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1,3-Dicarbonyl compounds and polyvinyl halide resin compositions containing the same

Assignee: PHOENIX CHEMICAL Corp A CORP OF DE
•
Filing: 1981-01-14
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Granted: 1983-04-26
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Expires: 2001-01-14
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Abstract

Abstract 1,3-Dicarbonyl compounds are provided having the formula: ##STR1## wherein R 1 , R 2 and R 3 are defined in the description as well as metal and organotin enolate salts thereof. The compounds are effective in enhancing the resistance to deterioration by heat and light of polyvinyl halide resins.

Inventors

  • 👤 William E. Leistner
  • 👤 Motonobu Minagawa
  • 👤 Kouji Tsuruga
  • 👤 Masashi Harada

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-07 20:16
CPC Classifications
C; C08; C08K; C08K5/00; C08K5/04; C08K5/07; C07; C07C; C07C65/00; C07C65/32; C07C65/34; C08K5/0091; C08K5/10; C08K5/101

Claims Analysis

Total Claims: 50
Claim 1
Independent Claim 308 words
A polyvinyl halide resin composition having improved resistance to deterioration by light and/or when heated at 350° F., comprising a polyvinyl halide resin formed at least in part of the recurring group: ##STR77## and having a halogen content in excess of 40%, where X 1 is halogen and X 2 is either hydrogen or halogen, and a 1,3-dicarbonyl compound having the formula: ##STR78## wherein: R 1 is selected from the group consisting of hydrogen, alkyl groups having from one to about eighteen carbon atoms; cycloalkyl, cycloalkylalkylene, and alkylcycloalkyl groups having from five to about eighteen carbon atoms; and aryl, aralkyl and alkaryl groups having from six to about eighteen carbon atoms; and such groups substituted with one or more groups selected from the group consisting of halogen, hydroxy, and alkoxy having from one to about eighteen carbon atoms; R 2 is selected from the group consisting of alkyl groups having from one to about eighteen carbon atoms; cycloalkyl, cycloalkylalkylene, and alkylcycloalkyl groups having from five to about eighteen carbon atoms; and aryl, aralkyl and alkaryl groups having from six to about eighteen carbon atoms; and such groups substituted with one or more groups selected from the group consisting of halogen, hydroxy, alkoxy OR 1 , ester COOR 1 , alkyl and alkoxycarbonyl alkyl having one to about eighteen carbon atoms; and R 3 is selected from the group consisting of hydrogen, alkyl groups having from one to about eighteen carbon atoms; cycloalkyl, cycloalkylalkylene, and alkylcycloalkyl groups having from five to about eighteen carbon atoms; and aryl, aralkyl and alkaryl groups having from six to about eighteen carbon atoms; and such groups substituted with one or more groups selected from the group consisting of halogen, hydroxy, alkoxy OR 1 and ester COOR 1 , having from one to about eighteen carbon atoms or the corresponding metal enolate salt thereof.
Claim 2
Dependent Claim 308 words
A polyvinyl halide resin composition having improved resistance to deterioration by light and/or when heated at 350° F., comprising a polyvinyl halide resin formed at least in part of the recurring group: ##STR77## and having a halogen content in excess of 40%, where X 1 is halogen and X 2 is either hydrogen or halogen, and a 1,3-dicarbonyl compound having the formula: ##STR78## wherein: R 1 is selected from the group consisting of hydrogen, alkyl groups having from one to about eighteen carbon atoms; cycloalkyl, cycloalkylalkylene, and alkylcycloalkyl groups having from five to about eighteen carbon atoms; and aryl, aralkyl and alkaryl groups having from six to about eighteen carbon atoms; and such groups substituted with one or more groups selected from the group consisting of halogen, hydroxy, and alkoxy having from one to about eighteen carbon atoms; R 2 is selected from the group consisting of alkyl groups having from one to about eighteen carbon atoms; cycloalkyl, cycloalkylalkylene, and alkylcycloalkyl groups