Composition for preparing anti-sticking coating

Abstract

The present disclosure provides a composition for forming a release coating, the composition comprising (A) an organopolysiloxane comprising at least one RSiO3 / 2 siloxy unit or at least one SiO4 / 2 siloxy unit, where R is a substituted or unsubstituted hydrocarbyl group. The (A) organopolysiloxane has an average of at least two silicon-bonded ethylenically unsaturated groups per molecule. The composition further comprises (B) an organosilicon compound having an average of at least two silicon-bonded hydrogen atoms per molecule. Finally, the composition comprises (C) a hydrosilylation catalyst comprising a metal-ligand complex having the formula MLxDy, where M is a metal; x is equal to the oxidation state of M; each D is independently a neutral coordination ligand; y is 0 or an integer from 1 to 4; and each L is a monoanionic ligand having a specific formula.

Description

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims priority to and all advantages of U.S. Provisional Patent Application No. 63 / 357,173 filed on June 30, 2022, the contents of which are incorporated herein by reference. Technical Field

[0003] The present disclosure relates generally to a composition, and more particularly to compositions for preparing release coatings and related methods. Background Art

[0004] Silicone compositions are known in the art and are used in numerous industries and end-use applications. One such end-use application is to form a release coating or liner from which an adhesive can be removed. For example, silicone compositions can be used to coat various substrates, such as paper, to obtain a release liner for laminating a pressure-sensitive adhesive (e.g., tape). Such silicone compositions are typically addition curable.

[0005] Conventional release liners are usually formed by reacting an organopolysiloxane having an unsaturated hydrocarbon group with an organohydrogenpolysiloxane in the presence of a hydrosilylation catalyst (or hydrosilylation). It is usually desirable to extend the soaking life of the composition used to prepare the release liner to extend the working life and minimize premature curing. Therefore, inhibitors are usually included in the conventional composition used to prepare the release liner. However, inhibitors and hydrosilylation catalysts also have compatibility issues, which affect the soaking life and the performance characteristics of the resulting release coating. Summary of the invention

[0006] A composition for forming a non-stick coating is disclosed. The composition comprises (A) an organopolysiloxane comprising at least one RSiO 3 / 2 Siloxy unit or at least one SiO 4 / 2 siloxy units, wherein R is a substituted or unsubstituted hydrocarbon group. The (A) organopolysiloxane has an average of at least two silicon-bonded ethylenically unsaturated groups per molecule. The composition also includes (B) an organosilicon compound, which has an average of at least two silicon-bonded hydrogen atoms per molecule. Finally, the composition includes (C) a hydrosilylation catalyst, which includes a hydrosilylation catalyst having a formula ML x D y A metal-ligand complex wherein M is a metal; x is equal to the oxidation state of M; each D is independently a neutral coordinating ligand; y is 0 or an integer from 1 to 4; and each L is independently a monoanionic ligand having the formula:

[0007]

[0008] Each R 1 and R 2 is independently a halide or selected from C1-C6 alkyl, C3-C8 cycloalkyl, C3-C8 heterocycloalkyl, C6-C 10 Alkyl aryl, C1-C6 alkoxy, C6-C 10 Aryl, C6-C 10 Heteroaryl, silyl, C2-C8 alkenyl, C2-C8 alkynyl, C1-C6 hydroxyl, C3-C 10 Arylene, C3-C 10 Heteroarylene, C2-C 10 Alkenylene, C3-C 10 Cycloalkenylene and C2-C 10 A substituted or unsubstituted alkynylene group, wherein R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 Each of the following is independently selected from hydrogen, halide or C1-C6 alkyl, C3-C8 cycloalkyl, C3-C8 heterocycloalkyl, C6-C 10 Alkyl aryl, C1-C6 alkoxy, C6-C 10 Aryl, C6-C 10 Heteroaryl, silyl, C2-C8 alkenyl, C2-C 10 Alkynyl, C1-C6 hydroxyl, C3-C 10 Arylene, C3-C 10 Heteroarylene, C2-C 10 Alkenylene, C3-C 10 Cycloalkenylene and C2-C 10 A substituted or unsubstituted group of alkynylene; and wherein E is C or Si.

[0009] A method of preparing the composition is also disclosed. In addition, a method of preparing a coated substrate comprising a release coating disposed on a substrate, and a coated substrate formed according to the method are disclosed. DETAILED DESCRIPTION

[0010] A composition for forming a release coating is disclosed. The composition has excellent stability at room temperature, thereby providing an extended soak life for release coating applications.

[0011] The composition comprises (A) an organopolysiloxane, wherein the organopolysiloxane comprises at least one RSiO 3 / 2 Siloxy unit or at least one SiO 4 / 2Siloxy units, wherein R is a substituted or unsubstituted hydrocarbon group. As is known in the art, RSiO 3 / 2 The siloxy units are T siloxy units, and SiO 4 / 2 The siloxy units are Q siloxy units. T and / or Q siloxy units are present in branched and resinous organopolysiloxanes. Therefore, in one embodiment, the (A) organopolysiloxane is branched. In another embodiment, the (A) organopolysiloxane is resinous. A combination of different organopolysiloxanes may be used as the (A) organopolysiloxane, and even a linear organopolysiloxane having at least one RSiO may be used in combination with a branched organopolysiloxane having at least one RSiO 3 / 2 Siloxy unit or at least one SiO 4 / 2 The (A) organopolysiloxane may be used together with those containing siloxy units. The (A) organopolysiloxane has an average of at least two silicon-bonded ethylenically unsaturated groups per molecule. The silicon-bonded ethylenically unsaturated groups in the (A) organopolysiloxane may be terminal and / or pendant. In certain embodiments, the (A) organopolysiloxane has an average of at least two silicon-bonded groups having terminal aliphatic unsaturation per molecule.

[0012] Typically, the hydrocarbon group suitable for R can be independently straight chain, branched, cyclic or a combination thereof. Cyclic hydrocarbon groups include aryl groups and saturated or non-conjugated cyclic groups. Cyclic hydrocarbon groups can be independently monocyclic or polycyclic. Straight chain and branched hydrocarbon groups can be independently saturated or unsaturated. An example of a combination of straight chain and cyclic hydrocarbon groups is an aralkyl group. General examples of hydrocarbon groups include alkyl groups, aryl groups, alkenyl groups, halogenated carbon groups, etc., and their derivatives, modifications and combinations. Examples of suitable 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, hexadecyl, octadecyl, and a branched saturated hydrocarbon group with 6 to 18 carbon atoms. The example of suitable non-conjugated cyclic group comprises cyclobutyl, cyclohexyl and cycloheptyl group.The example of suitable aryl group comprises phenyl, tolyl, xylyl, naphthyl, benzyl and dimethylphenyl.The example of suitable alkenyl group comprises vinyl, allyl, propenyl, isopropenyl, butenyl, isobutenyl, pentenyl, heptenyl, hexenyl, octenyl, hexadecene, octadecene and cyclohexenyl group.The example of suitable monovalent halogenated hydrocarbon group (that is, hydrocarbon group) comprises halogenated alkyl group, aryl group and their combination.The example of halogenated alkyl group comprises the above-mentioned alkyl group that wherein one or more hydrogen atoms are replaced by halogen atoms such as F or Cl. The specific example of haloalkyl group includes 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 groups, and their derivatives. The example of halogenated aryl group includes the above-mentioned aryl group in which one or more hydrogen atoms are replaced by halogen atoms such as F or Cl. The specific example of halogenated aryl group includes chlorobenzyl and fluorobenzyl groups.

[0013] In a specific embodiment, each R is independently selected from an alkyl group having 1 to 32, alternatively 1 to 28, alternatively 1 to 24, alternatively 1 to 20, alternatively 1 to 16, alternatively 1 to 12, alternatively 1 to 8, alternatively 1 to 4, alternatively 1 carbon atoms, and an ethylenically unsaturated (i.e., alkenyl and / or alkynyl group) group having 2 to 32, alternatively 2 to 28, alternatively 2 to 24, alternatively 2 to 20, alternatively 2 to 16, alternatively 2 to 12, alternatively 2 to 8, alternatively 2 to 4, alternatively 2 carbon atoms. "Alkenyl" means an acyclic, branched or unbranched monovalent hydrocarbon group having one or more carbon-carbon double bonds. Specific examples thereof include vinyl group, allyl group, hexenyl group and octenyl group. "Alkynyl" means an acyclic, branched or unbranched monovalent hydrocarbon group having one or more carbon-carbon triple bonds. Specific examples thereof include ethynyl, propynyl and butynyl groups. Various examples of ethylenically unsaturated groups include CH2=CH—, CH2=CHCH2—, CH2=CH(CH2)4—, CH2=CH(CH2)6—, CH2=C(CH3)CH2—, H2C=C(CH3)—, H2C=C(CH3)—, H2C=C(CH3)CH2—, H2C=CHCH2CH2—, H2C=CHCH2CH2CH2—, HC≡C—, HC≡CCH2—, HC≡CCH(CH3)—, HC≡CC(CH3)2— and HC≡CC(CH3)2CH2—. Generally, when R is an ethylenically unsaturated group, the aliphatic unsaturation is at the end of R. As understood in the art, ethylenic unsaturation can be referred to as aliphatic unsaturation.

[0014] (A) The polyorganosiloxane may have the average formula: R m SiO (4-m) / 2 , where each R is independently selected and as defined above, provided that in each molecule, at least two of the Rs include aliphatic unsaturation, and where the subscript m is selected such that 0 < m ≤ 3.2. The average formula of the above (A) organopolysiloxane can alternatively be written as (R3SiO 1 / 2 ) e (R2SiO 2 / 2 ) f (RSiO 3 / 2 ) g (SiO 4 / 2 ) h , where R is as defined above, and the subscripts e, f, g and h are each independently ≥0 to ≤1, provided that the subscripts g and h cannot both be 0, and the quantity (e + f + g + h) = 1. Those skilled in the art understand how these M, D, T and Q units and their mole fractions affect the subscript m in the above average formula.

[0015] In one embodiment, (A) the organopolysiloxane may include a resinous polyorganosiloxane. The resinous polyorganosiloxane may have an average formula: R m' SiO (4-m') / 2 , wherein each R is independently selected as defined above, and wherein the subscript m' is selected such that 0.5≤m'≤1.7.

[0016] Resin-like polyorganosiloxanes have a branched or three-dimensional network molecular structure. At 25° C., the resin-like polyorganosiloxane may be in liquid or solid form. Alternatively, the resin-like polyorganosiloxane may be exemplified by a polyorganosiloxane comprising only T units, a polyorganosiloxane comprising a combination of T units and other siloxy units (e.g., M, D and / or Q siloxy units), or a polyorganosiloxane comprising a combination of Q units and other siloxy units (i.e., M, D and / or T siloxy units). Typically, the resin-like polyorganosiloxane comprises T and / or Q units. Specific examples of resin-like polyorganosiloxanes include vinyl-terminated silsesquioxanes (i.e., T resins or silsesquioxane resins), vinyl-terminated MDQ resins, and / or vinyl-terminated MQ resins.

[0017] Alternatively, the (A) organopolysiloxane may comprise, or alternatively consist of, branched siloxane, silsesquioxane, or both branched siloxane and silsesquioxane.

[0018] When (A) organopolysiloxane comprises a blend of different organopolysiloxanes, the blend may be a physical blend or mixture. For example, when (A) organopolysiloxane comprises branched siloxane and silsesquioxane, based on the combined weight of all components present in the composition, the branched siloxane and silsesquioxane may be present relative to each other in an amount such that the amount of the branched siloxane and the amount of the silsesquioxane are combined to a total of 100 parts by weight. The branched siloxane may be present in an amount of 50 parts by weight to 100 parts by weight, and the silsesquioxane may be present in an amount of 0 parts by weight to 50 parts by weight. Alternatively, the branched siloxane may be present in an amount of 50 parts by weight to 90 parts by weight, and the silsesquioxane may be present in an amount of 10 parts by weight to 50 parts by weight. Alternatively, the branched siloxane may be present in an amount of 50 parts by weight to 80 parts by weight, and the silsesquioxane may be present in an amount of 20 parts by weight to 50 parts by weight. Alternatively, the branched siloxane may be present in an amount of 50 to 76 parts by weight, and the silsesquioxane may be present in an amount of 24 to 50 parts by weight. Alternatively, the branched siloxane may be present in an amount of 50 to 70 parts by weight, and the silsesquioxane may be present in an amount of 30 to 50 parts by weight.

[0019] In certain embodiments, the branched siloxane of the (A) organopolysiloxane may have an average unit formula:

[0020] (R3SiO 1 / 2 ) p (R2SiO 2 / 2 ) q (SiO 4 / 2 ) r ,

[0021] wherein each R is independently selected and defined as above, provided that at least two, alternatively at least three of the Rs include aliphatic unsaturation; 0 < p ≤ 0.3, 0.4 ≤ q ≤ 0.97, and 0 < r ≤ 0.3, provided that p + q + r = 1.

