US5527936A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Hydrosilylation of unsaturated compounds
Assignee: Axalta Coating Systems IP Co LLC
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Filing: 1995-02-17
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Granted: 1996-06-18
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Expires: 2015-02-17
Abstract
Abstract A method for hydrosilylating an olefinically unsaturated compound comprising contacting the unsaturated compound with a source of silicon in the presence of an azo-containing free-radical catalyst, the hydrosilylated product being a useful crosslinking agent.
Inventors
- 👤 Hasan Dindi
- 👤 Basil Gregorovich
- 👤 Isidor Hazan
- 👤 Stuart Milligan
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 00:32
CPC Classifications
C; C07; C07F; C07F7/00; C07F7/02; C07F7/08; C07F7/18; C07F7/1804; C07F7/1872; C07F7/188; C07F7/12; C07F7/14
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
118 words
A method for hydrosilylating (i) an olefinically unsaturated compound comprising contacting the unsaturated compound with (ii) a source of silicon in the presence of (iii) an azo initiator; wherein (i) is selected from at least one member of the group, including their isomers: myrcene, ocimene, alloocimene, dipentene limonene, menthadiene, phellandrene, terpinene, terpinolene, isoterpinolene, carvone, citronellal, citral, 4-vinyl-1-cyclohexene, and norbornadiene; (ii) is selected from the group H.sub.j SiR.sub.k X.sub.1 wherein: R is independently selected from alkyl, alkoxy, aryl, aryloxy, cycloalkyl, hydrocarbyl, acyloxy, and oxysilyl; X is independently selected from halogen; j is independently 1 to 3; l and k are independently 0 to 3; and j+k+l=4. wherein at least 10 percent by weight of the hydrosilylated product is disilylated.
Claim 2
Independent Claim
118 words
A method for hydrosilylating (i) an olefinically unsaturated compound comprising contacting the unsaturated compound with (ii) a source of silicon in the presence of (iii) an azo initiator; wherein (i) is selected from at least one member of the group, including their isomers: myrcene, ocimene, alloocimene, dipentene limonene, menthadiene, phellandrene, terpinene, terpinolene, isoterpinolene, carvone, citronellal, citral, 4-vinyl-1-cyclohexene, and norbornadiene; (ii) is selected from the group H.sub.j SiR.sub.k X.sub.1 wherein: R is independently selected from alkyl, alkoxy, aryl, aryloxy, cycloalkyl, hydrocarbyl, acyloxy, and oxysilyl; X is independently selected from halogen; j is independently 1 to 3; l and k are independently 0 to 3; and j+k+l=4. wherein at least 10 percent by weight of the hydrosilylated product is disilylated.
Claim 3
Dependent Claim
15 words
A method according to claim 1 wherein (i) is selected from limonene, 4-vinyl-1-cyclohexene and norbornadiene.
Claim 4
Dependent Claim
10 words
A method according to claim 2 wherein (i) is limonene.
Claim 5
Dependent Claim
10 words
A method according to claim 3 wherein (ii) is trichlorosilane.
Claim 6
Dependent Claim
40 words
A method according to claim 1 wherein (iii) is selected from at least one member of the group: 2,2'-azobis(2,4-dimethylpentane nitrile) 2,2'-azobis(2-methylbutanenitrile) 1,1'-azobis(cyclohexanecarbonitrile) 2,2'-azobis(N,N'-dimethyleneisobutyramidine)dihydrochloride 2,2'-azobis(2-amidinopropane)dihydrochloride 2,2'-azobis(N,N'-dimethyleneisobutyramidine) 4,4'-azobis(4-cyanopentanoic acid) 2,2'-azobis(2-methyl-N-(1,1-bis(hydroxymethyl)-2-hydroxyethyl)propionamide) 2,2'-azobis(2-methyl-N-(1,1-bis(hydroxymethyl)ethyl)propionamide) 2,2'-azobis(2-methyl-N-(2-hydroxyethyl)propionamide) 2,2'-azobis(isobutyramide)dihydrate 2,2'-azobis(4-methoxy-2,4-dimethylvaleronitrile) 2,2'-azobisisobutyronitrile dimethyl 2,2'-azobisisobutyrate 2-(carbamoylazo)isobutyronitrile 2,2'-azobis(2,4,4-dimethylpentane) 2-phenylazo-2,4-dimethyl-4-methoxyvaleronitrile, and 2,2'-azobis(2-methylpropane).
Claim 7
Dependent Claim
14 words
A method according to claim 2 wherein (ii) is trichlorosilane and (iii) is azobis(2-methylbutanenitrile).
Claim 8
Dependent Claim
14 words
A method according to claim 2 wherein (ii) is trichlorosilane and (iii) is azobis(isobutyronitrile).
Claim 9
Dependent Claim
19 words
A method according to claim 1 comprising the additional step of reacting the hydrosilylated reaction product with an alcohol.
Claim 10
Dependent Claim
19 words
A method according to claim 2 comprising the additional step of reacting the hydrosilylated reaction product with an alcohol.
Claim 11
Dependent Claim
19 words
A method according to claim 3 comprising the additional step of reacting the hydrosilylated reaction product with an alcohol.
Claim 12
Dependent Claim
19 words
A method according to claim 4 comprising the additional step of reacting the hydrosilylated reaction product with an alcohol.
Claim 13
Dependent Claim
19 words
A method according to claim 5 comprising the additional step of reacting the hydrosilylated reaction product with an alcohol.
Claim 14
Dependent Claim
17 words
A method according to claim 8 wherein the alcohol is a C 1 to C 18 alcohol.
Claim 15
Dependent Claim
17 words
A method according to claim 9 wherein the alcohol is a C 1 to C 18 alcohol.
Claim 16
Dependent Claim
17 words
A method according to claim 10 wherein the alcohol is a C 1 to C 18 alcohol.
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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) | 1999-06-18 | 1999-12-18 | 2000-06-18 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2003-06-18 | 2003-12-18 | 2004-06-18 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2007-06-18 | 2007-12-18 | 2008-06-18 | $7700.00 | Window Closed / Lapsed |