Isocyanatosilanes with thiourethane structure

Patent metadata

Field	Value
Publication number	US-9637506-B2
Application number	US-201314425103-A
Country	US
Kind code	B2
Filing date	Aug 29, 2013
Priority date	Sep 4, 2012
Publication date	May 2, 2017
Grant date	May 2, 2017

Abstract

The invention relates to a method for producing compounds containing isocyanate and silane groups by reacting at least A) one monomeric diisocyanate containing aliphatically, cycloaliphatically, araliphatically and/or aromatically bonded isocyanate groups with B) a mercaptosilane, characterized in that component A) is reacted with component B) in an equivalent ratio of isocyanate groups to mercapto groups of at least 06:01 to at most 40:1. Furthermore, the invention relates to the products which can be obtained using the method according to the invention, and to a composition containing compounds that contain isocyanate and silane groups. Moreover, the invention relates to the use of the products which can be obtained using the method according to the invention and the composition according to the invention as starting components in the production of silane group-containing polyurethanes, cross-linkable binders, varnish, and raw materials for sealants or adhesives.

First claim

The invention claimed is:

1. A method for preparing polyurethanes containing silane groups comprising reacting a starting material mixture consisting of the compound containing isocyanate groups and silane groups-obtained by reacting
A) a monomeric diisocyanate having aliphatically, cycloaliphatically, araliphatically and/or aromatically bonded isocyanate groups
with
B) a mercaptosilane,
wherein component A) is reacted with component B) in a ratio of equivalents of isocyanate groups to mercapto groups of at least 6:1 to at most 40:1, and wherein, after the reaction of components A) with B), any unconverted excess of monomeric diisocyanates A) is removed from the reaction product by thin-film distillation down to a residual content of less than 1% by weight, based on the total mass of the reaction product
or a composition consisting of a) a compound of the general formula (III) containing isocyanate groups and silane groups,

and
b) a compound of the general formula (IV) containing silane groups

where
R 1 , R 2 and R 3 are identical or different radicals and each is a saturated or unsaturated, linear or branched, aliphatic or cycloaliphatic radical or an optionally substituted aromatic or araliphatic radical having up to 18 carbon atoms, which may optionally contain up to 3 heteroatoms from the group of oxygen, sulfur, nitrogen, and
X is a linear or branched organic radical having at least 2 carbon atoms,
Y is a linear or branched, aliphatic or cycloaliphatic radical having 4 to 18 carbon atoms or an optionally substituted aromatic or araliphatic radical having 6 to 18 carbon atoms,
wherein component a) makes up a proportion of ≧85% by weight, component b) a proportion of ≦15% by weight, of the total mass of components a) and b),
and a polyol selected from the group consisting of a monomeric polyhydric alcohol, a monomeric ether alcohol, a monomeric ester alcohol, a polyether polyol, a polyester polyol, a polycarbonate polyol and a polyacrylate alcohol.

2. The method as claimed in claim 1 , wherein mercaptosilanes of the general formula (I) or mixtures thereof are used as component B)

in which
R 1 , R 2 and R 3 are identical or different radicals and each is a saturated or unsaturated, linear or branched, aliphatic or cycloaliphatic radical or an optionally substituted aromatic or araliphatic radical having up to 18 carbon atoms, which may optionally contain up to 3 heteroatoms from the group of oxygen, sulfur, nitrogen, and
X is a linear or branched organic radical having at least 2 carbon atoms.

3. The method as claimed in claim 2 , wherein mercaptosilanes of the general formula (I) or mixtures thereof are used as component B), where
R 1 , R 2 and R 3 are identical or different radicals and each is a saturated, linear or branched, aliphatic or cycloaliphatic radical having up to 6 carbon atoms, which may optionally contain up to 3 oxygen atoms and
X is a linear or branched alkylene radical having 2 to 10 carbon atoms.

4. The method as claimed in claim 3 , wherein mercaptosilanes of the general formula (I) or mixtures thereof are used as component B), where
R 1 , R 2 and R 3 are identical or different radicals and each is an alkyl radical having up to 6 carbon atoms and/or alkoxy radicals containing up to 3 oxygen atoms, with the proviso that at least one of the R 1 , R 2 and R 3 radicals is such an alkoxy radical, and
X is a propylene radical (—CH 2 —CH 2 —CH 2 —).

