liquid silicone resin

Abstract

A liquid silicone resin composition containing (A) a polysiloxane, (B) a polyether alcohol compound, and optionally (C) an amino silicon compound. The polysiloxane (A) is dispersed in the polyether alcohol compound (B), and optionally comprises an MQ resin functionalized with the polyether alcohol compound (B), which may also optionally have amino functionality. The liquid silicone resin composition has a tunable viscosity that can range from 100 to 800,000 cps at 25°C. A method for producing a liquid silicone resin includes combining a solid silicone resin with the polyether alcohol compound (B) to obtain a mixture containing the polysiloxane (A) and the polyether alcohol compound (B), and liquefying the mixture to prepare the liquid silicone resin composition. The method may optionally include an amino silicon compound (C).

Description

[Technical Field]

[0001] (CROSS-REFERENCE TO RELATED APPLICATIONS) This application claims priority to and all benefits of U.S. Provisional Patent Application No. 63 / 107,643, filed October 30, 2020, the contents of which are incorporated herein by reference.

[0002] FIELD OF THE INVENTION FIELD OF THE DISCLOSURE This disclosure relates generally to silicone compositions, and more particularly to liquid silicone resin compositions and methods for preparing the same. [Background technology]

[0003] Silicones are polymeric materials used in many commercial applications, primarily because of their distinct advantages over their carbon-based analogues. Silicones, more specifically called polymerized siloxanes or polysiloxanes, contain an inorganic silicon-oxygen backbone (...-Si-O-Si-O-Si-O-...) with organic side groups attached to the silicon atoms. Organic side groups can be used to link two or more of these backbones together. By varying the -Si-O- chain length, side groups, and crosslinking, silicones with a wide variety of properties and compositions can be synthesized, with silicone networks exhibiting consistency ranging from liquid to gel, rubber, and hard plastic. Silicone and siloxane-based materials are utilized in a myriad of end uses and environments, including as ingredients in a wide variety of industrial, home care, and personal care formulations.

[0004] Silicone and siloxane-based materials are known in the art and are utilized in a myriad of end uses and environments. The most common silicone materials are based on the linear organopolysiloxane polydimethylsiloxane (PDMS), a silicone oil. Such organopolysiloxanes are used in many industrial, home care, and personal care formulations. The second largest group of silicone materials is based on silicone resins formed by branched and cage-type oligosiloxanes. Unfortunately, the use of siloxane-based materials in certain applications that could benefit from certain inherent attributes of organopolysiloxanes (e.g., low loss and stable optical transmission, thermal and oxidative stability, etc.) remains limited due to the weak mechanical properties of conventional silicone networks amenable to functionalization and / or further reaction, which can manifest in materials with poor or inappropriate properties, such as low tensile strength and low tear strength. Furthermore, conventional silicone networks and carbon-based polymers are often incompatible and / or have antagonistic properties, and further research is needed to identify useful methods for efficiently and effectively functionalizing silicones, such as silicone resins.

[0005] For example, many traditional silicone materials (e.g., siloxanes, silicone resins) are hydrophobic and therefore difficult to mix with polar organic materials under a wide range of conditions. Therefore, these silicone materials are typically utilized in solid form, or, when solutions / dispersions are required, with non-polar organic (e.g., hydrocarbon) solvents (i.e., BTEX solvents) such as benzene, toluene, ethylbenzene, and xylene. Unfortunately, these conditions are also often incompatible with certain polar organic materials and the process conditions required for their use. Furthermore, the properties of BTEX solvents raise numerous environmental and health-related concerns, necessitating further investigation into the safe and effective use of silicone materials in non-traditional applications. Summary of the Invention

[0006] A liquid silicone resin composition (the "composition") is disclosed. The composition comprises (A) the following general formula: (R 1 3SiO 1 / 2 ) a (R 2 2SiO 2 / 2 ) b (R’R 2 SiO 2 / 2 ) b’ (R 2 SiO 3 / 2 ) c (R’SiO 3 / 2 ) c’ (SiO 4 / 2 ) d and contains a polysiloxane having, The subscripts a, b, b', c, c', and d are molar fractions such that a + b + b' + c + c' + d = 1, provided that 0 < a < 1, 0 ≤ b < 0.2, 0 ≤ b' ≤ 0.1, 0 < c < 0.2, 0 ≤ c' ≤ 0.1, 0 < d < 1, 0 ≤ b' + c' ≤ 0.1, and the ratio of subscript a to subscript d is 0.5 to 1.5 (a:d). Each R 1 is independently selected from a hydrocarbyl group having 1 to 30 carbon atoms, -OH, and H. Each R 2 is independently selected from R 1 and -OX, where each X is independently H, a hydrocarbyl group R having 1 to 30 carbon atoms, or a polyether moiety having the general formula -Y-R 3 (-[Y] j -Z) i , where R 3 is a substituted or unsubstituted hydrocarbon segment, each Y is an independently selected oxyalkylene segment of the general formula (C n H 2n O) m , where the subscript m is 1 to 50, the subscript n is independently selected from 2 to 4 in each part represented by the subscript m, each Z is independently H or a resinous silicone moiety, the subscript i is 0 to 8, the subscript j is independently 0 or 1 in each part represented by the subscript i, and each R' contains an independently selected amino group. The composition also comprises (B) the general formula HO-Y-R 3(-[Y] j -Z] i wherein each Y, R 3 , Z, the subscript j, and the subscript i are as defined above.

[0007] Also disclosed is a method for preparing a liquid silicone resin composition. The method comprises (I) combining a solid silicone resin and a polyether alcohol compound (B) together to obtain a mixture comprising polysiloxane (A) and polyether alcohol compound (B). The general formula of the solid silicone resin is: (R 1 3SiO 1 / 2 ) a (R 4 2SiO 2 / 2 ) b (R 4 SiO 3 / 2 ) c (SiO 4 / 2 ) d , In the formula, each R 4 is R 1 and -OR, with the proviso that R 4 is selected from —OH and —OR in at least one T siloxy unit designated by subscript c, and each R 1 , R, and the subscripts a, b, c, and d are as defined above. The method also includes (II) liquefying a mixture comprising polysiloxane (A) and polyether alcohol compound (B) to prepare a liquid silicone resin composition. The method can optionally utilize (C) an amino silicon compound. DETAILED DESCRIPTION OF THE INVENTION

[0008] A liquid silicone resin composition ("composition") is provided herein, along with a method for its preparation. As will be understood from the description herein, the composition provides a functional MQ resin, optionally capped with one or more polyether-containing moieties, in liquid form without the need for a solvent or other carrier vehicle. By "liquid," we mean that the composition is flowable and has a viscosity that can be measured at 25°C. The specific materials and conditions utilized provide the composition with a highly tunable liquid viscosity, thereby providing the composition with numerous uses in a myriad of compositions and methods, including preparing curable compositions (e.g., those based on one or more silicones) and their various components. Furthermore, due to unique structural features, the liquid composition may be suitable for dispersion in water, polyols, or other polar liquid formulations (e.g., those containing anionic and / or nonionic surfactants).

[0009] The compositions generally comprise (A) a polysiloxane, (B) a polyether alcohol compound, and optionally (C) an amino silicon compound, which are described in order below, along with any additional compounds that may be present in the composition, which may be collectively referred to herein as the "components" of the composition (i.e., "component (A)," "component (B)," etc., respectively), or similarly as "compound(s)" and / or "reagent(s)" (A) and / or (B), etc.

[0010] As will be appreciated by those skilled in the art, siloxanes may be characterized in terms of the [M], [D], [T], and / or [Q] units / siloxy groups therein. More specifically, these [M], [D], [T], and [Q] siloxy groups each represent the structural units of individual functional groups present in polysiloxanes, such as organosiloxanes and organopolysiloxanes. More specifically, [M] is a siloxane having the general formula R"SiO 1 / 2 [D] represents a monofunctional unit of the general formula R″2SiO 2 / 2 [T] represents a difunctional unit of the general formula R″SiO 3 / 2 and [Q] represents a trifunctional unit of the general formula SiO 4 / 2and is represented by the following general structural moiety:

[0011] [ka]

[0012] In these general structural moieties, each R" is independently a monovalent or polyvalent substituent. As understood in the art, the specific substituents suitable for each R" are not particularly limited and can be monoatomic or polyatomic, organic or inorganic, linear or branched, substituted or unsubstituted, aromatic, aliphatic, saturated or unsaturated, and combinations thereof. Typically, each R" is independently selected from hydrocarbyl groups, alkoxy and / or aryloxy groups, and siloxy groups, such as those represented by any one or combination of the [M], [D], [T], and / or [Q] units described above.

[0013] As introduced above, the composition includes a polysiloxane (A). As will be understood in light of the present description, polysiloxane (A) may be classified as or otherwise referred to as an MQ resin, where M, as introduced above, is a monofunctional siloxy unit (i.e., R"SiO 1 / 2 where R" represents a silicon-bonded substituent), and Q represents a tetrafunctional siloxy unit (i.e., SiO 4 / 2 ) Such MQ resins are known in the art as high molecular weight polymers composed primarily of M and Q units, and optionally a limited number of D and / or T units (e.g., ≦20 mol % in total), and typically exist in solid (e.g., powder or flake) form unless placed in a solvent. MQ resins are often represented by the general formula [M] x[In the formula, the subscript x indicates the molar ratio of the M siloxy unit to the Q siloxy unit when the molar number of the Q siloxy unit is normalized to 1]. It is simply specified by []. In such a case, the larger the value of x, the lower the crosslink density of the MQ resin. When the value of x decreases, the number of M siloxy units decreases, and thus, without terminating with the M siloxy unit, more Q siloxy units form a network, and vice versa. However, it will be understood that the normalized content of the Q siloxy unit does not imply or limit the MQ resin to only one Q unit. Rather, the MQ resin typically contains a plurality of Q siloxy units clustered or bonded together, as will be understood from the following description.

[0014] Typically, the polysiloxane (A) has the following general formula: (R 1 3SiO 1 / 2 ) a (R 2 2SiO 2 / 2 ) b (R’R 2 SiO 2 / 2 ) b’ (R 2 SiO 3 / 2 ) c (R’SiO 3 / 2 ) c’ (SiO 4 / 2 ) d and the subscripts a, b, b’, c, c’, and d are molar fractions such that a + b + b’ + c + c’ + d = 1, provided that 0 < a < 1, 0 ≤ b < 0.2, 0 ≤ b’ ≤ 0.1, 0 < c < 0.2, 0 ≤ c’ ≤ 0.1, 0 < d < 1, 0 ≤ b’ + c’ ≤ 0.1, the ratio of the subscript a to the subscript d is 0.5 to 1.5 (a:d), and each R 1 is independently selected from a hydrocarbyl group having 1 to 30 carbon atoms, -OH, and H, and each R 2 is independently R 1and -OX, where each X is independently H, a hydrocarbyl group R having 1 to 30 carbon atoms, or a polyether moiety as described below, and each R' comprises an independently selected amino group.

