US4129609A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Method for improving storage stability of epoxy ester thermosetting resins with thiuram compounds
Assignee: Nippon Shokubai Co Ltd
•
Filing: 1977-07-11
•
Granted: 1978-12-12
•
Expires: 1997-07-11
Abstract
Abstract A method for improving storage stability of a thermosetting resin, which comprises adding a thiuram compoound to the thermosetting resin comprising a reaction product of an epoxy resin with an α,β-unsaturated monocarboxylic acid dissolved in a polymerizable olefinic unsaturated compound, said thiuram compound having in one molecule thereof at least one atomic group expressed by the following general formula I: ##STR1## wherein p is an integer of 1 to 4, and being used in an amount of 0.0001 to 2.0 parts by weight per 100 parts by weight of said reaction product.
Inventors
- 👤 Toshio Awaji
- 👤 Daisuke Atobe
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 05:36
CPC Classifications
C; C08; C08K; C08K5/00; C08K5/36; C08K5/39; C08K5/40; Y; Y10; Y10S; Y10S525/00; Y10S525/922
Claims Analysis
Total Claims: 49
Claim 1
Independent Claim
177 words
A method for improving storage stability of a thermosetting resin, which comprises a adding thiuram compound to the thermosetting resin comprising a reaction product of a 1,2- epoxy resin with an α, β-unsaturated monocarboxylic acid dissolved in a polymerizable olefinic unsaturated compound, said thiurum compound having the formula selected from the group having the formula: ##STR7## wherein p is an integer of 1 through 4, R 1 , R 2 and R 3 are alkyl of 1 to 4 carbon atoms or phenyl, and R 4 is alkyl of 1 to 4 carbon atoms, phenyl or ##STR8## wherein q is an integer of 1 to 4, R 5 , R 6 and R 7 are alkyl of 1 to 4 carbon atoms or phenyl, provided that where R 1 and R 2 are joined, and R 3 and R 4 are joined, said joined groups are selected from the group consisting of pentamethylene and diethyleneoxy and being used in an amount of 0.0001 to 2.0 parts by weight per 100 parts by weight of said reaction product.
Claim 2
Independent Claim
177 words
A method for improving storage stability of a thermosetting resin, which comprises a adding thiuram compound to the thermosetting resin comprising a reaction product of a 1,2- epoxy resin with an α, β-unsaturated monocarboxylic acid dissolved in a polymerizable olefinic unsaturated compound, said thiurum compound having the formula selected from the group having the formula: ##STR7## wherein p is an integer of 1 through 4, R 1 , R 2 and R 3 are alkyl of 1 to 4 carbon atoms or phenyl, and R 4 is alkyl of 1 to 4 carbon atoms, phenyl or ##STR8## wherein q is an integer of 1 to 4, R 5 , R 6 and R 7 are alkyl of 1 to 4 carbon atoms or phenyl, provided that where R 1 and R 2 are joined, and R 3 and R 4 are joined, said joined groups are selected from the group consisting of pentamethylene and diethyleneoxy and being used in an amount of 0.0001 to 2.0 parts by weight per 100 parts by weight of said reaction product.
Claim 3
Dependent Claim
145 words
A method according to claim 1, wherein said epoxy resin is at least one member from the group consisting of a bisphenol-base epoxy resin expressed by the following general formula II: ##STR9## wherein R 1 represents H or CH 3 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 independently represent a member selected from the group consisting of H, Cl, Br and F, A represents a member selected from the group consisting of an alkylene group containing 1 to 8 carbon atoms, S, O and ##STR10## and n is zero or an integer of 1 to 10, and a novolac-base epoxy resin expressed by the following general formula III: ##STR11## wherein R 10 represents H or CH 3 and m is zero or an integer of 1 to 12.
Claim 4
Dependent Claim
20 words
A method according to claim 2, wherein said epoxy resin is the bisphenol-base epoxy resin of the general formula II.
Claim 5
Dependent Claim
20 words
A method according to claim 2, wherein said epoxy resin is the novolac-base epoxy resin of the general formula III.
Claim 6
Dependent Claim
65 words
A method according to claim 3, wherein said epoxy resin is a mixture of a bisphenol-base epoxy resin (X) of the general formula II having an epoxy equivalent of 170 to 225 and a bisphenol-base epoxy resin (Y) of the general formula II having an epoxy equivalent of 400 to 600 in a molar ratio of 0.2≦X<0.4: 0.6<Y≦0.8 (in which X + Y = 1.0).
