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US4025348A Expired / Lapsed US ⏱️ 0.0 years remaining

Photosensitive resin compositions

Assignee: Resonac Corp
•
Filing: 1975-05-05
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Granted: 1977-05-24
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Expires: 1995-05-05
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Abstract

Abstract A photosensitive resin composition consisting essentially of (A) a photo-polymerizable unsaturated compound having at least two terminal ethylene groups, (B) a reactive linear high molecular weight compound having in its side chain one or two functional groups selected from the class consisting of tetrahydrofurfuryl group and N-alkoxymethylcarbamoyl group, (C) a sensitizer capable of initiating polymerization of the above unsaturated compound upon irradiation with active rays, (D) a compound having at least two epoxy groups, and (E) a potential or latent curing agent for epoxy resins. The photosensitive resin composition can give a protective film excellent in solvent resistance, chemical resistance, heat resistance and mechanical strengths, and hence can be used in the production of printed circuit boards and the precision-processing of metals.

Inventors

  • 👤 Katsushige Tsukada
  • 👤 Asao Isobe
  • 👤 Toshiaki Ishimaru
  • 👤 Nobuyuki Hayashi
  • 👤 Masahiro Abo

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-26 19:00
CPC Classifications
G; G03; G03F; G03F7/00; G03F7/004; G03F7/038; G03F7/027; G03F7/032; Y; Y10; Y10S; Y10S430/00; Y10S430/1053; Y10S430/1055; Y10S430/106; Y10S430/114; Y10S430/115; Y10S430/117

