US4151157A
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Polymer composite articles containing polysulfide silicon coupling agents
Assignee: OSI Specialties Inc
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Filing: 1977-06-28
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Granted: 1979-04-24
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Expires: 1997-06-28
Abstract
Abstract Polymer composites, such as rubber, thermostat and thermoplastic articles, comprising the reaction product of (a) an organic polymer, (b) an inorganic substrate and (c) a polysulfide silicon coupling agent, and articles comprising an inorganic substrate treated with a polysulfide silicon coupling agent.
Inventors
- 👤 Thomas C. Williams
- 👤 George E. Totten
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 20:50
CPC Classifications
C; C09; C09D; C09D183/00; C09D183/14; C07; C07F; C07F7/00; C07F7/02; C07F7/08; C07F7/18; C07F7/1804; C08; C08K; C08K5/00; C08K5/54; C08K5/548; C08K9/00; C08K9/04; C08K9/06; C01; C01P; C01P2004/00; C01P2004/10; C01P2004/20; C01P2004/80; C01P2006/00; C01P2006/20
Claims Analysis
Total Claims: 36
Claim 1
Independent Claim
286 words
A polymer composite article of manufacture comprising the reaction product of a composition comprising (a) an organic polymer, (b) an inorganic substrate and (c) a polysulfide silicon coupling agent selected from the class consisting of (i) polysulfide silanes having the formula ##STR28## wherein R' is hydrogen or a monovalent radical selected from the class consisting of hydrocarbon radicals and substituted hydrocarbon radicals; wherein X is a hydrolyzable radical selected from the class consisting of alkoxy, aryloxy, acyloxy, secondary amino and aminooxy radicals; wherein R is a divalent bridging group selected from the class consisting of hydrocarbon radicals, groups of the formula --R"OR"-- and groups of the formula --R"SR"-- wherein R" is a divalent hydrocarbon radical. wherein Q is an oxygen atom or a sulfur atom; wherein Z is a monovalent organic amino radical the nitrogen atom of which is directly bonded to the carbon atom of the (CH 2 ) group of the above formula; wherein n has a value of 0 or 1 and t has a value of 0 or 1, with the proviso that when n is 0, then t is 0; and wherein b has a value of 0 to 2, and x has a value of 2 to 4; (ii) polysulfide siloxane homopolymers consisting essentially of siloxy units having the formula ##STR29## wherein R', R, Q, Z, n, t, b and x are the same as defined above; and (iii) polysulfide siloxane copolymers consisting essentially of at least one siloxy unit represented by formula (II) above and at least one siloxy unit represented by the formula R'.sub.c SiO.sub.4-c/2 (III) wherein R' is the same as defined in formula (II) above, and wherein c has a value of 0 to 3 inclusive.
Claim 2
Dependent Claim
286 words
A polymer composite article of manufacture comprising the reaction product of a composition comprising (a) an organic polymer, (b) an inorganic substrate and (c) a polysulfide silicon coupling agent selected from the class consisting of (i) polysulfide silanes having the formula ##STR28## wherein R' is hydrogen or a monovalent radical selected from the class consisting of hydrocarbon radicals and substituted hydrocarbon radicals; wherein X is a hydrolyzable radical selected from the class consisting of alkoxy, aryloxy, acyloxy, secondary amino and aminooxy radicals; wherein R is a divalent bridging group selected from the class consisting of hydrocarbon radicals, groups of the formula --R"OR"-- and groups of the formula --R"SR"-- wherein R" is a divalent hydrocarbon radical. wherein Q is an oxygen atom or a sulfur atom; wherein Z is a monovalent organic amino radical the nitrogen atom of which is directly bonded to the carbon atom of the (CH 2 ) group of the above formula; wherein n has a value of 0 or 1 and t has a value of 0 or 1, with the proviso that when n is 0, then t is 0; and wherein b has a value of 0 to 2, and x has a value of 2 to 4; (ii) polysulfide siloxane homopolymers consisting essentially of siloxy units having the formula ##STR29## wherein R', R, Q, Z, n, t, b and x are the same as defined above; and (iii) polysulfide siloxane copolymers consisting essentially of at least one siloxy unit represented by formula (II) above and at least one siloxy unit represented by the formula R'.sub.c SiO.sub.4-c/2 (III) wherein R' is the same as defined in formula (II) above, and wherein c has a value of 0 to 3 inclusive.
Claim 3
Dependent Claim
40 words
An article of manufacture as defined in claim 1, wherein the organic polymer is selected from the class consisting of vulcanizable rubber polymers, thermoplastic forming resins and thermoset forming resins, and wherein the inorganic substrate is a siliceous reinforcing material.
