US4778859A
Expired / Lapsed
US
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Tetramine derived polyimide with pendant unsaturation, and various photosensitive compositions therefrom
Assignee: Asahi Kasei Corp
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Filing: 1986-04-28
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Granted: 1988-10-18
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Expires: 2006-04-28
Abstract
Abstract A curable composition comprising (a) a curable polyimide soluble in organic solvents and (b) a polymerization initiator as essential components, said polyimide consisting of recurring units represented by the formula ##STR1## wherein, each of X, X 1 , X 2 , X 3 and X 4 is a tetravalent carbocyclic or heterocyclic residue, each of Y 1 , Y 2 , and Y 3 is a divalent carbocylic or heterocyclic residue, at least one of Z 1 and Z 2 is a residue having a reactive carbon-carbon double bond, and each of l, m, and n is an integer from 0 to 20, preferably from 0 to 10. The polyimide may include (a) polyacrylate compounds (b) bis-imide compounds (c) photosensitive polyimide precursors (d) oxime initiators (e) a 3 component sensitizer of a phenone compound, a mercapto compound, and an arylamine-alkanol, or mixtures of a,b,c,d, and e.
Inventors
- 👤 Hideo Ai
- 👤 Akihiko Ikeda
- 👤 Kan-ichi Yokota
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 02:24
CPC Classifications
G; G03; G03F; G03F7/00; G03F7/004; G03F7/025; G03F7/038; G03F7/0387; C; C08; C08G; C08G73/00; C08G73/06; C08G73/10; C08G73/1003; C08G73/1007; C08G73/101; C08G73/1039; C08G73/1046; C08G73/105; C08G73/1057; C08G73/1064; C08G73/1067; C08G73/1071; C08G73/1075; C08G73/1082
Claims Analysis
Total Claims: 35
Claim 1
Independent Claim
131 words
A composition comprising (a) a curable polyimide soluble in organic solvents and (b) a photopolymerization initiator as essential components, said polyimide consisting of recurring units represented by the formula ##STR34## wherein, each of X, X 1 , X 2 , X 3 , and X 4 is a tetravalent carbocyclic or heterocyclic residue, each of Y 1 , Y 2 , and Y 3 is a divalent carbocyclic or heterocyclic residue, each of Z 1 and Z 2 is an aromatic hydrocarbon residue of from 6 to 30 carbon atoms or a residue having a reactive carbon-carbon double bond, at least one of Z 1 and Z 2 is a residue having a reactive carbon-carbon double bond, and each of l, m, and n is an integer from 0 to 20.
Claim 2
Dependent Claim
131 words
A composition comprising (a) a curable polyimide soluble in organic solvents and (b) a photopolymerization initiator as essential components, said polyimide consisting of recurring units represented by the formula ##STR34## wherein, each of X, X 1 , X 2 , X 3 , and X 4 is a tetravalent carbocyclic or heterocyclic residue, each of Y 1 , Y 2 , and Y 3 is a divalent carbocyclic or heterocyclic residue, each of Z 1 and Z 2 is an aromatic hydrocarbon residue of from 6 to 30 carbon atoms or a residue having a reactive carbon-carbon double bond, at least one of Z 1 and Z 2 is a residue having a reactive carbon-carbon double bond, and each of l, m, and n is an integer from 0 to 20.
Claim 3
Dependent Claim
29 words
A curable composition of claim 1, wherein X in formula [I] is a residue represented by the formula ##STR35## wherein a is 0 or 1 and X' is ##STR36##
Claim 4
Dependent Claim
23 words
A curable composition of claim 2, wherein X in formula [I] is a residue represented by the following formula X(A) or X(B): ##STR37##
Claim 5
Dependent Claim
56 words
A curable composition of claim 1, wherein each of X 1 , X 2 , X 3 , and X 4 in formula [I] is an aromatic hydrocarbon residue of 6 to 20 carbon atoms or a residue represented by the formula ##STR38## wherein b is 0 or 1 and X" is --CH 2 --, ##STR39##
Claim 6
Dependent Claim
36 words
A curable composition of claim 4, wherein each of X 1 , X 2 , X 3 , and X 4 in formula [I] is a residue represented by the following formula X(C) or X(D): ##STR40##
Claim 7
Dependent Claim
30 words
A curable composition of claim 5, wherein each of X 1 , X 2 , X 3 , and X 4 in formula [I] is the residue of formula X(C).
