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US4156677A
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Polymer composite articles containing amino substituted mercapto organo silicon coupling agents
Assignee: OSI Specialties Inc
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Filing: 1977-06-28
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Granted: 1979-05-29
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Expires: 1997-06-28
Abstract
Abstract Polymer composites, such as rubber, thermoset and thermoplastic articles, comprising the reaction product of (a) an organic polymer, (b) an inorganic substrate and (c) an amino substituted mercapto organosilicon coupling agent, and articles comprising an inorganic substrate treated with an amino substituted mercapto organosilicon coupling agent.
Inventors
- 👤 Thomas C. Williams
- 👤 George E. Totten
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 23:17
CPC Classifications
C; C09; C09D; C09D183/00; C09D183/04; C09D183/08; C07; C07F; C07F7/00; C07F7/02; C07F7/08; C07F7/18; C07F7/1804; C08; C08K; C08K3/00; C08K3/34; C08K3/36; C08K5/00; C08K5/54; C08K5/544; C08K5/548; C08K9/00; C08K9/04; C08K9/06; C08K5/0008; C08K5/0016; Y; Y10; Y10S; Y10S524/00; Y10S524/925
Claims Analysis
Total Claims: 54
Claim 1
Independent Claim
305 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) an amino substituted mercapto organosilicon coupling agent selected from the class consisting of (i) amino substituted mercapto organosilanes having the formula ##STR29## wherein R' is a monovalent hydrocarbon radical selected from the class consisting of hydrogen, 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; wherein a has a value of 1 to 3 and b has a value of 0 to 2, with the proviso that the sum of (a+b) is not greater than 3; (ii) amino substituted mercapto organosiloxane homopolymers consisting essentially of siloxy units having the formula ##STR30## wherein R', R, Q, Z, n, t, a and b are the same as defined above; and (iii) amino substituted mercapto organosiloxane copolymers consisting essentially of at least one siloxy unit represented by formula (II) above and at least one siloxy unit represented by the formula ##STR31## wherein R' is the same as defined in formula (II) above and wherein c has a value of from 0 to 3 inclusive.
Claim 2
Dependent Claim
305 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) an amino substituted mercapto organosilicon coupling agent selected from the class consisting of (i) amino substituted mercapto organosilanes having the formula ##STR29## wherein R' is a monovalent hydrocarbon radical selected from the class consisting of hydrogen, 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; wherein a has a value of 1 to 3 and b has a value of 0 to 2, with the proviso that the sum of (a+b) is not greater than 3; (ii) amino substituted mercapto organosiloxane homopolymers consisting essentially of siloxy units having the formula ##STR30## wherein R', R, Q, Z, n, t, a and b are the same as defined above; and (iii) amino substituted mercapto organosiloxane copolymers consisting essentially of at least one siloxy unit represented by formula (II) above and at least one siloxy unit represented by the formula ##STR31## wherein R' is the same as defined in formula (II) above and wherein c has a value of from 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
36 words
A vulcanized rubber article of manufacture as defined in claim 2, wherein the organic polymer is a vulcanizable rubber polymer and wherein the organosilicon coupling agent is an amino substituted mercapto organosilane having the formula ##STR32##
Claim 5
Dependent Claim
43 words
A vulcanized 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 and wherein n is 1, t is 0 and a is 1.
Claim 6
Dependent Claim
112 words
A vulcanized rubber article of manufacture as defined in claim 4, wherein b is 0 and Z is an organic amino radical of the formula --NZ.sup.1 Z.sup.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 radical; 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 7
Dependent Claim
33 words
A vulcanized rubber article of manufacture as defined in claim 5, wherein X is methoxy or ethoxy, R is a propyleneoxymethylene radical, Z 1 is alkyl or aralkyl and Z 2 is hydrogen.
Claim 8
Dependent Claim
18 words
A vulcanized rubber article of manufacture as defined in claim 6, wherein Z 1 is a p-toluidinyl radical.
Claim 9
Dependent Claim
42 words
A vulcanized rubber article of manufacture as defined in claim 2, wherein the organic polymer is a vulcanizable rubber polymer and wherein the organosilicon coupling agent is an amino substituted mercapto organosiloxane homopolymer consisting essentially of siloxy units of the formula ##STR33##
Claim 10
Dependent Claim
34 words
A vulcanized rubber article of manufacture as defined in claim 8, wherein R' is an alkyl radical, wherein R is an alkylene or alkyleneoxyalkylene radical and wherein n is 1 and t is 0.
Claim 11
Dependent Claim
114 words
A vulcanized rubber article of manufacture as defined in claim 9, wherein R is a propyleneoxymethylene radical and Z is an organic amino radical of the formula --NZ.sup.1 Z.sup.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 12
Dependent Claim
25 words
A vulcanized rubber article of manufacture as defined in claim 10, wherein Z 1 is an alkyl or aralkyl radical and Z 2 is hydrogen.
