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US5594042A Expired / Lapsed US ⏱️ 0.0 years remaining

Radiation curable compositions containing vinyl ether functional polyorganosiloxanes

Assignee: Dow Silicones Corp
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Filing: 1994-08-17
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Granted: 1997-01-14
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Expires: 2014-08-17
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Abstract

Abstract The present invention relates to compositions comprising vinyl ether functional siloxanes and aromatic iodonium salt or aromatic sulfonium salt photoinitiators which cure upon exposure to ultraviolet or electron beam radiation. The present invention further relates to use of these compositions in pressure sensitive release applications.

Inventors

  • 👤 Shedric O. Glover
  • 👤 Valeris J. Bujanowski
  • 👤 Maris J. Ziemelis
  • 👤 Michael W. Skinner
  • 👤 Gary R. Homan
  • 👤 Susan V. Perz
  • 👤 John P. Cannady

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-08 12:50
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: 26
Claim 1
Independent Claim 453 words
A curable coating composition comprising: (A) a siloxane compound having the general formula: ##STR9## wherein R is a monovalent hydrocarbon radical or halohydrocarbon radical having from 1 to 20 carbon atoms, R 1 is selected from the group consisting of monovalent hydrocarbon or halohydrocarbon radicals having from 1 to 8 carbon atoms and a group having its formula selected from the group consisting of (i) --R 2 OCH═CH 2 and (ii) --R 2 Si(OR 2 OCH═CH 2 ) 3-c R c wherein R 2 is a divalent hydrocarbon or halohydrocarbon radical having from 1 to 20 carbon atoms, c has a value of 0 to 2, R is as defined above, w has a mole percent of from greater than 0 to 100, x has a mole percent of from 0 to less than 100, y has a mole percent of from 0 to less than 100, z has a mole percent of from 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+z being equal to 100 mole percent, with the proviso that at least one .tbd.SiOR 2 OCH═CH 2 group or .tbd.SiOR 2 Si(OR 2 OCH═CH 2 ) 3-c R c group exists in each compound; and (B) a photoinitiator having its general formula selected from: R.sup.i.sub.a ArI.sup.+ ArR.sup.ii.sub.b X.sup.- or R.sup.iii.sub.a Ar--I.sup.+ --Ar--R.sup.iv.sub.b --O.sub.3 S--Ar--R.sup.iii.sub.a Y.sup.- wherein R i is selected from monovalent hydrocarbon or halohydrocarbon radicals free of aliphatic unsaturation having from 1 to 40 carbon atoms, halogen atoms, a radical selected from NO 2 , CN, COOH, SO 3 H, or alkoxy radicals, hydrocarbon groups substituted with nitro groups, nitrile groups, carboxylic acid groups, sulfonic acid groups, or alkoxy groups, R ii is selected from monovalent hydrocarbon radicals free of aliphatic unsaturation and having from 1 to 40 carbon atoms, hydrocarbon groups substituted with alkoxy groups, arylalkoxy radicals, aryloxy radicals, or halogen atoms, each R iii is independently selected from monovalent hydrocarbon or halohydrocarbon radicals free of aliphatic unsaturation and having from 1 to 20 carbon atoms, halogen atoms, a radical selected from NO 2 , CN, COOH, SO 3 H, or alkoxy radicals, hydrocarbon groups substituted with nitro groups, nitrile groups, carboxylic acid groups, sulfonic acid groups, or alkoxy groups, R iv is selected from alkoxy radicals or aryloxy radicals, Ar denotes arene radicals having from 6 to 40 carbon atoms, a has a value of from 0 to 10, b has value of from 0 to 10, X - is an anion selected from the group consisting of perfluoroalkylsulfonic acid anions, tetrahaloboronic acid anions, tetrakis(perfluoroaryl)boronic acid anions, and tetrakisperfluoroalkylsulfonatoboronic acid anions, and Y - is an aryl sulfonate anion.