[0022] (A) The branched siloxanes of the organopolysiloxanes generally contain M siloxy units (i.e., (R3SiO 1 / 2 ) siloxy units), D siloxy units (i.e., (R2SiO 2 / 2 ) siloxy units) and one or more Q siloxy units (i.e., (SiO 4 / 2 ) siloxy units), alternatively consisting of M, D and Q siloxy units. Although the branched siloxanes of (A) the organopolysiloxanes include at least one Q siloxy unit, due to the degree of polymerization (DP) in the branched siloxanes of (A) the organopolysiloxanes and the mole fraction of the Q siloxy units present therein, the branched siloxanes of (A) the organopolysiloxanes are regarded by those skilled in the art as branched organosilicon polymers rather than organosilicon resins.

[0023] (A) The general formula of the branched siloxanes of the organopolysiloxanes represents the average formula of the M, D and Q siloxy units. For example, the M siloxy units can be independently selected within the formula (R3SiO 1 / 2 ), and the D siloxy units can be independently selected within the formula (R2SiO 2 / 2 ). The subscripts or mole fractions of the M, D and Q siloxy units in the branched siloxanes of (A) the organopolysiloxanes are collectively based on all the M siloxy units, all the D siloxy units and all the Q siloxy units present in the branched siloxanes of (A) the organopolysiloxanes. For example, the branched siloxanes of (A) the organopolysiloxanes can include M units independently having zero, one, two or three silicon-bonded olefinically saturated groups. Similarly, the branched siloxanes of (A) the organopolysiloxanes can include D units independently having zero, one or two silicon-bonded olefinically unsaturated groups. Such silicon-bonded olefinically unsaturated groups present in the M siloxy units are regarded as end groups, while those present in the D siloxy units are regarded as side groups.

[0024] In specific embodiments, the branched siloxane of the (A) organopolysiloxane has one Q siloxy unit. In other embodiments, the branched siloxane of the (A) organopolysiloxane has two Q siloxy units, alternatively three Q siloxy units. The branched siloxane of the (A) organopolysiloxane may have a degree of polymerization (DP) of 1 to 3000, alternatively 2 to 2000, alternatively 3 to 1000, alternatively 4 to 750, alternatively 5 to 400, alternatively 10 to 200, alternatively 14 to 180. The DP is typically the total number of D units present in the branched siloxane of the (A) organopolysiloxane, i.e., the DP may be based on more than one linear chain within the branched siloxane of the (A) organopolysiloxane.

[0025] In a specific embodiment, when the branched siloxane of the (A) organopolysiloxane includes one Q siloxy unit, the branched siloxane of the (A) organopolysiloxane may have an average unit formula:

[0026] (R3SiO 1 / 2 ) x (R2SiO 2 / 2 ) z (SiO 4 / 2 ),

[0027] wherein each R is independently a substituted or unsubstituted hydrocarbyl group, provided that at least two of the R are independently selected ethylenically unsaturated groups, subscript x is from 0.05 to 4, and subscript z is from 1 to 3,000.

[0028] In specific embodiments, the silicon-bonded ethylenically unsaturated groups are present in one or more M siloxy units (e.g., as vinyldimethylsiloxy units, divinylmethylsiloxy units, and / or trivinylsiloxy units). Alternatively, in other embodiments, the silicon-bonded ethylenically unsaturated groups are present in one or more D siloxy units (e.g., as methylvinylsiloxy groups and / or as divinylsiloxy groups). Still alternatively, the silicon-bonded ethylenically unsaturated groups may be present in one or more units of each of the M and D siloxy units. Those skilled in the art will appreciate that these specific siloxy groups are exemplary only, and that the vinyl groups may be substituted with other ethylenically unsaturated groups, and that the methyl groups may be substituted with other hydrocarbyl groups.

[0029] In a specific embodiment where the branched siloxane of (A) the organopolysiloxane comprises a single Q siloxy unit, the branched siloxane of (A) the organopolysiloxane has the following general formula:

[0030] Si-[[OSiR2] b' [OSiR3]]4

[0031] wherein each R is independently selected and as defined above, with the proviso that at least two of R include aliphatic unsaturation, and each b' is independently from 0 to 200, alternatively from 1 to 100.

[0032] However, because the branched siloxane of the (A) organopolysiloxane includes D siloxy units, all instances of b' (i.e., all four instances) cannot be 0 at the same time. In these embodiments, the DP of the branched siloxane of the (A) organopolysiloxane is based on the total or aggregate amount of b'. The branched siloxane of the (A) organopolysiloxane includes at least one, alternatively at least two, alternatively at least three, alternatively four substantially linear, alternatively linear chains extending from the silicon atom of the Q unit. When any iteration of b' is greater than 0, these substantially linear or linear chains correspond to repeating D siloxy units.

[0033] In these specific embodiments, the branched siloxane of (A) the organopolysiloxane includes a single Q siloxy unit and does not include a T siloxy unit. As is understood in the art, the T siloxy unit may be composed of RSiO 3 / 2 denoted by , and includes one silicon-bonded substituent R. The branched siloxane of the (A) organopolysiloxane includes D siloxy units corresponding to each iteration of the subscript b'. Because b' is independently selected, each linear chain of the D siloxy units indicated by the subscript b' can vary, i.e., each b' can be the same as or different from each other. One or more instances of b' can be 0, such that the M siloxy unit is directly bonded to a single Q siloxy unit, but typically each M siloxy unit is separated from the Q siloxy unit by at least one D siloxy unit. The branched siloxane of the (A) organopolysiloxane can also be typically symmetrical, i.e., when all instances of b' are the same. Each of the linear chains of the D siloxy units in the branched siloxane of the (A) organopolysiloxane is terminated with an M siloxy unit.

[0034] In a specific embodiment, the branched siloxane of (A) the organopolysiloxane has the general formula:

[0035] Si-[[OSiMe2] b' [OSiMe2Vi]]4

[0036] wherein b' is independently selected and as defined above, Me represents a methyl group, and Vi represents a vinyl group. In other specific embodiments, the branched siloxane of (A) the organopolysiloxane has the general formula:

[0037] Si-[[OSiViMe] b' [OSiMe3]]4

[0038] wherein b' is independently selected and as defined above.

[0039] In other specific embodiments, the branched siloxane of (A) the organopolysiloxane has the following general formula:

[0040] Si-[[OSiViMe] b' [OSiMe2Vi]]4

[0041] wherein b' is independently selected and as defined above.

[0042] In addition, each D and M siloxy unit in the branched siloxane of (A) organopolysiloxane is independently selected. In this way, any of the above specific examples can be modified. For example, in one embodiment, the branched siloxane of (A) organopolysiloxane can include three dimethylvinylsiloxy units and one trimethylsiloxy unit.

[0043] Alternatively, the (A) organopolysiloxane may have the formula:

[0044] wherein subscript u is 0 or 1, each subscript t is independently 0 to 995, alternatively 15 to 995, alternatively 0 to 100; and each R is independently selected and as defined above, with the proviso that at least two of R are independently selected ethylenically unsaturated groups.

[0045] The (A) organopolysiloxane may be a silsesquioxane having the following average unit formula: 10 3SiO 1 / 2 ) i (R 11 R 10 2SiO 1 / 2 ) f (R 10 2SiO 2 / 2 ) g (R 10 SiO 3 / 2 ) h , where each R 10 is an independently selected hydrocarbon group free of aliphatic unsaturation, each R 11 is an independently selected ethylenically unsaturated group, subscript i ≥ 0, subscript f > 0, subscript g is 15 to 995, and subscript h > 0. Subscript i may be 0 to 10. Alternatively, for subscript i: 12 ≥ i ≥ 0; alternatively 10 ≥ i ≥ 0; alternatively 7 ≥ i ≥ 0; alternatively 5 ≥ i ≥ 0; and alternatively 3 ≥ i ≥ 0.

[0046] Alternatively, subscript f≥1. Alternatively, subscript f≥3. Alternatively, for subscript f: 12≥f>0; alternatively 12≥f≥3; alternatively 10≥f>0; alternatively 7≥f>1; alternatively 5≥f≥2; and alternatively 7≥f≥3. Alternatively, for subscript g: 800≥g≥15; and alternatively 400≥g≥15. Alternatively, subscript h≥1. Alternatively, subscript h is 1 to 10. Alternatively, for subscript h: 10≥h>0; alternatively 5≥h>0; and alternatively h=1. Alternatively, subscript h is 1 to 10, alternatively subscript h is 1 or 2. Alternatively, when subscript h=1, then subscript f may be 3 and subscript i may be 0.

[0047] (A) The organopolysiloxane may have the formula (R3SiO 1 / 2 ) x' (R2SiO 2 / 2 ) z' (SiO 4 / 2 ) 1.0 (ZO 1 / 2 ) w , wherein each R is independently selected and as defined above, provided that in each molecule, at least two of the R are independently selected ethylenically unsaturated groups, subscript x' is 1.5 to 4; Z is independently selected from H and alkyl groups having 1 to 4 carbon atoms; subscript w is 0 to 3; subscript z' is 3 to 1,000. When (A) the organopolysiloxane is prepared via hydrolysis and condensation of silanes, there is generally an inherent presence of (ZO 1 / 2 ) is not present in the organopolysiloxane. 1 / 2 ) represents a portion, which depends on its preparation method.

[0048] Regardless of how the branched siloxane of (A) organopolysiloxane is selected, the branched siloxane of (A) organopolysiloxane has at least two, alternatively at least three silicon-bonded ethylenically unsaturated groups. In certain embodiments, based on the total weight of the branched siloxane of (A) organopolysiloxane, the branched siloxane of (A) organopolysiloxane has an ethylenically unsaturated group content of 2.0 wt % to 7.0 wt %, alternatively 2.0 wt % to 6.0 wt %, alternatively 2.0 wt % to 5.5 wt %. This is usually the case when each R group is methyl or vinyl. However, as understood in the art, when R is a substance other than methyl (e.g., ethyl, aryl) and / or when R is a substance other than vinyl (e.g., allyl, hexenyl), the total weight % occupied by the same number of R groups may be smaller, which will affect the molecular weight of the branched siloxane of (A) organopolysiloxane. The content of R can be measured using silicon 29 nuclear magnetic resonance spectroscopy ( 29In certain embodiments, the branched siloxane of the (A) organopolysiloxane has a viscosity at 25° C. of greater than 0 mPa·s to less than 400 mPa·s, alternatively greater than 0 mPa·s to less than 300 mPa·s, alternatively greater than 0 mPa·s to less than 200 mPa·s.

[0049] The (A) organopolysiloxane may include a combination of two or more different polyorganosiloxanes that differ in at least one characteristic such as structure, molecular weight, content of monovalent groups bonded to silicon atoms, and aliphatic unsaturated groups.

[0050] For example, as described above, the (A) organopolysiloxane includes at least one T siloxy unit and / or at least one Q siloxy unit. However, the (A) organopolysiloxane may also include another organopolysiloxane, which may be substantially linear, alternatively linear. The substantially linear organopolysiloxane may have an average formula: R a' SiO (4-a') / 2 , wherein each R is as defined above, and wherein the subscript a' is selected such that 1.9 ≤ a' ≤ 2.2.

[0051] At 25° C., the substantially linear organopolysiloxane of component (A) may be a flowable liquid or may have the form of an uncured rubber. The substantially linear organopolysiloxane may have a viscosity of 10 mPa·s to 30,000,000 mPa·s, alternatively 10 mPa·s to 10,000 mPa·s, alternatively 100 mPa·s to 1,000,000 mPa·s, and alternatively 100 mPa·s to 100,000 mPa·s at 25° C. The viscosity may be measured at 25° C. by a Brookfield LV DV-E viscometer having a spindle selected to be suitable for the viscosity of the substantially linear polyorganosiloxane, i.e., RV-1 to RV-7.

[0052] Alternatively, when the (A) organopolysiloxane further comprises another organopolysiloxane that is substantially linear, the substantially linear organopolysiloxane may have an average unit formula:

[0053] (R 11 R 10 2SiO 1 / 2 ) aa (R 11 R 10 SiO 2 / 2 ) bb (R 11 2SiO 2 / 2 ) cc (R 10 3SiO 1 / 2 )dd ,

[0054] Each R 10 is an independently selected hydrocarbon group free of aliphatic unsaturation; each R 11 is an independently selected ethylenically unsaturated group; subscript aa is 0, 1 or 2, subscript bb is 0 or greater, subscript cc is 1 or greater, subscript dd is 0, 1 or 2, provided that the amount (aa+dd) is ≥2, and (aa+dd)=2, provided that the amount (aa+bb+cc+dd) is 3 to 2,000. Alternatively, subscript cc is ≥0. Alternatively, subscript bb is ≥2. Alternatively, the amount (aa+dd) is 2 to 10, alternatively 2 to 8, and alternatively 2 to 6. Alternatively, subscript cc is 0 to 1,000, alternatively 1 to 500, and alternatively 1 to 200. Alternatively, subscript bb is 2 to 500, alternatively 2 to 200, and alternatively 2 to 100.

