8, alternatively 1 to 6, alternatively 1 to 4, alternatively 1 or 2, alternatively 1 carbon atom.

[0022] With respect to the silicone-polyether copolymer, it is understood that the subformula [Z j Y o ] cIt is not intended to imply a linear structure of the silicone-polyether copolymer moieties represented by ZY. Rather, as is understood in the art, the silicone-polyether copolymer ZY can be linear or branched, with each moiety indicated by subscript c being independently selected. Thus, the silicone-polyether copolymer comprises c copolymer moieties ZY, each comprising o polyether moieties Y and j silicone moieties Z. Additionally, it will be appreciated in view of the description below that each polyether moiety Y and silicone moiety Z is independently selected, both within and between each moiety indicated by subscript c, and can each be linear or branched as well.

[0023] each subscript c is from 1 to 150, such as from 1 to 100, alternatively from 1 to 50, alternatively from 1 to 25, alternatively from 1 to 10, and alternatively from 1 to 5. Subscript g is greater than 1, such as from 1.1 to 10, alternatively from 1.1 to 8, alternatively from 1.1 to 6, alternatively from 1.1 to 4, alternatively from 1.1 to 3, alternatively from 1.1 to 2, alternatively from 1.1 to 1.9, alternatively from 1.2 to 1.8, alternatively from 1.2 to 1.7, alternatively from 1.3 to 1.7, alternatively from 1.4 to 1.7, alternatively about 1.4, 1.5, 1.6, or 1.7. Each subscript j is independently 0 or 1, and each subscript o is independently 0 or 1, with the proviso that 1 < j + o < 2 in each moiety indicated by subscript c and that there is at least one moiety indicated by subscript c in which subscript o is 1. Thus, the silicone-polyether copolymer includes at least one polyether moiety Y, but the silicone moiety Z is optional. Because each subscript j and each subscript o are independently selected, there can be moieties indicated by subscript c in which the polyether moiety Y is present but the silicone moiety Z is not present, moieties indicated by subscript c in which the polyether moiety Y is not present but the silicone moiety Z is present, etc. in the silicone-polyether copolymer. In certain embodiments, subscript j is 0. In other embodiments, subscript j is 1. In these or other embodiments, subscript j can be 0 when the silicone-polyether copolymer is branched, whereas subscript j can be 1 when the silicone-polyether copolymer is linear. In certain embodiments, subscript o is 0. In other embodiments, subscript o is 1. Subscripts j and o can be considered to be mole fractions, for example, where when j = 1 and o = 1, there is a 0.5:0.5 mole ratio of silicone moiety Z to polyether moiety Y in the moiety indicated by subscript c. Of course, the mole ratio of Z to Y in each moiety indicated by subscript c is not limited and applies only when both the silicone moiety Z and the polyether moiety Y are present in each moiety indicated by subscript c. For example, when Z is present, the mole ratio of Z:Y in each moiety indicated by subscript c can independently be from about 1000:1 to about 1:1000, alternatively from about 100:1 to about 1:100, alternatively from about 10:1 to about 1:10, alternatively from about 5:1 to about 1:5, alternatively from about 2:1 to about 1:2. As noted above, the subformula [Z j Y o ] c The linear structure of the silicone-polyether copolymer moiety indicated by ZY is not intended to be implied. Likewise, the subformula does not require a particular structure for either of the silicone-polyether copolymer moieties ZY. Rather, depending on the values selected for subscripts j and o, the subformula [Z j Y o ] cThe silicone-polyether copolymer portion represented can include silicone moieties Z and polyether moieties Y in block form (e.g., Y, Z-Y, Y-Z, Y-Z-Y, Z-Y-Z-Y, YY-ZZ, ZZ-YY, etc.) or random form. In particular embodiments, the silicone-polyether copolymer includes polyether moieties Y and silicone moieties Z in a ratio of 2: 1. In specific embodiments, when subscript j is 1, the silicone-polyether copolymer includes one more polyether moieties Y than silicone moieties X in total. In some such embodiments, the polyether moieties Y and silicone moieties Z are present in block form in the silicone-polyether copolymer, such that the silicone-polyether copolymer has an average formula X g Y[ZY] c wherein subscripts c and g are as defined above. In some of these embodiments, the silicone-polyether copolymer includes linear polyether moieties Y and linear silicone moieties Z, and is terminated by silicone moieties X, such that the silicone-polyether copolymer has an average formula X g’ Y[ZY] c X g” wherein c is as defined above, and each of g' and g" is > 0, with the proviso that g' + g" > 1.

[0024] With respect to each X in general, each subscript a is independently 0 or 1. Typically, subscript a is 0. In some embodiments, each subscript a is 0. In certain embodiments, the silicone-polyether copolymer includes at least one X in which subscript a is 1.

[0025] Each D is an independently selected divalent hydrocarbon group having 2 to 18 carbon atoms, alternatively 2 to 16 carbon atoms, alternatively 2 to 14 carbon atoms, alternatively 2 to 12 carbon atoms, alternatively 2 to 10 carbon atoms, alternatively 2 to 8 carbon atoms, alternatively 2 to 6 carbon atoms, alternatively 2 to 4 carbon atoms, alternatively 2 or 3 carbon atoms, alternatively 2 carbon atoms. Each D can independently be linear or branched. For example, when D has two carbon atoms, D has the formula C2H4, and can be linear (CH2CH2) or branched (CHCH3). In certain embodiments, D is linear. When preparing compositions including silicone-polyether copolymers in bulk, in certain embodiments, at least 90 mol%, alternatively at least 95 mol%, alternatively at least 98 mol%, alternatively 100 mol% of D is linear. In specific embodiments, each D is C2H4.

[0026] Each D 1also independently selected, the divalent hydrocarbon group having from 2 to 18 carbon atoms, alternatively from 2 to 16 carbon atoms, alternatively from 2 to 14 carbon atoms, alternatively from 2 to 12 carbon atoms, alternatively from 2 to 10 carbon atoms, alternatively from 2 to 8 carbon atoms, alternatively from 2 to 6 carbon atoms, alternatively from 2 to 4 carbon atoms, alternatively 2 or 3 carbon atoms, alternatively 2 carbon atoms. Each D 1 may be independently linear or branched. For example, when D 1 has two carbon atoms, D 1 has the formula C2H4, and can be linear (CH2CH2) or branched (CHCH3). In certain embodiments, D is linear. When preparing a composition comprising at least one silicone-polyether copolymer, each D 1 are typically formed via a hydrosilylation reaction, and thus are functional groups that are bonded to silicon using an alkenyl group in a hydrosilylation reaction.

[0027] Each Y is a polyether moiety. Each Y is independently selected, and can be any polyether moiety comprising at least one ether moiety, alternatively at least two ether moieties. Each Y can be the same as any or each other Y. Alternatively, the silicone-polyether copolymer can include at least two Ys that are different from each other. Y can be linear or branched. Y can be divalent, trivalent, tetravalent, or have a valence greater than 4. In the context of polyether moiety Y, valence refers to the number of Y-X bonds present in the silicone-polyether copolymer. In certain embodiments, the polyether moiety Y is divalent, such that the silicone-polyether copolymer has the formula X-Y-X. In other embodiments, the valence of the polyether moiety can be greater than 2, in which case the polyether moiety Y is typically branched.

[0028] Each Y typically comprises a polyether moiety having the general formula -O-(C n H 2n O) wpolyethers of the general formula -O-(C2H4O)n- wherein subscript n is independently selected from 2 to 4 in each moiety indicated by subscript w; and wherein subscript w is 1 to 1000. In certain embodiments, Y comprises a plurality of polyethers of this general formula, which can be present in linear or branched form with other polyethers to form a polyether moiety comprising a plurality of oxyalkylene-based polyethers. In such embodiments, Y can comprise oxyethylene units (C2H4O), oxypropylene units (C3H6O), oxybutylene or oxytetramethylene units (C4H8O), or mixtures thereof, which can be in block form or random in Y. The oxyethylene units in Y can independently be linear or branched. For example, the oxyethylene units, if present, can have the formula -CH2CH2O- or have the formula -CHCH3O-. Similarly, the oxypropylene units can have the formula -CH2CH2CH2O-, -CH2CHCH3O-, or -CHCH3CH2O-.

[0029] For example, Y can comprise a polyether having the general formula -O-(C2H4O) x (C3H6O) y (C4H8O) z polyethers of the general formula -O-(C2H4O)n- wherein subscript n is independently selected from 2 to 4 in each moiety indicated by subscript w; and wherein subscript w is 1 to 1000. In certain embodiments, Y comprises a plurality of polyethers of this general formula, which can be present in linear or branched form with other polyethers to form a polyether moiety comprising a plurality of oxyalkylene-based polyethers. In such embodiments, Y can comprise oxyethylene units (C2H4O), oxypropylene units (C3H6O), oxybutylene or oxytetramethylene units (C4H8O), or mixtures thereof, which can be in block form or random in Y. The oxyethylene units in Y can independently be linear or branched. For example, the oxyethylene units, if present, can have the formula -CH2CH2O- or have the formula -CHCH3O-. Similarly, the oxypropylene units can have the formula -CH2CH2CH2O-, -CH2CHCH3O-, or -CHCH3CH2O-. y –, wherein y is as defined above.

[0030] In some embodiments, Y has the formula -D 2 -O-(C n H 2n O) w -D 2 –. In such embodiments, each D 2 is an independently selected divalent hydrocarbon group having 1 to 6 carbon atoms, alternatively 1 to 5 carbon atoms, alternatively 1 to 4 carbon atoms, alternatively 1 or 2 carbon atoms. Each D 2 may independently be linear or branched. For example, when D 2 has two carbon atoms, D 2 has the formula C2H4, and can be linear (CH2CH2) or branched (CHCH3). In certain embodiments, D 2 is linear. Any D 2 may be the same or different than any particular D 1 . In specific embodiments, each D 2 is CH2. In each moiety indicated by subscript w, each subscript n is independently selected from 2 to 4, and subscript w is as defined above.

[0031] For example, in such embodiments, Y can have the formula -D 2 -O-(C2H4O) x (C3H6O) y (C4H8O) z -D 2 where subscript x is 0 to 999; subscript y is 1 to 1000; and subscript z is 0 to 999; and where the units indicated by subscripts x, y, and z can be random or blocky in Y. In certain embodiments, x and z are each 0, such that Y has the formula -D 2 -O-(C3H6O) y -D 2 where D 2 and y are as defined above. In specific embodiments, each D 2 is also C3H6. When x and z are each 0 and each D 2 is C3H6, Y has the formula -C3H6-O-(C3H6O) y -C3H6-, where y is as defined above.

[0032] In certain embodiments, Y has the general formula:

[0033] -CH2-CH(R 3 )-[D 2 ] m -O-[C2H4O] x [C3H6O] y [C4H8O] z -[D 2 ] m -CH(R 3 )-CH2-, where each R 3 is independently a hydrocarbyl group, an alkoxy group, a silyl group, or H having 1 to 6 carbon atoms; each D 2 is an independently selected divalent group having 1 to 6 carbon atoms, subscript m is 0 or 1, subscript x is 0 to 999, subscript y is 1 to 1000, and subscript z is 0 to 999, and where the units indicated by subscripts x, y, and z can be random or blocky in the polyether moiety Y.

[0034] each R 3 is independently selected and can be any of the C1-C6 hydrocarbyl groups described herein. Thus, any R 3 may be the same as or different from any particular R 1 and / or R 2 . For example, R 3 may be methyl, propyl, and the like. In certain embodiments, each R3 is methyl. Alternatively or additionally, R 3 may be H, an alkoxy group, or a silyl group.

[0035] each subscript m is independently 0 or 1, such that Y can contain 0, 1, or 2 divalent hydrocarbon groups D 2 . Typically, each subscript m is 1. However, in certain embodiments, at least one subscript m is 0.

[0036] In some embodiments, Y is branched, as described above. In such embodiments, Y can have the general formula [D 2 ] m’ [P], where D 2 is as defined above, subscript m' > 3 (e.g., 3, 4, 5, 6, 7, 8, 9, 10, etc.), and P is a polyether comprising at least one of the polyethers described above. For example, in some such embodiments, P is a polyether formed from a polyol (e.g., butanediol, glycerol, sorbitol, etc.) and a polyoxyalkylene (e.g., polyoxypropylene) that is capped with m' D 2 moieties. In such cases, the number of alcohol functions making up the polyol will correspond to the maximum number of m'. However, if not all polyoxyalkylene chains extending from the polyol are capped, m' will be less than the number of alcohol functions making up the polyol.

[0037] The number average molecular weight (M n ) of each Y is typically at least about 100. In certain embodiments, at least one Y has a M n of at least 200, alternatively at least 300, alternatively at least 400, alternatively at least 500, alternatively at least 600, alternatively at least 700. In these or other embodiments, each Y has a M n of at least 200, alternatively at least 300, alternatively at least 400, alternatively at least 500, alternatively at least 600, alternatively at least 700, alternatively at least 1,000, alternatively at least 2,000, alternatively at least 4,000, alternatively at least 8,000, alternatively at least 12,000, alternatively at least 16,000, alternatively at least 25,000, alternatively at least 50,000. Typically, each Y is selected based on the presence or absence of Z. For example, when Z is present, the M n of Y can be less than the case when Z is absent. Z can act as a chain extension moiety in the silicone-polyether copolymer, thus allowing for polymerization and chain extension independent of the M n of each Y. The molar ratio of Z to Y can be selected by one of skill in the art based on desired performance properties and synthetic techniques. Number average molecular weight can be readily determined using gel permeation chromatography (GPC) techniques based on polystyrene standards.

[0038] Each Z is an independently selected organosilicon moiety. Each organosilicon moiety Z can independently comprise a linear organosilicon moiety, a branched organosilicon moiety, or both. Likewise, any particular organosilicon moiety Z can itself comprise linear segments or branched segments, or both linear segments and branched segments. Thus, Z can be a linear organosilicon moiety, a branched organosilicon moiety, or an organosilicon moiety comprising at least one linear segment and at least one branched segment. In certain embodiments, Z is branched (i.e., includes at least one branched segment).

[0039] In certain embodiments, each polyether moiety Y is linear, such that the silicone-polyether copolymer can have one of the following structures (when Z is present):

[0040]

[0041] where each X, Y, Z, and subscript c are as defined above. Alternatively, each polyether moiety Y can be branched. For example, the silicone-polyether copolymer can have one of the following structures (when Z is present):

[0042]

[0043] where each X, Y, Z, and subscript c are as defined above. As shown in these structures, each organosilicon moiety Z can be linear or branched. In particular embodiments, both the polyether moiety Y and the organosilicon moiety Z can be branched, such that the silicone-polyether copolymer can have one of the following structures:

[0044]

[0045] where each X, Y, Z, and subscript c are as defined above.

[0046] In one embodiment, each organosilicon moiety Z independently has the following formula:

[0047]

[0048] where each R 1 is independently selected and as defined above, and each d in each organosilicon moiety Z is independently 0 to 999. In these embodiments, the organosilicon moiety Z is a siloxane moiety.

[0049] In some embodiments, each polyether moiety Y and each organosilicon moiety Z is linear, and the organosilicon moiety Z is a siloxane moiety, and the silicone-polyether copolymer has the following structure (when Z is present):

[0050]

[0051] wherein each Y, R 1 , subscript c, and subscript d are as defined above.

[0052] In one embodiment, not every organosilicon moiety Z is a siloxane moiety. For example, each organosilicon moiety Z can be a silyl-terminated organic compound. In particular embodiments, the organosilicon moiety Z can have the formula: -R 1 2Si-R 5 -SiR 1 2- wherein each R 1 is independent and as defined above, and R 5 is a divalent linking group. R 5 may be a divalent hydrocarbon group. Typically, the divalent hydrocarbon group is free of aliphatic unsaturation. The divalent hydrocarbon group can be linear, cyclic, branched, aromatic, or the like, or can have combinations of such structures. For example, R 5 may be a divalent aromatic group. When present, the organosilicon moiety Z is formed with a chain extending organosilicon compound, which will be described in more detail below.

[0053] The composition meets at least one of the following conditions: (i) the silicone-polyether copolymer includes at least one silicone moiety X of Formula (I) and at least one silicone moiety X of Formula (II); and / or (ii) the composition comprises at least one silicone-polyether copolymer (A) in which each silicone moiety X has Formula (I) and at least one silicone-polyether copolymer (B) in which each silicone moiety X has Formula (II). Effectively, the composition comprises at least one silicone moiety X of Formula (I) and at least one silicone moiety X of Formula (II) regardless of whether the at least one silicone moiety X of Formula (I) and the at least one silicone moiety X of Formula (II) are present in the same silicone-polyether copolymer or in different silicone-polyether copolymers. In view of the description herein, one skilled in the art can selectively adjust the cure rate of the composition by selectively controlling the molar ratio of the silicone moiety X of Formula (I) and the silicone moiety X of Formula (II) having different cure rates in the composition.

[0054] In certain embodiments, condition (i) is true and the silicone-polyether copolymer includes at least one silicone moiety X of Formula (I) and at least one silicone moiety X of Formula (II). In other embodiments, condition (ii) is true and the composition comprises at least one silicone-polyether copolymer (A) in which each silicone moiety X has Formula (I) and at least one silicone-polyether copolymer (B) in which each silicone moiety X has Formula (II). In other embodiments, condition (i) is true and condition (ii) is not true, or condition (ii) is true and condition (i) is not true, or both condition (i) and condition (ii) are true.

[0055] In specific embodiments where condition (i) is true, the silicone-polyether copolymer has the following formula:

[0056] X 1 g’ [Z j Y o ] c X 2 g”

[0057] where X 1 is a silicone moiety X of formula (I), X 2 is a silicone moiety X of formula (II), subscript g' > 1, subscript g" > 1, and Z, Y, and subscripts j, o, and c are as defined above. In more specific embodiments involving this formula, each of g' and g" is 1. In other specific embodiments involving this formula, g' is 1 or 2, and g" is 1 or 2, with the proviso that g' + g" = 3.

[0058] In these or other specific embodiments where condition (i) is true and when subscript j > 0, the silicone-polyether copolymer has the following formula:

[0059] (R 1 ) a (R 2 O) 3-a -Si-D-SiR 1 2-O-SiR 1 2-D 1 -Y-[(SiR 1 2O) d -SiR 1 2-Y] c -D 1 -Si-(OR 2 ) 3-a (R 1 ) a where each Y, R 1 , R 2 , subscript a, D, D 1 , subscript d, and subscript c are as defined above.

[0060] In these or other specific embodiments where condition (i) is true and when subscript j > 0, the silicone-polyether copolymer has the following formula:

[0061] (R 2 O)3-Si-D-SiR 1 2-O-SiR 1 2-D 1 -Y-[(SiR 1 2O)d -SiR 1 2-Y] c -D 1 -Si-(OR 2 )2(R 1 ) wherein each Y, R 1 , R 2 , D, D 1 , subscript d and subscript c are as defined above.

[0062] In these or other embodiments where condition (i) is true and when subscript j > 0, the silicone-polyether copolymer has the following formula:

[0063] (MeO)3-Si-D-SiR 1 2-O-SiR 1 2-D 1 -Y-[(SiR 1 2O) d -SiR 1 2-Y] c -D 1 -Si-(OMe)2(Me) wherein each Y, R 1 , R 2 , D, D 1 , subscript d and subscript c are as defined above, and Me represents a methyl group.

[0064] In these or other embodiments where condition (i) is true and when subscript j > 0, the silicone-polyether copolymer has the following formula:

[0065] (MeO)3-Si-C2H4-SiR 1 2-O-SiR 1 2-D 1 -Y-[(SiR 1 2O) d -SiR 1 2-Y] c -D 1 -Si-(OMe)2(Me) wherein each Y, R 1 , R 2 , D, D 1 , subscript d and subscript c are as defined above, and Me represents a methyl group.

[0066] In these or other embodiments where condition (i) is true and when subscript j > 0, the silicone-polyether copolymer has the following formula:

[0067] (MeO)3-Si-C2H4-SiR 1 2-O-SiR 1 2-D1 -Y-[(SiR 1 2O) d -SiR 1 2-Y] c -D 1 -Si-(OMe)3 wherein each Y, R 1 , R 2 , D, D 1 , subscript d and subscript c are as defined above, and Me represents methyl.

