US 4,360,619 AGranted

Stabilizer compositions and polymers containing same

AssigneeCarstab Corporation

InventorsThomas G. Kugele, Keith A. Mesch, Karl R. Wursthorn

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Abstract

This invention relates to stabilizer compositions for polymers comprising (1) an organotin compound, or mixture of organotin compounds, (2) a mercaptan-containing organic compound or mixture of mercaptan-containing organic compounds, and, optionally, (3) a halogen-containing tin compound or mixture of halogen-containing tin compounds, said stabilizers having a total halogen content of about 0.1% to about 10% by weight based on the weight of the stabilizer composition. This invention also relates to polymer compositions containing said stabilizers, to a process for stabilizing polymer by adding thereto said stabilizers, and to articles of manufacture, e.g. pipe, comprising a polymer and said stabilizers.

Claims37

Dependent claims

A composition for stabilizing halogen containing polymers comprising:

A. about 40% to about 90% of an organotin compound or mixture of organotin compounds having one or more tetravalent tin atoms which each have at least one direct tin to carbon bond selected from compounds having the formulas:
##STR104## wherein X and X.sup.1 are the same or different and are selected from --SR.sup.2, Cl, Br, I, ##STR105## and O--R.sup.8 with the proviso that in formula (II) when t=1, in formula (V) when z=1 and in formulas (III) and (IV) at least one X or X.sup.1 is --SR.sup.2 ;
Y is --S).sub.v, --W--R.sup.3 --W.sup.1 --, ##STR106## W and W.sup.1 are the same or different and are oxygen or sulfur;
R and R.sup.1 are the same or different and are selected from alkyl, aryl, alkenyl, aralkyl, alkaryl, cycloalkyl, cycloalkenyl, ##STR107## R.sup.2 is alkyl, alkenyl, aryl, aralkyl, cycloalkyl, cycloalkenyl, ##STR108## R.sup.3 is alkylene of at least 2 carbon atoms, arylene, alkenylene of at least 2 carbon atoms, cycloalkylene, or cycloalkenylene;
R.sup.4 is alkylene, arylene, alkenylene of at least 2 carbon atoms, cycloalkylene, or cycloalkenylene;
R.sup.5 is R.sup.3 ;
R.sup.6 is nothing or R.sup.4 ;
R.sup.7 is --H or R.sup.8 ;
R.sup.8 is alkyl, alkenyl, aryl, aralkyl, alkaryl, cycloalkyl, or cycloalkenyl;
R.sup.9 is C.sub.1 to C.sub.4 alkylene;
R.sup.12 is --H or a monovalent C.sub.1 to C.sub.20 hydrocarbon radical;
R.sup.13 and R.sup.21 are the same or different and are each C.sub.1 to C.sub.20 alkyl or C.sub.1 to C.sub.20 alkoxy;
R.sup.14 is --H, aryl or C.sub.1 to C.sub.18 alkyl;
R.sup.24 is ##STR109## --OH, --SH, aryl, C.sub.1 to C.sub.18 alkyl or --H;
