Polyaldimine and curable polyurethane composition

Patent metadata

Field	Value
Publication number	US-10647807-B2
Application number	US-201615773972-A
Country	US
Kind code	B2
Filing date	Dec 20, 2016
Priority date	Dec 21, 2015
Publication date	May 12, 2020
Grant date	May 12, 2020

Abstract

A polyaldimine of the formula (I) with advantageous properties in use as latent hardener for compositions including isocyanate groups, and compositions containing the polyaldimine of the formula (I) and at least one polyisocyanate and/or at least one polyurethane polymer containing isocyanate groups. The polyaldimine of the formula (I) is odourless, pH-neutral, liquid at room temperature, has low viscosity, has little sensitivity to heat and moisture, and is stable in storage together with isocyanates. It can provide odourless single-component polyurethane compositions which have good stability in storage and which do not produce bubbles when hardened in the presence of moisture, and which cause no problematic odour emissions, giving a hardened elastic material with good mechanical properties and surprisingly little tendency towards plasticizer migration.

First claim

The invention claimed is:

1. A polyaldimine of the formula (I)

where
n is 2 or 3,
Z is an aryl radical substituted by an alkyl and/or alkoxy group and having a total of 12 to 26 carbon atoms, and
A is an n-valent aliphatic or cycloaliphatic hydrocarbyl radical optionally containing ether oxygen and having a molecular weight in the range from 42 to 6′000 g/mol, bonded via at least one tertiary or quaternary carbon atom and/or containing a bi- or tricyclic ring system.

2. A polyaldimine as claimed in claim 1 , wherein Z is a radical of the formula (II)

where R is a linear or branched alkyl radical having 10 to 14 carbon atoms.

3. A polyaldimine as claimed in claim 2 , wherein R is branched.

4. A polyaldimine as claimed in claim 3 , wherein R is a radical of the formula

where R 1 and R 2 are each an alkyl radical and together have 9 to 13 carbon atoms.

5. A polyaldimine as claimed in claim 1 , wherein A is selected from the group consisting of 1,2-propylene, 1,3-pentylene, 2-methyl-1,5-pentylene, 2,2(4),4-trimethyl-1,6-hexamethylene, 1,2-cyclohexylene, (1,5,5-trimethylcyclohexan-1-yl)methane-1,3, 4(2)-methyl-1,3-cyclohexylene, methylenedicyclohexan-4-yl, methylenebis(2-methylcyclohexan-4-yl), (bicyclo[2.2.1]heptan-2,5(2,6)-diyl)dimethylene, (tricyclo[5.2.1.0 2,6 ]decane-3(4),8(9)-diyl)dimethylene, α,ω-polyoxypropylene having an average molecular weight in the range from 170 to 5′000 g/mol and trimethylolpropane- or glycerol-started tris(ω-polyoxypropylene) having an average molecular weight in the range from 330 to 6′000 g/mol.

6. A reaction product containing at least one polyaldimine as claimed in claim 1 , obtained from the reaction of at least one amine of the formula (III) with at least one aldehyde of the formula (IV) in a condensation reaction with release of water, wherein the aldehyde was present stoichiometrically or in a stoichiometric excess in relation to the primary amino groups

7. A mixture of polyaldimines as claimed in claim 1 , in which each Z is a radical of the formula (II) and R is selected from linear or particularly branched decyl, undecyl, dodecyl, tridecyl and tetradecyl radicals.

8. A method comprising latently hardening compositions containing isocyanate groups with at least one polyaldimine as claimed in claim 1 .

9. The method as claimed in claim 8 , wherein some or all of the isocyanate groups are derived from 4,4′- or 2,4′- or 2,2′-diphenylmethane diisocyanate or any mixtures of these isomers.

10. A composition comprising
at least one polyaldimine as claimed in claim 1 and
at least one polyisocyanate and/or at least one polyurethane polymer containing isocyanate groups.

11. The composition as claimed in claim 10 , wherein it comprises at least one polyurethane polymer containing isocyanate groups.

12. The composition as claimed in claim 11 , wherein some or all of the isocyanate groups are derived from 4,4′- or 2,4′- or 2,2′-diphenylmethane diisocyanate or any mixtures of these isomers.

13. The composition as claimed in claim 10 , wherein it additionally comprises at least one further constituent selected from catalysts, fillers, plasticizers and solvents.

14. The composition as claimed in claim 10 , wherein it is a one-component composition.

15. The composition as claimed in claim 10 , wherein it is an adhesive or a sealant or a coating.

Assignees

• Sika Tech Ag

Inventors

• Burckhardt Urs
• Kramer Andreas

Classifications

• C08G18/12

  using two or more compounds having active hydrogen in the first polymerisation step · CPC title

• C08G18/4812

  Mixtures of polyetherdiols with polyetherpolyols having at least three hydroxy groups · CPC title

• C08G18/10

  Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step · CPC title

• C08G18/3256 Primary

  Reaction products of polyamines with aldehydes or ketones · CPC title

• C08G18/7671

  containing only one alkylene bisphenyl group · CPC title