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US4008201A Expired / Lapsed US ⏱️ 0.0 years remaining

Halogenated resins stabilized with novel compositions

Assignee: Carlisle Chemical Works Inc
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Filing: 1975-07-18
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Granted: 1977-02-15
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Expires: 1995-07-18
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Abstract

Abstract The early color stability of halogenated resins stabilized with diorganotin mercapto compounds, preferably dimethyl, is improved by including a minor amount of monohydrocarbyltin derivatives, preferably monomethyl, therewith. This combination also frequently reduces processing and finish odors associated with mercapto stabilizers and improves long term stability and/or processability.

Inventors

  • 👤 Lewis B. Weisfeld

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-29 23:42
CPC Classifications
C; C08; C08K; C08K5/00; C08K5/56; C08K5/57; C08K5/58

Claims Analysis

Total Claims: 19
Claim 1
Independent Claim 174 words
A vinyl halide resin composition comprising a resin selected from the group consisting of polyvinyl chloride, polyvinylidene chloride, copolymers of vinyl chloride with other ethylenically unsaturated monomers and copolymers of vinylidene chloride with other ethylenically unsaturated monomers and a stabilizing effective amount of a tin composition comprising in synergistic combination a diorganotin mercapto compound having a formula selected from the group consisting of ##STR13## and a monoorganotin compound having the formula R 1 Sn(Z) n (Z'Y) 3-2n wherein R 1 and R 2 are methyl or butyl, Z and Z' are each oxygen or sulfur, n is zero to 1.5 and Y is hydrogen, alkyl, cyclalkyl, ##STR14## wherein R 3 is alkylene, alkenylene, cycloalkylidene, cycloalkylene, arylene, alkarylene or aralkylene, R 4 is hydrogen, alkyl, aryl, cycloalkyl or aralkyl, R 5 is alkylene, cycloalkylidene, alkylidene, alkenylidene or cycloalkylene, said monoorganotin compound being present in amount sufficient to provide tin in amount from 50 to 98 percent by weight of the total tin content of the combination of said diorganotin mercapto compound and said monoorganotin compound.
Claim 2
Dependent Claim 174 words
A vinyl halide resin composition comprising a resin selected from the group consisting of polyvinyl chloride, polyvinylidene chloride, copolymers of vinyl chloride with other ethylenically unsaturated monomers and copolymers of vinylidene chloride with other ethylenically unsaturated monomers and a stabilizing effective amount of a tin composition comprising in synergistic combination a diorganotin mercapto compound having a formula selected from the group consisting of ##STR13## and a monoorganotin compound having the formula R 1 Sn(Z) n (Z'Y) 3-2n wherein R 1 and R 2 are methyl or butyl, Z and Z' are each oxygen or sulfur, n is zero to 1.5 and Y is hydrogen, alkyl, cyclalkyl, ##STR14## wherein R 3 is alkylene, alkenylene, cycloalkylidene, cycloalkylene, arylene, alkarylene or aralkylene, R 4 is hydrogen, alkyl, aryl, cycloalkyl or aralkyl, R 5 is alkylene, cycloalkylidene, alkylidene, alkenylidene or cycloalkylene, said monoorganotin compound being present in amount sufficient to provide tin in amount from 50 to 98 percent by weight of the total tin content of the combination of said diorganotin mercapto compound and said monoorganotin compound.
Claim 3
Dependent Claim 18 words
A vinyl halide resin composition according to claim 1 wherein said monoorgano tin compound is a monomethyltin compound.
Claim 4
Dependent Claim 87 words