Claims Analysis

Total Claims: 23
Claim 1
Independent Claim 96 words
A photosensitive resin composition which consists essentially of the following components: (A) a photopolymerizable unsaturated compound containing at least two terminal ethylene groups, (B) a reactive linear high molecular weight compound other than component (A) having in its side chain one or two functional groups selected from the class consisting of tetrahydrofurfuryl group and N-alkoxymethylcarbamoyl group, (C) a sensitizer capable of initiating polymerization of the unsaturated compound upon irradiation with active rays, (D) a compound other than components (A) and (B) having at least two epoxy groups, and (E) a latent curing agent for epoxy resins.
Claim 2
Dependent Claim 96 words
A photosensitive resin composition which consists essentially of the following components: (A) a photopolymerizable unsaturated compound containing at least two terminal ethylene groups, (B) a reactive linear high molecular weight compound other than component (A) having in its side chain one or two functional groups selected from the class consisting of tetrahydrofurfuryl group and N-alkoxymethylcarbamoyl group, (C) a sensitizer capable of initiating polymerization of the unsaturated compound upon irradiation with active rays, (D) a compound other than components (A) and (B) having at least two epoxy groups, and (E) a latent curing agent for epoxy resins.
Claim 3
Dependent Claim 24 words
A photosensitive resin composition according to claim 1, wherein the photo-polymerizable unsaturated compound is an acrylic or methacrylic acid ester of a polyhydric alcohol.
Claim 4
Dependent Claim 26 words
A photosensitive resin composition according to claim 2, wherein the polyhydric alcohol is ethylene glycol, triethylene glycol, tetraethylene glycol, propylene glycol, trimethylolpropane, pentaerythritol or neopentyl glycol.
Claim 5
Dependent Claim 28 words
A photosensitive resin composition according to claim 1, wherein the photo-polymerizable unsaturated compound is an acrylic or methacrylic acid ester of an alkylene oxide adduct of bisphenol A.
Claim 6
Dependent Claim 29 words
A photosensitive resin composition according to claim 1, wherein the content of the photo-polymerizable unsaturated compound is 15 to 60% by weight based on the weight of the composition.
Claim 7
Dependent Claim 76 words
A photosensitive resin composition according to claim 1, wherein the reactive linear high molecular weight compound is a polymer of at least one monomer selected from the group consisting of monomers represented by the formulas, ##STR3## wherein R is hydrogen, methyl or ethyl, or ##STR4## wherein R is hydrogen or a C 1-4 alkyl and R' is hydrogen, a C 1-4 alkyl, nitrile or a halogen, or a copolymer of said monomer with another vinyl monomer.
Claim 8
Dependent Claim 32 words
A photosensitive resin composition according to clain 5, wherein the content of the reactive linear high molecular weight compound is 20 to 70% by weight based on the weight of the composition.
Claim 9
Dependent Claim 32 words
A photosensitive resin composition according to clain 5, wherein the content of the reactive linear high molecular weight compound is 20 to 70% by weight based on the weight of the composition.
Claim 10
Dependent Claim 24 words
A photosensitive resin composition according to claim 1, wherein the sensitizer is benzophenone, Michler's ketone, benzoin, a benzoin alkyl ether, 2-ethylanthraquinone, 3-t-butylanthraquinone or benzil.
Claim 11
Dependent Claim 27 words
A photosensitive resin composition according to claim 7, wherein the content of the sensitizer is 0.1 to 15% by weight based on the weight of the composition.
Claim 12
Dependent Claim 40 words
A photosensitive resin composition according to claim 1, wherein the compound having at least two epoxy groups is a novolac type epoxy resin prepolymer and its content is 5 to 50% by weight based on the weight of the composition.
Claim 13
Dependent Claim 56 words
A photosensitive resin composition according to claim 1, wherein the curing agent is a compound selected from the group consisting of boron trifluoride-amine complexes, amine tetrafluoroborates, dibasic acid hydrazides, alkylamine boranes, aromatic amine-inorganic acid complexes, extra-coordination silicates, dicyandiamide and N,N-diallylmelamine, and its content is 0.1 to 20% by weight based on the weight of the composition.
Claim 14
Dependent Claim 27 words
A photosensitive resin composition according to claim 1, wherein a thermal polymerization inhibitor, a plasticizer, a dye, a pigment and/or a filler is used as auxiliary components.
Claim 15
Dependent Claim 82 words
A photosensitive resin composition according to claim 1, wherein the content of the photo-polymerizable unsaturated compound is 10 to 90% by weight, the content of the reactive linear high molecular weight compound is 10-80% by weight, the content of the sensitizer is 0.1-15% by weight, the content of the compound having at least two epoxy groups is 5-80% by weight, and the content of the curing agent is from 0.2-12% by weight, said contents being based on the weight of the composition.
Claim 16
Dependent Claim 91 words
A photosensitive resin composition according to claim 1, wherein the photo-polymerizable unsaturated compound is an acrylic or methacrylic acid ester of a polyhydric alcohol; an acrylic or methacrylic acid ester of a bisphenol A-epichlorohydrin epoxy resin prepolymer; an acrylic or methacrylic acid ester of an alkylene oxide adduct of bisphenol A; methylene-bis-acrylamide, methylene-bis-methacrylamide, bis-acryl- or bis-methacryl-amide of a diamine; reaction product of diol monoacrylate or diol methacrylate with diisocyanate and triacryl formal or triallyl cyanurate; or a linear high molecular weight compound containing acryloyloxy or methacryloyloxy group in a side chain.
Claim 17
Dependent Claim 59 words
