US4381396A
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US
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Silynorbornane anhydrides and method for making
Assignee: General Electric Co
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Filing: 1982-07-07
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Granted: 1983-04-26
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Expires: 2002-07-07
Abstract
Abstract Silylnorbornane anhydrides are provided by effecting reaction between a silicon hydride and a norbornene carboxylic acid anhydride in the presence of a platinum catalyst. The resulting silicon functionalized norbornane monoanhydrides or dianhydrides can be used to synthesize a variety of tough organosilicon polyimide copolymers and polydiorganosiloxane polyimide block polymers.
Inventors
- 👤 Hong-Son Ryang
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 06:19
CPC Classifications
C; C08; C08G; C08G77/00; C08G77/04; C08G77/38; C07; C07F; C07F7/00; C07F7/02; C07F7/08; C07F7/0803; C07F7/081; C07F7/0812; C07F7/0814; C07F7/0834; C07F7/0836; C07F7/0838; C07F7/10; C07F7/12; C07F7/14; C07F7/18; C07F7/1804; C07F7/1896; C08G73/00; C08G73/06; C08G73/10; C08G73/1057; C08G73/106; C08G77/14
Claims Analysis
Total Claims: 36
Claim 1
Independent Claim
194 words
Silylnorbornane anhydrides of the formula ##STR16## where R-R 5 are members selected from hydrogen, halogen, C.sub.(1-13) monovalent hydrocarbon radicals and substituted monovalent hydrocarbon radicals, Z is selected from --O-- and C--(R) 2 , R 6 is a member selected from monovalent hydrocarbon radicals and substituted monovalent hydrocarbon radicals, and X is a member selected from the class consisting of, (a) a hydrolyzable radical selected from the class consisting of halo, hydrogen, C.sub.(1-8) alkoxy, acyloxy, --N(R 7 ) 2 , cyano, hydrogen, amido, carbamato, enoxy, imidato, isocyanato, oximato, isocyanate, oximato, thioisocyanato and ureido, (b) siloxanes having the formula, ##EQU2## (c) polysiloxanes having the formula, ##STR17## R 7 is selected from monovalent hydrocarbon radicals and Y is selected from a radical having the formula, ##STR18## and (a) radicals, Y 1 is selected from R 6 radicals, Y radicals and mixtures thereof, a is a whole number equal to 0 to 3 inclusive, b is a whole number equal to 0 to 3 inclusive; c is a whole number equal to 0 to 3 inclusive, the sum of b+c is equal to 0 to 3 inclusive and n is an integer equal to 1 to 2000 inclusive.
Claim 2
Dependent Claim
194 words
Silylnorbornane anhydrides of the formula ##STR16## where R-R 5 are members selected from hydrogen, halogen, C.sub.(1-13) monovalent hydrocarbon radicals and substituted monovalent hydrocarbon radicals, Z is selected from --O-- and C--(R) 2 , R 6 is a member selected from monovalent hydrocarbon radicals and substituted monovalent hydrocarbon radicals, and X is a member selected from the class consisting of, (a) a hydrolyzable radical selected from the class consisting of halo, hydrogen, C.sub.(1-8) alkoxy, acyloxy, --N(R 7 ) 2 , cyano, hydrogen, amido, carbamato, enoxy, imidato, isocyanato, oximato, isocyanate, oximato, thioisocyanato and ureido, (b) siloxanes having the formula, ##EQU2## (c) polysiloxanes having the formula, ##STR17## R 7 is selected from monovalent hydrocarbon radicals and Y is selected from a radical having the formula, ##STR18## and (a) radicals, Y 1 is selected from R 6 radicals, Y radicals and mixtures thereof, a is a whole number equal to 0 to 3 inclusive, b is a whole number equal to 0 to 3 inclusive; c is a whole number equal to 0 to 3 inclusive, the sum of b+c is equal to 0 to 3 inclusive and n is an integer equal to 1 to 2000 inclusive.