Claim 13
Dependent Claim
18 words
A vulcanized rubber article of manufacture as defined in claim 11, wherein Z 1 is a p-toluidinyl radical.
Claim 14
Dependent Claim
55 words
A vulcanized rubber article of manufacture as defined in claim 2, wherein the organic polymer is a vulcanizable rubber polymer and wherein the organosilicon coupling agent is an amino substituted mercapto organosiloxane copolymer consisting essentially of at least one siloxy unit of the formula ##STR34## and at least one siloxy unit of the formula ##STR35##
Claim 15
Dependent Claim
38 words
A vulcanized rubber article of manufacture as defined in claim 13 wherein R' is a monovalent hydrocarbon radical, wherein R is an alkylene or alkyleneoxyalkylene radical, and wherein n is 1, t is 0 and a is 1.
Claim 16
Dependent Claim
17 words
A vulcanized rubber article of manufacture as defined in claim 14, wherein R' is an alkyl radical.
Claim 17
Dependent Claim
115 words
A vulcanized rubber article of manufacture as defined in claim 15, wherein R is a propyleneoxymethylene radical and wherein Z is an organic amino radical of the formula --NZ.sup.1 Z.sup.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 18
Dependent Claim
25 words
A vulcanized rubber article of manufacture as defined in claim 16, wherein Z 2 is hydrogen and Z 1 is an alkyl or aralkyl radical.
Claim 19
Dependent Claim
18 words
A vulcanized rubber article of manufacture as defined in claim 17, wherein Z 1 is a p-toluidinyl radical.
Claim 20
Dependent Claim
36 words
A thermoplastic resin article of manufacture as defined in claim 2, wherein the organic polymer is a thermoplastic forming resin and wherein the organosilicon coupling agent is an amino substituted mercapto organosilane having the formula ##STR36##
Claim 21
Dependent Claim
43 words
A thermoplastic resin article of manufacture as defined in claim 19, wherein R' is an alkyl radical, wherein X is an alkoxy radical, wherein R is an alkylene or alkyleneoxyalkylene radical, and wherein n is 1, t is 0 and a is 1.
Claim 22
Dependent Claim
112 words
A thermoplastic resin article of manufacture as defined in claim 20, wherein b is 0 and Z is an organic amino radical of the formula --NZ.sup.1 Z.sup.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 radial as defined above.
Claim 23
Dependent Claim
33 words
A thermoplastic resin article of manufacture as defined in claim 21, wherein X is methoxy or ethoxy, R is a propyleneoxymethylene radical, Z 1 is alkyl or aralkyl and Z 2 is hydrogen.
Claim 24
Dependent Claim
18 words
A thermoplastic resin article of manufacture as defined in claim 1, wherein Z 1 is a p-toluidinyl radical.
Claim 25
Dependent Claim
42 words
A thermoplastic resin article of manufacture as defined in claim 2, wherein the organic polymer is a thermoplastic forming resin and wherein the organosilicon coupling agent is an amino substituted mercapto organosiloxane homopolymer consisting essentially of siloxy units of the formula ##STR37##
Claim 26
Dependent Claim
34 words
A thermoplastic resin article of manufacture as defined in claim 24, wherein R' is an alkyl radical, wherein R is an alkylene or alkyleneoxyalkylene radical and wherein n is 1 and t is 0.
Claim 27
Dependent Claim
114 words
A thermoplastic resin article of manufacture as defined in claim 25, wherein R is a propyleneoxymethylene radical and Z is an organic amino radical of the formula --NZ.sup.1 Z.sup.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 28
Dependent Claim
25 words
A thermoplastic resin article of manufacture as defined in claim 26, wherein Z 1 is an alkyl or aralkyl radical and Z 2 is hydrogen.
Claim 29
Dependent Claim
18 words
A thermoplastic resin article of manufacture as defined in claim 27, wherein Z 1 is a p-toluidinyl radical.
Claim 30
Dependent Claim
55 words
A thermoplastic resin article of manufacture as defined in claim 2, wherein the organic polymer is a thermoplastic forming resin and wherein the organosilicon coupling agent is an amino substituted mercapto organosiloxane copolymer consisting essentially of at least one siloxy unit of the formula. ##STR38## and at least one siloxy unit of the formula ##STR39##
Claim 31
Dependent Claim
38 words
A thermoplastic resin article of manufacture as defined in claim 29, wherein R' is a monovalent hydrocarbon radical, wherein R is an alkylene or alkyleneoxyalkylene radical, and wherein n is 1, t is 0 and a is 1.
Claim 32
Dependent Claim
17 words
A thermoplastic resin article of manufacture as defined in claim 30, wherein R' is an alkyl radical.
