Amidine catalyst for curable compositions

Patent metadata

Field	Value
Publication number	US-11292771-B2
Application number	US-202016843379-A
Country	US
Kind code	B2
Filing date	Apr 8, 2020
Priority date	Jun 22, 2015
Publication date	Apr 5, 2022
Grant date	Apr 5, 2022

Abstract

The present invention relates to an amidine of the formula (I) and its use as a catalyst for crosslinking a curable composition. The amidine of the formula (I) contains at least one aliphatic amidine group. It is substantially odorless and nonvolatile at room temperature and accelerates the crosslinking of curable compositions very efficiently, without impairing the storage stability of the compositions. It is particularly suitable for compositions based on polymers containing silane groups, with which it is compatible, as a result of which such compositions do not have a tendency to separation or migration or evaporation of the catalyst.

First claim

The invention claimed is:

1. An amidine of the formula (I)

wherein p is 1 and r is 0,
L is a monovalent hydrocarbyl radical having 1 to 6 carbon atoms and containing an alkoxysilane group,
Q is a glycidoxy group,
Q′ is a divalent connecting unit formed from the reaction of a reactive Q group with HZ, and
Z is an aliphatic amidine group bonded via a nitrogen atom.

2. An amidine as claimed in claim 1 , wherein Q′ is

3. An amidine as claimed in claim 1 , wherein said amidine is of formula (I′):

wherein
E 5 is an alkylene radical having 1 to 6 carbon atoms,
E 6 is an alkyl radical having 1 to 4 carbon atoms,
u is 0 or 1, and v is 2 or 3, with the proviso that (u+v) equals 3, and
Z is an aliphatic amidine group bonded via a nitrogen atom.

4. An amidine as claimed in claim 1 , wherein L is triethoxysilylpropyl or trimethoxysilylpropyl.

5. An amidine as claimed in claim 1 , wherein Z is

wherein R 1 is a hydrogen radical or an alkyl or cycloalkyl or aralkyl radical having 1 to 8 carbon atoms or together with R 2 is R 4 ,
R 2 is a hydrogen radical or an alkyl, cycloalkyl or aralkyl radical which has 1 to 18 carbon atoms and optionally contains ether oxygen or tertiary amine nitrogen, or together with R 1 is R 4 ,
R 3 is a hydrogen radical or an alkyl or cycloalkyl or aralkyl radical having 1 to 12 carbon atoms, wherein R 4 is an optionally substituted 1,2-ethylene, 1,3-propylene or 1,4-butylene radical having 2 to 12 carbon atoms,
and wherein
R 2 and R 3 together may also be an alkylene radical having 3 to 6 carbon atoms.

6. An amidine as claimed in claim 5 wherein R 1 and R 2 together are R 4 .

7. A process for preparing the amidine of the formula (I) as claimed in claim 1 , wherein at least one amidine of the formula HZ is reacted with at least one functional compound of the formula L Q] (p+r)
wherein p is 1 and r is 0,
L is a monovalent hydrocarbyl radical having 1 to 6 carbon atoms and containing an alkoxysilane group, and
Q is a glycidoxy group.

8. The process as claimed in claim 7 , wherein the amidine of the formula HZ has the formula

wherein R 3 is a hydrogen radical or an alkyl or cycloalkyl or aralkyl radical having 1 to 12 carbon atoms, and
R 4 is an optionally substituted 1,2-ethylene, 1,3-propylene or 1,4-butylene radical having 2 to 12 carbon atoms.

9. A method comprising applying as catalyst for the crosslinking of a curable composition the amidine of the formula (I) as claimed in claim 1 .

10. A method as claimed in claim 9 , wherein the curable composition is an epoxy resin composition or a polyurethane composition or an epoxy resin/polyurethane composition or a cyanate ester resin composition or a composition containing silane groups.

11. A method as claimed claim 10 , wherein the curable composition is a composition based on polymers containing silane groups selected from the group consisting of polyorganosiloxanes having terminal silane groups and organic polymers containing silane groups.

12. A method as claimed in claim 9 , wherein the curable composition is a polyurethane composition or a composition containing silane groups.

13. A curable composition comprising at least one amidine of the formula (I) as claimed in claim 1 .

14. The composition as claimed in claim 13 , wherein it further comprises at least one polymer containing silane groups.

15. The composition as claimed in claim 13 , wherein it is an adhesive or a sealant or a coating.

Assignees

• Sika Tech Ag

Inventors

• Cannas Rita
• Burckhardt Urs

Classifications

• C07D239/06 Primary

  having one double bond between ring members or between a ring member and a non-ring member · CPC title

• C09J183/06

  containing silicon bound to oxygen-containing groups (C09J183/12 takes precedence) · CPC title

• C09D183/06

  containing silicon bound to oxygen-containing groups (C09D183/12 takes precedence) · CPC title

• C08F2/50

  with sensitising agents · CPC title

• C08G77/38

  Polysiloxanes modified by chemical after-treatment · CPC title