Rapid-curing, migration-free composition based on organic polymers containing silane groups

Patent metadata

Field	Value
Publication number	US-10100069-B2
Application number	US-201515302257-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

The invention relates to a composition comprising at least one organic polymer that contains silane groups and at least one catalyst of formula (I). The composition is low in emissions and low-odor, has a good shelf-life, cures rapidly to form a mechanically high-quality, durable material with a very low propensity for migration-related defects such as exudation or dirt retention by the substrate. The composition is particularly suitable for use as an adhesive, sealant or coating.

First claim

The invention claimed is:

1. A process for producing a composition comprising
at least one organic polymer containing silane groups; and
at least one catalyst of the formula (I),

wherein
A is an aliphatic or cycloaliphatic or arylaliphatic hydrocarbyl radical which has 1 to 100 carbon atoms, optionally contains unsaturated moieties, optionally contains heteroatoms and optionally has amino groups or hydroxyl groups, or together with R 1 is a divalent, optionally branched alkylene radical which has 4 to 12 carbon atoms and optionally contains a heteroatom,
R 1 is hydrogen or an alkyl or cycloalkyl or aralkyl radical having 1 to 8 carbon atoms, or together with A is a divalent, optionally branched alkylene radical which has 4 to 12 carbon atoms and optionally contains a heteroatom, and
R 2 and R 5 are each independently an alkyl, cycloalkyl or aralkyl radical which has 1 to 18 carbon atoms and optionally contains heteroatoms, wherein A is a different radical from each of R 2 and R 5 ;
wherein the catalyst of the formula (I) does not contain any nitrogen atom bonded directly to an aromatic ring or part of a heteroaromatic ring system, and the catalyst of the formula (I) is free of silane groups, and
wherein the composition is free of carbodiimide,

the process comprising
preparing a catalyst of the formula (I), wherein at least one amine of the formula (II) is reacted with at least one carbodiimide of the formula (III),

adding the prepared catalyst to the at least one organic polymer containing silane groups or to a composition comprising the at least one organic polymer containing silane groups, wherein the adding is effected by preparing the catalyst in the presence of the at least one organic polymer containing silane groups.

2. The process as claimed in claim 1 , wherein A is selected from the group consisting of n-hexyl, n-octyl, 2-ethylhexyl, n-decyl, lauryl, cyclohexyl, benzyl, 2-methoxyethyl, 3-methoxypropyl, polyoxyalkylene radical having oxyethylene and 1,2-oxypropylene units and a molecular weight in the range from about 180 to 600 g/mol, N-methyl-3-aminopropyl, N-(2-ethylhexyl)-3-aminopropyl, N-cyclohexyl-3-aminopropyl, 3-(N,N-dimethylamino)propyl, 2-aminopropyl, 3-aminopropyl, 3-aminopentyl, 5-amino-4-methylpentyl, 5-amino-2-methylpentyl, 6-aminohexyl, 6-amino-3,3(5),5-trimethylhexyl, 6-amino-2,2(4),4-trimethylhexyl, 8-aminooctyl, 10-aminodecyl, 12-aminododecyl, 3-aminomethyl-3,5,5-trimethylcyclohexyl, 3-amino-1,5,5-trimethylcyclo-hexylmethyl, 3-aminomethylcyclohexylmethyl, 4-aminomethylcyclohexyl-methyl, 3-aminomethylbenzyl, 5-amino-3-oxapentyl, ω-2-aminopropyl-polyoxypropylene radical having a molecular weight in the range from about 200 to 500 g/mol, 2-hydroxypropyl, 3-hydroxypropyl, 1,1-dimethyl-2-hydroxyethyl, and 5-hydroxy-3-oxapentyl.

3. The process as claimed in claim 1 , wherein R 1 is hydrogen.

4. The process as claimed in claim 1 , wherein R 2 and R 5 are each independently ethyl, isopropyl, tert-butyl, 3-(dimethylamino)propyl or cyclohexyl.

5. The process as claimed in claim 1 , wherein the organic polymer containing silane groups is a polyolefin containing silane groups or a polyester containing silane groups or a poly(meth)acrylate containing silane groups or a polyether containing silane groups or a mixed form of these polymers.

6. The process as claimed in claim 1 , wherein at least one organotitanate is additionally present.

7. The process as claimed in claim 1 , wherein the amine of the formula (II) is selected from the group consisting of n-hexylamine, n-octylamine, 2-ethylhexylamine, n-decylamine, laurylamine, cyclohexyl-amine, benzylamine, 2-methoxyethylamine, 3-methoxypropylamine, polyoxyalkyleneamine having oxyethylene and 1,2-oxypropylene units and a mean molecular weight in the range from 180 to 600 g/mol, N-methyl-1,3-propanediamine, N-(2-ethylhexyl)-1,3-propanediamine, N-cyclohexyl-1,3-propanediamine, N,N-dimethyl-1,3-propanediamine, 1,2-propanediamine, 1,3-propanediamine, 1,3-pentanediamine, 1,5-diamino-2-methylpentane, 1,6-hexanediamine, 2,2,4- and 2,4,4-trimethylhexa-methylenediamine, 1,8-octanediamine, 1,10-decanediamine, 1,12-dodecanediamine, 1-amino-3-aminomethyl-3,5,5-trimethylcyclohexane, 1,3-bis(aminomethyl)cyclohexane, 1,4-bis(aminomethyl)cyclohexane, 1,3-bis(aminomethyl)benzene, bis(2-aminoethyl) ether, polyoxypropylene-diamine having a mean molecular weight in the range from about 220 to 500 g/mol, 1-amino-2-propanol, 3-amino-1-propanol, 2-amino-2-methyl-1-propanol, and 2-(2-aminoethoxy)ethanol.

8. The process as claimed in claim 1 , wherein the carbodiimide of the formula (III) is selected from the group consisting of N,N′-diisopropylcarbodiimide, N,N′-di-tert-butylcarbodiimide, N,N′-dicyclohexylcarbodiimide and N-ethyl-N′-(3-dimethylaminopropyl)-carbodiimide.

9. A method for adhesively bonding, sealing, or coating a substrate, including the step of applying the composition produced in the process of claim 1 as an adhesive, sealant or coating to the substrate and exposing the composition to water.

10. A cured composition obtained from the composition produced in the process of claim 1 after it has been cured with water.

11. A method for catalytic crosslinking an organic polymer containing silane groups comprised in the composition produced in the process of claim 1 , including exposing the composition to water.

12. A catalyst comprised of 1-(3-(N,N-dimethylamino)propyl)-2,3-dicyclohexylguanidine.

Assignees

• Sika Tech Ag

Inventors

• Burckhardt Urs
• Cannas Rita

Classifications

• C09D183/08

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

• C08G65/002

  from unsaturated compounds (unsaturated oxiranes C08G65/14) · CPC title

• C07C279/04 Primary

  having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton · CPC title

• C07C279/16

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

• C07C279/18

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