US5629095A
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Radiation curable compositions containing vinyl ether functional polysiloxanes and methods for the preparation
Assignee: Dow Silicones Corp
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Filing: 1995-05-18
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Granted: 1997-05-13
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Expires: 2015-05-18
Abstract
Abstract The present invention relates to radiation curable silicone vinyl ethers and methods for preparing silicone vinyl ethers. More particularly, the present invention relates compositions containing vinyl ether functional silicones and to the preparation and use of silicone vinyl ethers which are curable by addition of photocleavable acids and exposure to ultraviolet or electron beam radiation.
Inventors
- 👤 Valerie J. Bujanowski
- 👤 Shedric O. Glover
- 👤 Susan V. Perz
- 👤 Maris J. Ziemelis
- 👤 Gary R. Homan
- 👤 Michael W. Skinner
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 22:35
CPC Classifications
C; C08; C08K; C08K5/00; C08K5/0008; C08K5/0025; C08G; C08G77/00; C08G77/04; C08G77/06; C08G77/08; C08G77/20; C08G77/38; C09; C09D; C09D183/00; C09D183/04; C09D183/06; Y; Y10; Y10T; Y10T428/00; Y10T428/31504; Y10T428/31652; Y10T428/31663; Y10T428/31667
Claims Analysis
Total Claims: 23
Claim 1
Independent Claim
193 words
A random siloxane polymer having its general formula selected from the group consisting of: ##STR19## wherein R is a monovalent hydrocarbon radical or halohydrocarbon radical having from 1 to 20 carbon atoms, R 1 is a monovalent hydrocarbon or halohydrocarbon radical having from 1 to 8 carbon atoms or is a group having the formula --R 2 OCH═CH 2 wherein R 2 is a divalent hydrocarbon or halohydrocarbon radical having from 1 to 20 carbon atoms, w is a mole percent of from greater than 0 to less than 100, x is a mole percent of from greater than 0 to less than 100, y is a mole percent of from greater than 0 to less than 100, z is a mole percent of from greater than 0 to less than 100, a is an integer of from 0 to 3, b is an integer of from 0 to 2, the sum of w+x+y, the sum of w+x+z, the sum of w+y+z, the sum of w+z, and the sum of w+y being equal to 100 mole percent, with the proviso that at least one --R 2 OCH═CH 2 group exists in each molecule.
Claim 2
Dependent Claim
193 words
A random siloxane polymer having its general formula selected from the group consisting of: ##STR19## wherein R is a monovalent hydrocarbon radical or halohydrocarbon radical having from 1 to 20 carbon atoms, R 1 is a monovalent hydrocarbon or halohydrocarbon radical having from 1 to 8 carbon atoms or is a group having the formula --R 2 OCH═CH 2 wherein R 2 is a divalent hydrocarbon or halohydrocarbon radical having from 1 to 20 carbon atoms, w is a mole percent of from greater than 0 to less than 100, x is a mole percent of from greater than 0 to less than 100, y is a mole percent of from greater than 0 to less than 100, z is a mole percent of from greater than 0 to less than 100, a is an integer of from 0 to 3, b is an integer of from 0 to 2, the sum of w+x+y, the sum of w+x+z, the sum of w+y+z, the sum of w+z, and the sum of w+y being equal to 100 mole percent, with the proviso that at least one --R 2 OCH═CH 2 group exists in each molecule.
Claim 3
Dependent Claim
97 words
A polymer according to claim 1, wherein the polymer is a compound having its general formula selected from the group consisting of: ##STR20## wherein R is a monovalent hydrocarbon radical or halohydrocarbon radical having from 1 to 20 carbon atoms, R 1 is a monovalent hydrocarbon or halohydrocarbon radical having from 1 to 8 carbon atoms or is a group having the formula --R 2 OCH═CH 2 wherein R 2 is a divalent hydrocarbon or halohydrocarbon radical having from 1 to 20 carbon atoms, and wherein w, x, y, z, a, and b are as defined above.
Claim 4
Dependent Claim
101 words
A polymer according to claim 2, wherein the polymer is a compound having its general formula selected from the group consisting of: ##STR21## wherein w is a mole percent of from greater than 0 to less than 100, x is a mole percent of from greater than 0 to less than 100, y is a mole percent of from greater than 0 to less than 100, z is a mole percent of from greater than 0 to less than 100, the sum of w+x+y being equal to 100 mole percent, and the sum of w+z being equal to 100 mole percent.