[0068] In specific embodiments, when condition (i) is true, the molar ratio of silicone moiety X of formula (I) to silicone moiety X of formula (II) is (I):(II) from 2:98 to 98:2. It has been surprisingly found that the curing speed can be maximized by increasing the content of silicone moiety X of formula (I) and the mechanical properties, such as modulus and elongation, of the cured product can be optimized (i.e. minimized) by increasing the content of silicone moiety X of formula (II). Typically, the industry focuses on maximizing the curing speed, which also disadvantageously increases the modulus of the resulting cured product. However, by maintaining an appropriate molar ratio of silicone moiety X of formula (I) to silicone moiety X of formula (II), the curing speed can be significantly increased without sacrificing mechanical properties such as modulus. In certain embodiments, when condition (i) is true, the mole % of silicone moiety X having formula (I) is greater than 0 to 50, alternatively from 1 to 40, alternatively 2 to 28, alternatively 3 to 27, alternatively 4 to 26, alternatively 5 to 25, alternatively 6 to 24, alternatively 7 to 23, alternatively 8 to 22, alternatively 9 to 21, alternatively 10 to 20, alternatively 11 to 19, alternatively 12 to 18, alternatively 13 to 17, alternatively 14 to 16, based on the total moles of silicone moiety X. In other embodiments, when condition (i) is true, the mole % of silicone moiety X having formula (I) is greater than 0 to 50, alternatively from 1 to 40, alternatively 1 to 35, alternatively 1 to 30, alternatively 1 to 25, alternatively 1 to 20, alternatively 2 to 15, based on the total moles of silicone moiety X.

[0069] In specific embodiments where condition (ii) is true, the composition comprises at least one silicone-polyether copolymer (A) wherein each silicone moiety X has formula (I), and at least one silicone-polyether copolymer (B) wherein each silicone moiety X has formula (II).

[0070] In this specific embodiment where condition (ii) is true, the silicone-polyether copolymer (A) has the following formula:

[0071] X 1 g”’ [Z j Y o ]c

[0072] and the silicone-polyether copolymer (B) has the following formula:

[0073] X 2 g”” [Z j Y o ] c

[0074] wherein X 1 is a silicone moiety X of formula (I), X 2 is a silicone moiety X of formula (II), the subscript g”’ is 1, the subscript g”” is >1, and Z, Y and the subscripts j, o and c are as defined above. In other specific embodiments involving this formula, each of g”’ and g”” is 2 or 3.

[0075] In these or other specific embodiments where condition (ii) is true and when the subscript j > 0, the at least one silicone-polyether copolymer (A) has the following formula:

[0076] (R 1 ) a (R 2 O) 3-a -Si-D-SiR 1 2-O-SiR 1 2-D 1 -Y-[(SiR 1 2O) d -SiR 1 2-Y] c -D 1 -SiR 1 2-O-SiR 1 2-

[0077] D-Si-(OR 2 ) 3-a (R 1 ) a ,

[0078] and the at least one silicone-polyether copolymer (B) has the following formula:

[0079] (R 1 ) a (R 2 O) 3-a -Si-D 1 -Y-[(SiR 1 2O) d -SiR 1 2-Y] c -D 1 -Si-(OR 2 )3-a (R 1 ) a wherein each Y, R 1 , R 2 , subscript a, D, D 1 , subscript d and subscript c are as defined above.

[0080] In these or other embodiments where condition (ii) is true and when subscript j > 0, the at least one silicone-polyether copolymer (A) has the following formula:

[0081] (R 2 O)3-Si-D-SiR 1 2-O-SiR 1 2-D 1 -Y-[(SiR 1 2O) d -SiR 1 2-Y] c -D 1 -SiR 1 2-O-SiR 1 2-D-Si-

[0082] (OR 2 )3,

[0083] and the at least one silicone-polyether copolymer (B) has the following formula:

[0084] (R 1 )(R 2 O)2-Si-D 1 -Y-[(SiR 1 2O) d -SiR 1 2-Y] c -D 1 -Si-(OR 2 )2(R 1 ), wherein each Y, R 1 , R 2 , D, D 1 , subscript d and subscript c are as defined above.

[0085] In these or other embodiments where condition (ii) is true and when subscript j > 0, the at least one silicone-polyether copolymer (A) has the following formula:

[0086] (MeO)3-Si-D-SiR 1 2-O-SiR 1 2-D 1 -Y-[(SiR 1 2O) d -SiR1 2-Y] c -D 1 -SiR 1 2-O-SiR 1 2-D-Si-

[0087] (OMe)3,

[0088] and at least one silicone-polyether copolymer (B) has the following formula:

[0089] (Me)(MeO)2-Si-D 1 -Y-[(SiR 1 2O) d -SiR 1 2-Y] c -D 1 -Si-(OMe)2(Me), wherein each Y, R 1 , R 2 , D, D 1 , subscript d and subscript c are defined as above, and Me represents methyl.

[0090] In these or other specific embodiments where condition (ii) is true and when subscript j > 0, at least one silicone-polyether copolymer (A) has the following formula:

[0091] (MeO)3-Si-D-SiR 1 2-O-SiR 1 2-D 1 -Y-[(SiR 1 2O) d -SiR 1 2-Y] c -D 1 -SiR 1 2-O-SiR 1 2-D-Si-

[0092] (OMe)3,

[0093] and at least one silicone-polyether copolymer (B) has the following formula:

[0094] (MeO)3-Si-D 1 -Y-[(SiR 1 2O) d -SiR 1 2-Y] c -D 1 -Si-(OMe)3,

[0095] wherein each Y, R 1 , R 2 , D, D1 , subscript d and subscript c are as defined above, and Me represents a methyl group.

[0096] When condition (ii) is true, the molar ratio of silicone-polyether copolymer (A) to silicone-polyether copolymer (B) is 2:98 to 98:2 (A):(B). The molar ratio can be selected based on the desired cure speed and performance characteristics of the composition and its cured product. Generally, increasing the content of silicone moiety X of formula (I) relative to the content of silicone moiety X of formula (II) increases the cure speed. The composition can also include three or more different silicone-polyether copolymers that differ in terms of viscosity, molecular weight, structure, etc. In certain embodiments, when condition (ii) is true, the mole % of silicone-polyether copolymer (A) in the composition is greater than 0 to 50, alternatively from 1 to 40, alternatively 2 to 28, alternatively 3 to 27, alternatively 4 to 26, alternatively 5 to 25, alternatively 6 to 24, alternatively 7 to 23, alternatively 8 to 22, alternatively 9 to 21, alternatively 10 to 20, alternatively 11 to 19, alternatively 12 to 18, alternatively 13 to 17, alternatively 14 to 16, based on the total amount of silicone-polyether copolymer (A) and silicone-polyether copolymer (B) in the composition. In other embodiments, when condition (ii) is true, the mole % of silicone-polyether copolymer (A) in the composition is greater than 0 to 50, alternatively from 1 to 40, alternatively 1 to 35, alternatively 1 to 30, alternatively 1 to 25, alternatively 1 to 20, alternatively 2 to 15, based on the total amount of silicone-polyether copolymer (A) and silicone-polyether copolymer (B) in the composition.

[0097] The above exemplary structures are based on each X, each Y, and / or each Z in the silicone-polyether copolymer being the same. However, as described above, each X, each Y, and each Z are independently selected. Thus, one of skill in the art readily understands the structure associated with the silicone-polyether copolymer based on the selection of each X, each Y, and / or each Z. Additionally, the above exemplary structures are generally linear. As is readily understood in the art, the silicone-polyether copolymer, as well as silicone-polyether copolymer (A) and silicone-polyether copolymer (B), can be branched, given the description herein. For example, in certain embodiments, the silicone-polyether copolymer includes three X moieties. The same conditions and descriptions apply to such embodiments, and one of skill in the art readily understands the structure of such branched silicone-polyether copolymers given the broad description herein.

[0098] Also disclosed is a method of making a silicone-polyether copolymer. The method includes reacting a polyether compound having on average more than one terminal unsaturated group, optionally a chain extending organosilicon compound, a first endblocking organosilicon compound, and a second endblocking organosilicon compound different from the first endblocking organosilicon compound in the presence of a hydrosilylation catalyst to make a composition comprising the at least one silicone-polyether copolymer.

[0099] As will be appreciated by one of skill in the art in view of the description herein, the polyether compound used in the method forms the portion of the silicone-polyether copolymer corresponding to the polyether portion Y, the chain extending organosilicon compound used in the method forms the portion of the silicone-polyether copolymer corresponding to the organosilicon portion Z, if used, and the first and second endblocking organosilicon compounds used in the method form the portion of the silicone-polyether copolymer corresponding to the silicone portion Z (based on Formula I and Formula II above for X).

[0100] Typically, the polyether compound has the following formula: Y 1 [R 4 ] i where each R 4 is an independently selected unsaturated group having 2 to 14 carbon atoms; the subscript i > 1; and Y 1 is a polyether portion comprising at least one polyether group.

[0101] Each R 4 is an independently selected unsaturated group having 2 to 14 carbon atoms. Typically, R 4 comprises an alkenyl group or an alkynyl group, alternatively an alkenyl group or an alkynyl group. Illustrative examples include H2C=CH–, H2C=CHCH2–, H2C=CHCH2CH2–, H2C=CH(CH2)3–, H2C=CH(CH2)4–, H2C=C(CH3)–, H2C=C(CH3)CH2–, H2C=C(CH3)CH2CH2–, H2C=C(CH3)CH2CH(CH3)–, H2C=C(CH3)CH(CH3)CH2–, H2C=C(CH3)C(CH3)2–, HC≡C–, HC≡CCH2–, HC≡CCH(CH3)–, HC≡CC(CH3)2–, and HC≡CC(CH3)2CH2–.

[0102] In certain embodiments, each R 4 has the formula CH2C(R 3 )–[D 2 ] m where each R 3independently a hydrocarbyl group, an alkoxy group, a silyl group, or H having 1 to 6 carbon atoms; each D 2 is a divalent group independently selected having 1 to 6 carbon atoms, and subscript m is 0 or 1. In certain embodiments, R 3 is -CH3. In these or other embodiments, D 2 is -CH2-. In specific embodiments, each R 4 is H2C=C(CH3)CH2-.

[0103] subscript i > 1, such as 2, 3, 4, 5, 6, etc. Typically, the polyether compound comprises R 1 at each end of Y 4 such that subscript i corresponds to the valence of Y 1 which is at least 2, but can be 3, 4, 5, or higher depending on its branching. In specific embodiments, subscript i is 2. In other specific embodiments, subscript i is 3.

[0104] each Y 1 is a polyether moiety comprising at least one polyether group, such as any of the polyether groups described above. Typically, the polyether group of Y 1 has the general formula -0-(C n H 2n O) w -, wherein subscript n is independently selected from 2 to 4 in each moiety indicated by subscript w, and subscript w is 1 to 1000. In certain embodiments, at least one polyether group of Y 1 has the formula -0-[C2H4O] x [C3H6O] y [C4H8O] z -, wherein each subscript x is independently 0 to 999, each subscript y is independently 1 to 1000, and each subscript z is independently 0 to 999, and wherein the units indicated by subscript x, subscript y, and subscript z can be in random or block form in the polyether group.

[0105] In some embodiments, Y 1 is branched and has the general formula [R 4 ] i' [P], wherein R 4 is as defined above, subscript i' ≥ 3 (e.g., 3, 4, 5, 6, 7, 8, 9, 10, etc.), and P is a polyether comprising at least one of the polyethers described above. For example, in some such embodiments, P is a polyether formed from a polyol (e.g., butanediol, glycerol, sorbitol, etc.) and 2, 3, or more polyoxyalkylenes (e.g., polyoxypropylene) in i' number of R 4Partially end-capped. In such cases, the number of alcohol functions making up the polyol will correspond to the maximum number of i'. However, if not all of the polyoxyalkylene chains extending from the polyol are end-capped, i' will be less than the number of alcohol functions making up the polyol.

[0106] In certain embodiments, the polyether compound is linear and i = 2, such that the polyether compound has the formula R 4 –Y 1 –R 4 where Y 1 and each R 4 is as defined above. For example, in some such embodiments, the polyether compound has the following formula:

[0107] CH2C(R 3 )–[D 2 ] m –O–[C2H4O] x [C3H6O] y [C4H8O] z –[D 2 ] m –C(R 3 )CH2,

[0108] where each R 3 , D 2 , subscript m, subscript x, subscript y, and subscript z are as defined above. In specific embodiments, each R 3 is methyl, each D 2 is CH2, and each subscript m is 1. In these or other embodiments, subscript x and subscript z are each 0, such that the polyether portion of the polyether compound contains only oxypropylene units.

[0109] Chain extending silicone compounds are typically linear silicone compounds having at least 2 terminal silicon-bonded H groups. However, chain extending silicone compounds can be branched, and have 3, 4, or more terminal silicon-bonded H groups. For example, the chain extending silicone compound can have one of the following formulas:

[0110]

[0111] where Z' is a siloxane moiety, and each R 1 is as defined above. As such, the chain extending silicone compound typically includes a linear hydrosilicon-functional silicone compound, a branched hydrosilicon-functional silicone compound, or both.

[0112] In specific embodiments, the chain extending silicone compound is linear and is an organohydrogensiloxane having the following formula:

[0113]

[0114] wherein each R 1 as defined above, and subscript d is 1 to 999.

[0115] In other embodiments, not every Z' is a siloxane moiety. For example, the chain extending organosilicon compound can have the following formula: HR 1 2Si-R 5 -SiR 1 2H, wherein each R 1 is independent and as defined above, and R 5 is a divalent linking group. R 5 may be a divalent hydrocarbon group. Typically, the divalent hydrocarbon group is free of aliphatic unsaturation. The divalent hydrocarbon group can be linear, cyclic, branched, aromatic, or the like, or can have combinations of such structures. For example, R 5 may be a divalent aromatic group.

[0116] When R 5 is a divalent aromatic group, specific examples of the chain extending organosilicon compound include:

[0117]

[0118] As introduced above, the first end-capped organosilicon compound and the second end-capped organosilicon compound used in the process form the silicone moiety X having the above Formula (I) and Formula (II). Thus, the first end-capped organosilicon compound and the second end-capped organosilicon compound can be any organosilicon compound suitable for forming a silicone-polyether copolymer, including silicone-polyether copolymer (A) and silicone-polyether copolymer (B), as understood in the art. Typically, the first end-capped organosilicon compound and the second end-capped organosilicon compound are each an organohydrogensiloxane compound comprising at least one silicon-bonded hydrogen atom. In the presence of the hydrosilylation catalyst used in the process, the silicon-bonded hydrogen atom in each organohydrogensiloxane compound reacts via a hydrosilylation reaction with the unsaturated group R 4 in the polyether compound.

[0119] In certain embodiments, the first end-capped organosilicon compound has the following formula:

[0120] (R 1 ) a (R 2 O) 3-a Si-D-SiR 1 2-O-SiR 1 2H

[0121] wherein each R 1 is independently selected and as defined above, and each R 2are independently selected alkyl groups having 1 to 8 carbon atoms; each D is independently a divalent hydrocarbon group having 2 to 18 carbon atoms; and subscript a is 0 or 1. The first end-capped organosilicon compound results in X of formula (I) in the silicone-polyether copolymer.

[0122] In particular embodiments, the first end-capped organosilicon compound has the following formula:

[0123] (R 2 O)3Si-D-SiR 1 2-O-SiR 1 2H,

[0124] wherein R 1 and R 2 are independently selected and are as defined above, and D is as defined above.

[0125] In these or other particular embodiments, the first end-capped organosilicon compound has the following formula:

[0126] (MeO)3Si-D-SiR 1 2-O-SiR 1 2H,

[0127] wherein R 1 is independently selected and is as defined above, and D is as defined above.

[0128] In these or other particular embodiments, the first end-capped organosilicon compound has the following formula:

[0129] (MeO)3Si-C2H4-SiR 1 2-O-SiR 1 2H,

[0130] wherein R 1 is independently selected and is as defined above.

[0131] In these or other particular embodiments, the first end-capped organosilicon compound has the following formula:

[0132] (MeO)3Si-CH2CH2-Si(Me)2-O-Si(Me)2H.

[0133] In these or other embodiments, the second end-capped organosilicon compound has the following formula:

[0134] (R 1 ) a (R 2 O) 3-a SiH

[0135] wherein each R 1are independently selected and are as defined above, and each R 2 are independently selected and are as defined above; each D is independently a divalent hydrocarbon group having 2 to 18 carbon atoms; and subscript a is 0 or 1. The second end-capped organosilicon compound results in X of formula (II) in the silicone-polyether copolymer.

[0136] In particular embodiments, the second end-capped organosilicon compound has the following formula:

[0137] (R 1 )(R 2 O)2SiH

[0138] wherein R 1 and R 2 are independently selected and are as defined above.

[0139] In these or other particular embodiments, the second end-capped organosilicon compound has the following formula:

[0140] (Me)(MeO)2SiH,

[0141] wherein Me represents a methyl group.

[0142] In other particular embodiments, the second end-capped organosilicon compound has the following formula:

[0143] (R 2 O)3SiH,

[0144] wherein R 2 are independently selected and are as defined above. In these particular embodiments, R 2 are typically independently methyl or ethyl groups.

[0145] Organohydrogensiloxane compounds suitable for use as the first end-capped organosilicon compound and the second end-capped organosilicon compound can be prepared via any suitable technique.

[0146] A third end-capped organosilicon compound or additional end-capped organosilicon compounds can also be used in the method. For example, the third end-capped organosilicon compound can fall within formula (I) or formula (II) for the silicone moiety X, while still being distinguished from other end-capped organosilicon compounds falling within the same general formula (I) or general formula (II).

[0147] Further, in certain embodiments, the method can involve a transalkoxylation reaction involving one or more silicon-bonded alkoxy groups of the first end-capped organosilicon compound or the second end-capped organosilicon compound. For example, the second end-capped organosilicon compound can have the following formula: (R 2 O)3SiH, wherein each R 2is ethyl. In such embodiments, the ethoxy groups present in the resulting silicone-polyether copolymer can be converted to methoxy groups by reacting the ethoxy groups with methanol.

[0148] The polyether compound, optionally the chain extending organosilicon compound, and the first and second endblocking organosilicon compounds can be reacted in any order or combination to give the composition comprising at least one silicone-polyether copolymer, as is understood in the art. Additionally, the order of addition or method can depend on which of condition (i) and condition (ii) is true. For example, when condition (i) is true, the polyether compound, optionally the chain extending organosilicon compound, and the first and second endblocking organosilicon compounds can be reacted together in a single tank in any order of addition. Alternatively, when condition (ii) is true, silicone-polyether copolymer (A) can be made in the absence of the second endblocking organosilicon compound, and silicone-polyether copolymer (B) can be made in the absence of the first endblocking organosilicon compound, and silicone-polyether copolymer (A) can be subsequently combined with silicone-polyether copolymer (B) to give the composition. Further, when used, the chain extending organosilicon compound can be used prior to the first and / or second endblocking organosilicon compound, such that chain extension occurs prior to endblocking. When both the first and second organosilicon compounds are used together in the method, i.e., when condition (i) is true, they can be combined with the other components simultaneously or at different times.

[0149] In certain embodiments, the method comprises: reacting a polyether compound and a chain extending organosilicon compound in the presence of a hydrosilylation catalyst to give a siloxane-polyether compound (i.e., a chain extended silicone-polyether compound); and reacting the siloxane-polyether compound and a first and / or second endblocking organosilicon compound in the presence of a hydrosilylation catalyst to give the composition comprising at least one silicone-polyether copolymer. The siloxane-polyether compound can be prepared by any suitable technique. For example, in certain embodiments, the siloxane-polyether copolymer is prepared by reacting a polyether compound having two terminal unsaturated groups and a chain extending organosilicon compound in the presence of a hydrosilylation catalyst to give the composition comprising at least one siloxane-polyether compound.

[0150] The siloxane-polyether compound used in such embodiments forms part of a silicone-polyether copolymer having the formula: j Y o ] c wherein Z, Y, subscript c, and subscripts j and o are as defined above. For example, when the polyether portion Y and the organosilicon portion Z are present and are linear, the siloxane-polyether compound can have the following formula:

[0151]

[0152] wherein each Y, R 1 , subscript c and subscript d are as defined above. Thus, the siloxane-polyether compound used can be selected based on the desired structure of the silicone-polyether copolymer, e.g., based on the molecular weight, the particular structure of each Y (i.e., the units within each Y), the degree of polymerization of the siloxy units denoted by subscript d, etc.

[0153] In certain embodiments, the siloxane-polyether compound has the following formula:

[0154]

[0155] In such embodiments, each Y 1 , R 1 and R 4 are as defined above, and subscript c is generally 1 to 150, such as 1 to 100, alternatively 1 to 50, alternatively 1 to 25, alternatively 1 to 10, and alternatively 1 to 5. Generally, in each moiety denoted by subscript c, each subscript d is 1 to 1000, such as 1 to 500, alternatively 1 to 300, alternatively 1 to 100, alternatively 1 to 50, and alternatively 1 to 10.