[0055] For R 10 The hydrocarbyl groups free of aliphatic unsaturation are exemplified by alkyl groups having 1 to 6 carbon atoms, aryl groups having 6 to 10 carbon atoms, haloalkyl groups having 1 to 6 carbon atoms, haloaryl groups having 6 to 10 carbon atoms, aralkyl groups having 7 to 12 carbon atoms, or haloaralkyl groups having 7 to 12 carbon atoms, wherein alkyl, aryl, and haloalkyl are as described herein. Alternatively, each R 10 is an alkyl group. Alternatively, each R 10 R is independently methyl, ethyl or propyl. 10 Each case of may be the same or different. Alternatively, each R 10 A methyl group.

[0056] For R 11 The aliphatic unsaturated monovalent hydrocarbon group is capable of reacting in a hydrosilylation reaction. 11 Suitable aliphatic unsaturated hydrocarbon groups of are exemplified by alkenyl groups as defined herein and exemplified by vinyl, allyl, butenyl and hexenyl; and alkynyl groups as defined herein and exemplified by ethynyl and propynyl. Alternatively, each R 11 It can be vinyl or hexenyl. Alternatively, each R 11 In certain embodiments, the alkenyl or alkynyl content of (A) organopolysiloxane may be 0.1% to 1%, alternatively 0.2% to 0.5%, based on the weight of (A) organopolysiloxane.

[0057] When (A) the organopolysiloxane further comprises an organopolysiloxane that is substantially linear, alternatively linear, at least two aliphatic unsaturated groups may be bonded to silicon atoms in a side chain position, a terminal position, or both a side chain position and a terminal position in the substantially linear or linear organopolysiloxane. As a specific example, (A) the organopolysiloxane may further comprise an organopolysiloxane that is substantially linear, alternatively linear, having an average unit formula:

[0058] [(CH3)3SiO 1 / 2 ]2[(CH3)2SiO 2 / 2 ] cc [(CH3)ViSiO 2 / 2 ] bb , wherein the subscripts bb and cc are as defined above, and Vi represents a vinyl group. With respect to this average formula, any methyl group may be replaced by a different monovalent hydrocarbon group (such as an alkyl group or an aryl group), and any vinyl group may be replaced by a different aliphatic unsaturated monovalent hydrocarbon group (such as an allyl group or a hexenyl group). Alternatively, as a specific example of a polyorganosiloxane having an average of at least two silicon-bonded aliphatic unsaturated groups per molecule, the (A) organopolysiloxane may include a substantially linear, alternatively linear, organopolysiloxane having an average formula: Vi(CH3)2SiO[(CH3)2SiO] cc Si(CH3)2Vi, wherein the subscripts cc and Vi are as defined above. Dimethyl polysiloxanes terminated with silicon-bonded vinyl groups can be used alone or in combination with the dimethyl, methyl-vinyl polysiloxanes disclosed immediately above as a component of the (A) organopolysiloxane. With respect to the average formula, any methyl group can be replaced by a different monovalent hydrocarbon group, and any vinyl group can be replaced by any terminal aliphatic unsaturated monovalent hydrocarbon group. Because at least two silicon-bonded aliphatic unsaturated groups can be either pendant or terminal, the (A) organopolysiloxane can alternatively have an average unit formula:

[0059] [Vi(CH3)2SiO 1 / 2 ]2[(CH3)2SiO 2 / 2 ] cc [(CH3)ViSiO 2 / 2 ] bb , wherein the subscripts bb, cc and Vi are as defined above.

[0060] When (A) the organopolysiloxane further comprises a substantially linear polyorganosiloxane, examples of the substantially linear polyorganosiloxane may include: dimethylpolysiloxane capped at both molecular ends with dimethylvinylsiloxy groups, methylphenylpolysiloxane capped at both molecular ends with dimethylvinylsiloxy groups, a copolymer of methylphenylsiloxane and dimethylsiloxane capped at both molecular ends with dimethylvinylsiloxy groups, a copolymer of methylvinylsiloxane and methylphenylsiloxane capped at both molecular ends with dimethylvinylsiloxy groups, a copolymer of methylvinylsiloxane and methylphenylsiloxane capped at both molecular ends with dimethylvinylsiloxy groups, A copolymer of methylvinylsiloxane and diphenylsiloxane terminated with an alkoxy group, a copolymer of methylvinylsiloxane, methylphenylsiloxane and dimethylsiloxane terminated with dimethylvinylsiloxy groups at both ends of the molecule, a copolymer of methylvinylsiloxane and methylphenylsiloxane terminated with trimethylsiloxy groups at both ends of the molecule, a copolymer of methylvinylsiloxane and diphenylsiloxane terminated with trimethylsiloxy groups at both ends of the molecule, and a copolymer of methylvinylsiloxane, methylphenylsiloxane and dimethylsiloxane terminated with trimethylsiloxy groups at both ends of the molecule.

[0061] Alternatively, (A) the organopolysiloxane may also comprise a substantially linear, alternatively linear, polyorganosiloxane selected from the group consisting of:

[0062] i) dimethylvinylsiloxy-terminated polydimethylsiloxane,

[0063] ii) dimethylvinylsiloxy-terminated poly(dimethylsiloxane / methylvinylsiloxane),

[0064] iii) dimethylvinylsiloxy-terminated polymethylvinylsiloxane,

[0065] iv) trimethylsiloxy-terminated poly(dimethylsiloxane / methylvinylsiloxane),

[0066] v) trimethylsiloxy-terminated polymethylvinylsiloxane,

[0067] vi) dimethylvinylsiloxy-terminated poly(dimethylsiloxane / methylvinylsiloxane),

[0068] vii) dimethylvinylsiloxy-terminated poly(dimethylsiloxane / methylphenylsiloxane),

[0069] viii) dimethylvinylsiloxy-terminated poly(dimethylsiloxane / diphenylsiloxane),

[0070] ix) phenyl, methyl, vinyl-siloxy-terminated polydimethylsiloxane,

[0071] x) dimethylhexenylsiloxy-terminated polydimethylsiloxane,

[0072] xi) dimethylhexenylsiloxy-terminated poly(dimethylsiloxane / methylhexenylsiloxane),

[0073] xii) dimethylhexenylsiloxy-terminated polymethylhexenylsiloxane,

[0074] xiii) trimethylsiloxy-terminated poly(dimethylsiloxane / methylhexenylsiloxane),

[0075] xiv) trimethylsiloxy-terminated polymethylhexenylsiloxane,

[0076] xv) dimethylhexenylsiloxy-terminated poly(dimethylsiloxane / methylhexenylsiloxane),

[0077] xvi) dimethylvinylsiloxy terminated poly(dimethylsiloxane / methylhexenylsiloxane), and

[0078] xvii) combinations thereof.

[0079] The composition may include (A) an organopolysiloxane in an amount of 60 wt % to 99.5 wt %, alternatively 60 wt % to 98 wt %, alternatively 60 wt % to 95 wt %, alternatively 70 wt % to 95 wt %, alternatively 75 wt % to 95 wt %, based on the total weight of the composition. In one embodiment, the (A) organopolysiloxane consists of a branched organopolysiloxane. In other embodiments in which the (A) organopolysiloxane comprises two or more different organopolysiloxanes (e.g., a branched organopolysiloxane and a substantially linear organopolysiloxane), based on the total weight of the (A) organopolysiloxane, the (A) organopolysiloxane typically comprises at least 50 wt %, alternatively at least 60 wt %, alternatively at least 70 wt %,

[0080] Alternatively, the branched organopolysiloxane is in an amount of at least 80 wt%, alternatively at least 90 wt%.

[0081] The composition also comprises (B) an organosilicon compound having an average of at least two silicon-bonded hydrogen atoms per molecule. The (B) organosilicon compound may be linear, branched, partially branched, cyclic, resinous (i.e., having a three-dimensional network), or may comprise a combination of different structures. The (B) organosilicon compound is typically a crosslinking agent and reacts with the ethylenically unsaturated groups of component (A) when forming a coating (e.g., a release coating). Typically, the (B) organosilicon compound comprises an organohydrogensiloxane.

[0082] The (B) organosilicon compound may contain any combination of M, D, T and / or Q siloxy units, so long as the (B) organosilicon compound includes at least two silicon-bonded hydrogen atoms per molecule. These siloxy units may be combined in a variety of ways to form cyclic, linear, branched and / or resinous (three-dimensional network) structures. Depending on the selection of M, D, T and / or Q units, the (B) organosilicon compound may be monomeric, polymeric, oligomeric, linear, branched, cyclic and / or resinous.

[0083] Since the (B) organosilicon compound contains an average of at least two silicon-bonded hydrogen atoms per molecule, with reference to the above-mentioned siloxy units, the (B) organosilicon compound may contain any of the following siloxy units containing silicon-bonded hydrogen atoms, optionally in combination with siloxy units not containing any silicon-bonded hydrogen atoms: (R 10 2HSiO 1 / 2 )、(R 10 H2SiO 1 / 2 )、(H3SiO 1 / 2 )、(R 10 HSiO 2 / 2 )、(H2SiO 2 / 2 ) and / or (HSiO 3 / 2 ), where each R 10 are independently selected and as defined above.

[0084] In a specific embodiment, the (B) organosilicon compound is a substantially linear, alternatively linear, polyorganohydrogensiloxane. The substantially linear or linear polyorganohydrogensiloxane may have an average unit formula: (HR 10 2SiO 1 / 2 ) v' (HR 10 SiO 2 / 2 ) w' (R 10 2SiO 2 / 2 ) z' (R 10 3SiO 1 / 2 ) y' , where each R 10Independently selected and as defined above, subscript v' is 0, 1 or 2, subscript w' is 1 or greater, subscript z' is 0 or greater, and subscript y' is 0, 1 or 2, provided that the amount (v'+y') = 2, and the amount (v'+w') ≥ 3. The amount (v'+w'+z'+y') can be 2 to 1,000. Examples of polyorganohydrogensiloxanes are:

[0085] i) a dimethylhydrogensiloxy-terminated poly(dimethyl / methylhydrogen)siloxane copolymer,

[0086] ii) dimethylhydrogensiloxy-terminated polymethylhydrogensiloxane,

[0087] iii) trimethylsiloxy-terminated poly(dimethyl / methylhydrogen)siloxane copolymer,

[0088] iv) trimethylsiloxy-terminated polymethylhydrogensiloxane and / or

[0089] v) A combination of two or more of i), ii), iii), iv) and v). Suitable polyorganohydrogensiloxanes are commercially available from Dow Silicones, Midland, Michigan, USA.

[0090] (B) The organosilicon compound may have the formula: y' R 10 3-y' Si-(OSiR 10 2) m -(OSiR 10 H) m' -OSiR 10 3-y' H y' , where each R 10 is an independently selected hydrocarbyl group free of aliphatic unsaturation, each y' is independently selected from 0 or 1, subscripts m and m' are each independently 0 to 1,000, provided that m and m' are not both 0, and m+m' is 1 to 1,000. In a specific embodiment, each of y' is 0, and subscript m'≥2.

[0091] In a specific embodiment, the (B) organosilicon compound is linear and includes pendant silicon-bonded hydrogen atoms. In these embodiments, the (B) organosilicon compound can be a dimethyl, methylhydrogen polysiloxane having the following average formula:

[0092] (CH3)3SiO[(CH3)2SiO] z' [(CH3)HSiO] w' Si(CH3)3

[0093] wherein z' and w' are as defined above. Those skilled in the art understand that in the above exemplary formula, the dimethylsiloxy units and methylhydrogensiloxy units may be present randomly or in blocks, and any methyl group may be substituted with any other hydrocarbon group that does not contain an aliphatic unsaturated group.

[0094] In another specific embodiment, the (B) organosilicon compound is linear and includes terminal silicon-bonded hydrogen atoms. In these embodiments, the (B) organosilicon compound can be a SiH-terminated dimethyl polysiloxane having the following average formula:

[0095] H(CH3)2SiO[(CH3)2SiO] z' Si(CH3)2H

[0096] wherein z' is as defined above. The SiH-terminated dimethyl polysiloxane may be utilized alone or in combination with the dimethyl, methyl hydrogen polysiloxanes disclosed directly above. When a mixture is used, the relative amounts of each organohydrogen siloxane in the mixture may vary. It will be appreciated by those skilled in the art that any methyl group in the above exemplary formula may be substituted with any other hydrocarbon group that does not contain an aliphatic unsaturated group.

[0097] Still alternatively, the (B) organosilicon compound may include pendant and terminal silicon-bonded hydrogen atoms.

[0098] In certain embodiments, the (B) organosilicon compound may comprise an alkylhydrogen cyclosiloxane or an alkylhydrogen dialkyl cyclosiloxane copolymer. Specific examples of suitable organohydrogen siloxanes of this type include (OSiMeH)4, (OSiMeH)3(OSiMeC6H 13 )、(OSiMeH)2(OSiMeC6H 13 )2 and (OSiMeH)(OSiMeC6H 13 )3, wherein Me represents methyl (-CH3).

