Polyurethane resin for moisture-permeable water-proof materials, and polyurethane resin composition

Patent metadata

Field	Value
Publication number	US-9499655-B2
Application number	US-201514935707-A
Country	US
Kind code	B2
Filing date	Nov 9, 2015
Priority date	Jul 8, 2011
Publication date	Nov 22, 2016
Grant date	Nov 22, 2016

Abstract

The present invention aims to provide a polyurethane resin for moisture-permeable waterproof materials which is excellent in all of the moisture permeability, waterproofness, and resistance to washing. The polyurethane resin for moisture-permeable waterproof materials according to the present invention is a polyurethane resin for moisture-permeable waterproof materials, obtainable by reacting an active hydrogen component (A1) with an organic polyisocyanate component (B),
wherein the active hydrogen component (A1) includes an oxyethylene group-containing high molecular weight diol (a1), and a compound (S1) containing at least one active hydrogen atom and being represented by the following formula (1):

wherein X 1 represents a residue produced by removing c piece (s) of active hydrogen atom(s) from an active hydrogen-containing compound having a valence of m, the c representing an integer satisfying the inequality: 1≦c≦m, the m representing an integer of 1 to 20;
X 2 represents a residue produced by removing one piece of active hydrogen atom from an active hydrogen-containing compound, and a plurality of X 2 s may be the same as or different from one another; X 1 and X 2 may be the same as or different from each other; Y represents a residue produced by removing all of carboxyl groups from an aromatic polycarboxylic acid having a valence of 3 or more, wherein an aromatic ring in Y consists of carbon atoms, the carbon atoms are each optionally bound to a halogen atom and/or a substituent other than a carboxyl group, and at least one of the carbon atoms has no substituent; a represents an integer of not smaller than 1;
b represents an integer of not smaller than 0; and a and b satisfy the inequality: 2≦a+b≦d−2, wherein d represents the number of hydrogen atoms bound to the carbon atoms forming the aromatic ring of the aromatic polycarboxylic acid when all of substituents including a carboxyl group in the aromatic polycarboxylic acid are substituted by hydrogen atoms, i.e., the number of substitutable sites on the aromatic ring.

First claim

The invention claimed is:

1. A polyurethane resin (U) for moisture-permeable waterproof materials, obtained by reacting an active hydrogen component (A1) with an organic polyisocyanate component (B),
wherein the active hydrogen component (A1) comprises
an oxyethylene group-containing high molecular weight diol (a1), and
a compound (S1) containing at least one active hydrogen atom of the following formula (1):

wherein X 1 represents a residue produced by removing c piece(s) of active hydrogen atom(s) from an active hydrogen-containing compound having a valence of m selected from the group consisting of C 2 -C 20 polyhydric alcohols, polyether polyols obtained by adding alkylene oxide to C 2 -C 20 polyhydric alcohols, C 2 -C 20 aliphatic polyamines, and polyvalent thiol compounds, the c represents an integer satisfying the inequality: 1≦c≦m, and the m represents an integer of 2 to 20;
X 2 represents a residue produced by removing one piece of active hydrogen atom from an active hydrogen-containing compound selected from the group consisting of C 2 -C 20 polyhydric alcohols, polyether polyols obtained by adding alkylene oxide to C 2 -C 20 polyhydric alcohols, C 2 -C 20 aliphatic polyamines, and polyvalent thiol compounds, and a plurality of X 2 s may be the same as or different from one another;
X 1 and X 2 may be the same as or different from each other;
Y represents a residue produced by removing all of carboxyl groups from an aromatic polycarboxylic acid having a valence of 3 or more, wherein an aromatic ring in Y consists of carbon atoms, the carbon atoms are each optionally bound to a halogen atom and/or a substituent other than a carboxyl group, and at least one of the carbon atoms has no substituent;
a represents an integer of not smaller than 1;
b represents an integer of not smaller than 0; and

a and b satisfy the inequality: 2≦a+b≦d−2, wherein d represents the number of hydrogen atoms bound to the carbon atoms forming the aromatic ring of the aromatic polycarboxylic acid when all of substituents including a carboxyl group in the aromatic polycarboxylic acid are substituted by hydrogen atoms.

2. The polyurethane resin for moisture-permeable waterproof materials according to claim 1 ,
wherein the compound (S1) has a hydroxyl value of 70 to 500 mg KOH/g.

3. The polyurethane resin for moisture-permeable waterproof materials according to claim 1 ,
wherein the compound (S1) includes the residue Y at a concentration of 1.0 to 6.0 mmol/g.

4. The polyurethane resin for moisture-permeable waterproof materials according to claim 1 ,
wherein the compound (S1) has a carbonyl group concentration of 3.0 to 20 mmol/g.

5. The polyurethane resin for moisture-permeable waterproof materials according to claim 1 ,
wherein the aromatic polycarboxylic acid having a valence of 3 or more has a structure in which two carbon atoms adjacent to the carbon atom having no substituent in the aromatic ring are each bound to a carboxyl group.

6. The polyurethane resin for moisture-permeable waterproof materials according to claim 5 ,
wherein a carboxyl group or groups is/are further bound to either one or both of carbon atoms that are adjacent to the carbon atoms each bound to a carboxyl group.

7. The polyurethane resin for moisture-permeable waterproof materials according to claim 1 ,
wherein the aromatic polycarboxylic acid having a valence of 3 or more is at least one of trimellitic acid or pyromellitic acid.

8. The polyurethane resin for moisture-permeable waterproof materials according to claim 1 ,
wherein the active hydrogen component (A1) further contains a chain extender (a3) and a reaction terminator (a4).

9. The polyurethane resin for moisture-permeable waterproof materials according to claim 1 ,
wherein an amount of the compound (S1) based on the weight of the polyurethane resin is 0.01 to 10% by weight.

10. The polyurethane resin for moisture-permeable waterproof materials according to claim 1 ,
wherein an amount of the oxyethylene group in the polyurethane resin based on the weight of the polyurethane resin is 20 to 80% by weight.

Assignees

• Sanyo Chemical Ind Ltd

Inventors

• Nagatani Yoshihiro
• Yokoi Tomomi

Classifications

• C08G18/282

  Alkanols, cycloalkanols or arylalkanols including terpenealcohols · CPC title

• C08G18/4804 Primary

  Two or more polyethers of different physical or chemical nature · CPC title

• C08G18/4018

  Mixtures of compounds of group C08G18/42 with compounds of group C08G18/48 · CPC title

• D06M15/564

  Polyureas, polyurethanes or other polymers having ureide or urethane links; Precondensation products forming them · CPC title

• C08L75/08

  from polyethers · CPC title