Claim 3
Dependent Claim
101 words
Monoanhydrides of the formula, ##STR19## where R-R 5 are are a members selected from hydrogen, halogen, C.sub.(1-13) monovalent hydrocarbon radical and substituted C.sub.(1-13) monovalent hydrocarbon radicals, R 6 is a member selected from C.sub.(6-13) monovalent hydrocarbon radicals, and substituted C.sub.(6-13) monovalent hydrocarbon radicals, X is a hydrolyzable radical selected from halo, hydrogen, C.sub.(1-8) alkoxy, acyloxy, --N(R 7 ) 2 , cyano, hydrogen, amido, carbamato, enoxy, imidato, isocyanato, oximato, isocyanate, oximato, thioisocyanato and ureido, R 7 is selected from monovalent hydrocarbon radicals Z is selected from --O--and C--(R) 2 , and a is a whole number equal to 0 to 3 inclusive.
Claim 4
Dependent Claim
101 words
Monoanhydrides of the formula, ##STR19## where R-R 5 are are a members selected from hydrogen, halogen, C.sub.(1-13) monovalent hydrocarbon radical and substituted C.sub.(1-13) monovalent hydrocarbon radicals, R 6 is a member selected from C.sub.(6-13) monovalent hydrocarbon radicals, and substituted C.sub.(6-13) monovalent hydrocarbon radicals, X is a hydrolyzable radical selected from halo, hydrogen, C.sub.(1-8) alkoxy, acyloxy, --N(R 7 ) 2 , cyano, hydrogen, amido, carbamato, enoxy, imidato, isocyanato, oximato, isocyanate, oximato, thioisocyanato and ureido, R 7 is selected from monovalent hydrocarbon radicals Z is selected from --O--and C--(R) 2 , and a is a whole number equal to 0 to 3 inclusive.
Claim 5
Dependent Claim
3 words
The compound ##STR20##
Claim 6
Dependent Claim
3 words
The compound ##STR20##
Claim 7
Dependent Claim
3 words
The compound ##STR21##
Claim 8
Dependent Claim
3 words
The compound ##STR21##
Claim 9
Dependent Claim
3 words
The compound ##STR22##
Claim 10
Dependent Claim
3 words
The compound ##STR22##
Claim 11
Dependent Claim
3 words
The compound ##STR23##
Claim 12
Dependent Claim
3 words
The compound ##STR23##
Claim 13
Dependent Claim
3 words
The compound ##STR24##
Claim 14
Dependent Claim
3 words
The compound ##STR24##
Claim 15
Dependent Claim
3 words
The compound ##STR25##
Claim 16
Dependent Claim
3 words
The compound ##STR25##
Claim 17
Dependent Claim
3 words
The compound ##STR26##
Claim 18
Dependent Claim
3 words
The compound ##STR26##
Claim 19
Dependent Claim
3 words
The compound ##STR27##
Claim 20
Dependent Claim
3 words
The compound ##STR27##
Claim 21
Dependent Claim
3 words
The compound ##STR28##
Claim 22
Dependent Claim
3 words
The compound ##STR28##
Claim 23
Dependent Claim
50 words
Dianhydrides of the formula, ##STR29## where R-R 5 is selected from hydrogen, halogen, C.sub.(1-13) monovalent hydrocarbon radical and substituted C.sub.(1-13) monovalent hydrocarbon radicals, R 6 is a member selected from C.sub.(1-13) monovalent hydrocarbon radicals and substituted C.sub.(1-13) monovalent hydrocarbon radicals and Z is selected from --O-- and --C(R) 2 --.
Claim 24
Dependent Claim
50 words
Dianhydrides of the formula, ##STR29## where R-R 5 is selected from hydrogen, halogen, C.sub.(1-13) monovalent hydrocarbon radical and substituted C.sub.(1-13) monovalent hydrocarbon radicals, R 6 is a member selected from C.sub.(1-13) monovalent hydrocarbon radicals and substituted C.sub.(1-13) monovalent hydrocarbon radicals and Z is selected from --O-- and --C(R) 2 --.