[0099] (B) Other examples of suitable organohydrogensiloxanes of the organosilicon compound are those having at least two SiH-containing cyclosiloxane rings in one molecule. Such organohydrogensiloxanes can be any organopolysiloxane having at least two cyclosiloxane rings, each cyclosiloxane ring having at least one hydrogen (SiH) atom bonded to silicon. The cyclosiloxane rings contain at least three siloxane units (the minimum amount required to form a siloxane ring), and can be any combination of M, D, T, and / or Q siloxane units that form a cyclic structure, provided that at least one of the cyclic siloxane units on each siloxane ring contains an SiH unit, which can be an M siloxane unit, a D siloxane unit, and / or a T siloxane unit. When the other substituent is a methyl group, these siloxane units can be represented as MH, DH, and TH siloxane units, respectively.

[0100] In another specific embodiment, (B) the organosilicon compound has the formula: [(HR 10 SiO 2 / 2 ) a (-R 10 SiO 3 / 2 ) b c [(R 10 2SiO 2 / 2 ) w d , where each R 10 is independently selected and defined as above, subscript a is from 0 to 10; subscript b is from 1 to 4, provided that (a + b) = 3 to 12; 0 < c < 100; 2 ≤ w ≤ 2,000; and 0 < d < 100, provided that c > d. Such organosilicon compounds can be called branched cyclic polyorganohydrogensiloxane compounds, which have cyclic SiH-functional branched groups interconnected by linear polydiorganosiloxane segments. Exemplary structures associated with such branched cyclic polyorganohydrogensiloxane compounds are as follows:

[0101]

[0102] where each R 10 is independently selected and defined as above; subscript n is from 2 to 2,000, alternatively from 2 to 1,600, alternatively from 2 to 1,200, alternatively from 2 to 800, alternatively from 2 to 400, alternatively from 2 to 200, alternatively from 2 to 100, alternatively from 2 to 50; and each subscript o is independently from 0 to 9, alternatively from 0 to 8, alternatively from 0 to 6, alternatively from 0 to 4, alternatively from 2 to 4.

[0103] ​​Such branched cyclic polyorganohydrogensiloxane compounds are known in the art and can be prepared, for example, by combining (A) a hydroxyl-terminated polydiorganosiloxane and (B) a cyclic polyorganohydrogensiloxane in the presence of (C) a boron-containing Lewis acid.

[0104] The (B) organosilicon compound may include a combination of two or more different organosilicon compounds that differ in at least one property, such as structure, molecular weight, content of monovalent groups bonded to silicon atoms, and silicon-bonded hydrogen atoms. The composition may include an amount of (B) organosilicon compound such that the molar ratio of silicon-bonded hydrogen atoms in component (B) to silicon-bonded ethylenically unsaturated groups in component (A) is from 1:1 to 5:1, alternatively from 1.1:1 to 3.1.

[0105] The composition further comprises (C) a hydrosilylation reaction catalyst. (C) The hydrosilylation reaction catalyst comprises a catalyst having a formula ML x D y A metal-ligand complex wherein M is a metal; x is equal to the oxidation state of M; each D is independently a neutral coordinating ligand; y is 0 or an integer from 1 to 4; and each L is independently a monoanionic ligand having the formula:

[0106]

[0107] Each R 1 and R 2 is independently a halide or selected from C1-C6 alkyl, C3-C8 cycloalkyl, C3-C8 heterocycloalkyl, C6-C 10 Alkyl aryl, C1-C6 alkoxy, C6-C 10 Aryl, C6-C 10 Heteroaryl, silyl, C2-C8 alkenyl, C2-C8 alkynyl, C1-C6 hydroxyl, C3-C 10 Arylene, C3-C 10 Heteroarylene, C2-C 10 Alkenylene, C3-C 10 Cycloalkenylene and C2-C 10 A substituted or unsubstituted alkynylene group, wherein R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 Each of the following is independently selected from hydrogen, halide or C1-C6 alkyl, C3-C8 cycloalkyl, C3-C8 heterocycloalkyl, C6-C 10 Alkyl aryl, C1-C6 alkoxy, C6-C 10 Aryl, C6-C 10Heteroaryl, silyl, C2-C8 alkenyl, C2-C 10 Alkynyl, C1-C6 hydroxyl, C3-C 10 Arylene, C3-C 10 Heteroarylene, C2-C 10 Alkenylene, C3-C 10 Cycloalkenylene and C2-C 10 A substituted or unsubstituted group of alkynylene; and wherein E is C or Si.

[0108] In certain embodiments, R 1 and R 2 At least one of is not a fluorine (F-) or trifluoromethyl (CF3-) group. In some embodiments of these metal-ligand complexes, R 1 and R 2 At least one of is not a fluoride or a C1-C6 fluoroalkyl. In some embodiments of these metal-ligand complexes, each R 1 and R 2 is not fluoride or trifluoromethyl. In some embodiments, each R 1 and R 2 Not a fluoride or a C1-C6 fluoroalkyl.

[0109] In certain embodiments, M is selected from the group consisting of Li, Be, Mg, Ca, Sr, Ba, Al, Sc, Ga, Sn, Ti, Zr, Hf, V, Nb, Ta, Cr, Mo, W, Mn, Re, Fe, Ru, Os, Co, Rh, Ir, Ni, Pd, Pt, Cu, Ag, Au, Zn, lanthanide metals, and actinide metals. In some embodiments of the metal-ligand complexes disclosed herein, M is selected from the group consisting of Li, Be, Mg, Ca, Sr, Ba, Al, Sc, Ga, Sn, Ti, Zr, Hf, V, Nb, Ta, Cr, Mo, W, Mn, Re, Fe, Ru, Os, Rh, Ir, Ni, Pd, Pt, Cu, Ag, Au, Zn, lanthanide metals, and actinide metals. In other embodiments of the metal-ligand complexes disclosed herein, M is selected from the group consisting of Li, Mg, Rh, Ir, Pt, Ru, and Os. In specific embodiments of the metal-ligand complexes disclosed herein, M is selected from the group consisting of Pt, Li, Rh, and Ir. In other embodiments, M is selected from a platinum group metal selected from Ru, Rh, Pd, Os, Ir, and Pt. In exemplary embodiments of the metal-ligand complexes disclosed herein, M is Pt. In some embodiments of the metal-ligand complexes disclosed herein, the coordination number of M is 4 or 6. In some embodiments of the metal-ligand complexes disclosed herein, the coordination number of M is 4. In these or other embodiments, M has an oxidation number (also referred to as oxidation state) of at least +2.

[0110] In some embodiments of the metal-ligand complexes disclosed herein, L is n 1 ,η 2 In some embodiments of the metal-ligand complexes disclosed herein, when x is greater than 1, each L is the same. In some embodiments of the metal-ligand complexes disclosed herein, when x is greater than 1, each L is different from each other. In some embodiments of the metal-ligand complexes disclosed herein, each L except R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 The total number of carbon atoms other than the functional group R is independently 4 or 5. In some embodiments of the metal-ligand complexes disclosed herein, n is 0 or 1. In some embodiments of the metal-ligand complexes disclosed herein, each L except the functional group R 1 , R 2 , R 3, R 4 , R 5 , R 6 , R 7 , R 8 and R 9 is 5. In some embodiments of the metal-ligand complexes disclosed herein, n is 1. In some embodiments of the metal-ligand complexes disclosed herein, M is associated with each L via a metal-carbon sigma bond and a metal-olefin π bond. In some embodiments of the metal-ligand complexes disclosed herein, when x is greater than 1, the metal-carbon sigma bonds in the metal-ligand complex are cis relative to each other. In some embodiments of the metal-ligand complexes disclosed herein, each R 1 and R 2 independently selected from the group consisting of halides and substituted or unsubstituted groups, the substituted or unsubstituted groups selected from C1-C6 alkyl, C3-C8 cycloalkyl, C3-C8 heterocycloalkyl, C6-C 10 Alkyl aryl, C1-C6 alkoxy, C6-C 10 Aryl, C6-C 10 heteroaryl, silyl, C2-C8 alkenyl, C2-C8 alkynyl, or any combination thereof. In some embodiments of the metal-ligand complex disclosed herein, each R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 independently selected from the group consisting of hydrogen, halides and substituted or unsubstituted groups selected from C1-C6 alkyl, C3-C8 cycloalkyl, C3-C8 heterocycloalkyl, C6-C 10 Alkyl aryl, C1-C6 alkoxy, C6-C 10 Aryl, C6-C 10 heteroaryl, silyl, C2-C8 alkenyl, C2-C8 alkynyl, or any combination thereof. In some embodiments of the metal-ligand complex disclosed herein, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are directly or indirectly connected to each other via an alkyl group and / or a fluoroalkyl group. In some embodiments of the metal-ligand complex disclosed herein, R 1 , R 2 , R 3, R 4 , R 5 , R 6 , R 7 , R 8 and R 9 Indirectly linked to each other via an alkyl group and / or a fluoroalkyl group. In some embodiments of the metal-ligand complexes disclosed herein, L is a bidentate ligand.

[0111] In some embodiments of the metal-ligand complexes disclosed herein, E is Si. In other embodiments, E is C.

[0112] In some embodiments of the metal-ligand complexes disclosed herein, each D independently comprises an ether group (R 12 2O), amine group (R 12 3N), nitrile group (R 12 CN), isonitrile group (R 12 NC), phosphine group (R 12 3P), phosphite group ((R 12 O)3P), arsenic group (R 12 3As), antimony group (R 12 3Sb), sulfide group (CS), linear, branched or cyclic monoolefin, linear, branched or cyclic diene, linear, branched or cyclic triene, bicycloolefin, bicyclodiene, bicyclotriene, tricyclodiene, tricyclotriene, alkyne and any combination thereof; wherein each R 12 independently selected from the group consisting of substituted or unsubstituted groups, the substituted or unsubstituted groups are selected from C1-C6 alkyl, C3-C8 cycloalkyl, C3-C8 heterocycloalkyl, C6-C 10 Alkyl aryl, C1-C6 alkoxy, C6-C 10 Aryl a C6-C 10 Heteroaryl, silyl, C2-C8 alkenyl, C2-C8 alkynyl, C1-C6 hydroxyl, C3-C 10 Arylene, C3-C 10 Heteroarylene, C2-C 10 Alkenylene, C3-C 10 Cycloalkenylene, C2-C 10Alkyne and any combination thereof. In some embodiments of the metal-ligand complex disclosed herein, each D is independently selected from the group consisting of linear monoether, linear polyether, cyclic monoether, cyclic polyether, monoamine, linear polyamine, cyclic monoamine, cyclic polyamine and any combination thereof. In a specific embodiment, each D is independently selected from the group consisting of 1,5-cyclooctadiene, bicyclo[2.2.1]hept-2,5-diene, 1,5-hexadiene, ethylene, dibenzo[a,e]cyclooctene, N,N,N',N'-tetramethylethylenediamine, norbornadiene, cyclooctatriene and cyclooctene. In an exemplary embodiment, each D is 1,5-cyclooctadiene. In other embodiments, D can be a molecule that is otherwise present in the composition for another purpose. For example, D can be a solvent molecule, such as acetonitrile, THF, polyether, etc. For another example, D can be an inhibitor molecule, such as 1-ethynylcyclohexanol. The optional components of the composition are described below, and those skilled in the art will readily understand which optional components can be used as D based on the description herein.

[0113] In some embodiments of the metal-ligand complexes disclosed herein, the metal-ligand complex is a neutral metal-ligand complex. In some embodiments of the metal-ligand complexes disclosed herein, y is 0. In some embodiments of the metal-ligand complexes disclosed herein, the metal-ligand complex is selected from the group consisting of: (2,2-dimethylpent-4-en-1-yl)lithium, cis-bis(η 1 ,η 2 -2,2-dimethylbut-3-en-1-yl)platinum, cis-bis(η 1 ,η 2 -2,2-dimethylpent-4-en-1-yl)platinum, cis-bis(η 1 ,η 2 -2,2-dimethylhex-5-en-1-yl) platinum, [(1,2,5,6-η)-1,5-cyclooctadiene] (η 1 ,η 2 -2,2-dimethylpent-4-en-1-yl)iridium, [(1,2,5,6-η)-1,5-cyclooctadiene](η 1 ,η 2 -2,2-dimethylpent-4-en-1-yl)rhodium and [(2,3,5,6-η)-bicyclo[2.2.1]hept-2,5-diene] (η 1 ,η 2 -2,2-dimethylpent-4-en-1-yl)rhodium.

[0114] In some embodiments of the metal-ligand complexes disclosed herein, M is a platinum group metal selected from Ru, Rh, Pd, Os, Ir, and Pt, and E is Si. In these or other embodiments, R1 and R 2 are independently selected alkyl groups, and R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 In these or other embodiments, each D is independently 1,5-cyclooctadiene, bicyclo[2.2.1]hepta-2,5-diene, 1,5-hexadiene, ethylene, dibenzo[a,e]cyclooctene, N,N,N',N'-tetramethylethylenediamine, or acetonitrile.

