US4310641A
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Heat resistant photoresist composition and process for preparing the same
Assignee: Asahi Kasei Corp
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Filing: 1979-08-01
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Granted: 1982-01-12
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Expires: 1999-08-01
Abstract
Abstract An organic polar solvent-soluble aromatic polyamide-imide having therein aromatic nuclei linked at their respective 1 - and 3 -positions and having therein amide linkages and terminal groups partially substituted with cinnamate groups is found to impart excellent heat resistance and insulating property to a photoresist composition produced therefrom.
Inventors
- 👤 Kaoru Ohmura
- 👤 Ichiro Shibasaki
- 👤 Takeo Kimura
- 👤 Muneaki Kimura
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 23:35
CPC Classifications
C; C08; C08G; C08G73/00; C08G73/06; C08G73/10; C08G73/14; G; G03; G03F; G03F7/00; G03F7/004; G03F7/027; G03F7/032; G03F7/037; G03F7/038; G03F7/0387
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
328 words
A polymer selected from the group consisting of a polymer (α) of the general formula ##STR29## a polymer (β) of the general formula ##STR30## a polymer (γ) of the general formula ##STR31## and mixtures thereof wherein R 1 to R 6 are the same or different and each represent a hydrogen atom, a (C 1 -C 4 ) alkyl group or a halogen atom, Ar represents ##STR32## wherein R 7 to R 15 are the same or different and each have the same meaning as defined with respect to R 1 to R 6 and X 1 to X 4 are the same or different and each represent --O--, --SO 2 --, --CH 2 --, --CO--, --COO--, --C(CH 3 ) 2 --, --S-- or --(CH 2 ) 2 --, Ar' represents ##STR33## wherein R 16 to R 20 are the same or different and each have the same meaning as defined with respect to R 1 to R 6 and X 5 has the same meaning as defined with respect to X 1 to X 4 , Ar" has the same meaning as defined with respect to Ar or Ar', B 1 to B 4 are the same or different and each represent --NCO or a substituent (A) formed by the reaction of --NCO with cinnamic acid or cinnamyl alcohol, each Q independently represents a hydrogen atom or a substituent (A'), provided that each of the rates of substituent introduction into the molecules of the polymers (α), (β) and (γ) as defined by the formulae ##EQU3## with respect to the polymer (α), the polymer (β), and the polymer (γ), respectively, is 0.1 to 50%, said substituent (A') being a member selected from residual groups of cinnamoyl chloride and glycidyl cinnamate, said residual groups being introduced alone or in combination, and m, n and p are integers corresponding to reduced viscosities of 0.1 to 2.0 with respect to the polymer (α) the polymer (β) and the polymer (γ), respectively.
Claim 2
Dependent Claim
328 words
A polymer selected from the group consisting of a polymer (α) of the general formula ##STR29## a polymer (β) of the general formula ##STR30## a polymer (γ) of the general formula ##STR31## and mixtures thereof wherein R 1 to R 6 are the same or different and each represent a hydrogen atom, a (C 1 -C 4 ) alkyl group or a halogen atom, Ar represents ##STR32## wherein R 7 to R 15 are the same or different and each have the same meaning as defined with respect to R 1 to R 6 and X 1 to X 4 are the same or different and each represent --O--, --SO 2 --, --CH 2 --, --CO--, --COO--, --C(CH 3 ) 2 --, --S-- or --(CH 2 ) 2 --, Ar' represents ##STR33## wherein R 16 to R 20 are the same or different and each have the same meaning as defined with respect to R 1 to R 6 and X 5 has the same meaning as defined with respect to X 1 to X 4 , Ar" has the same meaning as defined with respect to Ar or Ar', B 1 to B 4 are the same or different and each represent --NCO or a substituent (A) formed by the reaction of --NCO with cinnamic acid or cinnamyl alcohol, each Q independently represents a hydrogen atom or a substituent (A'), provided that each of the rates of substituent introduction into the molecules of the polymers (α), (β) and (γ) as defined by the formulae ##EQU3## with respect to the polymer (α), the polymer (β), and the polymer (γ), respectively, is 0.1 to 50%, said substituent (A') being a member selected from residual groups of cinnamoyl chloride and glycidyl cinnamate, said residual groups being introduced alone or in combination, and m, n and p are integers corresponding to reduced viscosities of 0.1 to 2.0 with respect to the polymer (α) the polymer (β) and the polymer (γ), respectively.
