High purity monoalkyltin compounds and uses thereof
View Patent ↗The present invention relates to high purity monoalkyltin compounds, more specifically to alkyltin compound compositions containing monoalkyltin as major compound, and minor quantities of di- and/or trialkyltin compounds. The present invention also relates to the preparation processes of such high purity monoalkyltin compounds, as well as to the uses of said monoalkyltin compounds as chlorine-containing polymer-stabilizers, glass coating chemicals and catalysts, as well as articles comprising at least one polymer matrix and a high purity monoalkyltin compound.
1. Composition comprising:
from 85 wt % to 99.999 wt % of at least one monoalkyltin compound of formula RSn(T) 3 ;
from 0.001 wt % to 10 wt % of at least one di-alkyltin compound of formula R 2 Sn(T) 2 ;
from 0.001 wt % to 5 wt % of at least one tri-alkyltin compound of formula R 3 Sn(T); and
from 0 wt % to 5 wt % of one or more impurities,
wherein R is linear, branched or cyclic C 1 -C 20 alkyl and T is a ligand selected from the group consisting of thioglycolate esters, 2-ethylhexylthioglycolate esters, iso-octylthioglycolates, iso-butylthioglycolates, thioglycolate, hydroxyl, carboxylates, maleates, diketonates, alcoholates, and 2-ethylhexylmercaptoacetate.
2. Composition according to claim 1 , wherein the weight ratio of (mono-alkyltin compound)/(di-alkyltin compound) is not less than 90/10.
3. Composition according to claim 1 , wherein the weight ratio of (mono-alkyltin compound)/(di-alkyltin compound) is not less than 99/1.
4. Composition according to claim 1 , wherein R is selected from the group consisting of methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, iso-octyl, and decyl.
5. Composition according to claim 1 , wherein RSn(T) 3 is RSn[tris(2-ethylhexylmercaptoacetate)].
6. Composition according to claim 5 , wherein RSn(T) 3 is selected from the group consisting of monomethyltin[tris(2-ethylhexylmercaptoacetate)], mono-n-butyltin[tris(2-ethylhexyl-mercaptoacetate)], mono-n-octyl[tris(2-ethylhexylmercaptoacetate)], and mixtures thereof.
7. Composition according to claim 1 further comprising at least one co-stabiliser and/or at least one additive.
8. Composition according to claim 7 , wherein the co-stabiliser is selected from the group consisting of epoxydised soy bean oil, dihydropyridine-based compounds, α-phenylindole, polyols, disaccharide alcohols, perchlorate-based compounds, glycidyl compounds, layered lattice compounds, zeolite compounds, phosphite compounds, β-diketones, β-ketoesters, mercaptocarboxylic esters, metal soaps, amino- and/or thiouracils, hydrazides, and mixtures thereof.
9. Composition according to claim 7 , further comprising at least one dihydropyridine-based compound, and optionally at least one perchlorate compound.
10. Composition according to claim 7 , wherein the additive is from the group consisting of stabilisers, auxiliaries and processing aids, lubricants, plasticizers, pigments, fillers, epoxidized fatty acid esters, antioxidants, UV absorbers and light stabilisers, optical brighteners, impact modifiers, gelling agents, antistats, biocides, metal passivators, flame retardants, blowing agents, antifog agents, compatibilisers and anti plate-out agents, and mixtures thereof.
11. Composition comprising a chlorine-containing polymer and a composition comprising:
from 85 wt % to 99.999 wt % of at least one monoalkyltin compound of formula RSn(T) 3 ;
from 0.001 wt % to 10 wt % of at least one di-alkyltin compound of formula R 2 Sn(T) 2 ;
from 0.001 wt % to 5 wt % of at least one tri-alkyltin compound of formula R 3 Sn(T); from 0 wt % to 5 wt % of one or more impurities; and optionally at least one co-stabiliser and/or one or more additive(s), wherein R is linear, branched or cyclic C 1 -C 20 alkyl and T is a ligand selected from the group consisting of thioglycolate esters, 2-ethylhexylthioglycolate esters, iso-octylthioglycolates, iso-butylthioglycolates, thioglycolate, hydroxyl, carboxylates, maleates, diketonates, alcoholates, and 2-ethylhexylmercaptoacetate.