[0115] In certain embodiments, the metal-ligand complex of component (C) undergoes two different activation steps to allow components (A) and (B) to undergo hydrosilylation reaction and cure the composition to obtain a release coating. For example, in certain embodiments, when component (C) is incorporated into the composition, it may be an initial catalyst. In these embodiments, the subscript y is generally greater than 0, and D is present in the metal-ligand complex. D may be selected to inhibit the catalytic activity of M in the metal-ligand complex. In the first activation step, D may dissociate from M in the metal-ligand complex to obtain a pre-catalyst in which the subscript y is 0 and D is absent. In certain embodiments, after D dissociates, each L may be combined with M via the olefinic unsaturation present in each L. The second activation step is a step that results in a catalytically active form of M in the composition. In certain embodiments, each activation step is performed without any specific initiation. In other embodiments, each activation step is performed when exposed to an elevated temperature, such as 50°C to 200°C.

[0116] In certain embodiments, component (C) comprises an initial catalyst when incorporated into the composition, wherein subscript y is 1 and D is 1,5-cyclooctadiene, x is 2, and in each L, M is Pt, E is Si, R 1 and R 2 are independently selected alkyl groups, and R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 In this embodiment, when R 1 and R 2 When is a methyl group, the initial catalyst has the formula:

[0117] Each subscript n is from 0 to 2.

[0118] In these or other embodiments, after D is dissociated to obtain the precatalyst, ie, when the subscript y is 0, the precatalyst has the formula:

[0119] wherein each subscript n is independently 0 to 2.

[0120] (C) The hydrosilylation catalyst is present in the composition in a catalytic amount, i.e., an amount or quantity sufficient to promote its curing under the desired conditions. The hydrosilylation catalyst can be a single hydrosilylation catalyst or a mixture comprising two or more different hydrosilylation catalysts.

[0121] The catalytic amount of (C) hydrosilylation reaction catalyst may be >0.01 ppm to 10,000 ppm; alternatively >1,000 ppm to 5,000 ppm. Alternatively, a typical catalytic amount of (C) hydrosilylation reaction catalyst is 0.1 ppm to 5,000 ppm, alternatively 1 ppm to 2,000 ppm, alternatively >0 ppm to 1,000 ppm. Alternatively, the catalytic amount of (C) hydrosilylation reaction catalyst may be 0.01 ppm to 1,000 ppm, alternatively 0.01 ppm to 100 ppm, alternatively 20 ppm to 200 ppm, and alternatively 0.01 ppm to 50 ppm of M; the above catalytic amounts are based on the total weight of the composition.

[0122] The composition may further comprise one or more of the following: (D) an inhibitor, (E) an anchor additive, (F) an anti-fog additive, (G) an anti-sticking modifier, and (H) a vehicle.

[0123] In certain embodiments, the composition further comprises (D) an inhibitor. (D) An inhibitor can be used to change the reaction rate or curing rate of the composition compared to a composition comprising the same starting materials but omitting the (D) inhibitor. Examples of (D) inhibitors include alkynols such as methyl butynol, ethynyl cyclohexanol, dimethyl hexynol, and 3,5-dimethyl-1-hexyn-3-ol, 1-butyn-3-ol, 1-propyn-3-ol, 2-methyl-3-butyn-2-ol, 3-methyl-1-butyn-3-ol, 3-methyl-1-pentyn-3-ol, 3-phenyl-1-butyn-3-ol, 4-ethyl-1-octyne-3-ol, and 1-ethynyl-1-cyclohexanol and combinations thereof; cycloalkenyl siloxanes such as methyl vinyl cyclosiloxanes, exemplified by 1,3,5,7-tetramethyl-1,3,5,7-tetravinyl Cyclotetrasiloxane, 1,3,5,7-tetramethyl-1,3,5,7-tetrahexenylcyclotetrasiloxane and combinations thereof; enyne compounds such as 3-methyl-3-pentene-1-yne, 3,5-dimethyl-3-hexene-1-yne; triazoles such as benzotriazole; phosphines; thiols; hydrazines; amines such as tetramethylethylenediamine; fumaric acid dialkyl esters, fumaric acid dienyl esters, fumaric acid dialkoxyalkyl esters; maleic acid esters such as maleic acid diallyl ester; nitriles; ethers; carbon monoxide; olefins such as cyclooctadiene, divinyltetramethyldisiloxane; alcohols such as benzyl alcohol; and combinations thereof. Alternatively, the (D) inhibitor may be selected from the group consisting of alkynols (eg, 1-ethynyl-1-cyclohexanol) and maleates (eg, diallyl maleate, bismaleate or n-propyl maleate) and combinations of two or more thereof.

[0124] Alternatively, (D) the inhibitor may be a silylated acetylenic compound. Without wishing to be bound by theory, it is believed that the addition of a silylated acetylenic compound reduces the yellowing of the reaction product prepared by the hydrosilylation reaction of the composition compared to the reaction product obtained by the hydrosilylation of the composition not comprising a silylated acetylenic compound or comprising an organic acetylenic alcohol inhibitor such as those described above.

[0125] Examples of silylated acetylenic compounds are (3-methyl-1-butyn-3-oxy)trimethylsilane, ((1,1-dimethyl-2-propynyl)oxy)trimethylsilane, bis(3-methyl-1-butyn-3-oxy)dimethylsilane, bis(3-methyl-1-butyn-3-oxy)silanemethylvinylsilane, bis((1,1-dimethyl-2-propynyl)oxy)dimethylsilane, methyl(tris(1,1-dimethyl-2-propynyloxy))silane, methyl(tris(3-methyl-1-butyn-3-oxy))silane, (3-methyl-1-butyn-3-oxy)dimethylphenylsilane, (3-methyl-1-butyn-3-oxy)dimethylhexenylsilane, (3-methyl-1-butyn-3-oxy)triethylsilane. 1-Hexyne-3-oxy)trimethylsilane, (3-phenyl-1-butyne-3-oxy)diphenylmethylsilane, (3-phenyl-1-butyne-3-oxy)dimethylphenylsilane, (3-phenyl-1-butyne-3-oxy)dimethylvinylsilane, (3-phenyl-1-butyne-3-oxy)dimethylhexenylsilane, (cyclohexyl-1-ethynyl-1-oxy)dimethylhexenylsilane, (cyclohexyl-1-ethynyl-1-oxy)dimethylvinylsilane, (cyclohexyl-1-ethynyl-1-oxy)diphenylmethylsilane, (cyclohexyl-1-ethynyl-1-oxy)trimethylsilane, and combinations thereof. Alternatively, the (D) inhibitor is exemplified by methyl(tris(1,1-dimethyl-2-propynyloxy))silane, ((1,1-dimethyl-2-propynyl)oxy)trimethylsilane, or a combination thereof. The silylated acetylenic compound useful as the (D) inhibitor may be prepared by a method known in the art, such as by reacting the above acetylenic alcohol with a chlorosilane in the presence of an acid acceptor to silylate the above acetylenic alcohol.

[0126] The amount of (D) inhibitor present in the composition will depend on various factors, including the desired soak life of the composition, whether the composition will be a one-part or multi-part composition, the specific inhibitor used, and the selection and amounts of components (A) to (C). However, when (D) inhibitor is present, the amount of inhibitor (D) may be 0% to 1%, alternatively 0% to 5%, alternatively 0.001% to 1%, alternatively 0.01% to 0.5%, and alternatively 0.0025% to 0.025%, based on the total weight of the composition.

[0127] Conventional compositions for preparing release coatings typically include a Karstedt catalyst (a platinum complex well known in the art) in combination with an inhibitor to extend the soak life and prevent premature curing. However, the combination of the Karstedt catalyst and the inhibitor in the known conventional compositions can cause undesirable precipitation and color changes over time, which is undesirable and problematic in the entire release coating industry. Precipitation adversely affects the performance characteristics of release coatings and shortens the soak life. In contrast, when the (D) inhibitor is present (if used), component (C) generally does not cause any precipitation or color change. It is also important that, although it is necessary to use an inhibitor together with a conventional catalyst such as a Karstedt catalyst in a conventional composition for preparing a release coating, the inhibitor is optional in view of the performance characteristics of component (C).

[0128] In certain embodiments, the composition does not contain component (D). In other embodiments, component (D) is present. In specific embodiments, the composition comprises a certain amount of component (D) so that the molar ratio of component (D) to M in component (C) (M in (D) / (C)) is 0 to 20:1, alternatively 0 to 15:1, alternatively greater than 0 to 15:1, alternatively greater than 0 to 12:1, alternatively greater than 0 to 9:1, alternatively greater than 0 to 6:1, alternatively greater than 0 to 3:1, alternatively greater than 0 to 2:1, alternatively greater than 1:1 to 10:1, alternatively greater than 1:1 to 8:1, alternatively greater than 1:1 to 6:1, alternatively greater than 1:1 to 4:1, alternatively greater than 1:1 to 2:1.

[0129] In certain embodiments, the composition further comprises (E) a fixing additive. Examples of suitable fixing additives include reaction products of vinyl alkoxysilanes and epoxy-functionalized alkoxysilanes; reaction products of vinyl acetoxysilanes and epoxy-functionalized alkoxysilanes; and combinations (e.g., physical blends and / or reaction products) of polyorganosiloxanes having at least one aliphatic unsaturated hydrocarbon group and at least one hydrolyzable group per molecule and epoxy-functionalized alkoxysilanes (e.g., combinations of hydroxyl-terminated vinyl-functionalized polydimethylsiloxanes and glycidoxypropyltrimethoxysilanes). Alternatively, the fixing additive may include a polyorganosilicate resin. Suitable fixing additives and methods for preparing the same are disclosed in, for example, U.S. Pat. No. 9,562,149, U.S. Patent Application Publication Nos. 2003 / 0088042, 2004 / 0254274, and 2005 / 0038188, and European Patent No. 0 556 023.

[0130] Other examples of suitable fixing additives may include transition metal chelates, hydrocarbonoxysilanes (such as alkoxysilanes), combinations of alkoxysilanes and hydroxy-functional polyorganosiloxanes, or combinations thereof. The (E) fixing additive may be a silane having at least one substituent having an adhesion promoting group, such as an epoxy group, an acetoxy group, or an acrylate group. Additionally or alternatively, the adhesion promoting group may be any hydrolyzable group that does not affect the (C) hydrosilylation reaction catalyst. Alternatively, the (E) fixing additive may include a partial condensate of such silanes, such as an organopolysiloxane having an adhesion promoting group. Also alternatively, the (E) fixing additive may include a combination of an alkoxysilane and a hydroxy-functional polyorganosiloxane.

[0131] Alternatively, (E) the fixing additive may include an unsaturated compound or an epoxy-functional compound. (E) The fixing additive may include an unsaturated alkoxysilane or an epoxy-functionalized alkoxysilane. For example, the functionalized alkoxysilane may contain at least one unsaturated organic group or an epoxy-functionalized organic group. Examples of epoxy-functionalized organic groups include 3-glycidyloxypropyl and (epoxycyclohexyl)ethyl. Unsaturated organic groups are, for example, 3-methacryloxypropyl, 3-acryloxypropyl, and unsaturated monovalent hydrocarbon groups such as vinyl, allyl, hexenyl, undecenyl. A specific example of an unsaturated compound is vinyl triacetoxysilane.

[0132] Specific examples of suitable epoxy-functional alkoxysilanes include 3-glycidyloxypropyltrimethoxysilane, 3-glycidyloxypropyltriethoxysilane, (epoxycyclohexyl)ethyldimethoxysilane, (epoxycyclohexyl)ethyldiethoxysilane, and combinations thereof. Examples of suitable unsaturated alkoxysilanes include vinyltrimethoxysilane, allyltrimethoxysilane, allyltriethoxysilane, hexenyltrimethoxysilane, undecenyltrimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-methacryloxypropyltriethoxysilane, 3-acryloxypropyltrimethoxysilane, 3-acryloxypropyltriethoxysilane, and combinations thereof.

[0133] The (E) anchor additive may also include a reaction product or partial reaction product of one or more of these compounds. For example, in a specific embodiment, the (E) anchor additive may include a reaction product or partial reaction product of vinyl triacetoxysilane and 3-glycidoxypropyl trimethoxysilane. Alternatively or in addition, the (E) anchor additive may include an alkoxy or alkenyl functionalized siloxane.

[0134] Alternatively, the (E) anchor additive may include an epoxy-functionalized siloxane, such as a reaction product of a hydroxy-terminated polyorganosiloxane and an epoxy-functionalized alkoxysilane as described above, or a physical blend of a hydroxy-terminated polyorganosiloxane and an epoxy-functionalized alkoxysilane. The (E) anchor additive may include a combination of epoxy-functionalized alkoxysilanes and epoxy-functionalized siloxanes. For example, an example of the (E) anchor additive D is a mixture of 3-glycidoxypropyltrimethoxysilane and a reaction product of a hydroxy-terminated methylvinylsiloxane and 3-glycidoxypropyltrimethoxysilane, or a mixture of 3-glycidoxypropyltrimethoxysilane and a hydroxy-terminated methylvinylsiloxane, or a mixture of 3-glycidoxypropyltrimethoxysilane and a hydroxy-terminated methylvinylsiloxane, or a mixture of 3-glycidoxypropyltrimethoxysilane and a hydroxy-terminated methylvinyl / dimethylsiloxane copolymer.