[0156] When used, the polyether compound and the chain extending organosilicon compound are generally reacted in a molar ratio of 1.001 : 1 to 2: 1; alternatively 1.4: 1 to 1.7: 1; alternatively 1.05: 1 to 1.5: 1; alternatively 1.1 : 1 to 1.2: 1; and alternatively 1.2: 1 to 1.5: 1. The siloxane-polyether compound is generally formed by bringing the molar ratio of the polyether compound to the chain extending organosilicon compound to the desired subscript c value.

[0157] The silicone-polyether compound, and the first and / or second endcapped organosilicon compounds are generally reacted in a molar ratio of 1.5: 1 to 1: 1.5 (alternatively 1.4: 1 to 1: 1.4, alternatively 1.3: 1 to 1: 1.3, alternatively 1.2: 1 to 1: 1.2, alternatively 1.1 : 1 to 1: 1.1, alternatively 1.1 : 1 to 1: 1) between the unsaturated groups of the silicone-polyether compound and the silicon hydride groups of the first and second endcapped organosilicon compounds. When the silicone-polyether compound is difunctional, the silicone-polyether copolymer is generally formed from a 1:2 molar ratio of the silicone-polyether compound to the first and second endcapped organosilicon compounds, but a molar excess of one to the other of the silicone-polyether compound to the first and second endcapped organosilicon compounds can be used.

[0158] In certain embodiments, the method comprises: reacting a polyether compound with a first endcapped organosilicon compound and / or a second endcapped organosilicon compound in the presence of a hydrosilylation catalyst to give an endcapped silicone-polyether compound; and reacting the endcapped silicone-polyether compound with a chain extending organosilicon compound in the presence of a hydrosilylation catalyst to give a composition comprising at least one silicone-polyether copolymer. In these or other embodiments, the method comprises: reacting at least some polyether compound with some first endcapped organosilicon compound and / or second endcapped organosilicon compound to give a composition comprising at least one endcapped silicone-polyether compound; and also reacting at least some polyether compound with some chain extending organosilicon compound to give a composition comprising at least one siloxane-polyether compound, as described above for each. In yet other embodiments where no chain extending organosilicon compound is used, the method comprises reacting a polyether compound with a first endcapped organosilicon compound and / or a second endcapped organosilicon compound in the presence of a hydrosilylation catalyst to give a composition comprising at least one silicone-polyether copolymer.

[0159] The hydrosilylation reaction catalyst is not limited and can be any known hydrosilylation reaction catalyst for catalyzing a hydrosilylation reaction. Combinations of different hydrosilylation reaction catalysts can be used.

[0160] In certain embodiments, the hydrosilylation reaction catalyst comprises a Group VIII to Group XI transition metal. Group VIII to Group XI transition metals refer to the modern IUPAC nomenclature. Group VIII transition metals are iron (Fe), ruthenium (Ru), osmium (Os), and hassium (Hs); Group IX transition metals are cobalt (Co), rhodium (Rh), and iridium (Ir); Group X transition metals are nickel (Ni), palladium (Pd), and platinum (Pt); and Group XI transition metals are copper (Cu), silver (Ag), and gold (Au). Combinations thereof, complexes thereof (e.g., organometallic complexes), and other forms of such metals can be used as hydrosilylation reaction catalysts.

[0161] Additional examples of catalysts suitable for the hydrosilylation reaction catalyst include rhenium (Re), molybdenum (Mo), Group IV transition metals (i.e., titanium (Ti), zirconium (Zr), and / or hafnium (Hf)), lanthanides, actinides, and Group I and II metal complexes (e.g., including complexes of calcium (Ca), potassium (K), strontium (Sr), and the like). Combinations thereof, complexes thereof (e.g., organometallic complexes), and other forms of such metals can be used as hydrosilylation reaction catalysts.

[0162] The hydrosilylation reaction catalyst can be in any suitable form. For example, the hydrosilylation reaction catalyst can be a solid, examples of which include platinum-based catalysts, palladium-based catalysts, and similar noble metal-based catalysts, as well as nickel-based catalysts. Specific examples include nickel, palladium, platinum, rhodium, cobalt, and similar elements, as well as platinum-palladium, nickel-copper-chromium, nickel-copper-zinc, nickel-tungsten, nickel-molybdenum, and similar catalysts including combinations of multiple metals. Additional examples of solid catalysts include Cu-Cr, Cu-Zn, Cu-Si, Cu-Fe-Al, Cu-Zn-Ti, and similar copper-containing catalysts, among others.

[0163] The hydrosilylation reaction catalyst can be located in or on a solid support. Examples of supports include activated carbon, silica, silica alumina, alumina, zeolites, and other inorganic powders / particles (e.g., sodium sulfate), among others. The hydrosilylation reaction catalyst can also be provided in a vehicle, such as a solvent that dissolves the hydrosilylation reaction catalyst, or a vehicle that merely carries but does not dissolve the hydrosilylation reaction catalyst. Such vehicles are known in the art.

[0164] In particular embodiments, the hydrosilylation reaction catalyst includes platinum. In these embodiments, the hydrosilylation reaction catalyst is exemplified by, for example, platinum black, compounds such as chloroplatinic acid, chloroplatinic acid hexahydrate, reaction products of chloroplatinic acid and monohydric alcohols, bis(acetylacetone) platinum, bis(acetylacetone) platinum, platinum chloride, and complexes of such compounds with olefins or organopolysiloxanes, as well as platinum compounds microencapsulated in a matrix or core-shell type compound. Microencapsulated hydrosilylation catalysts and methods of making the same are also known in the art, as exemplified in U.S. Patents 4,766,176 and 5,017,654, which are incorporated by reference herein in their entirety.

[0165] Complexes of platinum with organopolysiloxanes suitable for use as the hydrosilylation reaction catalyst include complexes of 1,3-divinyl-1,1,3,3-tetramethyldisiloxane with platinum. These complexes can be microencapsulated in a resin matrix. Alternatively, the hydrosilylation reaction catalyst can include complexes of 1,3-divinyl-1,1,3,3-tetramethyldisiloxane with platinum. The hydrosilylation reaction catalyst can be prepared by a method including reacting chloroplatinic acid with an aliphatically unsaturated organosilicon compound such as divinyltetramethyldisiloxane or an olefin-platinum-silyl complex. The olefin-platinum-silyl complex can be prepared, for example, by mixing 0.015 moles (COD) PtCl2with 0.045 moles COD and 0.0612 moles HMeSiCl2, where COD represents cyclooctadiene.

[0166] Additional examples of suitable hydrosilylation catalysts for the components are described in, for example, U.S. Patent Nos. 3,159,601; 3,220,972; 3,296,291; 3,419,593; 3,516,946; 3,814,730; 3,989,668; 4,784,879; 5,036,117; and 5,175,325; the disclosures of which are incorporated by reference herein in their entireties.

[0167] The hydrosilylation catalyst can also be or alternatively be a photoactivatable hydrosilylation catalyst, which can initiate curing via irradiation and / or heat. The photoactivatable hydrosilylation catalyst can be any hydrosilylation catalyst capable of catalyzing a hydrosilylation reaction, particularly upon exposure to radiation having a wavelength of 150 nanometers to 800 nanometers (nm).

[0168] In certain embodiments, the silicone-polyether copolymer can be prepared in the absence of any solvent or vehicle. In other embodiments, the silicone-polyether copolymer is formed in the presence of a diluent, which is generally not reactive with the silicone-polyether copolymer or components used to prepare the silicone-polyether copolymer. The diluent can be a solvent or vehicle, examples of which are described below with respect to sealants formed with the composition. In such embodiments, the solvent or vehicle can be removed from the composition after preparation of the silicone-polyether copolymer, or can be retained. In other embodiments, the diluent can be considered a plasticizer, particularly when the composition is used to prepare a sealant. For example, conventional sealants generally include a plasticizer, and thus the plasticizer can provide a benefit in reducing the viscosity of the reaction mixture when preparing the silicone-polyether copolymer, and can be retained in the composition for sealant purposes, thus reducing additional compounding steps relative to the sealant.

[0169] The composition can be used in a variety of end-use applications. In certain embodiments, the composition is further defined as a sealant. When the composition is a sealant, the sealant includes a condensation reaction catalyst. Embodiments involving the composition as a sealant are as follows.

[0170] The condensation reaction catalyst is not limited, and in some embodiments, the condensation reaction catalyst is exemplified by tin catalysts, titanium catalysts, zirconate catalysts, and zirconium catalysts. General examples of suitable tin catalysts include organotin compounds in which the valence of tin is +4 or +2 (e.g., tin (IV) compounds and / or tin (II) compounds). Specific examples of tin (IV) compounds include stannic salts of carboxylic acids such as dibutyl tin dilaurate, dimethyl tin dilaurate, di(n-butyl) tin bis-ketonate, dibutyl tin diacetate, dibutyl tin maleate, dibutyl tin diacetylacetone, dibutyl tin dimethoxide, trioximate phenyl tin, dibutyl tin dioctoate, dibutyl tin dimalate, isobutyl tin triceroate, dimethyl tin dibutyrate, dimethyl tin didecanoate, dibutyl tin didecanoate, triethyl tin tartrate, dibutyl tin dibenzoate, butyl tin tri-2-ethylhexanoate, dioctyl tin diacetate, tin octoate, tin oleate, tin butyrate, tin naphthenate, dimethyl tin dichloride, combinations thereof, and / or partial hydrolyzates thereof. Additional examples of tin (IV) compounds are known in the art and commercially available, such as Tyzor® AA from Acima Specialty Chemicals, Switzerland, Europe, and Ultran® UL-28 from Galata Chemicals, Hahnville, LA. Specific examples of tin (II) compounds include: tin (II) salts of organic carboxylic acids such as tin (II) diacetate, tin (II) dioctoate, tin (II) diethylhexanoate, tin (II) dilaurate; stannous salts of carboxylic acids such as stannous octoate, stannous oleate, stannous acetate, stannous laurate, stannous stearate, stannous naphthenate, stannous hexanoate, stannous succinate, stannous octoate, and combinations thereof. Examples of suitable titanium catalysts include: titanium esters such as tetra-n-butyl titanate, tetra-isopropyl titanate, tetra-2-ethylhexyl titanate, tetraphenyl titanate, triethanolamine titanate, organosiloxy titanium compounds; and titanium dicarbonyl compounds such as titanium ethyl acetoacetate, diisopropyl bis(ethoxyacetoacetyl) titanium, and bis(acetylacetonato)-diisopropoxy titanium (IV). Many of these titanium catalysts are commercially available, such as Tyzor® AA from Dorf Ketal Specialty Catalysts LLC, Houston, TX, and Ultran® UL-28 from Galata Chemicals, Hahnville, LA. Specific examples of zirconate catalysts include: zirconate esters such as tetra-n-butyl zirconate, tetra-2-ethylhexyl zirconate, tetra-phenyl zirconate, triethanolamine zirconate, organosiloxy zirconium compounds; and zirconium dicarbonyl compounds such as zirconium ethyl acetoacetate, diisopropyl bis(ethoxyacetoacetyl) zirconium, and bis(acetylacetonato)-diisopropoxy zirconium (IV). Many of these zirconate catalysts are commercially available, such as Tyzor® AA from Acima Specialty Chemicals, Switzerland, Europe, and Ultran® UL-28 from Galata Chemicals, Hahnville, LA. Specific examples of zirconium catalysts include: zirconium esters such as tetra-n-butyl zirconium, tetra-2-ethylhexyl zirconium, tetra-phenyl zirconium, triethanolamine zirconium, organosiloxy zirconium compounds; and zirconium dicarbonyl compounds such as zirconium ethyl acetoacetate, diisopropyl bis(ethoxyacetoacetyl) zirconium, and bis(acetylacetonato)-diisopropoxy zirconium (IV). Many of these zirconium catalysts are commercially available, such as Tyzor® AA from Acima Specialty Chemicals, Switzerland, Europe, and Ultran® UL-28 from Galata Chemicals, Hahnville, LA. 740 and 4202, which is a business segment of The Dow Chemical Company, and Ultran® UL-28 from Galata Chemicals, Hahnville, LA. Tyzor® AA from Acima Specialty Chemicals, Switzerland, Europe, and Ultran® UL-28 from Galata Chemicals, Hahnville, LA. Specific examples of tin (II) compounds include: tin (II) salts of organic carboxylic acids such as tin (II) diacetate, tin (II) dioctoate, tin (II) diethylhexanoate, tin (II) dilaurate; stannous salts of carboxylic acids such as stannous octoate, stannous oleate, stannous acetate, stannous laurate, stannous stearate, stannous naphthenate, stannous hexanoate, stannous succinate, stannous octoate, and combinations thereof. Examples of suitable titanium catalysts include: titanium esters such as tetra-n-butyl titanate, tetra-isopropyl titanate, tetra-2-ethylhexyl titanate, tetraphenyl titanate, triethanolamine titanate, organosiloxy titanium compounds; and titanium dicarbonyl compounds such as titanium ethyl acetoacetate, diisopropyl bis(ethoxyacetoacetyl) titanium, and bis(acetylacetonato)-diisopropoxy titanium (IV). Many of these titanium catalysts are commercially available, such as Tyzor TM DC, Tyzor TM TnBT, and Tyzor TM9000. In certain embodiments, the condensation reaction catalyst is a titanium catalyst, such as one of those exemplified above, for example, where the sealant is or can be formulated as a room temperature vulcanizing sealant composition. The amount of condensation reaction catalyst present in the sealant depends on various factors (e.g., the amount and / or type of at least one silicone-polyether copolymer, the type and / or amount of any additional materials present in the sealant, etc.), and can be readily determined by one of skill in the art. In one embodiment, the sealant includes the condensation reaction catalyst in an amount of 0.2 to 6 parts by weight, alternatively 0.5 to 3 parts by weight, based on the total weight of the at least one silicone-polyether copolymer present in the sealant. In other embodiments, the sealant includes the condensation reaction catalyst in an amount of greater than 0 to 0.2 parts by weight, alternatively greater than 0 to 0.15 parts by weight, alternatively greater than 0 to 0.125 parts by weight, alternatively greater than 0 to 0.10 parts by weight, based on the total weight of the at least one silicone-polyether copolymer present in the sealant.

[0171] In some embodiments, the sealant further includes one or more additives. Examples of suitable additives that can be present in the sealant include fillers, treating agents (e.g., filler treating agents), crosslinking agents, adhesion promoters, surface modifiers, driers, extenders, biocides, flame retardants, plasticizers, capping agents, tackifiers, anti-aging additives, water release agents, pigments, dyes, rheology modifiers, carriers, tackifiers, corrosion inhibitors, catalyst inhibitors, viscosity modifiers, UV absorbers, antioxidants, light stabilizers, and the like, and combinations thereof.

[0172] In certain embodiments, the sealant includes a filler. The filler can be or include a reinforcing filler, a compatabilizing filler, an electrically conductive filler (e.g., electrically conductive, thermally conductive, or both), and the like, or combinations thereof. Examples of suitable reinforcing fillers include precipitated calcium carbonate and reinforcing silica fillers, such as fumed silica, silica aerogel, silica xerogel, and precipitated silica. Particular suitable precipitated calcium carbonates include Omyacarb® from Solvay, Micropure® and Micropure® 100 from Imerys, and Calci-Pak® from Specialty Minerals, Inc. SPM and Micropure® from Specialty Minerals, Inc. and 100.Examples of fumed silica are known in the art and commercially available, such as those sold under the name CAB-O-SIL by Cabot Corporation, Massachusetts, U.S.A. Examples of suitable extender fillers include crushed quartz, alumina, magnesium oxide, calcium carbonate (such as ground calcium carbonate, precipitated calcium carbonate), zinc oxide, talc, diatomaceous earth, iron oxide, clay, mica, chalk, titanium dioxide, zirconium oxide, sand, carbon black, graphite, or combinations thereof. Examples of extender fillers are known in the art and commercially available, including quartz powder sold under the name MIN-U-SIL by U.S. Silica, Berkeley Springs, WV. Other examples of commercially available extender fillers include calcium carbonate sold under the name CS-11 by Imerys, calcium carbonate sold under the name G3T by Huber, calcium carbonate sold under the name Pfinyl 402 by Specialty Minerals, Inc, and calcium carbonate sold under the name Omyacarb 2T by Omya. The amount of filler present in the sealant depends on various factors (e.g., the amount and / or type of at least one silicone-polyether copolymer, the type and / or amount of any additional materials present in the sealant, etc.), and can be readily determined by one of skill in the art. The exact amount of filler used in a particular embodiment of the sealant will also depend on whether more than one type of filler is used. Generally, where a filler is present, the sealant comprises the filler in an amount of 0.1 to 95 weight percent, alternatively 1 to 60 weight percent, alternatively 1 to 20 weight percent, based on the weight of the sealant.

[0173] In particular embodiments, the sealant comprises a treatment agent. The treatment agent is not limited and can be any treatment agent suitable for treating (e.g., surface treating) additives in the sealant, such as fillers and other additives (e.g., physical drying agents, flame retardants, pigments, and / or water release agents) that can be present in the sealant. More particularly, solid and / or particulate additives can be treated with a treatment agent prior to being added to the sealant. Alternatively or additionally, solid and / or particulate additives can be treated in situ with a treatment agent. General examples of suitable treatment agents include those comprising alkoxysilanes, alkoxyl-functional oligosiloxanes, cyclic polyorganosiloxanes, hydroxyl-functional oligosiloxanes (e.g., dimethylsiloxanes or methylphenylsiloxanes), fatty acids (e.g., stearates such as calcium stearate), and the like, as well as combinations thereof. Particular examples of treatment agents include alkyl mercaptans, fatty acids, titanates, titanate coupling agents, zirconate coupling agents, and the like, as well as combinations thereof.

[0174] In some embodiments, the treating agent is or comprises an organosilicon filler treating agent. Examples of such organosilicon filler treating agents include compositions suitable for treating silica fillers, such as organochlorosilanes, organosiloxanes, organodisilazanes (e.g., hexaalkyldisilazanes), and organoalkoxysilanes (e.g., CH3Si(OCH3)3, C6H5CH2CH2Si(OCH3)3, etc.). In these or other embodiments, the treating agent is or comprises an alkoxysilane having formula (X): R 13 Si(OCH3)3, C8H 17 Si(OC2H5)3, C 10 H 21 Si(OCH3)3, C 12 H 25 Si(OCH3)3, C 14 H 29 Si(OC2H5)3, C6H5CH2CH2Si(OCH3)3, etc.). In these or other embodiments, the treating agent is or comprises an alkoxysilane having formula (X): R 10 A Si(OR 11 ) 4-A In formula (X), subscript A is an integer from 1 to 3, such as 1, 2, or 3. Each R 10 is an independently selected monovalent organic group, such as a monovalent hydrocarbon group having from 1 to 50 carbon atoms, alternatively from 8 to 30 carbon atoms, alternatively from 8 to 18 carbon atoms, alternatively from 1 to 5 carbon atoms. R 10 may be saturated or unsaturated, and branched or unbranched. Alternatively, R 10 may be saturated and unbranched. R 10 Examples of R 11 are alkyl groups, such as methyl, ethyl, hexyl, octyl, dodecyl, tetradecyl, hexadecyl, and octadecyl; alkenyl groups, such as vinyl; and aryl groups, such as benzyl and phenethyl. Each R 12 is an independently selected saturated hydrocarbon group having from 1 to 4 carbon atoms, alternatively from 1 to 2 carbon atoms. Particular examples of organosilicon filler treating agents also include hexyltrimethoxysilane, octyltriethoxysilane, decyltrimethoxysilane, dodecyltrimethoxysilane, tetradecyltrimethoxysilane, phenethyltrimethoxysilane, octadecyltrimethoxysilane, octadecyltriethoxysilane, and combinations thereof.

[0175] In some embodiments, the treating agent is or comprises an alkoxyl-functional oligosiloxane. Examples of suitable alkoxyl-functional oligosiloxanes include those having general formula (XI): (R B O) 13 Si(OSiR 14 ) (4-B)In Formula (XI), subscript B is 1, 2, or 3. In specific embodiments, subscript B is 3. Each R 12 is an independently selected alkyl group. Each R 13 is an independently selected unsaturated monovalent hydrocarbon group having 1 to 10 carbon atoms. Each R 14 is an independently selected unsaturated monovalent hydrocarbon group having at least 10 carbon atoms.

