EP0146307A2
Expired / Lapsed
EP
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Radiation activated hydrosilation
Assignee: 3M Co
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Filing: 1984-12-04
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Granted: —
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Expires: 2004-12-04
Abstract
Abstract This invention relates to a hydrosilation process involving the reaction of a compound containing silicon-bonded hydrogen with a compound containing aliphatic unsaturation in the presence of actinic radiation, and to compositions which contain an actinic radiation-sensitive catalyst that are useful in said process. Numerous patents teach the use of various complexes of cobalt, rhodium, or platinum as catalysts for accelerating the thermally-activated addition reaction Ihydrosilation) between a compound containing silicon-bonded hydrogen and a compound containing aliphatic unsaturation. However, processes for accelerating the ultraviolet radiation activated addition reactions between these compounds are rare. This invention involves a process for the actinic radiation-activated addition reaction of a compound containing silicon-bonded hydrogen with a compound containing aliphatic unsaturation, (hydrosilation), the improvement comprising using, as a platinum hydrosilation catalyst, an (η-cyclopentadienyl)-tri(σ-aliphatic)platinum complex. The invention further involves novel compositions, capable of undergoing hydrosilation, containing the aforementioned platinum complex. Advantages of the platinum complex in accelerating the radiation-activated hydrosilation process include: (1) the reaction composition will not react prematurely or readily in the absence of actinic radiation; (2) since heat is not required, the addition reaction can be carried out on the surface of a heat-sensitive substrate without adversely affecting the substrate; and (3) radiation curing consumes less energy than does thermal curing.
Inventors
- 👤 Timothy J. Drahnak
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-02 16:35
CPC Classifications
C; C07; C07F; C07F7/00; C07F7/02; C07F7/08; C07F15/00; C07F15/0006; C07F15/0086; C08; C08L; C08L83/00; C08L83/04; C08G; C08G77/00; C08G77/04; C08G77/06; C08G77/08; C08G77/20
Claims Analysis
Total Claims: 18
Claim 1
Independent Claim
46 words
A composition which comprises (a) a silicon compound containing at least one hydrogen atom attached to silicon per molecule, there being not more than two hydrogen atoms attached to any one silicon atom, (b) a compound containing aliphatic unsaturation, and (c) a (η 5 -cyclopentadienyl)tri(σ-aliphatic)platinum complex.
Claim 2
Dependent Claim
46 words
A composition which comprises (a) a silicon compound containing at least one hydrogen atom attached to silicon per molecule, there being not more than two hydrogen atoms attached to any one silicon atom, (b) a compound containing aliphatic unsaturation, and (c) a (η 5 -cyclopentadienyl)tri(σ-aliphatic)platinum complex.
Claim 3
Dependent Claim
87 words
The composition of claim 1 wherein the platinum complex is represented by the formula: wherein Cp represents a cyclopentadienyl group that is eta-bonded to the platinum atom, the cyclopentadienyl group being unsubstituted or substituted by one or more groups that do not interfere in a hydrosilation reaction, and each of R 1 , R 2 , and R 3 represents an aliphatic group having from one to eighteen carbon atoms, said R l , R 2, , and R 3 groups being sigma-bonded to the platinum atom.
Claim 4
Dependent Claim
199 words
The composition of claim 1 wherein the platinum complex is represented by the formula: wherein Cp' represents a cyclopentadienyl group that is eta-bonded to the platinum atom and is also bonded to the silicon atom of an organosilyl group; each of R l , R 2 , and R 3 represents an aliphatic group having from one to eighteen carbon atoms, said R l , R 2 ', and R 3 groups being sigma-bonded to the platinum atom; each R 4 can be the same or different and represents a monovalent hydrocarbyl group selected from the group consisting of saturated linear aliphatic groups having 1 to 18 carbon atoms, saturated branched aliphatic groups having 3 to 18 carbon atoms, alicyclic groups having 4 to 18 carbon atoms, aryl groups having 6 to 14 carbon atoms, and R 5 is R 4 or . and r is zero or an integer of 1 to 100; and q is one or two, with the proviso that when q is one, R 5 is R 4 , and when q is two, R 5 is - and that in the complex no more than 50% of the R 4 groups are groups.
Claim 5
Dependent Claim
32 words
The composition of claim 2 wherein the platinum complex is selected from the group consisting of: (η 5 -cyclopentadienyl)trimethylplatinum, (η 5 -methylcyclopentadienyl)trimethylplatinum, (η 5 -trimethylsilycyclopentadienyl)trimethylplatinum, (η 5 -dimethylphenylsilylcyclopentadienyl)trimethylplatinum, and 1,3-bis[(η 5 -cyclopentadienyl)trimethylplatinum]-tetramethyldisiloxane.
Claim 6
Dependent Claim
50 words
The composition of claim 1, said composition comprising from 0.1 to 10.0 equivalent weights of the compound having silicon-bonded hydrogen per equivalent weight of the compound having aliphatic unsaturation, and per 1,000,000 parts by weight of the total composition, from 5 to 1000 parts by weight of the platinum complex.
