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US4560709A Expired / Lapsed US ⏱️ 0.0 years remaining

Photopolymerizable mixtures and processes for the photopolymerization of cationically polymerizable compounds

Assignee: Novartis Corp
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Filing: 1983-08-26
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Granted: 1985-12-24
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Expires: 2003-08-26
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Abstract

Abstract Cationically polymerizable compounds, for example epoxide compounds, can be polymerized photochemically using a catalyst combination consisting of an aromatic iodonium salt and a ketone of the formula I, II or III ##STR1## in which n is 1 or 2 and Ar, X, X', R 1 , R 2 and R 3 are as defined in claim 1. In this combination, the ketones act as a co-catalyst and drastically accelerate the photopolymerization, although they are not able to initiate a cationic photopolymerization on their own.

Inventors

  • 👤 Godwin Berner
  • 👤 Rudolf Kirchmayr

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-29 06:08
CPC Classifications
C; C08; C08F; C08F2/00; C08F2/46; C08F2/48; C08F2/50; C08G; C08G59/00; C08G59/18; C08G59/68

Claims Analysis

Total Claims: 11
Claim 1
Independent Claim 165 words
A photopolymerizable mixture consisting essentially of (a) an epoxide compound or a mixture of epoxide compounds, said epoxide compound containing no ethylenically unsaturated group, (b) an aromatic iodonium salt as the polymerization catalyst, and (c) an aromatic carbonyl compound as the cocatalyst which is a ketone of formula I ##STR5## in which n is a 1 or 2 and Ar, if n is 1, is phenyl, diphenyl, tetrahydronaphthyl or phenyl which is substituted by one or more of the radicals F, Cl, Br, C 1 -C 12 -alkyl, --O--phenyl or --OAlk and, if n is 2, is C 6 -C 12 -arylene or a -phenylene-T-phenylene group in which T is --O--, --S-- or --CH 2 --, and Alk is C 1 -C 4 -alkyl, X is OH, R 1 is C 1 -C 8 -alkyl or --CH 2 CH 2 COOAlk and R 2 is C 1 -C 8 -alkyl or allyl, or R 1 and R 2 together are C 4 -C 7 -alkylene.
Claim 2
Dependent Claim 165 words
A photopolymerizable mixture consisting essentially of (a) an epoxide compound or a mixture of epoxide compounds, said epoxide compound containing no ethylenically unsaturated group, (b) an aromatic iodonium salt as the polymerization catalyst, and (c) an aromatic carbonyl compound as the cocatalyst which is a ketone of formula I ##STR5## in which n is a 1 or 2 and Ar, if n is 1, is phenyl, diphenyl, tetrahydronaphthyl or phenyl which is substituted by one or more of the radicals F, Cl, Br, C 1 -C 12 -alkyl, --O--phenyl or --OAlk and, if n is 2, is C 6 -C 12 -arylene or a -phenylene-T-phenylene group in which T is --O--, --S-- or --CH 2 --, and Alk is C 1 -C 4 -alkyl, X is OH, R 1 is C 1 -C 8 -alkyl or --CH 2 CH 2 COOAlk and R 2 is C 1 -C 8 -alkyl or allyl, or R 1 and R 2 together are C 4 -C 7 -alkylene.
Claim 3
Dependent Claim 24 words
A photopolymerisable mixture according to claim 1, wherein component (a) is a mixture of a polyglycidylether type epoxide resin with an epoxidised soybean oil.
Claim 4
Dependent Claim 151 words
A photopolymerisable mixture according to claim 1, wherein component (b) is an aromatic iodonium salt of the formula IV [Ar.sup.1 --I--Ar.sup.2 ].sup.+ [MQ.sub.n ].sup.- IV in which Ar 1 and Ar 2 independently of one another are phenyl, naphthyl or phenyl which is substituted by one or more of the radicals C 1 -C 8 -alkyl, phenyl, phenoxy, halogen, nitro or C 1 -C 4 -alkoxy, or Ar 1 and Ar 2 together are a divalent radical of the formula V ##STR6## in which Y is a direct bond, --O--, --CH 2 -- or --CO-- and R is C 1 -C 4 -alkyl, halogen, nitro or C 1 -C 4 -alkoxy, M is a metal atom or metalloid atom from the series comprising B, P, As, Sb, Sn, Bi and Fe, Q is fluorine or chlorine and n is 4, 5 or 6 and 1 larger than the valency of M.
