Compositions and methods for preparing hydrosilylation reaction products

Abstract

The composition comprises an unsaturated compound (A) containing at least one aliphatic unsaturated group per molecule, wherein the unsaturated compound (A) also contains at least one silicon-bonded hydrogen atom per molecule, and / or the composition further comprises a silicon hydride compound (B) containing at least one silicon-bonded hydrogen atom per molecule. The composition further comprises a catalyst (C). The catalyst (C) has the formula X2Pt(II)Y2 (wherein each X is the same and selected from a fluorinated acetate group or a halide, and each Y is independently selected from a substituted or unsubstituted pyridine group, provided that if each Y is substituted, it is not linked to other Ys).

Description

[Technical Field]

[0001] (Cross-reference of related applications) This application claims priority and all interests of U.S. Patent Application No. 63 / 456,859 filed on April 4, 2023, U.S. Patent Application No. 63 / 465,554 filed on May 11, 2023, and U.S. Patent Application No. 63 / 616,661 filed on December 31, 2023, the contents of which are incorporated herein by reference in their entirety.

[0002] (Field of Invention) This disclosure relates in general to compositions, and more specifically to compositions comprising certain catalysts capable of undergoing hydrosilylation reactions and possessing excellent properties. This disclosure also relates to related methods. [Background technology]

[0003] Hydrosilylation reactions are generally known in the art and involve addition reactions between silicon-bonded hydrogen and aliphatic unsaturated compounds. Hydrosilylation reactions are used in a variety of applications. For example, curable compositions often rely on hydrosilylation reactions to cure or crosslink their components to obtain cured products. Furthermore, hydrosilylation reactions can be used to prepare individual components or compounds, such as components to be included in curable compositions.

[0004] Hydrosilylation reactions are typically carried out in the presence of a platinum metal catalyst due to its excellent catalytic activity. Alternatively, metal complexes can be used to catalyze hydrosilylation reactions.

[0005] It is often desirable to selectively control the catalytic activity of a catalyst, particularly to extend the shelf life and improve the stability of curable compositions without the need to utilize two-component or multi-component systems. For example, many conventional catalysts initiate hydrosilylation reactions under ambient conditions, including room temperature. Numerous attempts have been made to selectively control the catalytic activity of a catalyst, for example, by including a hydrosilylation inhibitor with the catalyst, or by encapsulating the catalyst in a polymer that melts at high temperatures. However, conventional techniques for selectively controlling the catalytic activity of a catalyst have drawbacks. For example, incomplete encapsulation reduces shelf life and stability. Furthermore, while encapsulated catalysts can prevent premature reactions under ambient conditions, conventional encapsulated catalysts require washing to remove residual catalyst. For example, residual catalyst remains on the external surface of conventional encapsulated catalysts, which must be removed to prevent premature reactions, adding processing steps and costs. Moreover, encapsulation adds processing steps and costs to catalyst preparation. [Overview of the project]

[0006] This disclosure provides compositions. The compositions include an unsaturated compound (A) containing at least one aliphatic unsaturated group per molecule, wherein the unsaturated compound (A) also contains at least one silicon-bonded hydrogen atom per molecule, and / or the composition further comprises a silicon hydride compound (B) containing at least one silicon-bonded hydrogen atom per molecule. The compositions further comprise a catalyst (C). The catalyst (C) has the formula X2Pt(II)Y2 (wherein each X is the same and selected from a fluorinated acetate group or a halide, and each Y is independently selected from a substituted or unsubstituted pyridine group, provided that if each Y is substituted, it is not linked to other Ys).

[0007] A method for preparing hydrosilylation reaction products is also provided. This method involves reacting an aliphatic unsaturated group with a silicon-bonded hydrogen atom in the presence of a catalyst (C) to obtain a hydrosilylation reaction product. The aliphatic unsaturated group is present in the unsaturated compound (A), and the composition follows the same conditions described above. [Modes for carrying out the invention]

[0008] A composition is disclosed. The composition comprises (A) an unsaturated compound. The unsaturated compound (A) contains at least one aliphatic unsaturated group per molecule, which may also be alternatively called ethylenically unsaturated. The unsaturated compound (A) is not limited and may be any unsaturated compound having at least one aliphatic unsaturated group. In certain embodiments, the unsaturated compound (A) constitutes an organic compound. In other embodiments, the unsaturated compound (A) constitutes a siloxane. In yet another embodiment, the unsaturated compound (A) constitutes a silicone-organic hybrid or an organosilicon compound. Various embodiments and examples of the unsaturated compound (A) are disclosed below.

[0009] In certain embodiments, the unsaturated compound (A) contains, on average, at least two aliphatic unsaturated groups per molecule. In such embodiments, the unsaturated compound (A) can undergo polymerization or curing beyond hydrosilylation of a single curing site. The aliphatic unsaturated groups of the unsaturated compound (A) may be located at the terminal, pendant, or both positions of the unsaturated compound (A).

[0010] For example, an aliphatic unsaturated group may be an alkenyl group and / or an alkynyl group. An "alkenyl group" means an acyclic, branched or unbranched monovalent hydrocarbon group having one or more carbon-carbon double bonds. An alkenyl group may have 2 to 30 carbon atoms, or 2 to 24 carbon atoms, or 2 to 20 carbon atoms, or 2 to 12 carbon atoms, or 2 to 10 carbon atoms, or 2 to 6 carbon atoms. Examples of alkenyl groups include, but are not limited to, vinyl, allyl, propenyl, and hexenyl. An "alkynyl group" means an acyclic, branched or unbranched monovalent hydrocarbon group having one or more carbon-carbon triple bonds. An alkynyl group may have 2 to 30 carbon atoms, or 2 to 24 carbon atoms, or 2 to 20 carbon atoms, or 2 to 12 carbon atoms, or 2 to 10 carbon atoms, or 2 to 6 carbon atoms. Examples of alkynyls include, but are not limited to, ethynyl, propynyl, and butynyl.

[0011] In certain embodiments, the unsaturated compound (A) is of formula R 1 -ZR 1 (wherein Z is a divalent linking group which may be a divalent hydrocarbon, polyoxyalkylene, polyalkylene, polyisoalkylene, hydrocarbon-silicone copolymer, siloxane, or a mixture thereof (in block or randomized form)). Z may be linear or branched. In these particular embodiments, R 1 These are independently selected and include aliphatic unsaturated compounds, i.e., each R 1 These are independently selected from alkenyl and alkynyl groups. However, the aliphatic unsaturated group does not need to be terminal in the unsaturated compound (A).

[0012] In these specific embodiments, the unsaturated compound (A) is R 1 It contains two aliphatic unsaturated groups represented by .

[0013] In one embodiment of the unsaturated compound (A), Z is a divalent hydrocarbon. The divalent hydrocarbon Z may contain 1 to 30 carbon atoms as either an aliphatic or aromatic structure, and may be branched or unbranched. Alternatively, the linking group Z may be an alkylene group containing 1 to 12 carbon atoms. In these embodiments, the unsaturated compound (A) may be selected from α,ω-unsaturated hydrocarbons. Alternatively, α,ω-unsaturated hydrocarbons may be called olefins.

[0014] For example, the unsaturated compound (A) may be any diene, diyne, or en-yne compound. Referring to the formula above, in these embodiments, R 1 These can be independently selected from, for example, CH2=CH-, CH2=CHCH2-, CH2=CH(CH2)4-, CH2=C(CH3)CH2-, or similar substituted unsaturated groups such as H2C=C(CH3)- and HC=C(CH3)-. In such embodiments, the unsaturated compound (A) may be called an α,ω-unsaturated hydrocarbon. An α,ω-unsaturated hydrocarbon is, for example, one of the groups with the formula CH2=CH(CH2) b The α,ω-diene of CH=CH2, formula

[0015] [ka] α,ω-diyne, formula

[0016] [ka] The formula may be α,ω-ene-yne, or a mixture thereof, where b is independently 0 to 20 or 1 to 20.

[0017] Specific examples of suitable diene, diyne or en-yne compounds include 1,4-pentadiene, 1,5-hexadiene, 1,6-heptadiene, 1,7-octadiene, 1,8-nonadiene, 1,9-decadiene, 1,11-dodecadiene, 1,13-tetradecadiene, and 1,19-eicosadiene, 1,3-butadiyne, 1,5-hexadiyne (dipropargyl), and 1-hexene-5-yne.

[0018] However, the unsaturated compound (A) may alternatively have the formula R 1 -Z' (wherein R 1 is as defined above and Z' is a monovalent hydrocarbon group (or a silyl or siloxane group)). In these specific embodiments, the unsaturated compound (A) contains one aliphatic unsaturated group represented by R 1 .

[0019] When the unsaturated compound (A) contains only one aliphatic unsaturated group, the unsaturated compound (A) may be referred to as an unsaturated hydrocarbon and can be any -ene or -yne compound. In such embodiments, the unsaturated compound (A) can be an acyclic alkene and / or an acyclic alkyne. However, the unsaturated compound (A) can contain an aryl group as long as the unsaturated compound (A) also contains at least one aliphatic unsaturated group independent of any aryl group, for example, pendant from any aryl group.

[0020] In another embodiment, the unsaturated compound (A) contains a polyether or is a polyether. In these embodiments, the unsaturated compound (A) contains a polyoxyalkylene group having the formula (C a H 2a O), wherein a is from 2 to 4. Referring to the general formula above, Z' is a polyoxyalkylene group. In these embodiments, the unsaturated compound (A) can be referred to as a polyoxyalkylene.

[0021] Polyoxyalkylene may contain oxyethylene units (C2H4O), oxypropylene units (C3H6O), oxybutylene or oxytetramethylene units (C4H8O), or mixtures thereof, which may be in block form or random in the unsaturated compound (A).

[0022] For example, the unsaturated compound (A) as a polyoxyalkylene has the following general formula: R 1 O-[(C2H4O) c (C3H6O) d (C4H8O) e ]-R 1 (In the formula, each R 1 d and e are independently selected and defined above, and may have c between 0 and 200, d between 0 and 200, and e between 0 and 200, provided that c, d, and e are not all 0 at the same time. In certain embodiments, c is between 0 and 50, or 0 and 10, or 0 and 2. In these or other embodiments, d is between 0 and 100, or 1 and 100, or 5 and 50. In these or other embodiments, e is between 0 and 100, or 0 and 50, or 0 and 30. In various embodiments, the ratio of (d+e) / (c+d+e) is greater than 0.5, or greater than 0.8, or greater than 0.95.