Claim 3
Dependent Claim
18 words
A polymer of the general formula: ##STR34## where Q, m, and Ar are as defined in claim 1.
Claim 4
Dependent Claim
29 words
A polymer of the general formula: ##STR35## where R 1 to R 4 , B 1 , Q, Ar', n and B 2 are as defined in claim 1.
Claim 5
Dependent Claim
30 words
A polymer of the general formula: ##STR36## where B 3 , B 4 , Ar", Q, R 5 , R 6 , and p are as defined in claim 1.
Claim 6
Dependent Claim
301 words
A process for the preparation of a polymer which comprises: reacting an organic polar solvent-soluble aromatic polyamide-imide having aromatic nuclei linked at their respective 1- and 3-positions and selected from the group consisting of a polyamide-imide (α') of the general formula ##STR37## a polyamide-imide (β') of the general formula ##STR38## a polyamide-imide (γ') of the general formula ##STR39## and mixtures thereof wherein R 1 to R 6 are the same or different and each represent a hydrogen atom, a (C 1 -C 4 ) alkyl group or a halogen atom, Ar represents ##STR40## wherein R 7 to R 15 are the same or different and each have the same meaning as defined with respect to R 1 to R 6 and X 1 to X 4 are the same or different and each represent --O--, --SO 2 --, --CH 2 --, --CO--, --COO--, --C(CH 3 ) 2 --, --S-- or --(CH 2 ) 2 --, Ar' represents ##STR41## wherein R 16 to R 20 are the same or different and each have the same meaning as defined with respect to R 1 to R 6 and X 5 has the same meaning as defined with respect to X 1 to X 4 , Ar" has the same meaning as defined with respect to Ar or Ar', and m', n' and p' are integers corresponding to reduced viscosities of 0.1 to 2.0 with respect to the polyamide-imide (α'), the polyamide-imide (β'), and the polyamide-imide (γ'), respectively, with a reactant selected from the group consisting of cinnamoyl chloride, glycidyl cinnamate, cinnamic acid, cinnamyl alcohol, and mixtures thereof, with the proviso, however, that when the organic polar solvent-soluble aromatic polyamide-imide is the polyamide-imide (α'), the reactant group does not include cinnamyl alcohol, in the presence of an organic polar solvent, to produce a polymer.
Claim 7
Dependent Claim
301 words
A process for the preparation of a polymer which comprises: reacting an organic polar solvent-soluble aromatic polyamide-imide having aromatic nuclei linked at their respective 1- and 3-positions and selected from the group consisting of a polyamide-imide (α') of the general formula ##STR37## a polyamide-imide (β') of the general formula ##STR38## a polyamide-imide (γ') of the general formula ##STR39## and mixtures thereof wherein R 1 to R 6 are the same or different and each represent a hydrogen atom, a (C 1 -C 4 ) alkyl group or a halogen atom, Ar represents ##STR40## wherein R 7 to R 15 are the same or different and each have the same meaning as defined with respect to R 1 to R 6 and X 1 to X 4 are the same or different and each represent --O--, --SO 2 --, --CH 2 --, --CO--, --COO--, --C(CH 3 ) 2 --, --S-- or --(CH 2 ) 2 --, Ar' represents ##STR41## wherein R 16 to R 20 are the same or different and each have the same meaning as defined with respect to R 1 to R 6 and X 5 has the same meaning as defined with respect to X 1 to X 4 , Ar" has the same meaning as defined with respect to Ar or Ar', and m', n' and p' are integers corresponding to reduced viscosities of 0.1 to 2.0 with respect to the polyamide-imide (α'), the polyamide-imide (β'), and the polyamide-imide (γ'), respectively, with a reactant selected from the group consisting of cinnamoyl chloride, glycidyl cinnamate, cinnamic acid, cinnamyl alcohol, and mixtures thereof, with the proviso, however, that when the organic polar solvent-soluble aromatic polyamide-imide is the polyamide-imide (α'), the reactant group does not include cinnamyl alcohol, in the presence of an organic polar solvent, to produce a polymer.