having from five to about eighteen carbon atoms; and aryl, aralkyl and alkaryl groups having from six to about eighteen carbon atoms; and such groups substituted with one or more groups selected from the group consisting of halogen, hydroxy, alkoxy OR 1 , ester COOR 1 , alkyl and alkoxycarbonyl alkyl having one to about eighteen carbon atoms; and R 3 is selected from the group consisting of hydrogen, alkyl groups having from one to about eighteen carbon atoms; cycloalkyl, cycloalkylalkylene, and alkylcycloalkyl groups having from five to about eighteen carbon atoms; and aryl, aralkyl and alkaryl groups having from six to about eighteen carbon atoms; and such groups substituted with one or more groups selected from the group consisting of halogen, hydroxy, alkoxy OR 1 and ester COOR 1 , having from one to about eighteen carbon atoms or the corresponding metal enolate salt thereof.
Claim 3
Dependent Claim 20 words
A polyvinyl halide resin composition in accordance with claim 1, in which the polyvinyl halide resin is polyvinyl chloride homopolymer.
Claim 4
Dependent Claim 26 words
A polyvinyl halide resin composition in accordance with claim 1, in which the polyvinyl halide resin is a copolymer of vinyl chloride and a copolymerizable monomer.
Claim 5
Dependent Claim 18 words
A polyvinyl halide resin composition in accordance with claim 3 in which the copolymerizable monomer is vinyl acetate.
Claim 6
Dependent Claim 19 words
A polyvinyl halide resin composition according to claim 1 in which the 1,3-dicarbonyl compound is a metal enolate salt.
Claim 7
Dependent Claim 17 words
A polyvinyl halide resin composition according to claim 5 in which the metal is an alkali metal.
Claim 8
Dependent Claim 18 words
A polyvinyl halide resin composition according to claim 5 in which the metal is an alkaline earth metal.
Claim 9
Dependent Claim 17 words
A polyvinyl halide resin composition according to claim 5 in which the metal is a polyvalent metal.
Claim 10
Dependent Claim 35 words
A polyvinyl halide resin composition according to claim 5 in which the metal is selected from the group consisting of lithium, sodium, potassium, magnesium, strontium, calcium, barium, cadmium, lead, zinc, tin, aluminum, antimony and zirconium.
Claim 11
Dependent Claim 18 words
A polyvinyl halide resin composition according to claim 5 in which the compound is an organotin enolate salt.
Claim 12
Dependent Claim 40 words
A polyvinyl halide resin composition according to claim 10 in which the organotin is (R) n Sn wherein n is a number from 1 to 3 and R is a hydrocarbon group having from one to about eighteen carbon atoms.
Claim 13
Dependent Claim 14 words
A polyvinyl halide resin composition according to claim 11 in which n is 1.
Claim 14
Dependent Claim 14 words
A polyvinyl halide resin composition according to claim 11 in which n is 2.
Claim 15
Dependent Claim 14 words
A polyvinyl halide resin composition according to claim 11 in which n is 3.
Claim 16
Dependent Claim 20 words
A polyvinyl halide resin composition according to claim 1 in which both R 1 of the 1,3-dicarbonyl compound are hydrogen.
Claim 17
Dependent Claim 25 words
A polyvinyl halide resin composition according to claim 1 in which one R 1 of the 1,3-dicarbonyl compound is hydrogen and the other is alkyl.
Claim 18
Dependent Claim 19 words
A polyvinyl halide resin composition according to claim 1 in which R 2 of the 1,3-dicarbonyl compound is aryl.
Claim 19
Dependent Claim 15 words
A polyvinyl halide resin composition according to claim 17 in which R 2 is phenyl.
Claim 20
Dependent Claim 19 words
A polyvinyl halide resin composition according to claim 1 in which R 2 of the 1,3-dicarbonyl compound is alkyl.
Claim 21
Dependent Claim 19 words
A polyvinyl halide resin composition according to claim 1 in which R 3 of the 1,3-dicarbonyl compound is alkyl.
Claim 22
Dependent Claim 16 words
A polyvinyl halide resin composition according to claim 1 in which the 1,3-dicarbonyl compound is 3-carbomethoxybenzoyl-benzoylmethane.
Claim 23
Dependent Claim 16 words