[0023] This polyoxyalkylene is independently selected at each molecular chain terminus (i.e., the alpha and omega positions) and defined above as R 1 It terminates at R. 1 Further examples include H2C=C(CH3)CH2-H2C=CHCH2CH2-, H2C=CHCH2CH2CH2-, PH2C=CHCH2CH2CH2CH2-,

[0024] [ka] These are some examples. However, the above polyoxyalkylenes are merely examples of suitable polyoxyalkylenes.

[0025] In certain embodiments, the polyoxyalkylene group contains only oxypropylene units (C3H6O). A typical non-limiting example of a polyoxyalkylene containing polyoxypropylene is H2C=CHCH2[C3H6O] d CH2CH=CH2, H2C=CH[C3H6O] d CH=CH2, H2C=C(CH3)CH2[C3H6O] d CH2C(CH3)=CH2,

[0026] [ka] These are listed, and in the formula, d is as defined above.

[0027] A typical non-limiting example of a polyoxyalkylene containing polyoxybutylene or poly(oxytetramethylene) is H2C=CHCH2[C4H8O] e CH2CH=CH2, H2C=CH[C4H8O] e CH=CH2, H2C=C(CH3)CH2[C4H8O] e CH2C(CH3)=CH2,

[0028] [ka] These are listed, and in the formula, e is as defined above.

[0029] Examples of polyoxyalkylenes suitable for (A) unsaturated compounds include two aliphatic unsaturated groups. However, polyoxyalkylenes suitable for (A) unsaturated compounds may include only one aliphatic unsaturated group. For example, a polyoxyalkylene suitable for (A) unsaturated compounds may alternatively have the following general formula: R 1 O-[(C2H4O) c (C3H6O) d (C4H8O) e ]-R 2 (In the formula, R 1 c, d, and e are defined above, R 2 The group may have H, or an alkyl group having 1 to 10 carbon atoms, for example, CH3. Furthermore, any of the above descriptions or examples also apply to this embodiment. Those skilled in the art will readily understand how the above example of a polyoxyalkylene having two aliphatic unsaturated groups may instead contain only one aliphatic unsaturated group.

[0030] Polyoxyalkylenes can be prepared, for example, by polymerization of ethylene oxide, propylene oxide, butylene oxide, 1,2-epoxyhexane, 1,2-epoxyoctance, and / or cyclic epoxides such as cyclohexene oxide or exo-2,3-epoxynorborane. The polyoxyalkylene portion of a polyoxyalkylene may contain oxyethylene units (C2H4O), oxypropylene units (C3H6O), oxybutylene units (C4H8O), or mixtures thereof. Typically, a polyoxyalkylene group is defined on a molar basis and contains a majority of oxypropylene or oxybutylene units, as indicated by the subscripts c, d, and e in the above formulas.

[0031] In another embodiment, the general formula R of the unsaturated compound (A) 1 -ZR 1 Z or formula R 1 The Z' in -Z' represents a polyalkylene group. A polyalkylene group may contain C2-C6 alkylene units or their isomers. One specific example is the polyisobutylene group, which is a polymer containing isobutylene units. For example, unsaturated compound (A) may be diallyl-terminated polyisobutylene or allyl-terminated polyisobutylene. The molecular weight of the polyisobutylene group can vary, but is typically in the range of 100-10,000 g / mol.

[0032] In certain embodiments, the unsaturated compound (A) comprises an organopolysiloxane. The organopolysiloxane is not limited and can be any organopolysiloxane containing at least one silicon-bonded aliphatic unsaturated group per molecule. For example, the organopolysiloxane can be linear, branched, partially branched, cyclic, resinous (i.e., having a three-dimensional network), or can contain a combination of different structures. When the unsaturated compound (A) contains an organopolysiloxane, the aliphatic unsaturated group is silicon-bonded (e.g., as a silicon-bonded alkenyl and / or silicon-bonded alkynyl).

[0033] In certain embodiments, when the unsaturated compound (A) contains an organopolysiloxane, the organopolysiloxane has the following average formula: R 3 f SiO (4-f) / 2 (where each R 3 is an independently selected substituted or unsubstituted hydrocarbyl group, provided that in each molecule, at least one, or at least two of the R 3 groups are aliphatic unsaturated groups, and f is selected such that 0 < f ≦ 3.2).

[0034] The average formula for the above organopolysiloxane is alternatively (R 3 3SiO 1 / 2 ) w (R 3 2SiO 2 / 2 ) x (R 3 SiO 3 / 2 ) y (SiO 4 / 2 ) z (where R 3The conditions are defined above, and can also be written as follows: w, x, y, and z are independently between 0 and 1, provided that w+x+y+z=1. Those skilled in the art will understand how such M, D, T, and Q units, and their mole fractions, affect the subscript f in the above average formula. The T and Q units, indicated by the subscripts y and z, are typically present in the silicone resin, while the D unit, indicated by the subscript x, is typically present in the silicone polymer (and may also be present in the silicone resin).

[0035] Each R 3 As described above, these are independently selected and can be linear, branched, cyclic, or a combination thereof. Generally, R 3Suitable hydrocarbyl groups can independently be linear, branched, cyclic, or combinations thereof. Cyclic hydrocarbyl groups include aryl groups and saturated or non-conjugated cyclic groups. Cyclic hydrocarbyl groups can independently be monocyclic or polycyclic. Linear and branched hydrocarbyl groups can independently be saturated or unsaturated. An example of a combination of linear and cyclic hydrocarbyl groups is the aralkyl group. General examples of hydrocarbyl groups include alkyl groups, aryl groups, alkenyl groups, halocarbon groups, and their derivatives, variants, 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 branched saturated hydrocarbon groups having 6 to 18 carbon atoms. Suitable non-conjugated cyclic groups include cyclobutyl, cyclohexyl, and cycyloheptyl. Suitable aryl groups include phenyl, tolyl, xylyl, naphthyl, benzyl, and dimethylphenyl. Suitable alkenyl groups include vinyl, allyl, propenyl, isopropenyl, butenyl, isobutenyl, pentenyl, heptenyl, hexenyl, hexadecenyl, octadecenyl, and cyclohexenyl. Suitable monovalent halogenated hydrocarbon groups (i.e., halocarbon or substituted hydrocarbon groups) include halogenated alkyl groups, aryl groups, and combinations thereof. Examples of halogenated alkyl groups include the alkyl groups described above in which one or more hydrogen atoms are replaced by halogen atoms such as F or Cl.Specific examples of alkyl halides include fluoromethyl, 2-fluoropropyl, 3,3,3-trifluoropropyl, 4,4,4-trifluorobutyl, 4,4,4,3,3-pentafluorobutyl, 5,5,5,4,4,3,3-heptafluoropentyl, 6,6,6,5,5,4,4,3,3-nonafluorohexyl, and 8,8,8,7,7-pentafluorooctyl, 2,2-difluorocyclopropyl, 2,3-difluorocyclobutyl, 3,4-difluorocyclohexyl, and 3,4-difluoro-5-methylcycloheptyl, chloromethyl, chloropropyl, 2-dichlorocyclopropyl, and 2,3-dichlorocyclopentyl groups, as well as their derivatives. Examples of aryl halides include the aryl groups described above, in which one or more hydrogen atoms are replaced by halogen atoms such as F or Cl. Specific examples of aryl halides include chlorobenzyl and fluorobenzyl groups.

[0036] In certain embodiments, the organopolysiloxane is substantially linear or linear. Substantially linear means that the organopolysiloxane may include at least some branches belonging to T or Q, typically T siloxy units, as long as at least 90 mol% or at least 95 mol% of the siloxy units are D siloxy units. In these embodiments, the substantially linear organopolysiloxane has the following average formula: R 3 f’ SiO (4-f’) / 2 (In the formula, each R 3 The conditions for this are defined above, and f' may have such that 1.9 ≤ f' ≤ 2.2.

[0037] In these embodiments, at a temperature of 25°C, the substantially linear organopolysiloxane is typically in the form of a fluid liquid or uncured rubber. Generally, the substantially linear organopolysiloxane has a viscosity of 10–30,000,000 mPa·s, or 10–10,000 mPa·s, or 100–1,000,000 mPa·s, or 100–100,000 mPa·s at 25°C. As is understood in the art, viscosity can be measured at 25°C via a Brookfield LV DV-E viscometer.

[0038] In certain embodiments where the organopolysiloxane is substantially linear or linear, the organopolysiloxane has the following average formula: (R 3 3SiO 1 / 2 ) m’ (R 3 2SiO 2 / 2 ) n’ (R 3 SiO 3 / 2 ) o , (In the formula, each R 3 These are independently selected and defined above (at least one R in each molecule) 3 The subscripts may have the following characteristics (including the condition that is an aliphatic unsaturated group), m'≧2, n'≧1, and o≧0. In certain embodiments, the subscript m' is 2-10, or 2-8, or 2-6. In these embodiments or other embodiments, the subscript n' is 1-1,000, or 1-500, or 1-200. In these embodiments or other embodiments, the subscript o is 0-10, or 0-5, or 0-2. As understood in the art, when the subscript o is 0, the organopolysiloxane is linear.