Claim 7
Dependent Claim
24 words
A method according to claim 1, wherein said unsaturated compound is at least one member selected from the group consisting of styrene and diallylphthalate.
Claim 8
Dependent Claim
12 words
A method according to claim 6, wherein said unsaturated compound is styrene.
Claim 9
Dependent Claim
12 words
A method according to claim 6, wherein said unsaturated compound is diallylphthalate.
Claim 10
Dependent Claim
19 words
A method according to claim 1, wherein p in the formula I is an integer of 1 to 2.
Claim 11
Dependent Claim
14 words
A method according to claim 9, wherein p in the formula I is 1.
Claim 12
Dependent Claim
14 words
A method according to claim 9, wherein p in the formula I is 2.
Claim 13
Dependent Claim
31 words
A method according to claim 1, wherein said thiuram compound is used in an amount of 0.001 to 0.5 parts by weight per 100 parts by weight of said reaction product.
Claim 14
Dependent Claim
19 words
A method according to claim 5, wherein p in the formula I is an integer of 1 to 2.
Claim 15
Dependent Claim
13 words
A method according to claim 10, wherein said thiuram monosulfide is tetramethylthiuram monosulfide.
Claim 16
Dependent Claim
13 words
A method according to claim 10, wherein said thiuram monosulfide is tetraethylthiuram monosulfide.
Claim 17
Dependent Claim
13 words
A method according to claim 10, wherein said thiuram monosulfide is tetrapropylthiuram monosulfide.
Claim 18
Dependent Claim
13 words
A method according to claim 10, wherein said thiuram monosulfide is tetrabutylthiuram monosulfide.
Claim 19
Dependent Claim
13 words
A method according to claim 10, wherein said thiuram monosulfide is bis(trimethylthiuram monosulfide)ethylene.
Claim 20
Dependent Claim
13 words
A method according to claim 11, wherein said thiuram disulfide is tetramethylthiuram disulfide.
Claim 21
Dependent Claim
13 words
A method according to claim 11, wherein said thiuram disulfide is tetraethylthiuram disulfide.
Claim 22
Dependent Claim
13 words
A method according to claim 11, wherein said thiuram disulfide is tetrabutylthiuram disulfide.
Claim 23
Dependent Claim
13 words
A method according to claim 11, wherein said thiuram disulfide is dipentamethylenethiuram disulfide.
Claim 24
Dependent Claim
13 words
A method according to claim 11, wherein said thiuram disulfide is bis(trimethylthiuram disulfide)ethylene.
Claim 25
Dependent Claim
180 words
A thermosetting resin composition with improved storage stability comprising a reaction product of a 1,2- epoxy resin with an α, β-unsaturated monocarboxylic acid dissolved into a polymerizable olefinic unsaturated compound, said unsaturated compound being contained in an amount of 10 to 70% by weight of said resin, and a thiuram compound having the formula selected from the group having the formula: ##STR12## wherein p is an integer of 1 through 4, R 1 , R 2 and R 3 are alkyl of 1 to 4 carbon atoms or phenyl, and R 4 is alkyl of 1 to 4 carbon atoms, phenyl or ##STR13## wherein q is an integer of 1 to 4, R 5 , R 6 and R 7 are alkyl of 1 to 4 carbon atoms or phenyl, provided that where R 1 and R 2 are joined, and R 3 and R 4 are joined, said joined groups are selected from the group consisting of pentamethylene and diethyleneoxy said thiuram compound being used in an amount of 0.0001 to 2.0 parts by weight of said reaction product.
Claim 26
Dependent Claim
180 words
A thermosetting resin composition with improved storage stability comprising a reaction product of a 1,2- epoxy resin with an α, β-unsaturated monocarboxylic acid dissolved into a polymerizable olefinic unsaturated compound, said unsaturated compound being contained in an amount of 10 to 70% by weight of said resin, and a thiuram compound having the formula selected from the group having the formula: ##STR12## wherein p is an integer of 1 through 4, R 1 , R 2 and R 3 are alkyl of 1 to 4 carbon atoms or phenyl, and R 4 is alkyl of 1 to 4 carbon atoms, phenyl or ##STR13## wherein q is an integer of 1 to 4, R 5 , R 6 and R 7 are alkyl of 1 to 4 carbon atoms or phenyl, provided that where R 1 and R 2 are joined, and R 3 and R 4 are joined, said joined groups are selected from the group consisting of pentamethylene and diethyleneoxy said thiuram compound being used in an amount of 0.0001 to 2.0 parts by weight of said reaction product.