A vinyl halide resin composition according to claim 2 wherein said diorganotin mercapto compound is a dimethyltin mercapto compound and said monomethyltin compound corresponds to a formula selected from the group consisting of CH 3 Sn(Z'Y) 3 and ##STR15## Y' is selected from the group consisting of R 1 , when Z' is oxygen and ##STR16## when Z' is oxygen or sulfur wherein R 4 is a monohydrocarbyl radical selected from the group consisting of alkyl, aralkyl, cycloalkyl, alkaryl and aryl having up to 20 carbon atoms.
Claim 5
Dependent Claim 121 words
A vinyl halide resin composition according to claim 3 wherein in the dimethyltin mercapto compound is selected from the group consisting of dimethyltin dioctyl mercaptide, dimethyltin bis (2-ethylhexyl mercaptide), dimethyltin didecyl mercaptide, dimethyltin dilauryl mercaptide, dimethyltin distearyl mercaptide, dimethyltin diphenyl mercaptide, dimethyltin dinaphthyl mercaptide, dimethyltin dibenzyl mercaptide, dimethyltin bis (2-phenylethyl mercaptide), dimethyltin ditolyl mercaptide, dimethyltin dicyclohexyl mercaptide, dimethyltin bis (butyl mercaptoacetate), dimethyltin bis (cyclohexyl mercaptoacetate), dimethyltin bis (octyl mercaptoacetate), dimethyltin bis (isooctyl mercaptoacetate), dimethyltin bis (2-ethylhexyl mercaptoacetate), dimethyltin bis (decyl mercaptoacetate), dimethyltin bis (lauryl mercaptoacetate), dimethyltin bis (stearyl mercaptoacetate), dimethyltin bis (butyl β-mercaptopropionate), dimethyltin bis (cyclohexyl β-mercaptopropionate), dimethyltin bis (octyl β-mercaptopropionate), dimethyltin bis (isooctyl β-mercaptopropionate), dimethyltin bis (2-ethylhexyl β-mercaptopropionate), dimethyltin bis (decyl β-mercaptopropionate), dimethyltin bis (lauryl β-mercaptopropionate), dimethyltin bis (stearyl β-mercaptopropionate).
Claim 6
Dependent Claim 221 words
A vinyl halide resin composition according to claim 4 wherein the monomethyltin compound is selected from the group consisting of methyltin tris acetate, methyltin tris butyrate, methyltin tris (2-ethylhexanoate), methyltin tris octanoate, methyltin tris laurate, methyltin tris stearate, methyltin tris hexahydrobenzoate, methyltin tris benzoate, methyltin tris (p-methyl benzoate), methyltin tris (2-phenylacetate), methyltin tris naphthoate, methyltin tris methylate, methyltin tris ethylate, methyltin tris butylate, methyltin tris (2-ethylhexylate), methyltin tris octylate, methyltin tris laurylate, methyltin tris stearylate, methyltin tris cyclohexylate, methyltin tris phenate, methyltin tris benzylate, methyltin tris naphthylate, methyltin tris (p-methylphenate), methyltin tris methylmercaptide, methyltin tris ethylmercaptide, methyltin tris butylmercaptide, methyltin tris (2-ethylhexylmercaptide), methyltin tris octylmercaptide, methyltin tris laurylmercaptide, methyltin tris stearylmercaptide, methyltin tris cyclohexylmercaptide, methyltin tris phenylmercaptide, methyltin tris benzylmercaptide, methyltin tris naphthylmercaptide, methyltin tris (monobutylsuccinate), methyltin tris (monoisooctyladipate), methyltin tris (monomethyl maleate), methyltin tris (monobutyl maleate), methyltin tris (monoisooctyl maleate), methyltin tris (monostearyl maleate), methyltin tris (monobutyl glutaconate), methyltin tris (monoisooctyl thiodipropionate), methyltin tris methyltin tris (butyl mercaptoacetate), methyltin tris (isooctyl mercaptoacetate), methyltin tris (methyl mercaptopropionate), methyltin tris (butyl mercaptopropionate), methyltin tris (octyl mercapto propionate), methyltin tris (lauryl mercaptopropionate), methyltin tris (stearyl mercaptopropionate), methyltin tris (phenyl mercaptopropionate), methyltin tris (benzyl mercaptopropionate), methyltin tris (cyclohexyl mercaptopropionate), methyltin tris (butyl mercaptobutyrate), methyltin tris (butyl-p-mercaptobenzoate), bis (methyltin dimethylate) oxide, bis (methyltin diburylate) oxide, bis (methyltin dicyclohexylate) oxide, (methyltin diphenate) oxide, and bis oxide.