[0039] If an organopolysiloxane is substantially linear, or if it is linear, the silicon-bonded aliphatic unsaturated group can be located at the pendant, terminal, or both. A specific example of an organopolysiloxane having a pendanted silicon-bonded aliphatic unsaturated group is an organopolysiloxane with the average formula: (CH3)3SiO[(CH3)2SiO] n’ [(CH3)ViSiO] m’ Si(CH3)3 [wherein n' and m' are defined above, and Vi represents a vinyl group] may have this average formula. With respect to this average formula, it will be clear to those skilled in the art that, as long as there are at least two aliphatic unsaturated groups in one molecule, any methyl group may be replaced with vinyl or a substituted or unsubstituted hydrocarbyl group, and any vinyl group may be replaced with any ethylenically unsaturated group. Alternatively, as a specific example of an organopolysiloxane having terminal silicon-bonded aliphatic unsaturated groups, the organopolysiloxane has the average formula: Vi(CH3)2SiO[(CH3)2SiO] n’ Si(CH3)2Vi [wherein n' and Vi are defined above] may have the following: Dimethylpolysiloxanes with silicon-bonded vinyl group terminus can be used alone or in combination with the dimethyl,methyl-vinylpolysiloxanes disclosed above. With respect to this average formula, those skilled in the art will see that, as long as there are at least two aliphatic unsaturated groups in one molecule, any methyl group may be replaced with vinyl or a substituted or unsubstituted hydrocarbyl group, and any vinyl group may be replaced with any ethylenically unsaturated group. Since at least two silicon-bonded aliphatic unsaturated groups can be both pendant and terminal, (A) organopolysiloxane has the average formula: Vi(CH3)2SiO[(CH3)2SiO] n’ [(CH3)ViSiO] m’ SiVi(CH3)2 [wherein n', m', and Vi are defined above] may have the following:

[0040] Substantially linear organopolysiloxanes include dimethylpolysiloxane with dimethylvinylsiloxy groups sealed at both ends of the molecular chain, methylphenylpolysiloxane with dimethylvinylsiloxy groups sealed at both ends of the molecular chain, methylphenylsiloxane-dimethylsiloxane copolymer with dimethylvinylsiloxy groups sealed at both ends of the molecular chain, methylvinylsiloxane-methylphenylsiloxane copolymer with dimethylvinylsiloxy groups sealed at both ends of the molecular chain, and methylvinylsiloxane-diphenylsiloxane copolymer with dimethylvinylsiloxy groups sealed at both ends of the molecular chain. Examples include polymers, methylvinylsiloxane-methylphenylsiloxane-dimethylsiloxane copolymers with dimethylvinylsiloxy groups sealed at both ends of the molecular chain, methylvinylsiloxane-methylphenylsiloxane copolymers with trimethylsiloxy groups sealed at both ends of the molecular chain, methylvinylsiloxane-diphenylsiloxane copolymers with trimethylsiloxy groups sealed at both ends of the molecular chain, and methylvinylsiloxane-methylphenylsiloxane-dimethylsiloxane copolymers with trimethylsiloxy groups sealed at both ends of the molecular chain.

[0041] In these embodiments or other embodiments, (A) organopolysiloxane may be a resinous organopolysiloxane. In these embodiments, the resinous organopolysiloxane has an average formula: R 3 f’’ SiO (4-f’’) / 2 (In the formula, each R 3 The conditions for this are defined above, and f'' may have such that 0.5 ≤ f'' ≤ 1.7.

[0042] Resinous organopolysiloxanes have a branched or three-dimensional network molecular structure. At 25°C, resinous organopolysiloxanes may be in liquid or solid form, or optionally dispersed in a carrier, which can solubilize and / or disperse the resinous organopolysiloxane in the carrier.

[0043] In certain embodiments, resinous organopolysiloxanes can be exemplified by organopolysiloxanes containing only T units, organopolysiloxanes containing T units in combination with other siloxy units (e.g., M, D, and / or Q siloxy units), or organopolysiloxanes containing Q units in combination with other siloxy units (i.e., M, D, and / or T siloxy units). Resinous organopolysiloxanes contain T and / or Q units. Specific examples of resinous polyorganosiloxanes are vinyl-functionalized silsesquioxanes and vinyl-functionalized MQ resins.

[0044] Organopolysiloxanes may include combinations or mixtures of different organopolysiloxanes, such as organopolysiloxanes with different structures.

[0045] Alternatively, the unsaturated compound (A) may be a silicone-organic hybrid. For example, the unsaturated compound (A) may include a hydrosilylation reaction product of an organopolysiloxane (or one or more organopolysiloxanes and one or more organic compounds), in which case the main chain of the unsaturated compound (A) may contain a divalent organic linking group. As another example, the unsaturated compound (A) can be obtained by reacting an organohydrogensiloxane with another organopolysiloxane or organic compound.

[0046] For example, the unsaturated compound (A) may be a reaction product of (a1) at least one Si-H compound and (b1) at least one compound having ethylenically unsaturated properties. In these embodiments, the molar excess of ethylenically unsaturated groups in compound (b1) is utilized so that the unsaturated compound (A) contains at least one, or on average at least two, silicon-bonded aliphatic unsaturated groups compared to the Si-H groups in compound (a1).

[0047] The reaction product of (a1) a Si-H compound and (b1) an ethylenically unsaturated compound may be called an (AB)n-type copolymer, where (a1) the Si-H compound forms unit A and (b1) the ethylenically unsaturated compound forms unit B. Different combinations of (a1) Si-H compounds and different combinations of (b1) ethylenically unsaturated compounds may be used so that the resulting (b) crosslinking agent contains distinct units but cannot be an (AB)n-type copolymer. The distinct units may be randomized or in block form.

[0048] Alternatively, unsaturated compound (A) may constitute an organosilicon compound but not an organopolysiloxane. For example, unsaturated compound (A) may constitute a silane, disilane, or siloxane (e.g., disiloxane) but not an organopolysiloxane.

[0049] An example of a suitable silane is, formula R 4 z’’ SiR 5 4-z’’ (In the formula, each R 4 These are independently aliphatic unsaturated groups, and each R 5 The group is a silane (where 1 ≤ z'' ≤ 4) and is independently a substituted or unsubstituted hydrocarbyl group. An example of a siloxane is tetramethyldivinyldisiloxane. Those skilled in the art will understand how to prepare or obtain a compound for use as an unsaturated compound (A).

[0050] The unsaturated compound (A) may be a single unsaturated compound or a combination of two or more different silicon hydride compounds.

[0051] The composition and the unsaturated compound (A) comply with at least one of the following two conditions: (1) the unsaturated compound (A) also contains at least one silicon-bonded hydrogen atom per molecule, and / or (2) the composition further contains a silicon hydride compound (B) containing at least one silicon-bonded hydrogen atom per molecule.

[0052] In the first embodiment, condition (1) is true, and as a result, the unsaturated compound (A) also contains at least one silicon-bonded hydrogen atom per molecule. In the second embodiment, condition (2) is true, and as a result, the composition further contains a hydrogenated silicon compound containing at least one silicon-bonded hydrogen atom per molecule of (B). Finally, in the third embodiment, both condition (1) and condition (2) are true, and as a result, the unsaturated compound (A) contains at least one silicon-bonded hydrogen atom per molecule, and the composition further contains a hydrogenated silicon compound containing at least one silicon-bonded hydrogen atom per molecule.

[0053] In the first embodiment, condition (1) is true, and the unsaturated compound (A) contains at least one silicon-bonded hydrogen atom per molecule in addition to an aliphatic unsaturated group. In these embodiments, the unsaturated compound (A) can be any compound containing at least one silicon-bonded hydrogen atom and at least one aliphatic unsaturated group. In these embodiments, the unsaturated compound (A) is typically an organosilicon compound and / or an organopolysiloxane.

[0054] A person skilled in the art can easily understand the method for preparing or obtaining such an unsaturated compound. For example, an organosilicon compound containing both aliphatic unsaturated hydrogen and silicon-bonded hydrogen can be prepared from the unsaturated organic compounds disclosed above. As a mere example, the α,ω-diene of the formula CH2=CH(CH2) b CH=CH2 reacts with silane of the formula H2Si(CH3)2 in the presence of a hydrosilylation catalyst to obtain an unsaturated compound of the formula CH2=CH(CH2) b CH2CH2Si(CH3)2H containing one aliphatic unsaturated group and one silicon-bonded hydrogen atom. The organosilicon compound may also be a silane, disilane, siloxane, etc. For example, the organosilicon compound has the formula R 4 b’ H c’ SiR 5 4-b’-c’ (wherein R 4 and R 5which may be an organosilicon compound independently selected and defined above, where b’ is 1, 2, or 3, c’ is 1, 2, or 3, provided that 2 ≤ (b’ + c’) ≤ 4).

[0055] When the unsaturated compound (A) constitutes an organopolysiloxane having both aliphatic unsaturation and silicon-bonded hydrogen, the organopolysiloxane has the formula R 3 d’ H e’ SiO (4-d’-e’) / 2 (where R 3 is independently selected and defined above (still subject to the condition that at least one R 3 is an aliphatic unsaturated group), and e’ and f’ are each greater than 0 such that 0 < (d’ + e’) ≤ 3.2).

[0056] Alternatively, when the unsaturated compound (A) contains an organopolysiloxane having both aliphatic unsaturation and silicon-bonded hydrogen, the silicon-bonded aliphatic unsaturated groups and silicon-bonded hydrogen atoms may be present in any M, D, and / or T siloxy units present in the organopolysiloxane and may be bonded to the same silicon atom (in the case of M and / or D siloxy units). The organopolysiloxane may contain, for example, as M siloxy units, (R 3 3SiO 1 / 2 ), (R 3 2HSiO 1 / 2 ), (R 3 H2SiO 1 / 2 ), and / or (H3SiO 1 / 2 ). The organopolysiloxane may contain, for example, as D siloxy units, (R 3 2SiO 2 / 2 ), (R 3 HSiO 2 / 2 ), and / or (H2SiO 2 / 2 ). The organopolysiloxane may contain, for example, as T siloxy units, (R 3 SiO 3 / 2 ) and / or (HSiO 3 / 2 ). Such siloxy units may be combined in any manner, optionally together with Q siloxy units, R3 An organopolysiloxane can be obtained having at least one silicon-bonded aliphatic unsaturated group and at least one silicon-bonded hydrogen atom represented by .

[0057] For example, organopolysiloxanes are given by the following formula: (R 3 2HSiO 1 / 2 ) w’ (R 3 2SiO 2 / 2 ) x’ (R 3 SiO 3 / 2 ) y’ (SiO 4 / 2 ) z’ , (R 3 H2SiO 1 / 2 ) w’ (R 3 2SiO 2 / 2 ) x’ (R 3 SiO 3 / 2 ) y’ (SiO 4 / 2 ) z’ , (R 3 3SiO 1 / 2 ) w’ (R 3 HSiO 2 / 2 ) x’ (R 3 SiO 3 / 2 ) y’ (SiO 4 / 2 ) z’ , (R 3 H2SiO 1 / 2 ) w’ (R 3 HSiO 2 / 2 ) x’ (R 3 SiO 3 / 2 ) y’ (SiO 4 / 2 ) z’ , (R 3 3SiO 1 / 2 ) w’ (R 3 2SiO 2 / 2 ) x’ (HSiO 3 / 2 ) y’ (SiO 4 / 2 ) z’ , (R 3 3SiO1 / 2 ) w’ (R 3 HSiO 2 / 2 ) x’ (R 3 SiO 3 / 2 ) y’ (SiO 4 / 2 ) z’ , and / or (R 3 H2SiO 1 / 2 ) w’ (R 3 HSiO 2 / 2 ) x’ (HSiO 3 / 2 ) y’ (SiO 4 / 2 ) z’ etc (in the formula, each R 3 These are independently selected and defined above (at least one R 3 (where is an aliphatic unsaturated group), w', x', y', and z' can independently be any one of the following: 0 or greater and 1 or less, provided that w'+x'+y'+z''=1.