[0176] In certain embodiments, the treating agent is or comprises a polyorganosiloxane capable of hydrogen bonding. Such treating agents use clusters and / or dispersed multiple hydrogen bonds as a means of tethering the compatibilizing moiety to the surface of a sealant component (e.g., filler) to be treated. Suitable polyorganosiloxanes capable of hydrogen bonding have, on average, at least one silicon-bonded group per molecule capable of hydrogen bonding, typically selected from the group consisting of organic groups having multiple hydroxyl functional groups, organic groups having at least one amino functional group, and combinations thereof. In other words, the polyorganosiloxane capable of hydrogen bonding typically utilizes hydrogen bonding as the primary means of attachment to the filler. Thus, in some embodiments, the polyorganosiloxane is not capable of forming a covalent bond with the filler. The polyorganosiloxane can be free of condensable silyl groups (e.g., silicon-bonded alkoxy groups, silazanes, and silanols). Examples of suitable polyorganosiloxanes for use in or as sealants include sugar-siloxane polymers, amino-functional polyorganosiloxanes, and combinations thereof. In specific embodiments, the sealant comprises a polyorganosiloxane comprising a sugar-siloxane polymer.

[0177] The amount of treating agent present in the sealant depends on various factors (e.g., the amount and / or type of at least one silicone-polyether copolymer, the type and / or amount of any additional materials present in the sealant (such as materials treated with the treating agent), etc.) and can be readily determined by one skilled in the art. Generally, the amount of treating agent varies depending on the type of treating agent selected, the type and / or amount of particles to be treated, and whether the particles are treated prior to being added to the sealant or treated in situ. Generally, in the presence of a treating agent, the sealant comprises the treating agent in an amount ranging from 0.01 wt% to 20 wt%, alternatively from 0.1 wt% to 15 wt%, alternatively from 0.5 wt% to 5 wt%, based on the weight of the sealant.

[0178] In some embodiments, the sealant includes a polymeric additive, such as a crosslinker, a chain extender, a plasticizer, an end-capper, or the like, or a combination thereof. Generally, suitable polymeric additives include compounds having functional groups that react with functional groups present in at least one of the silicone-polyether copolymers of the sealant or with functional groups present in another polymeric additive that has reacted therewith. Certain polymeric additives can be named based on the intended function (e.g., crosslinking, chain extending, end-capping, etc.). However, it should be understood that there can be overlap between the functions of the various types of polymeric additives, as certain polymeric additives described herein can have more than one function, as will be readily understood by one of skill in the art. For example, suitable crosslinkers include crosslinkers that include compounds having, on average, two or more substituents per molecule that are reactive with the alkoxy groups present within at least one of the silicone-polyether copolymers, and suitable chain extenders include chain extenders that include compounds having, on average, two substituents per molecule that are reactive with the alkoxy groups present within at least one of the silicone-polyether copolymers or with groups present within another polymeric additive that is reactive with at least one of the silicone-polyether copolymers. Thus, as will be understood by one of skill in the art, various compounds can be used as crosslinkers and / or chain extenders. Similarly, various plasticizers, exemplified by the specific plasticizers described below, can also be used interchangeably or interchangeably as crosslinkers and / or chain extenders of the sealant.

[0179] In some embodiments, the sealant includes a crosslinker. Some examples of suitable crosslinkers include silane crosslinkers having hydrolysable groups or portions or complete hydrolysis products thereof. Examples of such silane crosslinkers include those silane crosslinkers that include silicon compounds having the general formula (XII): 15 C Si(R 16 ) (4-C) where each R 15 is an independently selected monovalent hydrocarbon group, such as an alkyl group; each R 16 is a hydrolysable substituent, for example a halogen atom, an acetamide group, an acyloxy group such as an acetoxy group, an alkoxy group, an amido group, an amino group, an aminooxy group, a hydroxyl group, an oxime group, a ketoxime group, or a methylacetamide group; and subscript C is 0-3, such as 0, 1, 2, or 3. Generally, the average value of subscript C is greater than 2. Alternatively, subscript C can have a range of values from 3 to 4. Generally, each R 16 is independently selected from a hydroxyl group, an alkoxy group, an acetoxy group, an amido group, or an oxime. Specific examples of suitable silane crosslinkers include methyldiacetoxymethoxysilane, methylethacetoxydimethoxysilane, vinyl diacetoxymethoxysilane, vinyl ethacetoxydimethoxysilane, methyldiacetoxylethoxysilane, methylethacetoxydiethoxysilane, and combinations thereof.

[0180] In some embodiments, the crosslinking agent includes acyloxy silanes, alkoxy silanes, ketoximosilanes, oximosilanes, and the like, or combinations thereof.

[0181] Examples of suitable acyloxy silane crosslinking agents include tetraacetoxysilane, organotriacetoxysilanes, diorganodiacetoxysilanes, and combinations thereof. The acyloxy silanes can contain alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, and t-butyl; alkenyl groups such as vinyl, allyl, or hexenyl; aryl groups such as phenyl, tolyl, or xylyl; aralkyl groups such as benzyl or 2-phenylethyl; and fluorinated alkyl groups such as 3,3,3-trifluoropropyl. Exemplary acyloxy silanes include tetraacetoxysilane, methyltriacetoxysilane, ethyltriacetoxysilane, vinyltriacetoxysilane, propyltriacetoxysilane, butyltriacetoxysilane, phenyltriacetoxysilane, octyltriacetoxysilane, dimethyldiacetoxysilane, phenylmethyldiacetoxysilane, vinylmethyldiacetoxysilane, diphenyldiacetoxysilane, tetraacetoxysilane, and combinations thereof. In some embodiments, the crosslinking agent includes organotriacetoxysilanes, for example, a mixture comprising methyltriacetoxysilane and ethyltriacetoxysilane.

[0182] Examples of amino-functional alkoxysilanes suitable for use in or as crosslinking agents are exemplified by H2N(CH2)2Si(OCH3)3, H2N(CH2)2Si(OCH2CH3)3, H2N(CH2)3Si(OCH3)3, H2N(CH2)3Si(OCH2CH3)3, CH3NH(CH2)3Si(OCH3)3, CH3NH(CH2)3Si(OCH2CH3)3, CH3NH(CH2)5Si(OCH3)3, CH3NH(CH2)5Si(OCH2CH3)3, H2N(CH2)2NH(CH2)3Si(OCH3)3, H2N(CH2)2NH(CH2)3Si(OCH2CH3)3, CH3NH(CH2)2NH(CH2)3Si(OCH3)3, CH3NH(CH2)2NH(CH2)3Si(OCH2CH3)3, C4H9NH(CH2)2NH(CH2)3Si(OCH3)3, C4H9NH(CH2)2NH(CH2)3Si(OCH2CH3)3, H2N(CH2)2SiCH3(OCH3)2, H2N(CH2)2SiCH3(OCH2CH3)2, H2N(CH2)3SiCH3(OCH3)2, H2N(CH2)3SiCH3(OCH2CH3)2, CH3NH(CH2)3SiCH3(OCH3)2, CH3NH(CH2)3SiCH3(OCH2CH3)2, CH3NH(CH2)5SiCH3(OCH3)2, CH3NH(CH2)5SiCH3(OCH2CH3)2, H2N(CH2)2NH(CH2)3SiCH3(OCH3)2, H2N(CH2)2NH(CH2)3SiCH3(OCH2CH3)2, CH3NH(CH2)2NH(CH2)3SiCH3(OCH3)2, CH3NH(CH2)2NH(CH2)3SiCH3(OCH2CH3)2, C4H9NH(CH2)2NH(CH2)3SiCH3(OCH3)2, C4H9NH(CH2)2NH(CH2)3SiCH3(OCH2CH3)2, and combinations thereof.

[0183] Examples of suitable oximosilane crosslinkers include alkyltrioximosilanes such as methyltrioximosilane, ethyltrioximosilane, propyltrioximosilane, and butyltrioximosilane; alkoxyltrioximosilanes such as methoxyltrioximosilane, ethoxyltrioximosilane, and propoxyltrioximosilane; or alkenyltrioximosilanes such as propenyltrioximosilane or butenyltrioximosilane; alkenyloximosilanes such as vinyl oximosilane; alkenylalkyldioximosilanes such as vinylmethyldioximosilane, vinyethyl dioximosilane, vinylmethyldioximosilane, or vinyethyl dioximosilane; or combinations thereof.

[0184] Examples of suitable ketoximosilane crosslinkers include methyltris(dimethylketoximo)silane, methyltris(methylethylketoximo)silane, methyltris(methylpropylketoximo)silane, methyltris(methylisobutylketoximo)silane, ethyltris(dimethylketoximo)silane, ethyltris(methylethylketoximo)silane, ethyltris(methylpropylketoximo)silane, ethyltris(methylisobutylketoximo)silane, vinyltris(dimethylketoximo)silane, vinyltris(methylethylketoximo)silane, vinyltris(methylpropylketoximo)silane, vinyltris(methylisobutylketoximo)silane, tetrakis(dimethylketoximo)silane, tetrakis(methylethylketoximo)silane, tetrakis(methylpropylketoximo)silane, tetrakis(methylisobutylketoximo)silane, methylbis(dimethylketoximo)silane, methylbis(cyclohexylketoximo)silane, triethoxy(ethylmethylketoximo)silane, diethoxydi(ethylmethylketoximo)silane, ethoxytris(ethylmethylketoximo)silane, methylvinylbis(methylisobutylketoximo)silane, or combinations thereof.

[0185] In certain embodiments, the crosslinker includes an alkoxysilane, examples of which are dialkoxysilanes such as dialkyldialkoxysilanes; trialkoxysilanes such as alkyltrialkoxysilanes; tetraalkoxysilanes; partial or complete hydrolysis products thereof; or combinations thereof. Examples of suitable trialkoxysilanes include methyltrimethoxysilane, vinyltrimethoxysilane, methyltriethoxysilane, ethyltrimethoxysilane, ethyltriethoxysilane, isobutyltrimethoxysilane, isobutyltriethoxysilane, and combinations thereof. An example of a suitable tetraalkoxysilane includes tetraethoxysilane. In particular embodiments, the crosslinker includes, alternatively, methyltrimethoxysilane.

[0186] In certain embodiments, the crosslinking agent is polymeric. For example, the crosslinking agent can include a dipodal silane such as bis(triethoxysilyl)hexane, 1,4-bis[trimethoxysilyl(ethyl)]benzene, bis[3-(triethoxysilyl)propyl]tetrasulfide, bis(trimethoxysilyl)hexane, bis(triethoxysilyl)ethane, bis(trimethoxysilyl)ethane, and combinations thereof. In these or other embodiments, the crosslinking agent can be one single crosslinking agent or a combination including two or more crosslinking agents that are different from each other, for example, based on hydrolysable substituents and other organic groups bonded to silicon, and when polymeric crosslinking agents are used, based on siloxane units, structure, molecular weight, sequence, etc.

[0187] The amount of crosslinking agent present in the sealant depends on various factors (e.g., the amount and / or type of at least one silicone-polyether copolymer, the type and / or amount of any additional materials present in the sealant such as other polymeric additives, the type of crosslinking agent used, etc.) and can be readily determined by one of skill in the art. Generally, where a crosslinking agent is present, the sealant includes the crosslinking agent in an amount of 0.5 wt% to 15 wt%, alternatively 1 wt% to 10 wt%, alternatively 3 wt% to 10 wt%, based on the weight of the at least one silicone-polyether copolymer.

[0188] In some embodiments, the sealant includes a plasticizer. Examples of suitable plasticizers include organic plasticizers such as organic plasticizers including carboxylate esters (e.g., esters), phthalate esters (e.g., phthalates), carboxylates (e.g., carboxylates), adipate esters (e.g., adipates), or combinations thereof. Specific examples of suitable organic plasticizers include bis(2-ethylhexyl) terephthalate, bis(2-ethylhexyl)-1,4-benzenedicarboxylate, 2-ethylhexyl methyl-1,4-benzenedicarboxylate, 1,2-cyclohexane dicarboxylic acid, dinonyl ester (both branched and linear), bis(2-propylheptyl) phthalate, diisononyl adipate, and combinations thereof.

[0189] In certain embodiments, the plasticizer is an ester having an average of at least one group of the following formula per molecule:

[0190]

[0191] where R 17 represents a hydrogen atom or a monovalent organic group (e.g., a branched or linear monovalent hydrocarbon group such as an alkyl group having 4 to 15 carbon atoms, alternatively 9 to 12 carbon atoms). In these or other embodiments, the plasticizer has an average of at least two groups of the above formula per molecule, each bonded to a carbon atom in the cyclic hydrocarbon. In such cases, the plasticizer can have the general formula:

[0192]

[0193] In this formula, D is a carbocyclic group having 3 or more carbon atoms, alternatively 3 to 15 carbon atoms, which can be unsaturated, saturated, or aromatic. The subscript E is 1 to 12. Each R 18 is independently a branched or straight-chain monovalent hydrocarbon group, such as an alkyl group having 4 to 15 carbon atoms (e.g., an alkyl group such as methyl, ethyl, butyl, and the like). Each R 19 is independently a hydrogen atom or a branched or straight-chain, substituted or unsubstituted monovalent organic group. For example, in some embodiments, at least one R 19 is a moiety comprising an ester functional group.

[0194] In particular embodiments, the sealant comprises a polymeric plasticizer. Examples of polymeric plasticizers include: alkenyl polymers (e.g., those obtained by polymerization of vinyl or allyl monomers by various methods); polyalkylene glycol esters (e.g., diethylene glycol dibenzoate, triethylene glycol, pentaerythritol dibenzoate, and the like); polyester plasticizers (e.g., those obtained from diacids such as sebacic acid, adipic acid, azelaic acid, phthalic acid, and the like with dihydric alcohols such as ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, and the like); polyethers, including polyether polyols each having a molecular weight of no less than 500 (e.g., polyethylene glycol, polypropylene glycol, polytetramethylene glycol, and the like); polystyrenes (e.g., polystyrene, poly-a-methylstyrene, and the like); polybutenes and polybutadienes (e.g., polyisobutylene, butadiene acrylonitrile, and the like); and polychloroprene. In various embodiments, low molecular weight plasticizers and high molecular weight polymeric plasticizers can be present in the sealant in combination.

[0195] Particular plasticizers are known in the art and are commercially available. Such plasticizers can be present in the sealant individually or in combination. For example, the plasticizer can include a phthalate, such as: a dialkyl phthalate, such as dibutyl phthalate (Eastman DBP plasticizer), diheptyl phthalate, diisononyl phthalate, di(2-ethylhexyl) phthalate, or diisodecyl phthalate (DIDP), bis(2-propylheptyl) phthalate (BASF DPHP), di(2-ethylhexyl) phthalate (Eastman DOP plasticizer), dimethyl phthalate (Eastman DMP plasticizer); diethyl phthalate (Eastman DEP plasticizer); and the like. TM DBP plasticizer), diheptyl phthalate, diisononyl phthalate, di(2-ethylhexyl) phthalate, or diisodecyl phthalate (DIDP), bis(2-propylheptyl) phthalate (BASF DPHP), di(2-ethylhexyl) phthalate (Eastman DOP plasticizer), dimethyl phthalate (Eastman DMP plasticizer); diethyl phthalate (Eastman DEP plasticizer); and the like. DBP plasticizer), diheptyl phthalate, diisononyl phthalate, di(2-ethylhexyl) phthalate, or diisodecyl phthalate (DIDP), bis(2-propylheptyl) phthalate (BASF DPHP), di(2-ethylhexyl) phthalate (Eastman DOP plasticizer), dimethyl phthalate (Eastman DMP plasticizer); diethyl phthalate (Eastman DEP plasticizer); and the like. TM DBP plasticizer), diheptyl phthalate, diisononyl phthalate, di(2-ethylhexyl) phthalate, or diisodecyl phthalate (DIDP), bis(2-propylheptyl) phthalate (BASF DPHP), di(2-ethylhexyl) phthalate (Eastman DOP plasticizer), dimethyl phthalate (Eastman DMP plasticizer); diethyl phthalate (Eastman DEP plasticizer); and the like. TM DBP plasticizer), diheptyl phthalate, diisononyl phthalate, di(2-ethylhexyl) phthalate, or diisodecyl phthalate (DIDP), bis(2-propylheptyl) phthalate (BASF DPHP), di(2-ethylhexyl) phthalate (Eastman DOP plasticizer), dimethyl phthalate (Eastman DMP plasticizer); diethyl phthalate (Eastman DEP plasticizer); and the like. TMDINCH® (BASF); 2-ethylhexyl methylester 1,4-benzene dicarboxylate; branched and linear dinonyl 1,2-cyclohexane dicarboxylate (BASF TM 425 plasticizer); dicarboxylic acid esters such as benzyl, C7-C9 linear and branched alkyl esters, 1,2-benzene dicarboxylic acid (Ferro 261 A), 1,2,4-benzene tricarboxylic acid (BASF TOTM-I), bis(2-ethylhexyl)-1,4-benzene dicarboxylate (Eastman TM 168 plasticizer); 2-ethylhexyl methylester 1,4-benzene dicarboxylate; branched and linear dinonyl 1,2-cyclohexane dicarboxylate (BASF DINCH); diisononyl adipate; trimellitate esters such as trioctyl trimellitate (Eastman TM TOTM plasticizer); triethylene glycol bis(2-ethylhexanoate) (Eastman TM TEG-EH plasticizer); glycerol triacetate (Eastman TM glycerol triacetate); non-aromatic diacid esters such as dioctyl adipate, di(2-ethylhexyl) adipate (Eastman TM DOA plasticizer and Eastman TM DOA plasticizer, Kosher), di-2-ethylhexyl adipate (BASF DOA), dioctyl sebacate, dibutyl sebacate, and diisodecyl succinate; aliphatic esters such as butyl oleate and methyl acetyl ricinoleate; phosphoric acid esters such as tricresyl phosphate and tributyl phosphate; chlorinated paraffins; hydrocarbon oils such as alkyl biphenyls and partially hydrogenated terphenyls; process oils; epoxy plasticizers such as epoxidized soybean oil and benzyl epoxy stearate; tris(2-ethylhexyl) ester; fatty acid esters; and combinations thereof. Examples of other suitable plasticizers and their commercial sources include BASF 652 and Eastman 168Xtreme TM plasticizer.

[0196] The amount of plasticizer present in the sealant depends on various factors (e.g., the amount and / or type of at least one silicone-polyether copolymer, the type and / or amount of any additional materials present in the sealant such as other polymeric additives, the type of crosslinker used, etc.) and can be readily determined by one skilled in the art. Generally, where a plasticizer is present, the sealant comprises the plasticizer in an amount of 5 to 150 parts by weight based on the combined weight of all components in the sealant. In particular embodiments, the sealant comprises the plasticizer in an amount of 0.1 to 10 weight percent based on the total weight of the sealant.

[0197] In some embodiments, the sealant comprises an extender. Examples of suitable extenders include non-functional polyorganosiloxanes such as those comprising bifunctional units of the formula R 20 2SiO 2 / 2 and terminal units of the formula R 21 3SiD’- where each R 20 and each R 21 is independently a monovalent organic group such as a monovalent hydrocarbon group exemplified by alkyl groups such as methyl, ethyl, propyl, and butyl; alkenyl groups such as vinyl, allyl, and hexenyl; aryl groups such as phenyl, tolyl, xylyl, and naphthyl; and aralkyl groups such as phenethyl; and D’ is an oxygen atom or a divalent group. Non-functionalized polyorganosiloxanes are known in the art and are commercially available. Suitable non-functionalized polyorganosiloxanes are exemplified by, but not limited to, polydimethylsiloxanes. Such polydimethylsiloxanes include 200 fluid, which is commercially available from Dow Silicones Corporation, Midland, Mich., U.S.A., and can have a viscosity in the range of 5 x 10 -5 m 2 / s to 0.1 m 2 / s, alternatively 5 x 10 -5 m 2 / s to 0.05 m 2 / s, and alternatively 0.0125 m 2 / s to 0.06 m 2 / s. The amount of extender present in the sealant depends on various factors (e.g., the amount and / or type of at least one silicone-polyether copolymer, the type and / or amount of any additional materials present in the sealant such as other polymeric additives, the type of crosslinker used, etc.) and can be readily determined by one skilled in the art. Generally, where an extender is present, the sealant comprises the extender in an amount ranging from 0.1 wt% to 10 wt% based on the total weight of the sealant.