Claim 5
Independent Claim
295 words
A method of making a curable coating composition comprising mixing: (A) a random siloxane polymer having its general formula selected from the group consisting of: ##STR22## wherein R is a monovalent hydrocarbon radical or halohydrocarbon radical having from 1 to 20 carbon atoms, R 1 is a monovalent hydrocarbon or halohydrocarbon radical having from 1 to 8 carbon atoms or is a group having the formula --R 2 OCH═CH 2 wherein R 2 is a divalent hydrocarbon or halohydrocarbon radical having from 1 to 20 carbon atoms, w is a mole percent of from greater than 0 to less than 100, x is a mole percent of from greater than 0 to less than 100, y is a mole percent of from greater than 0 to less than 100, z is a mole percent of from greater than 0 to less than 100, a is an integer of from 0 to 3, b is an integer of from 0 to 2, the sum of w+x+y, the sum of w+x+z, the sum of w+y+z, the sum of w+z, and the sum of w+y being equal to 100 mole percent, with the proviso that at least one --R 2 OCH═CH 2 group exists in each molecule; and (B) a photocleavable acid selected from the group consisting of an onium salt having its formula selected from the group consisting of R 2 I + MX n - , R 3 S + MX n - , R 3 Se + MX n - , R 4 P + MX n - , and R 4 N + MX n - wherein each R is independently an organic radical having from 1 to 30 carbon atoms, and MX n - is a non-basic, non-nucleophilic anion and nitrobenzyl sulfonate esters.
Claim 6
Independent Claim
295 words
A method of making a curable coating composition comprising mixing: (A) a random siloxane polymer having its general formula selected from the group consisting of: ##STR22## wherein R is a monovalent hydrocarbon radical or halohydrocarbon radical having from 1 to 20 carbon atoms, R 1 is a monovalent hydrocarbon or halohydrocarbon radical having from 1 to 8 carbon atoms or is a group having the formula --R 2 OCH═CH 2 wherein R 2 is a divalent hydrocarbon or halohydrocarbon radical having from 1 to 20 carbon atoms, w is a mole percent of from greater than 0 to less than 100, x is a mole percent of from greater than 0 to less than 100, y is a mole percent of from greater than 0 to less than 100, z is a mole percent of from greater than 0 to less than 100, a is an integer of from 0 to 3, b is an integer of from 0 to 2, the sum of w+x+y, the sum of w+x+z, the sum of w+y+z, the sum of w+z, and the sum of w+y being equal to 100 mole percent, with the proviso that at least one --R 2 OCH═CH 2 group exists in each molecule; and (B) a photocleavable acid selected from the group consisting of an onium salt having its formula selected from the group consisting of R 2 I + MX n - , R 3 S + MX n - , R 3 Se + MX n - , R 4 P + MX n - , and R 4 N + MX n - wherein each R is independently an organic radical having from 1 to 30 carbon atoms, and MX n - is a non-basic, non-nucleophilic anion and nitrobenzyl sulfonate esters.
Claim 7
Dependent Claim
96 words
A method according to claim 4, wherein (A) is a compound having its general formula selected from the group consisting of: ##STR23## wherein R is a monovalent hydrocarbon radical or halohydrocarbon radical having from 1 to 20 carbon atoms, R 1 is a monovalent hydrocarbon or halohydrocarbon radical having from 1 to 8 carbon atoms or is a group having the formula --R 2 OCH═CH 2 wherein R 2 is a divalent hydrocarbon or halohydrocarbon radical having from 1 to 20 carbon atoms, and wherein w, x, y, z, a, and b are as defined above.
Claim 8
Dependent Claim
100 words
A method according to claim 5, wherein (A) is a compound having its general formula selected from the group consisting of: ##STR24## wherein w is a mole percent of from greater than 0 to less than 100, x is a mole percent of from greater than 0 to less than 100, y is a mole percent of from greater than 0 to less than 100, z is a mole percent of from greater than 0 to less than 100, the sum of w+x+y being equal to 100 mole percent, and the sum of w+z being equal to 100 mole percent.
Claim 9
Dependent Claim
13 words
A curable coating composition produced in accordance with the method of claim 6.
Claim 10
Dependent Claim
13 words
A curable coating composition produced in accordance with the method of claim 5.
Claim 11
Dependent Claim
50 words
A method according to claim 4, wherein MX n - is selected from the group consisting of BF 4 - , PR 6 - , AsF 6 - , SbF 6 - , SbCl 6 - , HSO 4 - , ClO 4 - , and SnCl 6 - .
Claim 12
Dependent Claim
25 words
A method according to claim 4, wherein (B) is selected from the group consisting of bis(dodecylphenyl) iodonium hexafluoroarsenate, bis(dodecylphenyl) iodonium hexafluoroantimonate, and dialkylphenyl iodonium hexafluoroantimonate.
Claim 13
Dependent Claim
13 words
A curable coating composition produced in accordance with the method of claim 10.
Claim 14
Dependent Claim
13 words
A curable coating composition produced in accordance with the method of claim 4.