Claim 7
Dependent Claim 15 words
A vinyl halide resin composition according to claim 5 wherein the resin is polyvinyl chloride.
Claim 8
Dependent Claim 41 words
A vinyl halide resin composition according to claim 5 wherein the stabilizer is present in an amount of about 0.05 to 5 weight percent and said monomethyltin compound contains 50 to 70% of the total tin metal of the tin composition.
Claim 9
Dependent Claim 28 words
A vinyl halide resin composition according to claim 7 wherein the dimethyltin mercapto compound is dimethyltin bis (isooctyl mercaptoacetate) and the monomethyltin compound is monomethyltin tris (isooctyl mercaptoacetate).
Claim 10
Dependent Claim 28 words
A vinyl halide resin composition according to claim 7 wherein the dimethyltin mercapto compound is dimethyltin bis (isooctyl mercaptoacetate) and the monomethyltin compound is monomethyltin tris (butyl mercaptopropionate).
Claim 11
Dependent Claim 27 words
A vinyl halide resin composition according to claim 7 wherein the dimethyltin mercapto compound is dimethyltin bis (isooctyl mercaptoacetate) and the monomethyltin compound is monomethyltin tris (2-ethylhexanoate).
Claim 12
Dependent Claim 24 words
A vinyl halide resin composition according to claim 5 wherein the stabilizer is present in an amount of about 0.05 to 5 weight percent.
Claim 13
Dependent Claim 45 words
A vinyl halide resin composition according to claim 1 wherein Y is hydrogen, alkyl having 1 to 12 carbon atoms when n is greater than zero, ##STR17## where R 4 is hydrogen or alkyl, ##STR18## where R 3 is alkylene, arylene, aralkylene, alkenylene or cycloalkylidene.
Claim 14
Dependent Claim 215 words
A vinyl halide resin composition comprising a resin selected from the group consisting of polyvinyl chloride, polyvinylidene chloride, copolymers of vinyl chloride with other ethylenically unsaturated monomers and copolymers of vinylidene chloride with other ethylenically unsaturated monomers and a stabilizing effective amount of a tin composition comprising in synergistic combination a diorganotin mercapto compound having a formula selected from the group consisting of ##STR19## and a monoorganotin compound having the formula [R 1 Sn(Z) n (Z'Y) 3-2n ] wherein R 1 and R 2 are methyl or butyl, Z and Z' are each oxygen or sulfur, n is zero to 1.5 with the proviso that when n = 0, m = 1; when n = 0.5, m = 2; when n = 1, m = any positive integer up to 1000; and when n = 1.5, m = 3 to 1000, and Y is hydrogen, alkyl, cyclalkyl, ##STR20## wherein R 3 is alkylene, alkenylene, cycloalkylidene, cycloalkylene, arylene, alkarylene or aralkylene, R 4 is hydrogen, alkyl, aryl, cycloalkyl or aralkyl, R 5 is alkylene, cycloalkylidene, alkylidene, alkenylidene or cycloalkylene, said monoorganotin compound being present in amount sufficient to provide tin in amount from 50 to 98 percent by weight of the total tin content of the combination of said diorganotin mercapto compound and said monoorganotin compound.
Claim 15
Dependent Claim 215 words
A vinyl halide resin composition comprising a resin selected from the group consisting of polyvinyl chloride, polyvinylidene chloride, copolymers of vinyl chloride with other ethylenically unsaturated monomers and copolymers of vinylidene chloride with other ethylenically unsaturated monomers and a stabilizing effective amount of a tin composition comprising in synergistic combination a diorganotin mercapto compound having a formula selected from the group consisting of ##STR19## and a monoorganotin compound having the formula [R 1 Sn(Z) n (Z'Y) 3-2n ] wherein R 1 and R 2 are methyl or butyl, Z and Z' are each oxygen or sulfur, n is zero to 1.5 with the proviso that when n = 0, m = 1; when n = 0.5, m = 