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US4835193A Expired / Lapsed US ⏱️ 0.0 years remaining

Photopolymerizable epoxy resin composition

Assignee: Toshiba Corp
•
Filing: 1987-05-07
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Granted: 1989-05-30
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Expires: 2007-05-07
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Abstract

Abstract A photopolymerizable epoxy resin composition comprising (a) an epoxy resin and (b) a heteropoly-acid aromatic sulfonium salt or a heteropoly-acid aromatic iodonium salt as a photocuring catalyst exhibits rapid photopolymerization, with the cured product being great in hardness, the corrosive action being weak, and the electrical properties being excellent. The industrial utility of the composition is therefore substantial.

Inventors

  • 👤 Shuzi Hayase
  • 👤 Yasunobu Onishi
  • 👤 Shuichi Suzuki
  • 👤 Moriyasu Wada

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-01 00:18
CPC Classifications
G; G03; G03F; G03F7/00; G03F7/004; G03F7/038; C; C08; C08G; C08G59/00; C08G59/18; C08G59/68; C08G59/687; G03F7/0045; G03F7/027; G03F7/028; G03F7/029

Claims Analysis

Total Claims: 17
Claim 1
Independent Claim 307 words
A photopolyermizable epoxy resin composition comprising (A) an epoxy resin having more than one oxirane group and (B) a salt comprised of an anion of a heteropoly acid and an aromatic sulfonium or an aromatic iodonium cation, wherein (i) said anion is selected from the group consisting of a phosphotungstate anion, a phosphomolybdate anion, a tungstogermanate anion, silicotungstate anion and a silicomolybdate anion, and (ii) said salt is selected from the group consisting of (a) a compound represented by the formula: ##STR8## wherein Ar 1 to Ar 3 are the same or different from each other, and each represents an aromatic group which is unsubstituted or substituted with at least one substituent selected from the group consisting of a halogen atom, an alkyl group, an alkoxy group, an aralkyl group, an aryloxy group, an arylthio group and a nitro group; X m ⊖ represents said anion; and m is an integer of 3 to 5, and (b) a compound represented by the formula ##STR9## wherein Ar 4 and Ar 5 are the same or different from each other, and each represents a substituted or unsubstituted aromatic group or heterocyclic group having 6 to 20 carbon atoms; Z represents the optional presence of an oxygen atom, a sulfur atom, ##STR10## where R 1 represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms or an acyl group having 1 to 5 carbon atoms, and R 2 and R 3 are the same or different from each other, and each represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms or an alkenyl group having 2 to 4 carbon atoms; X m ⊖ represents said anion; m is the same as defined above; n is an integer of 0 or 1; and the dotted line represents the optional presence of bonding when n=1.
Claim 2
Dependent Claim 307 words
A photopolyermizable epoxy resin composition comprising (A) an epoxy resin having more than one oxirane group and (B) a salt comprised of an anion of a heteropoly acid and an aromatic sulfonium or an aromatic iodonium cation, wherein (i) said anion is selected from the group consisting of a phosphotungstate anion, a phosphomolybdate anion, a tungstogermanate anion, silicotungstate anion and a silicomolybdate anion, and (ii) said salt is selected from the group consisting of (a) a compound represented by the formula: ##STR8## wherein Ar 1 to Ar 3 are the same or different from each other, and each represents an aromatic group which is unsubstituted or substituted with at least one substituent selected from the group consisting of a halogen atom, an alkyl group, an alkoxy group, an aralkyl group, an aryloxy group, an arylthio group and a nitro group; X m ⊖ represents said anion; and m is an integer of 3 to 5, and (b) a compound represented by the formula ##STR9## wherein Ar 4 and Ar 5 are the same or different from each other, and each represents a substituted or unsubstituted aromatic group or heterocyclic group having 6 to 20 carbon atoms; Z represents the optional presence of an oxygen atom, a sulfur atom, ##STR10## where R 1 represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms or an acyl group having 1 to 5 carbon atoms, and R 2 and R 3 are the same or different from each other, and each represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms or an alkenyl group having 2 to 4 carbon atoms; X m ⊖ represents said anion; m is the same as defined above; n is an integer of 0 or 1; and the dotted line represents the optional presence of bonding when n=1.
Claim 3
Dependent Claim 80 words
The photoplymerizable epoxy resin composition according to claim 1, wherein the epoxy resin comprising at least one epoxy resin selected from the group consisting of a bisphenol A type epoxy resin, a bisphenol F type epoxy resin, a phenol-novolac type epoxy resin, an alicyclic epoxy resin, a heterocyclic ring-containing epoxy resin, a hydrogenated bisphenol A type epoxy resin, an aliphatic epoxy resin, a glycidyl ester type epoxy resin, a spiro ring-containing epoxy resin and a glycidyl ether type epoxy resin.