[0135] Alternatively, (E) the fixing additive may include a transition metal chelate. Suitable transition metal chelates include titanates, zirconates (such as zirconium acetylacetonate), aluminum chelates (such as aluminum acetylacetonate), and combinations thereof. Alternatively, (E) the fixing additive may include a combination of a transition metal chelate and an alkoxysilane, such as a combination of glycidyloxypropyltrimethoxysilane and an aluminum chelate or a zirconium chelate.

[0136] If used, the specific amount of (E) fixing additive present in the composition depends on various factors, including the type of substrate and whether a primer is used. In certain embodiments, the (E) fixing additive is present in the composition in an amount of 0 to 2 parts by weight per 100 parts by weight of component (B). Alternatively, the (E) fixing additive is present in the composition in an amount of 0.01 to 2 parts by weight per 100 parts by weight of component (B).

[0137] In certain embodiments, the composition further comprises (F) an anti-fog additive. (F) The anti-fog additive can be used in the composition to reduce or inhibit the formation of organosilicon mist during the coating process, particularly during the coating process using a high-speed coating device. (F) The anti-fog additive can be a reaction product of an organohydrogen silicon compound, an oxyalkylene compound, or an organoalkenylsiloxane having at least three silicon-bonded alkenyl groups per molecule and a suitable catalyst. Suitable anti-fog additives are disclosed in, for example, U.S. Patent Application 2011 / 0287267, U.S. Patent 8,722,153, U.S. Patent 6,586,535, and U.S. Patent 5,625,023.

[0138] The amount of (F) anti-fog additive used in the composition will depend on various factors, including the amount and type of other starting materials selected for the composition. However, the (F) anti-fog additive is generally used in an amount of 0% to 10%, alternatively 0.1% to 3%, based on the total weight of the composition.

[0139] In certain embodiments, the composition further comprises (G) an anti-adhesion modifier, which can be used in the composition to control (reduce) the level of peeling force (adhesion between the anti-adhesion coating formed by the composition and its adherend (such as a label comprising a pressure-sensitive adhesive)). By adjusting the level or concentration of the (G) anti-adhesion modifier, an anti-adhesion coating with a required or desired peeling force can be prepared by a composition without a modifier. Examples of suitable anti-adhesion modifiers for component (G) include dimethyl and phenylmethylsiloxanes terminated with trimethylsiloxy. Alternatively, (G) anti-adhesion modifiers can be condensation products of an organopolysiloxane resin with a hydroxyl or alkoxy group and a diorganopolysiloxane with at least one hydroxyl or hydrolyzable group. Examples of suitable anti-adhesion modifiers are disclosed in, for example, U.S. Patent No. 8,933,177 and U.S. Patent Application Publication No. 2016 / 0053056. When used, the (G) anti-adhesion modifier may be present in the composition in an amount of 0 to 85 parts by weight, alternatively 25 to 85 parts by weight, per 100 parts of component (A).

[0140] In certain embodiments, the composition further comprises (H) a vehicle. The (H) vehicle generally dissolves the components of the composition, and if the components are dissolved, the (H) vehicle may be referred to as a solvent. Suitable vehicles include silicones (both linear and cyclic), organic oils, organic solvents, and mixtures of these.

[0141] Typically, the (H) vehicle, if present in the composition, is an organic liquid. Organic liquids include those considered oils or solvents. Organic liquids are exemplified by, but not limited to, aromatic hydrocarbons, aliphatic hydrocarbons, alcohols having more than 3 carbon atoms, aldehydes, ketones, amines, esters, ethers, glycols, glycol ethers, alkyl halides, and aromatic halides. Hydrocarbons include isododecane, isohexadecane, Isopar L (C11 to C13), Isopar H (C11 to C12), hydrogenated polydecene, aromatic hydrocarbons, and halogenated hydrocarbons. Ethers and esters include isodecyl neopentanoate, neopentyl glycol heptanoate, glycol distearate, dicaprylyl carbonate, diethylhexyl carbonate, propylene glycol n-butyl ether, ethyl-3 ethoxypropionate, propylene glycol methyl ether acetate, tridecyl neopentanoate, propylene glycol methyl ether acetate (PGMEA), propylene glycol methyl ether (PGME), octadecyl neopentanoate, diisobutyl adipate, diisopropyl adipate, propylene glycol dicaprylate / dicaprate, octyl ether and octyl palmitate. Additional organic fluids suitable as independent compounds or as components of (H) vehicle include fats, oils, fatty acids and fatty alcohols. (H) vehicle may also be a 25° C. viscosity of 1 mm 2 / sec to 1,000mm 2 / second range, such as hexamethylcyclotrisiloxane, octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, dodecamethylcyclohexasiloxane, octamethyltrisiloxane, decamethyltetrasiloxane, dodecamethylpentasiloxane, tetradecamethylhexasiloxane, hexadecamethylheptasiloxane, heptamethyl-3-{(trimethylsilyl)oxy)}trisiloxane, hexamethyl-3,3,bis{(trimethylsilyl)oxy}trisiloxane, pentamethyl{(trimethylsilyl)oxy}cyclotrisiloxane, as well as polydimethylsiloxane, polyethylsiloxane, polymethylethylsiloxane, polymethylphenylsiloxane, polydiphenylsiloxane, caprylylmethicone, and any mixture thereof.

[0142] In a specific embodiment, the (H) vehicle is selected from polyalkylsiloxanes; tetrahydrofuran; mineral spirits; naphtha; alcohols such as methanol, ethanol, isopropanol, butanol or n-propanol; ketones such as acetone, methyl ethyl ketone or methyl isobutyl ketone; aromatic hydrocarbons such as benzene, toluene or xylene; aliphatic hydrocarbons such as heptane, hexane or octane; glycol ethers such as propylene glycol methyl ether, dipropylene glycol methyl ether, propylene glycol n-butyl ether, propylene glycol n-propyl ether or ethylene glycol n-butyl ether; or combinations thereof.

[0143] The amount of (H) vehicle will depend on various factors, including the type of selected vehicle and the amount and type of other components present in the composition. However, the amount of (H) vehicle in the composition can be 0% to 99%, alternatively 2% to 50% based on the gross weight of the composition. (H) vehicle can be added during the preparation of the composition, for example, to help mixing and delivery. After the preparation of the composition, including before and / or while the release coating is prepared by the composition, all or part of (H) vehicle can be optionally removed. In certain embodiments, the composition does not contain (H) vehicle, and the composition is solvent-free and does not contain solvents and vehicles, including organic solvents.

[0144] Other optional components may be present in the composition, including, for example, reactive diluents, fragrances, preservatives, colorants, dyes, pigments, antioxidants, heat stabilizers, flame retardants, flow control additives, biocides, fillers (including extending and reinforcing fillers), surfactants, thixotropic agents, pH buffers, etc. The composition may be in any form and may be incorporated into other compositions.

[0145] Alternatively, the composition and the release coating formed therefrom may be particle-free or contain only a limited amount of particles (e.g., filler and / or pigment), such as 0 wt % to 30 wt % of the composition. Particles may agglomerate or otherwise adhere to the coating machine equipment for forming the release coating. In addition, if optical transparency is desired, particles may hinder the optical properties of the release coating and the release liner formed therefrom, such as transparency. Particles may be unfavorable for the adhesion to the adherend.

[0146] In certain embodiments, the composition does not contain fluorine-containing organosiloxane compounds. It is believed that during curing, fluorine-containing compounds can quickly migrate to the interface of the composition or the release coating formed therefrom and the substrate to which the composition is applied and the release coating is formed, such as the composition / PET film interface, due to its low surface tension. Such migration can prevent the release coating (prepared by curing composition) from adhering to the substrate by preparing a fluorine-containing barrier. By preparing a barrier, fluorine-containing organosiloxane compounds can prevent any component of the composition from reacting at the interface, thereby affecting curing and related properties. In addition, fluorine-containing organosiloxane compounds are typically expensive.

[0147] The composition in its curable form can be prepared by combining components (A) to (C) and any optional components (as described above) in any order of addition, optionally with a masterbatch, and optionally under shear. As described in more detail below, the composition can be a one-part composition, a two-component or 2K composition, or a multi-part composition. For example, components (A), (B) and (C) can be present in the same or different parts until a soaking bath for preparing the release coating is formed.

[0148] In certain embodiments, the soaking life of the composition at 40°C is 10 minutes, alternatively 20 minutes, alternatively 30 minutes, alternatively 40 minutes. In a specific embodiment, the composition has such soaking life even in the absence of any (D) inhibitor. The soaking life is the time taken for the viscosity of the composition to double at 40°C, and thus indicates stability. The longer the soaking life, the better the coating performance. As understood in the art, the viscosity can be measured continuously at 40°C by a suitable viscometer (e.g., Brookfield DV2TLV viscometer). Conventional compositions for preparing release coatings can usually only achieve such soaking life when using quite high concentrations of inhibitors.

[0149] The method for preparing a coated substrate with a composition includes applying (i.e., arranging) the composition on a substrate. The method also includes curing the composition on the substrate, which results in forming a release coating on the substrate to obtain a coated substrate. Curing can be carried out by heating at an elevated temperature (e.g., 50°C to 200°C, alternatively 50°C to 180°C, and alternatively 50°C to 160°C) to obtain a coated substrate. Those skilled in the art will be able to select an appropriate temperature according to various factors, including the composition and the selection of the substrate composition or material of the structure.

[0150] The composition can be arranged or distributed on the substrate in any suitable manner. Typically, the composition is applied in wet form by a wet coating technique. The composition can be applied by i) spin coating; ii) brush coating; iii) drip coating; iv) spray coating; v) dip coating; vi) roller coating; vii) flow coating; viii) slot coating; ix) concave coating; x) Mayer rod coating; or xi) any combination of two or more of i) to x). Typically, the composition is arranged on the substrate to result in a wet deposit on the substrate, which is then cured to obtain a coated substrate comprising a cured film (i.e., a release coating) formed by the composition on the substrate.

[0151] The substrate is not limited and can be any substrate. The release coating can be separated from the substrate, or can be physically and / or chemically bonded to the substrate according to its selection. The substrate can have an integrated hot plate or an integrated or independent stove for curing the wet deposit. The substrate can optionally have a continuous or discontinuous shape, size, dimension, surface roughness and other characteristics. Alternatively, the substrate has a softening point temperature at an elevated temperature. However, the composition and method are not limited thereto.

[0152] Alternatively, the substrate may comprise plastic, which may be thermosetting and / or thermoplastic. However, alternatively, the substrate may be or comprise glass, metal, cellulose (e.g. paper), wood, cardboard, paperboard, silicone or a polymer material or a combination thereof.

[0153] Specific examples of suitable substrates include paper stock such as kraft paper, polyethylene coated kraft paper (PEK coated paper), thermal paper and conventional paper; polymer substrates such as polyamide (PA); polyesters such as polyethylene terephthalate (PET), polybutylene terephthalate (PET), polytrimethylene terephthalate (PTT), polyethylene naphthalate (PEN) and liquid crystal polyesters; polyolefins such as polyethylene (PE), polypropylene (PP) and polybutylene; styrene resins; polyoxymethylene (POM); polycarbonate (PC); polymethyl methacrylate (PMMA); polyvinyl chloride (PVC); polyphenylene sulfide (PPS); poly Phenyl ether (PPE); polyimide (PI); polyamide-imide (PAI); polyetherimide (PEI); polysulfone (PSU); polyethersulfone; polyketone (PK); polyetherketone; polyvinyl alcohol (PVA); polyetheretherketone (PEEK); polyetherketoneketone (PEKK); polyarylate (PAR); polyethernitrile (PEN); phenolic resin; phenoxy resin; cellulose, such as triacetyl cellulose, diacetyl cellulose and cellophane; fluorinated resins, such as polytetrafluoroethylene; thermoplastic elastomers, such as polystyrene type, polyolefin type, polyurethane type, polyester type, polyamide type, polybutadiene type, polyisoprene type and fluorine type; and copolymers and combinations thereof.

[0154] Composition or wet deposit are solidified for a period of time at a temperature raised usually.This period of time is usually enough to realize the solidification of composition, i.e. crosslinked.This period of time can be greater than 0 hour to 8 hours, alternatively greater than 0 hour to 2 hours, alternatively greater than 0 hour to 1 hour, alternatively greater than 0 minute to 30 minutes, alternatively greater than 0 minute to 15 minutes, alternatively greater than 0 minute to 10 minutes, alternatively greater than 0 minute to 5 minutes, alternatively greater than 0 minute to 2 minutes, alternatively greater than 0 minute to 1 minute, alternatively greater than 0 second to 50 seconds, alternatively greater than 0 second to 40 seconds, alternatively greater than 0 second to 30 seconds, alternatively greater than 0 second to 20 seconds, alternatively greater than 0 second to 10 seconds, alternatively greater than 0 second to 5 seconds.This period of time depends on various factors, including the presence or absence of any vehicle in the temperature of used rising, selected temperature, the release coating thickness of expectation and the composition.