2; when n = 1, m = any positive integer up to 1000; and when n = 1.5, m = 3 to 1000, and Y is hydrogen, alkyl, cyclalkyl, ##STR20## wherein R 3 is alkylene, alkenylene, cycloalkylidene, cycloalkylene, arylene, alkarylene or aralkylene, R 4 is hydrogen, alkyl, aryl, cycloalkyl or aralkyl, R 5 is alkylene, cycloalkylidene, alkylidene, alkenylidene or cycloalkylene, said monoorganotin compound being present in amount sufficient to provide tin in amount from 50 to 98 percent by weight of the total tin content of the combination of said diorganotin mercapto compound and said monoorganotin compound.
Claim 16
Dependent Claim 27 words
A vinyl halide resin composition according to claim 1 wherein said monoorganotin compound contains 50 to 75 percent of the total tin metal of the tin composition.
Claim 17
Dependent Claim 25 words
A vinyl halide resin composition according to claim 14 wherein the monoorganotin compound contains 50 percent of the total tin metal of the tin composition.
Claim 18
Dependent Claim 174 words
A vinyl halide resin composition comprising a resin selected from the group consisting of polyvinyl chloride, polyvinylidene chloride, copolymers of vinyl chloride with other ethylenically unsaturated monomers and copolymers of vinylidene chloride with other ethylenically unsaturated monomers and a stabilizing effective amount of a tin composition comprising in synergistic combination a diorganotin mercapto compound having a formula selected from the group consisting of ##STR21## and a monoorganotin compound having the formula R 1 Sn(Z) n (Z'Y) 3-2n wherein R 1 and R 2 are methyl or butyl, Z and Z' are each oxygen or sulfur, n is zero to 1.5 and Y is hydrogen, alkyl, cyclalkyl, ##STR22## wherein R 3 is alkylene, alkenylene, cycloalkylidene, cycloalkylene, arylene, alkarylene or aralkylene, R 4 is hydrogen, alkyl, aryl, cycloalkyl or aralkyl, R 5 is alkylene, cycloalkylidene, alkylidene, alkenylidene or cycloalkylene, said monoorganotin compound being present in amount sufficient to provide tin in amount from 25 to 98 percent by weight of the total tin content of the combination of said diorganotin mercapto compound and said monoorganotin compound.
Claim 19
Dependent Claim 174 words
A vinyl halide resin composition comprising a resin selected from the group consisting of polyvinyl chloride, polyvinylidene chloride, copolymers of vinyl chloride with other ethylenically unsaturated monomers and copolymers of vinylidene chloride with other ethylenically unsaturated monomers and a stabilizing effective amount of a tin composition comprising in synergistic combination a diorganotin mercapto compound having a formula selected from the group consisting of ##STR21## and a monoorganotin compound having the formula R 1 Sn(Z) n (Z'Y) 3-2n wherein R 1 and R 2 are methyl or butyl, Z and Z' are each oxygen or sulfur, n is zero to 1.5 and Y is hydrogen, alkyl, cyclalkyl, ##STR22## wherein R 3 is alkylene, alkenylene, cycloalkylidene, cycloalkylene, arylene, alkarylene or aralkylene, R 4 is hydrogen, alkyl, aryl, cycloalkyl or aralkyl, R 5 is alkylene, cycloalkylidene, alkylidene, alkenylidene or cycloalkylene, said monoorganotin compound being present in amount sufficient to provide tin in amount from 25 to 98 percent by weight of the total tin content of the combination of said diorganotin mercapto compound and said monoorganotin compound.

References Cited (Backward Citations)

US3640950A Cited
US3640950B1 Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1980-02-15 1980-08-16 1981-02-15 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1984-02-15 1984-08-16 1985-02-15 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1988-02-15 1988-08-16 1989-02-15 $7700.00 Window Closed / Lapsed

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