Amidine group—or guanidine group—containing silane

Patent metadata

Field	Value
Publication number	US-10100068-B2
Application number	US-201515300842-A
Country	US
Kind code	B2
Filing date	Apr 16, 2015
Priority date	Apr 16, 2014
Publication date	Oct 16, 2018
Grant date	Oct 16, 2018

Abstract

A silane of the formula (I) containing at least one aliphatic amidine group- or guanidine group-containing alkoxy group, to a method for producing same, to conversion products thereof, and to the use thereof as a catalyst in curable compositions, in particular based on silane group-containing polymers. The silane of the formula (I) is largely odorless and non-volatile at room temperature. The silane accelerates the hydrolysis and condensation reaction of silane groups very effectively without impairing the storage stability of silane group-containing polymers. Additionally, the silane is very tolerable in silane group-containing compositions, whereby such compositions are not prone to separate, migrate, or evaporate the catalyst.

First claim

The invention claimed is:

1. A silane of the formula (I),

in which
Z is an amidine or guanidine group bonded via a nitrogen atom,
A is a divalent aliphatic or cycloaliphatic or arylaliphatic hydrocarbon radical having 2 to 20 C atoms, which optionally comprises ether-oxygen or secondary or tertiary amine-nitrogen,
e is 0 or 1, f is 0 or 1 or 2, and g is an integer from 1 to 4, and the sum (e+f+g) is an integer from 1 to 4,
R 6 either is an alkoxy radical having 1 to 12 C atoms which optionally contains ether-oxygen, or is a ketoximato radical having 1 to 13 C atoms,
R 7 is a monovalent hydrocarbon radical having 1 to 12 C atoms, and
Y is a monovalent hydrocarbon radical having 1 to 20 C atoms which optionally has a terminal mercapto group, epoxide group, (meth)acryloyl group, amidine group, guanidine group, urethane group or urea group or has a terminal amino group of the formula —NHR 8 , and which optionally contains ether-oxygen or secondary amine-nitrogen, where R 8 is a hydrogen radical or an alkyl or cycloalkyl or aralkyl radical having 1 to 8 C atoms; or is a radical

where the silane of the formula (I) contains no nitrogen atom which is bonded directly to an aromatic ring or is part of a heteroaromatic ring system.

2. The silane as claimed in claim 1 , wherein
Z is

where
R 0 is a hydrogen radical or is an alkyl or cycloalkyl or aralkyl radical having 1 to 8 C atoms,
R 1 is a hydrogen radical or is an alkyl or cycloalkyl or aralkyl radical having 1 to 8 C atoms, or together with R 2 forms R 9 ,
R 2 is a hydrogen radical or is an alkyl, cycloalkyl or aralkyl radical having 1 to 18 C atoms, which optionally contains ether-oxygen or tertiary amine-nitrogen, or together with R 1 forms R 9 ,
R 3 is —NR 4 R 5 or is a hydrogen radical or is an alkyl or cycloalkyl or aralkyl radical having 1 to 12 C atoms,
R 4 and R 5 independently of one another are each a hydrogen radical or are an alkyl, cycloalkyl or aralkyl radical having 1 to 18 C atoms, which optionally contains ether-oxygen or tertiary amine-nitrogen, and
R 9 is 1,2-ethylene or 1,2-propylene or 1,3-propylene or 1,3-butylene or 1,3-pentylene, where
R 2 and R 0 may also together be an alkylene radical having 3 to 6 C atoms, which optionally contains ether-oxygen or tertiary amine-nitrogen,
R 2 and R 3 may also together be an alkylene radical having 3 to 6 C atoms,
R 4 and R 5 may also together be an alkylene radical having 4 to 7 C atoms, which optionally contains ether-oxygen or tertiary amine-nitrogen, and
R 2 and R 5 may also together be an alkylene radical having 2 to 12 C atoms.