Claim 8
Dependent Claim
127 words
A polymer of the general formula ##STR42## wherein Ar represents ##STR43## wherein R 7 to R 15 are the same or different and each represents a hydrogen atom, a (C 1 -C 4 ) alkyl group or a halogen atom and X 1 to X 4 are the same or different and each represents --O--, --SO 2 --, --CH 2 --, --CO--, --COO--, --C(CH 3 ) 2 --, --S-- or --(CH 2 ) 2 --, Q represents a hydrogen atom and a substituent (A'), provided that the rate of substituent introduction into the molecule of the polymer defined by the formula ##EQU4## is 0.1 to 50%, said substituent (A') being a cinnamoyl group, and m corresponds to a reduced viscosity of the polymer of 0.1 to 2.0.
Claim 9
Dependent Claim
127 words
A polymer of the general formula ##STR42## wherein Ar represents ##STR43## wherein R 7 to R 15 are the same or different and each represents a hydrogen atom, a (C 1 -C 4 ) alkyl group or a halogen atom and X 1 to X 4 are the same or different and each represents --O--, --SO 2 --, --CH 2 --, --CO--, --COO--, --C(CH 3 ) 2 --, --S-- or --(CH 2 ) 2 --, Q represents a hydrogen atom and a substituent (A'), provided that the rate of substituent introduction into the molecule of the polymer defined by the formula ##EQU4## is 0.1 to 50%, said substituent (A') being a cinnamoyl group, and m corresponds to a reduced viscosity of the polymer of 0.1 to 2.0.
Claim 10
Dependent Claim
130 words
A process for the preparation of a polymer which comprises: reacting an organic polar solvent-soluble aromatic polyamide-imide having aromatic nuclei linked at their respective 1- and 3-positions and represented by the general formula ##STR44## wherein Ar represents ##STR45## wherein R 7 to R 15 are the same or different and each represents a hydrogen atom, a (C 1 -C 4 ) alkyl group or a halogen atom, X 1 to X 4 are the same or different and each represents --O--, --SO 2 --, --CH 2 --, --CO--, --COO--, --C(CH 3 ) 2 --, --S-- or --(CH 2 ) 2 --, and m' corresponds to a reduced viscosity of the polyamide-imide of 0.1 to 2.0, with cinnamoyl chloride, in the presence of an organic polar solvent, to produce a polymer.
Claim 11
Dependent Claim
130 words
A process for the preparation of a polymer which comprises: reacting an organic polar solvent-soluble aromatic polyamide-imide having aromatic nuclei linked at their respective 1- and 3-positions and represented by the general formula ##STR44## wherein Ar represents ##STR45## wherein R 7 to R 15 are the same or different and each represents a hydrogen atom, a (C 1 -C 4 ) alkyl group or a halogen atom, X 1 to X 4 are the same or different and each represents --O--, --SO 2 --, --CH 2 --, --CO--, --COO--, --C(CH 3 ) 2 --, --S-- or --(CH 2 ) 2 --, and m' corresponds to a reduced viscosity of the polyamide-imide of 0.1 to 2.0, with cinnamoyl chloride, in the presence of an organic polar solvent, to produce a polymer.
Claim 12
Dependent Claim
30 words
A process according to claim 7, wherein said cinnamoyl chloride is used in an amount of 0.001 to 10 moles per mole of the polymeric unit of the aromatic polyamide-imide.
Claim 13
Dependent Claim
27 words
A process according to claims 7 or 8, wherein the reaction is carried out at a temperature of 0° to 150° C. for 1 to 24 hours.
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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) | 1985-01-11 | 1985-07-13 | 1986-01-12 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-01-11 | 1989-07-13 | 1990-01-12 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-01-11 | 1993-07-13 | 1994-01-12 | $7700.00 | Window Closed / Lapsed |