Claim 2
Dependent Claim 453 words
A curable coating composition comprising: (A) a siloxane compound having the general formula: ##STR9## wherein R is a monovalent hydrocarbon radical or halohydrocarbon radical having from 1 to 20 carbon atoms, R 1 is selected from the group consisting of monovalent hydrocarbon or halohydrocarbon radicals having from 1 to 8 carbon atoms and a group having its formula selected from the group consisting of (i) --R 2 OCH═CH 2 and (ii) --R 2 Si(OR 2 OCH═CH 2 ) 3-c R c wherein R 2 is a divalent hydrocarbon or halohydrocarbon radical having from 1 to 20 carbon atoms, c has a value of 0 to 2, R is as defined above, w has a mole percent of from greater than 0 to 100, x has a mole percent of from 0 to less than 100, y has a mole percent of from 0 to less than 100, z has a mole percent of from 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+z being equal to 100 mole percent, with the proviso that at least one .tbd.SiOR 2 OCH═CH 2 group or .tbd.SiOR 2 Si(OR 2 OCH═CH 2 ) 3-c R c group exists in each compound; and (B) a photoinitiator having its general formula selected from: R.sup.i.sub.a ArI.sup.+ ArR.sup.ii.sub.b X.sup.- or R.sup.iii.sub.a Ar--I.sup.+ --Ar--R.sup.iv.sub.b --O.sub.3 S--Ar--R.sup.iii.sub.a Y.sup.- wherein R i is selected from monovalent hydrocarbon or halohydrocarbon radicals free of aliphatic unsaturation having from 1 to 40 carbon atoms, halogen atoms, a radical selected from NO 2 , CN, COOH, SO 3 H, or alkoxy radicals, hydrocarbon groups substituted with nitro groups, nitrile groups, carboxylic acid groups, sulfonic acid groups, or alkoxy groups, R ii is selected from monovalent hydrocarbon radicals free of aliphatic unsaturation and having from 1 to 40 carbon atoms, hydrocarbon groups substituted with alkoxy groups, arylalkoxy radicals, aryloxy radicals, or halogen atoms, each R iii is independently selected from monovalent hydrocarbon or halohydrocarbon radicals free of aliphatic unsaturation and having from 1 to 20 carbon atoms, halogen atoms, a radical selected from NO 2 , CN, COOH, SO 3 H, or alkoxy radicals, hydrocarbon groups substituted with nitro groups, nitrile groups, carboxylic acid groups, sulfonic acid groups, or alkoxy groups, R iv is selected from alkoxy radicals or aryloxy radicals, Ar denotes arene radicals having from 6 to 40 carbon atoms, a has a value of from 0 to 10, b has value of from 0 to 10, X - is an anion selected from the group consisting of perfluoroalkylsulfonic acid anions, tetrahaloboronic acid anions, tetrakis(perfluoroaryl)boronic acid anions, and tetrakisperfluoroalkylsulfonatoboronic acid anions, and Y - is an aryl sulfonate anion.
Claim 3
Dependent Claim 14 words
A composition according to claim 1, wherein R is selected from methyl or phenyl.
Claim 4
Dependent Claim 47 words
A composition according to claim 1, wherein R 1 is selected from methyl or a group having its formula selected from --R 2 OCH═CH 2 or --R 2 Si(OR 2 OCH═CH 2 ) 3 wherein R 2 is selected from methylene, ethylene, propylene, butylene, hexylene, or cyclohexyldimethylene.
Claim 5
Dependent Claim 37 words