Claim 4
Dependent Claim
34 words
A vulcanized rubber article of manufacture defined in claim 2, wherein the organic polymer is a vulcanizable rubber polymer and wherein the polysulfide silicon coupling agent is a polysulfide silane having the formula ##STR30##
Claim 5
Dependent Claim
139 words
A vulcanizable rubber article of manufacture as defined in claim 3, wherein R' is an alkyl radical, wherein X is an alkoxy radical, wherein R is an alkylene or alkyleneoxyalkylene radical, wherein n is 1, and t is 0, and wherein Z is an organic amino radical of the formula --NZ 1 Z 2 wherein Z 1 and Z 2 are taken individually and Z 1 is an organic radical selected from the class consisting of alkyl, aryl, aralkyl, alkaryl and haloaryl radicals; hydroxy substituted alkyl, aryl, aralkyl and alkaryl radicals; alkoxy substituted alkyl, aryl, aralkyl and alkaryl radicals; mercapto substituted alkyl, aryl, aralkyl and alkaryl radicals; amino substituted alkyl, aryl, aralkyl and alkaryl radicals; and hydrolyzable silyl substituted alkyl, aryl, aralkyl and alkaryl radicals; and wherein Z 2 is hydrogen or a Z 1 radical as defined above.
Claim 6
Dependent Claim
22 words
A vulcanized rubber article of manufacture as defined in claim 4, wherein b is 0 and wherein R is an alkyleneoxyalkylene radical.
Claim 7
Dependent Claim
24 words
A vulcanized rubber article of manufacture as defined in claim 5, wherein X is a methoxy radical and wherein R is a propyleneoxymethylene radical.
Claim 8
Dependent Claim
41 words
A vulcanized rubber article of manufacture as defined in claim 2, wherein the organic polymer is a vulcanizable rubber polymer and wherein the polysulfide silicon coupling agent is a polysulfide siloxane homopolymer consisting essentially of siloxy units having the formula ##STR31##
Claim 9
Dependent Claim
34 words
A vulcanized rubber article of manufacture as defined in claim 7, wherein R' is an alkyl radical, wherein R is an alkylene or alkyleneoxyalkylene radical, and wherein n is 1 and t is 0.
Claim 10
Dependent Claim
117 words
A vulcanized rubber article of manufacture as defined in claim 8, wherein R is a propyleneoxymethylene radical and wherein Z is an organic amino radical of the formula --NZ 1 Z 2 wherein Z 1 and Z 2 are taken individually and Z 1 is an organic radical selected from the class consisting of alkyl, aryl, aralkyl, alkaryl and haloaryl radicals; hydroxy substituted alkyl, aryl, aralkyl and alkaryl radicals; alkoxy substituted alkyl, aryl, aralkyl and alkaryl radicals; mercapto substituted alkyl, aryl, aralkyl and alkaryl radicals; amino substituted alkyl, aryl, aralkyl and alkaryl radicals; and hydrolyzable silyl substituted alkyl, aryl, aralkyl and alkaryl radicals; and wherein Z 2 is hydrogen or a Z 1 radical as defined above.
Claim 11
Dependent Claim
56 words
A vulcanized rubber article of manufacture as defined in claim 2, wherein the organic polymer is a vulcanizable rubber polymer and wherein the polysulfide silicon coupling agent is a polysulfide siloxane copolymer consisting essentially of at least one siloxy unit of the formula ##STR32## and at least one siloxy unit represented by the formula R'.sub.c SiO.sub.4-c/2.
Claim 12
Dependent Claim
35 words
A vulcanized rubber article of manufacture as defined in claim 10, wherein R' is a monovalent hydrocarbon radical, wherein R is an alkylene or alkyleneoxyalkylene radical and wherein n is 1, and t is 0.
Claim 13
Dependent Claim
123 words
A vulcanized rubber article of manufacture as defined in claim 11, wherein R' is an alkyl radical, wherein R is a propyleneoxymethylene radical and wherein Z is an organic amino radical of the formula --NZ 1 Z 2 wherein Z 1 and Z 2 are taken individually and Z 1 is an organic radical selected from the class consisting of alkyl, aryl, aralkyl, alkaryl, and haloaryl radicals; hydroxy substituted alkyl, aryl, aralkyl and alkaryl radicals; alkoxy substituted alkyl, aryl, aralkyl and alkaryl radicals; mercapto substituted alkyl, aryl, aralkyl and alkaryl radicals; amino substituted alkyl, aryl, aralkyl and alkaryl radicals; and hydrolyzable silyl substituted alkyl, aryl, aralkyl and alkaryl radicals; and wherein Z 2 is hydrogen or a Z 1 radical as defined above.
