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US4472565A Expired / Lapsed US ⏱️ 0.0 years remaining

Silicone-polyimide copolymers, condensation vulcanizable compositions obtained therefrom, and methods for making

Assignee: General Electric Co
•
Filing: 1984-01-03
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Granted: 1984-09-18
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Expires: 2004-01-03
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Abstract

Abstract Silicone-polyimide copolymers having terminal silanol or silicon hydride radicals are provided based on the use of a norbornene terminated polyimide. A hydrosilation reaction is employed to introduce silicon-hydrogen into the terminal position of the polyimide having norbornene termination. The resulting hydrosilyl terminated polyimide is reacted with silanol terminated polydiorganosiloxane in the presence of a catalyst to produce silanol terminated polydiorganosiloxane-polyimide copolymer. Room temperature or low temperature condensation vulcanizable compositions based on the use of such silanol-terminated copolymers provide cured silicon-polyimide copolymers exhibiting improved toughness.

Inventors

  • 👤 Hong-Son Ryang

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-27 05:45
CPC Classifications
C; C07; C07D; C07D209/00; C07D209/56; C07D209/58; C07D209/72; C07D209/76; C07F; C07F7/00; C07F7/02; C07F7/08; C07F7/0896; C08; C08G; C08G73/00; C08G73/06; C08G73/10; C08G73/1057; C08G73/106; C08G77/00; C08G77/42; C08G77/452; C08G77/455; C08G77/48; C08G77/54; C08L; C08L79/00; C08L79/04; C08L79/08; C08L83/00; C08L83/10

