US4973645A
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US
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Novel soluble polyimidesiloxanes and methods for their preparation and use
Assignee: Sumitomo Bakelite Co Ltd
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Filing: 1988-09-01
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Granted: 1990-11-27
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Expires: 2008-09-01
Abstract
Abstract Fully imidized polyimidisiloxanes which are based on oxydiphthalic anhydride are soluble in diglyme which gives them particular utility in the micro-electronics industry. The polymers are prepared from oxydiphthalic anhydride, a difunctional siloxane monomer and an organic diamine that provides an assymetrical structure in the polyimidesiloxane polymer chain. The polyimide-siloxane can be prepared with functional groups which render them directly curable. The polyimidesiloxanes can also be prepared with functional groups which when reacted with an unsaturated compound renders the polymers curable. The products of the invention can be used in the form of solutions in the micro-electronic industry. The polymers can also be used in wire and cable coating and to prepare films, fibers, and molded and extruded articles.
Inventors
- 👤 Chung J. Lee
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 09:01
CPC Classifications
C; C08; C08G; C08G73/00; C08G73/06; C08G73/10; C08G73/1057; C08G73/106; C08G77/00; C08G77/42; C08G77/452; C08G77/455
Claims Analysis
Total Claims: 55
Claim 1
Independent Claim
83 words
A fully imidized polyimidesiloxane soluble in diglyme which comprises the reaction product if an organic dianhydride, an aromatic diamine, and a siloxane monomer, wherein said organic dianhydride is free of polyether linkage and at least about 80 weight percent of said organic dianhydride is oxydiphthalic anhydride, said aromatic diamine being selected to provide an asymmetrical structure in the polyimidesiloxane, and said siloxane monomer being selected to have sufficient block size and being present in an amount to render the polyimidesiloxane soluble in diglyme.
Claim 2
Dependent Claim
83 words
A fully imidized polyimidesiloxane soluble in diglyme which comprises the reaction product if an organic dianhydride, an aromatic diamine, and a siloxane monomer, wherein said organic dianhydride is free of polyether linkage and at least about 80 weight percent of said organic dianhydride is oxydiphthalic anhydride, said aromatic diamine being selected to provide an asymmetrical structure in the polyimidesiloxane, and said siloxane monomer being selected to have sufficient block size and being present in an amount to render the polyimidesiloxane soluble in diglyme.
Claim 3
Dependent Claim
12 words
The polyimidesiloxane of claim 1 wherein the oxydiphthalic anhydride is 4,4'-oxydiphthalic anhydride.
Claim 4
Dependent Claim
12 words
The polyimidesiloxane of claim 1 wherein the oxydiphthalic anhydride is 3,3'-oxydiphthalic anhydride.
Claim 5
Dependent Claim
13 words
The polyimidesiloxane of claim 1 wherein the oxydiphthalic anhydride is 3,4'-oxydiphthalic anhydride. PG,41
Claim 6
Dependent Claim
46 words
A polyimidesiloxane according to claim 1 comprising the reaction product of 4,4'-oxydiphthalic anhydride, a difunctional siloxane monomer, and 2,4-tolyldiamine wherein the 4,4'-oxydiphthalic anhydride is the sole essential organic dianhydride monomeric component of the polyimidesiloxane, and wherein the organic dianhydride monomeric component is free of polyether linkage.
Claim 7
Dependent Claim
46 words
A polyimidesiloxane according to claim 1 comprising the reaction product of 4,4'-oxydiphthalic anhydride, a difunctional siloxane monomer, and 2,5-tolyldiamine wherein the 4,4'-oxydiphthalic anhydride is the sole essential organic dianhydride monomeric component of the polyimidesiloxane, and wherein the organic dianhydride monomeric component is free of polyether linkage.
Claim 8
Dependent Claim
46 words
A polyimidesiloxane according to claim 1 comprising the reaction product of 4,4'-oxydiphthalic anhydride, a difunctional siloxane monomer, and 2,6-tolyldiamine wherein the 4,4'-oxydiphthalic anhydride is the sole essential organic dianhydride monomeric component of the polyimidesiloxane, and wherein the organic dianhydride monomeric component is free of polyether linkage.
