EP0307752A2
Expired / Lapsed
EP
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Poly(3-mono- and 3,5-disubstituted-4-acetoxystyrenes and 4-hydroxy-styrenes)and their use
Assignee: Hoechst AG
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Filing: 1988-09-05
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Granted: —
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Expires: 2008-09-05
Abstract
Abstract The invention provides poly(3-mono- and 3,5-disubstituted-4-acetoxy- and 4-hydroxystyrenes) and copolymers therefrom having a molecular weight in the range of from about 1,000 to about 800,000 wherein said 3-mono and 3,5-substitution is independently C₁ to C₁₀ alkyl or alkoxy, primary or secondary amino, halogen (Br, Cl, I), NO₂ or SO₃H. The polymers are used as a binder resin in photosensitive compositions, wherein the light-sensitive compound is an o-quinone diazide or as an acid-forming radiation-sensitive compound in combination with a compound cleavable by acid.
Inventors
- 👤 Richard Dipl.-Chem. Vicari
- 👤 Douglas J. Dipl.-Chem. Gordon
- 👤 Raymond W. Dipl.-Chem. Rupp
- 👤 Ralph Dr. Dipl.-Chem. Dammel
- 👤 Karl-Friedrich Dr. Dipl.-Chem. Dössel
- 👤 Jürgen Dr. Dipl.-Chem. Lingnau
- 👤 James P. Dipl.-Chem. Lockard
- 👤 Mohammed Dipl.-Chem. Aslam
- 👤 Wilson B. Dipl.-Chem. Ray
- 👤 Kenneth G. Dipl.-Chem. Davenport
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-09 03:45
CPC Classifications
C; C08; C08F; C08F12/00; C08F12/02; C08F12/04; C08F12/14; C08F12/22; G; G03; G03F; G03F7/00; G03F7/004; G03F7/022; G03F7/023; G03F7/0233
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
49 words
Poly(3-mono- und 3,5-disubstituted-4-acetoxy- and -4-hydroxystyrenes) and copolymers therefrom having a molecular weight in the range of from about 1,000 to about 800,000 wherein said 3-mono- and 3,5-substitution is independently C₁ to C₁₀ alkyl or C₁ to C₁₀ alkoxy, primary or secondary amine, halogen, (Br, Cl, I), NO₂ or SO₃H.
Claim 2
Dependent Claim
49 words
Poly(3-mono- und 3,5-disubstituted-4-acetoxy- and -4-hydroxystyrenes) and copolymers therefrom having a molecular weight in the range of from about 1,000 to about 800,000 wherein said 3-mono- and 3,5-substitution is independently C₁ to C₁₀ alkyl or C₁ to C₁₀ alkoxy, primary or secondary amine, halogen, (Br, Cl, I), NO₂ or SO₃H.
Claim 3
Dependent Claim
33 words
Polymer according to claim 1, wherein the positions 3- or 3 and 5 have been substituted independently by C₁ to C₁₀ alkyl or alkoxy, in particular methyl, primary or secondary amine or halogen.
Claim 4
Dependent Claim
88 words
Polymer and copolymer according to claim 1, wherein the substitutes on position 3 or 3 and 5 are alkyl or halogen and the polymer and/or copolymer containing units of general formula I wherein R is hydrogen or acetyl, Hal is chlorine or bromine, R₁ is hydrogen, alkyl, or halogen; and R₂ and R₃ are independently hydrogen, alkyl, alkoxy, or halogen, where R₁ and R₂, provided R₁ is alkyl, can also be combined to form a cycloaliphatic ring consisting particularly of 6 to 12 members; in particular carbon atoms.
Claim 5
Dependent Claim
25 words
Polymer and copolymer according to claim 3, wherein Hal is bromine, R₁ is (C₁-C₃) alkyl, and R₂ and R₃ are hydrogen; and R is hydrogen.
Claim 6
Dependent Claim
135 words
Copolymer according to claims 1 and 2, wherein said copolymer is of general formula III wherein R is hydrogen or acetyl, in particular acetyl, X is C₁ to C₁₀ alkyl, C₁ to C₁₀ alkoxy amine, Br, I, Cl, NO₂ or SO₃H, and Y is 4-acetoxy- or -4-hydroxystyrene, styrene, an acrylate or methacrylate, 3,5-di-X-substituted-4-acetoxy- or 4-hydroxystyrene, maleic anhydride or N-substituted maleimides wherein the N-substituents are selected from the group consisting of aliphatic, cycloaliphatic or heterocyclic groups and Z is absent or is selected from 4-acetoxy- or 4-hydroxystyrene, styrene, an acrylate or methacrylate, 3,5-di-X-substituted-4-acetoxy- or -4-hydroxystyrene, maleic anhydride or N-substituted maleimides wherein said N-substitution is selected from the group consisting of aliphatic, cycloaliphatic or heterocyclic groups; and wherein said copolymer or terpolymer has an average molecular weight in the range of from about 1,000 to about 800,000.