[0015] Referring to the general formula of polysiloxane (A) above, R 1Suitable hydrocarbyl groups include monovalent hydrocarbon moieties and derivatives and modifications thereof, which may be independently substituted or unsubstituted, linear, branched, cyclic, or combinations thereof, and saturated or unsaturated. With respect to such hydrocarbyl groups, the term "unsubstituted" refers to a hydrocarbon moiety composed of carbon and hydrogen atoms, i.e., containing no heteroatom substituents. The term "substituted" refers to a hydrocarbon moiety in which at least one hydrogen atom is replaced with an atom or group other than hydrogen (e.g., a halogen atom, an alkoxy group, an amine group, etc.) (i.e., as a pendant or terminal substituent), a carbon atom in the hydrocarbon chain / backbone is replaced with an atom other than carbon (e.g., a heteroatom such as oxygen, sulfur, nitrogen, etc.) (i.e., as part of the chain / backbone), or both. As such, suitable hydrocarbyl groups may include or be a hydrocarbon moiety having one or more substituents within and / or on (i.e., attached to and / or integral with) its carbon chain / backbone, such that the hydrocarbon moiety may include or be an ether, ester, etc. The linear and branched hydrocarbon groups can be independently saturated or unsaturated, and if unsaturated, can be conjugated or non-conjugated. The cyclic hydrocarbyl groups can be independently monocyclic or polycyclic and include cycloalkyl groups, aryl groups, and heterocycles, which can be aromatic, saturated and non-aromatic, and / or non-conjugated, etc. Examples of combinations of linear and cyclic hydrocarbyl groups include alkaryl groups, aralkyl groups, etc. Typical examples of hydrocarbon moieties suitable for use in or as hydrocarbyl groups include alkyl groups, aryl groups, alkenyl groups, alkynyl groups, halocarbon groups, etc., as well as derivatives, modifications, and combinations thereof. Examples of alkyl groups include methyl, ethyl, propyl (e.g., isopropyl and / or n-propyl), butyl (e.g., isobutyl, n-butyl, tert-butyl, and / or sec-butyl), pentyl (e.g., isopentyl, neopentyl, and / or tert-pentyl), hexyl, etc. (i.e., other linear or branched saturated hydrocarbon groups, e.g., having more than 6 carbon atoms).Examples of aryl groups include phenyl, tolyl, xylyl, naphthyl, benzyl, dimethylphenyl, etc., and derivatives and modifications thereof, which may overlap with alkaryl groups (e.g., benzyl) and aralkyl groups (e.g., tolyl, dimethylphenyl, etc.). Examples of alkenyl groups include vinyl, allyl, propenyl, isopropenyl, butenyl, isobutenyl, pentenyl, heptenyl, hexenyl, cyclohexenyl, etc., and derivatives and modifications thereof. Common examples of halocarbon groups include halogenated derivatives of the hydrocarbon moieties listed above, such as halogenated alkyl groups (e.g., any of the alkyl groups listed above in which one or more hydrogen atoms have been replaced with a halogen atom such as F or Cl), aryl groups (e.g., any of the aryl groups listed above in which one or more hydrogen atoms have been replaced with a halogen atom such as F or Cl), and combinations thereof. Examples of halogenated alkyl groups include 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, as well as derivatives and modifications thereof. Examples of halogenated aryl groups include chlorobenzyl, pentafluorophenyl, and fluorobenzyl, as well as derivatives and modifications thereof.

[0016] In certain embodiments, at least one R 1 is a substituted or unsubstituted hydrocarbyl group having 1 to 30 carbon atoms. For example, in certain embodiments, at least one R 1is an independently selected substituted or unsubstituted alkyl group, such as an alkyl group having 1 to 24, alternatively 1 to 18, alternatively 1 to 16, alternatively 1 to 12, alternatively 1 to 10, alternatively 1 to 8, or alternatively 1 to 6 carbon atoms. Specific examples of alkyl groups include methyl, ethyl, propyl (e.g., n-propyl and iso-propyl), butyl (e.g., n-butyl, sec-butyl, iso-butyl, and tert-butyl), pentyl, hexyl, heptyl, and the like, as well as derivatives and / or modifications thereof. Examples of derivatives and / or modifications of such alkyl groups include substituted versions thereof. For example, R 1 It will be understood that R may contain or be a hydroxylethyl group, which is a derivative and / or modification of the ethyl group described above. 1 can include, or be, an independently selected substituted or unsubstituted alkenyl group having 2 to 6 carbon atoms, e.g., 2 to 5, alternatively, 2 to 4, alternatively, 2 to 3 carbon atoms. In certain embodiments, polysiloxane (A) includes at least two R groups that include alkenyl functional groups. 1 groups (i.e., at least two R 1 is selected from substituted or unsubstituted alkenyl groups. In these or other embodiments, each R 1 are independently selected from H, —OH, a C1-C6 alkyl group, an aryl group, an alkenyl group, a phenyl group, a vinyl group, and combinations thereof. 1 At least 50 mole percent, alternatively at least 60 mole percent, alternatively at least 70 mole percent, alternatively at least 80 mole percent, alternatively at least 90 mole percent of the groups are hydrocarbyl groups.

[0017] Continuing to refer to the general formula of polysiloxane (A) above, each R 2 is independently R 1 and -OX, where each X is independently H (i.e., R 2 is a hydroxy group), the hydrocarbyl group R has 1 to 30 carbon atoms (i.e., R2 is a hydrocarbyloxy group of formula -OR), or a polyether moiety. When X is a hydrocarbyloxy group, the hydrocarbyl group R can be selected from any of the hydrocarbyl groups having 1 to 30 carbon atoms described above. Thus, examples of hydrocarbyloxy groups suitable for X include alkoxy groups and aryloxy groups. Examples of alkoxy groups include methoxy, ethoxy, propoxy, butoxy, benzyloxy, etc., as well as derivatives and modifications thereof. Examples of aryloxy groups include phenoxy, tolyloxy, pentafluorophenoxy, etc., as well as derivatives and modifications thereof. In some embodiments, each R 2 are independently 1 and -OR, where each R 1 are independently selected from H, —OH, and alkyl and aryl groups containing 1 to 30 carbon atoms, and each R is independently selected from alkyl and aryl groups containing 1 to 30 carbon atoms. In these or other embodiments, each R 2 is independently selected from -OH and -OR, where each R is independently selected from alkyl and aryl groups containing 1 to 30 carbon atoms.

[0018] As introduced above, in certain embodiments, at least one R 2 is of the formula -OX, where X is a polyether moiety. In these embodiments, the polyether moiety is not particularly limited and generally has the general formula (C n H 2n O) mwherein the subscript m is 1 to 50, and the subscript n is independently 2, 3, or 4 in each moiety represented by the subscript m. In certain embodiments, the subscript m is 1 to 45, e.g., 1 to 40, alternatively 1 to 30, alternatively 1 to 25, alternatively 1 to 20, or alternatively 1 to 15. In certain embodiments, the subscript m is at least 2, such that the polyoxyalkylene moiety can include one or more oxyalkylene units selected from oxyethylene units (e.g., —(C2H4O)—, i.e., the subscript n is 2), oxypropylene units (e.g., —(C3H6O)—, i.e., the subscript n is 3), and oxybutylene units (e.g., —(C4H8O)—, i.e., the subscript n is 4). When the oxyalkylene segment comprises one or more oxyalkylene units (i.e., is a polyoxyalkylene), the oxyalkylene units may be arranged in any manner, such as in a block form (e.g., an ordered block and / or a random block), a randomized form, or a combination thereof. In certain embodiments, the oxyalkylene segment comprises both oxyethylene units and oxypropylene units. In some such embodiments, the oxyalkylene segment is an oxyethylene-oxypropylene block copolymer.

[0019] The polyether portion may include one or more oxyalkylene segments. For example, in certain embodiments, X may be of the general formula -YR 3 (-[Y] j -Z) i wherein R 3 is a substituted or unsubstituted hydrocarbon segment, and each Y is a group having the general formula (C n H 2n O) m where Z is a terminal group, the subscript i is 0 to 8, and the subscript j is independently 0 or 1 in each moiety designated by the subscript i. 3is an at least divalent hydrocarbon linking group. More specifically, as used herein in this context, the hydrocarbon segment R 3 The valence of the oxyalkylene segment Y plus the subformula (-[Y] j -Z). Therefore, the hydrocarbon segment R 3 The valence of may be written as the subscript i+1.

[0020] Typically, each hydrocarbon segment R 3 independently comprise one or more substituted or unsubstituted hydrocarbon groups, i.e., hydrocarbon groups optionally modified or substituted with, for example, pendant alkoxy, carbonyl, siloxy, silyl, amino, amido, acetoxy, or aminoxy groups and / or internal O, N, or S atoms (i.e., in the backbone). For example, in some embodiments, polysiloxane (A) comprises at least one X corresponding to the general polyether moiety formula above, where the hydrocarbon segment R 3 In some such embodiments, the hydrocarbon segment R comprises, or is, a straight or branched chain hydrocarbon group having 3 to 30 carbon atoms, optionally containing one or more aromatic groups, ether groups, amine groups, or combinations thereof. 3 is a C1 to C20 hydrocarbon group. In these or other embodiments, each hydrocarbon segment R 3 independently comprise an aromatic group, an ether group, an amine group, or a combination thereof. As understood from the description herein, the hydrocarbon segment R 3 The ether and amine groups can be internal (e.g., containing an O atom or an N atom in the backbone of a straight or branched chain hydrocarbon group) or pendant (e.g., containing an alkoxy group or an amine group attached to the backbone of a straight or branched chain hydrocarbon group).

[0021] Each hydrocarbon segment R 3 may independently be linear or branched. More specifically, as will be understood from the description herein, R 3typically contains up to i branches (i.e., 0 to 8 branches), and the subscript j is a 3 1 for each branch from to the terminal group Z. In certain embodiments, each hydrocarbon segment R 3 comprises a branched chain hydrocarbon group having 3 to 16 carbon atoms. In some embodiments, each oxyalkylene segment Y independently has the formula (C2H4O) x (C3H6O) y (C4H8O) z wherein the subscript x is 1 to 50, the subscript y is 0 to 50, and the subscript z is 0 to 50, and wherein the units represented by the subscripts x, y, and z can be in a random or block form in the oxyalkylene segment.

[0022] In some embodiments, polysiloxane (A) comprises at least one X corresponding to the general polyether moiety formula above, where the subscript i is 0 and each hydrocarbon segment R 3 and independently comprise a linear or branched hydrocarbon group having 3 to 30 carbon atoms. In these or other embodiments, polysiloxane (A) comprises at least one X where the subscript i is 1, and the hydrocarbon segment R 3 comprises at least one group selected from linear or branched hydrocarbon groups having 3 to 30 carbon atoms, phenols, tetrahydrofurans, and alkylamines, each optionally substituted with one or more alkoxy groups. In these or other embodiments, polysiloxane (A) comprises at least one X where the subscript i is at least 2, and the hydrocarbon segment R 3 contains at least one group selected from a linear or branched hydrocarbon group having 3 to 30 carbon atoms, an alkylamine, a polyamine, a polyamide, a polyaziridine, a polyphenol, and a polyester.

[0023] Typically, each terminal group Z is independently selected from H (i.e., such that the polyether moiety is terminally hydroxy-functional) or a resinous silicone moiety (i.e., from the condensation of a terminal hydroxy functionality with a condensable silicon-bonded moiety of the polysiloxane (A)). For example, when the subscript i is at least 1, the terminal group Z may represent a crosslink to another silanol group of the polysiloxane (A). Similarly, when i>1, the polysiloxane (A) may contain one or more crosslinks. Those skilled in the art will understand that the presence of such crosslinks in the polysiloxane (A) in the composition, as well as the crosslink density, will depend on many factors, such as the hydroxyl (e.g., silanol) functionality of the selected silicone resin, the functionality of the selected polyether alcohol compound (B), the ratio of silicone resin to polyether alcohol compound (B) utilized to prepare the composition, and the degree of conversion, as described below with respect to the method. Similarly, the presence of such crosslinking can be confirmed by methods known in the art, for example, by rheological measurements of the gel point due to the increase in average molecular weight in response to crosslinking (i.e., the gel point indicates a weight average molecular weight that diverges toward infinity). For example, a rheometer (e.g., a rheometrics mechanical spectrometer using parallel plate geometry) can be used to perform frequency sweep experiments to determine changes in dynamic storage modulus, equilibrium modulus, and elastic modulus during the preparation of the composition. The full range of end groups Z, as well as the crosslinking potential of polysiloxane (A), will be better understood in view of the methods described herein.

[0024] Each R' independently comprises an amino group. In certain embodiments, each R' is an amino group. The amino group of R' has the formula -N(H) f R 2-fwherein each R is independently selected and defined above, i.e., each R is an independently selected hydrocarbyl group, and the subscript f is independently 0, 1, or 2. In other embodiments, each R' independently comprises a hydrocarbon group substituted with an amino group. Suitable hydrocarbon groups are those described above. In certain embodiments, each R' independently comprises an aliphatic hydrocarbon group substituted with an amino group. The aliphatic hydrocarbon group may be linear or cyclic and is typically saturated. In certain embodiments, each R' comprises an alkylamino group. For example, each R' is a group of the formula -(CH2) g N(H) f R 2-f where each subscript g is independently 1 to 30, alternatively 1 to 25, alternatively 1 to 20, alternatively 1 to 15, alternatively 1 to 10, alternatively 1 to 8, alternatively 1 to 6, alternatively 1 to 4, alternatively 2 to 4, and R' and subscript f are defined above. In certain embodiments, subscript g is 3 and subscript f is 2, such that each R' is of the formula -(CH)N(H).

