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US4324679A Expired / Lapsed US ⏱️ 0.0 years remaining

Controlling odor in photopolymerization

Assignee: 3M Co
•
Filing: 1980-02-21
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Granted: 1982-04-13
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Expires: 2000-02-21
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Abstract

Abstract The use of certain organic materials having non-aromatic carbon-carbon unsaturation is described in connection with photopolymerizable compositions containing aromatic sulfonium complex salt photoinitiators in order to minimize or eliminate the odor of organosulfur reaction by-products.

Inventors

  • 👤 Robert C. Carlson

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-02 23:00
CPC Classifications
G; G03; G03F; G03F7/00; G03F7/004; G03F7/038; C; C08; C08G; C08G59/00; C08G59/18; C08G59/68; C08G59/687

Claims Analysis

Total Claims: 7
Claim 1
Independent Claim 269 words
A liquid composition consisting essentially of: (a) aromatic sulfonium complex salt, said salt being photodecomposable and being capable of initiating polymerization of cationically polymerizable monomers upon exposure to actinic radiation; (b) at least about 15% by weight of liquid neutral oxyethylene-containing material selected from: (i) compounds having the formula R[(OC.sub.2 H.sub.4).sub.n (OC.sub.3 H.sub.6).sub.m OH].sub.p where R is a polyvalent neutral organic radical having a valence of p, n+m is in the range of 1 to about 25, p is in the range of 2 to 6, wherein the oxyethylene units in such compounds constitute at least about 15% by weight of such compounds; and wherein the number of carbon atoms in R divided by the product of n and p is less than three; and (ii) compounds having the formula: R.sup.1 (OC.sub.2 H.sub.4).sub.n (OC.sub.3 H.sub.6).sub.m OH where R 1 is monovalent neutral organic radical, where n+m is in the range of 1 to 25, wherein the oxyethylene units in such compounds constitute at least about 50% by weight of such compounds; and (iii) compounds of the formula: H(OC.sub.2 H.sub.4).sub.n (OC.sub.3 H.sub.6).sub.m OH where n+m is in the range of 2 to about 25, wherein the oxyethylene units in such compounds constitute at least about 15% by weight of such compounds; and (c) an organic material containing at least one site of non-aromatic carbon-carbon unsaturation; wherein said unsaturation in said organic material is ethylenic and wherein each ethylenically unsaturated carbon atom has no more than one hydrogen atom bonded thereto; and wherein said organic material is present in an amount of about 0.5 to 20% by weight of said composition.
Claim 2
Dependent Claim 269 words
A liquid composition consisting essentially of: (a) aromatic sulfonium complex salt, said salt being photodecomposable and being capable of initiating polymerization of cationically polymerizable monomers upon exposure to actinic radiation; (b) at least about 15% by weight of liquid neutral oxyethylene-containing material selected from: (i) compounds having the formula R[(OC.sub.2 H.sub.4).sub.n (OC.sub.3 H.sub.6).sub.m OH].sub.p where R is a polyvalent neutral organic radical having a valence of p, n+m is in the range of 1 to about 25, p is in the range of 2 to 6, wherein the oxyethylene units in such compounds constitute at least about 15% by weight of such compounds; and wherein the number of carbon atoms in R divided by the product of n and p is less than three; and (ii) compounds having the formula: R.sup.1 (OC.sub.2 H.sub.4).sub.n (OC.sub.3 H.sub.6).sub.m OH where R 1 is monovalent neutral organic radical, where n+m is in the range of 1 to 25, wherein the oxyethylene units in such compounds constitute at least about 50% by weight of such compounds; and (iii) compounds of the formula: H(OC.sub.2 H.sub.4).sub.n (OC.sub.3 H.sub.6).sub.m OH where n+m is in the range of 2 to about 25, wherein the oxyethylene units in such compounds constitute at least about 15% by weight of such compounds; and (c) an organic material containing at least one site of non-aromatic carbon-carbon unsaturation; wherein said unsaturation in said organic material is ethylenic and wherein each ethylenically unsaturated carbon atom has no more than one hydrogen atom bonded thereto; and wherein said organic material is present in an amount of about 0.5 to 20% by weight of said composition.
Claim 3
Dependent Claim 24 words
A liquid composition in accordance with claim 1, wherein at least one of said ethylenically unsaturated carbon atoms has bonded thereto a C=O group.
Claim 4
Dependent Claim 155 words
A liquid composition in accordance with claim 1, wherein said complex salt is of the formula [(R).sub.a (R.sup.1).sub.b (R.sup.2).sub.c S].sub.d.sup.+ [MQ.sub.e ].sup.-(e-f) where R is a monovalent aromatic organic radical, R 1 is a monovalent organic aliphatic radical selected from alkyl, cycloalkyl and substituted alkyl, R 2 is a polyvalent organic radical forming a heterocyclic or fused ring structure selected from aliphatic radicals and aromatic radicals, M is a metal or metalloid, Q is a halogen radical, a is a whole number equal to 0 to 3 inclusive, b is a whole number equal to 0 to 2 inclusive, c is a whole number equal to 0 or 1, where the sum of a+b+c is a value equal to 3, d=e-f, f is equal to the valence of M and is an integer equal to from 2 to 7 inclusive, e is greater than f and is an integer having a value up to 8.
Claim 5
Dependent Claim 25 words
A liquid composition in accordance with claim 3, wherein a is equal to 3, M is selected from P or Sb, and Q is F.
Claim 6
Dependent Claim 77 words
A liquid composition in accordance with claim 1, wherein said oxyethylene-containing material is selected from H(OC 2 H 4 ) 2 OH, H(OC 2 H 4 ) 3 OH, H(OC 2 H 4 ) 4 OH, HOC 2 H 4 OC 3 H 6 OH, HOC 2 H 4 (OC 3 H 6 ) 2 OH, H(OC 2 H 4 ) 4 (OC 3 H 6 ) 6 OH and H(OC 2 H 4 ) 22 OH.
Claim 7
Dependent Claim 76 words
A liquid composition in accordance with claim 1, wherein said oxyethylene-containing material is selected from C 3 H 5 [(OC 2 H 4 )OH] 3 , C 3 H 5 [(OC 2 H 4 ) 2 OH] 3 , C 4 H 8 [(OC 2 H 4 ) 4 OH] 2 , and C 6 H 4 [C 2 H 4 (OC 2 H 4 ) 3 (OC 3 H 6 ) 3 OH] 2 .

References Cited (Backward Citations)

US4058400A Cited
US4058401A Cited
US4069054A Cited
US4108747A Cited
US4138255A Cited
US4156035A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1985-04-12 1985-10-12 1986-04-13 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1989-04-12 1989-10-12 1990-04-13 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1993-04-12 1993-10-12 1994-04-13 $7700.00 Window Closed / Lapsed

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