Claim 8
Dependent Claim
60 words
A curable composition of claim 6, wherein at least one of Z 1 and Z 2 in formula [I] is a residue represented by the following formula (Za) to (Zf): ##STR41## wherein each of R 5 and R 6 is H, CH 3 , ##STR42## Cl--, Br; ##STR43## wherein R 7 is --O-- or --(CH 2 ) 3 --, ##STR44##
Claim 9
Dependent Claim
32 words
A curable composition of claim 7, wherein at least one of Z 1 and Z 2 in formula [I] is a residue represented by the following formula Z(A), Z(B), or Z(C): ##STR45##
Claim 10
Dependent Claim
25 words
A curable composition of claim 8, wherein at least one of Z 1 and Z 2 in formula [I] is the residue of formula Z(C).
Claim 11
Dependent Claim
33 words
A curable composition of claim 1, wherein Z 1 or Z 2 , in formula [I], having no reactive carbon-carbon double bond, is an aromatic hydrocarbon residue of 6 to 30 carbon atoms.
Claim 12
Dependent Claim
36 words
A curable composition of claim 10, wherein Z 1 or Z 2 , in formula [I], having no reactive carbon-carbon double bond, is a residue represented by one of the following formulae Z(A) to Z(D): ##STR46##
Claim 13
Dependent Claim
17 words
A curable composition of claim 1, wherein l, m, and n in formula [I] are all 0.
Claim 14
Dependent Claim
77 words
A curable composition of claim 1, wherein each of Y 1 , Y 2 , and Y 3 in formula [I] is a residue represented by the formula ##STR47## wherein, c is 0 or 1, Y' is --CH 2 --, ##STR48## --O--, or --S--, each of R 1 and R 3 is alkyl of 1 to 6 carbon atoms, and each of R 2 and R 4 is hydrogen or alkyl of 1 to 6 carbon atoms.
Claim 15
Dependent Claim
75 words
A curable composition of claim 13, wherein each of Y 1 , Y 2 , and Y 3 in formula [I] is a residue represented by the formula ##STR49## wherein each of R 1 and R 3 is --CH 3 --, --CH 2 CH 3 , or --CH(CH 3 ) 2 and each of R 2 and R 4 is --H, --CH 3 , --CH 2 CH 3 , or --CH(CH 3 ) 2 .
Claim 16
Dependent Claim
29 words
A curable composition of claim 14, wherein each of Y 1 , Y 2 , and Y 3 in formula [I] is a residue represented by the formula ##STR50##
Claim 17
Dependent Claim
50 words
A curable composition of claim 1, wherein each of Y 1 , Y 2 , and Y 3 in formula [I] is a residue represented by the formula ##STR51## wherein X is as defined in claim 1 and Y" is an aromatic hydrocarbon residue of 6 to 30 carbon atoms.
Claim 18
Dependent Claim
39 words
A curable composition of claim 16, wherein each of Y 1 , Y 2 , and Y 3 in formula [I] is a residue represented by the formula ##STR52## wherein m is 0 or 1 and Y" is ##STR53##
Claim 19
Dependent Claim
19 words
A curable composition of claim 1, which comprises further a compound having at least one active carbon-carbon double bond.
Claim 20
Dependent Claim
12 words
A curable composition of claim 18, which comprises further a polyacrylate compound.
Claim 21
Dependent Claim
25 words
A curable composition of claim 19, which comprises further a compound represented by the formula ##STR54## wherein n is a number of 1 to 20.
Claim 22
Dependent Claim
12 words
A curable composition of claim 20, which comprises further tetraethylene glycol diacrylate.
Claim 23
Dependent Claim
30 words
A curable composition of claim 1, which comprises further an imide compound represented by the formula ##STR55## wherein R 8 is an organic residue containing no reactive carbon-carbon double bond.