[0025] With continued reference to the general formula for polysiloxane (A) above, the subscripts a, b, b', c, c', and d each represent a mole fraction such that a+b+b'+c+c'+d=1. As will be understood by those skilled in the art, the subscripts a, b, c, d, and e correspond to M, D, T, and Q siloxy units, respectively. The subscripts b and b' in the general formula above both refer to D siloxy units, and the subscripts c and c' in the general formula above both refer to T siloxy units, each with a different silicon-bonded substituent (R 2to R'). Generally, the ratio of each siloxy unit is selected such that 0 < a < 1, 0 ≤ b < 0.2, 0 ≤ b' ≤ 0.1, 0 < c < 0.2, 0 ≤ c' ≤ 0.1, 0 < d < 1, and 0 ≤ b' + c' ≤ 0.1, that is, polysiloxane (A) does not optionally contain D siloxy units (including those represented by subscripts b and / or b'), does not optionally contain T siloxy represented by subscript c', but contains at least one M, T, and Q siloxy unit each (represented by subscripts a, c, and d). However, in such embodiments, polysiloxane (A) generally has, in at least one, or most, or substantially all of the T siloxy units represented by subscript c, R 2 is configured to be -OX. Similarly, polysiloxane (A) does not optionally contain D siloxy units, but may contain a limited proportion of D siloxy units. However, typically, subscripts b and c together are less than 0.2 (i.e., b + c ≤ 0.2). In certain embodiments, subscript a is selected to be 0.3 to 0.6. In these or other embodiments, subscript d is selected to be 0.4 to 0.7. In certain embodiments, subscript c' is 0. In other embodiments, subscript c' is greater than 0 to 0.1, or greater than 0 to 0.05, or greater than 0 to 0.04, or 0.01 to 0.04. In other specific embodiments, subscript b' is 0. In still other embodiments, subscript b' is greater than 0 to 0.1, or greater than 0 to 0.05, or greater than 0 to 0.04, or 0.01 to 0.04. In further embodiments, b' and c' are each 0. In other embodiments, (b' + c') is greater than 0 to 0.1, or greater than 0 to 0.05, or greater than 0 to 0.04, or 0.01 to 0.04.

[0026] It will be understood that the subscripts a and d generally refer to the MQ resin portion of polysiloxane (A), and therefore the ratio of subscript a to subscript d can be used to characterize polysiloxane (A). For example, in some embodiments, the ratio of M siloxy units designated by subscript a to Q siloxy units designated by subscript d is 0.5 to 1.5 (a:d). In these or other embodiments, the ratio of M siloxy units designated by subscript a to Q siloxy units designated by subscript d is 0.7 to 1.2 (a:d).

[0027] As will be further understood from consideration of the following procedures, the characteristics and properties of polysiloxane (A) are selected and controlled by the particular components utilized in preparing the liquid silicone resin composition as a whole.

[0028] As introduced above, the composition also includes a polyether alcohol compound (B). Typically, the polyether alcohol compound (B) has the general formula HO-YR 3 (-[Y] j -H) i wherein each Y, R 3 , the subscript i, and the subscript j are as defined above. More specifically, R 3 is a substituted or unsubstituted hydrocarbon segment, each Y is an independently selected oxyalkylene segment, the subscript i is 0 to 8, and the subscript j is independently 0 or 1 in each moiety designated by the subscript i. Further description and examples of polyether alcohol compound (B) are provided below. However, as will be understood in more detail in view of the methods described herein, the Y and R in the general formula of polyether alcohol compound (B) 3 are the same groups (i.e., in terms of range) shown above for the polyether portion of polysiloxane (A). Thus, each Y and R 3 The descriptions of the moieties designated by the subscripts j and i apply equally to the conserved moieties of the formulas of both the polyether portion of the polysiloxane (A) and the polyether alcohol compound (B).

[0029] Generally, the polyether alcohol compound (B) comprises an alkoxylation reaction product of (b-1) a compound containing at least one alkoxylatable group (e.g., a functional group containing a labile hydrogen atom bonded to a nucleophilic O, N, or S atom, such as an -OH, -NH, or SH group) (i.e., an alkoxylatable compound (b-1)) and (b-2) an alkoxylating agent (e.g., an alkylene oxide, a polyoxyalkylene compound, etc.), which are described in order below. As will be understood by those skilled in the art, the alkoxylation reaction is not limited and is selected taking into consideration the specific alkoxylatable compound (b-1) and alkoxylating agent (b-2) used.

[0030] Typically, the alkoxylatable compound (b-1) is an organic alcohol, i.e., an organic compound comprising a carbon backbone and at least one hydroxyl (i.e., —OH) group. In such embodiments, the alkoxylatable compound (b-1) may be more specifically referred to as an alcohol compound (b-1). As will be understood in light of the following examples and explanations, the alcohol compound (b-1) may be a monool (i.e., containing only one hydroxyl functional group) or a polyol (i.e., containing at least two hydroxyl groups), such as a diol, triol, or the like. The carbon backbone of the alcohol compound (b-1) may be substituted or unsubstituted, for example, with any of the functional groups described herein. If substituted, the carbon backbone of the alcohol compound (b-1) may include pendant substitutions (i.e., in place of hydrogen atoms bonded to the carbon backbone) or substitutions of carbon atoms within the backbone itself (e.g., with other heteroatoms such as O, S, N, etc.). Thus, while alcohol compound (b-1) may be characterized or otherwise referred to as an organic alcohol, it should be understood that it may alternatively or further be defined in consideration of additional functional groups, if any, (e.g., as an amino alcohol, etc.) Furthermore, the carbon backbone may be linear or branched, and thus may include linear, branched, and / or cyclic hydrocarbon segments.

[0031] As will be understood in light of the present disclosure, the alcohol compound (b-1) is typically represented by the general formula HO-R 3 (-OH) i where R corresponds to 3 and the index i is as defined above. More specifically, R 3 is a hydrocarbon segment, and the subscript i is 0 to 8. In such embodiments, the hydrocarbon segment R 3 It will be understood that represents the carbon skeleton of the alcohol compound (b-1), which may contain 0 to 8 hydroxyl groups in addition to the required hydroxyl group, as indicated by the subscript i.

[0032] In certain embodiments, the subscript i is 0, such that the alcohol compound (b-1) has the general formula HO-R 3 In some such embodiments, R 3 may comprise or be a straight or branched chain hydrocarbon group having 3 to 30 carbon atoms. For example, in some embodiments, R 3 is a branched chain hydrocarbon group having 3 to 30 carbon atoms. In some such embodiments, the alcohol compound (b-1) has the formula:

[0033] [ka] In the formula, R 5 , R 6 , and R 7 are independently selected from C1 to C13 alkyl groups. For example, in some such embodiments, R 5 and R 6 are each independently selected from C1-4 alkyl groups, and R 7 is H or a C1-C13 alkyl group. In some of these embodiments, R 3 In some embodiments, R contains a total of 7 to 16 carbon atoms, e.g., 9 to 12 carbon atoms. 3contains a branching degree of at least 3. In this context, the term "branching degree" as used herein refers to the total number of methyl (-CH) groups minus 1. For example, an R 3 comprises a branching degree of 3. In some embodiments, R 5 is an alkyl group containing 3 to 12 carbon atoms, e.g., a C3-C8 alkyl group, or a C4-C6 alkyl group. In such embodiments, R 5 In these or other embodiments, R 6 is an alkyl group containing 3 to 12 carbon atoms, e.g., a C4 to C10 alkyl group, or a C6 to C8 alkyl group. In some embodiments, R 7 contains at least two methyl groups. For example, in certain embodiments, R 7 is a C1-C3 alkyl group. In another embodiment, R 7 is H. In some embodiments, R 5 is CH3(CH2)2CH(CH3)(CH2)2CH(CH3), and R 6 is H and R 7 is CH3. In certain embodiments, the alcohol compound (b-1) is (3-methyl-6-ethyl)-2-nonanol.

[0034] In certain embodiments, the subscript i is 1, such that the alcohol compound (b-1) has the general formula HO-R 3 -OH, where the hydrocarbon segment is a divalent linking group. In certain embodiments, for example, R 3 comprises or is an alkyl group (i.e., when the alcohol compound (b-1) is a glycol) or a substituted alkyl group (e.g., a diethylamino group when the alcohol compound (b-1) is diethanolamine), an aryl group (e.g., phenyl, benzyl, tolyl, etc.), a tetrahydrofuran group, or other difunctional materials such as those derived from epoxy adducts or ring opening of alkoxydiols.

[0035] In certain embodiments, the subscript i is ≧2, and thus the alcohol compound (b-1) may be further defined as a polyol, such as a triol, a tetraol, etc. In such embodiments, the alcohol compound (b-1) is exemplified by glycerol, pentaerythritol, sugar alcohols (e.g., sorbitol, xylitol, mannitol, etc.), and the like. In some such embodiments, R 3 includes or is selected from alkylamines, polyamines, polyamides, polyaziridines, polyphenols, and polyesters. 3 includes or is a phenol formaldehyde resin, an epoxy adduct of a glycidyl ether and a polyol, or an epoxy adduct of a glycidyl ether and a diamine or polyamine (e.g., a secondary diamine). In any of these embodiments, the subscript i can be from 2 to 8, such that the alcohol compound (b-1) contains from 2 to 8 hydroxyl groups, e.g., from 3 to 8, alternatively from 3 to 6, or alternatively from 3 to 5 hydroxyl groups.

[0036] It should be understood that other polyols and alcohols can be used as the alcohol compound (b-1) to similarly prepare the polyether alcohol compound (B). For example, in certain embodiments, the alcohol compound (b-1) is selected from polyether polyols, polyester polyols, polycarbonate polyols, acrylic polyols, polyols derived from isocyanate prepolymers (e.g., those having a functionality of 2 to 8), and the like.

[0037] The alkoxylating agent (b-2) is not limited and may be or include any alkoxylating compound suitable for replacing the alkoxylatable compound (b-1) to obtain the polyether alcohol compound (B) described herein. Typically, the alkoxylating agent (b-2) is selected from alkylene oxides, polyoxyalkylene compounds, and combinations thereof. For example, in certain embodiments, the alkoxylating agent (b-2) is selected from ethylene oxide, propylene oxide, butylene oxide, and combinations thereof. In other embodiments, the alkoxylating agent (b-2) is selected from polyoxyethylene, polyoxypropylene, polyoxybutylene, and combinations thereof (e.g., in the form of a random or block polymer). Those skilled in the art will understand that the term "alkoxylated" as used herein, for example, with respect to the precursors (b-1) and (b-2) of the polyether alcohol compound (B), can be considered functional and / or descriptive, and also includes ether / etherified products.

[0038] It will be understood by those skilled in the art that the number of hydroxyl groups present on the alkoxylatable compound (b-1) will affect the overall structure of the polyether alcohol compound (B) itself. In particular, the polyether alcohol compound (B) may contain polyoxyalkylene groups up to i=1, i.e., polyoxyalkylene groups from the alkoxylation of the alkoxylatable group(s) of the alcohol compound (b-1) with the alkoxylating agent (b-2).

[0039] For example, the general formula HO-YR 3 (-[Y] j -H) i With respect to the polyether alcohol compound (B) itself, each oxyalkylene segment Y independently has the formula (C2H4O) x (C3H6O) y (C4H8O) zwhere the subscript x is 1 to 50, the subscript y is 0 to 50, and the subscript z is 0 to 50, and the units represented by the subscripts x, y, and z may independently be in a randomized or block form in each oxyalkylene segment. In certain embodiments, in each oxyalkylene segment Y, the subscript x is 1 to 20, the subscript y is 0 to 20, and the subscript z is 0 to 20. In some such embodiments, x+y+z=1 to 50, e.g., 1 to 20, or 10 to 20. In certain embodiments, the subscript x is 2 to 20, and the subscripts y and z are both 0, such that the polyether alcohol compound (B) may be further defined as a polyoxyethylene alcohol.

[0040] In certain embodiments, the polyether alcohol compound (B) is a nonionic surfactant.For example, in some such embodiments, the polyether alcohol compound (B) can be selected from linear linear ethoxylates, branched ethoxylates (e.g., polyethylene glycol p-(1,1,3,3-tetramethylbutyl)-phenyl ether), amine ethoxylates (e.g., tertiary amine ethoxylates, fatty amine ethoxylates and / or propoxylates), ethoxylated, propoxylated, and / or butoxylated glycols, etc.

[0041] From the above description, in some embodiments, the polyether alcohol compound (B) has the general formula HO—(CHO) x (C3H6O) y (C4H8O) z -CR 5 R 6 R 7 wherein R 5 , R 6 , R 7 , and the subscripts x, y, and z are understood to be as defined above. In some such embodiments, for example, the subscript x is 1 to 40, the subscripts y and z are selected such that y+z=1 to 6, and R 5 and R 6are independently selected C1-C4 alkyl groups, and R 7 is H or C1-C13 alkyl. In some such embodiments, the subformula -CR 5 R 6 R 7 The moiety represented by the formula: contains a total of 7 to 16 carbon atoms and a degree of branching of at least 3.

