Moisture-curable polyurethane composition with reduced surface tackiness

Patent metadata

Field	Value
Publication number	US-12344701-B2
Application number	US-202017631938-A
Country	US
Kind code	B2
Filing date	May 26, 2020
Priority date	Aug 15, 2019
Publication date	Jul 1, 2025
Grant date	Jul 1, 2025

Abstract

A moisture-curable composition, including: a) at least one polyurethane polymer P having isocyanate groups; b) at least one blocked polyamine BA having blocked, hydrolytically activatable amino groups; and c) at least one monoamine MA of formula (V),

where R a represents a linear, cyclic, or branched alkyl or alkenyl radical or optionally substituted aryl radical with 1 to 12 C atoms and optionally including ether oxygen atoms; R b and R c either independently represent a rest R a or a hydrogen atom, where at least one of R b and R c is a hydrogen atom, or R b and R c together with the N atom of monoamine MA form an aldimine group that under influence of water hydrolyzes to a aldehyde and an amine R a —NH 2 ; wherein polymer P is the reaction product of 2,4- and/or 2,6-toluylene diisocyanate (TDI) and at least one polyol, wherein the polyol has an average functionality of >2.

First claim

The invention claimed is:

1. A moisture-curable composition comprising
a) at least one polyurethane polymer P having isocyanate groups;
b) at least one blocked polyamine BA having blocked, hydrolytically activatable amino groups; and
c) at least one monoamine MA of formula (V),

where
R a represents a linear, cyclic, or branched alkyl or alkenyl radical or optionally substituted aryl radical with 1 to 12 C atoms and optionally comprising ether oxygen atoms;
R b and R c either independently represent a rest R a or a hydrogen atom, with the provisio that at least one of R b and R c is a hydrogen atom, or R b and R c together with the N atom of monoamine MA form an aldimine group that under influence of water hydrolyzes to a aldehyde and an amine R a —NH 2 ;
wherein polymer P is the reaction product of 2,4- and/or 2,6-toluylene diisocyanate (TDI) and at least one polyol, wherein the polyol has an average functionality of >2; and
wherein the amount of said monoamine MA in the composition is between 0.2 and 25 weight parts per 100 weight parts of said polymer P.

2. The moisture-curable composition according to claim 1 , wherein R b and R c independently represent a rest R a or a hydrogen atom, with the provisio that at least one of R b and R c is a hydrogen atom.

3. The moisture-curable composition according to claim 2 , wherein R b is a rest R a and R c is a hydrogen atom.

4. The moisture-curable composition according to claim 1 , wherein R b and R c together with the N atom of monoamine MA form an aldimine group that under influence of water hydrolyzes to a aldehyde and an amine R a —NH 2 .

5. The moisture-curable composition according to claim 1 , wherein the blocked polyamine BA and the polymer P having isocyanate groups are present in the curable composition in such an amount that the ratio between the blocked amino groups and the isocyanate groups is from 0.1 to 1.1.

6. The moisture-curable composition according to claim 1 , wherein the blocked polyamine BA is an aldimine of the formula (I),

where
A is the rest of an amine after removal of n primary amino groups and m HX groups;
n is 2 or 3 or 4;
m is 0 or 1 or 2, with the provisio that m+n is 2 or 3 or 4;
R 1 and R 2 are either each independently a monovalent hydrocarbon radical with 1 to 12 C atoms, or together form a divalent hydrocarbon radical with 4 to 12 C atoms that is part of an optionally substituted carbocyclic ring with 5 to 8 C atoms;
R 3 is a hydrogen atom or an alkyl-, cycloalkyl-, arylalkyl-, or alkoxycarbonyl radical with 1 to 12 C atoms;
R 4 is a hydrogen atom or a monovalent radical with 1 to 20 C atoms selected from alkyl-, cycloalkyl-, arylalkyl-, aryl-, —OR 5 ′, —SR 5 ′, and
—NR 5 ′R 5 ″, wherein R 5 ′ and R 5 ″ either each independently are hydrocarbon radicals or together form an alkylene radical that is part of a 5-, 6-, or 7-membered ring; and
X is O or S or NR 6 , wherein R 6 is a hydrocarbon radical with 1 to 20 C atoms which is optionally substituted with a carbonic acid ester-, nitrile-, nitro-, phosphonic acid ester-, sulphone-, or sulphonic acid ester-group.