Claim 14
Dependent Claim
35 words
A thermoplastic resin article of manufacture as defined in claim 2, wherein the organic polymer is a thermoplastic forming resin and wherein the polysulfide silicon coupling agent is a polysulfide silane having the formula ##STR33##
Claim 15
Dependent Claim
140 words
A thermoplastic resin article of manufacture as defined in claim 13, wherein R' is an alkyl radical, wherein X is an alkoxy radical, wherein R is an alkylene or alkyleneoxyalkylene radical, wherein n is 1, and t is 0, and wherein Z is an organic amino radical of the formula --NZ 1 Z 2 , wherein Z 1 and Z 2 are taken individually and Z 1 is an organic radical selected from the class consisting of alkyl, aryl, aralkyl, alkaryl and haloaryl radicals; hydroxy substituted alkyl, aryl, aralkyl and alkaryl radicals; alkoxy substituted alkyl, aryl, aralkyl and alkaryl radicals; mercapto substituted alkyl, aryl, aralkyl and alkaryl radicals; amino substituted alkyl, aryl, aralkyl and alkaryl radicals; and hydrolyzable silyl substituted alkyl, aryl, aralkyl and alkaryl radicals; and wherein Z 2 is hydrogen or a Z 1 radical as defined above.
Claim 16
Dependent Claim
22 words
A thermoplastic resin article of manufacture as defined in claim 14, wherein b is 0, and wherein R is an alkyleneoxyalkylene radical.
Claim 17
Dependent Claim
24 words
A thermoplastic resin article of manufacture as defined in claim 15, wherein X is a methoxy radical and wherein R is a propyleneoxymethylene radical.
Claim 18
Dependent Claim
41 words
A thermoplastic resin article of manufacture as defined in claim 2, wherein the organic polymer is a thermoplastic forming resin and wherein the polysulfide silicon coupling agent is a polysulfide siloxane homopolymer consisting essentially of siloxy units having the formula ##STR34##
Claim 19
Dependent Claim
26 words
A thermoplastic resin article of manufacture as defined in claim 17, wherein R' is an alkyl radical and wherein n is 1, and t is 0.
Claim 20
Dependent Claim
118 words
A thermoplastic resin article of manufacture as defined in claim 18, wherein R is a propyleneoxymethylene radical and wherein Z is an organic amino radical of the formula --NZ 1 Z 2 , wherein Z 1 and Z 2 are taken individually and Z 1 is an organic radical selected from the class consisting of alkyl, aryl, aralkyl, alkaryl and haloaryl radicals; hydroxy substituted alkyl, aryl, aralkyl and alkaryl radicals; alkoxy substituted alkyl, aryl, aralkyl and alkaryl radicals; mercapto substituted alkyl, aryl, aralkyl and alkaryl radicals; amino substituted alkyl, aryl, aralkyl and alkaryl radicals; and hydrolyzable silyl substituted alkyl, aryl, aralkyl and alkaryl radicals; and wherein Z 2 is hydrogen or a Z 1 radical as defined above.
Claim 21
Dependent Claim
56 words
A thermoplastic resin article of manufacture as defined in claim 2, wherein the organic polymer is a thermoplastic forming resin and wherein the polysulfide silicon coupling agent is a polysulfide siloxane copolymer consisting essentially of at least one siloxy unit of the formula ##STR35## and at least one siloxy unit represented by the formula R'.sub.c SiO.sub.4-c/2.
Claim 22
Dependent Claim
35 words
A thermoplastic resin article of manufacture as defined in claim 20, wherein R' is a monovalent hydrocarbon radical, wherein R is an alkylene or alkyleneoxyalkylene radical, and wherein n is 1, and t is 0.
Claim 23
Dependent Claim
123 words
A thermoplastic resin article of manufacture as defined in claim 21, wherein R' is an alkyl radical, wherein R is a propyleneoxymethylene radical and wherein Z is an organic amino radical of the formula --NZ 1 Z 2 wherein Z 1 and Z 2 are taken individually and Z 1 is an organic radical selected from the class consisting of alkyl, aryl, aralkyl, alkaryl and haloaryl radicals; hydroxy substituted alkyl, aryl, aralkyl and alkaryl radicals; alkoxy substituted alkyl, aryl, aralkyl and alkaryl radicals; mercapto substituted alkyl, aryl, aralkyl and alkaryl radicals; amino substituted alkyl, aryl, aralkyl and alkaryl radicals; and hydrolyzable silyl substituted alkyl, aryl, aralkyl and alkaryl radicals; and wherein Z 2 is hydrogen or a Z 1 radical as defined above.