[0042] In some embodiments, the polyether alcohol compound (B) has the formula:

[0043] [ka] In the formula, R 8 is H or isopropyl, and R 9 is CH3 or CH2CH3, the index y' is from 1 to 5, for example from 1 to 4, alternatively from 2 to 4, and the index x is from 2 to 30, such as from 2 to 20, alternatively from 2 to 10, alternatively from 2 to 9, alternatively from 5 to 9. In some of these embodiments, R 8 is H and R 9 is CH3, so that the polyether alcohol compound (B) has the formula:

[0044] [ka] where the subscripts y' and x are as defined above. In other embodiments, R 8 is isopropyl, so that the polyether alcohol compound (B) has the formula:

[0045] [ka] where the subscripts y' and x are as defined above.

[0046] Generally, polyether alcohol compound (B) can be prepared or otherwise obtained to have a narrow molecular weight distribution, expressed as the polydispersity index (PDI) (i.e., weight average molecular weight / number average molecular weight (Mw / Mn), as measured, for example, by gel permeation chromatography). For example, in certain embodiments, polyether alcohol compound (B) comprises a PDI of 1.15 or less, alternatively 1.1 or less. In certain embodiments, polyether alcohol compound (B) has a molecular weight (Mw) of less than 5,000, e.g., Mw of from 10 to less than 5,000, alternatively from 10 to 4,500, alternatively from 50 to 4,000, alternatively from 100 to 3,000, alternatively from 100 to 2,000.

[0047] In these or other embodiments, the polyether alcohol compound (B) contains low levels of residual unreacted alkoxylatable compound (b-1), such as alcohol compound (b-1) (i.e., non-alkoxylated alcohol). For example, in some embodiments, the polyether alcohol compound (B) contains less than 3 wt. %, alternatively less than 2 wt. %, alternatively 1 wt. % or less, alternatively 0.5 wt. % of residual / unreacted alcohol compound (b-1). In certain embodiments, the composition comprises one or more polyether alcohol compounds (B), such as a mixture of two, three, four, five, or more independently selected individual polyether alcohol compounds (B).

[0048] The amounts of components (A) and (B) in the composition may vary. In some embodiments, for example, the composition comprises 10 to 80 weight percent polysiloxane (A), based on the total weight of the composition. Similarly, in these or other embodiments, the composition comprises 10 to 95 weight percent polyether alcohol compound (B), based on the total weight of the composition. In certain embodiments, the composition comprises 10 to 80, alternatively 20 to 80, alternatively 20 to 70, alternatively 30 to 70 weight percent polysiloxane (A), based on the total weight of the composition. In these embodiments, the remainder of the composition may comprise only polyether alcohol compound (B), or may comprise a combination of polyether alcohol compound (B) and one or more additional components of the composition. For example, as better understood in view of the methods described below, the composition may comprise a catalyst, or a solvent or carrier vehicle. However, in some embodiments, the composition is free or substantially free of a catalyst. In these or other embodiments, the composition is free or substantially free of cyclic siloxanes. In these or other embodiments, the composition comprises less than 1 wt. % solvent, based on the total weight of the composition, hi other embodiments, the composition is free or substantially free of solvent or carrier vehicle (i.e., apart from component (B) itself).

[0049] In certain embodiments, the composition further comprises (C) an aminosilicon compound. Generally, the aminosilicon compound (C) is utilized to provide D siloxy units, if present, designated by subscript b, and / or T siloxy units, if present, designated by subscript c', in the polysiloxane (A), as described below with respect to the method of preparing the composition. The use of the aminosilicon compound (C) in preparing the polysiloxane (A) and / or the composition is optional. If used, some residual amount of the aminosilicon compound (C) may be present in the composition, i.e., the aminosilicon compound (C) may not be completely consumed in preparing the polysiloxane (A) and / or the composition.

[0050] The aminosilicon compound (C), when present, contains silicon-bonded substituents including amino groups which can be the substituents represented by R' in the polysiloxane (A). Typically, the aminosilicon compound (C) also contains silicon-bonded hydroxyl groups and / or hydrolyzable groups, such as alkoxy groups.

[0051] In certain embodiments, the aminosilicon compound (C) is an aminosilane, such as a compound of the formula R'R 10 h Si(OR 10 ) 3-h wherein the subscript h is 0 or 1, R′ is defined above, and each R 10 is an independently selected alkyl group having 1 to 18, alternatively 1 to 16, alternatively 1 to 14, alternatively 1 to 12, alternatively 1 to 10, alternatively 1 to 8, alternatively 1 to 6, alternatively 1 to 4 carbon atoms. In one embodiment, the subscript h is 0 and the amino silicon compound (C) has the formula R'Si(OR 10 )3. One specific example of such an aminosilane is 3-propylaminotriethoxysilane. In another embodiment, the subscript h is 1 and the aminosilicon compound (C) is of the formula R'R 10 Si(OR 10 ) 2. One specific example of such an aminosilane is 3-propylamino(diethoxy)methylsilane.

[0052] Amino silicon compounds (C) are used, having the formula R'Si(OR 10 ) 3, at least a portion of the amino silicon compound (C) used is generally hydrolyzed and condensed to form T siloxy units in the polysiloxane (A) indicated by the subscript c', i.e., the formula R'SiO 3 / 2Typically, each alkoxy group of the aminosilicon compound (C) is completely hydrolyzed and condensed to give such T siloxy units in the polysiloxane (A). When the aminosilicon compound (C) is used in preparing the polysiloxane (A), a partial condensate may be formed in the reaction intermediate of the polysiloxane (A). When the aminosilicon compound (C) is used, a compound having the formula R'Si(OR 10 )3, the partial condensation product is of the formula (R'(OZ) q SiO 3-q / 2 ) wherein the subscript q is independently 0, 1, or 2, and each Z is independently H or R 10 is.

[0053] An amino silicon compound (C) is used, having the formula R'R 10 Si(OR 10 ) 2, at least a portion of the amino silicon compound (C) used is generally hydrolyzed and condensed to form the D siloxy units in the polysiloxane (A) indicated by the subscript b', i.e., the compounds of the formula R'R 2 SiO 2 / 2 Typically, each alkoxy group of the aminosilicon compound (C) is completely hydrolyzed and condensed to give such D-siloxy units in the polysiloxane (A). When an aminosilicon compound is used in preparing the polysiloxane (A), a partial condensate may be formed in the reaction intermediate of the polysiloxane (A). When an aminosilicon compound (C) is used, a compound having the formula R'R 10 Si(OR 10 )2, the partial condensation product has the formula R'R 10 (OZ)rSiO 2-r / 2 wherein the subscript r is independently 0 or 1 and each Z is independently H or R 10 is.

[0054] A combination of different aminosilicon compounds may be utilized together as the aminosilicon compound (C).

[0055] The amino silicon compound (C) is typically present in the composition in an amount of from 0 to 25 wt %, alternatively from 0 to 20 wt %, alternatively from 0 to 15 wt %, based on the total weight of the composition.

[0056] As discussed above, the composition has a tunable liquid viscosity. In particular, the composition generally has a viscosity of 100 to 800,000 cps at 25°C. For example, in certain embodiments, the composition has a viscosity of 185 cps to 700,000 cps, depending on, for example, the specific polyether alcohol compound (B) selected, the ratio of polysiloxane (A) to polyether alcohol compound (B) used, the presence or absence of an amino silicon compound (C), and the like. Furthermore, as will be understood from the following method, the ratio of -OX=polyether moieties to -OX=H moieties (i.e., capping ratio) within polysiloxane (A) can also be independently selected and controlled to provide a liquid form of the composition. Because the composition has a tunable liquid viscosity, the viscosity can be selectively controlled based on the desired end use and its properties.

[0057] A method for preparing a liquid silicone resin composition is also disclosed. The method includes (I) combining a solid silicone resin, a polyether alcohol compound (B), and optionally an aminosilicon compound (C) together to obtain a mixture containing polysiloxane (A), polyether alcohol compound (B), and optionally an aminosilicon compound (C). The method also includes (II) liquefying the mixture containing polysiloxane (A) and polyether alcohol compound (B), thereby preparing the liquid silicone resin composition. As described below, in certain embodiments utilizing an aminosilicon compound (C), the aminosilicon compound (C) is incorporated during and / or after the step of liquefying the mixture.

[0058] As can be understood from the description herein, the polyether alcohol compound (B) can liquefy the solid silicone resin, optionally without reacting with the solid silicone resin.Therefore, the solid silicone resin is typically solid when combined with the polyether alcohol compound (B), as described below, optionally in the presence of a carrier vehicle.The term "solid" is used herein with respect to the solid silicone resin to describe a silicone that has a softening point and / or melting point higher than room temperature, so that the silicone resin is solid or substantially solid at room temperature.

[0059] 1. A solid silicone resin having the general formula: (R 1 3SiO 1 / 2 ) a (R 4 2SiO 2 / 2 ) b (R 4 SiO 3 / 2 ) c (SiO 4 / 2 ) d , In the formula, each R 4 is R 1 and -OR, with the proviso that R 4 is selected from —OH and —OR in at least one T siloxy unit designated by subscript c, and each R 1 , R, and the subscripts a, b, c, and d are as defined above.

[0060] With respect to the foregoing formula, as will be understood by those skilled in the art in light of the description herein, the solid silicone resin utilized in the present method forms the siloxane backbone of polysiloxane (A). Accordingly, the above description of the M, D, T, and Q siloxy units of polysiloxane (A), designated by the subscripts a, b, c, and d, respectively, applies equally to the solid silicone resin of the present method. For example, in certain embodiments, the solid silicone resin comprises an MQ ratio of 0.5 to 1.5, i.e., the ratio of M siloxy units designated by the subscript a to Q siloxy units designated by the subscript d (a:d). In these or other embodiments, the ratio of M siloxy units designated by the subscript a to Q siloxy units designated by the subscript d in the solid silicone resin is 0.7 to 1.2 (a:d). However, as is readily understood in the art, the ranges of the subscripts a, b, c, and d are applicable to both the solid silicone resin and the polysiloxane (A), but each of the subscripts a, b, c, and d can independently vary between the solid silicone resin and the polysiloxane (A). For example, when the method for preparing the composition includes liquefaction, certain siloxane bonds can be cleaved to obtain SiOZ moieties (where Z is independently H or alkyl). To this end, the polysiloxane (A) may have fewer Q siloxy units than the solid silicone resin, for example, on a mole fraction basis. For example, a Q siloxy unit in the solid silicone resin can cleave one siloxane bond, resulting in a T(OZ) siloxy unit in the polysiloxane (A) (i.e., a T siloxy unit having three siloxane bonds and an SiOZ group). The SiOZ groups may remain in the polysiloxane (A) or, if used, may condense with the polyether alcohol compound (B) and / or the amino silicon compound (C) to form functional groups (polyether groups and / or amino groups) in the polysiloxane (A). In certain embodiments, the solid silicone resin has an SiOZ content of SiOZ groups from greater than 0 to 10 wt%, alternatively from greater than 0 to 8 wt%, alternatively from greater than 0 to 6 wt%, alternatively from 0.5 to 4 wt%.

[0061] Typically, the solid silicone resin has a weight average molecular weight of 2,000 to 30,000, for example, 3,000 to 30,000, alternatively 4,000 to 30,000, alternatively 4,000 to 25,000, alternatively 5,000 to 25,000, alternatively 5,000 to 20,000, alternatively 6,000 to 20,000. As will be appreciated by those skilled in the art, weight average molecular weights can be readily determined in Daltons using triple detector gel permeation chromatography (e.g., with light scattering, refractive index, and viscosity detectors) against polystyrene standards.

[0062] It will be understood that the polyether alcohol compound (B) utilized in the present method (e.g., to cap and / or liquefy the polysiloxane (A)) is the same component as described above with respect to the polyether alcohol compound (B) of the composition, and therefore the above discussion of the polyether alcohol compound (B) and its various portions applies equally to the present method.

[0063] As introduced above, the method for preparing a liquid silicone resin composition includes combining a solid silicone resin, a polyether alcohol compound (B), and, optionally, any other components used (collectively, "process components") to prepare a mixture thereof. As will be understood by those skilled in the art, generally, no prior steps are required other than combining the reaction components together, although the specific processes described below may be used. Furthermore, while one embodiment of the method includes reacting a solid silicone resin with a polyether alcohol compound (B) (e.g., by a condensation reaction) to prepare a polysiloxane (A), thereby obtaining a composition, it should be understood that in another embodiment, the method may be used to prepare a composition by simply liquefying the polysiloxane (A) in the presence of the polyether alcohol compound (B) without reacting / capping the polysiloxane (A).