[0058] In the second embodiment, condition (2) is true, and the composition further comprises a silicon hydride compound (B) containing at least one silicon-bonded hydrogen atom per molecule. In these embodiments, the silicon hydride compound (B) may be any compound containing at least one silicon-bonded hydrogen atom. Depending on the structure of the silicon hydride compound (B), the silicon hydride compound (B) may be a silane compound, an organosilicon compound, an organohydrogensilane, an organohydrogensiloxane, and the like.

[0059] The silicon hydride compound (B) may be linear, branched, cyclic, resinous, or have a combination of such structures. In acyclic polysilanes and polysiloxanes, silicon-bonded hydrogen atoms may be located at the terminal, pendant, or both terminal and pendant positions. Cyclosilanes and cyclosiloxanes typically have 3 to 12 silicon atoms, or 3 to 10 silicon atoms, or 3 to 4 silicon atoms.

[0060] In a particular embodiment, silicon hydride compound (B) is of formula R 6 4-s SiH s (In the formula, R 6 R is a silicon hydride compound (where R is independently selected and can be any silicon bonding group, and s is selected such that 1 ≤ s ≤ 4). Typically, s is 1, 2, or 3, or 1 or 2. 6 Typically, these are independently substituted or unsubstituted hydrocarbyl groups, preferred examples of which are described above. However, R 6 R can be any silicon bonding group, as long as silicon hydride (B) can still undergo hydrosilylation via its silicon-bonded hydrogen atoms. For example, R 6 It may be a halogen. If silicon hydride(B) is a silane compound, silicon hydride(B) may be monosilane, disilane, trisilane, or polysilane.

[0061] In these embodiments or other embodiments, silicon hydride compound (B) is of formula H g’ R 7 3-g’ Si-R 8 -SiR 7 2H (in the formula, each R 7 is an independently selected substituted or unsubstituted hydrocarbyl group, g' is 0 or 1, and R 8 It may be an organosilicon compound of a divalent linking group. 8 This is a siloxane chain (e.g., -R 7 2SiO-, -R 7 The divalent hydrocarbon group may be HSiO- and / or -H2SiO- (containing a D-siloxy unit), or it may be a divalent hydrocarbon group. Typically, the divalent hydrocarbon group does not contain aliphatic unsaturated material. The divalent hydrocarbon group may be linear, cyclic, branched, aromatic, or have a combination of such structures.

[0062] If g' is 1, and R 8 Specific examples of silicon hydride compounds (B) where is a divalent hydrocarbon group include the following:

[0063] [ka]

[0064] In these or other embodiments, the silicon hydride compound (B) constitutes an organohydrogensiloxane that may be a disiloxane, trisiloxane, or polysiloxane. Examples of organohydrogensiloxanes suitable for use as the silicon hydride compound (B) include, but are not limited to, siloxanes having the following formulas: PhSi(OSiMe2H)3, Si(OSiMe2H)4, MeSi(OSiMe2H)3, and Ph2Si(OSiMe2H)2, where Me is methyl and Ph is phenyl. Additional examples of organohydrogensiloxanes suitable for the purpose of silicon hydride compound (B) include 1,1,3,3-tetramethyldisiloxane, 1,1,3,3-tetraphenyldisiloxane, phenyltris(dimethylsiloxy)silane, 1,3,5-trimethylcyclotrisiloxane, trimethylsiloxy-terminated poly(methylhydrogensiloxane), trimethylsiloxy-terminated poly(dimethylsiloxane / methylhydrogensiloxane), and dimethylhydrogensiloxy-terminated poly(methylhydrogensiloxane).

[0065] If the silicon hydride compound (B) contains an organohydrogensiloxane, the silicon hydride compound (B) may contain any combination of M siloxy units, D siloxy units, T siloxy units, and / or Q siloxy units, as long as the silicon hydride compound (B) contains at least one silicon-bonded hydrogen atom. These siloxy units can be combined in various ways to form cyclic, linear, branched, and / or resinous (three-dimensional network) structures. Depending on the selection of M units, D units, T units, and / or Q units, the silicon hydride compound (B) may also be a monomer, polymer, oligomer, linear, branched, cyclic, and / or resinous.

[0066] Since silicon hydride compound (B) contains at least one silicon-bonded hydrogen atom, with respect to the above siloxy units, silicon hydride compound (B) contains the following siloxy units: (R 7 2HSiO 1 / 2 ), (R 7 H2SiO 1 / 2 ), (H3SiO 1 / 2 ), (R 7 HSiO 2 / 2 ), (H2SiO 2 / 2 ), and / or (HSiO 3 / 2 )(wherein, R 7 These can be independently selected and may optionally include any of the (as defined above) in combination with a siloxy unit that does not contain a silicon-bonded hydrogen atom.

[0067] In certain embodiments, for example, if silicon hydride compound (B) is linear, then silicon hydride compound (B) has the following average formula: (R 7 3SiO 1 / 2 ) e’’ (R 7 2SiO 2 / 2 ) f’’’ (R 7 HSiO 2 / 2 ) g’’ , (In the formula, each R 7 is independently hydrogen or R 5 And each R 5 The elements are independently selected and defined above, and may have e''≧2, f'''≧0, and g''≧2. In certain embodiments, e'' is 2-10, or 2-8, or 2-6. In these embodiments or other embodiments, f''' is 0-1,000, or 1-500, or 1-200. In these embodiments or other embodiments, g'' is 2-500, or 2-200, or 2-100.

[0068] In one embodiment, the silicon hydride compound (B) is linear and contains one or more pendant silicon-bonded hydrogen atoms. In these embodiments, the silicon hydride compound (B) is an average formula; (CH3)3SiO[(CH3)2SiO] f’’’ [(CH3)HSiO] g’’ Si(CH3)3 The formula may be a dimethyl,methyl-hydrogenpolysiloxane having [wherein f''' and g'' are defined above].

[0069] In these embodiments or other embodiments, the silicon hydride compound (B) is linear and contains terminal silicon-bonded hydrogen atoms. In these embodiments, the silicon hydride compound (B) has the average formula: H(CH3)2SiO[(CH3)2SiO] f’’’ Si(CH3)2H The SiH-terminated dimethylpolysiloxane may have [wherein f''' is as defined above]. The SiH-terminated dimethylpolysiloxane may be used alone or in combination with the dimethyl,methylhydrogenpolysiloxanes disclosed above. Furthermore, the SiH-terminated dimethylpolysiloxane may have one trimethylsiloxy terminus such that the SiH-terminated dimethylpolysiloxane may have only one silicon-bonded hydrogen atom. Alternatively, (B) the organohydrogensiloxane may contain silicon-bonded hydrogen atoms at both the pendant and the terminus.

[0070] In a particular embodiment, the silicon hydride compound (B) is given by the following average formula: (R 7 3SiO 1 / 2 ) e’’ (R 5 2SiO 2 / 2 ) f’’’ (R 5 HSiO 2 / 2 ) g’’ (R 5 SiO 3 / 2 ) h , (R 7 3SiO 1 / 2 ) e’’ (R 5 2SiO 2 / 2 ) f’’’ (R 5 HSiO 2 / 2 ) g(SiO 4 / 2 ) i , (R 7 3SiO 1 / 2 ) e’’ (R 5 2SiO 2 / 2 ) f’’’ (R 5 HSiO 2 / 2 ) g’’ (R 5 SiO 3 / 2 ) h (SiO 4 / 2 ) i , (In the formula, each R 7 and R 5 (These are independently selected and may have one of the following (where e'', f''', and g'' are defined above, h≧0, and i is greater than or equal to 0). In each of the above average formulas, the sum of the subscripts is 1.

[0071] Part of the above average formula for silicon hydride compound (B) is resinous when silicon hydride compound (B) contains T siloxy units (indicated by the subscript h) and / or Q siloxy units (indicated by the subscript i). When silicon hydride compound (B) is resinous, it is typically a copolymer containing T siloxy units and / or Q siloxy units in combination with M siloxy units and / or D siloxy units. For example, organohydrogenpolysiloxane resins may be DT resins, MT resins, MDT resins, DTQ resins, MTQ resins, MDTQ resins, DQ resins, MQ resins, DTQ resins, MTQ resins, or MDQ resins.

[0072] In various embodiments where the silicon hydride compound (B) is resinous or constitutes an organopolysiloxane resin, the silicon hydride compound (B) is typically represented by the following formula: (R 9 3SiO 1 / 2 ) j’ (R 9 2SiO 2 / 2 ) k’ (R 9 SiO 3 / 2 )l’ (SiO 4 / 2 ) m’’ (IV) (In the formula, each R 9 These are independently H or a substituted or unsubstituted hydrocarbyl group, provided that there is at least one R in one molecule. 9 H has 0≦j'≦1, 0≦k'≦1, 0≦l'≦1, and 0≦m''≦1, where j'+k'+l'+m''=1.

[0073] In certain embodiments, the silicon hydride compound (B) is generally of formula (R 9 2SiO) r’ (R 9 HSiO) s’ (In the formula, R 9 (These are independently selected and defined above, where r' is an integer from 0 to 7 and s' is an integer from 3 to 10) which can constitute an alkylhydrogencyclosiloxane or alkylhydrogendialkylcyclosiloxane copolymer. Specific examples of this type of preferred organohydrogensiloxane include (OSiMeH)4, (OSiMeH)3(OSiMeC6H 13 ), (OSiMeH)2(OSiMeC6H 13 )2, and (OSiMeH)(OSiMeC6H 13 )3 (where Me represents methyl (-CH3)) is one example.

[0074] The silicon hydride compound (B) may be a single silicon hydride compound or a combination of two or more different silicon hydride compounds.

[0075] Finally, in the third embodiment, both conditions (1) and (2) are true, and as a result, the unsaturated compound (A) also contains at least one silicon-bonded hydrogen atom per molecule, and the composition further contains a silicon hydride compound containing at least one silicon-bonded hydrogen atom per molecule. Examples of unsaturated compounds and silicon hydride compounds suitable for this third embodiment are shown above.