[0198] In some embodiments, the sealant comprises an endblocker. Suitable endblockers comprise M units, i.e., siloxane units of the formula R 22 3SiO 1 / 2 where each R 22independently represent a monovalent organic group, such as a monovalent hydrocarbon group. General examples of such endcappers include those comprising a polyorganosiloxane (e.g., a polydiorganosiloxane such as a polydimethylsiloxane) that is terminated at one end by a triorganosilyl group, e.g., (CH3)3SiO-, and terminated at the other end by a hydroxyl group. Other examples of suitable endcappers include polydiorganosiloxanes having both hydroxyl end groups and triorganosilyl end groups, such as those in which more than 50%, alternatively more than 75%, of the total end groups are hydroxyl groups. The amount of triorganosilyl present in such endcappers can vary, and is generally used to adjust the modulus of the reaction product prepared by the condensation reaction of the sealant. Without wishing to be bound by theory, it is believed that higher concentrations of triorganosilyl end groups can provide lower modulus in certain cured products. In some embodiments, the endcapper of the sealant comprises a single endcapping compound. However, in other embodiments, the endcapper of the sealant comprises two or more different endcapping compounds, e.g., that differ from one another in properties including structure, viscosity, average molecular weight, polymer units, sequence, etc., or combinations thereof. The amount of endcapper present in the sealant depends on various factors (e.g., the amount and / or type of at least one silicone-polyether copolymer, the type and / or amount of any additional materials (such as other polymeric additives) present in the sealant, the type of endcapper used, etc.), and can be readily determined by one skilled in the art. Generally, in the presence of an endcapper, the sealant comprises the endcapper in an amount of 0 wt% to 50 wt%, alternatively 0 wt% to 30 wt%, alternatively 0 wt% to 15 wt%, based on the total weight of the at least one silicone-polyether copolymer.

[0199] In certain embodiments, the sealant comprises a surface modifier. Suitable surface modifiers include adhesion promoters, release agents, and the like, as well as combinations thereof. Generally, a surface modifier is used to alter the surface appearance of the reaction product of the sealant. For example, a surface modifier can be used to increase the surface gloss of such reaction products. Specific examples of suitable surface modifiers include polydiorganosiloxanes having alkyl and aryl groups. For example, 550The fluid is a trimethylsiloxy-terminated poly(dimethyl / methylphenyl)siloxane commercially available from Dow Silicones Corporation having a viscosity of 0.000125 m 2 / s. These and other examples of suitable surface modifiers include natural oils (e.g., those obtained from plant or animal sources), such as linseed oil, tung oil, soybean oil, castor oil, fish oil, hempseed oil, cottonseed oil, oiticica oil, rapeseed oil, and the like, as well as combinations thereof.

[0200] In some embodiments, the surface modification agent is an adhesion promoter. Suitable adhesion promoters can include hydrocarbyloxysilanes such as alkoxysilanes, combinations of alkoxysilanes and hydroxy-functional polyorganosiloxanes, amino-functional silanes, epoxy-functional silanes, mercapto-functional silanes, or combinations thereof. Adhesion promoters are known in the art and can include silanes having the formula R 23 F R 24 G Si(OR 25 ) 4-(F+G) where each R 23 is independently a monovalent organic group having at least 3 carbon atoms; R 24 contains at least one SiC-bonded substituent having an adhesion-promoting group such as an amino, epoxy, mercapto, or acrylate group; each R 25 is independently a monovalent organic group (e.g., methyl, ethyl, propyl, butyl, etc.); the subscript F has a value ranging from 0 to 2; the subscript G is 1 or 2; and the sum of (F + G) is no greater than 3. In certain embodiments, the adhesion promoter includes a partial condensate of the silane described above. In these or other embodiments, the adhesion promoter includes a combination of an alkoxysilane and a hydroxy-functional polyorganosiloxane.

[0201] In some embodiments, the adhesion promoter includes an unsaturated compound or an epoxy-functional compound. In such embodiments, the adhesion promoter can be or include an unsaturated or epoxy-functional alkoxysilane such as those having the formula (XIII): 26 H Si(OR 27 ) (4-H) where the subscript H is 1, 2, or 3, alternatively the subscript H is 1. Each R 26 is independently a monovalent organic group, with the proviso that at least one R 26 is an unsaturated organic group or an epoxy-functional organic group. Epoxy-functional organic groups for R 26 are exemplified by 3-glycidyloxypropyl and (epoxy cyclohexyl)ethyl. Unsaturated organic groups for R 26 are exemplified by 3-methacryloyloxypropyl, 3-acryloyloxypropyl, and unsaturated monovalent hydrocarbon groups such as vinyl, allyl, hexenyl, undecenyl. Each R 27 is independently a saturated hydrocarbon group having 1 to 4 carbon atoms, alternatively 1 to 2 carbon atoms. R 27 is exemplified by methyl, ethyl, propyl, and butyl.

[0202] Specific examples of suitable epoxy-functional alkoxysilanes include 3- glycidyloxypropyltrimethoxysilane, 3-glycidyloxypropyltriethoxysilane, (epoxycyclohexyl)ethyldimethoxysilane, (epoxycyclohexyl)ethyldiethoxysilane, and combinations thereof. Examples of suitable unsaturated alkoxysilanes include vinyltrimethoxysilane, allyltrimethoxysilane, allyltriethoxysilane, hexenyltrimethoxysilane, undecylenyltrimethoxysilane, 3-methacryloyloxypropyltrimethoxysilane, 3-methacryloyloxypropyltriethoxysilane, 3-acryloyloxypropyltrimethoxysilane, 3-acryloyloxypropyltriethoxysilane, and combinations thereof.

[0203] In some embodiments, the adhesion promoter includes an epoxy-functional siloxane, such as a reaction product of a hydroxyl-terminated polyorganosiloxane and an epoxy-functional alkoxysilane (e.g., one of the alkoxysilanes described above), or a physical blend of a hydroxyl-terminated polyorganosiloxane and an epoxy-functional alkoxysilane. The adhesion promoter can include a combination of an epoxy-functional alkoxysilane and an epoxy-functional siloxane. For example, examples of adhesion promoters include a mixture of 3-glycidyloxypropyltrimethoxysilane and a reaction product of a hydroxyl-terminated methylvinylsiloxane and 3-glycidyloxypropyltrimethoxysilane, or a mixture of 3-glycidyloxypropyltrimethoxysilane and a hydroxyl-terminated methylvinylsiloxane, or a mixture of 3-glycidyloxypropyltrimethoxysilane and a hydroxyl-terminated methylvinyl / dimethylsiloxane copolymer.

[0204] In certain embodiments, the adhesion promoter includes an aminofunctional silane, such as the aminofunctional alkoxysilanes exemplified by H2N(CH2)2Si(OCH3)3, H2N(CH2)2Si(OCH2CH3)3, H2N(CH2)3Si(OCH3)3, H2N(CH2)3Si(OCH2CH3)3, CH3NH(CH2)3Si(OCH3)3, CH3NH(CH2)3Si(OCH2CH3)3, CH3NH(CH2)5Si(OCH3)3, CH3NH(CH2)5Si(OCH2CH3)3, H2N(CH2)2NH(CH2)3Si(OCH3)3, H2N(CH2)2NH(CH2)3Si(OCH2CH3)3, CH3NH(CH2)2NH(CH2)3Si(OCH3)3, CH3NH(CH2)2NH(CH2)3Si(OCH2CH3)3, C4H9NH(CH2)2NH(CH2)3Si(OCH3)3, C4H9NH(CH2)2NH(CH2)3Si(OCH2CH3)3, H2N(CH2)2SiCH3(OCH3)2, H2N(CH2)2SiCH3(OCH2CH3)2, H2N(CH2)3SiCH3(OCH3)2, H2N(CH2)3SiCH3(OCH2CH3)2, CH3NH(CH2)3SiCH3(OCH3)2, CH3NH(CH2)3SiCH3(OCH2CH3)2, CH3NH(CH2)5SiCH3(OCH3)2, CH3NH(CH2)5SiCH3(OCH2CH3)2, H2N(CH2)2NH(CH2)3SiCH3(OCH3)2, H2N(CH2)2NH(CH2)3SiCH3(OCH2CH3)2, CH3NH(CH2)2NH(CH2)3SiCH3(OCH3)2, CH3NH(CH2)2NH(CH2)3SiCH3(OCH2CH3)2, C4H9NH(CH2)2NH(CH2)3SiCH3(OCH3)2, C4H9NH(CH2)2NH(CH2)3SiCH3(OCH2CH3)2, N-(3-(trimethoxysilyl)propyl)ethylenediamine, and the like, and combinations thereof. In these or other embodiments, the adhesion promoter includes a mercaptofunctional alkoxysilane, such as 3-mercaptopropyltrimethoxysilane or 3-mercaptopropyltriethoxysilane.

[0205] Additional examples of surface-modifying agents include adhesion promoters that are reaction products of an epoxy alkyl alkoxysilane (such as 3-glycidoxypropyltrimethoxysilane) with an amino-substituted alkoxysilane (such as 3- aminopropyltrimethoxysilane), optionally with an alkyl alkoxysilane (such as methyltrimethoxysilane).

[0206] In some embodiments, the surface-modifying agent includes, alternatively is, a release agent. Suitable release agents are exemplified by fluorinated compounds (such as fluorofunctional silicones or fluorofunctional organic compounds). In particular embodiments, the sealant includes multiple surface-modifying agents, such as one or more adhesion promoters, one or more release agents, one or more natural oils, or combinations thereof.

[0207] The amount of surface-modifying agent present in the sealant depends on various factors (e.g., the amount and / or type of at least one silicone-polyether copolymer, the type and / or amount of any additional materials present in the sealant, the curing conditions to which the sealant is intended to be exposed, etc.) and can be readily determined by one of skill in the art. Generally, where a surface-modifying agent is present, the sealant includes the surface-modifying agent in an amount of 0.01 parts by weight to 50 parts by weight, alternatively 0.01 parts by weight to 10 parts by weight, alternatively 0.01 parts by weight to 5 parts by weight, based on the combined weight of all components in the sealant.

[0208] In certain embodiments, the sealant includes a desiccant, such as a physical desiccant (e.g., a sorbent), a chemical desiccant, or the like. Generally, the desiccant binds water and low molecular weight alcohols from various sources. For example, the desiccant can bind byproducts of condensation reactions involving at least one silicone-polyether copolymer, such as water and alcohols. Physical desiccants generally capture and / or adsorb such water and / or byproducts, whereas chemical desiccants generally bind water and / or other byproducts through chemical means (e.g., through covalent bonding). Examples of suitable desiccants for use in the sealant include sorbents, such as sorbents including inorganic particles. Such sorbents generally have a particle size of 10 micrometers or less, alternatively 5 micrometers or less, and an average pore size sufficient to adsorb water and low molecular weight alcohols (e.g., 10 angstroms (A) or less, alternatively 5 A or less, alternatively 2 A or less, alternatively 1 A or less, alternatively 0.5 A or less, alternatively 0.1 A or less, or the like). Particular examples of such sorbents include zeolites (e.g., chabazite, mordenite, and offretite) and molecular sieves including alkali metal aluminosilicates, silica gels, silica-magnesia gels, activated carbons, activated alumina, calcium oxide, and combinations thereof. Examples of commercially available desiccants include dry molecular sieves, such as those available from Grace Davidson under the trademark (angstroms) or less, alternatively or less, alternatively or less, alternatively sold under the trade designation PURMOL by Zeochem, Louisville, Ky., U.S.A. (angstrom) molecular sieves, and ZEOLITE 4A molecular sieves sold under the trade designation Doucil by Ineos Silicas, Warrington, England Other examples of suitable desiccants include MOLSIV adsorbent types 13X, 3A, 4A, and 5A molecular sieves, all of which are commercially available from UOP, Illinois, U.S.A.; SILIPORITE NK 30AP and 65xP molecular sieves from Atofina, Philadelphia, Pa., U.S.A.; and molecular sieves available from W. R. Grace, Maryland, U.S.A., under various names. Examples of chemical desiccants include silanes such as those described above with respect to crosslinking agents. For example, alkoxysilanes suitable as desiccants include vinyltrimethoxysilane, vinyltriethoxysilane, and combinations thereof. As will be appreciated by one skilled in the art, a chemical desiccant can be added to the sealant or to a portion of the sealant (e.g., in the case where the sealant is a multi-part composition) to keep the sealant or the portion thereof free of water. As such, a desiccant can be added to a portion of the sealant (e.g., a dry portion) prior to forming the sealant, thereby stabilizing the architecture of the portion. Alternatively or additionally, a desiccant can keep the sealant free of water after formulation (e.g., after the portions of the sealant are combined / mixed together). The amount of desiccant present in the sealant depends on various factors (e.g., the amount and / or type of at least one silicone-polyether copolymer, the type and / or amount of any additional materials present in the sealant, the curing conditions to which the sealant is intended to be exposed, etc.) and can be readily determined by one skilled in the art. Generally, where a desiccant is present, the sealant comprises the desiccant in an amount of 0.1 parts by weight to 5 parts by weight, based on the combined weight of all components in the sealant.

[0209] In some embodiments, the sealant contains a biocide. General examples of suitable biocides include fungicides, herbicides, insecticides, antimicrobials, and combinations thereof. For example, in some embodiments, the biocide includes, alternatively, a fungicide. Specific examples of fungicides include N-substituted benzimidazole carbamates and benzimidazole carbamates, such as methyl 2-benzimidazole carbamate, ethyl 2-benzimidazole carbamate, isopropyl 2-benzimidazole carbamate, methyl N-{2-[1-(N,N-dimethylcarbamoyl)benzimidazole]} carbamate, methyl N-{2-[1-(N,N-dimethylcarbamoyl)-6-methylbenzimidazole]} carbamate, methyl N-{2-[1-(N,N-dimethylcarbamoyl)-5-methylbenzimidazole]} carbamate, and methyl N-{2-[1-(N-methylcarbamoyl)benzimidazole]} carbamate. Methyl carbamate, N-{2-[1-(N-methylcarbamoyl)-6-methylbenzimidazolyl]} carbamate, N-{2-[1-(N-methylcarbamoyl)-5-methylbenzimidazolyl]} carbamate, N-{2-[1-(N,N-dimethylcarbamoyl)benzimidazolyl]} carbamate, N-{2-[2-(N-methylcarbamoyl)benzimidazolyl]} carbamate, N-{2-[1-(N,N-dimethylcarbamoyl)-6-methylbenzimidazolyl]} carbamate, N-{2-[1-(N-methylcarbamoyl)-6-methylbenzimidazolyl]} carbamate, N- Isopropyl carbamate, N-{2-[1-(N,N-dimethylcarbamoyl)benzimidazolyl]}carbamate, Methyl carbamate, N-{2-[1-(N-methylcarbamoyl)benzimidazolyl]}carbamate, Methyl carbamate, N-{2-[1-(N-propylcarbamoyl)benzimidazolyl]}carbamate, methoxyethyl carbamate, N-{2-[1-(N-butylcarbamoyl)benzimidazolyl]}carbamate, methoxyethyl carbamate, N-{2-[1-(N-butylcarbamoyl)benzimidazolyl]}carbamate, N-{2-[1-(N-butylcarbamoyl)benzimidazolyl]}carbamate, methoxyethyl carbamate, N-{2-[1-(N-propyl ... ]} ethoxyethyl carbamate, N-{2-[1-(N-butylcarbamoyl)benzimidazolyl]} ethoxyethyl carbamate, N-{1-(N,N-dimethylcarbamoyloxy)benzimidazolyl]} methyl carbamate, N-{2-[N-methylcarbamoyloxy)benzimidazolyl]} methyl carbamate, N-{2-[1-(N-butylcarbamoyloxy)benzimidazolyl]} methyl carbamate, N-{2-[1-(N-propylcarbamoyl)benzimidazolyl]} ethoxyethyl carbamate, N-{2-[1-(N-butylcarbamoyloxy)benzimidazolyl]} ethoxyethyl carbamate, N-{2-[1-(N,N-dimethyl ...Methyl N-{2-[1-(N,N-dimethylcarbamoyl)-6-chlorobenzimidazolyl]}carbamate and methyl N-{2-[1-(N,N-dimethylcarbamoyl)-6-nitrobenzimidazolyl]}carbamate; 10,10'-Oxobisphenoxarsine (Trade name: Vinyzene, OBPA); Diiodomethyl-p-tolylsulfone; Benzo-thiophene-2-cyclohexylcarboxamide-S,S-dioxide; N-(Fluorodichloromethylthio)phthalimide (Trade name: Fluor-Folper, Preventol A3); Methyl-benzimidazole-2-ylcarbamate (Trade name: Carbendazim, Preventol BCM); Zinc-bis(2-pyridinethio-1-oxide); Zinc pyrithione; 2-(4-Thiazolyl)-benzimidazole; N-Phenyl-iodoallylcarbamate; N-Octyl-4-isothiazolin-3-one; 4,5-Dichloride-2-n-octyl-4-isothiazolin-3-one; n-Butyl-1,2-benzisothiazolin-3-one; Triazolyl compounds such as tebuconazole; and the like, and combinations thereof. In particular embodiments, such fungicides are used in combination with one or more inorganic materials such as minerals (e.g., zeolites), metals (e.g., copper, silver, platinum, and the like), and combinations thereof.

