Silane functional binder with thiourethane structure

Patent metadata

Field	Value
Publication number	US-9353210-B2
Application number	US-201314425206-A
Country	US
Kind code	B2
Filing date	Aug 28, 2013
Priority date	Sep 4, 2012
Publication date	May 31, 2016
Grant date	May 31, 2016

Abstract

The invention relates to a method for producing polyurethanes containing silane groups by reacting at least A) a composition containing a) one or more compounds containing isocyanate and silane groups of general formula (I) and b) <=1 percent by weight, relative to the total mass of composition A), one or more monomeric diisocyanates with aliphatically, cycloaliphatically, araliphatically and/or aromatically bonded isocyanate groups of general formula (II), where R1, R2 and R3 are the same or different radicals and respectively indicate a saturated or unsaturated, linear or branched, aliphatic or cycloaliphatic or an optionally substituted aromatic or araliphatic radical with up to 18 carbon atoms, which can contain optionally up to 3 heteroatoms from the series oxygen, sulphur, nitrogen, X is a linear or branched organic radical with at least 2 carbon atoms and Y is a linear or branched, aliphatic or cycloaliphatic radical with 4 to 18 carbon atoms or an optionally substituted aromatic or araliphatic radical with 6 to 18 carbon atoms, with B) an at least difunctional polyol with a numerically average molecular weight Mn of 62 to 22000 g/mol, preferably 90 to 12000 g/mol, while maintaining an equivalent ratio of isocyanate groups to hydroxyl groups of 0.7:1 to 1.2:1. The invention further relates to the products which can be obtained using the method according to the invention. Moreover, the invention relates to the use of the products which can be obtained using the method according to the invention as starting components in the production of cross-linkable binders, varnish, and raw materials for sealants or adhesives.

First claim

The invention claimed is:

1. A process for preparing polyurethanes containing silane groups, comprising reacting at least
A) a composition containing
a) a compound of the general formula (I) containing one or more isocyanate and silane groups

 and
b) ≦1% by weight, based on the total mass of composition A), of one or more monomeric diisocyanate having aliphatically, cycloaliphatically, araliphatically and/or aromatically bonded isocyanate groups of the general formula (II)
OCN—Y—NCO  (II)

 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,
X is a linear or branched organic radical having at least 2 carbon atoms and
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,

with
B) an at least difunctional polyol having a number-average molecular weight M n of 62 to 22 000 g/mol, preferably 90 to 12 000 g/mol,
while maintaining a ratio of equivalents of isocyanate groups to hydroxyl groups of 0.7:1 to 1.2:1.

2. The process for preparing polyurethanes containing silane groups as claimed in claim 1 , wherein composition A) additionally comprises compounds c) of the general formula (III) in a proportion of 2% to 15% by weight, based on the total mass of components a) and c),

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,
X is a linear or branched organic radical having at least 2 carbon atoms and
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.

3. The process as claimed in claim 2 , wherein composition A) comprises
a) ≧85% by weight of compounds of the general formula (I),
b) ≦1% by weight of one or more monomeric diisocyanate having aliphatically, cycloaliphatically, araliphatically and/or aromatically bonded isocyanate groups of the general formula (II) and
c) ≦15% by weight of compounds of the general formula (III),

where the proportion of each of a) and c) relates to the total mass of the compounds a) and c), and the proportion of b) relates to the total mass of composition A), and 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,
X is a linear or branched organic radical having at least 2 carbon atoms and
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.

4. The process as claimed in claim 1 , wherein, for the formulae (I) and (II) of components a) and b), or for the formulae (I), (II) and (III) of components a), b) and c),
Y is a linear or branched, aliphatic or cycloaliphatic radical having 6 to 13 carbon atoms.

5. The process as claimed in claim 1 , wherein, for the formula (I) of component a) or the formulae (I) and (III) of components a) and c),
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.

6. The process as claimed in claim 1 , wherein, for the formula (I) of component a) or the formulae (I) and (III) of components a) and c),
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 radical 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 —).

7. The process as claimed in claim 1 , wherein, for the formula (I) of component a) or the formulae (I) and (III) of components a) and c),
R 1 , R 2 and R 3 are identical or different radicals and each is methyl, methoxy or ethoxy, with the proviso that at least one of the R1, R2 and R3 radicals is a methoxy or ethoxy radical and
X is a propylene radical (—CH 2 —CH 2 —CH 2 —).

8. The process as claimed in claim 1 , wherein the polyol component B) has a mean functionality of 2 to 6, preferably of 2 to 4.

9. The process as claimed in claim 1 , wherein component B) is a polyhydric alcohol, an ether alcohol or an ester alcohol and/or a polymeric polyol, said polymeric polyol having a number-average molecular weight M n of 200 to 22 000 g/mol.

10. The process as claimed in claim 9 , wherein component B) is a polyhydric alcohol and/or an ether alcohol or an ester alcohols containing 2 to 14 carbon atoms.

11. The process as claimed in claim 10 , wherein component B) is a polyether polyol, a polyester polyol, a polycarbonate polyol and/or a polyacrylate polyol.

12. A polyurethanes containing a silane group, obtained by the process as claimed in claim 1 .

13. A method for the production of a crosslinkable binder comprising utilizing the polyurethane as claimed in claim 12 as a starting component.

14. A method the production of crosslinkable raw materials for paints, sealants or adhesives comprising utilizing the polyurethane as claimed in claim 12 as a starting component.

15. A crosslinkable binder comprising the polyurethane as claimed in claim 12 .

Assignees

• Bayer Materialscience Ag
• Covestro Deutschland Ag

Inventors

• Laas Hans-Josef
• Vega Sanchez Berta
• Kahl Lothar

Classifications

• C08G18/289

  containing silicon · CPC title

• C09D175/04

  Polyurethanes · CPC title

• C08G18/755

  and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate · CPC title

• C09J175/14

  Polyurethanes having carbon-to-carbon unsaturated bonds · CPC title

• C08G18/758

  containing two or more cycloaliphatic rings · CPC title