A composition according to claim 1, wherein Ar is selected from phenyl, naphthyl, anthracenyl, phenanthracenyl, pyrenyl, napthacenyl, 9,10-benzophenanthrenyl, chrysenyl, 1,2-benzanthracenyl, 3,4-benzophenanthrenyl, 3,4-benzopyrene, perylenyl, 1,2,3,4-dibenzanthracenyl, 1,2,5,6-dibenzanthracenyl, 1,2,6,7-dibenzoanthracenyl, 1,2,7,8-dibenzanthracenyl, 1,2,6,7-dibenzophenanthracenyl, 1,2,7,8-dibenzophenanthracenyl, pentacenyl, picenyl, coronenyl, 1,2,4,5-dibenzopyrene, hexacenyl, phenylhexadecenyl, or anthracenylhexacenyl.
Claim 6
Dependent Claim 72 words
A composition according to claim 1, wherein the monovalent hydrocarbon or halohydrocarbon radicals free of aliphatic unsaturation having from 1 to 40 carbon atoms of R i and R ii are each selected from methyl, ethyl, propyl, butyl, hexyl, octyl, decyl, cyclohexyl, phenyl, tolyl, xylyl, benzyl, phenylethyl, naphthyl, anthracenyl, phenanthracenyl, pyrenyl, napthacenyl, 9,10-benzophenanthrenyl, chrysenyl, 1,2-benzanthracenyl, 3,4-benzophenanthrenyl, 3,4-benzopyrene, perylenyl, 1,2,3,4-dibenzanthracenyl, 1,2,5,6-dibenzanthracenyl, 1,2,6,7-dibenzoanthracenyl, 1,2,7,8-dibenzanthracenyl, 1,2,6,7-dibenzophenanthracenyl, 1,2,7,8-dibenzophenanthracenyl, pentacenyl, picenyl, coronenyl, 1,2,4,5-dibenzopyrene, hexacenyl, phenylhexadecenyl, or anthracenylhexacenyl.
Claim 7
Dependent Claim 56 words
A composition according to claim 1, wherein the monovalent hydrocarbon or halohydrocarbon radicals free of aliphatic unsaturation having from 1 to 20 carbon atoms of R iii are independently selected from methyl, ethyl, propyl, butyl, hexyl, octyl, decyl, cyclohexyl, phenyl, tolyl, xylyl, benzyl, phenylethyl, naphthyl, anthracenyl, phenanthracenyl, pyrenyl, napthacenyl, 9,10-benzophenanthrenyl, chrysenyl, 1,2-benzanthracenyl, 3,4-benzophenanthrenyl, 3,4-benzopyrene, or perylenyl.
Claim 8
Dependent Claim 17 words
A composition according to claim 1, wherein the halogen atoms are selected from fluorine, chlorine, or bromine.
Claim 9
Dependent Claim 18 words
A composition according to claim 1, wherein the alkoxy radicals are selected from methoxy, ethoxy, propoxy, or butoxy.
Claim 10
Dependent Claim 31 words
A composition according to claim 1, wherein the hydrocarbon groups substituted with nitro groups are selected from 3--O 2 N--C 6 H 4 or 4--Cl,3--O 2 N--C 6 H 3 .
Claim 11
Dependent Claim 33 words
A composition according to claim 1, wherein the hydrocarbon groups substituted with nitrile groups are selected from 4--NC--C 6 H 4 , 1--NC--C 10 H 7 , or 2--NC--C 10 H 7 .
Claim 12
Dependent Claim 28 words
A composition according to claim 1, wherein the hydrocarbon groups substituted with carboxylic acid groups are selected from 4--HOOC--C 6 H 4 or 3--HOOC--C 6 H 4 .
Claim 13
Dependent Claim 32 words
A composition according to claim 1, wherein the hydrocarbon groups substituted with sulfonic acid groups are selected from 4--HO 3 S--C 6 H 4 or 3--HO 3 S--C 6 H 4 .
Claim 14
Dependent Claim 50 words
A composition according to claim 1, wherein the hydrocarbon groups substituted with alkoxy groups are selected from 4--CH 3 O--C 6 H 4 , 4--C 2 H 5 O--C 6 H 4 , 2--CH 3 O--C 6 H 4 , or 2--C 2 H 5 O--C 6 H 4 .
Claim 15
Dependent Claim 16 words
A composition according to claim 1, wherein the arylalkoxy radicals are selected from benzyloxy and phenylethyloxy.
Claim 16
Dependent Claim 16 words
A composition according to claim 1, wherein the aryloxy radicals are selected from phenoxy or napthoxy.
Claim 17
Dependent Claim 81 words
A composition according to claim 1, wherein X - is selected from perfluorobutanesulfonic acid anions, perfluoroethanesulfonic acid anions, perfluoro-octanesulfonic acid anions, trifluoromethanesulfonic acid anions, BF 4 - , BCl 4 - , BBr 4 - , B(C 6 F 5 ) 4 - , B(C 10 F 7 ) 4 - , B(O 3 SCF 3 ) 4 - , B(O 3 SC 2 F 5 ) 4 - , or B(O 3 SC 4 F 9 ) 4 - .