Claim 15
Dependent Claim
343 words
A coated article prepared by a method comprising the steps of: (I) applying a composition to a solid substrate, said composition prepared by mixing: (A) a random siloxane polymer having its general formula selected from the group consisting of: ##STR25## wherein R is a monovalent hydrocarbon radical or halohydrocarbon radical having from 1 to 20 carbon atoms, R 1 is a monovalent hydrocarbon or halohydrocarbon radical having from 1 to 8 carbon atoms or is a group having the formula --R 2 OCH═CH 2 wherein R 2 is a divalent hydrocarbon or halohydrocarbon radical having from 1 to 20 carbon atoms, w is a mole percent of from greater than 0 to less than 100, x is a mole percent of from greater than 0 to less than 100, y is a mole percent of from greater than 0 to less than 100, z is a mole percent of from greater than 0 to less than 100, a is an integer of from 0 to 3, b is an integer of from 0 to 2, the sum of w+x+y, the sum of w+x+z, the sum of w+y+z, the sum of w+z, and the sum of w+y being equal to 100 mole percent, with the proviso that at least one --R 2 OCH═CH 2 group exists in each molecule; and (B) a photocleavable acid selected from the group consisting of an onium salt having its formula selected from the group consisting of R 2 I + MX n - , R 3 S + MX n - , R 3 Se + MX n - , R 4 P + MX n - , and R 4 N + MX n - wherein each R is independently an organic radical having from 1 to 30 carbon atoms, and MX n - is a non-basic, non-nucleophilic anion and nitrobenzyl sulfonate esters; and (II) exposing the coating to an energy source selected from the group consisting of (i) actinic radiation and (ii) actinic radiation in combination with heat in an amount sufficient to cure the coating.
Claim 16
Dependent Claim
343 words
A coated article prepared by a method comprising the steps of: (I) applying a composition to a solid substrate, said composition prepared by mixing: (A) a random siloxane polymer having its general formula selected from the group consisting of: ##STR25## wherein R is a monovalent hydrocarbon radical or halohydrocarbon radical having from 1 to 20 carbon atoms, R 1 is a monovalent hydrocarbon or halohydrocarbon radical having from 1 to 8 carbon atoms or is a group having the formula --R 2 OCH═CH 2 wherein R 2 is a divalent hydrocarbon or halohydrocarbon radical having from 1 to 20 carbon atoms, w is a mole percent of from greater than 0 to less than 100, x is a mole percent of from greater than 0 to less than 100, y is a mole percent of from greater than 0 to less than 100, z is a mole percent of from greater than 0 to less than 100, a is an integer of from 0 to 3, b is an integer of from 0 to 2, the sum of w+x+y, the sum of w+x+z, the sum of w+y+z, the sum of w+z, and the sum of w+y being equal to 100 mole percent, with the proviso that at least one --R 2 OCH═CH 2 group exists in each molecule; and (B) a photocleavable acid selected from the group consisting of an onium salt having its formula selected from the group consisting of R 2 I + MX n - , R 3 S + MX n - , R 3 Se + MX n - , R 4 P + MX n - , and R 4 N + MX n - wherein each R is independently an organic radical having from 1 to 30 carbon atoms, and MX n - is a non-basic, non-nucleophilic anion and nitrobenzyl sulfonate esters; and (II) exposing the coating to an energy source selected from the group consisting of (i) actinic radiation and (ii) actinic radiation in combination with heat in an amount sufficient to cure the coating.
Claim 17
Dependent Claim
23 words
An article according to claim 13, wherein the method further comprises contacting a pressure sensitive adhesive composition with the substrate after step (II).
Claim 18
Dependent Claim
96 words
An article according to claim 13, wherein (A) is a compound having its general formula selected from the group consisting of: ##STR26## wherein R is a monovalent hydrocarbon radical or halohydrocarbon radical having from 1 to 20 carbon atoms, R 1 is a monovalent hydrocarbon or halohydrocarbon radical having from 1 to 8 carbon atoms or is a group having the formula --R 2 OCH═CH 2 wherein R 2 is a divalent hydrocarbon or halohydrocarbon radical having from 1 to 20 carbon atoms, and wherein w, x, y, z, a, and b are as defined above.
Claim 19
Dependent Claim
100 words
An article according to claim 15, wherein (A) is a compound having its general formula selected from the group consisting of: ##STR27## wherein w is a mole percent of from greater than 0 to less than 100, x is a mole percent of from greater than 0 to less than 100, y is a mole percent of from greater than 0 to less than 100, z is a mole percent of from greater than 0 to less than 100, the sum of w+x+y being equal to 100 mole percent, and the sum of w+z being equal to 100 mole percent.
Claim 20
Dependent Claim
25 words
An article according to claim 13, wherein (B) is selected from the group consisting of bis(dodecylphenyl) iodonium hexafluoroarsenate, bis(dodecylphenyl) iodonium hexafluoroantimonate, and dialkylphenyl iodonium hexafluoroantimonate.
Claim 21
Dependent Claim
11 words
An article according to claim 13, wherein the substrate is paper.
Claim 22
Dependent Claim
12 words
An article according to claim 13, wherein the substrate is plastic film.
Claim 23
Dependent Claim
19 words
An article according to claim 13, wherein the actinic radiation is selected from ultraviolet light and electron beam radiation.
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