Claim 7
Dependent Claim
57 words
Copolymer according to claims 1 and 2, wherein said copolymer is of general formula IV wherein R is hydrogen or acetyl, in particular hydrogen; and X is independently C₁ to C₁₀ alkyl, Br, I, Cl, NO₂ or SO₃H; and wherein the copolymer has an average molecular weight in the range of from about 1,000 to about 800,000.
Claim 8
Dependent Claim
21 words
Copolymer according to claims 3 and 4, wherein the copolymer comprises at least 10 % of units with general formula I.
Claim 9
Dependent Claim
37 words
A photosensitive composition which comprises as a light-sensitive compound an o-quinonediazide, a solvent and a binder, wherein said binder is a polymer according to claim 1 or 2 or a copolymer according to claim 5 or 6.
Claim 10
Dependent Claim
22 words
Photosensitive composition according to claim 8, wherein said photosensitizer is a condensation product of a 1,2-naphthoquinone-2-diazide-4- or 5-sulfonyl compound with a hydroxybenzophenone.
Claim 11
Dependent Claim
30 words
Photosensitive composition according to claims 8 and 9, wherein the ratio by weight of said polymer to said photosensitizer is in the range of from about 1:1 to about 20:1.
Claim 12
Dependent Claim
126 words
Photosensitive composition according to claims 8 to 11, wherein a crosslinker of the general formula (R₄O-CHR₆) n -A-(CHR₇-OR₅) m is included wherein A has the formula B-Y-B, wherein B is a substituted or unsubstituted mononuclear or fused polynuclear aromatic hydrocarbon or an oxygen or sulfur containing heterocyclic compound, Y is a single bond, C₁-C₄-alkylene or alkylene dioxy, the chains of which may be interrupted by oxygen atoms, -O-, -S-, -SO₂-, -CO-, -CO₂-, -O-CO₂-, -CONH-, or phenylene dioxy, R₄ and R₅ independently are H, C₁-C₆ alkyl, cycloalkyl, substituted or unsubstituted aryl, alkaryl or acyl, R₆ and R₇ are independently H, C₁-C₄ alkyl or substituted or unsubstituted phenyl, n ranges from 1 to 3 and m ranges from 0 to 3, provided that n+m is greater than 1.
Claim 13
Dependent Claim
24 words
A photographic element comprising a photosensitive composition and a support, wherein said photosensitive composition is a dried composition according to claims 8 to 11.
Claim 14
Dependent Claim
57 words
A process for forming a photographic image which comprises coating the photographic composition of claims 8 to 11 on a support, drying the composition until it is substantially non-tacky; imagewise exposing the composition to sufficient actinic, electron beam or x-ray radiation to provide an imagwise differentiation, and removing the non-image portions of said composition with a developer.
Claim 15
Dependent Claim
39 words
A positive-working radiation-sensitive mixture which comprises a radiation-sensitive polymer or copolymer (starter) forming an acid as well as a compound cleavable by acid, wherein the acid-forming compound is a polymer or copolymer according to claims 3, 4 and 7.
Claim 16
Dependent Claim
33 words
A positive-working radiation-sensitive mixture according to claim 14, wherein the polymeric starter being in the radiation-sensitive mixture in a percentage of about 2 to 100 %, based on the weight of the mixture.
Claim 17
Dependent Claim
31 words
A positive-working radiation-sensitive mixture according to claims 14 and 15 wherein the mixture contains a binder insoluble in water but soluble but at least swellable in aqueous alkalis and organic solvents.
Claim 18
Dependent Claim
27 words
A positive-working radiation-sensitve mixture according to claims 14 to 16, wherein the polymeric starter and the binder in the mixture are in approximately equal proportions by weight.
Claim 19
Dependent Claim
24 words
A positive-working recording material comprising a radiation-sensitive composition and a support, wherein said composition is a dried composition according to claims 14 to 16.
Claim 20
Dependent Claim
57 words
A method for manufacturing a positive-working recording material according to claim 18, wherein the support may be coated with an adhesion promoter, coating the support in the radiation-sensitive composition, drying the material and then irradiating the material with actinic radiation in the pattern of an image and then developing the imaged material with an aqueous alkali developer.
Claim 21
Dependent Claim
23 words
A method according to claim 19 wherein the resist structure is hardened at an elevated temperature and/or with UV light irradiation after development.
References Cited (Backward Citations)
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