Patent US4200278A successfully refreshed from Google Patents.
US4107136A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Synthetic resin stabilizer comprising an organic phosphite and a carbonate
Assignee: Argus Chemical Corp
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Filing: 1976-10-06
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Granted: 1978-08-15
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Expires: 1996-10-06
Abstract
Abstract Stabilizer compositions are provided whose ingredients interact synergistically to improve the resistance to deterioration on heating of a variety of synthetic resin compositions. The interacting ingredients are (a) an organic phosphite having linked to phosphorus through oxygen at least two alkyl groups having from 6 to 20 carbon atoms and at least one organic group selected from polycyclic polyhydric phenol groups and pentaerythrityl groups, and (b) at least one carbonate ester of an ortho-substituted polyhydric phenol having in the molecule one to three benzenoid rings, two to three phenolic hydroxyl groups, and in each benzenoid ring one to two alkyl, cycloalkyl, or aralkyl groups of which at least one is positioned ortho to a phenolic hydroxyl group.
Inventors
- 👤 Motonobu Minagawa
- 👤 Yutaka Nakahara
- 👤 Tohru Haruna
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 21:04
CPC Classifications
C; C08; C08L; C08L23/00; C08L23/02; C08K; C08K5/00; C08K5/04; C08K5/10; C08K5/109; C08K5/14; C08K5/36; C08K5/37; C08K5/375; C08K5/49; C08K5/51; C08K5/52; C08K5/524; C08L101/00; C08L23/04; C08L23/06; C08L55/00; C08L55/02; C08L69/00; C08L77/00; C08L2207/00; C08L2207/06; C08L2207/066; C08L2312/00
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
193 words
A stabilizer composition useful in synergistically increasing the resistance of a synthetic resin to deterioration when heated at 150° C, comprising in combination (a) at least one organic phosphite having linked to phosphorus through oxygen at least two alkyl groups having from 6 to 20 carbon atoms and at least one organic group selected from polycyclic polyhydric phenol groups and pentaerythritol groups and (b) at least one carbonate ester of an orthosubstituted polyhydric phenol having an average molecular weight between 400 and 4000 and having the formula: ##STR51## in which independently at each occurrence R 1 is selected from the group consisting of alkyl, cycloalkyl, and aralkyl radicals, R 2 is selected from the group consisting of hydrogen and R 1 , A is selected from the group consisting of hydrogen and ##STR52## R is selected from the group consisting of alkyl, aryl, alkaryl, aralkyl, cycloalkyl and ##STR53## Groups, X is selected from the group consisting of --CH 2 SCH 2 --,and ##STR54## where Y is a hydrocarbon radical, B is ##STR55## L is 0 or 1, m is 1 to about 20, and n is an average of 0.1 to about 20.
Claim 2
Dependent Claim
193 words
A stabilizer composition useful in synergistically increasing the resistance of a synthetic resin to deterioration when heated at 150° C, comprising in combination (a) at least one organic phosphite having linked to phosphorus through oxygen at least two alkyl groups having from 6 to 20 carbon atoms and at least one organic group selected from polycyclic polyhydric phenol groups and pentaerythritol groups and (b) at least one carbonate ester of an orthosubstituted polyhydric phenol having an average molecular weight between 400 and 4000 and having the formula: ##STR51## in which independently at each occurrence R 1 is selected from the group consisting of alkyl, cycloalkyl, and aralkyl radicals, R 2 is selected from the group consisting of hydrogen and R 1 , A is selected from the group consisting of hydrogen and ##STR52## R is selected from the group consisting of alkyl, aryl, alkaryl, aralkyl, cycloalkyl and ##STR53## Groups, X is selected from the group consisting of --CH 2 SCH 2 --,and ##STR54## where Y is a hydrocarbon radical, B is ##STR55## L is 0 or 1, m is 1 to about 20, and n is an average of 0.1 to about 20.
Claim 3
Dependent Claim
29 words
A stabilizer composition according to claim 1 in which the weight ratio of the organic phosphite to the carbonate ester is between 5 to 1 and 1 to 2.
Claim 4
Dependent Claim
20 words
A stabilizer composition according to claim 1 in which the organic phosphite contains at least one polycyclic polyhydric phenol group.
Claim 5
Dependent Claim
31 words
A stabilizer composition according to claim 1 in which the carbonate ester is a carbonate ester of an ortho-substituted polyhydric phenol having in the molecule an odd number of benzenoid rings.
Claim 6
Dependent Claim
17 words
A stabilizer composition according to claim 1 in which the carbonate ester is an ester of 2,5-di-t-butylhydroquinone.