Claim 9
Dependent Claim
51 words
A polyimidesiloxane according to clam 1 comprising the reaction product of 4,4'-oxydiphthalic anhydride, a difunctional siloxane monomer, and a mixture of 2,4-tolyldiamine and 2,6-tolyldiamine wherein the 4,4'-oxydiphthalic anhydride is the sole essential organic dianhydride monomeric component of the polyimidesiloxane, and wherein the organic dianhydride monomeric component is free of polyether linkage.
Claim 10
Dependent Claim
51 words
A polyimidesiloxane according to clam 1 comprising the reaction product of 4,4'-oxydiphthalic anhydride, a difunctional siloxane monomer, and a mixture of 2,4-tolyldiamine and 2,6-tolyldiamine wherein the 4,4'-oxydiphthalic anhydride is the sole essential organic dianhydride monomeric component of the polyimidesiloxane, and wherein the organic dianhydride monomeric component is free of polyether linkage.
Claim 11
Dependent Claim
46 words
A polyimidesiloxane according to claim 1 comprising the reaction product of 4,4'-oxydiphthalic anhydride, a difunctional siloxane monomer, and m-xylyldiamine wherein the 4,4'-oxydiphthalic anhydride is the sole essential organic dianhydride monomeric component of the polyimidesiloxane, and wherein the organic dianhydride monomeric component is free of polyether linkage.
Claim 12
Dependent Claim
47 words
A polyimidesiloxane according to claim 1 comprising the reaction product of 4,4'-oxydiphthalic anhydride, a difunctional siloxane monomer, and 2,4-diamino-5-chloro toluene wherein the 4,4'-oxydiphthalic anhydride is the sole essential organic dianhydride monomeric component of the polyimidesiloxane, and wherein the organic dianhydride monomeric component is free of polyether linkage.
Claim 13
Dependent Claim
47 words
A polyimidesiloxane according to claim 1 comprising the reaction product of 4,4'-oxydiphthalic anhydride, a difunctional siloxane monomer, and 2,4-diamino-6-chloro toluene wherein the 4,4'-oxydiphthalic anhydride is the sole essential organic dianhydride monomeric component of the polyimidesiloxane, and wherein the organic dianhydride monomeric component is free of polyether linkage.
Claim 14
Dependent Claim
46 words
A polyimidesiloxane according to claim 1 comprising the reaction product of 4,4'-oxydiphthalic anhydride, a difunctional siloxane monomer, and 2,4,6-trimethyl-2,3-diaminobenzene wherein the 4,4'-oxydiphthalic anhydride is the sole essential organic dianhydride monomeric component of the polyimidesiloxane, and wherein the organic dianhydride monomeric component is free of polyether linkage.
Claim 15
Dependent Claim
47 words
A polyimidesiloxane according to claim 1 comprising the reaction product of 4,4'-oxydiphthalic anhydride, a difunctional siloxane monomer, and m,m-methylene dianiline wherein the 4,4'-oxydiphthalic anhydride is the sole essential organic dianhydride monomeric component of the polyimidesiloxane, and wherein the organic dianhydride monomeric component is free of polyether linkage.
Claim 16
Dependent Claim
47 words
A polyimidesiloxane according to claim 1 comprising the reaction product of 4,4'-oxydiphthalic anhydride, a difunctional siloxane monomer, and m,m-sulfone dianiline wherein the 4,4'-oxydiphthalic anhydride is the sole essential organic dianhydride monomeric component of the polyimidesiloxane, and wherein the organic dianhydride monomeric component is free of polyether linkage.
Claim 17
Dependent Claim
47 words
A polyimidesiloxane according to claim 1 comprising the reaction product of 4,4'-oxydiphthalic anhydride, a difunctional siloxane monomer, and o,m-sulfone dianiline wherein the 4,4'-oxydiphthalic anhydride is the sole essential organic dianhydride monomeric component of the polyimidesiloxane, and wherein the organic dianhydride monomeric component is free of polyether linkage.
Claim 18
Dependent Claim
46 words
A polyimidesiloxane according to claim 1 comprising the reaction product of 4,4'-oxydiphthalic anhydride, a difunctional siloxane monomer, and diaminoanthraquinone wherein the 4,4'-oxydiphthalic anhydride is the sole essential organic dianhydride monomeric component of the polyimidesiloxane, and wherein the organic dianhydride monomeric component is free of polyether linkage.