Claims Analysis

Total Claims: 20
Claim 1
Independent Claim 9 words
Condensation vulcanizable compositions comprising a silanol terminated polydiorganosiloxane-polyimide copolymer.
Claim 2
Dependent Claim 9 words
Condensation vulcanizable compositions comprising a silanol terminated polydiorganosiloxane-polyimide copolymer.
Claim 3
Dependent Claim 43 words
Condensation vulcanizable compositions comprising by weight (A) 100 parts of a silanol terminated polydiorganosiloxane-polyimide copolymer, (B) 0.002 to 10 parts of a curing agent, (C) 0 to 5 parts of a condensation catalyst and (D) 0 to 3000 parts of a silanol-terminated polydiorganosiloxane.
Claim 4
Dependent Claim 43 words
Condensation vulcanizable compositions comprising by weight (A) 100 parts of a silanol terminated polydiorganosiloxane-polyimide copolymer, (B) 0.002 to 10 parts of a curing agent, (C) 0 to 5 parts of a condensation catalyst and (D) 0 to 3000 parts of a silanol-terminated polydiorganosiloxane.
Claim 5
Dependent Claim 15 words
A condensation vulcanizable composition in accordance with claim 1, which is curable at room temperature.
Claim 6
Dependent Claim 13 words
A condensation vulcanizable composition in accordance with claim 1, which is moisture curable.
Claim 7
Dependent Claim 125 words
A room temperature vulcanizable composition in accordance with claim 1, where the curing agent is an alkoxy silane having the formula, ##STR24## where R 7 is selected from the class consisting of C.sub.(1-13) monovalent hydrocarbon radicals and substituted C.sub.(1-13) monovalent hydrocarbon radicals, R 10 is a C.sub.(1-8) aliphatic organic radical selected from the group consisting of alkyl, alkylether, alkylester, alkylketone, and alkylcyano radicals, or C.sub.(7-13) aralkyl radical, X is a hydrolyzable leaving group selected from the group consisting of acyloxy, amido, amino, carbamato, enoxy, halo, imidato, isocyanato, ketoximato, oximato, thioisocyanato and ureido radicals and a is equal to 0 or 4 inclusive, b is a whole number equal to 0 or 1 and the sum of a+b is equal to from 0 to 4 inclusive.
Claim 8
Dependent Claim 17 words
A room temperature vulcanizable composition in accordance with claim 1, where the curing agent is trimethoxy-N-methylacetamide silane.
Claim 9
Dependent Claim 16 words
A room temperature vulcanizable composition in accordance with claim 1, where the curing agent is methyltriacetoxysilane.
Claim 10
Dependent Claim 9 words
A silicon hydride terminated polyimide of the formula, ##STR25##
Claim 11
Dependent Claim 9 words
A silicon hydride terminated polyimide of the formula, ##STR25##
Claim 12
Dependent Claim 17 words
A silanol terminated polydimethylsiloxane-polyimide copolymer of the formula ##STR26## where x is an integer greater than 2.
Claim 13
Dependent Claim 17 words
A silanol terminated polydimethylsiloxane-polyimide copolymer of the formula ##STR26## where x is an integer greater than 2.
Claim 14
Dependent Claim 11 words
A condensation vulcanizable composition in accordance with claim 1, containing methyltrimethoxysilane.
Claim 15
Dependent Claim 246 words
A silanol or silicon hydride terminated polydiorganosiloxane-polyimide copolymer comprising by weight from 1 to 99% of polyimide blocks of the formula, ##STR27## chemically combined with from 99% to 1% of polydiorganosiloxane blocks of the formula, ##STR28## where R is a divalent radical selected from the class consisting of (a) aromatic hydrocarbon radicals having from 6-20 carbon atoms and halogenated aromatic hydrocarbon radicals having from 6-20 carbon atoms, (b) alkylene radicals having from 2-20 carbon atoms and cycloalkylene radicals having from 2-20 carbon atoms, (c) C.sub.(2-8) alkylene terminated polydiorganosiloxane, and (d) radicals included by the general formula, ##STR29## Q' is a member selected from the class consisting of ##STR30## x is a whole number from 1 to 5 inclusive, Q is a tetravalent radical selected from ##STR31## where D is a member selected from ##STR32## and R 8 is a divalent radical selected from ##STR33## and divalent organic radicals of the general formula, ##STR34## X is a member selected from the class consisting of divalent radicals of the formula, ##STR35## y is an integer from 1 to 5, R 1 -R 6 are selected from hydrogen and C.sub.(1-8) alkyl radicals, R 7 is selected from the class consisting of C.sub.(1-13) monovalent hydrocarbon radicals and substituted C.sub.(1-13) monovalent hydrocarbon radicals, Y is a divalent radical selected from --O-- and --C(R 1 ) 2 --, n is an integer equal to 0-200 inclusive, m is an integer equal to 1-2000 inclusive and p is equal to 0 or 1.
Claim 16
Dependent Claim 246 words
A silanol or silicon hydride terminated polydiorganosiloxane-polyimide copolymer comprising by weight from 1 to 99% of polyimide blocks of the formula, ##STR27## chemically combined with from 99% to 1% of polydiorganosiloxane blocks of the formula, ##STR28## where R is a divalent radical selected from the class consisting of (a) aromatic hydrocarbon radicals having from 6-20 carbon atoms and halogenated aromatic hydrocarbon radicals having from 6-20 carbon atoms, (b) alkylene radicals having from 2-20 carbon atoms and cycloalkylene radicals having from 2-20 carbon atoms, (c) C.sub.(2-8) alkylene terminated polydiorganosiloxane, and (d) radicals included by the general formula, ##STR29## Q' is a member selected from the class consisting of ##STR30## x is a whole number from 1 to 5 inclusive, Q is a tetravalent radical selected from ##STR31## where D is a member selected from ##STR32## and R 8 is a divalent radical selected from ##STR33## and divalent organic radicals of the general formula, ##STR34## X is a member selected from the class consisting of divalent radicals of the formula, ##STR35## y is an integer from 1 to 5, R 1 -R 6 are selected from hydrogen and C.sub.(1-8) alkyl radicals, R 7 is selected from the class consisting of C.sub.(1-13) monovalent hydrocarbon radicals and substituted C.sub.(1-13) monovalent hydrocarbon radicals, Y is a divalent radical selected from --O-- and --C(R 1 ) 2 --, n is an integer equal to 0-200 inclusive, m is an integer equal to 1-2000 inclusive and p is equal to 0 or 1.
Claim 17
Dependent Claim 221 words