7. The moisture-curable composition according to claim 6 , wherein R 1 and R 2 are each methyl and/or R 3 is a hydrogen atom and/or R 4 is a linear alkyl radical having 11 to 20 C atoms.

8. The curable composition according to claim 6 , wherein m is 0 and n is 2 or 3.

9. The moisture-curable composition according to claim 1 , wherein the blocked polyamine BA is a polymeric blocked polyamine PBA that is a polymer having at least two blocked, hydrolytically activatable amino groups.

10. The moisture-curable composition according to claim 1 , wherein the polyol used for the synthesis of polymer P has an average OH-functionality of between 2.1 and 3.5 and/or said polymer P is prepared from said polyol and TDI using a molar ratio of NCO groups to OH groups of between 1.8 and 2.2.

11. The moisture-curable composition according to claim 1 , wherein the composition comprises:
between 10 and 40 wt.-% based on the composition, of said polyurethane polymer P having isocyanate groups;
between 1 and 5 wt.-% based on the composition, of said blocked polyamine BA having blocked, hydrolytically activatable amino groups;
between 5 and 40 wt.-% based on the composition, of at least one plasticizer;
between 0 and 40 wt.-% based on the composition, of at least one thixotropy additive;
between 0.05 and 2 wt.-% based on the composition, of said monoamine MA;
between 0 and 60 wt.-% based on the composition, of at least one filler; and
between 0 and 5 wt.-% based on the composition, of at least one further additive selected from the group consisting of adhesion promoters, drying agents, catalysts, and stabilizers.

12. A process for sealing a joint between a substrate S1 and a substrate S2, comprising the steps of:
i) applying a moisture-curable composition according to claim 1 into a gap between substrate S1 and substrate S2 such that the composition is in contact with both substrates S1 and S2;
and, subsequently,

ii) let the applied composition cure by means of humidity;
wherein the substrate S2 is formed of the same or a different material than the substrate S1.

13. A method comprising: applying the moisture-curable composition according to claim 1 to a surface of a substrate and curing the composition to form a structure in which the cured composition is configured as a joint sealant.

14. A method comprising: introducing a monoamine MA of formula (V),

into a moisture-curable composition comprising at least one polyurethane polymer P having isocyanate groups and at least one blocked polyamine BA having blocked, hydrolytically activatable amino groups, to form a mixture, the monoamine MA of formula (V) being present in the mixture in an amount effective to reduce the surface tackiness and/or the elastic modulus of a cured form of the mixture, and curing the mixture to form a cured product with reduced surface tackiness and/or elastic modulus relative to a corresponding cured product prepared in an identical manner but without the monoamine MA of formula (V),
where
R a represents a linear, cyclic, or branched alkyl or alkenyl radical or optionally substituted aryl radical with 1 to 12 C atoms and optionally comprising ether oxygen atoms;
R b and R c either independently represent a rest R a or a hydrogen atom, with the provisio that at least one of R b and R c is a hydrogen atom, or R b and R c together with the N atom of monoamine MA form an aldimine group that under influence of water hydrolyzes to a aldehyde and an amine R a —NH 2 ;

wherein
said polymer P is the reaction product of 2,4- and/or 2,6-toluylene diisocyanate (TDI) and at least one polyol, wherein the polyol has an average functionality of >2; and
wherein the amount of said monoamine MA in the composition is between 0.2 and 25 weight parts per 100 weight parts of said polymer P.

15. The method according to claim 14 , wherein R b and R c independently represent a rest R a or a hydrogen atom, with the provisio that at least one of R b and R c is a hydrogen atom.

16. A process for sealing a joint between a substrate S1 and a substrate S2, comprising the steps of:
i) applying a moisture-curable

Assignees

• Sika Tech Ag

Inventors

• Song Zhiyong
• Schlumpf Michael

Classifications

• C08L75/08

  from polyethers · CPC title

• C08G2190/00

  Compositions for sealing or packing joints · CPC title

• C08G18/4841

  containing oxyethylene end groups · CPC title

• C08G18/4829

  Polyethers containing at least three hydroxy groups (C08G18/4833 - C08G18/5096 take precedence) · CPC title

• C08G18/3819

  having nitrogen · CPC title