US4448915A
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Acetylene carbamide derivatives, processes for their production, and antioxidants for organic substances which comprise such derivatives as active ingredients
Assignee: Sumitomo Chemical Co Ltd
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Filing: 1982-10-19
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Granted: 1984-05-15
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Expires: 2002-10-19
Abstract
Abstract An acetylene carbamide derivative of the general formula (I): <IMAGE> (I) wherein A represents <IMAGE> wherein R1 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, is disclosed. A process for producing the acetylene carbamide derivative of the general formula (I) is also disclosed. The acetylene carbamide derivative of the invention is useful as a stabilizer for organic substances from heat and oxidation.
Inventors
- 👤 Yutaka Terada
- 👤 Yukoh Takahashi
- 👤 Shinichi Yachigo
- 👤 Tamaki Ishii
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 07:46
CPC Classifications
C; C07; C07D; C07D487/00; C07D487/02; C07D487/04; C08; C08K; C08K5/00; C08K5/16; C08K5/34; C08K5/3442; C08K5/3445
Claims Analysis
Total Claims: 28
Claim 1
Independent Claim
32 words
An acetylene carbamide derivative of the general formula (I): ##STR13## wherein A represents ##STR14## in which R 1 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
Claim 2
Dependent Claim
32 words
An acetylene carbamide derivative of the general formula (I): ##STR13## wherein A represents ##STR14## in which R 1 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
Claim 3
Dependent Claim
24 words
The acetylene carbamide derivative according to claim 1, wherein the substituent R 1 represents a hydrogen atom, a methyl group or a t-butyl group.
Claim 4
Dependent Claim
85 words
A process for producing an acetylene carbamide derivative of the general formula (I): ##STR15## wherein A represents ##STR16## in which R 1 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, which comprises reacting acetylene carbamide and a p-hydroxybenzyl alcohol derivative of the general formula (III): ##STR17## wherein R 1 is as defined above, and R 2 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, in a solvent in the presence of a catalyst.
Claim 5
Dependent Claim
85 words
A process for producing an acetylene carbamide derivative of the general formula (I): ##STR15## wherein A represents ##STR16## in which R 1 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, which comprises reacting acetylene carbamide and a p-hydroxybenzyl alcohol derivative of the general formula (III): ##STR17## wherein R 1 is as defined above, and R 2 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, in a solvent in the presence of a catalyst.
Claim 6
Dependent Claim
80 words
A process for producing an acetylene carbamide derivative of the general formula (I): ##STR18## wherein A represents ##STR19## in which R 1 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, which comprises reacting acetylene carbamide and a dialkyldithiocarbamate derivative of the general formula (IV): ##STR20## wherein R 1 is as defined above, and R 3 represents an alkyl group having 1 to 4 carbon atoms, in a solvent in the presence of a catalyst.
Claim 7
Dependent Claim
80 words
A process for producing an acetylene carbamide derivative of the general formula (I): ##STR18## wherein A represents ##STR19## in which R 1 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, which comprises reacting acetylene carbamide and a dialkyldithiocarbamate derivative of the general formula (IV): ##STR20## wherein R 1 is as defined above, and R 3 represents an alkyl group having 1 to 4 carbon atoms, in a solvent in the presence of a catalyst.
Claim 8
Dependent Claim
68 words
A process for producing an acetylene carbamide derivative of the general formula (I): ##STR21## wherein A represents ##STR22## in which R 1 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, which comprises simultaneously reacting acetylene carbamide, formaldehyde and a phenol of the general formula (V): ##STR23## wherein R 1 is an defined above, in a solvent in the presence of a catalyst.
Claim 9
Dependent Claim
68 words
A process for producing an acetylene carbamide derivative of the general formula (I): ##STR21## wherein A represents ##STR22## in which R 1 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, which comprises simultaneously reacting acetylene carbamide, formaldehyde and a phenol of the general formula (V): ##STR23## wherein R 1 is an defined above, in a solvent in the presence of a catalyst.
Claim 10
Dependent Claim
16 words
The process according to claim 3, 4 or 5, wherein said solvent is a lower alcohol.
Claim 11
Dependent Claim
16 words
The process according to claim 3, 4 or 5, wherein said catalyst is a basic catalyst.