[0210] In particular embodiments, the biocide includes, alternatively, a herbicide. Particular examples of herbicides include amide herbicides such as butachlor N,N-diallyl-2-chloroacetamide; CDEA 2-chloro-N,N-diethylacetamide; benoxacor (RS)-2-[5-(2,4-dichlorophenoxy)-2-nitrophenoxy]-N- ethylpropionamide; anilide herbicides such as pyroxasulfone cis-2,5-dimethylpyrrolidine-1- formanilide; fluoroglycofen-ethyl 4'-fluoro-N-isopropyl-2-[5-(trifluoromethyl)-1,3,4- thiazol-2-yloxy]acetanilide; naproanilide (RS)-a-2-naphthyloxypropanamidebenzene; arylalanine herbicides such as clacyfos N-benzoyl-N-(3,4-dichlorophenyl)-DL-alanine; flufenacet N-benzoyl-N-(3-chloro-4-fluorophenyl)-D-alanine; chloroacetanilide herbicides such as butylate N-butoxymethyl-2-chloro-2',6'-diethylacetanilide; cafenstrole 2-chloro-N-(pyrazol-1-ylmethyl)acetanilide-2',6'-dimethyl; propanil (RS)-2-chloro-N-(1-methylprop-2-ynyl)acetanilide; sulfonyl anilide herbicides such as clomazone 3-chloro-2-(5-ethoxy-7-fluoro[1,2,4]triazolo[1,5-c]pyrimidin-2- ylsulfonamido)benzoic acid; metosulam 2',6'-dichloro-5,7-dimethoxy-3'-methyl[1,2,4]triazolo[1,5- a]pyrimidine-2-sulfonanilide; antibiotic herbicides such as bialaphos 4-[hydroxy(methyl)phosphono]-L-homoalaninyl-L-alaninyl-L-alanine; benzoic acid herbicides such as chloramben 3-amino-2,5-dichlorobenzoic acid; 2,3,6-TBA 2,3,6-trichlorobenzoic acid; pyrimidinyloxybenzoic acid herbicides such as bifenox 2,6-bis(4,6-dimethoxypyrimidin-2-yloxy)benzoic acid; pyrimidinylthiobenzoic acid herbicides such as pyrithiobac-acid 2-chloro-6-(4,6-dimethoxypyrimidin-2- ylthio)benzoic acid; phthalic acid herbicides such as chlorthal-dimethyl tetra-chloro-p- phthalic acid; picolinic acid herbicides such as aminopyralid 4-amino-3,6-dichloropyridine-2- carboxylic acid; quinolinecarboxylic acid herbicides such as quinclorac 3,7-dichloroquinoline-8- carboxylic acid; arsenic-containing herbicides such as CMA calcium bis(hydroxymethylarsonate); MAMA ammonium hydroxymethylarsonate; sodium arsenite; benzoylcyclohexanedione herbicides such as mesotrione 2-(4-methylsulfonyl-2-nitrobenzoyl)cyclohexane-1,3-dione; benzofuranylalkylsulfonate herbicides such as furilazole 2,3-dihydro-3,3-dimethylbenzofuran-5- ylethane sulfonate; carbamate herbicides such as tufoxuron 5-tert-butyl-1,2-oxazol-3- ylcarbamic acid methyl ester; carfentrazone-ethyl 4-[2-(4-chloro-o-tolyloxy)ethanoyl- amino]phenylsulfonylcarbamic acid methyl ester;benzeneaminocarboxylate herbicides such as BCPC (RS)-sec-butyl 3-chlorobenzeneaminocarboxylate; phenmedipham ethyl 3-phenylaminocarbamoyloxyphenylaminocarboxylate; swep 3,4-dichlorophenylaminocarboxylate; cyclohexenone herbicides such as butafenacil (RS)-(EZ)-5-(3-butyryl-2,4,6-trimethylphenyl)-2-(1-ethoxyiminopropyl)-3- hydroxycyclohex-2-en-1-one; dimethachlone (RS)-(EZ)-2-{1-[(2E)-3-chloroallyloxyimino]propyl}-3- hydroxy-5-perhydropyranyl-4-ylcyclohex-2-en-1-one; cyclopropylisoxazole herbicides such as isoxachlortole 4-chloro-2-methylsulfonylphenyl 5-cyclopropyl-1,2-oxazol-4-yl ketone; dicarboximide herbicides such as dithiopyr 2-methyl-4-(α,α,α-trifluoro-m-tolyl)-1,2,4-oxadiazine-3,5-dione; dinitroaniline herbicides such as benefin N-ethyl-α,α,α-trifluoro-N-(2-methylallyl)-2,6-dinitro-p-toluidine; prodiamine 5-dipropylamino-α,α,α-trifluoro-4,6-dinitro-o-toluidine; dinitrophenol herbicides such as nitropanol 4,6-dinitro-o-cymen-3-ol; dinoseb α-ethoxy-4,6-dinitro-o-methylphenol; diphenyl ether herbicides such as fluometuron O-[2-chloro-5-(2-chloro-α,α,α-trifluoro-p-tolyloxy)benzoyl]-L-lactic acid; nitrophenyl ether herbicides such as bifenox 2-chloro-6-nitro-3-phenoxyaniline; chlorenvinphos 2,4-dichlorophenyl 4-nitrophenyl ether; dithiocarbamate herbicides such as thiram 3,5-dimethyl-1,3,5-thiadiazine-2-thione; halogenated aliphatic herbicides such as dichlobenil 2,2-dichloropropionic acid; chloroacetic acid; imidazolinone herbicides such as imazapyr (RS)-2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)nicotinic acid; inorganic herbicides such as disodium tetraborate decahydrate; sodium azide; nitrile herbicides such as bromofenoxim 3,5-dichloro-4-hydroxy-benzonitrile; iodobonrile 4-hydroxy-3,5-di-iodobenzonitrile; organophosphorus herbicides such as anilofos O,O-dimethyl dithiophosphoric acid S-4-chloro-N-isopropylbenzoyl methyl ester; glufosinate 4-[hydroxy(methyl)phosphinoyl]-DL-homoalanine; phenoxy herbicides such as clomazone (RS)-2-(2,4-dichloro-m-tolyloxy)propionoanilide; dichlofluanid 2-(2,4,5-trichlorophenoxy)ethanol; phenoxyacetic herbicides such as MCPA (4-chloro-2-methylphenoxy)acetic acid; phenoxybutyric herbicides such as MCPB 4-(4-chloro-o-tolyloxy)butyric acid; phenoxypropionic herbicides such as triclopyr (RS)-2-(2,4,5-trichlorophenoxy)propionic acid;aryloxyphenoxypropionic herbicides such as clomazone (RS)-2-[2-[4-(3,5-dichloro-2- pyridinyloxy)phenoxy]propionyl]isoxazolidine; phenylenediamine herbicides such as dinitramine N1,N1-diethyl-2,6-dinitro-4-trifluoromethyl-m-phenylenediamine; pyrazolyloxyacetophenone herbicides such as benzofluor 2-[4-(2,4-dichlorobenzoyl)-1,3-dimethylpyrazol-5-yloxy]acetophenone; pyrazolylphenyl herbicides such as pyraflufen-ethyl 2-chloro-5-(4-chloro-5-difluoromethoxy-1- methylpyrazol-3-yl)-4-fluorophenoxyacetic acid; pyridazin herbicides such as anisuron 6-chloro-3-phenylpyridazin-4-ol; pyridazinone herbicides such as chloridazon 5-amino-4-chloro-2-phenylpyridazin-3(2H)-one; flufenpyr 5-bromo-1,6-dihydro-6-oxo-1- phenylpyridazin-4-ylaminooxyacetic acid; pyridine herbicides such as fluroxypyr 4-amino-3,5- dichloro-6-fluoro-2-pyridinyloxyacetic acid; thiazopyr-methyl 2-difluoromethyl-5-(4,5-dihydro-1,3- thiazol-2-yl)-4-isobutyl-6-trifluoromethyl-nicotinic acid ester; pyrimidinediamine herbicides such as butachlor 6-chloro-N4-isopropylpyrimidine-2,4-diamine; quaternary ammonium herbicides such as diquat 1,1'-dimethyl-4,4'-bipyridinium; paraquat 1,1'-dimethyl-4,4'-bipyridinium; thio- carbamate herbicides such as butylate S-cyclohexyl(ethyl)thiocarbamic acid ethyl ester; secbumeton S-di-sec-butylthiocarbamic acid benzyl ester; thio-carbonate herbicides such as EXD O,O-diethyldithiobis(thiocarbonic acid ester); thiourea herbicides such as diphenamid 1,1-dimethyl-3-m-tolyl-2-thiourea; triazine herbicides such as triaziflan (RS)-N-[2-(3,5-dimethylphenoxy)-1-methylethyl]-6-(1-fluoro-1-methylethyl)-1,3,5- triazine-2,4-diamine; chlorotriazine herbicides such as cyprazine 6-chloro-N2-cyclopropyl-N4- isopropyl-1,3,5-triazine-2,4-diamine; prometon 6-chloro-A2,N4-diisopropyl-1,3,5-triazine-2,4- diamine; methoxytriazine herbicides such as prometryn N2,N4-diisopropyl-6-methoxy-1,3,5-triazine- 2,4-diamine; methylthiotriazine herbicides such as cyanazine 2-(4-ethylamino-6-methylthio-1,3,5- triazin-2-ylamino)-2-methylpropionitrile; triazinone herbicides such as hexazinone 3-cyclohexyl-6- dimethylamino-1-methyl-1,3,5-triazine-2,4(1H,3H)-dione; triazole herbicides such as aziprotryn N- ethyl-N-propyl-3-propylsulfonyl-1H-1,2,4-triazole-1-carboxamide;triazolinone herbicides such as pentoxazone (RS)-2-chloro-3-{2-chloro-5-[4- (difluoromethyl)-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl]-4-fluorophenyl} propanoic acid; triazolopyrimidine herbicides such as florasulam 2',6',8-trifluoro-5- methoxy[1,2,4]triazolo[1,5-c]pyrimidine-2-sulfonanilide; uracil herbicides such as flupropacil isopropyl 2-chloro-5-(1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4- trifluoromethylpyrimidin-1-yl)benzoate; urea herbicides such as dymron 3-cyclooctyl- 1,1-dimethylurea; dimeuron 1-(5-tert-butyl-1,2-oxazol-3-yl)-3-methylurea; phenylurea herbicides such as chloreturon 3-[4-(4-chlorophenoxy)phenyl]-1,1-dimethylurea; cycluron 1-(2-methylcyclohexyl)-3-phenylurea; pyrimidinylsulfonylurea herbicides such as cloransulam 1-(4,6-dimethoxy-pyrimidin-2-yl)-3-(3-trifluoromethyl-2-pyridinylsulfonyl)urea; metazachlor 5-[(4,6-dimethoxy-pyrimidin-2-ylcarbamoyl)sulfamoyl]-1-methylpyrazole-4- carboxylic acid; triazinylsulfonylurea herbicides such as thiazopyr 3-(4-methoxy-6- methyl-1,3,5-triazin-2-ylcarbamoylsulfamoyl)thiophene-2-carboxylic acid; thiadiazolylurea herbicides such as tetrafluron 1-(5-tert-butyl-1,3,4-thiadiazol-2-yl)-1,3- dimethylurea; and / or unclassified herbicides such as vallex (2,3,6-trichlorophenyl) acetic acid; benoxacor 2-(3,4-dichlorophenyl)-4-methyl-1,2,4-oxadiazoline-3,5-dione; dimethachlor (RS)-1-(2,3,6-trichlorobenzyloxy)propan-2-ol; 2,4-D, chlorimuron-ethyl, and fenoxaprop-ethyl; and the like, and combinations thereof.

[0211] In some embodiments, the biocide comprises, alternatively, a pesticide. General examples of pesticides include insect repellents such as N,N-diethyl-m-toluamide; and pyrethroids such as permethrin. Specific examples of pesticides include atrazine, diazinon, and chlorpyrifos. In these or other embodiments, the biocide comprises, alternatively, an antimicrobial agent. The type and nature of the antimicrobial agent can vary and can be readily determined by one skilled in the art. Specific antimicrobial agents are commercially available and include 5700 and 5772, which are available from Dow Silicones Corporation, Midland, Mich., U.S.A. In certain embodiments, the biocide includes (alternatively is) a boron-containing material, such as an anhydride, borax, or disodium octaborate tetrahydrate. In various embodiments, the sealant comprises two or more biocides each selected from the fungicides, herbicides, insecticides, antimicrobial agents, and other biocidal components exemplified herein.

[0212] The amount of biocide present in the sealant depends on various factors (e.g., the type(s) of biocide(s) used, the amount and / or type of at least one silicone-polyether copolymer, the intended use of the sealant, the curing conditions to which the sealant is intended to be exposed, etc.), and can be readily determined by one of skill in the art. Generally, where a biocide is present, the sealant comprises the biocide or combination of biocides in an amount of 0.01 wt% to 10 wt%, alternatively 0.1 wt% to 5 wt%, based on the total weight of the sealant.

[0213] In certain embodiments, the sealant comprises a flame retardant. Examples of suitable flame retardants include organic / carbonaceous flame retardants (e.g., carbon black, etc.), inorganic / mineral-based flame retardants (e.g., hydrated aluminum hydroxide, silicates such as wollastonite, metal complexes of platinum, and / or platinum, etc.), and the like, as well as combinations thereof. Additional examples of suitable flame retardants include halogen-based flame retardants such as decabromodiphenyl ether, octabromodiphenyl ether, hexabromocyclododecane, decabromodiphenyl ether, diphenyoxybenzene, ethylene-bis-tetrachlorophthalimide, pentabromoethylbenzene, pentabromobenzyl acrylate, tribromophenyl maleimide, tetrabromobisphenol A, bis-(tribromophenoxy)ethane, bis-(pentabromophenoxy)ethane, polydibromophenylene oxide, tribromophenyl allyl ether, bis-dibromopropyl ether, tetrabromophthalic anhydride, dibromoneopentyl glycol, dibromoethyl dibromocyclohexane, pentabromodiphenyl ether, tribromostyrene, pentabromochlorocyclohexane, tetra- bromo-xylene, hexabromocyclododecane, brominated polystyrene, tetradecabromodiphenoxybenzene, trifluropropylene, and PVC; phosphorus-based flame retardants such as phosphoric acid (2,3-dibromopropyl) ester, phosphorus, cyclic phosphates, triaryl phosphates, bis-melaminium pentate, dipentaerythritol dicyclophosphate, dimethyl methyl phosphate, phosphine oxide diols, triphenyl phosphate, tri-(2-chloroethyl) phosphate, phosphates such as tricresyl phosphate, trixylyl phosphate, isodecyl diphenyl phosphate, ethylhexyl diphenyl phosphate, trioctyl phosphate, tributyl phosphate, and tributoxyethyl phosphate, and phosphates of various amines (e.g., ammonium phosphates); tetraalkyl lead compounds such as tetraethyl lead; iron pentacarbonyl; methylcyclopentadienyl manganese tricarbonyl; melamine and its derivatives such as melamine salts; guanidine; dicyandiamide; ammonium sulfamate; aluminum hydroxide; magnesium hydroxide aluminum hydroxide; and the like, as well as derivatives, modifications, and combinations thereof. The amount of flame retardant present in the sealant depends on various factors (e.g., the amount and / or type of at least one silicone-polyether copolymer, the intended use of the sealant, the curing conditions to which the sealant is intended to be exposed, etc., the presence / absence of a vehicle / solvent, etc.), and can be readily determined by one skilled in the art. Generally, where a flame retardant is present, the sealant comprises the flame retardant in an amount of 0.01 wt% to 15 wt%, alternatively 0.1 wt% to 10 wt%, based on the total weight of the sealant.

[0214] In certain embodiments, the sealant comprises a binder. Generally, the binder is a non-reactive elastomeric organic polymer, i.e., an elastomeric organic polymer that does not react with the at least one silicone-polyether copolymer. Additionally, the binder is generally compatible with the at least one silicone-polyether copolymer, i.e., the binder does not form a two-phase system when formulated with the at least one silicone-polyether copolymer into a sealant. Generally, suitable binders have low air and moisture permeability, and generally have a number average molecular weight (Mn) of 30,000 to 75,000. However, the binder can comprise a blend of various non-reactive elastomeric organic polymers (e.g., a blend of such polymers having a high molecular weight with those having a low molecular weight). In such cases, the higher molecular weight polymers generally have an Mn of 100,000 to 600,000, while the lower molecular weight polymers generally have an Mn of 900 to 10,000, alternatively 900 to 3,000. As understood by one skilled in the art, the lower end of the Mn range is generally selected such that the binder is compatible with the at least one silicone-polyether copolymer and other ingredients of the sealant. The binder can comprise or alternatively can be one non-reactive elastomeric organic polymer, or alternatively can comprise two or more non-reactive elastomeric organic polymers that differ from one another in structure, viscosity, average molecular weight (Mn or Mw), polymer units, sequence, or the like, or combinations thereof.

[0215] Examples of suitable binders include polyisobutylenes known in the art and commercially available. Specific examples of polyisobutylenes include those sold by BASF Corporation, Germany under the trademark Oppanol® and various grades of hydrogenated polyisobutylenes sold by NOF Corp., Japan under the trademark NOF-Plastol®. Examples of suitable binders include polyisobutylenes known in the art and commercially available. Specific examples of polyisobutylenes include those sold by BASF Corporation, Germany under the trademark Oppanol® and various grades of hydrogenated polyisobutylenes sold by NOF Corp., Japan under the trademark NOF-Plastol®. Examples of suitable binders include polyisobutylenes known in the art and commercially available. Specific examples of polyisobutylenes include those sold by BASF Corporation, Germany under the trademark Oppanol® and various grades of hydrogenated polyisobutylenes sold by NOF Corp., Japan under the trademark NOF-Plastol®. are commercially available from ExxonMobil Chemical Co., Baytown, Tex., U.S.A. under the trademark Paramount®. These include MML-80, MML-100, MML-120, and MML-140, which are paraffinic hydrocarbon polymers consisting of long, straight-chain macromolecules containing only chain-end olefinic bonds. MM polyisobutylenes have a viscosity average molecular weight of 70,000 to 90,000, and LM polyisobutylenes (e.g., LM-MS) are low molecular weight polyisobutylenes having a viscosity average molecular weight of 8,700 to 10. Additional examples of polyisobutylenes include VISTANEX LM-MH (viscosity average molecular weight of 10,000 to 11,700); Soltex PB-24 (Mn 950) from Amoco Corp. (Chicago, Illinois, U.S.A.), H-100 (Mn 910), H-1200 (Mn 2100); VISTANEX™ LM-MH from BP Chemicals, London, England and (e.g. 200, D10, and DE3; and 200). Polyisobutylenes generally have a Mn of 900 to 1300. In addition to or as an alternative to polyisobutylenes, the binder can include or be butyl rubber, styrene-ethylene / butylene-styrene (SEBS) block copolymer, styrene-ethylene / propylene-styrene (SEPS) block copolymer, polyolefin plastomer, or a combination thereof. SEBS and SEPS block copolymers are known in the art and can be G polymers from Kraton Polymers U.S. LLC, Houston, Tex., U.S.A., and as Septon polymers from Kuraray America, Inc., New York, N.Y., U.S.A. Polyolefin plastomers are also known in the art and can be GA 1900 and GA 1950 compositions are commercially available from Dow Chemical Company, Elastomers & Specialty Products Division, Midland, Mich., U.S.A.

[0216] The amount of the bonding agent present in the sealant depends on various factors (e.g., the amount and / or type of the at least one silicone-polyether copolymer, the intended use of the sealant, the curing conditions to which the sealant is intended to be exposed, etc., the presence / absence of a vehicle / solvent, etc.) and can be readily determined by one skilled in the art. Generally, where a bonding agent is present, the sealant comprises the bonding agent in an amount of 1 to 50 parts by weight, alternatively 5 to 40 parts by weight, alternatively 5 to 35 parts by weight, based on the combined weight of all components in the sealant.

[0217] In some embodiments, the sealant comprises an anti-aging additive. Examples of anti-aging additives include antioxidants, UV absorbers, UV stabilizers and / or light stabilizers, heat stabilizers, and combinations thereof. The anti-aging additive can be or include one anti-aging additive, or alternatively can include two or more different anti-aging additives. Further, one particular anti-aging additive can have multiple functionalities (e.g., act as both a UV absorber and a UV stabilizer, as both an antioxidant and a UV absorber, etc.). Many suitable anti-aging additives are known in the art and are commercially available. For example, suitable antioxidants include phenolic antioxidants (e.g., fully hindered phenols and partially hindered phenols) and combinations of phenolic antioxidants with stabilizers (e.g., hindered amines, such as tetramethylpiperidine derivatives, also known as “hindered amine light stabilizers” (HALS)). Suitable phenolic antioxidants include vitamin E and Irganox® from BASF. Suitable UV absorbers include benzotriazole UV absorbers, such as Tinuvin® from BASF. Suitable UV stabilizers include benzotriazole UV stabilizers, such as Tinuvin® from BASF. Suitable heat stabilizers include phosphites, such as Irgafos® from BASF. 1010. 1010 includes pentaerythritol tetrakis(3-(3,5-di-tert-butyl-4- hydroxyphenyl)propionate). Examples of UV absorbers include branched and linear 2-(2H-benzotriazol-2-yl)-6-dodecyl-4-methyl-phenol (Tinuvin® 99 from BASF); 2-(2H-benzotriazol-2-yl)-4-(1,1,3,3-tetramethylbutyl)-phenyl isocyanate (Tinuvin® 329 from BASF); and combinations thereof 571) Examples of UV stabilizers include bis(1,2,2,6,6-pentamethyl-4-piperidyl) sebacate; 1,2,2,6,6-pentamethyl-4-piperidyl / sebacic acid methyl ester; and combinations thereof 272). These and other additives such as 765) are commercially available from BASF. Other UV and light stabilizers are commercially available and examples are LowLite from Chemtura, OnCap from PolyOne, and Light Stabilizer 210 from E.I. du Pont de Nemours and Company, Delaware, U.S.A. Oligomeric (higher molecular weight) stabilizers can also be used in or as anti-aging additives, for example to minimize the potential for anti-aging additives to migrate out of the sealant or cured product thereof. Examples of such oligomeric antioxidant stabilizers include 622, which is a dimethyl ester of copolymerized succinic acid and 4-hydroxy-2,2,6,6- tetramethyl-l-piperidinoethanol. Examples of heat stabilizers include iron oxide, carbon black, iron carboxylate salts, cerium hydrate, barium zirconate, cerium and zirconium octoates, porphyrins, and the like, and combinations thereof.

[0218] The amount of anti-aging additive present in the sealant depends on various factors (e.g., the amount and / or type of at least one silicone-polyether copolymer, the intended use of the sealant, the curing conditions to which the sealant is intended to be exposed, etc.) and can be readily determined by one of skill in the art. Generally, where an anti-aging additive is present, the sealant comprises the anti-aging additive in an amount greater than 0 wt% to 5 wt%, alternatively from 0.1 wt% to 4 wt%, alternatively 0.5 wt% to 3 wt%, based on the total weight of the sealant.

[0219] In certain embodiments, the sealant includes a water release agent, i.e., a component that releases water over time (e.g., in response to applied conditions, such as temperature and / or pressure). Generally, the water release agent contains an amount of water sufficient to react, at least partially, with the sealant components, and is thus selected to release the amount of water when exposed to the applied conditions (e.g., the service temperature of the sealant) for a sufficient amount of time. However, the water release agent is generally selected to sufficiently bind with the water so as to prevent the release of too much water during the manufacture and / or storage of the sealant. For example, the water release agent is generally sufficiently bound with the water during the compounding / formulating of the sealant such that there is sufficient water available for the condensation reaction of the at least one silicone-polyether copolymer during or after the application process in which the sealant is used. This “controlled release” characteristic also provides the benefit of avoiding the release of too much water and / or too quickly during the application process, as this can cause blistering or voids in the reaction product formed from the condensation reaction of the at least one silicone-polyether copolymer of the sealant. The particular water release agent selected can depend on various factors (e.g., other components of the sealant, the amount / type of the at least one silicone-polyether copolymer, the type of condensation reaction catalyst, the process conditions under which the sealant will be formulated, etc.), and will be readily determined by one of skill in the art. Suitable water release agents are exemplified by metal salt hydrates, hydrated molecular sieves, and precipitated carbonates. Particular examples include the products sold under the trademarks SPM is a precipitated calcium carbonate available from Solvay Group. In certain embodiments, the water release agent is selected to include, alternatively is, precipitated calcium carbonate. The water release agent can be selected to ensure that not all of the water content is released during compounding, while still releasing a sufficient amount of water for the condensation reaction of the at least one silicone-polyether copolymer when exposed to the application temperature range for a sufficient period of time. The amount of water release agent present in the sealant depends on various factors (e.g., the water permeability of the at least one silicone-polyether copolymer, the presence / absence of a vehicle / solvent, the presence / absence of a desiccant, the method of formulating / preparing the sealant, etc.), and can be readily determined by one of skill in the art. Generally, in the presence of a water release agent, the sealant includes the water release agent in an amount of 1 part by weight to 50 parts by weight, alternatively 5 parts by weight to 40 parts by weight, alternatively 5 parts by weight to 30 parts by weight, based on the combined weight of all components in the sealant.