Claim 18
Dependent Claim 11 words
A composition according to claim 1, wherein X - is trifluoromethanesulfonate.
Claim 19
Dependent Claim 18 words
A composition according to claim 1, wherein Y - is selected from p-toluenesulfonate, 4-methylphenylsulfonate, benzenesulfonate, dodecylbenzenesulfonate, or 3-nitrobenzenesulfonate.
Claim 20
Dependent Claim 13 words
A composition according to claim 1, wherein x has a value of zero.
Claim 21
Dependent Claim 152 words
A composition according to claim 19, wherein the composition further comprises an organopolysiloxane having the general formula: ##STR10## wherein R 8 is a monovalent hydrocarbon radical having from 1 to 20 carbon atoms, R 9 is R 8 or is a group having its formula selected from the group consisting of (i) --OR 10 OCH═CH 2 and (ii) --R 10 Si(OR 10 OCH═CH 2 ) 3-h R 11 h wherein R 10 is a divalent hydrocarbon or halohydrocarbon radical having from 1 to 20 carbon atoms, h has a value of 0 to 2, R 11 is a monovalent hydrocarbon radical having from 1 to 20 carbon atoms, f has a value of 0 to 5000, g has a value of 0 to 800, with the proviso that at least one .tbd.SiOR 10 OCH═CH 2 or .tbd.SiR 10 Si(OR 10 OCH═CH 2 ) 3-h R 11 h group exists in each compound.
Claim 22
Dependent Claim 46 words
A composition according to claim 20, wherein R 8 is methyl, R 9 is a group having the formula --R 10 Si(OR 10 OCH═CH 2 ) 3 wherein each R 10 is independently selected from the group consisting of methylene, ethylene, propylene, butylene, hexylene, and cyclohexyldimethylene.
Claim 23
Dependent Claim 43 words
A composition according to claim 21, wherein y has a value of zero and R 1 is selected from methyl or a group having the formula --R 2 OCH═CH 2 wherein R 2 is selected from methylene, ethylene, propylene, butylene, hexylene, or cyclohexyldimethylene.
Claim 24
Dependent Claim 43 words
A composition according to claim 20, wherein y has a value of zero and R 1 is selected from methyl or a group having the formula --R 2 OCH═CH 2 wherein R 2 is selected from methylene, ethylene, propylene, butylene, hexylene, or cyclohexyldimethylene.
Claim 25
Dependent Claim 66 words
A composition according to claim 20, wherein the composition further comprises an organic vinyl ether compound having the general formula: (CH═CHOR.sup.3).sub.d CR.sup.4.sub.4-d wherein R 3 is a divalent hydrocarbon or halohydrocarbon radical having from 1 to 20 carbon atoms, R 4 is a monovalent hydrocarbon or halohydrocarbon radical having from 1 to 20 carbon atoms or hydrogen, and d has a value of 1 to 3.
Claim 26
Dependent Claim 66 words
A composition according to claim 1, wherein the composition further comprises an organic vinyl ether compound having the general formula: (CH═CHOR.sup.3).sub.d CR.sup.4.sub.4-d wherein R 3 is a divalent hydrocarbon or halohydrocarbon radical having from 1 to 20 carbon atoms, R 4 is a monovalent hydrocarbon or halohydrocarbon radical having from 1 to 20 carbon atoms or hydrogen, and d has a value of 1 to 3.

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USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 2000-01-14 2000-07-15 2001-01-14 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 2004-01-14 2004-07-15 2005-01-14 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2008-01-14 2008-07-15 2009-01-14 $7700.00 Window Closed / Lapsed

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