R.sup.16 is --H or R.sup.8 ;
i=0 or an integer from 1 to 6 inclusive;
m=1 or 2 and t=0 or 1 with the proviso that m+t=2;
n=0, 1 or 2, n'=0, 1 or 2 and p=1 or 2 with the proviso that n+n'=1 or 2 and n+n'+p=3;
a=0, 1 or 2, b=0, 1 or 2, q=an integer from 1 to 5 inclusive, c=1, 2 or 3 and d=0, 1 or 2 with the proviso that a+b=2 and c+d=3;
v=an integer from 1 to 8 inclusive;
and
w=0, 1 or 2, x=0 or 1, y=1 or 2, z=0 or 1 with the proviso that when x=0 and w=1 or 2 then y=1 and z=1, when x=1 then y=1, z=0 and w=1, when w=2 then x=0, y=1 and z=1 and when w=0 then x=0, y=1, z=1 and Y is --W--R.sup.3 --W.sup.1 --or ##STR110## B. about 10% to about 60% of a mercaptan-containing organic compound or mixture of mercaptan-containing organic compounds having the formula selected from:
##STR111## where R.sup.10 is cycloalkyl, cycloalkenyl or phenyl;
R.sup.14 is as previously defined;
R.sup.24 is as previously defined;
R.sup.15 is ##STR112## --OH, --SH, aryl, C.sub.1 to C.sub.18 alkyl, or --H;
R.sup.16 is as previously defined;
R.sup.17 is ##STR113## R.sup.18 is arylene, C.sub.1 to C.sub.8 alkylene, or ##STR114## R.sup.19 is --H or a divalent group which may contain halogen, hydroxy, mercapto or alkyl substituents and which combines with R.sup.10 when R.sup.10 is phenyl to form a naphthalene ring;
R.sup.20 is --CH.sub.3, --CH.sub.2 CH.sub.3, or ##STR115## R.sup.23 is ##STR116## --SH, aryl, C.sub.1 to C.sub.18 alkyl, --OH or --H;
with the proviso that in formula (VII) when R.sup.10 is phenyl, R.sup.23 is --OH and i=0, then the --OH and --SH groups are on non-adjacent carbon atoms;
i is as previously defined;
j=0, 1, 2 or 3;
and
f=1 or 2;
C. 0% to about 33% of a halogen-containing tin compound or mixture of halogen-containing tin compounds wherein the tin atom is tetravalent and has at least one halogen atom bonded directly to it, said halogen-containing tin compound selected from compounds having the formula:
##STR117## where Q is Cl, Br, or I;
R.sup.11 and R.sup.22 are the same or different and are selected from ##STR118## where R, R.sup.1, R.sup.8, R.sup.9, R.sup.12, R.sup.13 and R.sup.21 are as previously defined;
and
g=0, 1, 2 or 3, r=0, 1, 2, or 3 and h=1, 2, 3 or 4 with the proviso that g+r+h=4,
all percentages being by weight based on the total weight of the stabilizer composition, with the proviso that when the weight percent of the halogen-containing tin compound is 0, then at least one of the organotin compounds of component A is selected from compounds having formulas (III), (IV) or (V) wherein at least one X or X.sup.1 is Cl, Br or I.