[0220] In some embodiments, the sealant comprises a pigment (i.e., a component that imparts color to the sealant and / or reaction products thereof). Such pigments can comprise any inorganic compound, for example, metal compounds (such as chromium oxide, titanium oxide, cobalt pigments) as well as compounds that are not based on these metals, for example, non-metallic inorganic compounds. Examples of suitable pigments include indigo blue, titanium dioxide, carbon black, and combinations thereof, as well as other commercially available pigments such as Stan-Tone 505P01 green available from PolyOne. In certain embodiments, the pigment comprises carbon black. Specific examples of carbon black include: Shawinigan Acetylene Black available commercially from Chevron Phillips Chemical Company LP; SR 511 supplied by Sid Richardson Carbon Co, Akron, Ohio U.S.A.; and N330, N550, N762, N990 (from Degussa Engineered Carbons, Parsippany, N.J., U.S.A.). The amount of pigment present in the sealant depends on various factors (e.g., the amount and / or type of at least one silicone-polyether copolymer, the intended use of the sealant, the presence / absence of a vehicle / solvent, etc.) and can be readily determined by one skilled in the art. Generally, where a pigment is present, the sealant comprises the pigment in an amount greater than 0 wt% to 20 wt%, alternatively from 0.001 wt% to 10 wt%, alternatively 0.001 wt% to 5 wt%, based on the total weight of the sealant. carbon black (e.g., LB-1011); SR 511 supplied by Sid Richardson Carbon Co, Akron, Ohio U.S.A.; and N330, N550, N762, N990 (from Degussa Engineered Carbons, Parsippany, N.J., U.S.A.). The amount of pigment present in the sealant depends on various factors (e.g., the amount and / or type of at least one silicone-polyether copolymer, the intended use of the sealant, the presence / absence of a vehicle / solvent, etc.) and can be readily determined by one skilled in the art. Generally, where a pigment is present, the sealant comprises the pigment in an amount greater than 0 wt% to 20 wt%, alternatively from 0.001 wt% to 10 wt%, alternatively 0.001 wt% to 5 wt%, based on the total weight of the sealant.

[0221] In some embodiments, the sealant comprises rheology additives, such as rheology modifiers and / or viscosity modifiers. Examples of suitable rheology additives include waxes; polyamides; polyamide waxes; hydrogenated castor oil derivatives; metal soaps, such as calcium stearate, aluminum stearate, and / or barium stearate; and their derivatives, modifiers, and combinations thereof. In certain embodiments, as well as those skilled in the art will fully understand, the rheology modifier is selected to facilitate the incorporation, compounding, degassing, and / or mixing of the sealant (e.g., during its preparation). Specific examples of rheology additives include those known in the art and commercially available. Examples of such rheology modifiers include: Polyvest, available from Evonik; Disparlon, available from King Industries; Kevlar fiber pulp, available from DuPont; Rheospan, available from Nanocor; Ircogel, available from Lubrizol; and Palmer Holland. SLX and other combinations thereof.

[0222] In some embodiments, the rheology modifier includes, alternatively, a wax (e.g., paraffin, microcrystalline wax, or a combination thereof). Waxes typically comprise one or more nonpolar hydrocarbons, which may contain branched, cyclic, or combined structures. Examples of suitable waxes include petroleum microcrystalline waxes available from Strahl & Pitsch, Inc. (West Babylon, NY, USA) under the following names: SP 96 (melting point 62°C to 69°C), SP 18 (melting point 73°C to 80°C), SP 19 (melting point 76°C to 83°C), SP 26 (melting point 76°C to 83°C), SP 60 (melting point 79°C to 85°C), SP 617 (melting point 88°C to 93°C), SP 89 (melting point 90°C to 95°C), and SP 624 (melting point 90°C to 95°C). Other examples of suitable waxes include those produced by Crompton Corporation, Petrolia, Pa., USA, under a trademark. Those for sale. This type of wax includes: 180-W, which contains saturated branched and cyclic nonpolar hydrocarbons and has a melting point from 79°C to 87°C; W-445, which contains saturated branched and cyclic nonpolar hydrocarbons, and has a melting point from 76°C to 83°C; and W-835, which comprises saturated branched and cyclic nonpolar hydrocarbons and has a melting point from 73 °C to 80 °C. In certain embodiments, the wax includes, alternatively is, a microcrystalline wax that is solid at room temperature (25 °C). In some embodiments, the melting point of the wax is selected to be within the desired application temperature range (i.e., the temperature range in which the sealant will be used / applied). It is believed that the wax acts as a processing aid when melted, which substantially reduces the incorporation of fillers in the composition during compounding, the compounding process itself, and during the outgassing step, if used at all. For example, in certain embodiments, the melting temperature of the wax is less than 100 °C, and the mixing of the parts can be facilitated prior to application (e.g., when the sealant is a multi-part composition), even in a simple static mixer. In this case, the wax can also facilitate the application of the sealant at temperatures of 80 °C to 110 °C, alternatively 90 °C to 100 °C, and have good rheology.

[0223] The amount of rheological additive present in the sealant depends on various factors (e.g., the amount and / or type of at least one silicone-polyether copolymer, the intended use of the sealant, the curing conditions to which the sealant is intended to be exposed, the presence / absence of a vehicle / solvent, etc.) and can be readily determined by one skilled in the art. Generally, in the presence of a rheological additive, the sealant comprises the rheological additive in an amount greater than 0 parts by weight to 20 parts by weight, alternatively from 1 part by weight to 15 parts by weight, alternatively 1 part by weight to 5 parts by weight, based on the combined weight of all components in the sealant.

[0224] In certain embodiments, the sealant includes a vehicle (e.g., a carrier vehicle, such as a solvent and / or diluent). Depending on the selection of the various components of the sealant, the carrier vehicle can be, for example, an oil (e.g., an organic oil and / or a silicone oil), a solvent, water, and the like. As understood by one skilled in the art, the particular vehicle used, if any, is selected to facilitate (e.g., increase) the flow of the sealant or a portion thereof (e.g., one or more portions of the sealant when the sealant is a multi-part composition); and the introduction of certain components (e.g., at least one silicone-polyether copolymer, chain extender, endblocker, and the like). As such, suitable vehicles are varied and generally include vehicles that aid in fluidizing one or more components of the sealant without substantially reacting with any such components. Thus, the vehicle can be selected based on the solubility, volatility, or both, of one or more components of the sealant. In this regard, solubility refers to the vehicle being sufficient to dissolve and / or disperse one or more components of the sealant, and volatility refers to the vapor pressure of the vehicle. If the vehicle is too volatile (i.e., the vapor pressure is too high for the intended use), then at the application temperature, bubbles can form in the sealant, which can lead to cracks and / or otherwise impair or adversely affect the properties of the cured product formed from the sealant. However, if the vehicle is not sufficiently volatile (i.e., the vapor pressure is too low for the intended use), then the vehicle can reside in and / or act as a plasticizer in the cured product of the sealant. Examples of suitable vehicles generally include silicone fluids, organic fluids, and combinations thereof.

[0225] In some embodiments, the vehicle of the sealant includes, alternatively is, a silicone fluid. The silicone fluid is generally a low viscosity and / or volatile siloxane. In some embodiments, the silicone fluid is a low viscosity organopolysiloxane, a volatile methylsiloxane, a volatile ethylsiloxane, a volatile methyl ethyl siloxane, and the like, or combinations thereof. Generally, the silicone fluid has a viscosity in the range of 1 to 1,000 mm 2 / s at 25 °C. In some embodiments, the silicone fluid includes a silicone having the general formula (R 28 R 29 SiO) I where each R 28 and R 29are independently selected from H and substituted or unsubstituted hydrocarbyl groups, and subscript I is 3 to 8. Specific examples of suitable silicone fluids include hexamethylcyclotrisiloxane, octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, dodecamethylcyclohexasiloxane, octamethyltrisiloxane, decamethyltetrasiloxane, dodecamethylpentasiloxane, tetradecamethylhexasiloxane, hexadecamethylheptasiloxane, heptamethyl-3-{(trimethylsilyl)oxy)}trisiloxane, hexamethyl-3,3-bis{(trimethylsilyl)oxy}trisiloxane, pentamethyl{(trimethylsilyl)oxy}cyclotrisiloxane, and polydimethylsiloxane, polyethylsiloxane, polymethylethylsiloxane, polymethylphenylsiloxane, polydiphenylsiloxane, octylpolymethylsiloxane, hexamethyldisiloxane, heptamethyloctyltrisiloxane, hexylpolymethyltrisiloxane, and the like, as well as derivatives thereof, modifications thereof, and combinations thereof. Additional examples of suitable silicone fluids include polyorganosiloxanes having a suitable vapor pressure (such as 5 x 10 -7 m2 / s to 1.5 x 10 -6 m 2 / s), including DOWSIL; 200 fluids and OS fluids, which are commercially available from Dow Silicones Corporation, Midland, Mich., U.S.A.

[0226] In certain embodiments, the vehicle of the sealant comprises an organic fluid, alternatively an organic fluid, which typically comprises an organic oil including volatile and / or semi-volatile hydrocarbons, esters, and / or ethers. General examples of such organic fluids include volatile hydrocarbon oils such as C6-C 16 alkanes, C8-C 16 isoalkanes (e.g., isodecane, isododecane, isohexadecane, and the like), C8-C 16 branched esters (e.g., isohexyl neopentanoate, isodecyl neopentanoate, and the like), and the like, as well as derivatives, modifications, and combinations thereof. Additional examples of suitable organic fluids include aromatic hydrocarbons, aliphatic hydrocarbons, alcohols having more than 3 carbon atoms, aldehydes, ketones, amines, esters, ethers, glycols, glycol ethers, alkyl halides, aromatic halides, and combinations thereof. Hydrocarbons include isododecane, isohexadecane, Isopar L (C 11 -C 13 ), Isopar H (C 11 -C 12), hydrogenated polydecenes. Ethers and esters include isodecyl neopentanoate, neopentyl glycol heptanoate, glycol distearate, dicaprylyl carbonate, diethylhexyl carbonate, propylene glycol n-butyl ether, ethyl-3 ethoxypropionate, propylene glycol methyl ether acetate, tridecyl neopentanoate, propylene glycol methyl ether acetate (PGMEA), propylene glycol methyl ether (PGME), octadecyl neopentanoate, diisobutyl adipate, diisopropyl adipate, propylene glycol dioctanoate / dicaprate, octyl ether, octyl palmitate, and combinations thereof.

[0227] In some embodiments, the vehicle comprises an organic solvent, alternatively an organic solvent. Examples of organic solvents include those comprising alcohols such as methanol, ethanol, isopropanol, butanol, or n-propanol; ketones such as acetone, methyl ethyl ketone, and methyl isobutyl ketone; aromatic hydrocarbons such as benzene, toluene, and xylene; aliphatic hydrocarbons such as heptane, hexane, and octane; glycol ethers such as propylene glycol methyl ether, dipropylene glycol methyl ether, propylene glycol n-butyl ether, propylene glycol n-propyl ether, and ethylene glycol n-butyl ether; halogenated hydrocarbons such as dichloromethane, 1,1,1-trichloroethane, and dichloromethane; chloroform; dimethyl sulfoxide; dimethylformamide, acetonitrile; tetrahydrofuran; petroleum solvent; mineral spirits; naphtha; N-methyl pyrrolidone; and the like, as well as derivatives, modifications, and combinations thereof.

[0228] Other vehicles can also be used in the sealant. For example, in some embodiments, the vehicle comprises, alternatively is, an ionic liquid. Examples of ionic liquids include anion-cation combinations. Typically, the anion is selected from alkyl sulfate-based anions, tosylate anions, sulfonate-based anions, bis(trifluoromethanesulfonyl)imide anions, bis(fluorosulfonyl)imide anions, hexafluorophosphate anions, tetrafluoroborate anions, and the like, and the cation is selected from imidazolium-based cations, pyrrolidinium-based cations, pyridinium-based cations, lithium cations, and the like. However, combinations of various cations and anions can also be utilized. Specific examples of ionic liquids typically include 1 -butyl- 1 -methylpyrrolidinium bis(trifluoromethanesulfonyl)imide, 1 -methyl- 1 -propylpyrrolidinium bis-(trifluoromethanesulfonyl)imide, 3 -methyl- 1 -propylpyridinium bis(trifluoromethanesulfonyl)imide, n-butyl-3-methylpyridinium bis(trifluoromethanesulfonyl)imide, 1 -methyl- 1 -propylpyridinium bis(trifluoromethanesulfonyl)imide, diallyldimethylammonium bis(trifluoromethanesulfonyl)imide, methyltrioctylammonium bis(trifluoromethanesulfonyl)imide, 1 -butyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imide, 1,2-dimethyl-3-propylimidazolium bis(trifluoromethanesulfonyl)imide, 1 -ethyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imide, 1 -vinylimidazolium bis(trifluoromethanesulfonyl)imide, 1 -allylimidazolium bis(trifluoromethanesulfonyl)imide, 1 -allyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imide, lithium bis(trifluoromethanesulfonyl)imide, and the like, as well as derivatives, modifications, and combinations thereof.

[0229] The amount of vehicle present in the sealant depends on various factors (e.g., the amount and / or type of at least one silicone-polyether copolymer, the manner in which the sealant is formulated, the curing conditions to which the sealant is intended to be exposed, etc.) and can be readily determined by one skilled in the art. Typically, where a vehicle is present, the sealant comprises the vehicle in an amount of 1 to 99 weight percent, alternatively 1 to 75 weight percent, alternatively 2 to 60 weight percent, alternatively 2 to 50 weight percent, based on the total weight of the sealant.

[0230] In particular embodiments, the sealant comprises a tackifier. General examples of suitable tackifiers generally include tackifiers comprising aliphatic hydrocarbon resins (e.g., hydrogenated polyolefins having 6 to 20 carbon atoms), hydrogenated terpene resins, rosin esters, hydrogenated rosin glycerol esters, or combinations thereof. Specific examples of suitable tackifiers include natural or modified rosins, such as gum rosin, wood rosin, tall oil rosin, distilled rosin, hydrogenated rosin, dimerized rosin, and polymerized rosin; glycerol esters and pentaerythritol esters of natural or modified rosins, such as glycerol ester of gum rosin, glycerol ester of hydrogenated rosin, glycerol ester of polymerized rosin, pentaerythritol ester of hydrogenated rosin, and phenolic modified rosin pentaerythritol ester; copolymers and / or terpolymers of natural terpenes, such as styrene / terpene and / or alpha methyl styrene / terpene polymers; polyterpene resins having a softening point of 60 °C to 150 °C as determined by ASTM Method E28, such as those produced by polymerization of terpene hydrocarbons (e.g., pinene) in the presence of Friedel-Crafts catalysts and hydrogenated derivatives thereof (e.g., hydrogenated polyterpenes); phenolic modified terpene resins and hydrogenated derivatives thereof, such as those produced by acid-mediated condensation of dicyclic terpenes and phenols; aliphatic petroleum hydrocarbon resins, such as those produced by polymerization of monomers consisting primarily of olefins and diolefins, those having a ring and ball softening point of 60 °C to 135 °C, and hydrogenated aliphatic petroleum hydrocarbon resins; cycloaliphatic petroleum hydrocarbon resins and hydrogenated derivatives thereof; aliphatic / aromatic or cycloaliphatic / aromatic copolymers and hydrogenated derivatives thereof; and combinations thereof. In some embodiments, the sealant comprises a solid tackifier (i.e., a tackifier having a ring and ball softening point greater than 25 °C). Other examples of suitable tackifiers include commercially available varieties such as aliphatic hydrocarbon resins exemplified by ESCOREZ 1102, 1304, 1310, 1315, and 5600 from Exxon Chemical and Eastotac H-100, H-115E, and H-130L from Eastman; hydrogenated terpene resins exemplified by Arkon P 100 from Arakawa Chemicals and Wingtack 95 from Goodyear; hydrogenated rosin glycerol esters exemplified by Staybelite Ester 10 and Foral from Hercules; polyterpenes exemplified by Piccolyte A125 from Hercules; aliphatic / aromatic and / or cycloaliphatic / aromatic resins exemplified by ECR 149B and ECR 179A from Exxon Chemical; and combinations thereof.The amount of tackifier present in the sealant depends on various factors (e.g., the amount and / or type of at least one silicone-polyether copolymer, the type and / or amount of other components in the sealant, the intended use of the sealant, etc.) and can be readily determined by one of skill in the art. Generally, where a tackifier is present, the sealant includes the tackifier in an amount of 1 to 20 parts by weight, based on the combined weight of all components in the sealant.

[0231] In certain embodiments, the sealant includes a corrosion inhibitor. Examples of suitable corrosion inhibitors include benzotriazoles, mercaptobenzotriazoles, and the like, and combinations thereof. Specific examples of suitable corrosion inhibitors are known in the art and are commercially available, such as CORR-STOP® available from R.T. Vanderbilt, Norwalk, Conn., U.S.A. 826 (e.g., 2,5-dimercapto-l,3,4-thiadiazole derivatives) and 484 (alkylthiadiazoles).

[0232] The amount of corrosion inhibitor present in the sealant depends on various factors (e.g., the amount and / or type of at least one silicone-polyether copolymer, the intended use of the sealant, the curing conditions to which the sealant is intended to be exposed, etc.) and can be readily determined by one of skill in the art. Generally, where a corrosion inhibitor is present, the sealant includes the corrosion inhibitor in an amount of 0.05 to 0.5 percent by weight, based on the total weight of the sealant.

[0233] As introduced in the various sections above, the various components of the sealant can serve multiple purposes, and thus certain additives can overlap with the components described herein. For example, certain alkoxysilanes can serve as a filler treatment agent, as an adhesion promoter, and as a crosslinker. Additionally, the sealant can also include additional additives not described above, such as a catalyst inhibitor, a cure promoter, a color change additive, and the like, as readily determined by one of skill in the art. Such additional additives are independently selected, and the amount of each additive used in the sealant is selected based on the intended use of the additive. Generally, where such additional additives are present, the sealant includes each of such additional additives in an amount of 0.001 to 10 percent by weight, alternatively 0.01 to 5 percent by weight, alternatively 0.1 to 1 percent by weight, based on the total weight of the sealant.

[0234] As noted above, the sealant can be prepared as a one-part composition or a multi-part composition (e.g., including 2, 3, 4, or more parts). For example, in some embodiments, the sealant is prepared as a one-part composition, which can be prepared by combining all of the components together in any convenient manner, such as mixing. Such one-part compositions can be prepared by combining (e.g., premixing) at least one silicone-polyether copolymer with various additives (e.g., fillers) to form an intermediate mixture, and then combining (e.g., by mixing) the intermediate mixture with a premix including a condensation reaction catalyst and other various additives to form a sealant mixture or sealant. At any desired stage, other additives (e.g., anti-aging additives, pigments, etc.) can be added to the sealant by combining, such as with the intermediate mixture, premix, or sealant mixture. As such, a final mixing step can be performed (e.g., under substantially anhydrous conditions) to form the sealant, which is typically stored under substantially anhydrous conditions (e.g., in a sealed container) until ready for use.

[0235] In some embodiments, the sealant is prepared as a multi-part composition (e.g., when a crosslinker is used). In such embodiments, the condensation reaction catalyst and crosslinker are typically stored in separate parts, which are combined shortly before the sealant is used. For example, the sealant can include a two-part curable composition, which is prepared by combining at least one silicone-polyether copolymer and a crosslinker in any convenient manner (e.g., mixing) to form a first (i.e., curative) part. A second (i.e., base) part can be prepared by combining a condensation reaction catalyst and (I) copolymer in any convenient manner (e.g., mixing). The components can be combined at room temperature or elevated temperature and under ambient conditions or anhydrous conditions, depending on different factors, such as whether a one-part or multi-part composition is selected. The base part and curative part can then be combined by any convenient manner (e.g., mixing) shortly before use. The base part and curative part can be combined in a 1 : 1 ratio or in relative amounts of base:curative ranging from 1 : 1 to 10: 1.