Claim 7
Dependent Claim
177 words
A stabilizer composition useful in synergistically increasing the resistance of a synthetic resin to deterioration when heated at 150° C, comprising in combination (a) at least one organic phosphite having linked to phosphorus through oxygen at least two alkyl groups having from 6 to 20 carbon atoms and at least one polycyclic polyhydric phenol group and (b) at least one carbonate ester of an ortho-substituted bis phenol having an average molecular weight between 400 and 4000 and having the formula: ##STR56## in which independently at each occurrence R 1 is selected from the group consisting of alkyl, cycloalkyl, and aralkyl radicals, R 2 is selected from the group consisting of hydrogen and R 1 , A is selected from the group consisting of hydrogen and ##STR57## R is selected from the group consisting of alkyl, aryl, alkaryl, aralkyl, cycloalkyl and ##STR58## groups, X is selected from the groups consisting of a direct linkage, a two-valent hydrocarbon group having one to ten carbon atoms, oxygen, --S--, and ##STR59## L is one and m is one to about 20.
Claim 8
Dependent Claim
177 words
A stabilizer composition useful in synergistically increasing the resistance of a synthetic resin to deterioration when heated at 150° C, comprising in combination (a) at least one organic phosphite having linked to phosphorus through oxygen at least two alkyl groups having from 6 to 20 carbon atoms and at least one polycyclic polyhydric phenol group and (b) at least one carbonate ester of an ortho-substituted bis phenol having an average molecular weight between 400 and 4000 and having the formula: ##STR56## in which independently at each occurrence R 1 is selected from the group consisting of alkyl, cycloalkyl, and aralkyl radicals, R 2 is selected from the group consisting of hydrogen and R 1 , A is selected from the group consisting of hydrogen and ##STR57## R is selected from the group consisting of alkyl, aryl, alkaryl, aralkyl, cycloalkyl and ##STR58## groups, X is selected from the groups consisting of a direct linkage, a two-valent hydrocarbon group having one to ten carbon atoms, oxygen, --S--, and ##STR59## L is one and m is one to about 20.
Claim 9
Dependent Claim
17 words
A stabilizer composition according to claim 1 in which the carbonate ester is an ester of trisphenol.
Claim 10
Dependent Claim
17 words
A stabilizer composition according to claim 3 in which the organic phosphite is 4,4'-isopropylidenebis(2-t-butyl-phenol) di (nonylphenyl) phosphite.
Claim 11
Dependent Claim
19 words
A stabilizer composition according to claim 3 in which the organic phosphite is tetra(C 12 -C 15 alkyl)4,4'-isopropylidenediphenol diphosphite.
Claim 12
Dependent Claim
16 words
A stabilizer composition according to claim 3 in which the organic phosphite is tetratridecyl 4,4'-n-butylidenebis(2-t-butyl-5-methylphenol) diphosphite.
Claim 13
Dependent Claim
16 words
A stabilizer composition according to claim 4 in which the organic phosphite is distearyl pentaerythritol diphosphite.
Claim 14
Dependent Claim
16 words
A stabilizer composition according to claim 3 in which the organic phosphite is hexatridecyl 1,1,3-tris(2'-methyl-4'-hydroxy-5'-t-butylphenyl)butane triphosphite.
Claim 15
Dependent Claim
155 words
A stabilizer composition according to claim 1 in which the organic phosphite has the formula (R 3 (C 6 H 4 ) a O) b P(O) 3 -bZ in which independently at each occurrence a is zero or one, b is one or two, R 3 is an alkyl group having from 6 to 20 carbon atoms, and when t is two Z is ArX 2 ArOA 2 where Ar is a carbocyclic aromatic nucleus, X 2 is selected from the group consisting of a divalent saturated hydrocarbon radical and ##STR60## where Y is saturated hydrocarbon radical, and A 2 is selected from the group consisting of hydrogen and P(O(C 6 H 4 ) a R 3 ) 2 , and; when b is one, Z is one ##STR61## group or two ArX 2 ArOA 2 groups, in at least one of which A 2 is P(O(C 6 H 4 ) a R 3 .
Claim 16
Dependent Claim
38 words
A stabilizer composition according to claim 1 containing as an additional stabilizing ingredient at least one compound selected from the group consisting of thiodipropionate esters, 1,2-epoxides, and metal salts of monocarboxylic acids having 6 to 24 carbon atoms.
Claim 17
Dependent Claim
21 words
A stabilized synthetic resin composition comprising a synthetic resin and a stabilizing amount of a stabilizer composition according to claim 1.
Claim 18
Dependent Claim
27 words
A resin composition according to claim 15 in which the quantity of stabilizer composition is from 0.002 to 10 per cent by weight of the synthetic resin.
Claim 19
Dependent Claim
31 words
A resin composition according to claim 15 in which the resin is at least one polymer selected from the group consisting of olefin polymers, acrylic polymers, vinyl halide polymers, and polyamides.
Claim 20
Dependent Claim
15 words
A resin composition according to claim 17 in which the resin is an acrylonitrile-butadiene-styrene copolymer.
Claim 21
Dependent Claim
16 words
A resin composition according to claim 17 in which the resin is an ethylene-vinyl acetate copolymer.
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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) | 1981-08-14 | 1982-02-13 | 1982-08-15 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-08-14 | 1986-02-13 | 1986-08-15 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-08-14 | 1990-02-13 | 1990-08-15 | $7700.00 | Window Closed / Lapsed |