5. The method as claimed in claim 1 , wherein monomeric diisocyanates of the general formula (II) or mixtures thereof are used as component A)
OCN—Y—NCO  (II)

where
Y is a linear or branched, aliphatic or cycloaliphatic radical having 4 to 18 carbon atoms or an optionally substituted aromatic or araliphatic radical having 6 to 18 carbon atoms.

6. The method as claimed in claim 5 , wherein component A) is 1,6-diisocyanatohexane, 1-isocyanato-3,3,5-trimethyl-5-isocyanatomethylcyclohexane, 2,4′- and/or 4,4′-diisocyanatodicyclohexylmethane or a mixture thereof.

7. The method as claimed in claim 1 , wherein component A) is reacted with component B) in a ratio of equivalents of isocyanate groups to mercapto groups of at least 8:1 to at most 30:1.

8. The method as claimed in claim 1 , wherein component A) is reacted with component B) in a ratio of equivalents of isocyanate groups to mercapto groups of at least 10:1 to at most 25:1.

9. A method for producing crosslinkable raw materials for varnishes, sealants or adhesives or of crosslinkable binders comprising reacting a starting material mixture consisting of the compound containing isocyanate groups and silane groups-obtained by reacting
A) a monomeric diisocyanate having aliphatically, cycloaliphatically, araliphatically and/or aromatically bonded isocyanate groups
with
B) a mercaptosilane,
wherein component A) is reacted with component B) in a ratio of equivalents of isocyanate groups to mercapto groups of at least 6:1 to at most 40:1, and wherein, after the reaction of components A) with B), any unconverted excess of monomeric diisocyanates A) is removed from the reaction product by thin-film distillation down to a residual content of less than 1% by weight, based on the total mass of the reaction product
or a composition consisting of a) a compound of the general formula (III) containing isocyanate groups and silane groups,

and
b) a compound of the general formula (IV) containing silane groups

where
R 1 , R 2 and R 3 are identical or different radicals and each is a saturated or unsaturated, linear or branched, aliphatic or cycloaliphatic radical or an optionally substituted aromatic or araliphatic radical having up to 18 carbon atoms, which may optionally contain up to 3 heteroatoms from the group of oxygen, sulfur, nitrogen, and
X is a linear or branched organic radical having at least 2 carbon atoms,
Y is a linear or branched, aliphatic or cycloaliphatic radical having 4 to 18 carbon atoms or an optionally substituted aromatic or araliphatic radical having 6 to 18 carbon atoms,
wherein component a) makes up a proportion of ≧85% by weight, component b) a proportion of ≦15% by weight, of the total mass of components a) and b),
and a polyol selected from the group consisting of a monomeric polyhydric alcohol, a monomeric ether alcohol, a monomeric ester alcohol, a polyether polyol, a polyester polyol, a polycarbonate polyol and a polyacrylate alcohol.

10. A polyurethane containing silane groups, obtained by reacting a starting material mixture consisting of the compound containing isocyanate groups and silane groups-obtained by reacting
A) a monomeric diisocyanate having aliphatically, cycloaliphatically, araliphatically and/or aromatically bonded isocyanate groups
with
B) a mercaptosilane,
wherein component A) is reacted with component B) in a ratio of equivalents of isocyanate groups to mercapto groups of at least 6:1 to at most 40:1, and wherein, after the reaction of components A) with B), any unconverted excess of monomeric diisocyanates A) is removed from the reaction product by t

Assignees

• Bayer Materialscience Ag
• Covestro Deutschland Ag

Inventors

• Laas Hans-Josef

Classifications

• C08G18/73 Primary

  acyclic · CPC title

• C08G18/289

  containing silicon · CPC title

• C07F7/0818 Primary

  Chemistry & Metallurgy · mapped topic

• C08G18/758

  containing two or more cycloaliphatic rings · CPC title

• C08G18/72

  Polyisocyanates or polyisothiocyanates · CPC title