A silicon hydride terminated polyimide having the formula, ##STR36## where R is a divalent radical selected from the class consisting of (a) aromatic hydrocarbon radicals having from 6-20 carbon atoms and halogenated aromatic hydrocarbon aromatic hydrocarbon radicals having from 6-20 carbon atoms, (b) alkylene radicals having from 2-20 carbon atoms and cycloalkylene radicals having from 2-20 carbon atoms, (c) C.sub.(2-8) alkylene terminated polydiorganosiloxane, and (d) radicals included by the general formula, ##STR37## Q' is a member selected from the class consisting of ##STR38## x is a whole number from 1 to 5 inclusive, Q is a tetravalent radical selected from ##STR39## where D is a member selected from ##STR40## and R 8 is a divalent radical selected from ##STR41## and divalent organic radicals of the general formula, ##STR42## X is a member selected from the class consisting of divalent radicals of the formula, ##STR43## y is an integer from 1 to 5, R 1 -R 6 are selected from hydrogen and C.sub.(1-8) alkyl radicals, R 7 is selected from the class consisting of C.sub.(1-13) monovalent hydrocarbon radicals and substituted C.sub.(1-13) monovalent hydrocarbon radicals, Y is a divalent radical selected from --O-- and --C(R 1 ) 2 --, n is an integer equal to 0-200 inclusive, m is an integer equal to 1-2000 inclusive and p is equal to 0 or 1.
Claim 18
Dependent Claim 221 words
A silicon hydride terminated polyimide having the formula, ##STR36## where R is a divalent radical selected from the class consisting of (a) aromatic hydrocarbon radicals having from 6-20 carbon atoms and halogenated aromatic hydrocarbon aromatic hydrocarbon radicals having from 6-20 carbon atoms, (b) alkylene radicals having from 2-20 carbon atoms and cycloalkylene radicals having from 2-20 carbon atoms, (c) C.sub.(2-8) alkylene terminated polydiorganosiloxane, and (d) radicals included by the general formula, ##STR37## Q' is a member selected from the class consisting of ##STR38## x is a whole number from 1 to 5 inclusive, Q is a tetravalent radical selected from ##STR39## where D is a member selected from ##STR40## and R 8 is a divalent radical selected from ##STR41## and divalent organic radicals of the general formula, ##STR42## X is a member selected from the class consisting of divalent radicals of the formula, ##STR43## y is an integer from 1 to 5, R 1 -R 6 are selected from hydrogen and C.sub.(1-8) alkyl radicals, R 7 is selected from the class consisting of C.sub.(1-13) monovalent hydrocarbon radicals and substituted C.sub.(1-13) monovalent hydrocarbon radicals, Y is a divalent radical selected from --O-- and --C(R 1 ) 2 --, n is an integer equal to 0-200 inclusive, m is an integer equal to 1-2000 inclusive and p is equal to 0 or 1.
Claim 19
Dependent Claim 263 words
A silanol terminated polyimide having the formula, ##STR44## where Z is a divalent group shown by the formula, ##STR45## R is a divalent radical selected from the class consisting of (a) aromatic hydrocarbon radicals having from 6-20 carbon atoms and halogenated aromatic hydrocarbon radicals having from 6-20 carbon atoms, (b) alkylene radicals having from 2-20 carbon atoms and cycloalkylene radicals having from 2-20 carbon atoms, (c) C.sub.(2-8) alkylene terminated polydiorganosiloxane, and (d) radicals included by the general formula, ##STR46## Q' is a member selected from the class consisting of ##STR47## x is a whole number from 1 to 5 inclusive, Q is a tetravalent radical selected from ##STR48## where D is a member selected from ##STR49## and R 8 is a divalent radical selected from ##STR50## and divalent organic radicals of the general formula, ##STR51## X is a member selected from the class consisting of divalent radicals of the formula, ##STR52## y is an integer from 1 to 5, R 1 -R 6 are selected from hydrogen and C.sub.(1-8) alkyl radicals, R 7 is selected from the class consisting of C.sub.(1-13) monovalent hydrocarbon radicals and substituted C.sub.(1-13) monovalent hydrocarbon radicals, R 9 is selected from hydrogen and R 7 , Y is a divalent radical selected from --O-- and --C(R 1 ) 2 --, n is an integer equal to 0-200 inclusive, p is equal to 0 or 1, r is a whole number equal to 0 or 1, m is an integer equal to 1-2000 inclusive and l is an integer having a value of from about 1 to 10 4 inclusive.
Claim 20
Dependent Claim 263 words
A silanol terminated polyimide having the formula, ##STR44## where Z is a divalent group shown by the formula, ##STR45## R is a divalent radical selected from the class consisting of (a) aromatic hydrocarbon radicals having from 6-20 carbon atoms and halogenated aromatic hydrocarbon radicals having from 6-20 carbon atoms, (b) alkylene radicals having from 2-20 carbon atoms and cycloalkylene radicals having from 2-20 carbon atoms, (c) C.sub.(2-8) alkylene terminated polydiorganosiloxane, and (d) radicals included by the general formula, ##STR46## Q' is a member selected from the class consisting of ##STR47## x is a whole number from 1 to 5 inclusive, Q is a tetravalent radical selected from ##STR48## where D is a member selected from ##STR49## and R 8 is a divalent radical selected from ##STR50## and divalent organic radicals of the general formula, ##STR51## X is a member selected from the class consisting of divalent radicals of the formula, ##STR52## y is an integer from 1 to 5, R 1 -R 6 are selected from hydrogen and C.sub.(1-8) alkyl radicals, R 7 is selected from the class consisting of C.sub.(1-13) monovalent hydrocarbon radicals and substituted C.sub.(1-13) monovalent hydrocarbon radicals, R 9 is selected from hydrogen and R 7 , Y is a divalent radical selected from --O-- and --C(R 1 ) 2 --, n is an integer equal to 0-200 inclusive, p is equal to 0 or 1, r is a whole number equal to 0 or 1, m is an integer equal to 1-2000 inclusive and l is an integer having a value of from about 1 to 10 4 inclusive.

References Cited (Backward Citations)

US3288754A Cited
US3325450A Cited
US3338859A Cited
US4381396A Cited
US4404350A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1987-09-18 1988-03-19 1988-09-18 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1991-09-18 1992-03-19 1992-09-18 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1995-09-18 1996-03-19 1996-09-18 $7700.00 Window Closed / Lapsed

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