[0064] Furthermore, as mentioned above, an aminosilicon compound (C) may optionally be utilized in the present method. If used, the aminosilicon compound (C) can be incorporated at any point in the process for preparing the composition. For example, in one embodiment, the aminosilicon compound (C) is combined with the solid silicone resin and the polyether alcohol compound (B) so that the aminosilicon compound (C) is present in the mixture. Alternatively, or in addition, the aminosilicon compound (C) can be combined with the mixture after its formation. Furthermore, the aminosilicon compound (C) can be combined during and / or after liquefaction of the mixture, as described below.

[0065] Regarding the process components, the solid silicone resin may be prepared or obtained by other methods, i.e., as a prepared resin. Methods for preparing MQ resins, such as solid silicone resins, are known in the art, and suitable precursors and suitable starting materials are commercially available from various suppliers. When the solid silicone resin is part of the process, the preparation is typically carried out before combining the solid silicone resin with the polyether alcohol compound (B). The polyether alcohol compound (B) may also be prepared as part of the process, or may be obtained for use in the process by other methods. In certain embodiments, the polyether alcohol compound (B) is prepared by reacting (e.g., alkoxylating) an alkoxylatable compound (b-1) with an alkoxylating agent (b-2). When selecting an alkoxylating agent (b-2), for example, when an alkylene oxide is utilized, one skilled in the art will understand that propylene oxide and / or butylene oxide may be used to modify the viscosity by increasing the flexibility of the product of the alkoxylation and / or condensation reaction of the present method, thereby increasing the flowability of the polyether alcohol compound (B) and, optionally, the polysiloxane (A) prepared therewith.

[0066] Typically, the process components are combined in a vessel or reactor to prepare the composition. The process components may be fed into the vessel together or separately, or may be dispensed into the vessel in any order and in any combination, as exemplified below. The process may further include, for example, stirring the mixture to promote mixing and contact of the process components when combined. Such contact may independently use other conditions with (e.g., simultaneously or sequentially) or without (i.e., independent of or in place of) stirring, and are typically carried out to aid in the preparation of polysiloxane (A) in the mixture and / or liquefaction of the mixture. Other conditions may be utilized in addition to or in place of the conditions described herein, and may be consequently effective conditions for promoting condensation, liquefaction, etc., during the course of the process.

[0067] The present method can utilize any amount of the method components, and more specifically, can include combining the solid silicone resin, polyether alcohol compound (B), and optionally the amino silicon compound (C) in various amounts or ratios depending on the desired properties of the resulting composition and / or the characteristics of the starting materials used. For example, the solid silicone resin and polyether alcohol compound (B) can be utilized in amounts configured to provide a specific capping ratio (i.e., the molar ratio of silanol functional groups of the MQ resin to the hydroxyl functional groups of the polyether alcohol compound (B)) of the polysiloxane (A) prepared therewith (e.g., a capping ratio of 0.25 to 1.0, e.g., 0.5 to 0.75). Thus, as will be understood by those skilled in the art, the solid silicone resin and polyether alcohol compound (B) can be utilized in a molar ratio of 1:≧1, depending on the advantage of either component. For example, the solid silicone resin and polyether alcohol compound (B) can be utilized in a molar ratio of 1:10 to 10:1, alternatively 1:5 to 5:1, alternatively 1:2 to 2:1, alternatively 1:1.1 to 1.1:1. As indicated, an excess (e.g., a slight excess, a moderate excess, or a total excess) of either component can also be utilized.

[0068] The solid silicone resin, polyether alcohol compound (B), and optionally the amino silicon compound (C) can be combined in any order, optionally under shear or mixing. For example, in some embodiments, a mixture is prepared by combining the solid silicone resin and the polyether alcohol compound (B) together, and optionally utilizing any additional components, such as the amino silicon compound (C). The components can be combined in any order, simultaneously, or in any combination thereof (e.g., in various multi-part compositions that are ultimately combined with each other). Similarly, the mixture can be prepared in a batch, semi-batch, semi-continuous, or continuous process, unless otherwise specified herein. Typically, once combined, the components of the mixture are homogenized, for example, by mixing, which can be carried out by any of a variety of techniques known in the art using any equipment suitable for mixing. Examples of suitable mixing techniques generally include ultrasonication, dispersive mixing, planetary mixing, three-roll milling, etc. Examples of mixing equipment include stirred batch kettles for relatively high fluidity (low dynamic viscosity) compositions, ribbon blenders, solution blenders, co-kneaders, twin rotor mixers, Banbury-type mixers, pulverizers, extruders, and the like, which may be batch-type or continuous compounding type equipment, utilized alone or in combination with one or more mixers of the same or different types.

[0069] In some embodiments, the solid silicone resin, polyether alcohol compound (B), and optionally the amino silicon compound (C) are combined in the presence of a carrier vehicle. The carrier vehicle is not limited and is typically selected based on the particular solid silicone resin and / or polyether alcohol compound (B) used, the desired end use of the composition, etc. Generally, the carrier vehicle includes or is a solvent, a fluid, an oil (e.g., an organic oil and / or a silicone oil), etc., or a combination thereof.

[0070] In some embodiments, the carrier vehicle comprises a silicone fluid. The silicone fluid is typically a low viscosity and / or volatile siloxane. In some embodiments, the silicone fluid is a low viscosity organopolysiloxane, a volatile methyl siloxane, a volatile ethyl siloxane, a volatile methylethyl siloxane, or the like, or a combination thereof. Typically, the silicone fluid has a viscosity of 1 to 1,000 mm at 25°C. 2 Specific examples of suitable silicone fluids include hexamethylcyclotrisiloxane, octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, dodecamethylcyclohexasiloxane, octamethyltrisiloxane, decamethyltetrasiloxane, dodecamethylpentasiloxane, tetradecamethylhexasiloxane, hexademethylheptasiloxane, heptamethyl-3-{(trimethylsilyl)oxy)}trisiloxane, hexamethyl-3,3,

[0033] Further examples of suitable silicone fluids include 5x10 methylsiloxane, 5x10 methylsiloxane, 5x10 octylsiloxane, 5x10 octyltri ... -7 ~1.5×10 -6 m 2 Examples of suitable polyorganosiloxanes include polyorganosiloxanes having a suitable vapor pressure of 1000 psi / sec.

[0071] In certain embodiments, the carrier vehicle comprises an organic fluid, typically comprising organic oils containing volatile and / or semi-volatile hydrocarbons, esters, and / or ethers. Common examples of such organic fluids include C6-C8 16 Alkanes, C8-C 16 Isoalkanes (e.g., isodecane, isododecane, isohexadecane, etc.), C8 to C 16Included are volatile hydrocarbon oils such as branched esters (e.g., isohexyl neopentanoate, isodecyl neopentanoate, etc.), as well as derivatives, modifications, and combinations thereof. Additional examples of suitable organic fluids include aromatic hydrocarbons, aliphatic hydrocarbons, alcohols having four or more 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 ), and hydrogenated polydecene. 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), octyldodecyl neopentanoate, diisobutyl adipate, diisopropyl adipate, propylene glycol dicaprylate / dicaprate, octyl ether, octyl palmitate, and combinations thereof. It will be understood that some of the above examples of organic fluids (e.g., glycol ethers) may overlap with the polyether alcohol compound (B), which may be utilized as a carrier vehicle by itself or in combination with another carrier vehicle described herein. In some embodiments, the method is carried out in the absence or substantially absence of organic fluids meeting the description of polyether alcohol compound (B) (i.e., other than polyether alcohol compound (B) itself).

[0072] In some embodiments, the carrier vehicle comprises an organic solvent. Examples of organic solvents include alcohols such as methanol, ethanol, isopropanol, butanol, and n-propanol; ketones such as acetone, methyl ethyl ketone, or methyl isobutyl ketone; aromatic hydrocarbons such as benzene, toluene, and xylene; aliphatic hydrocarbons such as heptane, hexane, and octane; halogenated hydrocarbons such as dichloromethane, 1,1,1-trichloroethane, and chloroform; dimethyl sulfoxide; dimethylformamide, acetonitrile; tetrahydrofuran, white spirit; mineral spirits, naphtha; n-methylpyrrolidone, and the like, as well as derivatives, modifications, and combinations thereof. In certain embodiments, the carrier vehicle comprises a polar organic solvent, such as a water-compatible solvent. Specific examples of such polar organic solvents utilized in certain embodiments include methanol, ethanol, 1-propanol, 2-propanol, 2-methyl-2-propanol, 2-butanone, tetrahydrofuran, acetone, and combinations thereof. Other carrier vehicles may also be utilized instead of, in addition to, or in combination with those described herein. In certain embodiments, the carrier vehicle comprises or is an aliphatic and / or aromatic hydrocarbon solvent such as xylene, a siloxane solvent such as hexamethylenedisiloxane (HMDSO), D4 or D5 cyclics or other such siloxanes, or a combination thereof. In other embodiments, the method is carried out substantially free of certain solvents. For example, in some embodiments, the method is carried out free of, or substantially free of, hexamethylenedisiloxane (HMDSO), D4 cyclics, and / or D5 cyclics. In these or other embodiments, the method is carried out free of, or substantially free of, benzene, toluene, ethylbenzene, and xylene (i.e., BTEX solvents). In these or other embodiments, the method is carried out free of, or substantially free of, aromatic solvents.

[0073] In certain embodiments, the solid silicone resin is combined with the carrier vehicle before being combined with the polyether alcohol compound (B) and optionally the aminosilicon compound (C). However, in other embodiments, the polyether alcohol compound (B) is combined with the carrier vehicle before being combined with the solid silicone resin (and optionally the aminosilicon compound (C)), or the components are combined substantially simultaneously to provide the mixture. Parameters related to the conditions under which these components are combined (e.g., temperature, pressure, etc.) can also be controlled. However, the method can also be carried out at ambient conditions. Typically, the solid silicone resin, the polyether alcohol compound (B), optionally the aminosilicon compound (C), and the carrier vehicle are combined together at a temperature below 45°C (i.e., low-temperature processing) to provide the mixture. However, in some embodiments, the solid silicone resin, polyether alcohol compound (B), optionally the amino silicon compound (C), and carrier vehicle are combined together at a temperature below 40°C, alternatively below 35°C, alternatively below 30°C, or at or near ambient temperature.

[0074] In some embodiments, the method includes reacting a solid silicone resin with a polyether alcohol compound (B) to prepare a polysiloxane (A) in the mixture. In these or other embodiments, in methods utilizing an aminosilicon compound (C), the method may further include reacting a solid silicone resin or a reaction intermediate formed by reacting a solid silicone resin with a polyether alcohol compound (B) with the aminosilicon compound (C) to prepare polysiloxane (A). Generally, the aminosilicon compound (C) hydrolyzes and condenses to provide T siloxy units having amino functionality in polysiloxane (A). As introduced above, the reaction in the method can be generally defined as a condensation reaction or can be otherwise characterized, and certain parameters and conditions of the reaction can be selected by one skilled in the art taking into account the particular components utilized. For example, in some such embodiments, the method includes disposing a catalyst (i.e., a condensation catalyst) in the mixture. Condensation catalysts, such as those based on tin (e.g., Sn octoate) or bases (e.g., NaOAc, KOH, etc.), are known in the art and are selected based on the process components utilized. However, in other embodiments, the process is carried out in the absence of any tin catalyst, for example, to provide the composition as a tin-free product, thereby avoiding limitations associated with tin being carried over into the final composition.

[0075] When used in the present method, the catalyst can be used in any amount, which can be selected by those skilled in the art and is based on, for example, the specific catalyst selected, the concentration / amount of its active catalytic species, the nature / type of the selected solid silicone resin and / or polyether alcohol compound (B), the reaction parameters used, the scale of the reaction (e.g., the total amount of process components used, etc.). The molar ratio of catalyst to process components can affect the rate and / or amount of condensation to prepare polysiloxane (A) in the mixture. Therefore, the amount of catalyst relative to the process components and the molar ratio therebetween can vary. Typically, these relative amounts and molar ratios are selected to maximize the reaction of the process components while minimizing the catalyst loading (e.g., to increase the economic efficiency of the reaction, increase the ease of purifying the reaction product formed, etc.).

