Novel catalysts for reaction between an isocyanate and an alcohol
AssigneeBluestar Silicones France SAS
InventorsChristian Maliverney, Laurent Saint-Jalmes
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Abstract
Catalysts, which are free of tin, are described for the reaction between an isocyanate and an alcohol, which is a key step for preparing polyurethane polymers.
Claims16
A process for preparing a compound A having at least one urethane functional group, the process comprising a stage 1) which comprises reacting a compound B, having at least one isocyanate functional group, with a compound D, having at least one hydroxyl functional group, in the presence of a catalytically effective amount of at least one catalyst C, wherein the catalyst C is a metal complex or salt of following formula (1):
- [Zn(L1)l1(L2)l2(Y)x] (1)
- in which:
- l1≧1 and l2=0 or 1;
- with l1+l2=2, x=0, 1 or 2,
- the symbol L1 represents a ligand which is a β-dicarbonylato anion or the enolate anion of a β-dicarbonyl compound or an acetylacetato anion derived from a β-ketoester,
- when l1=2, the symbols L1 can be identical or different,
- the symbol L2 represents an anionic ligand which is different from L1,
- the symbol Y represents a neutral ligand, and
- with the additional condition that the metal complex or salt C of formula (1) is not the compound zinc diacetylacetonate or [Zn(acac)2].
A process for preparing a compound A having at least one urethane functional group, the process comprising a stage 1) which comprises reacting a compound B, having at least one isocyanate functional group, with a compound D, having at least one hydroxyl functional group, in the presence of a catalytically effective amount of at least one catalyst C, wherein the catalyst C is a metal complex or salt of following formula (1):
- [Zn(L1)l1(L2)l2(Y)x] (1)
- in which:
- l1≧1 and l2=0 or 1;
- with l1+l2=2, x=0, 1 or 2,
- the symbol L2 represents an anionic ligand which is different from L1,
- the symbol Y represents a neutral ligand, and
- the symbol L1 is a β-diketonato anion derived from a β-diketone of formula R1COCHR2COR3 (2) and said β-diketone is selected from the group consisting of β-diketones:
- 2,4-hexanedione;
- 2,4-heptanedione;
- 3,5-heptanedione;
- 3-ethyl-2,4-pentanedione;
- 5-methyl-2,4-hexanedione;
- 2,4-octanedione;
- 3,5-octanedione;
- 5,5-dimethyl-2,4-hexanedione;
- 6-methyl-2,4-heptanedione;
- 2,2-dimethyl-3,5-nonanedione;
- 2,6-dimethyl-3,5-heptanedione;
- 2-acetylcyclohexanone (Cy-acac);
- 2,2,6,6-tetramethyl-3,5-heptanedione (t-Bu-acac);
- 2,2,7-trimethyl-3,5-octanedione;
- 1,1,1,5,5,5-hexafluoro-2,4-pentanedione (F-acac);
- benzoylacetone;
- dibenzoylmethane;
- 3-methyl-2,4-pentanedione;
- 3-acetylpentane-2-one;
- 3-acetyl-2-hexanone;
- 3-acetyl-2-heptanone;
- 3-acetyl-5-methyl-2-hexanone;
- stearoylbenzoylmethane;
- octanoylbenzoylmethane;
- 4-(t-butyl)-4′-methoxydibenzoylmethane;
- 4,4′-dimethoxydibenzoylmethane;
- 4,4′-di(tert-butyl)di-benzoylmethane and 2,4-undecanedione.
A compound selected from formulae (7) to (9):
- (7):
- [Zn(UDD)2], with (UDD)=a 2,4-undecanedionato anion or an enolate anion of 2,4-undecanedione,
- (8):
- [Zn(TMOD)2(N,N′-dimethylethylenediamine)], with (TMOD)=a 2,2,7-trimethyl-3,5-octanedionato anion or an enolate anion of 2,2,7-trimethyl-3,5-octanedione, and
- (9):
- [Zn(TMOD)2(N-propylethylenediamine)], with (TMOD)=a 2,2,7-trimethyl-3,5-octanedionato anion or an enolate anion of 2,2,7-trimethyl-3,5-octanedione.
Dependencies are inferred from the claim text.