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Dependencies are inferred from the claim text.

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Abstract

A composition for stabilizing halogen containing polymers comprising:

A. about 40% to about 90% of an organotin compound or mixture of organotin compounds having one or more tetravalent tin atoms which each have at least one direct tin to carbon bond selected from compounds having the formulas:
##STR104## wherein X and X.sup.1 are the same or different and are selected from --SR.sup.2, Cl, Br, I, ##STR105## and O--R.sup.8 with the proviso that in formula (II) when t=1, in formula (V) when z=1 and in formulas (III) and (IV) at least one X or X.sup.1 is --SR.sup.2 ;
Y is --S).sub.v, --W--R.sup.3 --W.sup.1 --, ##STR106## W and W.sup.1 are the same or different and are oxygen or sulfur;
R and R.sup.1 are the same or different and are selected from alkyl, aryl, alkenyl, aralkyl, alkaryl, cycloalkyl, cycloalkenyl, ##STR107## R.sup.2 is alkyl, alkenyl, aryl, aralkyl, cycloalkyl, cycloalkenyl, ##STR108## R.sup.3 is alkylene of at least 2 carbon atoms, arylene, alkenylene of at least 2 carbon atoms, cycloalkylene, or cycloalkenylene;
R.sup.4 is alkylene, arylene, alkenylene of at least 2 carbon atoms, cycloalkylene, or cycloalkenylene;
R.sup.5 is R.sup.3 ;
R.sup.6 is nothing or R.sup.4 ;
R.sup.7 is --H or R.sup.8 ;
R.sup.8 is alkyl, alkenyl, aryl, aralkyl, alkaryl, cycloalkyl, or cycloalkenyl;
R.sup.9 is C.sub.1 to C.sub.4 alkylene;
R.sup.12 is --H or a monovalent C.sub.1 to C.sub.20 hydrocarbon radical;
R.sup.13 and R.sup.21 are the same or different and are each C.sub.1 to C.sub.20 alkyl or C.sub.1 to C.sub.20 alkoxy;
R.sup.14 is --H, aryl or C.sub.1 to C.sub.18 alkyl;
R.sup.24 is ##STR109## --OH, --SH, aryl, C.sub.1 to C.sub.18 alkyl or --H;
R.sup.16 is --H or R.sup.8 ;
i=0 or an integer from 1 to 6 inclusive;
m=1 or 2 and t=0 or 1 with the proviso that m+t=2;
n=0, 1 or 2, n'=0, 1 or 2 and p=1 or 2 with the proviso that n+n'=1 or 2 and n+n'+p=3;
a=0, 1 or 2, b=0, 1 or 2, q=an integer from 1 to 5 inclusive, c=1, 2 or 3 and d=0, 1 or 2 with the proviso that a+b=2 and c+d=3;
v=an integer from 1 to 8 inclusive;
and
w=0, 1 or 2, x=0 or 1, y=1 or 2, z=0 or 1 with the proviso that when x=0 and w=1 or 2 then y=1 and z=1, when x=1 then y=1, z=0 and w=1, when w=2 then x=0, y=1 and z=1 and when w=0 then x=0, y=1, z=1 and Y is --W--R.sup.3 --W.sup.1 --or ##STR110## B. about 10% to about 60% of a mercaptan-containing organic compound or mixture of mercaptan-containing organic compounds having the formula selected from:
##STR111## where R.sup.10 is cycloalkyl, cycloalkenyl or phenyl;
R.sup.14 is as previously defined;
R.sup.24 is as previously defined;
R.sup.15 is ##STR112## --OH, --SH, aryl, C.sub.1 to C.sub.18 alkyl, or --H;
R.sup.16 is as previously defined;
R.sup.17 is ##STR113## R.sup.18 is arylene, C.sub.1 to C.sub.8 alkylene, or ##STR114## R.sup.19 is --H or a divalent group which may contain halogen, hydroxy, mercapto or alkyl substituents and which combines with R.sup.10 when R.sup.10 is phenyl to form a naphthalene ring;
R.sup.20 is --CH.sub.3, --CH.sub.2 CH.sub.3, or ##STR115## R.sup.23 is ##STR116## --SH, aryl, C.sub.1 to C.sub.18 alkyl, --OH or --H;
with the proviso that in formula (VII) when R.sup.10 is phenyl, R.sup.23 is --OH and i=0, then the --OH and --SH groups are on non-adjacent carbon atoms;
i is as previously defined;
j=0, 1, 2 or 3;
and
f=1 or 2;
C. 0% to about 33% of a halogen-containing tin compound or mixture of halogen-containing tin compounds wherein the tin atom is tetravalent and has at least one halogen atom bonded directly to it, said halogen-containing tin compound selected from compounds having the formula:
##STR117## where Q is Cl, Br, or I;
R.sup.11 and R.sup.22 are the same or different and are selected from ##STR118## where R, R.sup.1, R.sup.8, R.sup.9, R.sup.12, R.sup.13 and R.sup.21 are as previously defined;
and
g=0, 1, 2 or 3, r=0, 1, 2, or 3 and h=1, 2, 3 or 4 with the proviso that g+r+h=4,
all percentages being by weight based on the total weight of the stabilizer composition, with the proviso that when the weight percent of the halogen-containing tin compound is 0, then at least one of the organotin compounds of component A is selected from compounds having formulas (III), (IV) or (V) wherein at least one X or X.sup.1 is Cl, Br or I.

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