12. Article comprising at least one polymer matrix and a composition comprising: from 85 wt % to 99.999 wt % of at least one monoalkyltin compound of formula RSn(T) 3 ; from 0.001 wt % to 10 wt % of at least one di-alkyltin compound of formula R 2 Sn(T) 2 ; from 0.001 wt % to 5 wt % of at least one tri-alkyltin compound of formula R 3 Sn(T); from 0 wt % to 5 wt % of one or more impurities; and
optionally one or more additive(s) and/or co-stabiliser(s), wherein R is linear, branched or cyclic C 1 -C 20 alkyl and T is a ligand selected from the group consisting of thioglycolate esters, 2-ethylhexylthioglycolate esters, iso-octylthioglycolates, iso-butylthioglycolates, thioglycolate, hydroxyl, carboxylates, maleates, diketonates, alcoholates, and 2-ethylhexylmercaptoacetate.
13. Article according to claim 12 , wherein the matrix is a chlorine-containing polymer.
14. Process of preparation of a composition comprising: from 85 wt % to 99.999 wt % of at least one monoalkyltin compound of formula RSn(T) 3 ; from 0.001 wt % to 10 wt % of at least one di-alkyltin compound of formula R 2 Sn(T) 2 ; from 0.001 wt % to 5 wt % of at least one tri-alkyltin compound of formula R 3 Sn(T); and from 0 wt % to 5 wt % of one or more impurities, wherein R is linear, branched or cyclic C 1 -C 20 alkyl and T is a ligand selected from the group consisting of thioglycolate esters, 2-ethylhexylthioglgcolate esters, iso-octglthioglycolates, iso-butylthioglycolates, thioglycolate, hydroxyl, carboxylates, maleates, diketonates, alcoholates, and 2-ethylhexylmercaptoacetate, the process comprising:
α) hydrostannylating a 1-alkene to the corresponding mono-alkyltin trihalide RSn(Hal) 3 in the presence of a transition metal catalyst, tin(II) dihalide and hydrogen halide; and
β) converting the mono-alkyltin trihalide RSn(Hal) 3 to RSn(T) 3 by contacting the mono-alkyltin trihalide RSn(Hal) 3 with a compound of formula H-T in the presence of a suitable base or, alternatively, converting RSn(Hal) 3 to alkylstannoic acid of formula RSn(O)OH using a hydroxide base followed by contacting the alkylstannoic acid with a compound of formula H-T under elimination of water.
15. Process according to claim 14 , wherein said stannous halide is SnCl 2 and said hydrogen halide is HCl.
16. Process according to claim 14 , wherein R is selected from the group consisting of methyl, n-butyl, iso-octyl and n-octyl.
17. Process according to claim 14 , wherein T is selected from the group consisting of 2-ethyl hexyl mercaptoacetate and hydroxyl.
18. Process of preparation of a composition comprising: from 85 wt % to 99.999 wt % of at least one monoalkyltin compound of formula RSn(T) 3 ; from 0.001 wt % to 10 wt % of at least one di-alkyltin compound of formula R 2 Sn(T) 2 ; from 0.001 wt % to 5 wt % of at least one tri-alkyltin compound of formula R 3 Sn(T); and from 0 wt % to 5 wt % of one or more impurities, wherein R is linear, branched or cyclic C 1 -C 20 alkyl and T is a ligand selected from the group consisting of thioglycolate esters, 2-ethylhexylthioglycolate esters, iso-octylthioglycolates, iso-butylthioglycolates, thioglycolate, hydroxyl, carboxylates, maleates, diketonates, alcoholates, and 2-ethylhexylmercaptoacetate, the process comprising the steps of:
a) preparing a solution of stannous halide SnHal 2 in a solvent, together with a transition metal-based catalyst;
b) reacting the obtained solution with a molar excess of an alkene or cycloalkene precursor of the R radical, at a temperature ranging between room temperature to 200° C. in the presence of hydrogen halide (H-Hal) and optionally metallic tin (Sn);
c) optionally removing the solvent of the reaction medium, by stripping or vacuum-distillation of the solvent;
d) optionally filtering the crude reaction medium;
e) adding a 2- to 5-fold molar excess (relative to the obtained monoalkyltin trihalide) of H-T and water under stirring;
f) neutralising the reaction medium with alkali or alkaline-earth hydroxide, and forming a water layer and an organic layer;
g) separating the water layer from the organic layer; and
h) removing the solvent from the organic layer, and optionally filtering to recover RSn(T) 3 of high purity.
19. Process according to any of claim 18 , wherein R is selected from the group consisting of methyl, n-butyl, iso-octyl and n-octyl.
20. Process according to claim 18 , wherein T is selected from the group consisting of 2-ethylhexyl mercaptoacetate and OH.