Claim 25
Dependent Claim
3 words
The compound ##STR30##
Claim 26
Dependent Claim
3 words
The compound ##STR30##
Claim 27
Dependent Claim
60 words
Dianhydride terminated polydiorganosiloxanes of the formula, ##STR31## where R-R 5 are selected from hydrogen halogen, C.sub.(1-13) monovalent hydrocarbon radicals and substituted C.sub.(1-13) monovalent hydrocarbon radicals, R 6 is selected from C.sub.(1-13) monovalent hydrocarbon radicals and substituted C.sub.(1-13) monovalent hydrocarbon radicals, Z is selected from --O-- and --C(R) 2 --, and n is an integer equal to 1 to 2000 inclusive.
Claim 28
Dependent Claim
60 words
Dianhydride terminated polydiorganosiloxanes of the formula, ##STR31## where R-R 5 are selected from hydrogen halogen, C.sub.(1-13) monovalent hydrocarbon radicals and substituted C.sub.(1-13) monovalent hydrocarbon radicals, R 6 is selected from C.sub.(1-13) monovalent hydrocarbon radicals and substituted C.sub.(1-13) monovalent hydrocarbon radicals, Z is selected from --O-- and --C(R) 2 --, and n is an integer equal to 1 to 2000 inclusive.
Claim 29
Dependent Claim
76 words
Dianhydride terminated polydiorganosiloxane of the formula, ##STR32## where R-R 5 are members selected from hydrogen and a C.sub.(1-8) alkyl radical, R 6 is selected from a C.sub.(1-13) monovalent hydrocarbon radical and substituted C.sub.(1-13) monovalent hydrocarbon, Z is selected from --O-- and --C(R) 2 --, n is an integer equal to 1 to 2000 inclusive, m is an integer equal to 0 to 100 inclusive and the sum of n+m is equal to 2 to 2000 inclusive.
Claim 30
Dependent Claim
76 words
Dianhydride terminated polydiorganosiloxane of the formula, ##STR32## where R-R 5 are members selected from hydrogen and a C.sub.(1-8) alkyl radical, R 6 is selected from a C.sub.(1-13) monovalent hydrocarbon radical and substituted C.sub.(1-13) monovalent hydrocarbon, Z is selected from --O-- and --C(R) 2 --, n is an integer equal to 1 to 2000 inclusive, m is an integer equal to 0 to 100 inclusive and the sum of n+m is equal to 2 to 2000 inclusive.
Claim 31
Dependent Claim
97 words
Silyl polynorbornane anhydrides having the formula, ##STR33## R-R 5 are members selected from hydrogen and a C.sub.(1-8) alkyl radical, R 6 is selected from a C.sub.(1-13) monovalent hydrocarbon radical and substituted C.sub.(1-13) monovalent hydrocarbon, Z is selected from --O-- and --C(R) 2 --, X is a hydrolyzable radical selected from halo, hydrogen, C.sub.(1-8) alkoxy, acyloxy, --N(R 7 ) 2 , cyano, hydrogen, amido, carbamato, enoxy, imidato, isocyanato, oximato, isocyanate, oximato, and thioisocyanato, d is equal to 0 or 1, e is equal to 0 to 2 and the sum of d+e is equal to 1 or 2.
Claim 32
Dependent Claim
97 words
Silyl polynorbornane anhydrides having the formula, ##STR33## R-R 5 are members selected from hydrogen and a C.sub.(1-8) alkyl radical, R 6 is selected from a C.sub.(1-13) monovalent hydrocarbon radical and substituted C.sub.(1-13) monovalent hydrocarbon, Z is selected from --O-- and --C(R) 2 --, X is a hydrolyzable radical selected from halo, hydrogen, C.sub.(1-8) alkoxy, acyloxy, --N(R 7 ) 2 , cyano, hydrogen, amido, carbamato, enoxy, imidato, isocyanato, oximato, isocyanate, oximato, and thioisocyanato, d is equal to 0 or 1, e is equal to 0 to 2 and the sum of d+e is equal to 1 or 2.
