Crystalline polyesterpolyol

Patent metadata

Field	Value
Publication number	US-12486356-B2
Application number	US-202117449314-A
Country	US
Kind code	B2
Filing date	Sep 29, 2021
Priority date	Apr 3, 2019
Publication date	Dec 2, 2025
Grant date	Dec 2, 2025

Abstract

The present invention refers to a polyesterpolyol which is obtained by reaction of at least one diol with at least one primary hydroxy group and at least one secondary hydroxy group with a saturated aliphatic dicarboxylic acid comprising a carbon chain of at least 12 carbon atoms. The invention further relates to an adhesive composition containing the polyesterpolyol, in particular a polyurethane adhesive composition.

First claim

The invention claimed is:

1 . A crystalline polyesterpolyol that is the reaction product of a reaction mixture comprising:
a) a diol selected from the group consisting of 1,2-propane diol, 1,3-butane diol, and 1,4-pentane diol; b) a saturated aliphatic dicarboxylic acid having a carbon chain of 12 carbon atoms or 14 carbon atoms, wherein the carbon chain is terminated at each end with a carboxylic acid group; and c) at least one other diol and/or at least one additional dicarboxylic acid, wherein the crystalline polyesterpolyol is liquid at ambient temperature and exhibits defined polymorphic crystallization peaks below 50° C., determined by DSC with a heating rate of 10K/min.

2 . The crystalline polyesterpolyol of claim 1 , wherein the carbon chain has 12 carbon atoms.

3 . The crystalline polyesterpolyol of claim 1 , wherein the saturated aliphatic dicarboxylic acid is selected from the group consisting of 1,12-dodecanedioic acid and 1,14-tetradecanedioic acid.

4 . The crystalline polyesterpolyol of claim 1 , wherein the at least one other diol is selected from the group consisting of 1,3-propane diol, diethylene glycol, NPG, ethylene glycol, 1,4-butane diol, 1,6-hexane diol, and any mixture thereof.

5 . The crystalline polyesterpolyol of claim 1 , wherein the crystalline polyesterpolyol has a hydroxyl value (OH value) of from 5 to 150 mg KOH/g, determined according to DIN 53240.

6 . The crystalline polyesterpolyol of claim 1 , wherein the at least one additional dicarboxylic acid is selected from the group consisting of succinic acid, adipic acid, sebacic acid, azelaic acid, isophthalic acid, orthophthalic acid, terephthalic acid, furan dicarboxylic acid, itaconic acid, and anhydrides, chlorides and esters thereof.

7 . The crystalline polyesterpolyol of claim 1 , wherein the diol and the saturated aliphatic dicarboxylic acid are present in the reaction mixture in a molar ratio of from 1.5:1 to 1:1.

8 . An adhesive composition comprising the crystalline polyesterpolyol of claim 1 .

9 . The adhesive composition of claim 8 , wherein the adhesive composition is liquid at a temperature of 25° C.

10 . The adhesive composition of claim 8 , wherein the adhesive composition is a curable polyurethane adhesive.

11 . The adhesive composition of claim 8 , wherein the adhesive composition is a two-component, curable polyurethane adhesive that is liquid at ambient temperature.

12 . The crystalline polyesterpolyol of claim 1 , wherein the diol is selected from the group consisting of 1,2-propane diol and 1,4-pentane diol.

13 . The crystalline polyesterpolyol of claim 5 , wherein the crystalline polyesterpolyol has a hydroxyl value (OH value) of from 10 to 100 mg KOH/g, determined according to DIN 53240.

14 . The crystalline polyesterpolyol of claim 7 , wherein the diol and the saturated aliphatic dicarboxylic acid are present in the reaction mixture in a molar ratio of from 1.2:1 to 1:1.

15 . A crystalline polyesterpolyol that is the reaction product of a reaction mixture comprising:
a) a diol selected from the group consisting of 1,2-propane diol, 1,3-butane diol, and 1,4-pentane diol; and b) a saturated aliphatic dicarboxylic acid selected from the group consisting of 1,16-hexaadecanedioic acid and 1,18-octadecanedioic acid, wherein the crystalline polyesterpolyol is liquid at ambient temperature and exhibits defined polymorphic crystallization peaks below 50° C., determined by DSC with a heating rate of 10K/min.

16 . The crystalline polyesterpolyol of claim 15 , wherein the reaction mixture further comprises at least one additional compound selected from the group consisting of succinic acid, adipic acid, sebacic acid, azelaic acid, isophthalic acid, orthophthalic acid, terephthalic acid, furan dicarboxylic acid, itaconic acid, and anhydrides, chlorides and esters thereof.

17 . A crystalline polyesterpolyol that is the reaction product of a reaction mixture comprising:
a) a diol selected from the group consisting of 1,3-butane diol and 1,4-pentane diol; and b) a saturated aliphatic dicarboxylic acid having a carbon chain of 12 carbon atoms or 14 carbon atoms, wherein the carbon chain is terminated at each end with a carboxylic acid group, wherein the crystalline polyesterpolyol is liquid at ambient temperature and exhibits defined polymorphic crystallization peaks below 50° C., determined by DSC with a heating rate of 10K/min.

18 . The crystalline polyesterpolyol of claim 17 , wherein the reaction mixture further comprises at least one additional compound selected from the group consisting of succinic acid, adipic acid, sebacic acid, azelaic acid, isophthalic acid, orthophthalic acid, terephthalic acid, furan dicarboxylic acid, itaconic acid, and anhydrides, chlorides and esters thereof.

Assignees

• Henkel Ag & Co Kgaa

Inventors

• Brandt Adrian
• Beck Horst
• Kux Alexander
• Stadler Bernhard M
• De Vries Johannes Gerardus

Classifications

• C09J175/06

  from polyesters · CPC title

• C09J167/03

  the dicarboxylic acids and dihydroxy compounds having the carboxyl - and the hydroxy groups directly linked to aromatic rings · CPC title

• C08G2250/00

  Compositions for preparing crystalline polymers · CPC title

• C08G2170/00

  Compositions for adhesives · CPC title

• C09J167/02

  Polyesters derived from dicarboxylic acids and dihydroxy compounds (C09J167/06 takes precedence) · CPC title