US5021585A
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Aromatic polyimide silanol compounds, precursors and polymers thereof
Assignee: Raytheon Co
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Filing: 1989-06-14
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Granted: 1991-06-04
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Expires: 2009-06-14
Abstract
Abstract Silanol-terminated aromatic imide compounds of Formula I ##STR1## where R 3 and R 4 are each selected from the group consistsing of a C 1 to C 6 alkyl group, an unsubstituted aryl group and a substituted aryl group, Z is a divalent radical. are prepared by: (a) reacting a bromoaniline compound with a chosen silylating agent to form a compound having the formula BrC 6 H 5 NSi(R 1 ) 3 Si(R 2 ) 3 , where R 1 and R 2 are each a C 1 to C 4 alkyl group (b) reacting the compound formed in step "a" with n-butyllithium, followed by reaction with a chosen halogenated alkylsilane compound to form a compound having Formula II ##STR2## where R 1 , R 2 , R 3 , and R 4 are as defined above (c) reacting the compound of Formula II formed in step "b" with a dianhydride compound having the formula ##STR3## where Z is as defined above to form a compound having Formula III ##STR4## where R 3 , R 4 , and Z are as defined above (d) hydrolyzing the compound of Formula III formed in step "c" to form the compound of Formula I. The compound of Formula I may be polymerized. A preferred copolymer in accordance with the present invention is formed by polymerizing the compound of Formula I with a silicon compound having the formula ##STR5## where R 3 and R 4 are as defined above, X=halogen, OH, OR, NRR, or ureido, R is selected from the group consisting of a C 1 to C 6 alkyl group, an unsubstituted aryl group, and a substituted aryl groups Y=--O-- or ##STR6## This invention was made with United States Government support under Contract No. F336l5-86-C-508l awarded by the Department of the Air Force. The United States Government has certain rights in this invention.
Inventors
- 👤 Thomas K. Dougherty
- 👤 Thomas W. Giants
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-27 05:45
CPC Classifications
C; C08; C08G; C08G77/00; C08G77/48; C08G77/54; C07; C07F; C07F7/00; C07F7/02; C07F7/08; C07F7/0834; C07F7/0836; C07F7/0896; C07F7/10
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
55 words
A compound having Formula I ##STR28## where R 3 and R 4 are each selected from the group consisting of a C 1 to C 6 alkyl group and an aryl group, and Z is a divalent radical selected from the group consisting of --C(CF 3 ) 2 --, CO, SO 2 , and O.
Claim 2
Dependent Claim
55 words
A compound having Formula I ##STR28## where R 3 and R 4 are each selected from the group consisting of a C 1 to C 6 alkyl group and an aryl group, and Z is a divalent radical selected from the group consisting of --C(CF 3 ) 2 --, CO, SO 2 , and O.
Claim 3
Dependent Claim
38 words
The compound of claim 1 wherein: (a) the silicon-containing radical is attached to the aromatic ring in the para position; (b) R 3 and R 4 are each methyl; and (c) Z is --C(CF 3 ) 2 --.
Claim 4
Dependent Claim
38 words
The compound of claim 1 wherein: (a) the silicon-containing radical is attached to the aromatic ring in the meta position; (b) R 3 and R 4 are each methyl; and (c) Z is --C(CF 3 ) 2 --.
Claim 5
Independent Claim
219 words
A method for forming a compound having Formula I ##STR29## where R 3 and R 4 are each selected from the group consisting of a C 1 to C 6 alkyl group and an aryl group, and Z is a divalent radical selected from the group consisting of --C(CF 3 ) 2 --, CO, SO 2 , and O comprising the steps of: (a) reacting a bromoaniline compound with a chosen silylating agent to form a compound having the formula ##STR30## where R 1 and R 2 are each a C 1 to C 4 alkyl group or where the group --NSi(R 1 ) 3 Si(R 2 ) 3 is 2,2,5,5-tetramethyl-1-aza2,5-disilacyclopentane (b) reacting the compound formed in step "a" with n-butyllithium, followed by reaction with a chosen halogenated silane compound to form a compound having Formula II ##STR31## where R 1 , R 2 , R 3 , and R 4 are as defined above (c) reacting the compound of Formula II formed in step "b" with a dianhydride compound having the formula ##STR32## where Z is as defined above to form a compound having Formula III ##STR33## where R 3 , R 4 , and Z are as defined above (d) hydrolyzing the compound of Formula III formed in step "c" to form the compound of Formula I.
Claim 6
Independent Claim
219 words
A method for forming a compound having Formula I ##STR29## where R 3 and R 4 are each selected from the group consisting of a C 1 to C 6 alkyl group and an aryl group, and Z is a divalent radical selected from the group consisting of --C(CF 3 ) 2 --, CO, SO 2 , and O comprising the steps of: (a) reacting a bromoaniline compound with a chosen silylating agent to form a compound having the formula ##STR30## where R 1 and R 2 are each a C 1 to C 4 alkyl group or where the group --NSi(R 1 ) 3 Si(R 2 ) 3 is 2,2,5,5-tetramethyl-1-aza2,5-disilacyclopentane (b) reacting the compound formed in step "a" with n-butyllithium, followed by reaction with a chosen halogenated silane compound to form a compound having Formula II ##STR31## where R 1 , R 2 , R 3 , and R 4 are as defined above (c) reacting the compound of Formula II formed in step "b" with a dianhydride compound having the formula ##STR32## where Z is as defined above to form a compound having Formula III ##STR33## where R 3 , R 4 , and Z are as defined above (d) hydrolyzing the compound of Formula III formed in step "c" to form the compound of Formula I.
