Patent DE706145C successfully refreshed from Google Patents.
US4338232A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Radiation-curable resins
Assignee: Dow Chemical Co
•
Filing: 1980-04-07
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Granted: 1982-07-06
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Expires: 2000-04-07
Abstract
Abstract Novel sulfonium-stabilized, radiation-curable, water-compatible, water-in-oil emulsions and a method of preparation are described. As an example, one such emulsion was prepared by reacting the diglycidyl ether of a polypropylene glycol with essentially a stoichiometric equivalent of acrylic acid, about 0.3 equivalent of bis(2-hydroxyethyl)-sulfide and 1.5 equivalents of H 2 O.
Inventors
- 👤 Robert F. Harris
- 👤 Dwight K. Hoffman
- 👤 Richard A. Hickner
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 08:41
CPC Classifications
C; C08; C08G; C08G59/00; C08G59/14; C08G59/1433; Y; Y10; Y10S; Y10S522/00; Y10S522/904; Y10S525/00; Y10S525/922
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
183 words
A sulfonium-stabilized, water-compatible, radiation curable, water-in-oil emulsion of a resinous composition comprising (1) molecules containing ester groups resulting from the esterification of an epoxy compound having an epoxy equivalent weight of up to 500 and an unsaturated monocarboxylic acid having a dissociation constant of at least 1×10 -7 and (2) molecules containing sufficient sulfonium groups to make said resinous composition water compatible, said molecules being the reaction product of essentially equivalent amounts of a glycidyl ether and an unsaturated acid reacted in the presence of an organic sulfide, said sulfonium groups having the structure: ##STR6## wherein R 1 and R 2 are hydrocarbyl or inertly substituted hydrocarbyl groups of from 1 to 24 carbon atoms or R 1 and R 2 together with the sulfur form a 5- or 6-membered heterocyclic ring and Z is the noncarboxylic portion of the same unsaturated monocarboxylic acid as in the ester (1) when said ester is the mono- ester of a mono-glycidyl ether and Z is the noncarboxylic portion of a saturated or unsaturated monocarboxylic acid when (1) is a polyester of a polyglycidyl glycidyl ether.
Claim 2
Dependent Claim
183 words
A sulfonium-stabilized, water-compatible, radiation curable, water-in-oil emulsion of a resinous composition comprising (1) molecules containing ester groups resulting from the esterification of an epoxy compound having an epoxy equivalent weight of up to 500 and an unsaturated monocarboxylic acid having a dissociation constant of at least 1×10 -7 and (2) molecules containing sufficient sulfonium groups to make said resinous composition water compatible, said molecules being the reaction product of essentially equivalent amounts of a glycidyl ether and an unsaturated acid reacted in the presence of an organic sulfide, said sulfonium groups having the structure: ##STR6## wherein R 1 and R 2 are hydrocarbyl or inertly substituted hydrocarbyl groups of from 1 to 24 carbon atoms or R 1 and R 2 together with the sulfur form a 5- or 6-membered heterocyclic ring and Z is the noncarboxylic portion of the same unsaturated monocarboxylic acid as in the ester (1) when said ester is the mono- ester of a mono-glycidyl ether and Z is the noncarboxylic portion of a saturated or unsaturated monocarboxylic acid when (1) is a polyester of a polyglycidyl glycidyl ether.
Claim 3
Dependent Claim
19 words
The composition defined by claim 1 wherein said unsaturated monocarboxylic acid of ester (1) is acrylic or methacrylic acid.
Claim 4
Dependent Claim
19 words
The composition defined by claim 2 wherein the sulfonium moiety of molecule (2) is a sulfonium acrylate or methacrylate.
Claim 5
Dependent Claim
30 words
The composition defined by claim 1 wherein said molecule containing ester groups is derived from an epoxy compound bearing, on the average, at least one vicinal epoxy group per molecule.
Claim 6
Dependent Claim
21 words
The composition defined by claim 4 wherein said epoxy compound bears, on the average, at least one glycidyl group per molecule.
Claim 7
Dependent Claim
131 words
The composition defined by claim 5 wherein said epoxy compound corresponds to the formula: ##STR7## wherein R 1 and R 2 are hydrogen, lower alkyl of 1 to 6 carbon atoms, chlorine or bromine and m has an average numerical value of up to about 3; or ##STR8## wherein R 1 , R 2 , R 3 and R 4 are each independently hydrogen, lower alkyl of 1 to 6 carbon atoms, chlorine or bromine and --A-- is --S--, --O--, --S--S, ##STR9## or a divalent saturated hydrocarbon of from 1 to 6 carbon atoms and n has an average numerical value of up to about 3; or ##STR10## wherein R 5 and R 6 are each independently hydrogen or lower alkyl and n has a numerical value of up to 30.
Claim 8
Dependent Claim
29 words
The composition defined by claim 6 wherein said molecule (1) bears acrylate or methacrylate moieties and wherein the sulfonium moiety of molecule (2) is a sulfonium acrylate or methacrylate.
Claim 9
Dependent Claim
73 words
The composition defined by claim 5 wherein said composition is the reaction product of (1) said glycidyl ether with (2) about one equivalent of acrylic or methacrylic acid and (3) from about 0.1 to about 0.8 equivalent of an aliphatic sulfide having a total carbon content of from 2 to about 12 carbon atoms or a 5- or 6-membered heterocyclic sulfide in which the sulfur atom is a hetero atom in the ring.
Claim 10
Dependent Claim
69 words
The composition defined by claim 8 wherein said glycidyl ether is (a) the diglycidyl ether of a polypropylene glycol having an epoxy equivalent weight of from about 94 to about 500 or (b) is the reaction product of epichlorohydrin with bisphenol A having an epoxy equivalent weight of from about 170 to about 500 and wherein said sulfide is dimethyl sulfide, diethyl sulfide, ethyl hydroxyethyl sulfide, bis(2-hydroxyethyl)sulfide or bis(2-hydroxypropyl)sulfide.
Claim 11
Dependent Claim
22 words
The composition defined by claim 8 comprising said reaction product plus a diester of a diglycidyl ether and an unsaturated monocarboxylic acid.
Claim 12
Dependent Claim
65 words
The composition defined by claim 3 wherein said sulfonium acrylate or methacrylate is C 6 H 5 -O-CH 2 CH(OH)CH 2 S.sup.⊕ (CH 2 CH 2 OH) 2 acrylate.sup.⊖ or (C 8 -C 10 )alkyl-O-CH 2 CH(OH)CH 2 S.sup.⊕ (CH 2 CH 2 OH) 2 acrylate.sup.⊖ and said molecule (1) is the diacrylate formed by reacting acrylic acid with the diglycidyl ether of bisphenol A.
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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) | 1985-07-05 | 1986-01-04 | 1986-07-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-07-05 | 1990-01-04 | 1990-07-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-07-05 | 1994-01-04 | 1994-07-06 | $7700.00 | Window Closed / Lapsed |