[0076] In certain embodiments, the catalyst is utilized in the reaction in an amount of 0.000001 to 50 weight percent (i.e., weight / weight), based on the total amount of solid silicone resin utilized. For example, the catalyst may be used in an amount of 0.000001 to 25, alternatively 0.00001 to 10, alternatively 0.0001 to 5 weight percent, based on the total amount of solid silicone resin utilized. In some embodiments, the catalyst is utilized in an amount sufficient to provide a ratio of catalytic tin to hydrolyzable groups of the solid silicone resin compound of 1:10 to 1:1,000,000, alternatively 1:50 to 1:1,000, alternatively 1:100 to 1:500. Such ratios may be weight ratios (i.e., weight / weight) or may be molar ratios between the components. It will be understood that amounts and ratios outside the ranges recited above may also be utilized. For example, the catalyst may be utilized in a stoichiometric amount (i.e., a supercatalytic amount), based, for example, on the total amount of polyether alcohol compound (B) used in the mixture.

[0077] The catalyst can be prepared or obtained otherwise (i.e., as a prepared compound). Methods for preparing condensation catalysts (e.g., tin catalysts, acetate catalysts, etc.) using commercially available compounds from various suppliers are known in the art. Thus, the catalyst can be prepared before the reaction of the solid silicone resin with the polyether alcohol compound (B) (and optionally the amino silicon compound (C)), or in situ (i.e., during the reaction of these components, for example, by combining the catalyst components with a mixture containing the solid silicone resin and the polyether alcohol compound (B)). As such, in certain embodiments, the catalyst is prepared as part of a preparation method, i.e., the preparation method includes preparing the catalyst.

[0078] If a condensation reaction is desired, the method typically further includes exposing the mixture to one or more condensation conditions (e.g., elevated temperature, reduced pressure, reflux, etc.). As such, the vessel or reactor may be heated or cooled in any suitable manner (e.g., via a jacket, mantle, exchanger, bath, coil, etc.) to allow the reaction to be carried out at elevated or reduced temperatures, pressures, etc., as described below. For example, depending on the nature of the condensation reaction, the condensation conditions may include heating the mixture to an elevated temperature, such as 100°C, to promote condensation of the polyether alcohol compound (B) and the solid silicone resin (and optionally the amino silicon compound (C)). Similarly, the condensation conditions may include drawing a vacuum on the reactor, which is utilized to subject the mixture to reduced pressure (e.g., 35 to 300 mbar). In combination, the reduced pressure and elevated temperature may be utilized to distill water from the reaction, thereby driving the condensation toward completion by preventing the reverse reaction. Those skilled in the art will appreciate that the particular temperature and pressure utilized will be selected based on the process components and carrier vehicle present in the mixture, e.g., to provide efficient reflux conditions without overheating the mixture. For example, in various embodiments, the reaction is carried out at a reaction / condensation temperature of 23-200°C, e.g., from above ambient temperature (e.g., above 25°C) to 200°C, alternatively from above 25 to 180°C, alternatively from above 25 to 165°C, alternatively from above 25 to 150°C, alternatively from 30 to 150°C, alternatively from 50 to 150°C, alternatively from 70 to 150°C, alternatively from 60 to 150°C, alternatively from 85 to 150°C, alternatively from 100 to 150°C, alternatively from 110 to 150°C. In certain embodiments, the reaction temperature is selected and / or controlled based on the boiling point of any one solvent or volatile diluent, such as when reflux conditions are utilized. Additionally, a co-solvent, such as toluene, may be used to azeotrope water from the mixture.

[0079] Generally, the reaction rate of the components in the mixture (i.e., the condensation of the polyether alcohol compound (B) and the solid silicone resin, and optionally the amino silicon compound (C)) increases as i) the reaction temperature increases and ii) water is removed from the reaction system. Therefore, the required reaction time is selected taking into account the specifics of the mixture being reacted. In exemplary embodiments, the reaction time (i.e., the condensation / capping time, which may be monitored by visual inspection, spectroscopy (e.g., NMR, FT-IR, etc.), or other methods known in the art) may be on the order of one to several hours, such as 1 to 10 hours, alternatively 2 to 10 hours, alternatively 3 to 10 hours, alternatively 4 to 10 hours, alternatively 4 to 8 hours, or alternatively 4 to 6 hours. However, both longer and shorter reaction times may be selected taking into account, for example, the scale of the reaction and any particular components utilized in the mixture.

[0080] In certain embodiments, the method includes dissolving a solid silicone resin in a carrier vehicle (i.e., a solvent) to obtain a silicone resin solution, and combining the silicone resin solution with a polyether alcohol compound (B) to form a mixture. As discussed above, when the method utilizes an aminosilicon compound (C), the aminosilicon compound (C) can be combined with the silicone resin and / or the mixture. In these embodiments, for example, when a carrier vehicle is utilized, the method typically further includes removing the carrier vehicle from the mixture once the polysiloxane (A) has been prepared therein. More specifically, in such embodiments, liquefying the mixture includes solvent-exchanging the solid silicone resin from the solvent / carrier vehicle into the polyether alcohol compound (B), thereby preparing the composition. The solvent exchange is not particularly limited and may simply include removing the carrier vehicle from the reactor (e.g., by distillation). For example, in certain embodiments, the method includes heating the mixture to a temperature of 60-150°C under reduced pressure (i.e., about 35 mbar) to remove the solvent and obtain the composition.

[0081] As will be appreciated from the above description and examples herein, the compositions prepared by the present method provide a liquefied combination of polysiloxane (A) and polyether alcohol compound (B), and optionally, if utilized and not completely consumed, residual amino silicon compound (C). Polysiloxane (A) may comprise the condensation reaction product of a solid silicone resin with polyether alcohol compound (B) (and optionally, the amino silicon compound), or may simply be a liquefied form of a solid silicone resin (e.g., when capping / condensation with polyether alcohol compound (B) does not occur).

[0082] The following examples, which represent embodiments of the present disclosure, are intended to illustrate, but not limit, the present invention. Unless otherwise specified, all reactions were carried out under air, and all solvents, substrates, and reagents were purchased from various commercial suppliers (e.g., Gelest, Acros, Sigma-Aldrich) or otherwise obtained and utilized as received.

[0083] Instrumentation and Characterization Parameters The following instruments and characterization procedures / parameters are used to evaluate various physical properties of the compounds and compositions prepared in the examples below.

[0084] Gel Permeation and Size Exclusion Chromatography (GPC / SEC) SEC Instrumentation SEC is performed on a Waters 2695 LC pump and autosampler with a flow rate set at 1 mL / min and an injection volume set at 100 μL. SEC separation is performed on two Agilent Plgel Mixed-D columns, each held at 35°C, using a Shodex RI-201 refractive index detector.

[0085] Sample preparation The sample is prepared in THF eluent at a concentration of approximately 5 mg / mL polymer / resin. The solution is shaken on a flat-bed shaker at ambient temperature for approximately 2 hours, then filtered through a 0.45 μm PTFE syringe filter before injection.

[0086] Processing the data Agilent GPC software Cirrus version 3.3 was used for data collection and data reduction. A total of 16 polystyrene (PS) linear narrow molecular weight standards from Agilent with Mp values ​​ranging from 3752 to 0.58 kg / mol were used for molecular weight calibration. A third-order polynomial was used for calibration curve fitting, providing reference to all molecular weight averages, distributions, and molecular weights as PS equivalent values.

[0087] FT-IR analysis The details of the FT-IR instrumentation are given in Table 1 below.

[0088] [Table 1]

[0089] Sample preparation Sample Spectrum: The sample is weighed into a stoppered 1 cm IR quartz cuvette. A specific amount of CCl4 is added to the cuvette and the sample is mixed thoroughly by shaking. The sample is then measured by IR using the spectral parameters listed below.

[0090] Reference spectrum: Following sample measurement, approximately 0.5 mL of DO is added to the cuvette and the sample is mixed vigorously for approximately 30 seconds before being allowed to phase separate. The top DO layer is removed and the addition / mixing procedure is repeated to ensure complete DO exchange. The sample is again allowed to phase separate, leaving the DO in place. The sample is then measured again by IR (deuterated sample).

[0091] Processing the data Spectral subtraction: The deuterated sample spectrum is subtracted from the original sample spectrum to remove invariant features. The subtraction result is -1If the spectrum of water in CCl4 showed a discernible interference of the water signal in CCl4 (i.e., if there was little or no -COH present), the spectrum of water in CCl4 was subtracted from the original subtraction.

[0092] After subtraction, 3690cm -1 The maximum peak height of the band is measured and the result is used in the following calculation to determine the ppm OH of the silanol signal.

[0093]

number

[0094] Viscosity measurement Brookfield Instrumentation A Brookfield DV3T cone / plate rheometer maintained at 25° C. by water recirculation is utilized with a CPA-40Z spindle and 0.50 mL material volume for the measurements.

[0095] Sample preparation and procedures A method based on ASTM D 4287 is utilized using a horizontal viscometer. For each series of samples, the required parameters are entered into the digital viscometer and the position of the sample cup is adjusted relative to the spindle (cone) as specified by the manufacturer to maintain the required clearance. The sample cup is removed and 0.5 mL of sample is added to the center of the cup using a 1 mL syringe, ensuring all air bubbles are eliminated from the material. The sample is allowed to equilibrate at 25 + / - 0.1°C. The motor is started at a specific speed and the digital readout of viscosity is recorded. Prior to taking samples, the instrument is calibrated using Standard 200 Fluid (with a viscosity close to that of the sample, if possible) as a control.

[0096] 29 Si NMR 29 For Si NMR, 2.5-3 g of each product prepared below and approximately 5 g of solvent (CDCl3 + Cr(acac)3) were loaded into a 16 mm silicon-free NMR tube, and spectra were obtained according to the conditions and instruments in Table 2 below.

[0097] [Table 2]

[0098] material Table 3 below provides a brief summary and provides information about certain abbreviations, shorthand notations, and components used in the examples.

[0099] [Table 3]

[0100] Example 1 246.7 g of silicone resin 1 and 79.93 g of polyether alcohol 1 were placed in a 1000 mL four-neck flask. 0.15 g of condensation catalyst 1 was added, and the contents were adjusted to 50 wt% solids (SR + PA) by adding xylene (total weight = 506.7 g). The flask was mixed with an overhead stirrer at 200 rpm and then heated to 80°C for 15 minutes. A Dean-Stark trap was attached to the flask, and the contents were refluxed at 140°C for 4 hours, collecting the reaction water. The flask was cooled to room temperature and rotary evaporated under vacuum at 100°C to remove the xylene. The resulting product was clear and had a Brookfield viscosity of 1800 cps. A sample was analyzed by GPC, Si NMR, and FT-IR. The resulting product had a resin content of approximately 68%.

[0101] Example 2 226.0 g of silicone resin 1 and 93.75 g of polyether alcohol 2 were placed in a 1000 mL four-neck flask. 0.15 g of condensation catalyst 1 was added, and the contents were adjusted to 50 wt% solids (SR + PA) by adding xylene (total weight = 506.1 g). The flask was mixed with an overhead stirrer at 200 rpm and then heated to 80°C for 15 minutes. A Dean-Stark trap was attached to the flask, and the contents were refluxed at 140°C for 4 hours, collecting the reaction water. The flask was cooled to room temperature and rotary evaporated under vacuum at 100°C to remove the xylene. The resulting product was clear and had a Brookfield viscosity of 1386 cps. A sample was analyzed by GPC, Si NMR, and FT-IR. The resulting product had a resin content of approximately 63%.

[0102] Example 3 760.5 g of silicone resin 2 and 223.7 g of polyether alcohol 1 were placed in a 1500 mL four-neck flask. 0.3 g of condensation catalyst 1 was added, and the contents were adjusted to 75 wt% solids (SR + PA) by adding xylene (total weight = 1018.5 g). The flask was mixed with an overhead stirrer at 200 rpm and then heated to 80°C for 15 minutes. A Dean-Stark trap was attached to the flask, and the contents were refluxed at 140°C for 4 hours, collecting the reaction water. The flask was cooled to room temperature and rotary evaporated under vacuum at 100°C to remove the xylene. The resulting product was clear and had a Brookfield viscosity of 63,500 cps. A sample was analyzed by GPC, Si NMR, and FT-IR. The resulting product had a resin content of approximately 70%.

