US4020030A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Reaction products of epoxy resins, organic sulfides and protic acids
Assignee: Dow Chemical Co
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Filing: 1975-02-24
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Granted: 1977-04-26
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Expires: 1995-02-24
Abstract
Abstract Water soluble or water dispersible reaction products are produced by reacting (1) an epoxy resin having an epoxy equivalent weight of at least about 500 with (2) an organic sulfide in the presence of (3) a protic acid having a dissociation constant greater than 1 × 10 - 5 . Such reaction products can be used alone as coating compositions or can be blended with various resins which will react with pendent hydroxy groups on the above reaction product upon heating and thereby form a cross-linked product. The melamine resins are examples of suitable such "cross-linkers".
Inventors
- 👤 Robert F. Harris
- 👤 Nancy B. Tefertiller
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-27 20:01
CPC Classifications
C; C08; C08G; C08G59/00; C08G59/18; C08G59/40; C08G59/42; C08G59/4284; C08G59/4007; C08G59/4064; Y; Y10; Y10T; Y10T428/00; Y10T428/31504; Y10T428/31511; Y10T428/31529
Claims Analysis
Total Claims: 28
Claim 1
Independent Claim
52 words
A water-soluble or water-dispersible reaction product of (1) an epoxy resin bearing a plurality of vicinal epoxy groups and having an epoxy equivalent weight (EEW) of at least about 500; (2) an organic sulfide; and (3) a protic acid having a dissociation constant of at least 1 × 10 - 5 .
Claim 2
Dependent Claim
52 words
A water-soluble or water-dispersible reaction product of (1) an epoxy resin bearing a plurality of vicinal epoxy groups and having an epoxy equivalent weight (EEW) of at least about 500; (2) an organic sulfide; and (3) a protic acid having a dissociation constant of at least 1 × 10 - 5 .
Claim 3
Dependent Claim
95 words
The product defined by claim 1 wherein (1) is a resin corresponding to the formula ##STR6## wherein R 1 and R 2 are hydrogen, lower alkyl, chlorine or bromine, and m has an average numerical value of up to about 12; or ##STR7## wherein R 1 , R 2 , R 3 and R 4 are each independently hydrogen, lower alkyl, chlorine or bromine; and --A-- is --S--, --O--, --S-S--, ##STR8## or a divalent saturated hydrocarbon of from 1 to 6 carbon atoms; and n has an average numerical value of up to about 12.
Claim 4
Dependent Claim
20 words
The product defined by claim 2 wherein (1) has an epoxy equivalent weight of from about 500 to about 2,000.
Claim 5
Dependent Claim
25 words
The product defined by claim 3 wherein R 1 , R 2 , R 3 and R 4 are each hydrogen and --A-- is isopropylidene.
Claim 6
Dependent Claim
92 words
The product defined by claim 1 wherein (2) is an organic sulfide corresponding to the formula R 5 --S--R 6 , wherein R 5 and R 6 are each independently hydrocarbyl or inertly-substituted hydrocarbyl groups of from 1 to about 24 carbon atoms, or, R 5 and R 6 are joined to form a 5- or 6-membered saturated heterocyclic ring with the sulfur atom being one member of said ring and the remaining members being carbon or carbon and one non-adjacent atom of oxygen, relative to the sulfur atom in the ring.
Claim 7
Dependent Claim
26 words
The product defined by claim 5 wherein R 5 and R 6 are each alkyl or hydroxy alkyl of from 1 to about 20 carbon atoms.
Claim 8
Dependent Claim
22 words
The product defined by claim 6 wherein R 5 and R 6 are alkyl or hydroxyalkyl of from 1 to 4 carbons.
Claim 9
Dependent Claim
21 words
The product defined by claim 1 wherein (3) is an organic monocarboxylic acid of from 1 to about 24 carbon atoms.
Claim 10
Dependent Claim
20 words
The product defined by claim 8 wherein (3) is an organic monocarboxylic acid of from 1 to 4 carbon atoms.
Claim 11
Dependent Claim
11 words
The product defined by claim 9 wherein (3) is acetic acid.
Claim 12
Dependent Claim
13 words
The product defined by claim 1 wherein (3) is an organic polycarboxylic acid.
Claim 13
Dependent Claim
12 words
The product defined by claim 1 wherein (3) is an inorganic acid.
Claim 14
Dependent Claim
30 words
The product defined by claim 1 wherein there are at least about 0.7 equivalents of (2) and at least about 0.7 equivalents of (3) per vicinal epoxy group in (1).
Claim 15
Dependent Claim
51 words
The product defined by claim 4 wherein (2) is a organic sulfide corresponding to the formula R 5 --S--R 6 wherein R 5 and R 6 are alkyl or hydroxyalkyl of from 1 to 4 carbons, and wherein (3) is an organic monocarboxylic acid of from 1 to 4 carbon atoms.
Claim 16
Dependent Claim
42 words
The product defined by claim 14 wherein (2) is thiodiethanol, (3) is acetic acid, and wherein at least 0.7 equivalents of (2) and at least about 0.7 equivalents of (3) are present per vicinal epoxy group in (1) in the reaction mixture.
Claim 17
Dependent Claim
19 words
An aqueous coating composition comprising an aqueous solution or an aqueous dispersion of the product defined by claim 1.
Claim 18
Dependent Claim
25 words
An aqueous coating composition defined by claim 16 which additionally comprises a water-soluble or water-dispersible urea/formaldehyde resin, melamine/formaldehyde, imino urea/formaldehyde resin or a phenol/formaldehyde resin.
Claim 19
Dependent Claim
16 words
An aqueous coating composition comprising the product defined by claim 15 and additionally comprising hexamethoxymethylmelamine resin.
Claim 20
Dependent Claim
20 words
The aqueous coating composition defined by claim 16 which additionally comprises a polycarboxylic acid or a polycarboxylate derived from (3).
Claim 21
Dependent Claim
14 words
The aqueous coating composition defined by claim 16 which additionally comprises an acid catalyst.
Claim 22
Dependent Claim
22 words
The aqueous coating composition defined by claim 20 in which the acid catalyst is phosphoric acid, p-toluenesulfonic acid, or their ammonium salts.
Claim 23
Dependent Claim
38 words
A process for preparing the product defined by claim 1 wherein the reactants (1), (2) and (3) are reacted by contacting said reactants in an aqueous medium at a temperature of from about 35° to about 90° C.
Claim 24
Dependent Claim
18 words
The process defined by claim 22 wherein said reaction temperature is from about 60° to about 85° C.
Claim 25
Dependent Claim
27 words
The process defined by claim 22 wherein the process is conducted in the presence of a minor amount of a dispersing agent, organic cosolvent or mixtures thereof.
Claim 26
Dependent Claim
72 words
A process for preparing the product defined by claim 1 wherein the epoxy resin, (1), is reduced to a stirrable viscosity and mixed with (2) and (3) in water at a reaction temperature of from 60° to about 100° C; said water being present in the reaction mixture in amounts of from about 5 to about 50 moles of water per theoretical sulfonium moiety in the final product, based on reactants charged.
Claim 27
Dependent Claim
27 words
The process defined by claim 25 wherein said water is present in amounts of from about 10 to about 20 moles of water per theoretical sulfonium moiety.
Claim 28
Dependent Claim
18 words
The process defined by claim 26 wherein said reaction temperature is from about 70° to about 85° C.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-04-25 | 1980-10-25 | 1981-04-26 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-04-25 | 1984-10-25 | 1985-04-26 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-04-25 | 1988-10-25 | 1989-04-26 | $7700.00 | Window Closed / Lapsed |