Claim 27
Dependent Claim
146 words
A composition according to claim 24, wherein said epoxy resin is at least one member selected from the group consisting of a bisphenol-base epoxy resin expressed by the following general formula II: ##STR14## wherein R 1 represents H or CH 3 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 independently represent a member selected from the group consisting of H, Cl, Br and F, A represents a member selected from the group consisting of an alkylene group containing 1 to 8 carbon atoms, S, O and ##STR15## and n is zero or an integer of 1 to 10, and a novolac-base epoxy resin expressed by the following general formula III: ##STR16## wherein R 10 represents H or CH 3 and m is zero or an integer of 1 to 12.
Claim 28
Dependent Claim
20 words
A composition according to claim 25 wherein said epoxy resin is the bisphenol-base epoxy resin of the general formula II.
Claim 29
Dependent Claim
19 words
A composition according to claim 25, wherein said epoxy resin is the novolac-base epoxy resin of the formula III.
Claim 30
Dependent Claim
65 words
A composition according to claim 26, wherein said epoxy resin is a mixture of a bisphenol-base epoxy resin (X) of the general formula II having an epoxy equivalent of 170 to 225 and a bisphenol-base epoxy resin (Y) of the general formula II having an epoxy equivalent of 400 to 600 in a molar ratio of 0.2≦X<0.4: 0.6<Y≦0.8 (in which X + Y = 1.0).
Claim 31
Dependent Claim
24 words
A composition according to claim 24, wherein said unsaturated compound is at least one member selected from the group consisting of styrene and diallylphthalate.
Claim 32
Dependent Claim
12 words
A composition according to claim 29, wherein said unsaturated compound is styrene.
Claim 33
Dependent Claim
12 words
A composition according to claim 29, wherein said unsaturated monomer is diallylphthalate.
Claim 34
Dependent Claim
19 words
A composition according to claim 24, wherein p in the formula I is an integer of 1 to 2.
Claim 35
Dependent Claim
14 words
A composition according to claim 32, wherein p in the formula I is 1.
Claim 36
Dependent Claim
14 words
A composition according to claim 32, wherein p in the formula I is 2.
Claim 37
Dependent Claim
31 words
A composition according to claim 24, wherein said thiuram compound is used in an amount of 0.001 to 0.5 parts by weight per 100 parts by weight of said reaction product.
Claim 38
Dependent Claim
25 words
A composition according to claim 24, wherein said unsaturated compound is used in an amount of 20 to 60% by weight based on said resin.
Claim 39
Dependent Claim
20 words
A composition according to claim 28, wherein p in the general formula I is an integer of 1 to 2.
Claim 40
Dependent Claim
13 words
A composition according to claim 33, wherein said thiuram monosulfide is tetramethylthiuram monosulfide.
Claim 41
Dependent Claim
13 words
A composition according to claim 33, wherein said thiuram monosulfide is tetraethylthiuram monosulfide.
Claim 42
Dependent Claim
13 words
A composition according to claim 33, wherein said thiuram monosulfide is tetrapropylthiuram monosulfide.
Claim 43
Dependent Claim
13 words
A composition according to claim 33, wherein said thiuram monosulfide is tetrabutylthiuram monosulfide.
Claim 44
Dependent Claim
13 words
A composition according to claim 33, wherein said thiuram monosulfide is bis(trimethylthiuram monosulfide)ethylene.
Claim 45
Dependent Claim
13 words
A composition according to claim 34, wherein said thiuram disulfide is tetramethylthiuram disulfide.
Claim 46
Dependent Claim
13 words
A composition according to claim 34, wherein said thiuram disulfide is tetraethylthiuram disulfide.
Claim 47
Dependent Claim
13 words
A composition according to claim 34, wherein said thiuram disulfide is tetrabutylthiuram disulfide.
Claim 48
Dependent Claim
13 words
A composition according to claim 34, wherein said thiuram disulfide is dipentamethylenethiuram disulfide.
Claim 49
Dependent Claim
13 words
A composition according to claim 34, wherein said thiuram disulfide is bis(trimethylthiuram disulfide)ethylene.
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) | 1981-12-11 | 1982-06-12 | 1982-12-12 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-12-11 | 1986-06-12 | 1986-12-12 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-12-11 | 1990-06-12 | 1990-12-12 | $7700.00 | Window Closed / Lapsed |