[0155] The composition is cured typically with a dwell time of 0.1 to 50 seconds, alternatively 0.5 to 30 seconds, alternatively 1 to 10 seconds. The selected dwell time may depend on substrate selection, selected temperature and line speed. As used herein, the dwell time refers to the time during which the composition or wet deposit is subjected to elevated temperatures. The dwell time is different from the curing time because even after the composition, wet deposit or its partially cured reaction intermediate is no longer subjected to elevated temperatures (i.e., typically initiating curing), curing may be in progress. Alternatively, the coated substrate may be prepared on a conveyor belt in an oven, and the dwell time may be calculated by dividing the length of the oven (e.g., in meters) by the line speed of the conveyor belt (e.g., in meters per second). In some embodiments, the dwell time may be equal to a period of time during which the composition or wet deposit is cured.

[0156] The period of time can be broken down into curing iterations, e.g., a first cure and a post cure, where the first cure is, e.g., 1 hour, and the post cure is, e.g., 3 hours. The elevated temperature can be independently selected from any temperature above room temperature in such iterations, and can be the same in each iteration.

[0157] Depending on the optional presence and selection of the (H) vehicle, curing the composition may further include a drying step. For example, when the composition includes the (H) vehicle, the curing step typically also includes drying, volatilizing or removing the (H) vehicle in the composition. Drying may be performed simultaneously with curing or may be performed separately from curing.

[0158] According to the thickness and other dimensions of the release coating and the coated substrate, the coated substrate can be formed by an iterative process. For example, the first deposit can be formed and the first deposit is subjected to the first elevated temperature for a period of time to obtain a partially cured deposit. Then, the second deposit can be arranged on the partially cured deposit, and the second deposit is subjected to the second elevated temperature for a period of time to obtain the second partially cured deposit. The partially cured deposit will also be further cured for a period of time during exposure to the second elevated temperature. The third deposit can be arranged on the second partially cured deposit and is subjected to the third elevated temperature for a period of time to obtain the third partially cured deposit. The second partially cured deposit will also be further cured for a period of time during exposure to the second elevated temperature. The process can be repeated for example 1 to 50 times to construct a coated substrate as required. Composite has a partially cured layer, which can be subjected to final post-curing, for example, under the elevated temperature and time period above. Each elevated temperature and time period can be independently selected, and can be the same or different from each other. When forming the coated substrate by an iterative process, each deposit may also be independently selected and may differ in the composition selected, their amount, or both. Alternatively still, in such an iterative process, each iterative layer may be fully cured, rather than only partially cured.

[0159] Alternatively, each deposit may comprise or be a wet film. Alternatively, the iterative process may be wet-on-wet, depending on the state of cure of the partially cured layer. Alternatively, the iterative process may be wet-on-dry.

[0160] The coated substrate (which includes a release coating formed by a composition on a substrate) may have different sizes, including the relative thickness of the release coating and the substrate. The thickness of the release coating may vary depending on its end-use application. The thickness of the release coating may be greater than 0 μm to 4,000 μm, alternatively greater than 0 μm to 3,000 μm, alternatively greater than 0 μm to 2,000 μm, alternatively greater than 0 μm to 1,000 μm, alternatively greater than 0 μm to 500 μm, alternatively greater than 0 μm to 250 μm. However, other thicknesses, for example, 0.1 μm to 200 μm, are conceivable. For example, the thickness of the anti-stick coating may be 0.2 μm to 175 μm; alternatively 0.5 μm to 150 μm; alternatively 0.75 μm to 100 μm; alternatively 1 μm to 75 μm; alternatively 2 μm to 60 μm; alternatively 3 μm to 50 μm; and alternatively 4 μm to 40 μm. Alternatively, when the substrate is plastic, the thickness of the anti-stick coating may be greater than 0 μm to 200 μm, alternatively greater than 0 μm to 150 μm, and alternatively greater than 0 μm to 100 μm.

[0161] If necessary, the release coating can be further processed according to the final use application of the release coating. For example, the release coating can be subjected to oxidation deposition (for example, SiO2 deposition), resist deposition and patterning, etching, chemical, corona or plasma stripping, metallization or metal deposition treatment. Such further processing techniques are generally known. Such deposition can be chemical vapor deposition (including low pressure chemical vapor deposition, plasma enhanced chemical vapor deposition and plasma assisted chemical vapor deposition), physical vapor deposition or other vacuum deposition techniques. Many such further processing techniques relate to elevated temperatures, particularly vacuum deposition, and in view of its excellent thermal stability, the release coating is very suitable for this technology. However, according to the final use of the release coating, the release coating can use such further processing.

[0162] The coated substrate can be used in a variety of end-use applications. For example, the coated substrate can be used in coating applications, packaging applications, adhesive applications, fiber applications, fabric or textile applications, construction applications, transportation applications, electronic device applications, or electrical applications. However, the composition can be used in end-use applications other than preparing the coated substrate, for example, in the preparation of articles such as silicone rubber.

[0163] Alternatively, the coated substrate can be used as a release liner, such as for tapes or adhesives, including any pressure sensitive adhesive, including acrylic, rubber, and silicone pressure sensitive adhesives, as well as acrylic, synthetic rubber, silicone, epoxy, and polyurethane adhesives. For double-sided tapes or adhesives, each major surface of the substrate can have a release coating disposed thereon.

[0164] Alternatively, when formulating the composition to prepare a release coating, the composition can be prepared by mixing the components together, such as preparing a one-part composition. However, it may be desirable to prepare the composition as a multi-part composition, wherein the component having a SiH functional group (e.g., (B) an organosilicon compound) and (C) a hydrosilylation reaction catalyst are stored as separate parts until the parts are combined at the time of use (e.g., just before application to a substrate).

[0165] For example, the multi-part curable composition may comprise:

[0166] a portion (A) which is a base portion comprising: (A) an organopolysiloxane comprising an average of at least two silicon-bonded ethylenically unsaturated groups per molecule, and (C) a hydrosilylation reaction catalyst, and optionally, when present, one or more of optional components (E) to (H); and

[0167] Part (B), which is a curing agent part comprising: (B) an organosilicon compound having an average of at least two silicon-bonded hydrogen atoms per molecule, and optionally, when present, one or more of optional components (E) to (H). Part (A) and part (B) may be provided in the form of a kit with instructions, for example, how to combine the parts to prepare the composition, how to apply the composition to a substrate, and how to cure the composition.

[0168] As described above, the composition may be applied to the substrate, for example, by any convenient means such as spraying, knife coating, dipping, screen printing, or by a roll coater such as an offset web coater, kiss coater, or etched drum coater.

[0169] The compositions of the present invention may be applied to any substrate, such as those described above. Alternatively, the compositions may be applied to polymer film substrates, such as polyester, particularly polyethylene terephthalate (PET), polyethylene, polypropylene or polystyrene films. Alternatively, the compositions may be applied to paper stock, including plastic coated paper (e.g., paper coated with polyethylene), glassine, super calender paper or clay coated kraft paper. Alternatively, the compositions may be applied to metal foil substrates, such as aluminum foil.

[0170] In certain embodiments, the method for preparing a coated substrate may also include treating the substrate before the composition is applied or arranged on the substrate. The substrate may be treated by any convenient means, such as plasma treatment or corona discharge treatment. Alternatively, the substrate may be treated by applying a primer. In some cases, if the substrate is treated before the release coating is formed on the substrate by the composition, the fixation of the release coating may be improved.

[0171] When the composition comprises (H) a vehicle, the method may further comprise: removing the (H) vehicle, which may be performed by any conventional means, such as heating at 50° C. to 100° C. for a time sufficient to remove all or a portion of the (H) vehicle. The method may further comprise curing the composition to form a release coating on the surface of the substrate. Curing may be performed by any conventional means, such as heating at 100° C. to 200° C.

[0172] Under production coater conditions, curing can be achieved at an air temperature of 120° C. to 150° C. with a residence time of 1 to 6 seconds, alternatively 1.5 to 3 seconds. Heating can be carried out in an oven (e.g., an air circulation oven or a tunnel oven) or by passing the substrate (including the wet deposit disposed thereon) around a heated drum.

[0173] The following examples are intended to illustrate the present invention and should not be viewed in any way as limiting the scope of the present invention.

[0174] Certain components utilized in the examples are listed in Table 1 below.

[0175] Table 1: Components / compounds used

[0176]

[0177]

[0178] General Procedure 1: Examples 1-4 and Comparative Examples 1-4

[0179] Examples 1-4 and Comparative Examples 1-4 Compositions for preparing release coatings were prepared according to General Procedure 1. The specific amount of each component used in the compositions of Examples 1-4 and Comparative Examples 1-4 is detailed in Tables 2 and 3 below.

[0180] In General Procedure 1, all components of each of Examples 1-4 and Comparative Examples 1-4, except the catalyst blend of the present invention or the conventional catalyst blend (as the case may be), are mixed for 1 minute via a dental mixer at 3500 revolutions per minute (rpm) to obtain a mixture. Then, the catalyst blend of the present invention or the conventional catalyst blend (as the case may be) is placed in the mixture to obtain a composition, and the composition is mixed for 1 minute via a dental mixer at 3500 rpm. In all compositions of Examples 1-4 and Comparative Examples 1-4, the content of platinum is the same, 93 ppm, and the total ratio of silicon-bonded hydrogen atoms to silicon-bonded vinyl groups is the same, 2 / 1 mol / mol (SiH to SiVi). In Table 3, CE represents a comparative example. In these embodiments, the platinum or metal content refers to the platinum or metal itself, rather than any ligand present in the complex.

[0181] Table 2: Examples 1-4

[0182] Components Example 1 Example 2 Example 3 Example 4 Base composition 2 (g) 32.54 32.54 21.83 24.85 (B1)(g) 4.02 4.02 5.35 0 (B2)(g) 0 0 0 2.49 Inhibitor (g) 0 0.004 0.004 0 Catalyst blend of the present invention (g) 3.46 3.46 3.46 2.60 Anti-sticking modifier (g) 0 0 9.36 0 Inhibitor / Pt molar ratio 0 1.68 9.56 0

[0183] Table 3: Comparative Examples 1-4

[0184] Components Comparative Example 1 Comparative Example 2 Comparative Example 3 Comparative Example 4 Base composition 1 (g) 32.54 0 0 0 Base composition 2 (g) 0 32.54 32.54 24.90 (B1)(g) 4.02 4.02 4.02 0 (B2)(g) 0 0 0 2.49 Inhibitor (g) 0 0.004 0 0 Conventional catalyst blend (g) 3.46 3.46 3.46 2.60 Inhibitor / Pt molar ratio 12.78 1.68 0 0

[0185] The soaking life of the composition of embodiment 1-4 and comparative example 1-4 was analyzed. Compositions for release coatings are usually formulated into soaking baths, and it is expected to extend the soaking life to the maximum extent to prevent the composition from prematurely curing during work. The soaking life can be extended by conventional means, such as by incorporating inhibitors into the composition, but such conventional means also inhibit curing at the same time. However, although it is expected to extend the soaking life to the maximum extent, it is also expected to shorten the curing time and reduce the curing temperature of the composition as much as possible, as described below. Generally, it is difficult to extend the soaking life while providing the desired (low) curing temperature and the associated shorter curing time.

[0186] Overall Soak Life Test: Each composition was tested continuously on a Brookfield DV2TLV viscometer at a specified temperature (23°C or 40°C). The overall soak life is the time it takes for the viscosity of the composition to double at a specified temperature. The longer the overall soak life, the better the coating performance.

[0187] Film soak life: Each composition was applied to a 2 mil thick polyethylene terephthalate (PET) film by a 2 mil Bird Bar on a flat platform to obtain a wet coating on the PET film. The film soak life is the time required for the wet coating to gel at room temperature. The gelation was measured by the finger test method, and the wet coating on the PET film was checked every 1 minute for the first 5 minutes and every 5 minutes thereafter. The time required for the wet coating to change from a smear (where the wet coating is completely liquid and can self-level after a finger is passed) to a smudge (where the wet coating cannot self-level after a finger is passed) or to cure (where the wet coating becomes completely solid) is reported as the film soak life. The longer the film soak life, the better the coating performance is indicated.

[0188] Tables 4 and 5 show the overall soak life and film soak life of the compositions of Examples 1 to 4 and Comparative Examples 1 to 4. In Table 5, TSTT stands for "Too Short to Test", which means that the overall soak life or film soak life is < 1 minute, which is particularly undesirable and completely unacceptable in industrial liner production processes due to the adverse effects of gelation on the coater and coater roller.