[0076] The unsaturated compound (A) and the silicon hydride compound (B), if present in the composition, may be added to the carrier vehicle. Examples of carrier vehicles are described below.

[0077] The composition may contain, if present, an unsaturated compound (A) and a silicon hydride compound (B) in various amounts or ratios depending on the desired properties or end use of the composition. In various embodiments in which the composition contains components (A) and (B), the composition contains components (A) and (B) in amounts such that it provides a molar ratio of 0.3 to 5 or 0.6 to 3 for silicon-bonded hydrogen atoms to aliphatic unsaturated groups.

[0078] This composition further comprises (C) catalyst.

[0079] Catalyst (C) possesses excellent physical properties and catalytic activity in hydrosilylation reactions. Compared to conventional catalysts for hydrosilylation, including conventional encapsulated catalysts, Catalyst (C) has significantly superior shelf life and long lifespan. Catalyst (C) reduces the processing steps associated with its preparation, does not require encapsulation, and does not need to be used with inhibitors, thus providing long lifespan and stability in a one-component composition, and can be selectively activated at a desired reaction temperature.

[0080] Catalyst (C) contains platinum(II). As is well known in the art, platinum can be in several oxidation states, with 0, +2, and +4 being the most common. The oxidation states of platinum(II) are favorable because platinum(II) binds to specific ligands present in catalyst (C), as described below.

[0081] Typically, platinum(II) exists in the catalyst(C) in the form of individual atoms rather than clustered particles, as is readily understood in the art within the context of metal complexes.

[0082] Catalyst (C) has the formula X2Pt(II)Y2 (wherein each X is the same and selected from a fluorinated acetate group or a halide, and each Y is independently selected from a substituted or unsubstituted pyridine group, provided that if each Y is substituted, it is not linked to other Ys).

[0083] Each X and each Y does not need to be bonded to platinum at a specific position. In other words, catalyst (C) can be cis-trans isomerized and may take either form.

[0084] Each Y independently has the following general formula:

[0085] [ka] (In the formula, R 10 ~R 14 Each of these is independently selected from H, a hydrocarbyl group, a heteroaryl group, a halogen atom, or a heterocarbyl group. Preferred heterocarbyl groups include any of the hydrocarbyl groups listed above, but containing one or more heteroatoms such as oxygen, sulfur, or nitrogen. Preferred halogen atoms include F, Cl, Br, I, or F, Cl and Br, or Cl.

[0086] In a particular embodiment, R 10 ~R 14 If each of them is a hydrocarbyl group, a heteroaryl group, or a heterocarbyl group, then R 10 ~R 14 Each of these has 1 to 12, or 1 to 10, or 1 to 8 carbon atoms.

[0087] In a particular embodiment, R 10 ~R 14 Each of these is independently H or a hydrocarbyl group. In some such embodiments, R 10 ~R 14 Each of these is independently H or an alkyl group. In a particular embodiment, R 10 ~R 14Each of these is H. If each Y is substituted, it does not link to other Ys, so if each Y is a substituted pyridine group, then the R of one of the Ys 10 ~R 14 In either case, the R of the other Y 10 ~R 14 One of them does not form a bridge, that is, R in each Y 10 ~R 14 Each of them is monovalent and does not form a divalent crosslink.

[0088] Suitable halides for X include F, Cl, Br, I, or F, Cl, and Br, or Cl.

[0089] In certain embodiments, each X is the same and is selected from a trifluoroacetate group or Cl, and each Y is an unsubstituted pyridine group.

[0090] In certain embodiments, each X is a trifluoroacetate and each Y is an unsubstituted pyridine group, and as a result, catalyst (C) has the following structure (I) or (II):

[0091] [ka]

[0092] In other embodiments, each X is a halide and each Y is an unsubstituted pyridine group, and as a result, catalyst (C) has one of the following structures (III) to (V):

[0093] [ka] Of course, the trans isomers of catalyst (C) of structures (III) to (V) can also be used in combination with or instead of the specific species mentioned above.

[0094] By selecting ligands X and Y, two or more different catalyst combinations can also be used together as catalyst (C).

[0095] Catalyst (C) can optionally be placed in a vehicle, such as a solvent that solubilizes catalyst (C), or a vehicle that simply supports or disperses catalyst (C) without solubilizing it. Such vehicles are known in the art.

[0096] Suitable vehicles include both linear and cyclic silicones, organic oils, organic solvents, and mixtures thereof. For example, with respect to a silicone, the support vehicle may include a polydialkylsiloxane, such as polydimethylsiloxane.

[0097] The vehicle also contains hexamethylcyclotrisiloxane, octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, dodecamethylcyclohexasiloxane, octamethyltrisiloxane, decamethyltetrasiloxane, dodecamethylpentasiloxane, tetradecamethylhexasiloxane, hexadeamethylheptasiloxane, heptamethyl-3-{(trimethylsilyl)oxy)}trisiloxane, hexamethyl-3,3,bis{(trimethylsilyl)oxy}trisiloxane, pentamethyl{(trimethylsilyl)oxy}cyclotrisiloxane, as well as polydimethylsiloxane, polyethylsiloxane, polymethylethylsiloxane, polymethylphenylsiloxane, polydiphenylsiloxane, caprylyl methicone, and any mixture thereof, at 1 to 1,000 mm at 25°C. 2 It may be a low-viscosity organopolysiloxane having a viscosity in the range of / second, or a volatile methylsiloxane, volatile ethylsiloxane, or volatile methylethylsiloxane.

[0098] Alternatively, the vehicle may contain organic solvents. Examples of organic solvents include aromatic hydrocarbons such as benzene, toluene, xylene, and mesitylene; aliphatic hydrocarbons such as heptane, hexane, and octane; glycol ethers such as propylene glycol methyl ether, dipropylene glycol methyl ether, propylene glycol n-butyl ether, propylene glycol n-propyl ether, and ethylene glycol n-butyl ether; halogenated hydrocarbons such as dichloromethane, 1,1,1-trichloroethane, and chloroform; ketones such as acetone, methyl ethyl ketone, or methyl isobutyl ketone; acetates such as ethyl acetate, butyl acetate, ethylene glycol monoethyl ether acetate, and propylene glycol methyl ether acetate; alcohols such as methanol, ethanol, isopropanol, butanol, or n-propanol; and other organic compounds that exist as liquids / fluids at typical reaction temperatures, such as dimethyl sulfoxide, dimethylformamide, acetonitrile, tetrahydrofuran, white spirit, mineral spirit, naphtha, and n-methylpyrrolidone, as well as their derivatives, modifications, and combinations.

[0099] Catalyst (C) can be prepared by those skilled in the art, taking into consideration the description herein, including the appended examples. For example, if catalyst (C) has structure (I) or (II), catalyst (C) can be synthesized, for example, by reacting (Py)2PtI2 with silver trifluoroacetate (wherein Py is pyridine). If Y is a substituted pyridine group, the substituted pyridine group is used in place of pyridine in (Py)2PtI2. Generally, increasing the molar ratio of silver trifluoroacetate to (Py)2PtI2 results in a preference for the trans isomer over the cis isomer. Alternatively, if catalyst (C) has structure (III) above, catalyst (C) can be synthesized, for example, by reacting potassium tetrachloroplatinate with pyridine. If Y is a substituted pyridine group, the substituted pyridine group is used in place of pyridine.

[0100] For example, catalyst (C) may inhibit the hydrosilylation reaction at room temperature, but may readily catalyze the hydrosilylation reaction at high temperatures. For example, in certain embodiments, catalyst (C) can prevent the conversion of more than 10 mol%, or more than 9 mol%, or more than 8 mol%, or more than 6 mol%, or more than 5 mol% of the aliphatic unsaturated groups in unsaturated compound (A), when the catalyst is present together with components (A) and (B). Catalyst (C) can typically prevent such conversion for at least 1 hour, or at least 1 day, or at least 1 week, or at least 1 month at room temperature. In these embodiments or other embodiments, the composition can be heated to a temperature of 60°C, or 65°C, or 70°C, or 75°C, or 80°C, or 85°C, or 90°C for 1 hour without gelation.

[0101] Catalyst (C) is present in the composition in a catalytic amount, i.e., an amount (amount) or quantity sufficient to promote the reaction or curing under the desired conditions. The catalytic amount of catalyst (C) may be greater than 0.01 ppm or greater than 1,000 ppm (e.g., up to 10,000 ppm or more). In certain embodiments, a typical catalytic amount of catalyst (C) is less than 5,000 ppm, or less than 2,000 ppm, or less than 1,000 ppm (but greater than 0 ppm in all cases). In certain embodiments, the catalytic amount of catalyst (C) may be in the range of 0.01 to 1,000 ppm, or 0.01 to 100, or 0.01 to 50, or 0.25 to 50, or 0.5 to 40 ppm of metal, based on the weight of the components in the composition. The range may relate only to the metal (i.e., platinum) content in catalyst (C). As is understood in the art, the catalytic amount of catalyst (C) may depend on the selection of components (A) and (B).

[0102] The composition may further contain one or more optional components, including adhesion promoters, carrier vehicles, dyes, pigments, antioxidants, heat stabilizers, flame retardants, flow control additives, biocides, fillers (including bulking and reinforcing fillers), surfactants, thixotropy imparters, water, carrier vehicles or solvents, pH buffers, etc. In certain embodiments, the composition does not contain any hydrosilylation inhibitors. The composition may be in any form and may, for example, be incorporated into further compositions as a component of the composition. For example, the composition may be in the form of an emulsion or incorporated into an emulsion. The emulsion may be an oil-in-water emulsion, a water-in-oil emulsion, a silicone-in-oil emulsion, etc. The composition itself may be such an emulsion in a continuous phase or a discontinuous phase.

[0103] This composition can be prepared by combining components (A), (B), and (C) with any selected components in any order of addition, optionally in a masterbatch, and optionally under shear.

[0104] A method for preparing hydrosilylation reaction products is also provided. Hydrosilylation reaction products are formed from the composition and may take various forms depending on the section of components in the composition.

[0105] This method involves reacting an aliphatic unsaturated group with a silicon-bonded hydrogen atom in the presence of catalyst (C). Catalyst (C) can be used, for example, in place of or in addition to conventional hydrosilylation catalysts in any hydrosilylation reaction. As described above, in certain embodiments, catalyst (C) is not washed before use in a method for preparing the hydrosilylation reaction product.

