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US4511491A
Expired / Lapsed
US
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Stabilizers for synthetic resins
Assignee: Sumitomo Chemical Co Ltd
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Filing: 1983-07-15
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Granted: 1985-04-16
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Expires: 2003-07-15
Abstract
Abstract Phenolic compounds and methods of producing such phenolic compounds are disclosed, said compounds being of the formula: <IMAGE> (I) wherein n' is an integer from 1 to 3, and R1 is a hydrogen atom, or an alkyl group having 1 to 4 carbon atoms or an acyl group having 1 to 5 carbon atoms. These compounds are suitable as stabilizers for synthetic resins with at least one sulfur compound of the following formulas: <IMAGE> (II) wherein R2 is an alkyl group having 4 to 20 carbon atoms, and <IMAGE> wherein R3 is an alkyl group having 3 to 18 carbon atoms, and R4 and R5 each independently is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, in the ratio (I):(II) of 1:0.5-15 by weight.
Inventors
- 👤 Tamaki Ishii
- 👤 Shinichi Yachigo
- 👤 Yukoh Takahashi
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 15:30
CPC Classifications
C; C08; C08K; C08K5/00; C08K5/36; C08K5/37; C08K5/372; C08K5/04; C08K5/13; C08K5/378
Claims Analysis
Total Claims: 15
Claim 1
Independent Claim
138 words
A stabilizer for synthetic resins, of which the effective ingredient is a mixture composed of a phenolic compound (I) represented by the general formula (I): ##STR10## wherein R 1 is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms or an acyl group having 1 to 5 carbon atoms; and n is an integer from 1 to 4, and at least one sulfur-containing compound (II) selected from compounds represented by the general formulas (II-1) and (II-2): ##STR11## wherein R 2 is an alkyl group having 4 to 20 carbon atoms, and ##STR12## wherein R 3 is an alkyl group having 3 to 18 carbon atoms, and R 4 and R 5 each independently is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, in the ratio (I):(II) of 1:0.5-15 by weight.
Claim 2
Dependent Claim
138 words
A stabilizer for synthetic resins, of which the effective ingredient is a mixture composed of a phenolic compound (I) represented by the general formula (I): ##STR10## wherein R 1 is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms or an acyl group having 1 to 5 carbon atoms; and n is an integer from 1 to 4, and at least one sulfur-containing compound (II) selected from compounds represented by the general formulas (II-1) and (II-2): ##STR11## wherein R 2 is an alkyl group having 4 to 20 carbon atoms, and ##STR12## wherein R 3 is an alkyl group having 3 to 18 carbon atoms, and R 4 and R 5 each independently is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, in the ratio (I):(II) of 1:0.5-15 by weight.
Claim 3
Dependent Claim
21 words
The stabilizer for synthetic resins as claimed in claim 1 wherein the phenolic compound (I) is tetrakis[3-(3-methyl-5-t-butyl-4-hydroxyphenyl)propionyloxymethyl]methane, 2,2,2-tris[3-(3-methyl-5-t-butyl-4-hydroxyphenyl)propionyloxymethyl]ethanol, 2,2,2-tris[3-(3-methyl-5-t-butyl-4-hydroxyphenyl)propionyloxymethyl]ethylacetate, or 2,2,2-tris[3-(3-methyl-5-t-butyl-4-hydroxyphenyl)propionyloxymethyl]-1-methoxyethane.
Claim 4
Dependent Claim
17 words
The stabilizer for synthetic resins as claimed in claim 1, wherein the sulfur-containing compound (II-1) is tetrakis(3-dodecylthiopropionyloxymethyl)methane.
Claim 5
Dependent Claim
17 words
The stabilizer for synthetic resins as claimed in claim 1, wherein the sulfur-containing compound (II-2) is 3,9-bis(2-dodecylthioethyl-2,4,8,10-tetraoxaspiro[5,5]undecane.
Claim 6
Dependent Claim
19 words
The stabilizer for synthetic resins as claimed in any of claim 1 wherein the synthetic resins are polyolefin resins.
Claim 7
Dependent Claim
16 words
The stabilizer for synthetic resins as claimed in claim 5 wherein the polyolefin resin is polypropylene.
Claim 8
Dependent Claim
44 words
Phenolic compounds represented by the general formula: ##STR13## wherein n' is an integer from 1 to 3, and R 1 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms or an acyl group having 1 to 5 carbon atoms.
Claim 9
Dependent Claim
44 words
Phenolic compounds represented by the general formula: ##STR13## wherein n' is an integer from 1 to 3, and R 1 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms or an acyl group having 1 to 5 carbon atoms.
Claim 10
Dependent Claim
16 words
The compounds as claimed in claim 7 wherein the phenolic compound is 2,2,2-tris[3-(3-methyl-5-t-butyl-4-hydroxyphenyl)propionyloxymethyl]ethanol, 2,2,2-tris[3-(3-methyl-5-t-butyl-4-hydroxyphenyl)propionyloxymethyl]ethylacetate, or 2,2,2-tris[3-(3-methyl-5-t-butyl-4-hydroxyphenyl)propionyloxymethyl]-1-methoxyethane.
Claim 11
Independent Claim
99 words
A method of producing phenolic compounds represented by the general formula: ##STR14## wherein n' is an integer from 1 to 3, and R 1 is a hydrogen atom, or an alkyl group having 1 to 4 carbon atoms or an acyl group having 1 to 5 carbon atoms, characterized by reacting a 3-(3-methyl-5-t-butyl-4-hydroxyphenyl)propionic acid represented by the general formula: ##STR15## wherein R is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, with a pentaerythritol represented by the general formula: (HOCH.sub.2).sub.n' C--CH.sub.2 OR.sub.1).sub.4-n' wherein n' and R 1 have the same meaning as previously mentioned.
Claim 12
Independent Claim
99 words
A method of producing phenolic compounds represented by the general formula: ##STR14## wherein n' is an integer from 1 to 3, and R 1 is a hydrogen atom, or an alkyl group having 1 to 4 carbon atoms or an acyl group having 1 to 5 carbon atoms, characterized by reacting a 3-(3-methyl-5-t-butyl-4-hydroxyphenyl)propionic acid represented by the general formula: ##STR15## wherein R is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, with a pentaerythritol represented by the general formula: (HOCH.sub.2).sub.n' C--CH.sub.2 OR.sub.1).sub.4-n' wherein n' and R 1 have the same meaning as previously mentioned.
Claim 13
Dependent Claim
20 words
The method as claimed in claim 9 wherein the molar ratio of the pentaerythritol to the 3-(3-methyl-5-t-butyl-4-hydroxyphenyl)propionic acid is 1:0.5-4.
Claim 14
Dependent Claim
22 words
The method as claimed in claim 9 wherein the reaction is carried out in the presence of an acidic or basic catalyst.
Claim 15
Dependent Claim
21 words
The method as claimed in claim 11 wherein the basic catalyst is potassium t-butoxide, sodium methoxide, sodium phenoxide or sodium hydroxide.
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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) | 1988-04-15 | 1988-10-15 | 1989-04-16 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-04-15 | 1992-10-15 | 1993-04-16 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-04-15 | 1996-10-15 | 1997-04-16 | $7700.00 | Window Closed / Lapsed |