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US3890276A Expired / Lapsed US ⏱️ 0.0 years remaining

Synergistic combinations of organic stabilizers for halogenated resins

Assignee: Cincinnati Milacron Chemicals Inc
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Filing: 1973-04-24
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Granted: 1975-06-17
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Expires: 1993-04-24
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Abstract

Abstract Halogenated resin formulations are stabilized against oxidation and thermal degradation with synergistic combinations of organic divalent sulfur compounds with a mono-hydrocarbyltin compound. The organic, divalent sulfur compounds, which are useful as long term stabilizers for halogenated resins, are synergistically improved by including small amounts of mono-hydrocarbyltin compounds.

Inventors

  • 👤 Christian H Stapfer

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-08 02:27
CPC Classifications
C; C08; C08K; C08K5/00; C08K5/36; C08K5/37; C08K5/56; C08K5/57

Claims Analysis

Total Claims: 20
Claim 1
Independent Claim 77 words
A HALOGEN-CONTAINING RESIN COMPOSITION COMPRISING A RESIN SELECTED FROM THE GROUP CONSISTING OF CHLORINATED POLYETHYLENE, POLYVINYL HALIDES, POLYVINYLIDENE CHLORIDE AND COPOLYMERS OF VINYL CHLORIDE WITH COPOLYMERIZABLE ETHYLENICALLY UNSATURATED MONOMERS STABILIZED WITH FROM 0.1 TO 10 WEIGHT PERCENT OF A SYNERGISTIC COMBINATION OF (A) AN ORGANIC DIVALENT-SULFUR COMPOUND SELECTED FROM THE GROUP CONSISTING OF MERCAPTALS, MERCAPTOLS, MERCAPTANS, MERCAPTOCARBOXYLATES AND SULFIDES, SAID SULFIDES CONSISTING OF CARBON, OXYGEN, HYDROGEN AND SULFUR, AND (B) A MONO-HYDROCARBYLTIN COMPOUND CORRESPONDING TO THE FORMULA
Claim 2
Dependent Claim 77 words
A HALOGEN-CONTAINING RESIN COMPOSITION COMPRISING A RESIN SELECTED FROM THE GROUP CONSISTING OF CHLORINATED POLYETHYLENE, POLYVINYL HALIDES, POLYVINYLIDENE CHLORIDE AND COPOLYMERS OF VINYL CHLORIDE WITH COPOLYMERIZABLE ETHYLENICALLY UNSATURATED MONOMERS STABILIZED WITH FROM 0.1 TO 10 WEIGHT PERCENT OF A SYNERGISTIC COMBINATION OF (A) AN ORGANIC DIVALENT-SULFUR COMPOUND SELECTED FROM THE GROUP CONSISTING OF MERCAPTALS, MERCAPTOLS, MERCAPTANS, MERCAPTOCARBOXYLATES AND SULFIDES, SAID SULFIDES CONSISTING OF CARBON, OXYGEN, HYDROGEN AND SULFUR, AND (B) A MONO-HYDROCARBYLTIN COMPOUND CORRESPONDING TO THE FORMULA
Claim 3
Dependent Claim 19 words
The halogen-containing resin composition of claim 1 wherein the halogen-containing resin comprises at least 50 weight percent polyvinyl chloride.
Claim 4
Dependent Claim 34 words
The halogen-containing resin composition of claim 1 wherein the halogen-containing resin comprises at least 50 weight percent polyvinyl chloride and about 0.5 to 5 weight percent of the synergistic combination of (a) and (b).
Claim 5
Dependent Claim 27 words
The composition of claim 3 wherein (a) is poly (cyclohexylidene-1,1-bis (thiodiglycol mercaptopropionate)) and (b) is about 4 to 12 weight percent butyl stannoic acid based upon (a).
Claim 6
Dependent Claim 26 words
The composition of claim 3 wherein (a) is distearyl cyclohexylidene-1,1-bis (mercaptopropionate) and (b) is about 4 to 12 weight percent butyl stannoic acid based on (a).
Claim 7
Dependent Claim 26 words
The composition of claim 3 wherein (a) is dibutyl (cyclohexylidene-1,1-bis (mercaptopropionate)) and (b) is about 4 to 12 weight percent butyl stannoic acid based upon (a).
Claim 8
Dependent Claim 25 words
The composition of claim 3 wherein (a) is tetrathiobis (isooctyl acetate) and (b) is about 4 to 12 weight percent butylstannoic acid based on (a).
Claim 9
Dependent Claim 9 words
The composition of claim 3 wherein R is methyl.
Claim 10
Dependent Claim 10 words