Claim 4
Dependent Claim 41 words
The photopolymerizable epoxy resin composition according to claim 1, wherein the heteropoly-acid aromatic sulfonium salt represents a compound selected from the group consisting of triphenylsulfonium phosphomolybdate, triphenylsulfonium phosphotungstate, triphenylsulfonium silicotungstate, tri(methyoxyphenyl)sulfonium phosphotungstate, tri(methyoxyphenyl)sulfonium silicomolybdate, tri(tert-butylphenyl)sulfonium phosphotungstate, tritolylsulfonium phosphotungstate and tri(2-naphthyl)sulfonium phosphotungstate.
Claim 5
Dependent Claim 43 words
The photopolymerizable epoxy resin composition according to claim 1, wherein the salt comprises a compound selected from the group consisting of diphenyliodonium phosphomolybdate, diphenyliodonium phosphotungstate, di(4-methylphenyl)-iodonium phosphosilicotungstate, di(4-heptylphenyl)iodonium tungstogermanate, di(5-nitrophenyl)iodonium phosphotungstate, di(4-chlorophenyl)iodonium silicomolybdate, dinaphthyliodonium phosphotungstate, di(4-trifluoromethylphenyl)iodonium phosphotungstate, di(benzothienyl) iodonium phosphotungstate and di(2-naphthyl)-sulfonium phosphotungstate.
Claim 6
Dependent Claim 36 words
The photopolymerizable epoxy resin composition according to claim 1, wherein the amount of salt is within the range of 0.001 to 10 parts by weight based on the 100 parts by weight of the epoxy resin.
Claim 7
Dependent Claim 37 words
The photopolymerizable epoxy resin composition according to claim 5, wherein the amount of the salt is within the range of 0.1 to 5 parts by weight based on the 100 parts by weight of the epoxy resin.
Claim 8
Dependent Claim 13 words
The photopolymerizable epoxy resin composition according to claim 1, further comprising a sensitizer.
Claim 9
Dependent Claim 29 words
The photopolymerizable epoxy resin composition according to claim 7, wherein the sensitizer comprises a compound selected from the group consisting of ##STR11## phenanthrene, naphthalene, 2-nitrofluorene, anthracene, benzoquinone and chrycene.
Claim 10
Dependent Claim 31 words
The photopolymerizable epoxy resin composition according to claim 7, wherein the amount of the sensitizer is within the range of 0.001 to 20 % by weight based on the epoxy resin.
Claim 11
Dependent Claim 40 words
The photopolymerizable epoxy resin composition according to claim 7, wherein the composition comprises an epoxy resin having more than one oxirane group; a salt comprised of an anion of a heteropoly acid and an aromatic iodonium cation; and a sensitizer.
Claim 12
Dependent Claim 14 words
The photopolymerizable epoxy resin composition according to claim 1, further comprising a quinone derivative.
Claim 13
Dependent Claim 139 words
The photopolymerizable epoxy resin composition according to claim 11, wherein the quione derivative comprises a compound represented by the formula: ##STR12## wherein R 4 , R 5 R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 and R 15 are the same or are different, and each represents a group selected from the group consisting of a hydrogen atom, a halogen atom, an alkyl group, a cyano group and a nitro group; or a pair selected from the group consisting of R 4 and R 5 , R 6 and R 7 , R 8 and R 9 , R 10 and R 11 , R 12 and R 13 , and R 14 and R 15 represents an aromatic condensed ring.
Claim 14
Dependent Claim 37 words
The photopolymerizable epoxy resin composition according to claim 11, wherein the quinone derivative comprises a compound selected from the group consisting of p-benzoquinone, o-benzoquinone, 1,4-naphthoquinone, 2-methyl-1,4-naphthoquinone, 2,3,5,6-tetrachloro-p-benzoquinone, anthraquinone, phenanthrenequinone, 2-methyl-anthraquinone, benzo anthraquinone, 1,2-dihydroxyanthraquinone, 4,4'-diphenoquinone, 3,3',5,5'-tetra-tert-butyl-4,4'-diphenoquinone and 3,3',5,5'-tetramethyl-4,4'-diphnoquinone.
Claim 15
Dependent Claim 38 words
The photopolymerizable epoxy resin composition according to claim 11, wherein the amount of the quinone derivative is within the range of 0.01 to 10 parts by weight based on the 100 parts by weight of the epoxy resin.
Claim 16
Dependent Claim 21 words
The photopolymerizable epoxy resin composition according to claim 11, wherein the composition comprises an aromatic iodonium salt of a heteropoly acid.
Claim 17
Dependent Claim 16 words
The photopolymerizable epoxy resin composition according to claim 1, wherein the salt is tri(methylphenyl) sulfonium phosphotungstate.

References Cited (Backward Citations)

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GB2034318A Cited
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EP0011918A2 Cited
US4196136A Cited
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US4495042A Cited
JPH118816A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1992-05-29 1992-11-28 1993-05-30 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1996-05-29 1996-11-28 1997-05-30 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2000-05-29 2000-11-28 2001-05-30 $7700.00 Window Closed / Lapsed

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