[0189] Table 4: Soak life of the compositions of Examples 1-4

[0190] test: Example 1 Example 2 Example 3 Embodiment 4) Film immersion life (minutes) 236 240 >240 NA Overall immersion life at 40°C (minutes) 28 98 395 13 Overall immersion life at 23°C (minutes) 152 731 NA 48

[0191] Table 5: Soaking life of the compositions of Comparative Examples 1-4

[0192]

[0193]

[0194] As shown in the above examples, when the compositions based on the conventional catalyst blend and the catalyst have the same inhibitor / Pt molar ratio, for example in Example 2 and Comparative Example 2, the catalyst provides Example 2 with a thin film soak life of 240 minutes, and a 40°C / 23°C overall soak life of 98 / 731 minutes. In contrast, the conventional catalyst blend provides Comparative Example 2 with a thin film soak life and an overall soak life at 40°C / 23°C that are too short to be tested. Although Comparative Example 1 has a testable thin film soak life and overall soak life, the inhibitor / Pt molar ratio of Comparative Example 1 is more than 700% higher than that of Comparative Example 2, and no inhibitor is required in the composition including the catalyst (e.g., as in Examples 1 and 4).

[0195] Coated substrates were prepared using the compositions of Examples 2 and 3 and Comparative Example 1. Physical properties were measured as described below.

[0196] Curing performance: extractable percentage

[0197] The curing properties of the specific compositions were evaluated by measuring the extractable percentage value (extractable %). Specifically, in order to measure the extractable %, each composition was coated and cured on a substrate (glass paper) to form a coated substrate, which was immediately cut into three sample trays (die cutter, 1.375 inches (3.49 cm)), only with tweezers, to minimize contamination and / or damage. The coated substrate includes a release coating formed by curing each composition on the substrate. Each sample tray was analyzed by X-ray fluorescence (XRF) to measure the initial coating weight (W i s ), which were then placed in individual bottles (100 mL, covered with lids) containing solvent (methyl isobutyl ketone, 40 mL) and left to soak on the bench for 30 minutes. XRF was performed on a Rigaku NEX QC+QC1499 XRF analyzer. Each sample disc was then removed from the bottle, placed with the coated side up on a clean surface (tissue paper) to allow residual solvent to evaporate (not blotted / wiped), and analyzed via XRF to determine the final coating weight (W f s The extractable % for each release coating is the percent change in coating weight from solvent immersion, i.e., calculated using the following formula: [(W i s -W f s ) / Wi]×100%. The extractable % represents the amount of uncured components of the composition (e.g., uncrosslinked silicone) that can be extracted from the release coating of the coated substrate. The lower the extractable % is, the higher / better the curing performance is indicated.

[0198] Curing performance: fixation (ROR%)

[0199] The fixation of a particular composition was evaluated by the Fixation Index, i.e., by determining the rub resistance percentage (ROR%) value. Specifically, each composition was coated and cured on a substrate (glass paper) to form a coated substrate. Immediately after curing, the coated substrate was cut into two sample discs (die cutter, 1.375 inches (3.49 cm)), and each sample disc was analyzed by XRF to determine the initial coating weight (W i a Each sample disk was then felt abraded under load (1.9 kg) using an automated abrasion device in a manner similar to a Taber-type abrasion test (e.g., such as ASTM D4060-19, "Standard Test Method for Abrasion Resistance of Organic Coatings by the Taber Abraser") and subsequently analyzed via XRF to determine the final coating weight (W f a ). The ROR% for each sample was calculated using the following formula: [W f s / W i s ]×100%. ROR% indicates how strongly a particular release coating is fixed to a substrate, such that a higher ROR% indicates higher / better fixation. ROR% was also measured after aging each coated substrate for one month at room temperature (RT).

[0200] Table 6 below shows the extractable %, ROR % and 1 month RT aging ROR % of the release coatings formed with the compositions of Comparative Example 1 and Examples 2 and 3. In column 1, the curing conditions involve oven temperature (180°C or 160°C) and dwell time (6 seconds or 3 seconds).

[0201] Table 6: Curing properties

[0202]

[0203] In addition to extractable % and ROR%, the release force of the release coating formed by the composition of Comparative Example 1 and Example 2 and Example 3 was also measured. The coated substrate was laminated with Tesa 7475 tape and aged for 7 days and 1 month under 40lb weight, at room temperature and 50% RH. Then at various speeds, i.e., 0.3m / min (MPM), 10m / min (MPM), 100m / min (MPM) and 300m / min (MPM), the coated substrate was peeled off from the tape under 180 degree peeling. The release force was measured via Imass SP-2100 and ZPE-1100W release test systems. The release force of the release coating cured under different curing conditions was measured. The curing conditions involved oven temperature (180°C or 160°C) and dwell time (6 seconds or 3 seconds). The values ​​of the 7-day aging release force and the 1-month aging release force are listed in Tables 7 to 10 below.

[0204] Table 7: 7-day aging release

[0205]

[0206] Table 8: 7-day aging release

[0207]

[0208] Table 9: Release force after 1 month aging

[0209]

[0210] Table 10: Release force after aging for 1 month

[0211]

[0212] Example 5 and Comparative Example 5

[0213] Example 5 and Comparative Example 5 Compositions for preparing release coatings were prepared. The specific amount of each component used in the compositions of Example 5 and Comparative Example 5 is detailed in Table 11 below.

[0214] Table 11: Example 5 and Comparative Example 5

[0215] Components: Example 5 Comparative Example 5 Base composition 3 (g) 88.268 88.268 Conventional catalyst blend (g) 0 8.596 Catalyst blend of the present invention (g) 8.596 0 (B2)(g) 6.0013 6.0013

[0216] In order to prepare the composition of Example 5 and Comparative Example 5, the base composition 3 and the conventional or catalyst blend of the present invention (as the case may be) are combined and mixed to obtain a mixture. Each mixture is placed in a capped vial and aged at room temperature in air. The color change of each mixture over time is monitored. Then, the organosilicon compound (B2) is added to each mixture to obtain a composition, and the composition is mixed on a dental mixer at 3500RPM for 30 seconds. Each composition is then analyzed by differential scanning calorimetry (DSC), and the appearance that changes over time is visually inspected. DSC is measured by heating each composition from 40°C to 200°C under N2 via TA DSC-2500DSC. In each composition, the content of platinum is the same, 93ppm, and the total ratio of silicon-bonded hydrogen atoms to silicon-bonded vinyl groups is the same, 2 / 1mol / mol (SiH to SiVi). Tables 12 and 13 below respectively describe the DSC data of the compositions of Example 5 and Comparative Example 5 at each time interval. In Tables 12 and 13, the appearance is based on visual inspection, and the appearance of the mixture not including the organosilicon compound (B2) and the composition including the organosilicon compound (B2) are reported.

[0217] Table 12: Example 5

[0218]

[0219] Table 13: Comparative Example 5

[0220]

[0221] As shown in Table 13, the combination of the conventional catalyst blend and the inhibitor causes the composition of Comparative Example 5 to undergo undesirable precipitation and color change over time, which is undesirable and problematic in the entire release coating industry. Similarly, as shown in Table 13, when the composition of Comparative Example 5 including the conventional catalyst blend and the inhibitor is aged, the curing performance becomes increasingly poor, T 峰值 、T 95 The viscosity doubling time at 100°C and 80°C increased dramatically over time. In addition, for the composition of Comparative Example 5, color change and precipitation also increased over time. In contrast, the catalyst of the present invention does not have compatibility issues with the inhibitor, as demonstrated by the composition of Example 5, which has no change in curing performance over time (T 峰值 、T 95 The viscosity doubling time at 100° C. and 80° C. remained almost unchanged). In addition, no color change or precipitation was observed in Example 5.

[0222] The present invention has been described by way of example, and it should be understood that the terms used are intended to be descriptive rather than restrictive. Obviously, many modifications and variations of the present invention are possible according to the above teachings. The present invention may be implemented in other ways beyond the specific description.

Claims

1. A composition for preparing a non-stick coating, the composition comprising: (A) an organopolysiloxane comprising at least one RSiO 3 / 2 Siloxy unit or at least one SiO 4 / 2 Siloxy units, wherein R is a substituted or unsubstituted hydrocarbon group, and the (A) organopolysiloxane has an average of at least two silicon-bonded ethylenically unsaturated groups per molecule; (B) an organosilicon compound having an average of at least two silicon-bonded hydrogen atoms per molecule; (C) a hydrosilylation catalyst, the hydrosilylation catalyst comprising a compound having the formula ML x D y A metal-ligand complex of , wherein M is a metal; x is equal to the oxidation state of M; each D is independently a neutral coordinating ligand; y is 0 or an integer from 1 to 4; and Each L is independently a monoanionic ligand having the formula: Each R 1 and R 2 is independently a halide or a substituted or unsubstituted group, wherein the substituted or unsubstituted group is selected from C1-C6 alkyl, C3-C8 cycloalkyl, C3-C8 heterocycloalkyl, C6-C 10 Alkyl aryl, C1-C6 alkoxy, C6-C 10 Aryl, C6-C 10 Heteroaryl, silyl, C2-C8 alkenyl, C2-C8 alkynyl, C1-C6 hydroxyl, C3-C 10 Arylene, C3-C 10 Heteroarylene, C2-C 10 Alkenylene, C3-C 10 Cycloalkenylene and C2-C 10 Alkynylidene, Where R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 Each of the above is independently selected from hydrogen, halide or a substituted or unsubstituted group selected from C1-C6 alkyl, C3-C8 cycloalkyl, C3-C8 heterocycloalkyl, C6-C 10 Alkyl aryl, C1-C6 alkoxy, C6-C 10 Aryl, C6-C 10 Heteroaryl, silyl, C2-C8 alkenyl, C2-C 10 Alkynyl, C1-C6 hydroxyl, C3-C 10 Arylene, C3-C 10 Heteroarylene, C2-C 10 Alkenylene, C3-C 10 Cycloalkenylene and C2-C 10 an alkynylene group; and Wherein E is C or Si.

2. The composition according to claim 1, wherein In the metal-ligand complex of the component (C): (i) M is a platinum group metal selected from Ru, Rh, Pd, Os, Ir and Pt; (ii) E is Si; (iii) R 1 and R 2 is an independently selected alkyl group; (iv) R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 each of which is hydrogen; or any combination of (v)(i) to (iv).

3. The composition according to claim 1 or 2, wherein: (i) each D is independently 1,5-cyclooctadiene, bicyclo[2.2.1]hept-2,5-diene, 1,5-hexadiene, ethylene, dibenzo[a,e]cyclooctene, N,N,N',N'-tetramethylethylenediamine, cyclooctatriene, norbornadiene or cyclooctene; (ii) the composition does not contain an organic solvent; or (iii) both (i) and (ii).

4. A composition according to any preceding claim, wherein the metal-ligand complex of component (C) has one of the following formulae: wherein each n is independently 0 to 2.

5. A composition according to any preceding claim, wherein the (A) organopolysiloxane has the formula (R3SiO 1 / 2 ) x (R2SiO 2 / 2 ) z (SiO 4 / 2 ), wherein each R is independently a substituted or unsubstituted hydrocarbyl group, provided that at least two of the R are independently selected ethylenically unsaturated groups, subscript x is from 0.05 to 4; subscript z is from 1 to 3,000.

6. The composition according to any one of the preceding claims, wherein the (B) organosilicon compound has the formula: H y' R 10 3-y' Si-(OSiR 10 2) m -(OSiR 10 H) m' -OSiR 10 3-y' H y' , where each R 10 is an independently selected hydrocarbyl group without aliphatic unsaturation, each y' is independently selected from 0 or 1, the subscripts m and m' are each independently from 0 to 1,000, provided that m and m' are not both 0 and m + m' is from 1 to 1,000; or wherein the (B) organosilicon compound has the formula: [(HR 10 SiO 2 / 2 ) a (-R 10 SiO 3 / 2 ) b c [(R 10 2SiO 2 / 2 ) w d , where each R 10 is independently selected and as defined above, the subscript a is from 0 to 10; the subscript b is from 1 to 4, provided that (a + b) = 3 to 12; 0 < c < 100; 2 ≤ w ≤ 2000; and 0 < d < 100, provided that c > d.​​ 7. A composition according to any preceding claim, wherein: (i) the (B) organosilicon compound comprises an organohydrogensiloxane having an average of at least two pendant silicon-bonded hydrogen atoms per molecule; (ii) the molar ratio of SiH to silicon-bonded ethylenically unsaturated groups in components (A) and (B) is from 1:1 to 5:1; or (iii) both (i) and (ii).

8. A composition according to any preceding claim, which has a soak life at 40°C of at least 20 minutes when components (A) to (C) are combined in the absence of any inhibitor.

9. The composition according to any one of claims 1 to 7, further comprising at least one of (D) an inhibitor, (E) an anchor additive, (F) an anti-fog additive, and / or (G) an anti-stick modifier.

10. A method of preparing a composition according to any preceding claim, comprising combining the (A) organopolysiloxane, the (B) organopolysiloxane and the (C) hydrosilylation catalyst to obtain the composition. 11 . The method according to claim 10 , further comprising preparing the (C) hydrosilylation catalyst.

12. A method of forming a coated substrate, the method comprising: applying the composition to a substrate; as well as curing the composition to provide a release coating on the substrate, thereby forming the coated substrate; The composition is according to any one of claims 1 to 9.

13. The method of claim 12, wherein the substrate comprises cellulose and / or a polymer.

14. A coated substrate comprising a release coating disposed on a substrate formed according to the method of claim 12 or 13.

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