The composition of claim 3 wherein (b) is methylstannoic acid.
Claim 11
Dependent Claim 10 words
The composition of claim 3 wherein (b) is methylthiostannoic acid.
Claim 12
Dependent Claim 170 words
A halogen-containing resin composition comprising a resin selected from the group consisting of chlorinated polyethylene, polyvinyl halides, polyvinylidene chloride and copolymers of vinyl chloride with copolymerizable ethylenically unsaturated monomers stabilized with from 0.1 to 10 weight percent of a synergistic combination of (a) a divalent-sulfur compound selected from the group consisting of dilauryl sulfide, dilauryl thiodipropionate, distearyl thiodipropionate, distearyl cyclohexylidene-1,1-bis (mercaptopropionate, dithio bis (stearyl propionate), dodecoxyethyl disulfide, benzoyl disulfide, tetrathio bis (isooctyl acetate), cyclohexanone bis-dodecyl thioketal, poly (ethylidene-bis (diethylene glycol mercaptopropionate)), poly(3,5-di-t-butyl-4-hydroxy benzylidene-bis (mercaptoethanol thiodipropionate)), poly (cyclohexylidene-1, 1-bis (thiodiglycol mercaptopropionate)), formaldehyde-bis-lauroyl thioacetal, benzaldehyde-bis-benzoylthioacetal and glyoxal-tetrakisacetyl thioacetal and (b) a monohydrocarbyl tin compound selected from the group consisting of monohydrocarbyl stannoic acIds, monohydrocarbyl thiostannoic acids, mixtures thereof, polymers of said stannoic acids, polymers of said thiostannoic acids, polymers of said mixtures, alkyl esters of said stannoic acids, alkyl esters of said thiostannoic acids and alkyl esters of said mixtures, and the amount of (b) present in said combination being about 1 to about 25 weight percent of the weight of (a).
Claim 13
Dependent Claim 170 words
A halogen-containing resin composition comprising a resin selected from the group consisting of chlorinated polyethylene, polyvinyl halides, polyvinylidene chloride and copolymers of vinyl chloride with copolymerizable ethylenically unsaturated monomers stabilized with from 0.1 to 10 weight percent of a synergistic combination of (a) a divalent-sulfur compound selected from the group consisting of dilauryl sulfide, dilauryl thiodipropionate, distearyl thiodipropionate, distearyl cyclohexylidene-1,1-bis (mercaptopropionate, dithio bis (stearyl propionate), dodecoxyethyl disulfide, benzoyl disulfide, tetrathio bis (isooctyl acetate), cyclohexanone bis-dodecyl thioketal, poly (ethylidene-bis (diethylene glycol mercaptopropionate)), poly(3,5-di-t-butyl-4-hydroxy benzylidene-bis (mercaptoethanol thiodipropionate)), poly (cyclohexylidene-1, 1-bis (thiodiglycol mercaptopropionate)), formaldehyde-bis-lauroyl thioacetal, benzaldehyde-bis-benzoylthioacetal and glyoxal-tetrakisacetyl thioacetal and (b) a monohydrocarbyl tin compound selected from the group consisting of monohydrocarbyl stannoic acIds, monohydrocarbyl thiostannoic acids, mixtures thereof, polymers of said stannoic acids, polymers of said thiostannoic acids, polymers of said mixtures, alkyl esters of said stannoic acids, alkyl esters of said thiostannoic acids and alkyl esters of said mixtures, and the amount of (b) present in said combination being about 1 to about 25 weight percent of the weight of (a).
Claim 14
Dependent Claim 24 words
The halogen-containing resin composition of claim 11 wherein the halogen-containing resin is polyvinyl chloride and the monohydrocarbyl tin compound is a monomethyl tin compound.
Claim 15
Dependent Claim 23 words
The halogen-containing resin composition of claim 11 wherein the halogen-containing resin is polyvinyl chloride and the monohydrocarbyl tin compound is methyl stannoic acid.
Claim 16
Dependent Claim 47 words