[0106] Aliphatic unsaturated groups are present in the unsaturated compound (A). At least one of the following two conditions is met: (1) the unsaturated compound (A) also contains at least one silicon-bonded hydrogen atom per molecule, and / or (2) the silicon-bonded hydrogen atom is present in a silicon hydride (B) compound separate from the unsaturated compound (A). In the first embodiment, condition (1) is true, and as a result the unsaturated compound (A) also contains at least one silicon-bonded hydrogen atom per molecule. In the second embodiment, condition (2) is true, and as a result the composition further comprises a silicon hydride compound (B) containing at least one silicon-bonded hydrogen atom per molecule. Finally, in the third embodiment, both conditions (1) and (2) are true, and as a result the unsaturated compound (A) also contains at least one silicon-bonded hydrogen atom per molecule, and the composition further comprises a silicon hydride compound (B) containing at least one silicon-bonded hydrogen atom per molecule. These embodiments are described in detail above with respect to the composition itself.

[0107] The hydrosilylation reaction products prepared by this method are not limited and generally depend on the unsaturated compound (A) and, if used, the silicon hydride compound (B). For example, the hydrosilylation reaction products may be monomers, oligomers, polymers, resins, etc. The hydrosilylation reaction products may include fluids, oils, gels, elastomers, rubbers, resins, etc. The hydrosilylation reaction products may take any form as understood in the art, based on the selection of the unsaturated compound (A) and, if used, the silicon hydride compound (B).

[0108] The hydrosilylation reaction product may also include various by-products formed through the hydrosilylation reaction. For example, the hydrosilylation reaction product typically includes the target species and various by-products. The hydrosilylation reaction product may also include other components, such as a carrier or solvent, if the method and reaction are carried out therein and / or if the composition contains such components. The method may further include, for example, isolating the target species via any preferred purification method. The following examples are intended to illustrate the present invention and should not be considered in any way as limiting the scope of the invention.

[0109] The following examples are intended to illustrate the present invention and should not be considered to limit its scope.

[0110] The specific components used in the examples are listed in Table 1 below.

[0111] [Table 1-1]

[0112] [Table 1-2]

[0113] Gas chromatography (GC): Gas chromatograms were collected using a Shimadzu GC-2010 Plus equipped with an Rxi-5ms (5% diphenyl, 95% dimethylpolysiloxane) column (14.5 m, 0.25 mm ID). Conversion was quantified using an internal decane standard. The split ratio was 20:1. The temperature gradient and elution time used in GC are shown in Tables 2 and 3 below.

[0114] [Table 2] Total time: 23.50 minutes

[0115] [Table 3]

[0116] Inductively coupled plasma mass spectrometry (ICP-MS) The platinum content in the following specific examples was determined using ICP-MS. In the ICP-MS, each sample was digested with a mixture of 5 mL of 70% nitric acid, 1 mL of concentrated sulfuric acid (97%), 1 mL of concentrated hydrofluoric acid, 1 mL of 30% hydrogen peroxide, and 2.5 mL of Millipore water to obtain the sample solution. The sample solutions were then placed in a CEM MARS6 microwave digestion system using the parameters shown in Table 4.

[0117] [Table 4]

[0118] After digestion, the sample solution was diluted to its final volume. A standard calibration curve for Pt in the range of 0.5–5 ppm was prepared in 2% nitric acid. The sample and standard substances were analyzed using a Perkin Elmer Optima 8300 ICP-OES instrument with the following operating parameters shown in Table 5.

[0119] [Table 5]

[0120] Using the axial field of view, signal intensity was measured at both 265.945 nm and 214.423 nm. The final concentration was calculated via linear regression using the wavelength that yielded the lowest RSD (R 2 (>0.999). When the test was performed using a QC standard material after the sample, the concentration was within ±10% of the expected value.

[0121] Preparation Example 1: Synthesis of Catalyst (C1): In a dark nitrogen glove box, (Py)2PtI2 (0.0200 g, 0.027 mmol, 1 equivalent), silver trifluoroacetate (0.0090 g, 0.054 mmol, 2 equivalents), and a stirring bar were placed in a scintillation vial and then covered with insulating tape to avoid exposure. The reaction mixture was stirred overnight and then reduced under vacuum. The white product was rinsed with hexane (3 × 5 mL) and benzene (3 × 5 mL) and filtered through a diatomaceous earth pipette. The remaining white product was collected in dichloromethane (5 × 5 mL) and reduced under vacuum to obtain the catalyst (C1) (trans-(Py)2Pt(OOCCF3)2) in the form of a white powder in 96% yield. 1 H NMR (500MHz, methylene chloride-d2) δ 8.68 (d, J = 6.2 Hz, 4H), 7.91 (t, J = 7.4 Hz, 2H), 7.42 (t, J = 6.3 Hz, 4H). 19 F NMR (500MHz, methylene chloride-d2) δ -74.81. HRMS(ESI + ):C 12 H 10 F3N2O -2 Pt + The calculated value is 466.0, and the measured value is 466.0.

[0122] Preparation Example 2: Synthesis of Catalyst (C2): In a dark nitrogen glove box, (Py)2PtI2 (0.0200 g, 0.027 mmol, 1 equivalent), silver trifluoroacetate (0.0135 g, 0.081 mmol, 3 equivalents), and a stirring bar were placed in a scintillation vial and then covered with insulating tape to avoid exposure. The reaction mixture was stirred overnight and then reduced under vacuum. The white product was rinsed with hexane (3 x 5 mL) and benzene (3 x 5 mL) and filtered through a diatomaceous earth pipette. The remaining white product was collected in dichloromethane (5 x 5 mL) and reduced under vacuum to obtain the catalyst (C2) (cis-(Py)2Pt(OOCCF3)2) in the form of a white powder in 93% yield. 1 H NMR (500MHz, methylene chloride-d2) δ 8.64 (d, J = 5.3 Hz, 4H), 7.90 (tt, J = 7.7, 1.6 Hz, 2H), 7.39 (t, J = 7.4 Hz, 4H). 19F NMR (500MHz, methylene chloride-d2) δ -75.11. HRMS(ESI + ):C 12 H 10 F3N2O -2 Pt + The calculated value is 466.0, and the measured value is 466.0.

[0123] Preparation Example 3: Synthesis of Catalyst (C3): In a 25 mL round-bottom flask, potassium tetrachloroplatinate (0.100 g, 0.24 mmol, 1 equivalent), H2O (1.5 mL), and a stirring bar were added and stirred until a red solution was obtained. In a separate 25 mL round-bottom flask, pyridine (0.0572 g, 0.72 mmol, 3 equivalents) was dissolved in H2O (0.5 mL) to obtain a pyridine solution. The filtrate of this red solution was added dropwise to the pyridine solution over 3 minutes and stirred for 3 hours. A white precipitate immediately formed, and the aqueous solution was filtered after it was no longer red. The resulting off-white powder was rinsed with H2O (3 × 2 mL), EtOH (3 × 2 mL), and diethyl ether (3 × 1 mL), and the catalyst (C3) in the form of a white powder was collected in 92% yield. 1 H NMR (500MHz, methylene chloride-d2) δ 8.70 (d, J = 5.0 Hz, 4H), 7.87 (s, 2H), 7.38-7.32 (m, 4H).

[0124] Preparation Example 4: Synthesis of Catalyst (C4): In a 250 mL round-bottom flask, potassium tetrachloroplatinate (2.0 g, 0.0048 mol, 1 equivalent), H2O (3.0 mL), and a stirring bar were added and stirred until a red solution was obtained. In a separate 40 mL scintillation vial, potassium bromide (3.4 g, 0.029 mol, 6 equivalents) was dissolved in H2O (30 mL) to obtain a potassium bromide solution. The potassium bromide solution was added to the round-bottom flask. In a 20 mL scintillation vial, pyridine (1.1 g, 0.014 mol, 3 equivalents) was dissolved in H2O (10 mL) to obtain a pyridine solution. When the pyridine solution was added dropwise over 3 minutes, a white precipitate immediately began to form. A reflux condenser and gas adapter were attached to the round-bottom flask. The reaction mixture was stirred and heated at 90°C for 12 hours under a positive nitrogen stream, then filtered. After rinsing the off-white powder with H2O (3 × 5 mL), EtOH (3 × 5 mL), and Et2O (3 × 3 mL), the catalyst (C4) in the form of a white-yellow powder was collected in a yield of 65%.

[0125] Preparation Example 5: Synthesis of Catalyst (C5): In a 25 mL round-bottom flask, potassium tetrachloroplatinate (0.100 g, 0.24 mmol, 1 equivalent), H2O (1.5 mL), and a stirring bar were added and stirred until a red solution was obtained. In a separate 20 mL scintillation vial, sodium iodide (0.240 g, 1.6 mmol, 6 equivalents) was dissolved in H2O (1.5 mL) to obtain a sodium iodide solution. The sodium iodide solution was added dropwise to the round-bottom flask over 1 minute, and then stirred for 10 minutes. The red solution changed to black with a darker orange hue. After stirring for 10 minutes, the black solution and rinse (5 × 2 mL) were filtered through a Buchner funnel. In a separate 25 mL round-bottom flask, pyridine (0.0572 g, 0.72 mmol, 3 equivalents) was dissolved in H2O (0.5 mL). The filtrate was added dropwise to the pyridine solution over 3 minutes and stirred for 30 minutes. A yellow precipitate immediately formed and was filtered off after 30 minutes. The yellow powder was rinsed with H2O (3 × 2 mL), EtOH (3 × 2 mL), and Et2O (3 × 1 mL), and the catalyst (C5) was collected as a yellowish-brown powder with a yield of 88%. 1H NMR (500MHz, methylene chloride-d2) δ 8.85 (dt, J = 5.1, 1.6 Hz, 4H), 7.82 (tt, J = 7.7, 1.5 Hz, 2H), 7.35 (ddd, J = 7.7, 5.0, 1.5 Hz, 4H). 13 C NMR (126MHz, methylene chloride-d2) δ 152.55,138.65,126.34. HRMS(ESI + ):C 10 H 11 N2I2Pt + The calculated value is 607.87, and the measured value is 607.86.