3. The silane as claimed in claim 2 , wherein Z is

where R 3 is a hydrogen radical or is an alkyl, cycloalkyl or aralkyl radical having 1 to 12 C atoms.

4. The silane as claimed in claim 2 , wherein Z is

where R 2 and R 5 independently of one another are each an alkyl, cycloalkyl or aralkyl radical having 1 to 12 C atoms, which optionally contains ether-oxygen or tertiary amine-nitrogen.

5. The silane as claimed in claim 1 , wherein A is selected from the group consisting of 1,2-ethylene, 1,2-propylene, 1,3-propylene, 1,4-butylene, 1,1-dimethyl-1,2-ethylene, 1,5-pentylene, 1,6-hexylene, (1,5,5-trimethylcyclohexan-1-yl)methane-1,3,3-oxa-1,5-pentylene and 3,6-dioxa-1,8-octylene.

6. The silane as claimed in claim 1 , wherein Y is selected from the group consisting of methyl, octyl, isooctyl, phenyl, vinyl, 3-aminopropyl, N-(2-aminoethyl)-3-aminopropyl, 3-mercaptopropyl, 3-glycidyloxypropyl, 3-acryloyloxypropyl, 3-methacryloyloxypropyl, and a radical of the formula

7. A process for preparing the silane as claimed in claim 1 , wherein
at least one amine of the formula (IIa) or (IIb),
HO-A-NHR 1   (IIa)

HO-A-NH—R 9 —NH 2   (IIb)

optionally at least one amine of the formula R 2 —NH—R 0 ,
at least one reagent for introducing amidine or guanidine groups, and
at least one alkoxy- or ketoximato-silane are reacted with one another.

8. A reaction product containing amidine or guanidine groups which is obtained from a silane as claimed in claim 1 , wherein (e+f+g) is 1 or 2 or 3, by condensation with at least one compound containing silanol groups.

9. The reaction product as claimed in claim 8 , wherein it is obtained by hydrolysis and subsequent condensation reactions solely from the silane as formula (I), wherein (e+f+g) is 1 or 2 or 3, and represents an oligomeric descendant of the silane, containing silanol and/or siloxane groups.

10. The reaction product as claimed in claim 8 , wherein it is obtained from the condensation with at least one silicone oil of the formula

where
n is an integer in the range from 3 to 200,
R 10 is a monovalent hydrocarbon radical having 1 to 6 C atoms, and
R 11 is a hydroxyl radical or is an alkyl or alkoxy or ketoximato radical having 1 to 13 C atoms.

11. A process for curing a curable composition comprising a step of providing, as a catalyst, the silane as claimed in claim 1 and/or a condensation product between said silane wherein (e+f+g) is 1 or 2 or 3 and at least one compound containing silanol groups.

12. The process as claimed in claim 11 , wherein the curable composition comprises at least one polymer containing silane groups.

13. The process as claimed in claim 12 , wherein the polymer containing silane groups is selected from the group consisting of polyorganosiloxanes having terminal silane groups and organic polymers containing silane groups.

14. A composition comprising at least one silane as claimed in claim 1 and/or at least one condensation product between said at least one silane wherein (e+f+g) is 1 or 2 or 3 and at least one compound containing silanol groups and at least one polymer containing silane groups.

15. The composition as claimed in claim 14 , wherein it constitutes an adhesive or a sealant or a coating.

Assignees

• Sika Tech Ag

Inventors

• Burckhardt Urs
• Cannas Rita

Classifications

• C08G77/388

  containing nitrogen · CPC title

• C09D183/08

  containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen · CPC title

• C07C279/18

  having nitrogen atoms of guanidine groups bound to carbon atoms of six-membered aromatic rings · CPC title

• C07C279/16

  having nitrogen atoms of guanidine groups bound to carbon atoms of rings other than six-membered aromatic rings · CPC title

• C08G77/26

  nitrogen-containing groups · CPC title