[0103] Example 4 702.5 g of silicone resin 2 and 263.8 g of polyether alcohol 2 were placed in a 1500 mL four-neck flask. 0.3 g of condensation catalyst 1 was added, and the contents were adjusted to 75 wt% solids (SR + PA) by adding xylene (total weight = 1017.1 g). The flask was mixed with an overhead stirrer at 200 rpm and then heated to 80°C for 15 minutes. A Dean-Stark trap was attached to the flask, and the contents were refluxed at 140°C for 4 hours, collecting the reaction water. The flask was cooled to room temperature and rotary evaporated under vacuum at 100°C to remove the xylene. The resulting product was clear and had a Brookfield viscosity of 15,600 cps. A sample was analyzed by GPC, Si NMR, and FT-IR. The resulting product had a resin content of approximately 65%.

[0104] Example 5 330.5 g of silicone resin 1 and 122.2 g of polyether alcohol 4 were placed in a 1000 mL four-neck flask. 0.15 g of condensation catalyst 1 was added, and the contents were adjusted to 70 wt% solids (SR + PA) by adding xylene (total weight = 508.9 g). The flask was mixed with an overhead stirrer at 200 rpm and then heated to 80°C for 15 minutes. A Dean-Stark trap was attached to the flask, and the contents were refluxed at 140°C for 4 hours, collecting the reaction water. The flask was cooled to room temperature and rotary evaporated under vacuum at 100°C to remove the xylene. The resulting product was clear and had a Brookfield viscosity of 1762 cps. A sample was analyzed by GPC, Si NMR, and FT-IR. The resulting product had a resin content of approximately 65%.

[0105] Example 6 322.7 g of silicone resin 1 and 127.3 g of polyether alcohol 5 were placed in a 1000 mL four-neck flask. 0.15 g of condensation catalyst 1 was added, and the contents were adjusted to 70 wt% solids (SR + PA) by adding xylene (total weight = 508.8 g). The flask was mixed with an overhead stirrer at 200 rpm and then heated to 80°C for 15 minutes. A Dean-Stark trap was attached to the flask, and the contents were refluxed at 140°C for 4 hours, collecting the reaction water. The flask was cooled to room temperature and rotary evaporated under vacuum at 100°C to remove the xylene. The resulting product was clear and had a Brookfield viscosity of 46,400 cps. A sample was analyzed by GPC, Si NMR, and FT-IR. The resulting product had a resin content of approximately 64%.

[0106] Example 7 58.5 g of silicone resin 1, 57.4 g of polyether alcohol 3, and 25.6 g of polyether alcohol 6 were placed in a 500 mL four-neck flask. 0.19 g of condensation catalyst 1 was added, and the contents were adjusted to 70 wt% solids (SR + PA) by adding xylene (total weight = 141.8 g). The flask was mixed with an overhead stirrer at 200 rpm and then heated to 80°C for 15 minutes. A Dean-Stark trap was attached to the flask, and the contents were refluxed at 140°C for 4 hours, collecting the reaction water. The flask was cooled to room temperature and rotary evaporated under vacuum at 100°C to remove the xylene. The resulting product was clear and had a Brookfield viscosity of 185 cps. A sample was analyzed by GPC, Si NMR, and FT-IR. The resulting product had a resin content of approximately 41%.

[0107] Example 8 436 g of silicone resin 1 and 2574.9 g of polyether alcohol 7 were placed in a 5000 mL four-neck flask. 0.9 g of condensation catalyst 1 was added, and the contents were adjusted to 45 wt% solids (SR + PA) by adding xylene (total weight = 3013.5 g). The flask was mixed with an overhead stirrer at 200 rpm and then heated to 80°C for 15 minutes. A Dean-Stark trap was attached to the flask, and the contents were refluxed at 140°C for 4 hours, collecting the reaction water. The flask was cooled to room temperature and rotary evaporated under vacuum at 100°C to remove the xylene. The resulting product was clear to hazy and had a Brookfield viscosity of 185 cps. Samples were analyzed by GPC, Si NMR, and FT-IR. The resulting product had a resin content of approximately 10%.

[0108] Example 9 291 g of Silicone Resin 1 and 716.6 g of Polyether Alcohol 7 were placed in a 2000 mL four-neck flask. No condensation catalyst was added. The contents were adjusted to 90 wt% solids (SR+PA) by adding xylene (total weight = 1007.6 g). The flask was mixed at 200 rpm using an overhead stirrer and then heated to 60°C for 15 minutes. The flask was cooled to room temperature and rotary evaporated under vacuum at 100°C to remove the xylene. The resulting product was clear and had a Brookfield viscosity of 185 cps. A sample was analyzed by GPC, Si NMR, and FT-IR. The resulting product had a resin content of approximately 20%.

[0109] Example 10 246.8 g of Silicone Resin 1 and 704.1 g of Polyether Alcohol 8 were placed in a 2000 mL four-neck flask. No condensation catalyst was added. The contents were adjusted to 90 wt% solids (SR+PA) by adding xylene (total weight = 950.8 g). The flask was mixed at 200 rpm using an overhead stirrer and then heated to 60°C for 15 minutes. The flask was cooled to room temperature and rotary evaporated under vacuum at 100°C to remove the xylene. The resulting product was clear and had a Brookfield viscosity of 185 cps. A sample was analyzed by GPC, Si NMR, and FT-IR. The resulting product had a resin content of approximately 20%.

[0110] GPC and FT-IR analysis of Examples 1-10. The results of GPC and FT-IR analysis of the initial MQ resin and the compositions obtained in Examples 1 to 10 are shown in Tables 4 to 6 below.

[0111] The GPC compositions were obtained by deconvolution of the GPC spectra and calibration of free MQ resin (SR) and free alcohol compounds (PA).

[0112] Based on the calculated amount of free alcohol (PA), the remaining alcohol is assumed to react (be capped) onto the MQ resin (SR), and the MQ-OR is estimated assuming molar capping onto the MQ resin. Regarding the FTIR results, if we assume that the Si-OH reduction is due to alcohol capping, the MQ-OR is overestimated compared to GPC. Based on this assumption, the SiOH ppm from the spectra is normalized to the initial MQ resin SiOH signal in each case to estimate the decrease in the SiOH signal due to the reaction with the alcohol compound.

[0113] [Table 4]

[0114] [Table 5]

[0115] [Table 6]

[0116] Referring to Tables 4-6 above, all compositions have >10-70 wt% MQ resin (SR) that is solubilized or partially grafted (capped) with an alcohol / capping agent (PA) to provide a liquid silicone resin composition.

[0117] Examples 11 to 13 Three compositions were prepared according to the procedures of Examples 1-10 above using Silicone Resin 2 and various alcohols / capping agents (PAs) to prepare Examples 11-13, the details of which, along with the Brookfield viscosities of the resulting compositions, are listed in Table 7 below.

[0118] [Table 7]

[0119] The composition 29 The capping percentage was analyzed by Si NMR and the results are shown in Table 8 below. In the table, "I" indicates the initial sample and "F" indicates the final composition prepared. In Table 8, M indicates M siloxy units, D indicates D siloxy units, T indicates T siloxy units, Q indicates Q siloxy units, and Z is independently H or alkyl. OZ indicates an SiOZ group in place of a siloxane bond.

[0120] [Table 8]

[0121] The compositions of Examples 11-13 were also analyzed by GPC against polystyrene standards, and the results are shown in Table 9 below, where "I" indicates the initial sample and "F" indicates the final composition prepared.

[0122] [Table 9]

[0123] Examples 14 to 18 Five compositions were prepared according to the procedures of Examples 1-10 above using various MQ resins (SR) and capping agents (PA) to prepare Examples 14-18, the details of which, along with the viscosities of the resulting compositions, are set forth in Table 10 below.

[0124] [Table 10]

[0125] Example 19 291.7 g of silicone resin 2 and 140 g of polyether alcohol 9 were placed in a 2000 mL four-neck flask. No condensation catalyst was added. The flask was rotary evaporated at 60 °C under a vacuum of 2-5 mmHg to remove 81.68 g of xylene. The resulting product was clear and had a Brookfield viscosity of 1230 cps. The sample was analyzed by GPC, Si NMR, and FT-IR. The resulting product had a resin content of approximately 60%.

[0126] Example 20 100 g of the product formed in Example 19 was cold blended with 6 g of an aminosilicon compound at room temperature for 3 hours at 60 revolutions per minute (rpm) to provide a loading of 10% aminosilicon compound based on the resin content of the product formed in Example 19.

[0127] Example 21 100 g of the product formed in Example 19 and 6 g of an amino silicon compound were blended for 3 hours at 60 rpm and heated at 80° C. in a rotary evaporator at 300 mm Hg vacuum.

[0128] Example 22 100 g of the product formed in Example 19 and 12 g of an amino silicon compound were blended for 3 hours at 60 rpm and heated at 80° C. in a rotary evaporator at 300 mm Hg vacuum.

[0129] The results of GPC and FT-IR analysis for the product compositions obtained in Examples 19-22 are shown in Table 11 below.

[0130] [Table 11]

[0131] The products of Examples 19 to 22 29 The siloxy unit content was analyzed by Si NMR, and the results are shown in Table 12 below. In Table 12, Z is H or alkyl; Me is methyl; neopentyl is (CH3)3CCH2; ASC represents an amino silicon compound; X is independently H, a hydrocarbyl group R having 1 to 30 carbon atoms, or a polyether moiety formed by polyether alcohol 9; and T' is H2NCH2CH2CH2SiO 3 / 2 The siloxy units are shown. The values ​​in Table 12 are mole fractions.

[0132] [Table 12]