Claim 33
Independent Claim
212 words
A method for making silylnorbornane anhydrides included within formula (1) which comprises effecting reaction between norbornene anhydride of the formula, ##STR34## with a silane of the formula, ##STR35## in the presence of an effective amount of a platinum catalyst, where X is a member selected from the class consisting of, (a) a hydrolyzable radical selected from the class consisting of halo, hydrogen, C.sub.(1-8) alkoxy, acyloxy, --N(R 6 ) 2 , cyano, hydrogen, amido, amino, carbamato, enoxy, imidato, isocyanato, oximato, isocyanate, oximato, thioisocyanato and ureido, (b) siloxanes having the formula, ##EQU3## (c) polysiloxanes having the formula, ##STR36## where R-R 5 are members selected from hydrogen and C.sub.(1-8) alkyl, R 6 is selected from a C.sub.(1-13) monovalent hydrocarbon radical and substituted C.sub.(1-13) monovalent hydrocarbon, Y is selected from a radical having the formula, ##STR37## and (a) radicals, Y 1 is selected from R 6 radicals, Y radicals and mixtures thereof, Z is selected from --O-- and C--(R) 2 , a is a whole number equal to 0 to 3 inclusive, b is a whole number equal to 0 to 3 inclusive, c is a whole number equal to 0 to 3 inclusive, the sum of b+c is equal to 0 to 3 inclusive, and n is an integer equal to 1 to 2000 inclusive.
Claim 34
Independent Claim
212 words
A method for making silylnorbornane anhydrides included within formula (1) which comprises effecting reaction between norbornene anhydride of the formula, ##STR34## with a silane of the formula, ##STR35## in the presence of an effective amount of a platinum catalyst, where X is a member selected from the class consisting of, (a) a hydrolyzable radical selected from the class consisting of halo, hydrogen, C.sub.(1-8) alkoxy, acyloxy, --N(R 6 ) 2 , cyano, hydrogen, amido, amino, carbamato, enoxy, imidato, isocyanato, oximato, isocyanate, oximato, thioisocyanato and ureido, (b) siloxanes having the formula, ##EQU3## (c) polysiloxanes having the formula, ##STR36## where R-R 5 are members selected from hydrogen and C.sub.(1-8) alkyl, R 6 is selected from a C.sub.(1-13) monovalent hydrocarbon radical and substituted C.sub.(1-13) monovalent hydrocarbon, Y is selected from a radical having the formula, ##STR37## and (a) radicals, Y 1 is selected from R 6 radicals, Y radicals and mixtures thereof, Z is selected from --O-- and C--(R) 2 , a is a whole number equal to 0 to 3 inclusive, b is a whole number equal to 0 to 3 inclusive, c is a whole number equal to 0 to 3 inclusive, the sum of b+c is equal to 0 to 3 inclusive, and n is an integer equal to 1 to 2000 inclusive.
Claim 35
Independent Claim
78 words
A method for making dianhydride terminated polydiorganosiloxane which comprises equilibrating an anhydride terminated diorganosiloxane of the formula, ##STR38## with a cyclopolydiorganosiloxane of the formula, ##STR39## in the presence of an acid catalyst, where where R-R 5 are members selected from hydrogen and C.sub.(1-8) alkyl, R 6 is selected from a C.sub.(1-13) monovalent hydrocarbon radical and substituted C.sub.(1-13) monovalent hydrocarbon, Z is selected from --O-- and C--(R) 2 , and m' has a value of 3 to 6 inclusive.
Claim 36
Independent Claim
78 words
A method for making dianhydride terminated polydiorganosiloxane which comprises equilibrating an anhydride terminated diorganosiloxane of the formula, ##STR38## with a cyclopolydiorganosiloxane of the formula, ##STR39## in the presence of an acid catalyst, where where R-R 5 are members selected from hydrogen and C.sub.(1-8) alkyl, R 6 is selected from a C.sub.(1-13) monovalent hydrocarbon radical and substituted C.sub.(1-13) monovalent hydrocarbon, Z is selected from --O-- and C--(R) 2 , and m' has a value of 3 to 6 inclusive.
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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) | 1986-04-25 | 1986-10-25 | 1987-04-26 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1990-04-25 | 1990-10-25 | 1991-04-26 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1994-04-25 | 1994-10-25 | 1995-04-26 | $7700.00 | Window Closed / Lapsed |