Bis(alkyltin mercaptides) and their use as heat stabilizers
AssigneeGalata Chemicals, LLC
InventorPeter FRENKEL
Life of this patent
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Abstract
A composition of liquid bis(alkyltin mercaptide) compounds containing 4-6 thio-ester groups of formula (I): where a, b, c and d are equal to 1 or 2, and a+b=c+d=3, R′ is a linear, branched, or cyclic C1-C12 hydrocarbon group, SR″ and R″S are independently selected from an alkyl thioglycolate group, an alkyl thiopropionate or a 2-mercaptoethyl carboxylate group, where the alkyl is a linear, branched, or cyclic C6-C18 hydrocarbon group; and SR′″S is an alkylene glycol di-thioester group, where the alkyl groups are linear or branched C1-C6 hydrocarbon groups.
Claims36
A composition of liquid bis(alkyltin mercaptide) compounds containing 4-6 thio-ester groups of formula (I):
- where
- a, b, c and d are equal to 1 or 2, and a+b=c+d=3,
- R′ is a linear, branched or cyclic C1-C12 hydrocarbon group,
- SR″ and R″S are independently selected from an alkyl thioglycolate group, an alkyl thiopropionate or a 2-mercaptoethyl carboxylate group, where the alkyl is a linear, branched or cyclic C6-C18 hydrocarbon group;
- and
- SR′″S is an alkylene glycol di-thioester group, where the alkyl groups are linear or branched C1-C6 hydrocarbon groups.
A process for the preparation of bis(alkyltin mercaptide) compounds containing 4 thioester groups, comprising:
- reacting dialkyltin oxides with alkylene glycol di-thioesters in the presence of at least one of a monoalkyltin tris-thioesters and a dialkyltin bis-thioester according to equations (1a) or (1b):
- wherein no hydrocarbon solvent is used in the reaction, R′2SnO is selected from di-n-butyltin oxide, di-n-octyltin oxide or a mixture thereof, and R′ of R′2SnO, R′Sn(SR″)3 and R′2Sn(SR″)2 can be the same or different,
- H2(SR′″S) is selected from ethylene glycol dithioglycolate, 1,2-propylene glycol dithioglycolate, 1,3-propylene glycol dithioglycolate, ethylene glycol dithiopropionate or mixtures thereof,
- R′ is an alkyl linear, branched or cyclic C1-C12 hydrocarbon group,
- SR″ and R″S are independently selected from an alkyl thioglycolate group, an alkyl thiopropionate or a 2-mercaptoethyl carboxylate group, where the alkyl is a linear, branched or cyclic C6-C18 hydrocarbon group;
- and
- SR′″S is an alkylene glycol di-thioester group, where the alkyl groups are linear or branched C1-C6 hydrocarbon groups,
- wherein the reaction is conducted at a temperature of 60.0 to 120.0° C. for a time of 1.0 to 3.0 hours.
A process for the preparation of bis(alkyltin mercaptide) compounds containing 4 or 5 thio-ester groups comprising:
- reacting dialkyltin alkylene glycol dithioesters with either di-alkyltin bis-thioester or mono-alkyltin tris-thioester according to equations (2) or (3), wherein no hydrocarbon solvent is used in the synthesis:
- where R′ of R′2Sn(SR′″S), R′Sn(SR″)3 and R′2Sn(SR″)2 can be the same or different,
- R′ is a linear, branched or cyclic C1-C12 hydrocarbon group,
- SR″ and R″S are independently selected from an alkyl thioglycolate group, an alkyl thiopropionate or a 2-mercaptoethyl carboxylate group, where the alkyl is a linear, branched or cyclic C6-C18 hydrocarbon group;
- and
- SR′″S is an alkylene glycol di-thioester group, where the alkyl groups are linear or branched C1-C6 hydrocarbon groups,
- wherein the reaction is conducted at a temperature of 25.0 to 120.0° C. for a time of 1.0 to 3.0 hours.
A process for the synthesis of bis(alkyltin mercaptide) compounds containing 4 to 6 thioester groups comprising:
- reacting alkylene glycol di-thioesters with either mono-alkyltinmono-chloro-bis-thioglycolates or dialkyltin (chloro-thioglycolates) according to equations (4) or (5):
- wherein R′ is an alkyl linear, branched or cyclic C1-C12 hydrocarbon group,
- —R″ is an alkyl thioglycolate, an alkyl thiopropionate or 2-mercaptoethyl carboxylate group, where the R″ alkyl group is linear, branched or cyclic C6-C18 hydrocarbon group;
- and
- —SR′″S is an alkylene glycol dithioester, selected from alkylene glycol di-thioglycolate or alkylene glycol di-thiopropionate, where the R′″ alkyl group is linear or branched C1-C6 hydrocarbon group,
- wherein reactions (4) and (5) are performed in the presence of ammonia, and R′SnCl(SR″)2 or R′2Sn[Cl(SR″)] are added last, the product yield is 85.0 to 95.0%,
- and R′SnCl(SR″)2 is prepared according to equation (6):
- where R′ of R′Sn(SR″)3 and R′SnCl3 can be the same or different,
- and where R′2Sn[Cl(SR″)] is prepared according to equation (7):
- where R′ of R′2Sn(SR″)2 and R′2SnCl2 can be the same or different,
- wherein reactions (4) and (5) are conducted at a temperature of 40 to 100° C. over 0.5 to 2.0 hours, and reactions (6) and (7) are conducted at 50 to 180° C. over 0.5 to 2.0 hours.
Dependencies are inferred from the claim text.