[0126] Preparation Example 6: Synthesis of Comparative Catalyst (C-C2): In a dark nitrogen glove box, (BPy)PtI2 (0.0200 g, 0.035 mmol, 1 equivalent), silver trifluoroacetate (0.0229 g, 0.104 mmol, 3 equivalents), and a stirring bar were placed in a scintillation vial and then covered with insulating tape to avoid exposure. The reaction mixture was stirred overnight and then reduced under vacuum. A white product was obtained, which was rinsed with hexane (3 × 5 mL) and benzene (3 × 5 mL) and filtered through a diatomaceous earth pipette. The resulting yellowish-brown product was collected in dichloromethane (5 × 5 mL) and reduced under vacuum to obtain the comparative catalyst (C-C2) in the form of a yellow powder in 45% yield. 1 H NMR (500MHz, methylene chloride-d2) δ 8.37 (dd, J = 5.8, 1.4 Hz, 2H), 8.24 (td, J = 7.9, 1.5 Hz, 2H), 8.02 (d, J = 8.1 Hz, 2H), 7.60 (ddd, J = 7.5, 5.9, 1.4 Hz, 2H). 19 F NMR (500 MHz, methylene chloride -d2) δ -74.89.

[0127] Preparation Example 7: Synthesis of Comparative Catalyst (C-C3): In a dark nitrogen glove box, cis-(Py)2PtI2 (0.0200 g, 0.033 mmol, 1 equivalent), silver acetate (0.0165 g, 0.099 mmol, 3 equivalents), and a stirring bar were placed in a scintillation vial and then covered with insulating tape to avoid exposure. The reaction mixture was stirred overnight and then reduced under vacuum. A white product was obtained, which was rinsed with hexane (3 × 5 mL) and benzene (3 × 5 mL) and filtered through a diatomaceous earth pipette. The obtained white product was collected in dichloromethane (5 × 5 mL) and reduced under vacuum to obtain a comparative catalyst (C-C3) in the form of a white powder in 89% yield. 1 H NMR (500MHz, methylene chloride-d2) δ 8.73 (d, J = 5.9 Hz, 4H), 7.82 (t, J = 7.7 Hz, 2H), 7.31 (t, J = 6.9 Hz, 4H), 1.89 (s, 6H). 13 ¹³C NMR (500MHz, methylene chloride-d2) δ 179.86, 155.53, 140.41, 127.86, 24.40. IR stretches (cm -1 ):3070,2925,1639,1600,1450,1361,1301,1012,768,690,615,458. HRMS(ESI + ):C 12 H 13 N2O2Pt + The calculated value is 412.1, and the measured value is 412.1.

[0128] Preparation Example 8: Synthesis of Comparative Catalyst (C-C4): In a dark nitrogen glove box, cis-(Py)2PtI2 (0.020 g, 0.033 mmol, 1 equivalent), silver acetate (0.011 g, 0.033 mmol, 2 equivalents), and a stirring bar were placed in a scintillation vial and then covered with insulating tape to avoid exposure. The reaction mixture was stirred overnight and then reduced under vacuum. A white product was obtained, which was rinsed with hexane (3 × 5 mL) and benzene (3 × 5 mL) and filtered through a diatomaceous earth pipette. The obtained white product was collected in dichloromethane (5 × 5 mL) and reduced under vacuum to obtain a comparative catalyst (C-C4) in the form of a white powder in 90% yield. 1H NMR (500MHz, methylene chloride-d2) δ 8.69 (d, J = 6.5 Hz, 4H), 7.82 (t, J = 6.5 Hz, 2H), 7.30z (t, J = 6.5 Hz, 4H), 1.88 (s, 6H). 13 ¹³C NMR (500MHz, methylene chloride-d2) δ 155.49, 140.31, 127.84, 55.79, 55.57, 55.35, 55.14, 54.92, 24.44. IR stretches (cm -1 ):3069,2925,1639,1605,1450,1360,1012,768,690,613,460. HRMS(ESI + ):C 12 H 13 N2O2Pt + The calculated value is 412.1, and the measured value is 412.1.

[0129] Examples 1-79 and Comparative Examples 1-5: General Hydrosilylation Procedures Examples 1-79 and Comparative Examples 1-5 illustrate hydrosilylation reactions, and the reactions in Examples 1-79 are according to this disclosure.

[0130] Examples 1-79 and Comparative Examples 1-5 follow various general hydrosilylation procedures as described below. Specific variable elements described in each general hydrosilylation procedure are identified in Table 6 below. To monitor the reaction rate, approximately 0.01 mL aliquots were extracted from the reaction mixture using a needle and syringe, quenched in 1.5 mL of pentane, and analyzed via GC. The specific general procedures described below utilized a silicone masterbatch. A silicone masterbatch was formed by placing 500 g of the unsaturated compound (A2) and 4.8 g of silicon hydride (B2) in a dental cup and subsequently mixing them for 20 seconds at 3,500 rpm via a Flacktek speed mixer (DAC 150.1 FVZ-K).

[0131] Examples 1-24 and 36, General Procedure 1: A 5 g silicone masterbatch was placed in a 20 mL scintillation vial. The vial was placed in a glove box overnight, and the catalyst (identified in Table 6 and used as 0.30 mg stock solution (0.51 μmol, 20 ppm), 0.15 mg stock solution (0.26 μmol, 10 ppm), or 0.074 mg stock solution (0.13 μmol, 5 ppm)) was added as stock solution to obtain the mixture. The stock solution was prepared in dichloromethane in a 2 mL volumetric flask in a nitrogen glove box. The mixture was manually stirred for 5 minutes or approximately 200 rpm. Qualitative measurements were performed at room temperature, 50°C, 80°C, and 100°C.

[0132] Examples 25-35 and 37, General Procedure 2: A 5 g silicone masterbatch was placed in a 20 mL scintillation vial. The vial was placed in a glove box overnight, and the catalyst (identified in Table 6 and used as 0.22 mg stock solution (0.51 μmol, 20 ppm), 0.11 mg stock solution (0.26 μmol, 10 ppm), or 0.054 mg stock solution (0.13 μmol, 5 ppm)) was added as stock solution to obtain the mixture. The stock solution was prepared in dichloromethane in a 2 mL volumetric flask in a nitrogen glove box. The mixture was manually stirred for 5 minutes or approximately 200 rpm. Qualitative measurements were performed at room temperature, 50°C, 80°C, and 120°C.

[0133] Example 38: General Procedure 3: In a nitrogen glove box, unsaturated compound (A1) (0.6312 g, 0.00563 mol, 1 equivalent), silicon hydride (B1) (1.2516 g, 0.00562 mol, 1 equivalent), decane (0.3984 g, 0.00280 mol), and toluene (1.7721 g) were added to a 20 mL scintillation vial. After time point t=0, a catalyst solution (0.024 mg stock solution (2.0 mg of catalyst (C3) in 2 mL of dichloromethane, 0.056 μmol, 6 ppm)) was added to the reactants. Aliquots were taken at specific time points as listed in Table 6, and the conversion of unsaturated compound (A1) was tracked by gas chromatography (GC).

[0134] Examples 39-40: General Procedure 4: In a nitrogen glove box, unsaturated compound (A1) (1.8936 g, 0.0169 mol, 1 equivalent), silicon hydride (B1) (3.7548 g, 0.0169 mol, 1 equivalent), decane (1.1952 g, 0.0084 mol), and toluene (5.3163 g) were added to a 20 mL scintillation vial to obtain a solution. The solution was mixed, and using a volumetric pipette, 5 mL of the solution was dispensed into three 20 mL scintillation vials. Each vial contained unsaturated compound (A1) (0.6312 g, 0.00563 mol, 1 equivalent), silicon hydride (B1) (1.2516 g, 0.00562 mol, 1 equivalent), decane (0.3984 g, 0.00280 mol), and toluene (1.7721 g). The catalyst (identified in Table 6 and used as either 0.024 mg stock solution (0.056 μmol, 3 ppm) or 0.012 mg stock solution (0.028 μmol, 0.0005 mol%)) was added as stock solution to obtain the mixture. The stock solution was prepared in dichloromethane in a 2 mL volumetric flask in a nitrogen glove box. After time point t=0, the catalyst was added to the reactants. Aliquots were taken at 50°C or 120°C at the specific time points listed in Table 6. The conversion of the unsaturated compound (A1) was tracked by gas chromatography (GC).

[0135] Examples 41-44, General Procedure 5: In a nitrogen glove box, unsaturated compound (A1) (1.8936 g, 0.0169 mol, 1 equivalent), silicon hydride (B1) (3.7548 g, 0.0169 mol, 1 equivalent), decane (1.1952 g, 0.0084 mol), and toluene (5.3163 g) were added to a 20 mL scintillation vial to obtain a solution. The solution was mixed, and using a volumetric pipette, 5 mL of the solution was dispensed into three 20 mL scintillation vials. Each vial contained unsaturated compound (A1) (0.6312 g, 0.00563 mol, 1 equivalent), silicon hydride (B1) (1.2516 g, 0.00562 mol, 1 equivalent), decane (0.3984 g, 0.00280 mol), and toluene (1.7721 g). The catalyst (identified in Table 6 and used as 0.016 mg stock solution (0.028 μmol, 3 ppm)) was added as stock solution to obtain the mixture. The stock solution was prepared in dichloromethane in a 2 mL volumetric flask in a nitrogen glove box. After time point t=0, the catalyst was added to the reactants. Aliquots were taken at the specific time points listed in Table 6, and the conversion of the unsaturated compound (A1) was tracked by gas chromatography (GC). The reaction in general procedure 5 is carried out at either room temperature or 80°C, as described in Table 6.

[0136] Examples 45-55, General Procedure 6: A 5 g silicone masterbatch was placed in a 20 mL scintillation vial. The vial was placed in a glove box overnight, and catalyst (C4) was added as stock solution in the form of 0.30 mg (0.51 μmol, 20 ppm), 0.15 mg (0.26 μmol, 10 ppm), or 0.074 mg (0.13 μmol, 5 ppm) to obtain the mixture. The stock solution was prepared in dichloromethane in a 2 mL volumetric flask in a nitrogen glove box. Each mixture was manually stirred for 5 minutes or approximately 200 revolutions per minute. Qualitative measurements were performed at room temperature, 50°C, 80°C, 100°C, and 120°C, the temperatures at which various examples were conducted, as shown in Table 6 below.