[0133] The invention has been described in an illustrative manner, and it is to be understood that the terminology used is intended to be in the nature of words of description rather than of limitation. Obviously, many modifications and variations of the invention are possible in light of the above teachings. The invention may be practiced otherwise than as specifically described. The present specification includes the following aspects. Section 1: 1. A liquid silicone resin composition comprising: (A) a polysiloxane having the formula: (R 1 3SiO 1 / 2 )a (R 2 2SiO 2 / 2 ) b (R’R 2 SiO 2 / 2 ) b’ (R 2 SiO 3 / 2 ) c (R’SiO 3 / 2 ) c’ (SiO 4 / 2 ) d (The subscripts a, b, b’, c, c’, and d are molar fractions such that a + b + b’ + c + c’ + d = 1, provided that 0 < a < 1, 0 ≤ b < 0.2, 0 ≤ b’ ≤ 0.1, 0 < c < 0.2, 0 ≤ c’ ≤ 0.1, 0 < d < 1, and 0 ≤ b’ + c’ ≤ 0.1, and the ratio of subscript a to subscript d is 0.5 to 1.5 (a:d). Each R 1 is independently selected from a hydrocarbyl group having 1 to 30 carbon atoms, -OH, and H. Each R 2 is independently selected from R 1 and -OX, where each X is independently H, a hydrocarbyl group R having 1 to 30 carbon atoms, or a polyether moiety having the general formula -Y-R 3 (-[Y] j -Z) i , where R 3 is a substituted or unsubstituted hydrocarbon segment, each Y is an independently selected oxyalkylene segment of the general formula (C n H 2n O) m , in which the subscript m is 1 to 50, the subscript n is independently selected from 2 to 4 in each part represented by the subscript m, each Z is independently H or a resinous silicone moiety, the subscript i is 0 to 8, and the subscript j is independently 0 or 1 in each part represented by the subscript i. Each R’ is independently selected and contains an amino group, a polysiloxane, and (B) A polyether alcohol compound having the general formula HO-Y-R 3 (-[Y] j -H] i , where each Y, R3 , subscript i, and subscript j are as defined above; and 1. A liquid silicone resin composition comprising: Section 2: (i) the ratio of M siloxy units, designated by the subscript a, to Q siloxy units, designated by the subscript d, is 0.7 to 1.2 a:d; (ii) the subscript a is 0.3 to 0.6; (iii) the sum of subscripts b and c is less than 0.2; (iv) The subscript d is 0.4 to 0.7; (v) the polysiloxane (A) has a weight average molecular weight (Mw) of 2000 to 30,000; or (vi) Any combination of (i) to (v), Item 1. The liquid silicone resin composition according to item 1. Section 3: In the polysiloxane (A), (i) Each R 2 is independently of the formula -OX in said T siloxy units designated by subscript c; (ii) X is each R of the formula -OX 2 The polyether moiety is 1 to 90 mol % of (iii) Each R 1 are independently selected from alkyl and aryl groups containing 1 to 30 carbon atoms and H; or (iv) Any combination of (i) to (iii), Item 3. The liquid silicone resin composition according to item 1 or 2. Section 4: In the polysiloxane (A), (i) Each R 2 are independently 1 and hydrocarbyloxy groups of formula -OR, (ii) Each R 1 are independently selected from alkyl and aryl groups containing 1 to 30 carbon atoms, —OH, and H; (iii) each R is independently selected from alkyl and aryl groups containing 1 to 30 carbon atoms; (iv) each R' independently represents a group of the formula -(CH2) g N(H) f R 2-f wherein each g is independently 1 to 30, f is 0, 1, or 2, and R is independently selected and defined above; or (v) Any combination of (i) to (iv), Item 3. The liquid silicone resin composition according to item 1 or 2. Section 5: The hydrocarbon segment R 3 but, (i) a linear or branched hydrocarbon group having 3 to 30 carbon atoms; (ii) an aromatic group; and (iii) an ether group; and (iv) an amine group, or (v) Any combination of (i) to (iv) is included. Item 5. The liquid silicone resin composition according to any one of items 1 to 4. Item 6: (i) the hydrocarbon segment R 3 contains a branched chain hydrocarbon group having 3 to 16 carbon atoms; (ii) the subscript i is 1 to 8; (iii) the subscript j is 1 in each part indicated by the subscript i; (iv) each oxyalkylene segment Y independently has the formula (C2H4O) x (C3H6O) y (C4H8O) z wherein the subscript x is 1 to 50, the subscript y is 0 to 50, and the subscript z is 0 to 50, and the units represented by the subscripts x, y, and z may be randomized or in block form in the oxyalkylene segment; or (v) Any combination of (i) to (iv), Item 6. The liquid silicone resin composition according to any one of Items 1 to 5. Section 7: (i) Each subscript i is 0, and each hydrocarbon segment R 3each independently comprises a straight or branched chain hydrocarbon group having 3 to 30 carbon atoms; (ii) each subscript i is 1 and each hydrocarbon segment R 3 independently comprise at least one group selected from a linear or branched hydrocarbon group having 3 to 30 carbon atoms, a phenol, a tetrahydrofuran, an alkylamine, and an alkoxy group; or (iii) each subscript i is at least 2, and each hydrocarbon segment R 3 each independently comprises at least one group selected from a linear or branched hydrocarbon group having 3 to 30 carbon atoms, an alkylamine, a polyamine, a polyamide, a polyaziridine, a polyphenol, and a polyester; Item 6. The liquid silicone resin composition according to any one of Items 1 to 5. Section 8: Item 8. The liquid silicone resin composition according to any one of Items 1 to 7, wherein the polyether alcohol compound (B) comprises an alkoxylation reaction product of (b-1) an organic compound containing an alkoxylatable group having an O-, N-, or S-bonded hydrogen atom and (b-2) an alkylene oxide or a polyoxyalkylene compound. Section 9: (i) the organic compound (b-1) is further defined as an alcohol compound containing 1 to 9 hydroxyl groups; (ii) the alkylene oxide or polyoxyalkylene compound (b-2) is selected from ethylene oxide, propylene oxide, butylene oxide, a combination thereof, or a polyoxyalkylene formed therefrom; or (iii) Both (i) and (ii); Item 9. The liquid silicone resin composition according to item 8. Section 10: The polyether alcohol compound (B) (i) a polydispersity index (PDI) of less than 1.15; (ii) a molecular weight (Mw) of less than 5000; (iii) less than 2% by weight of unreacted alcohol compound (b-1) based on the total weight of the polyether alcohol compound (B); or (iv) Any combination of (i) to (iii) is included. Item 10. The liquid silicone resin composition according to item 8 or 9. Section 11: (i) 10% by weight to 80% by weight of the polysiloxane (A) based on the total weight of the composition; (ii) 10% by weight to 95% by weight of the polyether alcohol compound (B) based on the total weight of the composition; (iii) a viscosity of 100 to 800,000 cps at 25°C; or (iv) Any combination of (i) to (iii) is included. Item 11. The liquid silicone resin composition according to any one of items 1 to 10. Section 12: The composition comprises: (i) does not contain tin; (ii) does not contain cyclic siloxanes; (iii) containing less than 1% by weight of solvent based on the total weight of the composition; or (iv) Any combination of (i) to (iii), Item 12. The liquid silicone resin composition according to any one of items 1 to 11. Section 13: The method comprises: combining together a solid silicone resin and the polyether alcohol compound (B) to obtain a mixture comprising the polysiloxane (A) and the polyether alcohol compound (B), wherein the solid silicone resin has the formula: (R 1 3SiO 1 / 2 ) a (R 4 2SiO 2 / 2 ) b (R 4 SiO 3 / 2 ) c (SiO 4 / 2 ) d During the ceremony, Each R 4 is R 1 and -OR, with the proviso that R 4is selected from —OH and —OR in at least one T siloxy unit designated by subscript c; Each R 1 , R and the subscripts a, b, c, and d are as defined above; and liquefying the mixture to prepare the liquid silicone resin composition; Item 13. A method for preparing the liquid silicone resin composition according to any one of items 1 to 12, comprising: Section 14: Item 14. The method according to item 13, further comprising: subjecting the solid silicone resin and the polyether alcohol compound (B) to a condensation reaction to prepare the polysiloxane (A) in the mixture. Section 15: Item 15. The method of claim 13 or 14, wherein the method further comprises combining an aminosilicon compound (C) with the solid silicone resin and the polyether alcohol compound (B), and / or the method further comprises combining an aminosilicon compound (C) with the mixture before and / or after liquefying the mixture. Section 16: The amino silicon compound (C) is represented by the formula R'R 10 h Si(OR 10 ) 3-h wherein R' comprises an amino group and each R 10 Item 16. The method according to Item 15, wherein: is an independently selected alkyl group having 1 to 18 carbon atoms, and the subscript h is 0 or 1. Section 17: the solid silicone resin and the polyether alcohol compound (B) are combined together in the presence of a solvent, the method further comprising dissolving the solid silicone resin in the solvent to obtain a silicone resin solution; Combining the solid silicone resin and the polyether alcohol compound (B) to form the mixture is further defined as mixing the silicone resin solution with the polyether alcohol compound (B). Item 17. The method according to any one of Items 13 to 16. Section 18: liquefying the mixture includes solvent exchanging the solid silicone resin from the solvent into the polyether alcohol compound (B); The solvent exchange is carried out (i) at a temperature of 60 to 150°C, (ii) under reduced pressure, (iii) by removing the solvent under distillation conditions, or (iv) any combination of (i) to (iii). Item 18. The method according to item 17. Section 19: The solvent is (i) xylene; (ii) hexamethylenedisiloxane; and (iii) octamethylcyclotetrasiloxane (D4), (iv) decamethylcyclopentasiloxane (D5), or (v) Any combination of (i) to (iv) is included. Item 17. The method according to item 17 or 18. Section 20: The liquid silicone resin composition (i) does not contain tin; (ii) does not contain cyclic siloxanes; (iii) containing less than 1% by weight of solvent based on the total weight of the composition; or (iv) Any combination of (i) to (iii), 20. The method according to any one of items 13 to 19.

Claims

1. 1. A liquid silicone resin composition comprising: (A) a polysiloxane having the formula: (R １ ３ SiO １／２ ) ａ (R ２ ２ SiO ２／２ ) ｂ (R’R ２ SiO ２／２ ) ｂ’ (R ２ SiO ３／２ ) ｃ (R’SiO ３／２ ) ｃ’ (SiO ４／２ ) ｄ 、 The subscripts a, b, b', c, c', and d are mole fractions such that a+b+b'+c+c'+d=1, where 0<a<1, 0≦b<0.2, 0≦b'≦0.1, 0<c<0.2, 0≦c'≦0.1, 0<d<1, and 0≦b'+c'≦0.1, and the ratio of the subscript a to the subscript d is 0.5 to 1.5 (a:d), and each R １ is independently selected from a hydrocarbyl group having 1 to 30 carbon atoms, —OH, and H; and each R ２ is R １ and —OX, where each X is independently H, a hydrocarbyl group R having 1 to 30 carbon atoms, or a group of the general formula —Y—R ３ (-[Y] ｊ -Z) ｉ where R ３ is a substituted or unsubstituted hydrocarbon segment, and each Y is a group represented by the general formula (C ｎ H ２ｎ O) ｍ wherein the subscript m is 1 to 50, the subscript n is independently selected from 2 to 4 in each moiety designated by the subscript m, each Z is independently H or a resinous silicone moiety, the subscript i is 0 to 8, the subscript j is independently 0 or 1 in each moiety designated by the subscript i, and each R′ comprises an independently selected amino group; (B) General formula HO-Y-R ３ (-[Y] ｊ -H] ｉ wherein each Y, R ３ , subscript i, and subscript j are as defined above; and a polyether alcohol compound.

2. 10. The liquid silicone resin composition of claim 1, wherein: (i) the ratio of M siloxy units, designated by subscript a, to Q siloxy units, designated by subscript d, is from 0.7 to 1.2a:d; (ii) subscript a is from 0.3 to 0.6; (iii) the sum of subscripts b and c is less than 0.2; (iv) subscript d is from 0.4 to 0.7; (v) said polysiloxane (A) comprises a weight average molecular weight (Mw) of from 2000 to 30,000; or (vi) any combination of (i)-(v).

3. In the polysiloxane (A), (i) each R ２ is independently of the formula -OX in said T siloxy units denoted by subscript c, and (ii) X is a group of each R of formula -OX ２ (iii) each R １ is independently selected from alkyl and aryl groups containing from 1 to 30 carbon atoms and H, or (iv) any combination of (i) through (iii).

4. In the polysiloxane (A), (i) each R ２ are independently R １ and a hydrocarbyloxy group of formula —OR; (ii) each R １ are independently selected from alkyl and aryl groups containing 1 to 30 carbon atoms, —OH, and H; (iii) each R is independently selected from alkyl and aryl groups containing 1 to 30 carbon atoms; and (iv) each R′ is independently a group of the formula —(CH ２ ) ｇ N (H) ｆ R ２－ｆ wherein each g is independently 1 to 30, f is 0, 1, or 2, and R is independently selected and defined above, or any combination of (v)(i) through (iv).

5. (i) the hydrocarbon segment R ３ comprises a branched chain hydrocarbon group having 3 to 16 carbon atoms; (ii) subscript i is 1 to 8; (iii) subscript j is 1 in each portion designated by subscript i; and (iv) each oxyalkylene segment Y independently has the formula (C ２ H ４ O) ｘ (C ３ H ６ O) ｙ (C ４ H ８ O) ｚ wherein the subscript x is 1 to 50, the subscript y is 0 to 50, and the subscript z is 0 to 50; and the units represented by the subscripts x, y, and z can be randomized or in block form in said oxyalkylene segments, or any combination of (v)(i) to (iv).

6. (i) each subscript i is 0, and each hydrocarbon segment R ３ independently comprise a straight or branched chain hydrocarbon group having from 3 to 30 carbon atoms, (ii) each subscript i is 1, and each hydrocarbon segment R ３ independently comprise at least one group selected from linear or branched hydrocarbon groups having 3 to 30 carbon atoms, phenols, tetrahydrofurans, alkylamines, and alkoxy groups, or (iii) each subscript i is at least 2, and each hydrocarbon segment R ３ and independently comprise at least one group selected from a linear or branched hydrocarbon group having from 3 to 30 carbon atoms, an alkylamine, a polyamine, a polyamide, a polyaziridine, a polyphenol, and a polyester.

7. combining together a solid silicone resin and the polyether alcohol compound (B) to obtain a mixture comprising the polysiloxane (A) and the polyether alcohol compound (B), wherein the solid silicone resin has the formula: (R １ ３ SiO １／２ ) ａ (R ４ ２ SiO ２／２ ) ｂ (R ４ SiO ３／２ ) ｃ (SiO ４／２ ) ｄ 、 In the formula, each R ４ is R １ and -OR, with the proviso that R ４ is selected from —OH and —OR in at least one T siloxy unit designated by subscript c, and each R １ , R and the subscripts a, b, c, and d are as defined above; and 3. A method for preparing the liquid silicone resin composition of claim 1 or 2, comprising: liquefying said mixture to prepare said liquid silicone resin composition.

8. 8. The method of claim 7, further comprising: subjecting the solid silicone resin and the polyether alcohol compound (B) to a condensation reaction to prepare the polysiloxane (A) in the mixture.

9. 10. The method of claim 7, wherein the method further comprises combining (C) an aminosilicon compound with the solid silicone resin and the polyether alcohol compound (B), and / or the method further comprises combining (C) an aminosilicon compound with the mixture before and / or after liquefying the mixture.

10. 8. The method of claim 7, wherein the liquid silicone resin composition (i) is tin-free, (ii) is cyclic siloxane-free, (iii) contains less than 1 wt. % solvent, based on the total weight of the composition, or (iv) any combination of (i)-(iii).

Images