The halogen-containing resin composition of claim 11 wherein the halogen-containing resin is polyvinyl chloride and the monohydrocarbyl tin compound is selected from the group consisting of methyl stannoic acid, methyl thiostannoic acid, butyltin sulfide, butyltin oxide, n-octyl stannoic acid, isoctyl thiostannoic acid and the phenyl stannoic acid.
Claim 17
Dependent Claim 140 words
A halogen-containing resin composition comprising a resin selected from the group consisting of chlorinated polyethylene, polyvinyl halides, polyvinylidene chloride and copolymers of vinyl chloride with copolymerizable ethylenically unsaturated monomers stabilized with from 0.1 to 10 weight percent of a synergistic combination of (a) a divalent-sulfur compound selected from the group consisting of dilauryl sulfide, dilauryl thiodipropionate, distearyl thiodipropionate, dithio bis (stearyl propionate), benzoyl disulfide, tetrathio bis (isooctyl acetate), cyclohexanone bis-dodecyl thioketal, poly (ethylidene-bis (diethylene glycol mercaptopropionate)), poly (3,5-di-t- butyl-4-hydroxy benzylidene-bis- (mercaptoethanol thiodipropionate)), formaldehyde-bis-lauroyl thioacetal, benzaldehyde-bis-benzoylthioacetal and glyoxal-tetrakisacetyl thioacetal and (b) a monohydrocarbyl tin compound corresponding to the formula RSn(Z)n(Z''Y)3 2n wherein R is a hydrocarbyl group containing 1 to 12 carbon atoms, Z and Z'' are independently selected from the group consisting of oxygen and sulfur, Y is selected from the group consisting of -(CH2)xCOO alkyl, when n is O;
Claim 18
Dependent Claim 140 words
A halogen-containing resin composition comprising a resin selected from the group consisting of chlorinated polyethylene, polyvinyl halides, polyvinylidene chloride and copolymers of vinyl chloride with copolymerizable ethylenically unsaturated monomers stabilized with from 0.1 to 10 weight percent of a synergistic combination of (a) a divalent-sulfur compound selected from the group consisting of dilauryl sulfide, dilauryl thiodipropionate, distearyl thiodipropionate, dithio bis (stearyl propionate), benzoyl disulfide, tetrathio bis (isooctyl acetate), cyclohexanone bis-dodecyl thioketal, poly (ethylidene-bis (diethylene glycol mercaptopropionate)), poly (3,5-di-t- butyl-4-hydroxy benzylidene-bis- (mercaptoethanol thiodipropionate)), formaldehyde-bis-lauroyl thioacetal, benzaldehyde-bis-benzoylthioacetal and glyoxal-tetrakisacetyl thioacetal and (b) a monohydrocarbyl tin compound corresponding to the formula RSn(Z)n(Z''Y)3 2n wherein R is a hydrocarbyl group containing 1 to 12 carbon atoms, Z and Z'' are independently selected from the group consisting of oxygen and sulfur, Y is selected from the group consisting of -(CH2)xCOO alkyl, when n is O;
Claim 19
Dependent Claim 22 words
The halogen-containing resin composition of claim 15 wherein the halogen-containing resin is polyvinyl chloride and the monohydrocarbyl tin compound is methylthiostannoic acid.
Claim 20
Dependent Claim 40 words
The halogen-containing resin composition of claim 15 wherein the halogen-containing resin is polyvinyl chloride and the monohydrocarbyl tin compound is selected from the group consisting of di(butylsannoxy) maleate, di(butylstannoxy) malonate, poly(butyl stannoxy benzylidene-bis (mercaptopropionate)) and poly (butyl stannoxy cyclohexylidene-bis (thiopropionate)).

References Cited (Backward Citations)

US2789963A Cited
US3021302A Cited
US3412139A Cited
US3413264A Cited
US3461091A Cited
US3630993A Cited
US3822233A Cited
US3725338A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1978-06-16 1978-12-16 1979-06-17 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1982-06-16 1982-12-16 1983-06-17 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1986-06-16 1986-12-16 1987-06-17 $7700.00 Window Closed / Lapsed

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