Claim 12
Dependent Claim
19 words
The process according to claim 7, wherein said catalyst is an alkali metal hydroxide or an alkali metal alkoxide.
Claim 13
Dependent Claim
22 words
The process according to claim 3, 4 or 5, wherein the reaction is conducted at a temperature of 20° to 200° C.
Claim 14
Dependent Claim
14 words
The process according to claim 9, wherein the reaction is conducted under reflux condition.
Claim 15
Dependent Claim
22 words
The process according to claim 3, wherein the molar ratio of acetylene carbamide to the p-hydroxybenzyl alcohol derivative is 1:3.5 to 1:6.
Claim 16
Dependent Claim
21 words
The process according to claim 4, wherein the molar ratio of acetylene carbamide to the dialkyldithiocarbamate derivative is 1:3.5 to 1:5.
Claim 17
Dependent Claim
24 words
The process according to claim 5, wherein the molar ratio of acetylene carbamide to the phenol to formaldehyde is 1:3.5 to 8:3.5 to 8.
Claim 18
Dependent Claim
54 words
A composition comprising an organic substance susceptible to deterioration by light or oxygen and an effective amount to inhibit said deterioration of an acetylene carbamide derivative of the general formula (I): ##STR24## wherein A represents ##STR25## in which R 1 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
Claim 19
Dependent Claim
54 words
A composition comprising an organic substance susceptible to deterioration by light or oxygen and an effective amount to inhibit said deterioration of an acetylene carbamide derivative of the general formula (I): ##STR24## wherein A represents ##STR25## in which R 1 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
Claim 20
Dependent Claim
14 words
The stabilized composition according to claim 14, wherein said organic substance is a polymer.
Claim 21
Dependent Claim
20 words
The stabilized composition according to claim 15, wherein said polymer is a synthetic resin, a synthetic rubber or natural rubber.
Claim 22
Dependent Claim
18 words
The stabilized composition according to claim 16, wherein said synthetic resin is a polyolefin or an acrylonitrile-butadiene-styrene copolymer.
Claim 23
Dependent Claim
12 words
The stabilized composition according to claim 17, wherein said polyolefin is polypropylene.
Claim 24
Dependent Claim
14 words
The stabilized composition according to claim 16, wherein said synthetic rubber is butadiene rubber.
Claim 25
Dependent Claim
85 words
A stabilizer for organic substances which contains in combination an acetylene carbamide derivative of the general formula (I): ##STR26## wherein A represents ##STR27## in which R 1 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and a dialkyl-3,3'-thiodipropionate of the general formula (VI): ##STR28## wherein R 4 represents an alkyl group having 12 to 20 carbon atoms or a pentaerythritol-tetrakis(β-alkylthiopropionate) of the general formula (VII): ##STR29## wherein R 5 represents an alkyl group having 4 to 20 carbon atoms.
Claim 26
Dependent Claim
85 words
A stabilizer for organic substances which contains in combination an acetylene carbamide derivative of the general formula (I): ##STR26## wherein A represents ##STR27## in which R 1 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and a dialkyl-3,3'-thiodipropionate of the general formula (VI): ##STR28## wherein R 4 represents an alkyl group having 12 to 20 carbon atoms or a pentaerythritol-tetrakis(β-alkylthiopropionate) of the general formula (VII): ##STR29## wherein R 5 represents an alkyl group having 4 to 20 carbon atoms.
Claim 27
Dependent Claim
28 words
The stabilizer for organic substances according to claim 20, wherein the proportion of the acetylene carbamide derivative to the dialkyl-3,3'-thiodipropionate or pentaerythritol-tetrakis(β-alkylthiopropionate) is 1:0.5 to 1:15 by weight.
Claim 28
Dependent Claim
32 words
The stabilizer composition of claim 15 in combination with a polymer which is susceptible to deterioration by light or oxygen, the stabilizer being present in an amount effective to inhibit said deterioration.
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) | 1987-05-15 | 1987-11-14 | 1988-05-15 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-05-15 | 1991-11-14 | 1992-05-15 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-05-15 | 1995-11-14 | 1996-05-15 | $7700.00 | Window Closed / Lapsed |