[0137] Examples 56-60, General Procedure 7: In a nitrogen glove box, unsaturated compound (A1) (1.8936 g, 0.0169 mol, 1 equivalent), silicon hydride (B1) (3.7548 g, 0.0169 mol, 1 equivalent), decane (1.1952 g, 0.0084 mol), and toluene (5.3163 g) were added to a 20 mL scintillation vial to obtain a solution. The solution was mixed, and using a volumetric pipette, 5 mL of the solution was dispensed into three 20 mL scintillation vials. Each vial contained unsaturated compound (A1) (0.6312 g, 0.00563 mol, 1 equivalent), silicon hydride (B1) (1.2516 g, 0.00562 mol, 1 equivalent), decane (0.3984 g, 0.00280 mol), and toluene (1.7721 g). After taking time t=0, the catalyst solution (2.0 mg of catalyst (C4), 0.028 μmol, 3 ppm in 2 mL of dichloromethane) was added to the reactants. Qualitative measurements were performed from aliquots at room temperature, 50°C, 80°C, 100°C, and 120°C.

[0138] Examples 61-74, General Procedure 8: A 5 g silicone masterbatch was placed in a 20 mL scintillation vial. The vial was placed in a glove box overnight, and catalyst (C5) (used as 0.22 mg stock solution (0.51 μmol, 20 ppm), 0.11 mg stock solution (0.26 μmol, 10 ppm), or 0.054 mg stock solution (0.13 μmol, 5 ppm)) was added as stock solution to obtain the mixture. The stock solution was prepared in dichloromethane in a 2 mL volumetric flask in a nitrogen glove box. Each mixture was manually stirred for 5 minutes or approximately 200 rpm. Qualitative measurements were performed at room temperature, 50°C, 80°C, 100°C, and 120°C, as shown in Table 6 below.

[0139] Examples 75-79, General Procedure 9: In a nitrogen glove box, an unsaturated compound (A1) (1.8936 g, 0.0169 mol, 1 equivalent), silicon hydride (B1) (3.7548 g, 0.0169 mol, 1 equivalent), decane (1.1952 g, 0.0084 mol), and toluene (5.3163 g) were added to a 20 mL scintillation vial to obtain a solution. The solution was mixed, and 5 mL of the solution was dispensed into three 20 mL scintillation vials using a volumetric pipette. Each vial contained an unsaturated compound (A1) (0.6312 g, 0.00563 mol, 1 equivalent), silicon hydride (B1) (1.2516 g, 0.00562 mol, 1 equivalent), decane (0.3984 g, 0.00280 mol), and toluene (1.7721 g). After taking time point t = 0, a catalyst solution (2.0 mg of catalyst (C4) in 2 mL of dichloromethane, 0.028 μmol, 3 ppm) was added to the reactants. Qualitative measurements were performed at room temperature, 50 °C, 80 °C, 100 °C, and 120 °C as shown in Table 6 below. The conversion of the unsaturated compound (A1) was monitored by gas chromatography (GC).

[0140] Comparative Example 1, General Procedure 10: In a nitrogen glove box, into a 20 mL scintillation vial, an unsaturated compound (A1) (1.8936 g, 0.0169 mol, 1 equivalent), silicon hydride (B1) (3.7548 g, 0.0169 mol, 1 equivalent), decane (1.1952 g, 0.0084 mol), and toluene (5.3163 g) were charged to obtain a solution. The solution was mixed, and using a volumetric pipette, 5 mL of the solution was dispensed into three 20 mL scintillation vials. Each vial contained an unsaturated compound (A1) (0.6312 g, 0.00563 mol, 1 equivalent), silicon hydride (B1) (1.2516 g, 0.00562 mol, 1 equivalent), decane (0.3984 g, 0.00280 mol), and toluene (1.7721 g). A catalyst (identified in Table 6 and used as a stock solution of 0.016 mg (0.028 μmol, 5 ppm)) was added as a stock solution to obtain a mixture. The stock solution was prepared in dichloromethane in a 2 mL volumetric flask in the nitrogen glove box. After taking time point t = 0, the catalyst was added to the reactants. Aliquots were taken at room temperature at the specific time points shown in Table 6. The conversion of the unsaturated compound (A1) was monitored by gas chromatography (GC).

[0141] Comparative Example 2, General Procedure 11: Into a dental cup with a capacity of 20 g, 10.1 g of a silicone master mix and 3 μL of a Karstedt catalyst (2% Pt) in xylene were added. The contents of the dental cup were mixed at 3,500 rpm for 20 seconds and then cured. The sample was cured in the dental cup.

[0142] Comparative Example 3, General Procedure 12: In a nitrogen glove box, unsaturated compound (A1) (1.8936 g, 0.0169 mol, 1 equivalent), silicon hydride (B1) (3.7548 g, 0.0169 mol, 1 equivalent), decane (1.1952 g, 0.0084 mol), and toluene (5.3163 g) were added to a 20 mL scintillation vial to obtain a solution. The solution was mixed, and using a volumetric pipette, 5 mL of the solution was dispensed into three 20 mL scintillation vials. Each vial contained unsaturated compound (A1) (0.6312 g, 0.00563 mol, 1 equivalent), silicon hydride (B1) (1.2516 g, 0.00562 mol, 1 equivalent), decane (0.3984 g, 0.00280 mol), and toluene (1.7721 g). The catalyst (identified in Table 6 and used as 0.016 mg stock solution (0.028 μmol, 3 ppm)) was added as stock solution to obtain the mixture. The stock solution was prepared in dichloromethane in a 2 mL volumetric flask in a nitrogen glove box. After time point t=0, the catalyst was added to the reactants. Aliquots were taken at room temperature at the specific time points listed in Table 6. The conversion of the unsaturated compound (A1) was tracked by gas chromatography (GC).

[0143] Comparative Examples 4-5, General Procedure 13: In a nitrogen glove box, unsaturated compound (A1) (0.6312 g, 0.00563 mol, 1 equivalent), silicon hydride (B1) (1.2516 g, 0.00562 mol, 1 equivalent), decane (0.3984 g, 0.00280 mol), and toluene (1.7721 g) were added to a 20 mL scintillation vial to obtain a mixture. After taking the first aliquot at t=0, the catalyst (identified in Table 6 and used as 0.13 mg stock solution (0.28 μmol, 3 ppm)) was added to the second scintillation vial as dichloromethane stock solution, pumped down, and rinsed with hexane (3 × 0.5 mL). The mixture was added to the catalyst, and the reaction was stirred at room temperature. Aliquots were taken at the specific time points shown below, and the conversion of unsaturated compound (A1) was tracked by gas chromatography (GC).

[0144] In Table 6 below, SH means "silicon hydride" and UC means "unsaturated compound".

[0145] [Table 6-1]

[0146] [Table 6-2]

Claims

1. A composition, (A) An unsaturated compound containing at least one aliphatic unsaturated group per molecule, and meeting the following two conditions: (1) The unsaturated compound (A) also contains at least one silicon-bonded hydrogen atom per molecule, and / or (2) The composition further comprises (B) a silicon hydride compound containing at least one silicon-bonded hydrogen atom per molecule, and (A) an unsaturated compound, (C) Formula X ２ Pt(II)Y ２ A composition comprising a catalyst having (wherein each X is the same and selected from a fluorinated acetate group or a halide, and each Y is independently selected from a substituted or unsubstituted pyridine group, provided that if each Y is substituted, it does not link to other Ys).

2. The composition according to claim 1, wherein in the catalyst (C), each X is the same and selected from a trifluoroacetate group or Cl, and each Y is an unsubstituted pyridine group.

3. The composition according to claim 1 or 2, wherein in catalyst (C), each X is a trifluoroacetate and each Y is an unsubstituted pyridine group, and as a result, catalyst (C) has the following structure (I) or (II): 【Chemistry 1】

4. The composition according to claim 1 or 2, wherein in catalyst (C), each X is a halide and each Y is an unsubstituted pyridine group, and as a result, catalyst (C) has the following structure (III), (IV), or (V): 【Chemistry 2】

5. The composition according to any one of claims 1 to 4, wherein condition (2) is true, and as a result, the composition further comprises (B) a silicon hydride compound containing at least one silicon-bonded hydrogen atom per molecule.

6. The composition according to any one of claims 1 to 5, wherein component (A) is an organosiloxane having at least one silicon-bonded aliphatic unsaturated group per molecule.

7. The composition according to any one of claims 1 to 6, wherein component (A) is an organopolysiloxane having at least two silicon-bonded aliphatic unsaturated groups per molecule, and component (B) is an organohydrogensiloxane.

8. A method for preparing hydrosilylation reaction products, (C) The process involves reacting an aliphatic unsaturated group with a silicon-bonded hydrogen atom in the presence of a catalyst to obtain the hydrosilylation reaction product. The aliphatic unsaturated group is present in (A) the unsaturated compound, and the following two conditions are met: (1) The unsaturated compound (A) also contains at least one silicon-bonded hydrogen atom per molecule, and / or (2) The silicon-bonded hydrogen atom is present in a silicon hydride compound (B) separate from the unsaturated compound (A), and at least one of these conditions is met. The catalyst (C) is, Formula X ２ Pt(II)Y ２ A method comprising (wherein each X is the same and selected from a fluorinated acetate group or a halide, and each Y is the same and selected from a substituted or unsubstituted pyridine group, provided that if each Y is substituted, it is not linked to other Ys).

9. The method according to claim 8, wherein in the catalyst (C), each X is the same and selected from a trifluoroacetate group or Cl, and each Y is an unsubstituted pyridine group.

10. The method according to claim 8 or 9, wherein in catalyst (C), each X is a trifluoroacetate and each Y is an unsubstituted pyridine group, and as a result, catalyst (C) has the following structure (I) or (II): 【Transformation 3】

11. The method according to claim 8 or 9, wherein in catalyst (C), each X is a halide and each Y is an unsubstituted pyridine group, and as a result, catalyst (C) has the following structure (III), (IV), or (V): 【Chemistry 4】

12. The method according to any one of claims 8 to 11, further comprising preparing the catalyst (C).

13. A hydrosilylation reaction product formed according to the method described in any one of claims 8 to 12.

14. Use of a catalyst in a hydrosilylated curable silicone composition or hydrosilylation reaction, wherein the catalyst (C) is of formula X ２ Pt(II)Y ２ (wherein each X is the same and selected from a fluorinated acetate group or a halide, and each Y is the same and selected from a substituted or unsubstituted pyridine group, provided that if each Y is substituted, it is not linked to other Ys)

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