Claim 7
Dependent Claim
127 words
The composition of claim 1 wherein the compound containing aliphatic saturation is a polyorganosiloxane having the general formula: where each R 8 can be the same or different and represents an unhalogenated or halogenated ethylenically- unsaturated group, an unhalogenated or halogenated alkyl group or cycloalkyl group, or a phenyl group, at least 90% of all R 8 groups being methyl groups, but no more than 10% of all R 8 groups being vinyl or propenyl, and at least two of the R 8 groups being vinyl or propenyl, h is a number having a value from about 75 to 250 such that the polyorganovinylsiloxane has a viscosity from about 0.3 to 3 pascal-seconds (300 to 3000 centipoise) at 25°C, and g is 0, 1, 2, or 3.
Claim 8
Dependent Claim
106 words
The composition of claim 1 wherein the compound containing silicon-bonded hydrogen is a polyorganohydrosiloxane having the general formula: wnerein each R 10 can be the same or different and represents an alkyl group, a cycloalkyl group, a phenyl group, a hydroxyalkyl group, a (polyalkoxy)alkyl group, or hydrogen, at least two but no more than one-half of all the R 10 groups in the siloxane being hydrogen, m is 0, 1, 2 or 3, and n is a number having an average value from one to 275 such that when considered with the value of provides a molecular weight to the polyorganohydrosiloxane of between 134 and 20,000.
Claim 9
Dependent Claim
53 words
The composition of claim 1 wherein the composition comprises from 1 to 40 parts by weight of the polyorganohydrosiloxane, from 60 to 99 parts by weight of the compound having aliphatic unsaturation, and, per 1,000,000 parts by weight of the total composition, from 5 to 1000 parts by weight of the platinum complex.
Claim 10
Dependent Claim
16 words
The composition of claim 1 wherein the compound having aliphatic unsaturation is one having olefinic unsaturation.
Claim 11
Dependent Claim
10 words
The composition of claim 1 further containing a release modifier.
Claim 12
Dependent Claim
22 words
A process which comprises reacting the composition of any of claims 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.
Claim 13
Dependent Claim
20 words
The process of claim 10 wherein said reaction is carried out by means of exposing said composition to actinic radiation.
Claim 14
Dependent Claim
189 words
A platinum complex having the formula wherein Cp' represents a cyclopentadienyl group that is eta-bonded to the platinum atom and is also bonded to the silicon atom of an organosilyl group; each of R 1 , R 2 , and R 3 represents an aliphatic group having from one to eighteen carbon atoms, said R l , R 2, , and R 3 groups being sigma-bonded to the platinum atom. each R 4 can be the same or different and represents a monovalent hydrocarbyl group selected from the group consisting of saturated linear aliphatic groups having 1 to 18 carbon atoms, saturated branched aliphatic groups having 3 to 18 carbon atoms, alicyclic groups having 4 to 18 carbon atoms, aryl groups having 6 to 14 carbon atoms, and R 5 is R 4 or where r is zero or an integer of 1 to 100; and q is one or two, with the proviso that when q is one, R 5 is R 4 , and when q is two, R 5 is and that in the complex no more than 50% of the R 4 groups are groups.
Claim 15
Dependent Claim
189 words
A platinum complex having the formula wherein Cp' represents a cyclopentadienyl group that is eta-bonded to the platinum atom and is also bonded to the silicon atom of an organosilyl group; each of R 1 , R 2 , and R 3 represents an aliphatic group having from one to eighteen carbon atoms, said R l , R 2, , and R 3 groups being sigma-bonded to the platinum atom. each R 4 can be the same or different and represents a monovalent hydrocarbyl group selected from the group consisting of saturated linear aliphatic groups having 1 to 18 carbon atoms, saturated branched aliphatic groups having 3 to 18 carbon atoms, alicyclic groups having 4 to 18 carbon atoms, aryl groups having 6 to 14 carbon atoms, and R 5 is R 4 or where r is zero or an integer of 1 to 100; and q is one or two, with the proviso that when q is one, R 5 is R 4 , and when q is two, R 5 is and that in the complex no more than 50% of the R 4 groups are groups.
Claim 16
Dependent Claim
40 words
A platinum complex according to claim 13 selected from the group consisting of: ( 11 5- trimethylsilylcyclopentadienyl)trimethylplatinum, (η 5 -phenyldimethylsilylcyclopentadienyl)trimethylplatinum, (1,3-bis[(η 5 -cyclopentadienyl)trimethylplatinum]-tetramethyldisiloxane, 1,3,5-tris[(η 5 -cyclopentadienyl)trimethylplatinum]-pentamethyltrisiloxane, and trimethylplatinumcyclopentadienyl terminated polysiloxane having random units of where Cp' represents the cyclopentadienyl group.
Claim 17
Dependent Claim
28 words
A substrate bearing on a surface thereof a layer prepared by applying the composition of claim 1 to said surface and then exposing said composition to actinic radiation.
Claim 18
Dependent Claim
55 words
Sheet material provided with a release surface prepared by applying on a surface of said sheet material the composition of claim 1 and then exposing said composition to actinic radiation, and a layer of normally tacky and pressure-sensitive adhesive bonded firmly to the other major surface of said sheet material, thereby forming a pressure-sensitive tape.
References Cited (Backward Citations)
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