[0236] The equipment used to mix the sealant components is not particularly limited and is generally selected according to the type and amount of each component selected for the sealant or portion thereof (collectively referred to as "sealant composition"). For example, stirred batch kettles can be used for relatively low viscosity sealant compositions, such as compositions that will react to form a gum or gel. Alternatively, continuous compounding equipment (e.g., an extruder, such as a twin screw extruder) can be used for more viscous sealant compositions, as well as sealant compositions containing relatively large amounts of particulates. Exemplary methods that can be used to prepare the sealant compositions described herein include, for example, those described in U.S. Patent Publication Nos. 2009 / 0291238 and 2008 / 0300358, the portions of which are incorporated herein by reference.

[0237] Sealant compositions prepared as described above can be stable when stored in a container that reduces or prevents exposure of the sealant composition to moisture. However, when exposed to atmospheric humidity, the sealant composition can react through condensation reactions. Additionally, when a water release agent is used, the sealant composition can react through condensation reactions without exposure to atmospheric humidity.

[0238] A cured product is also provided. The cured product is formed from a sealant. More specifically, the cured product is formed by curing a sealant, for example, through the condensation reactions described above.

[0239] A composite article comprising a cured product is also provided. More specifically, the composite article comprises a substrate and a cured product disposed on the substrate. The composite article is prepared by disposing a sealant on a substrate and curing the sealant to produce a cured product on the substrate, thereby preparing the composite article. The substrate is exemplified by, for example, an exterior building facade.

[0240] A method of sealing a space defined between two elements is also disclosed. The method comprises applying a sealant to the space and curing the sealant in the space, thereby sealing the space.

[0241] As described above, the present application allows for selective control or otherwise adjustment of the properties of the cured product of the composition as well as its rate of cure. Generally, it is difficult or traditionally impossible to optimize the modulus and tensile strength without sacrificing or affecting the rate of cure and the concentration of the condensation reaction catalyst. In other words, maximizing the rate of cure can require a high concentration of the condensation reaction catalyst and can affect the properties of the cured product, such as the modulus and elongation.

[0242] It has been surprisingly discovered that by using different end-capped organosilicon compounds, different silicone moieties X of formula (I) and formula (II) are created within at least one silicone-polyether copolymer of the composition, which can improve modulus and elongation compared to using only silicone moieties X of, for example, formula (I). Furthermore, by including different silicone moieties X in at least one silicone-polyether copolymer of the composition, much faster cure times can be achieved compared to using only silicone moieties X of, for example, formula (II). In fact, these surprising benefits can be achieved at lower concentrations of condensation reaction catalyst than conventionally required, which is particularly advantageous, especially when the condensation reaction catalyst comprises tin. Cure speed can be maximized by increasing the content of silicone moieties X of formula (I), and the mechanical properties of the cured product, such as modulus and elongation, can be optimized by increasing the content of silicone moieties X of formula (II). Thus, depending on the desired cure speed, concentration of condensation reaction catalyst, and performance properties of the cured product, the relative amounts of silicone moieties X of formula (I) and silicone moieties X of formula (II) allow for selective control or tuning of reaction parameters and performance properties. Accordingly, the present invention also provides methods of selectively controlling or tuning reaction parameters, as well as performance properties of the composition and related cured product.

[0243] The following examples are intended to illustrate the present invention and should not be construed as limiting the scope of the invention in any way.

[0244] Certain components utilized in the examples are listed in Table 1 below.

[0245] Table 1 : Components / compounds used

[0246]

[0247] General procedure 1 : Preparation of examples 1-5

[0248] Preparation of Examples 1-5 followed General Procedure 1. The specific amounts of each component used in the preparation of Examples 1-5 are detailed in Table 2 below.

[0249] In General Procedure 1, the rotary flask was equipped with a rotary evaporator equipped with an oil heating bath. The flask was purged with N2and polyether compound 1 was placed in it. The rotary evaporator was set to 90 rotations per minute (rpm) and purged with N2three times to remove oxygen. The heating bath was set to 115 °C and the rotary evaporator was evacuated to maximum vacuum to dry the polyether compound 1 for 2-3 hours. The flask was removed from the oil heating bath, cooled to ambient temperature under vacuum, purged with N2and transferred to a nitrogen glove bag.

[0250] The polyether compound 1 was then weighed into a SpeedMixer cup. The chain extending silicone compound, first endblocking silicone compound, and hydrosilylation catalyst were placed in the cup and stirred with a spatula for 30 seconds. The second endblocking silicone compound was weighed into a syringe and placed into the contents of the cup. The cup was then capped and sealed with electrical tape, and mixed on a high speed mixer for 3 minutes at 3500 rpm. The cup was then placed in a metal tin container with a desiccant and purged with nitrogen. The metal tin container was then placed in an oven at 55 °C for 6 hours. The metal tin container was then removed from the oven, cooled to room temperature, and the cup was removed and placed into a glove bag for sampling of its contents (NMR, viscosity, GPC, etc.).

[0251] Table 2 below shows the amount of each component used in the preparation of Examples 1-5 according to General Procedure 1.

[0252] Table 2: Preparation of examples 1-5

[0253] Preparation example PC1 (g) HC [ppm Pt] CEOC (g) FEOC (g) SEOC (g) 1 87.8 6 3.0 1.7 0.2 2 86.1 6 3.0 1.1 0.4 3 87.7 6 3.0 0.6 0.6 4 39.2 5 1.4 0.304 0.183 5 38.1 5 1.3 0.351 0.098

[0254] General procedure 2: Preparation of examples 6-11

[0255] Preparation Examples 6-11 followed General Procedure 2. The specific amounts of each component used in Preparation Examples 6-11 are detailed in Table 3 below.

[0256] In General Procedure 2, the rotary flask was equipped with a rotary evaporator equipped with an oil heating bath. The flask was purged with N2and placed polyether compound 1 therein. The rotary evaporator was set to 90 rotations per minute (rpm) and purged with N2three times to remove oxygen. The heating bath was set to 115 °C and the rotary evaporator was evacuated to maximum vacuum to dry the polyether compound 1 for 2-3 hours. The flask was removed from the oil heating bath, cooled to ambient temperature under vacuum, purged with N2and transferred to a nitrogen glove bag.

[0257] The polyether compound 1 was then weighed into a SpeedMixer cup. The chain extending silicone compound, the first capping silicone compound, and the third capping silicone compound (when used in Preparation Examples 6-8, as shown in Table 3 below), and the hydrosilylation catalyst were placed in the cup and stirred with a spatula for 30 seconds. In Preparation Examples 9-11, the second capping silicone compound was weighed into a syringe and placed into the contents of the cup. The cup was then capped and sealed with electrical tape, and mixed on a high speed mixer for 3 minutes at 3500 rpm. The cup was then placed in a metal tin container with a desiccant, and purged with nitrogen. The metal tin container was then placed in an oven at 55 °C for 6 hours. The metal tin container was then removed from the oven, cooled to room temperature, and the cup was removed and placed into a glove bag for analytical sampling (via NMR). The cup was transferred back into the glove bag, the curative and catalytic amount of hydrochloric acid were placed into the cup and stirred with a spatula for 30 seconds. The cup was capped and sealed with electrical tape, and mixed on a high speed mixer for 3 minutes at 3500 rpm. The cup was left in the glove bag overnight, and the contents of the cup were transferred to a rotary flask. The residual amounts of curative, ethanol, and hydrochloric acid were removed via a rotary evaporator first at 80 °C, and then at 115 °C for one hour. The contents of the rotary flask were transferred back into the glove bag for analytical sampling (NMR, viscosity, GPC, etc.).

[0258] Table 3 below shows the amount of each component used in Preparation Examples 6-11 according to the General Procedure 2. In Table 3, the amount of hydrochloric acid used is based on parts per million relative to the amount of curative used.

[0259] Table 3: Preparation of examples 6-11

[0260]

[0261] Preparation example 12:

[0262] Preparation Example 12 followed the General Procedure 1, with the only difference being that the second capping silicone compound was not used. Instead, Preparation Example 12 used only the first capping silicone compound. Table 4 below shows the amount of each component used in Preparation Example 12.

[0263] Table 4: Preparation of example 12

[0264] Preparation example PC1 (g) HC [ppm Pt] CEOC (g) FEOC (g) 12 443.1 5 15.1 10.0

[0265] Preparation example 13:

[0266] Preparation Example 13 followed the General Procedure 1 with the only difference being that the first end-capped organosilicon compound was not used. Instead, Preparation Example 13 used only the second end-capped organosilicon compound. As in the General Procedure 1, the second end-capped organosilicon compound was placed in the cup via syringe, rather than being placed in the cup with the chain-extending organosilicon compound and the polyether compound 1. Table 5 below shows the amount of each component used in Preparation Example 13.

[0267] Table 5: Preparation of example 13

[0268] Preparation example PC1 (g) HC [ppm Pt] CEOC (g) SEOC (g) 13 269.1 7.5 9.0 3.76

[0269] Preparation example 14:

[0270] Preparation Example 14 followed the General Procedure 2 with the only difference being that neither the first end-capped organosilicon compound nor the second end-capped organosilicon compound was used. Instead, Preparation Example 14 used only the third end-capped organosilicon compound. In addition, in Preparation Example 14, the third end-capped organosilicon compound was weighed into the cup with the polyether compound 1 and the chain-extending organosilicon compound, rather than being placed in the cup via syringe. Table 6 below shows the amount of each component used in Preparation Example 14. In Table 6, the amount of hydrochloric acid used is based on parts per million relative to the amount of the conversion agent used.

[0271] Table 6: Preparation of example 14

[0272] Preparation example PC1 (g) HC [ppm Pt] CEOC (g) TEOC (g) Converting agent (g) HC1 [ppm] 14 225.0 6 7.8 3.3 47.4 12

[0273] Preparation examples 15-17:

[0274] Preparation Examples 15-17 followed the General Procedure 1 with the only difference being that the chain-extending organosilicon compound was not used and polyether compound 2 was used instead of polyether compound 1. Table 7 below shows the amount of each component used in Preparation Examples 15-17.

[0275] Table 7: Preparation of examples 15-17

[0276]

[0277]

[0278] Preparation example 18:

[0279] Preparation Example 18 followed the General Procedure 1 with the only difference being that neither the second end-capped organosilicon compound nor the chain-extending organosilicon compound was used and polyether compound 2 was used instead of polyether compound 1. Table 8 below shows the amount of each component used in Preparation Example 18.

[0280] Table 8: Preparation of example 18

[0281] Preparation example PC2 (g) HC [ppm Pt] FEOC (g) 18 105.4 5 4.125

[0282] Preparation example 19:

[0283] Preparation Example 13 followed the General Procedure 1 with the only difference being that no first end-capping organosilicon compound or chain-extending organosilicon compound was used and polyether compound 2 was used instead of polyether compound 1. Table 9 below shows the amount of each component used in Preparation Example 19.

[0284] Table 9: Preparation of example 19

[0285] Preparation example PC1 (g) HC [ppm Pt] SEOC (g) 19 160.4 5 2.6

[0286] Examples 1-25 and comparative examples 1-5:

[0287] Compositions containing the silicone-polyether copolymers prepared in Preparation Examples 1-19 were prepared in Examples 1-25 and Comparative Examples 1-5. In certain examples, a particular composition consists of a particular silicone-polyether copolymer. In other examples, a particular composition contains a blend of two different silicone-polyether copolymers. Table 10 below shows the silicone-polyether copolymers and relative amounts used in Examples 1-25 and Comparative Examples 1-5.

[0288] Table 10: Examples 1-25 and comparative examples 1-5 :

[0289]

[0290]

[0291] Table 11 below shows the viscosity and GPC data for Examples 1-25 and Comparative Examples 1-5 measured as described above. In Table 11, “n / a” indicates that a particular measurement was not taken for a given example.

[0292] Viscosity : Viscosity measurements were made using an Anton Paar MCR-302 rheometer. Samples were measured at 25 °C using a plate with an 8 mm cone and a 1 degree cone angle (truncated gap = 22 pm; CP08-1) and at 25 °C and 0 °C using a plate with a 25 mm cone and a 2 degree cone angle (truncated gap = 106 pm; CP25-2). Constant shear technique was used for all materials. Temperature equilibration and sample volatility were not an issue for the measurements by monitoring the viscosity change.

[0293] GPCThe chromatographic apparatus consisted of a Waters 2695 Separations Module and a Waters 2410 differential refractometer. Separations were performed using two (300 mm x 7.5 mm) Polymer Laboratories PLgel 5 μιη Mixed-C columns (molecular weight separation range 200 to 2,000,000) preceded by a PLgel 5 μιη guard column (50 mm x 7.5 mm). Analysis was performed using certified grade THF as eluent at 1.0 mL / min flow, and both column and detector were controlled at 35 °C. Samples were prepared at 5 mg / mL in THF, solvated for approximately two hours with occasional shaking, and filtered through a 0.45 μιη PTFE syringe filter prior to analysis. A 100 μί injection volume was used, and data were collected for 25 minutes. Data collection and analysis were performed using ThermoLabsystems Atlas chromatography software and Polymer Laboratories Cirrus GPC software. Molecular weight averages were determined relative to a calibration curve (third order) created using polystyrene standards covering a molecular weight range of 580 to 2,300,000.

[0294] Table 11 : Examples 1-25 and comparative examples 1-5

[0295]

[0296]

[0297] Sealant examples 1-25 and comparative sealant examples 1-5

[0298] In sealant examples 1-25 and comparative sealant examples 1-5, sealants were formed using the compositions of examples 1-25 and comparative examples 1-5. To form the sealants having the compositions of examples 1-25 and comparative examples 1-5, 1000 parts per million by weight (ppmw) of catalyst and 5000 ppmw of adhesion promoter were combined with each of the compositions of examples 1-25 and comparative examples 1-5. The components of each of sealant examples 1-25 and comparative sealant examples 1-5 were mixed in a 40 g capacity polypropylene mixing cup for a Flacktek SpeedMixer® and mixed at 2000 rpm for 1 minute to yield each sealant as a homogeneous mixture. Each of sealant examples 1-25 and comparative sealant examples 1-5 was cured to yield a cured product, and properties of each cured product were measured as described below.

[0299] Tensile test ​Tensile properties were measured according to ASTM D412. In particular, each sealant was cast onto a Teflon plate sized 10 cm x 10 cm and having edge protection. The Teflon plate was placed in a room controlled to have a relative humidity of 50% and a temperature of 23 °C. The plate was left to cure in the room for 7 days and then moved to an air-circulated oven set to 50 °C, not adjusted for atmospheric moisture content and kept in the oven for 4 days. The sample was then removed from the oven and cooled to room temperature. Dogbone specimens were cut from the sample with a carbon steel die for determination of tensile strength and small pieces were cut from the sample for differential scanning calorimetry (DSC).

[0300] Dogbone sample size for tensile testing was 50 mm long with a 20 mm narrow neck length. An MTS test frame with a load cell having a full capacity of 100 N was used for the tensile testing. The test speed was 50.8 cm / min. Strain was calculated as displacement over the narrow neck length. The stress at break was calculated by dividing the peak stress by the initial cross-sectional area of the narrow neck region.

[0301] Debinding time Tack-free time (TFT) of the sealants was determined using a dry time recorder obtained from TQC. The dry time recorder is a fully digital controlled machine operated according to the BK (Beck Koller) method and meets ASTM D5895, ISO 9117-4 and DIN EN 14022. The dry time recorder was placed in a room having a constant humidity of 50%. The dry time recorder was equipped with a carrier having 6 pins that can be lowered onto the top of up to 6 25 x 300 mm aluminum panels coated with a 4 mil thick film of the sealant. The pins were then slowly pulled over the panels for a period of time that was set to cover the final curing time of each sealant. The evaluation of the tack-free time (TFT) was performed by moving the carrier over the panels and moving to the starting point of the curing stage. The TFT can then be determined by correlating the visual indication of the curing process with the relevant time read by the dry time recorder.

[0302] The hardness of each cured product was measured according to ASTM D2240.

[0303] The following Tables 12 and 13 show the tack-free time, tensile strength properties and hardness of each of the sealant and cured product of sealant examples 1-25 and comparative sealant examples 1-5.

[0304] Table 12: Sealant examples 1-25 and comparative sealant examples 1-5 :

[0305]

[0306]

[0307] Table 13: Sealant examples 1-25 and comparative sealant examples 1-5 :

[0308]

[0309]

[0310] Figure 1 The detack time of certain sealants (i.e., those of Comparative Examples 1 and 3, and Examples 1-3 and Examples 7-8) is shown as a function of the molar percentage of the silicone portion X of the first organosilicon end-capping compound (which is the silicone portion X of formula (I)). Figure 1 Comparative Example 3, which excludes the silicone portion X of Formula (I), has a TFT of 6638 minutes; however, Comparative Example 1, which includes only the silicone portion X of Formula (I) (i.e., excluding the silicone portion X of Formula (II),) has a TFT of only 24 minutes. Surprisingly, even increasing the content of the silicone portion X of Formula (I) by a relatively small amount causes the TFT to drop sharply from 6638 minutes to 288 minutes (see Comparative Examples 3 and 8). As shown in the examples, despite the significant improvement in TFT, mechanical properties are not sacrificed due to the content of the silicone portion X of Formula (II).

[0311] The invention has been described by way of example, and it should be understood that the terminology used is intended to be descriptive rather than restrictive. Clearly, many modifications and variations of the invention are possible in accordance with the teachings above. The invention may be practiced in ways other than those specifically described.

Claims

1. A composition comprising at least one silicone-polyether copolymer, said at least one silicone-polyether copolymer having an average formula X g [Z j Y o ] c Each X is independently a silicone portion having one of formula (I) or formula (II): (R 1 ) a (R 2 O) 3-a Si-D-SiR 1 2-O-SiR 1 2-D 1 -(I) (R 1 ) a (R 2 o) 3-a Si-D 1 -(II) Each Y is an independently selected polyether moiety, and each Z is an independently selected silicone moiety. Each R 1 It is an independently chosen substituted or unsubstituted hydrocarbon group having 1 to 18 carbon atoms; each R 2 Each D is an independently chosen alkyl group having 1 to 8 carbon atoms; each D is independently a divalent hydrocarbon group having 2 to 18 carbon atoms; each D 1 Independently, each subscript a is a divalent hydrocarbon group having 2 to 18 carbon atoms; each subscript a is independently 0 or 1; subscript c is 1 to 150; subscript g > 1; each subscript j is independently 0 or 1; each subscript o is independently 0 or 1, provided that in each part indicated by subscript c 1 ≤ j + o ≤ 2, and there exists at least one part indicated by subscript c where subscript o is 1; in, The silicone-polyether copolymer comprises at least one silicone portion X of formula (I) and at least one silicone portion X of formula (II) in the same molecule.

2. The composition according to claim 1, wherein each polyether portion Y has the following formula: –CH2–CH(R 3 )–[D 2 ] m –O–[C2H4O] x [C3H6O] y [C4H8O] z –[D 2 ] m –CH(R 3 )–CH2–, Each R 3 Independently, it is a hydrocarbon group, alkoxy group, silyl group, or H having 1 to 6 carbon atoms; each D 2 It is an independently selected divalent group having 1 to 6 carbon atoms, with subscript m being 0 or 1, subscript x being 0 to 999, subscript y being 1 to 1000, and subscript z being 0 to 999, wherein the unit indicated by subscripts x, y, and z in the polyether portion Y can be in a random or block form; and Each organosilicon portion Z independently has the following formula: Each R 1 It is independently selected and as defined above, and each d in each organosilicon portion Z is independently 0 to 999.

3. The composition according to claim 1 or 2, wherein the composition is further defined as a sealant, and wherein the sealant further comprises a condensation reaction catalyst.

4. A method for preparing a composition comprising at least one silicone-polyether copolymer, the method comprising: A composition comprising at least one silicone-polyether copolymer is prepared by reacting a polyether compound having an average of more than one terminal unsaturated group, an optionally chain-extended organosilicon compound, a first end-capped organosilicon compound, and a second end-capped organosilicon compound different from the first end-capped organosilicon compound in the presence of a hydrosilylation catalyst. The composition thereon is the composition according to claim 1 or 2.

5. A cured product of the composition according to claim 3.

6. A composite material article comprising a substrate and a cured product according to claim 5 disposed on the substrate.

7. A method for preparing composite material articles, the method comprising: Set the composition on a substrate; as well as The composition is cured to produce a cured product on the substrate, thereby forming the composite material article; The composition thereon is the composition according to claim 3.

8. A method for sealing a space defined between two elements, the method comprising: The composition is applied to the space; as well as The composition is cured in the space, thereby sealing the space; The composition thereon is the composition according to claim 3.

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