Claim 33
Dependent Claim
115 words
A thermoplastic resin article of manufacture as defined in claim 31, wherein R is a propyleneoxymethylene radical and wherein Z is an organic amino radical of the formula --NZ.sup.1 Z.sup.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
25 words
A thermoplastic resin article of manufacture as defined in claim 32, wherein Z 2 is hydrogen and Z 1 is an alkyl or aralkyl radical.
Claim 35
Dependent Claim
19 words
A thermoplastic resin organosiloxane article of manufacture as defined in claim 33, wherein Z 1 is a p-toluidinyl radical.
Claim 36
Dependent Claim
36 words
A thermoset resin article of manufacture as defined in claim 2, wherein the organic polymer is a thermoset forming resin and wherein the organosilicon coupling agent is an amino substituted mercapto organosilane having the formula ##STR40##
Claim 37
Dependent Claim
43 words
A thermoset resin article of manufacture as defined in claim 35, wherein R' is an alkyl radical, wherein X is an alkoxy radical, wherein R is an alkylene or alkyleneoxyalkylene radical, and wherein n is 1, t is 0 and a is 1.
Claim 38
Dependent Claim
112 words
A thermoset resin article of manufacture as defined in claim 36, wherein b is 0 and Z is an organic amino radical of the formula --NZ.sup.1 Z.sup.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 39
Dependent Claim
33 words
A thermoset resin article of manufacture as defined in claim 37, wherein X is methoxy or ethoxy, R is a propyleneoxymethylene radical, Z 1 is alkyl or aralkyl and Z 2 is hydrogen.
Claim 40
Dependent Claim
18 words
A thermoset resin article of manufacture as defined in claim 38, wherein Z 1 is a p-toluidinyl radical.
Claim 41
Dependent Claim
42 words
A thermoset resin article of manufacture as defined in claim 2, wherein the organic polymer is a thermoset forming resin and wherein the organosilicon coupling agent is an amino substituted mercapto organosiloxane homopolymer consisting essentially of siloxy units of the formula ##STR41##
Claim 42
Dependent Claim
34 words
A thermoset resin article of manufacture as defined in claim 40, wherein R' is an alkyl radical, wherein R is an alkylene or alkyleneoxyalkylene radical and wherein n is 1 and t is 0.
Claim 43
Dependent Claim
114 words
A thermoset resin article of manufacture as defined in claim 41, wherein R is a propyleneoxymethylene radical and Z is an organic amino radical of the formula --NZ.sup.1 Z.sup.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 44
Dependent Claim
25 words
A thermoset resin article of manufacture as defined in claim 42, wherein Z 1 is an alkyl or aralkyl radical and Z 2 is hydrogen.
Claim 45
Dependent Claim
18 words
A thermoset resin article of manufacture as defined in claim 43, wherein Z 1 is a p-toluidinyl radical.
Claim 46
Dependent Claim
55 words
A thermoset resin article of manufacture as defined in claim 2, wherein the organic polymer is a thermoset forming resin and wherein the organosilicon coupling agent is an amino substituted mercapto organosiloxane copolymer consisting essentially of at least one siloxy unit of the formula ##STR42## and at least one siloxy unit of the formula ##STR43##
Claim 47
Dependent Claim
38 words
A thermoset resin article of manufacture as defined in claim 45, wherein R' is a monovalent hydrocarbon radical, wherein R is an alkylene or alkyleneoxyalkylene radical, and wherein n is 1, t is 0 and a is 1.
Claim 48
Dependent Claim
17 words
A thermoset resin article of manufacture as defined in claim 46, wherein R' is an alkyl radical.
Claim 49
Dependent Claim
115 words
A thermoset resin article of manufacture as defined in claim 47, wherein R is a propyleneoxymethylene radical and wherein Z is an organic amino radical of the formula --NZ.sup.1 Z.sup.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 50
Dependent Claim
25 words
A thermoset resin article of manufacture as defined in claim 48, wherein Z 2 is hydrogen and Z 1 is an alkyl or aralkyl radical.
Claim 51
Dependent Claim
18 words
A thermoset resin article of manufacture as defined in claim 49, wherein Z 1 is a p-toluidinyl radical.
Claim 52
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 53
Dependent Claim
26 words
An article of manufacture as defined in claim 2, wherein the amino substituted mercapto organosilicon coupling agent is employed in the form of a solubilized solution.
Claim 54
Dependent Claim
26 words
An article of manufacture as defined in claim 2, wherein the amino substituted mercapto organosilicon 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) | 1982-05-28 | 1982-11-27 | 1983-05-29 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-05-28 | 1986-11-27 | 1987-05-29 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-05-28 | 1990-11-27 | 1991-05-29 | $7700.00 | Window Closed / Lapsed |