A polyvinyl halide resin composition according to claim 1 in which the 1,3-dicarbonyl compound is 4-carbomethoxybenzoyl-benzoylmethane.
Claim 24
Dependent Claim 16 words
A polyvinyl halide resin composition according to claim 1 in which the 1,3-dicarbonyl compound is 4-carbomethoxybenzoyl-4-t-butylbenzoylmethane.
Claim 25
Dependent Claim 16 words
A polyvinyl halide resin composition according to claim 1 in which the 1,3-dicarbonyl compound is 4-carbomethoxybenzoyl-acetylmethane.
Claim 26
Dependent Claim 16 words
A polyvinyl halide resin composition according to claim 1 in which the 1,3-dicarbonyl compound is 3-carbomethoxybenzoyl-acetylmethane.
Claim 27
Dependent Claim 282 words
A stabilizer composition capable of enhancing the resistance to deterioration by heat and/or light of polyvinyl halide resins, comprising a 1,3-dicarbonyl compound having the formula ##STR79## wherein: R 1 is selected from the group consisting of hydrogen, alkyl groups having from one to about eighteen carbon atoms; cycloalkyl, cycloalkylalkylene, and alkylcycloalkyl groups having from five to about eighteen carbon atoms; and aryl, aralkyl and alkaryl groups, having from six to about eighteen carbon atoms; and such groups substituted with one or more groups selected from the group consisting of halogen, hydroxy, and alkoxy OR 1 having from one to about eighteen carbon atoms; R 2 is selected from the group consisting of alkyl groups having from one to about eighteen carbon atoms; cycloalkyl, cycloalkylalkylene, and alkylcycloalkyl groups having from five to about eighteen carbon atoms; and aryl, aralkyl and alkaryl groups having from six to about eighteen carbon atoms; and such groups substituted with one or more groups selected from the group consisting of halogen, hydroxy, alkoxy OR 1 , ester COOR 1 , alkyl and alkoxycarbonyl alkyl having from one to about eighteen carbon atoms; and R 3 is selected from the group consisting of hydrogen, alkyl groups having from one to about eighteen carbon atoms; cycloalkyl, cycloalkylalkylene, and alkylcycloalkyl groups having from five to about eighteen carbon atoms; and aryl, aralkyl and alkaryl groups having from six to about eighteen carbon atoms; and such groups substituted with one or more groups selected from the group consisting of halogen, hydroxy, alkoxy OR 1 , and ester COOR 1 , having from one to about eighteen carbon atoms or the corresponding metal enolate salt thereof; and additional polyvinyl halide resin heat stabilizer.
Claim 28
Dependent Claim 282 words
A stabilizer composition capable of enhancing the resistance to deterioration by heat and/or light of polyvinyl halide resins, comprising a 1,3-dicarbonyl compound having the formula ##STR79## wherein: R 1 is selected from the group consisting of hydrogen, alkyl groups having from one to about eighteen carbon atoms; cycloalkyl, cycloalkylalkylene, and alkylcycloalkyl groups having from five to about eighteen carbon atoms; and aryl, aralkyl and alkaryl groups, having from six to about eighteen carbon atoms; and such groups substituted with one or more groups selected from the group consisting of halogen, hydroxy, and alkoxy OR 1 having from one to about eighteen carbon atoms; R 2 is selected from the group consisting of alkyl groups having from one to about eighteen carbon atoms; cycloalkyl, cycloalkylalkylene, and alkylcycloalkyl groups having from five to about eighteen carbon atoms; and aryl, aralkyl and alkaryl groups having from six to about eighteen carbon atoms; and such groups substituted with one or more groups selected from the group consisting of halogen, hydroxy, alkoxy OR 1 , ester COOR 1 , alkyl and alkoxycarbonyl alkyl having from one to about eighteen carbon atoms; and R 3 is selected from the group consisting of hydrogen, alkyl groups having from one to about eighteen carbon atoms; cycloalkyl, cycloalkylalkylene, and alkylcycloalkyl groups having from five to about eighteen carbon atoms; and aryl, aralkyl and alkaryl groups having from six to about eighteen carbon atoms; and such groups substituted with one or more groups selected from the group consisting of halogen, hydroxy, alkoxy OR 1 , and ester COOR 1 , having from one to about eighteen carbon atoms or the corresponding metal enolate salt thereof; and additional polyvinyl halide resin heat stabilizer.
