Amidine catalyst for curable compositions

Patent metadata

Field	Value
Publication number	US-10995074-B2
Application number	US-201716463579-A
Country	US
Kind code	B2
Filing date	Dec 12, 2017
Priority date	Dec 21, 2016
Publication date	May 4, 2021
Grant date	May 4, 2021

Abstract

An amidine containing at least one structural unit of the formula (I) and the use thereof as catalyst for the crosslinking of a functional compound, especially of a polymer having silane groups. The amidine is preparable in a simple process from readily available starting materials, is largely odorless at room temperature and is of low toxicity. It accelerates the crosslinking of functional compounds surprisingly efficiently and can be adjusted for optimal compatibility with different compositions via the radical to which the structural units of the formula (I) is bonded, which means that such compositions do not have a tendency to migration-related defects such as separation, exudation or substrate soiling.

First claim

The invention claimed is:

1. An amidine containing at least one structural unit of the formula (I)

where
R 1 is a hydrogen radical or an alkyl, cycloalkyl or aralkyl radical optionally having unsaturated moieties, having 1 to 30 carbon atoms and optionally having a tertiary amino group,
R 2 is an optionally alkyl-substituted 1,2-ethylene or 1,3-propylene radical,
R 3 is an optionally alkyl-substituted 1,3-propylene or 1,4-butylene radical, and
X is O or NR 4 where R 4 is a hydrogen radical or is an alkyl, cycloalkyl or aralkyl radical having 1 to 8 carbon atoms.

2. The amidine as claimed in claim 1 , wherein R 1 is selected from the group consisting of methyl, ethyl, propyl, butyl, cyclohexyl, 2-ethylhexyl, n-decyl, lauryl, cocoalkyl, oleyl, soyaalkyl, tallowalkyl and 3-(N,N-dimethylamino)propyl.

3. The amidine as claimed in claim 1 , wherein X is NR 4 .

4. The amidine as claimed in claim 1 , wherein the amidine has the formula (II)

where
n is 1 or 2 or 3, and
A is an n-valent radical which has a molecular weight in the range from 28 to 5,000 g/mol and is bonded via carbon atoms.

5. The amidine as claimed in claim 4 , wherein A is a monovalent hydrocarbyl radical which has 1 to 30 carbon atoms and optionally contains ether oxygen or tertiary amine nitrogen or siloxane units.

6. The amidine as claimed in claim 4 , wherein A is a di- or trivalent hydrocarbyl radical which has 2 to 50 carbon atoms and optionally contains ether oxygen or tertiary amine nitrogen or siloxane units.

7. A process for preparing the amidine of the formula (II) as claimed in claim 4 , wherein at least one amine of the formula (III) is reacted with a compound of the formula (IV) with removal of water

8. The process as claimed in claim 7 , wherein a compound of the formula (IV) with X═NR 4 is used, which has been obtained beforehand by reacting at least one amine of the formula A-(NHR 4 ) n with a compound of the formula (IV) with X═O with removal of the corresponding alcohol.

9. A method comprising applying the amidine as claimed in claim 1 as catalyst for the crosslinking of a functional compound.

10. The method as claimed in claim 9 , wherein the functional compound is a silane, a polymer having silane groups, a polyisocyanate or a polyurethane polymer having isocyanate groups.

11. A curable composition comprising at least one amidine as claimed in claim 1 .

12. The curable composition as claimed in claim 11 , further comprising at least one functional compound having at least one silane group and/or isocyanate groups.

13. The curable composition as claimed in claim 11 , further comprising at least one polymer having silane groups.

14. The curable composition as claimed in claim 11 , wherein the curable composition is an adhesive or a sealant or a coating.

15. A cured composition obtained from the curable composition as claimed in claim 11 .

Assignees

• Sika Tech Ag

Inventors

• Cannas Rita
• Burckhardt Urs

Classifications

• C09J183/12

  containing polyether sequences · CPC title

• C09D183/12

  containing polyether sequences · CPC title

• C08G77/46

  containing polyether sequences · CPC title

• C07D239/06 Primary

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

• B01J31/0244

  with nitrogen contained as ring member in aromatic compounds or moieties, e.g. pyridine · CPC title