Claim 7
Dependent Claim
45 words
The method of claim 4 wherein: (1) in Formula I, the silicon-containing radical is attached to the aromatic ring in the meta position; (2) in step "a" said chosen silylating agent comprises 1,1,4,4-tetramethyl-1,4-bis(N,N-diethylamino)-1,4-disilabutane; and (3) in step "b" said chosen halogenated alkylsilane compound comprises chlorodimethylsilane.
Claim 8
Dependent Claim
48 words
The method of claim 4 wherein: (1) in Formula I, the silicon-containing radical is attached to the aromatic ring in the para position; (2) in step "a" said chosen silylating agent comprises n-butyllithium and chlorotrimethyl silane; and (3) in step "b" said chosen halogenated alkylsilane compound comprises chlorodimethylsilane.
Claim 9
Dependent Claim
55 words
A compound having Formula III ##STR34## where R 3 and R 4 are each selected from the group consisting of a C 1 to C 6 alkyl group and an aryl group, and Z is a divalent radical selected from the group consisting of --C(CF 3 ) 2 --, CO, SO 2 , and O.
Claim 10
Dependent Claim
55 words
A compound having Formula III ##STR34## where R 3 and R 4 are each selected from the group consisting of a C 1 to C 6 alkyl group and an aryl group, and Z is a divalent radical selected from the group consisting of --C(CF 3 ) 2 --, CO, SO 2 , and O.
Claim 11
Dependent Claim
39 words
The compound of claim 7 wherein: (a) the silicon-containing radical is attached to the aromatic ring in the para position; (b) R 3 and R 4 are each methyl; and (c) Z is 13 C(CF 3 ) 2 --.
Claim 12
Dependent Claim
38 words
The compound of claim 7 wherein: (a) the silicon-containing radical is attached to the aromatic ring in the meta position; (b) R 3 and R 4 are each methyl; and (c) Z is --C(CF 3 ) 2 --.
Claim 13
Independent Claim
187 words
A method for forming a compound having Formula III ##STR35## where R 3 and R 4 are each selected from the group consisting of a C 1 to C 6 alkyl group and an aryl group, and Z is a divalent radical selected from the group consisting of --C(CF 3 ) 2 , CO, SO 2 , and O comprising the steps of: (a) reacting a bromoaniline compound with a chosen silylating agent to form a compound having the formula ##STR36## where R 1 and R 2 are each a C 1 to C 4 alkyl group, or where the group --NSi(R 1 ) 3 Si(R 2 ) 3 is 2,2,5,5-tetramethyl-1-aza-2,5disilacyclopentane (b) reacting the compound formed in step "a" with n-butyllithium, followed by reaction with a chosen halogenated silane compound to form a compound having Formula II; ##STR37## where R 1 , R 2 , R 3 , and R 4 are as defined above. (c) reacting the compound of Formula II formed in step "b" with a dianhydride compound having the formula ##STR38## where Z is as defined above to form the compound having Formula III.
Claim 14
Independent Claim
187 words
A method for forming a compound having Formula III ##STR35## where R 3 and R 4 are each selected from the group consisting of a C 1 to C 6 alkyl group and an aryl group, and Z is a divalent radical selected from the group consisting of --C(CF 3 ) 2 , CO, SO 2 , and O comprising the steps of: (a) reacting a bromoaniline compound with a chosen silylating agent to form a compound having the formula ##STR36## where R 1 and R 2 are each a C 1 to C 4 alkyl group, or where the group --NSi(R 1 ) 3 Si(R 2 ) 3 is 2,2,5,5-tetramethyl-1-aza-2,5disilacyclopentane (b) reacting the compound formed in step "a" with n-butyllithium, followed by reaction with a chosen halogenated silane compound to form a compound having Formula II; ##STR37## where R 1 , R 2 , R 3 , and R 4 are as defined above. (c) reacting the compound of Formula II formed in step "b" with a dianhydride compound having the formula ##STR38## where Z is as defined above to form the compound having Formula III.
Claim 15
Dependent Claim
45 words
The method of claim 10 wherein: (1) in Formula I, the silicon-containing radical is attached to the aromatic ring in the meta position, (2) in step "a" said chosen silylating agent comprises 1,1,4,4-tetramethyl-1,4-bis(N,N-diethylamino)-1,4-disilabutane; and (3) in step "b" said chosen halogenated alkylsilane compound comprises chlorodimethylsilane.
Claim 16
Dependent Claim
47 words
The method of claim 10 wherein: (1) in Formula I, the silicon-containing radical is attached to the aromatic ring in the para position, (2) in step "a" said chosen silylating agent comprises n-butyllithium and chlorotrimethylsilane; and (3) in step "b" said chosen halogenated alkylsilane compound comprises chlorodimethylsilane.
References Cited (Backward Citations)
JPS62223228A
Cited
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