Claim 5
Dependent Claim 14 words
A photopolymerisable mixture according to claim 2, wherein component (b) is a diphenyliodonium salt.
Claim 6
Dependent Claim 39 words
A photopolymerisable mixture according to claim 2, wherein the anion [MQ n ] - of the iodonium salt is one of the anions BF 4 - , PF 6 - , AsF 6 - or SbF 6 - .
Claim 7
Dependent Claim 49 words
A photopolymerisable mixture according to claim 1, wherein component (c) is a compound of the formula I, in which n is 1, Ar is phenyl, chlorophenyl or C 7 -C 10 -alkylphenyl, R 1 and R 2 are either both methyl or together are pentamethylene and X is --OH.
Claim 8
Dependent Claim 13 words
A photopolymerisable mixture according to claim 1, wherein the mixture contains a photosensitiser.
Claim 9
Dependent Claim 184 words
A process for the photochemical polymerization of cationically polymerizable compounds or mixtures of compounds which comprises exposing a mixture of (a) an epoxide compound or a mixture of epoxide compounds, said epoxide compound containing no ethylenically unsaturated group, (b) an aromatic iodonium salt as the polymerization catalyst, and (c) an aromatic carbonyl compound as the cocatalyst which is a ketone of formula I ##STR7## in which n is a 1 or 2 and Ar, if n is 1, is phenyl, diphenyl, tetrahydronaphthyl or phenyl which is substituted by one or more of the radicals F, Cl, Br, C 1 -C 12 -alkyl, --O--phenyl or --OAlk and, if n is 2, is C 6 -C 12 -arylene or a -phenylene-T-phenylene group in which T is --O--, --S-- or --CH 2 --, and Alk is C 1 -C 4 -alkyl, X is OH, R 1 is C 1 -C 8 -alkyl or --CH 2 CH 2 COOAlk and R 2 is C 1 -C 8 -alkyl or allyl, or R 1 and R 2 together are C 4 -C 7 -alkylene, to irradiation by short-wave light.
Claim 10
Dependent Claim 184 words
A process for the photochemical polymerization of cationically polymerizable compounds or mixtures of compounds which comprises exposing a mixture of (a) an epoxide compound or a mixture of epoxide compounds, said epoxide compound containing no ethylenically unsaturated group, (b) an aromatic iodonium salt as the polymerization catalyst, and (c) an aromatic carbonyl compound as the cocatalyst which is a ketone of formula I ##STR7## in which n is a 1 or 2 and Ar, if n is 1, is phenyl, diphenyl, tetrahydronaphthyl or phenyl which is substituted by one or more of the radicals F, Cl, Br, C 1 -C 12 -alkyl, --O--phenyl or --OAlk and, if n is 2, is C 6 -C 12 -arylene or a -phenylene-T-phenylene group in which T is --O--, --S-- or --CH 2 --, and Alk is C 1 -C 4 -alkyl, X is OH, R 1 is C 1 -C 8 -alkyl or --CH 2 CH 2 COOAlk and R 2 is C 1 -C 8 -alkyl or allyl, or R 1 and R 2 together are C 4 -C 7 -alkylene, to irradiation by short-wave light.
Claim 11
Dependent Claim 152 words
A process according to claim 8, wherein an aromatic iodonium salt of the formula IV [Ar.sup.1 --I--Ar.sup.2 ].sup.+ [MQ.sub.n ].sup.- IV in which Ar 1 and Ar 2 independently of one another are phenyl, naphthyl or phenyl which is substituted by one or more of the radicals C 1 -C 8 -alkyl, phenyl, phenoxy, halogen, nitro or C 1 -C 4 -alkoxy, or Ar 1 and Ar 2 together are a divalent radical of the formula V ##STR8## in which Y is a direct bond, --O--, --CH 2 -- or --CO-- and R is C 1 -C 4 -alkyl, halogen, nitro or C 1 -C 4 -alkoxy, M is a metal atom or metalloid atom from the series comprising B, P, As, Sb, Sn, Bi and Fe, Q is fluorine or chlorine and n is 4, 5 or 6 and 1 larger than the valency of M, is used as component (b).

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1988-12-23 1989-06-24 1989-12-24 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1992-12-23 1993-06-24 1993-12-24 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1996-12-23 1997-06-24 1997-12-24 $7700.00 Window Closed / Lapsed

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