Claim 24
Dependent Claim
94 words
A curable composition of claim 1, which comprises further a photosensitive polyimide precursor consisting of recurring units represented by the formula ##STR56## wherein, X is a (2+n)-valent carbocyclic or heterocyclic residue, Y is a (2+m)-valent carbocyclic or heterocyclic residue, Z is ##STR57## R is hydrogen or a hydrocarbon residue, W is a residue which, on heat treatment, reacts with the carbonyl of COOR to release ROH and form a ring, n is 1 or 2, m is 0, 1, or 2, and COOR and Z are at positions ortho or peri to each other.
Claim 25
Dependent Claim
39 words
A curable composition of claim 1, wherein said polymerization initiator is an oxime initiator represented by the formula ##STR58## wherein each of R 9 , R 10 , and R 11 is a residue containing no reactive carbon-carbon bond.
Claim 26
Dependent Claim
13 words
A curable composition of claim 24, in which said polymerization initiator is 1,3-diphenylpropanetrione-2-(o-ethoxycarbonyl)oxime.
Claim 27
Dependent Claim
28 words
A curable composition of claim 1, wherein the content of the polymerization initiator is from 0.1 to 15% by weight based on the polyimide used as component (a).
Claim 28
Dependent Claim
28 words
A curable composition of claim 26, wherein the content of the polymerization initiator is from 0.1 to 10% by weight based on the polyimide used as component (a).
Claim 29
Dependent Claim
34 words
A curable composition of claim 18, wherein the content of the compound having at least one active carbon-carbon double bond is up to 20% by weight based on the polyimide used as component (a).
Claim 30
Dependent Claim
28 words
A curable composition of claim 23, wherein the content of the photosensitive polyimide precursor is up to 50% by weight based on the polyimide used as component (a).
Claim 31
Dependent Claim
47 words
A curable composition of claim 1, which comprises further as a sensitizer a combination of bis(dialkylamino)benzophenone, a mercapto-containing aromatic heterocyclic compound, and a compound represented by the formula ##STR59## wherein R 12 is hydrogen or an aliphatic or aromatic residue which may or may not contain hydroxyl(s).
Claim 32
Dependent Claim
18 words
A curable composition of claim 30, in which said sensitizer is a combination of 4,4'-bis(diethylamino)benzophenone, 1-phenyl-5-mercapto-1H-tetrazole, and N-phenylethanolamine.
Claim 33
Dependent Claim
11 words
A heat-resistant film prepared from the curable composition of claim 1.
Claim 34
Dependent Claim
174 words
A composition of claim 1 comprising (a), (b) and, optionally, (c), wherein (c) is a member selected from the group consisting of a compound having at least one active carbon-carbon double bond; an imide compound of the formula ##STR60## wherein R 8 is an organic residue containing no reactive carbon-carbon double bond; a photosensitive polyimide precursor consisting of recurring units represented by the formula ##STR61## wherein, X is a (2+n)-valent carbocyclic or heterocyclic residue, Y is a (2+m)-valent carbocyclic or heterocyclic residue, Z is ##STR62## R is hydrogen or a hydrocarbon residue, W is a residue which, on heat treatment, reacts with the carbonyl of COOR to release ROH and form a ring, n is 1 or 2, m is 0, 1, or 2, and COOR and z are at positions ortho or peri to each other; and a sensitizer combination of bis-(dialkylamino)benzophenone, a mercapto-containing aromatic heterocyclic compound, and a compound represented by the formula ##STR63## wherein R 12 is hydrogen or an aliphatic or aromatic residue which may or may not contain hydroxyl(s).
Claim 35
Dependent Claim
22 words
A heat-resistant film, the structure of which is that of a cured composition wherein the composition is a composition of claim 1.
References Cited (Backward Citations)
US3528950A
Cited
US3708459A
Cited
US3781247A
Cited
US4321319A
Cited
US4481340A
Cited
EP0131992A1
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1991-10-18 | 1992-04-18 | 1992-10-18 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1995-10-18 | 1996-04-18 | 1996-10-18 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1999-10-18 | 2000-04-18 | 2000-10-18 | $7700.00 | Window Closed / Lapsed |