Claim 19
Dependent Claim
36 words
The polyimidesiloxane of claim 1 wherein at least a portion of the organic diamine has the formula ##STR25## wherein Ar is an aromatic radical, and R" is at least one of a hydroxyl, carboxyl, or hydrothiol.
Claim 20
Dependent Claim
9 words
The polyimidesiloxane of claim 17 wherein R" is carboxyl.
Claim 21
Dependent Claim
40 words
The polyimidesiloxane of claim 1 wherein at least a portion of the organic diamine component has the formula ##STR26## wherein Ar is an aromatic radical, and R'" is at least one of an acrylic-, an ethylenic- or an acetylenic-bearing radical.
Claim 22
Dependent Claim
13 words
The polyimidesiloxane of claim 1 wherein the siloxane monomer is a siloxane diamine.
Claim 23
Dependent Claim
110 words
The polyimidesiloxane of claim 20 wherein the siloxane diamine has the formula ##STR27## wherein R' is independently selected from substituted or unsubstituted aliphatic difunctional radicals of 1 to 12 carbon atoms, and wherein one or more of R 1 , R 2 , R 3 and R 4 can be vinyl, hydroxyl, radicals, and the remainder of R 1 , R 2 , R 3 , and R 4 are independently selected from a substituted or unsubstituted aliphatic monofunctional radical of 1 to 12 carbon atoms, or substituted or unsubstituted aromatic monofunctional radicals of 6 to 10 carbon atoms, and m is a number from about 5 to about 200.
Claim 24
Dependent Claim
25 words
The polyimidesiloxane according to claim 21 wherein the remainder of R 1 , R 2 , R 3 , and R 4 are methyl groups.
Claim 25
Dependent Claim
12 words
The polyimidesiloxane according to claim 22 wherein R' is CH 23 .
Claim 26
Dependent Claim
30 words
The polyimidesiloxane according to claim 21 wherein at least one of R 1 , R 2 , R 3 and R 4 is vinyl and the remainder are methyl groups.
Claim 27
Dependent Claim
14 words
The polyimidesiloxane according to claim 30 wherein the R' is CH 2 3 .
Claim 28
Dependent Claim
47 words
The polyimidesiloxane of claim 26 wherein at least a portion of the siloxane diamine of the formula comprises a siloxane diamine component wherein at least one of the hydroxyl or vinyl radicals is reacted with a compound having a radical selected from acrylic-, ethylenic- or acetylenic-bearing radicals.
Claim 29
Dependent Claim
9 words
The polyimidesiloxane of claim 26 comprising an acrylic-bearing radical.
Claim 30
Dependent Claim
13 words
The polyimidesiloxane of claim 1 wherein the siloxane monomer is a siloxane dianhydride.
Claim 31
Dependent Claim
122 words
The polyimidesiloxane of claim 28 wherein the siloxane dianhydride has the formula ##STR28## wherein R is substituted or unsubstituted aliphatic trifunctional radicals of 1 to 12 carbon atoms, or substituted or unsubstituted aromatic trifunctional radicals of 6 to 10 carbon atoms, and wherein one or more of R 1 , R 2 , R 3 and R 4 can be halogen, hydride (H), vinyl or a hydroxyl group, and the remainder of R 1 , R 2 , R 3 , and R 4 are independently selected from a substituted or unsubstituted aliphatic monofunctional radical of 1 to 12 carbon atoms, or substituted or unsubstituted aromatic monofunctional radicals of 6 to 10 carbon atoms, and wherein m is about 5 to 50.
Claim 32
Dependent Claim
24 words
The polyimidesiloxane of claim 29 wherein the remainder of R 1 , R 2 , R 3 , and R 4 are methyl groups.
Claim 33
Dependent Claim
9 words
The polyimidesiloxane of claim 30 wherein R is ##STR29##
Claim 34
Dependent Claim
30 words
The polyimidesiloxane according to claim 29 wherein at least one of R 1 , R 2 , R 3 and R 4 is vinyl and the remainder are methyl groups.
Claim 35
Dependent Claim
10 words
The polyimidesiloxane according to claim 32 wherein R is ##STR30##
Claim 36
Dependent Claim
52 words
The polyimidesiloxane of claim 29 wherein at least a portion of the siloxane dianhydride component of the formula comprises a siloxane dianhydride component wherein at least one of the hydride(H), halogen, hydroxyl or vinyl radicals is reacted with a compound having a is a radical selected from acrylic, ethylenic or acetylenic radicals.