Claim 24
Dependent Claim
35 words
A thermoset resin article of manufacture as defined in claim 2, wherein the organic polymer is a thermoset forming resin and wherein the polysulfide silicon coupling agent is a polysulfide silane having the formula ##STR36##
Claim 25
Dependent Claim
139 words
A thermoset resin article of manufacture as defined in claim 23, wherein R' is an alkyl radical, wherein X is an alkoxy radical, wherein R is an alkylene or alkyleneoxyalkylene radical, wherein n is 1, and t is 0, and wherein Z is an organic amino radical of the formula --NZ 1 Z 2 wherein Z 1 and Z 2 are taken individually and Z 1 is an organic radical selected from the class consisting of alkyl, aryl, aralkyl, alkaryl and haloaryl radicals; hydroxy substituted alkyl, aryl, aralkyl and alkaryl radicals; alkoxy substituted alkyl, aryl, aralkyl and alkaryl radicals; mercapto substituted alkyl, aryl, aralkyl and alkaryl radicals; amino substituted alkyl, aryl, aralkyl and alkaryl radicals, and hydrolyzable silyl substituted alkyl, aryl, aralkyl and alkaryl radicals; and wherein Z 2 is hydrogen or a Z 1 radical as defined above.
Claim 26
Dependent Claim
22 words
A thermoset resin article of manufacture as defined in claim 24, wherein b is 0 and wherein R is an alkyleneoxyalkylene radical.
Claim 27
Dependent Claim
24 words
A thermoset resin article of manufacture as defined in claim 25, wherein X is a methoxy radical and wherein R is a propyleneoxymethylene radical.
Claim 28
Dependent Claim
41 words
A thermoset resin article of manufacture as defined in claim 2, wherein the organic polymer is a thermoset forming resin and wherein the polysulfide silicon coupling agent is a polysulfide siloxane homopolymer consisting essentially of siloxy units having the formula ##STR37##
Claim 29
Dependent Claim
26 words
A thermoset resin article of manufacture as defined in claim 27, wherein R' is an alkyl radical and wherein n is 1 and t is 0.
Claim 30
Dependent Claim
117 words
A thermoset resin article of manufacture as defined in claim 28, wherein R is a propyleneoxymethylene radical and wherein Z is an organic amino radical of the formula --NZ 1 Z 2 wherein Z 1 and Z 2 are taken individually and Z 1 is an organic radical selected from the class consisting of alkyl, aryl, aralkyl, alkaryl and haloaryl radicals; hydroxy substituted alkyl, aryl, aralkyl and alkaryl radicals; alkoxy substituted alkyl, aryl, aralkyl and alkaryl radicals; mercapto substituted alkyl, aryl, aralkyl and alkaryl radicals; amino substituted alkyl, aryl, aralkyl and alkaryl radicals; and hydrolyzable silyl substituted alkyl, aryl, aralkyl and alkaryl radicals; and wherein Z 2 is hydrogen or a Z 1 radical as defined above.
Claim 31
Dependent Claim
56 words
A thermoset resin article of manufacture as defined in claim 2, wherein the organic polymer is a thermoset forming resin and wherein the polysulfide silicon coupling agent is a polysulfide siloxane copolymer consisting essentially of at least one siloxy unit of the formula ##STR38## and at least one siloxy unit represented by the formula R'.sub.c SiO.sub.4-c/2.
Claim 32
Dependent Claim
35 words
A thermoset resin article of manufacture as defined in claim 30, wherein R' is a monovalent hydrocarbon radical, wherein R is an alkylene or alkyleneoxyalkylene radical, and wherein n is 1, and t is 0.
Claim 33
Dependent Claim
123 words
A thermoset resin article of manufacture as defined in claim 31, wherein R' is an alkyl radical, wherein R is a propyleneoxymethylene radical and wherein Z is an organic amino radical of the formula --NZ 1 Z 2 wherein Z 1 and Z 2 are taken individually and Z 1 is an organic radical selected from the class consisting of alkyl, aryl, aralkyl, alkaryl and haloaryl radicals; hydroxy substituted alkyl, aryl, aralkyl, and alkaryl radicals; alkoxy substituted alkyl, aryl, aralkyl and alkaryl radicals; mercapto substituted alkyl, aryl, aralkyl and alkaryl radicals; amino substituted alkyl, aryl, aralkyl and alkaryl radicals; and hydrolyzable silyl substituted alkyl, aryl, aralkyl and alkaryl radicals; and wherein Z 2 is hydrogen or a Z 1 radical as defined above.
Claim 34
Dependent Claim
29 words
An article of manufacture as defined in claim 2, wherein the siliceous reinforcing material is selected from the class consisting of silica fillers, metal silicate fillers and glass fibers.
Claim 35
Dependent Claim
24 words
An article of manufacture as defined in claim 2, wherein the polysulfide silicon coupling agent is employed in the form of a solubilized solution.
Claim 36
Dependent Claim
24 words
An article of manufacture as defined in claim 2, wherein the polysulfide silicon coupling agent is employed in the form of an aqueous composition.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1982-04-23 | 1982-10-23 | 1983-04-24 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-04-23 | 1986-10-23 | 1987-04-24 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-04-23 | 1990-10-23 | 1991-04-24 | $7700.00 | Window Closed / Lapsed |