A photosensitive resin composition according to claim 1, wherein the reactive linear molecular weight compound comprises N-n-butoxymethylacrylamide-tetrahydrofurfuryl methacrylate copolymer, N-ethoxymethylacrylamide-tetrahydrofurfuryl methacrylate-methyl methacrylate copolymer, N-methoxymethylacrylamide-tetrahydrofurfuryl methacrylate-styrene copolymer, N-n-butoxymethylmethacrylamide-tetrahydrofurfuryl methacrylate-acrylonitrile copolymer, N-n-butoxymethylacrylamide-tetrahydrofurfuryl methacrylate-styrene-acrylonitrile copolymer, N-n-butoxy-methylacrylamide-methyl methacrylate copolymer, N-n-propoxyacrylamide-methyl methacrylate copolymer, N-n-butoxymethylmethacrylamide-ethyl methacrylate copolymer, N-n-butoxymethylacrylamide-acrylonitrile-styrene-methyl methacrylate copolymer, tetrahydrofurfuryl acrylate polymer, tetrahydrofurfuryl methacrylate polymer, tetrahydrofurfuryl acrylate-vinyl compound copolymer, and tetrahydrofurfuryl methacrylate-vinyl compound copolymer.
Claim 18
Dependent Claim 30 words
A photosensitive resin composition according to claim 1, wherein the compound having at least two epoxy compounds is an epoxy resin prepolymer or a vinyl copolymerization product of glycidyl methacrylate.
Claim 19
Dependent Claim 233 words
A photosensitive resin composition which consists essentially of (A) a photo-polymerizable unsaturated compound containing at least two terminal ethylene groups selected from the group consisting of acrylic or methacrylic acid ester of a polyhydric alcohol; an acrylic or methacrylic acid ester of a bisphenol A-epichlorohydrin epoxy resin prepolymer; an acrylic or methacrylic acid ester of an alkylene oxide adduct of bisphenol A; methylene-bis-acrylamide, methylene-bis-methacrylamide, bis-acryl- or bis-methacryl-amide of a diamine; reaction product of diol monoacrylate or diol methacrylate with diisocyanate and triacryl formal or triallyl cyanurate; and a linear high molecular weight compound containing acryloyloxy or methacryloyloxy group in a side chain, (B) a reactive linear high molecular weight compound having in its side chain one or two functional groups selected from the class consisting of tetrahydrofurfuryl group and N-alkoxymethylcarbamoyl group comprising a polymer of at least one monomer selected from the group consisting of monomers represented by the formulae: ##STR5## wherein R is hydrogen, methyl or ethyl, or ##STR6## wherein R is hydrogen or a C 1-4 alkyl and R' is hydrogen, a C 1-4 alkyl, nitrile or a halogen, or a copolymer of said monomer with another vinyl monomer, (C) a synthesizer selected from the group consisting of benzophenone, Michler's ketone, benzoin, a benzoin alkyl ether, 2-ethyl-anthraquinone, 3-t-butylanthraquinone and benzil, and (D) an epoxy resin having at least two epoxy groups and (E) a latent curing agent for said epoxy resin.
Claim 20
Dependent Claim 233 words
A photosensitive resin composition which consists essentially of (A) a photo-polymerizable unsaturated compound containing at least two terminal ethylene groups selected from the group consisting of acrylic or methacrylic acid ester of a polyhydric alcohol; an acrylic or methacrylic acid ester of a bisphenol A-epichlorohydrin epoxy resin prepolymer; an acrylic or methacrylic acid ester of an alkylene oxide adduct of bisphenol A; methylene-bis-acrylamide, methylene-bis-methacrylamide, bis-acryl- or bis-methacryl-amide of a diamine; reaction product of diol monoacrylate or diol methacrylate with diisocyanate and triacryl formal or triallyl cyanurate; and a linear high molecular weight compound containing acryloyloxy or methacryloyloxy group in a side chain, (B) a reactive linear high molecular weight compound having in its side chain one or two functional groups selected from the class consisting of tetrahydrofurfuryl group and N-alkoxymethylcarbamoyl group comprising a polymer of at least one monomer selected from the group consisting of monomers represented by the formulae: ##STR5## wherein R is hydrogen, methyl or ethyl, or ##STR6## wherein R is hydrogen or a C 1-4 alkyl and R' is hydrogen, a C 1-4 alkyl, nitrile or a halogen, or a copolymer of said monomer with another vinyl monomer, (C) a synthesizer selected from the group consisting of benzophenone, Michler's ketone, benzoin, a benzoin alkyl ether, 2-ethyl-anthraquinone, 3-t-butylanthraquinone and benzil, and (D) an epoxy resin having at least two epoxy groups and (E) a latent curing agent for said epoxy resin.
Claim 21
Dependent Claim 25 words
A photosensitive resin composition according to claim 17, wherein the epoxy resin is an epoxy resin prepolymer or a vinyl copolymerization product of glycidyl methacrylate.
Claim 22
Dependent Claim 40 words
A photosensitive resin composition according to claim 18, wherein the curing agent is a compound selected from the group consisting of boron trifluoride-amine complexes, amine tetrafluoroborates, dibasic acid hydrazides, alkylamine boranes, aromatic amine-inorganic acid complexes, extra-coordination silicates, dicyandiamide and N,N-diallylmelamine.
Claim 23
Dependent Claim 82 words
A photosensitive resin composition according to claim 19, wherein the content of the photo-polymerizable unsaturated compound is 10 to 90% by weight, the content of the reactive linear high molecular weight compound is 10-80% by weight, the content of the sensitizer is 0.1-15% by weight, the content of the compound having at least two epoxy groups is 5-80% by weight, and the content of the curing agent is from 0.2-12% by weight, said contents being based on the weight of the composition.

References Cited (Backward Citations)

US3380831A Cited
US3486903A Cited
US3796578A Cited
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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) 1980-05-23 1980-11-22 1981-05-24 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1984-05-23 1984-11-22 1985-05-24 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1988-05-23 1988-11-22 1989-05-24 $7700.00 Window Closed / Lapsed

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