Claim 29
Dependent Claim 36 words
A stabilizer composition according to claim 26 in which the additional heat stabilizer is selected from the group consisting of metal salts of carboxylic acids; metal salts of hydrocarbon-substituted phenols; phenolic antioxidants; 1,2-epoxides and organic phosphites.
Claim 30
Dependent Claim 17 words
A stabilizer composition according to claim 26 in which the 1,3-dicarbonyl compound is a metal enolate salt.
Claim 31
Dependent Claim 15 words
A stabilizer composition according to claim 28 in which the metal is an alkali metal.
Claim 32
Dependent Claim 16 words
A stabilizer composition according to claim 28 in which the metal is an alkaline earth metal.
Claim 33
Dependent Claim 15 words
A stabilizer composition according to claim 28 in which the metal is a polyvalent metal.
Claim 34
Dependent Claim 33 words
A stabilizer composition according to claim 28 in which the metal is selected from the group consisting of lithium, sodium, potassium, magnesium, strontium, calcium, barium, cadmium, lead, zinc, tin, aluminum, antimony and zirconium.
Claim 35
Dependent Claim 17 words
A stabilizer composition according to claim 32 in which the 1,3-dicarbonyl compound is an organotin enolate salt.
Claim 36
Dependent Claim 38 words
A stabilizer composition according to claim 33 in which the organotin is (R) n Sn wherein n is a number from 1 to 3 and R is a hydrocarbon group having from one to about eighteen carbon atoms.
Claim 37
Dependent Claim 12 words
A stabilizer composition according to claim 34 in which n is 1.
Claim 38
Dependent Claim 12 words
A stabilizer composition according to claim 34 in which n is 2.
Claim 39
Dependent Claim 12 words
A stabilizer composition according to claim 34 in which n is 3.
Claim 40
Dependent Claim 18 words
A stabilizer composition according to claim 26 in which both R 1 of the 1,3-dicarbonyl compound are hydrogen.
Claim 41
Dependent Claim 23 words
A stabilizer composition according to claim 26 in which one R 1 of the 1,3-dicarbonyl compound is hydrogen and the other is alkyl.
Claim 42
Dependent Claim 17 words
A stabilizer composition according to claim 26 in which R 2 of the 1,3-dicarbonyl compound is aryl.
Claim 43
Dependent Claim 13 words
A stabilizer composition according to claim 40 in which R 2 is phenyl.
Claim 44
Dependent Claim 17 words
A stabilizer composition according to claim 26 in which R 2 of the 1,3-dicarbonyl compound is alkyl.
Claim 45
Dependent Claim 17 words
A stabilizer composition according to claim 26 in which R 3 of the 1,3-dicarbonyl compound is alkyl.
Claim 46
Dependent Claim 14 words
A stabilizer composition according to claim 26 in which the 1,3-dicarbonyl compound is 3-carbomethoxybenzoyl-benzoylmethane.
Claim 47
Dependent Claim 14 words
A stabilizer composition according to claim 26 in which the 1,3-dicarbonyl compound is 4-carbomethoxybenzoyl-benzoylmethane.
Claim 48
Dependent Claim 14 words
A stabilizer composition according to claim 26 in which the 1,3-dicarbonyl compound is 4-carbomethoxybenzoyl-4-t-butyl-benzoylmethane.
Claim 49
Dependent Claim 14 words
A stabilizer composition according to claim 26 in which the 1,3-dicarbonyl compound is 4-carbomethoxybenzoyl-acetylmethane.
Claim 50
Dependent Claim 14 words
A stabilizer composition according to claim 26 in which the 1,3-dicarbonyl compound is 3-carbomethoxybenzoyl-acetylmethane.

References Cited (Backward Citations)

US2669548A Cited
US2669549A Cited
US3001970A Cited
US3493536A Cited
US4102839A Cited
US4123400A Cited
US4123399A Cited
US4244848A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1986-04-25 1986-10-25 1987-04-26 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1990-04-25 1990-10-25 1991-04-26 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1994-04-25 1994-10-25 1995-04-26 $7700.00 Window Closed / Lapsed

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