Claim 37
Dependent Claim
9 words
The polyimidesiloxane of claim 34 comprising an acrylic-bearing radical.
Claim 38
Dependent Claim
15 words
A solution comprising the polyimidesiloxane of claim 1 dissolved in a solvent for the polyimidesiloxane.
Claim 39
Dependent Claim
22 words
The solution of claim 36 wherein the solvent is selected from diglyme, triglyme, 1-methyl-2-pyrrolidinone tetrahydrofuran, methyl ethyl ketone, phenols and chlorinated solvents.
Claim 40
Dependent Claim
13 words
An article comprising a substrate coated with a polyimide-siloxane according to claim 1.
Claim 41
Dependent Claim
13 words
An article of claim 38 wherein the substrate is a wire or cable.
Claim 42
Dependent Claim
10 words
A film prepared from the polyimidesiloxane according to claim 1.
Claim 43
Dependent Claim
10 words
A fiber prepared from the polyimidesiloxane according to claim 1.
Claim 44
Dependent Claim
11 words
A molded article prepared from a polyimidesiloxane according to claim 1.
Claim 45
Dependent Claim
11 words
An extruded article prepared from a polyimidesiloxane according to claim 1.
Claim 46
Dependent Claim
6 words
A cured composition of claim 26.
Claim 47
Dependent Claim
6 words
A cured composition of claim 34.
Claim 48
Dependent Claim
27 words
The polyimidesiloxane of claim 1 wherein the organic dianhydride is 4,4'-oxydiphthalic anhydride, the difunctional siloxane monomer is a siloxane diamine, and the organic diamine is a tolyldiamine.
Claim 49
Dependent Claim
27 words
The polyimidesiloxane of claim 1 wherein the organic dianhydride is 4,4'-oxydiphthalic anhydride, the difunctional siloxane monomer is a siloxane diamine, and the organic diamine is a tolyldiamine.
Claim 50
Dependent Claim
107 words
A fully imidized polyimidesiloxane soluble in diglyme and which is capable of forming a photosensitive polyimidesiloxane, which comprises the reaction product of an organic dianhydride, an aromatic diamine, and a siloxane monomer, wherein said organic dianhydride is free of polyether linkage and at least about 80 weight percent of said organic dianhydride is oxydiphthalic anhydride, said aromatic diamine being selected to provide an asymmetrical structure in the polyimidesiloxane, and said siloxane monomer being selected to have sufficient block size and being present in an amount to render the polyimidesiloxane soluble in diglyme, comprising at least one radical selected from hydride (H), hydroxyl, halogen, carboxyl, hydrothiol or vinyl.
Claim 51
Dependent Claim
107 words
A fully imidized polyimidesiloxane soluble in diglyme and which is capable of forming a photosensitive polyimidesiloxane, which comprises the reaction product of an organic dianhydride, an aromatic diamine, and a siloxane monomer, wherein said organic dianhydride is free of polyether linkage and at least about 80 weight percent of said organic dianhydride is oxydiphthalic anhydride, said aromatic diamine being selected to provide an asymmetrical structure in the polyimidesiloxane, and said siloxane monomer being selected to have sufficient block size and being present in an amount to render the polyimidesiloxane soluble in diglyme, comprising at least one radical selected from hydride (H), hydroxyl, halogen, carboxyl, hydrothiol or vinyl.
Claim 52
Dependent Claim
9 words
The polyimidesiloxane of claim 48 comprising a carboxyl radical.
Claim 53
Dependent Claim
40 words
A photosensitive polyimidesiloxane of claim 48 wherein at least one of the hydride (H), hydroxyl halogen, carboxyl, hydrothiol, or vinyl radicals is reacted with at least one radical selected from an acrylic radical, an ethylenic radical or an acetylenic radical.
Claim 54
Dependent Claim
9 words
The polyimidesiloxane of claim 50 comprising an acrylic radical.
Claim 55
Dependent Claim
6 words
A cured composition of claim 50.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1993-11-26 | 1994-05-28 | 1994-11-27 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1997-11-26 | 1998-05-28 | 1998-11-27 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2001-11-26 | 2002-05-28 | 2002-11-27 | $7700.00 | Window Closed / Lapsed |