Crystalline Polyesterpolyol

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.

Claims

1. A crystalline polyesterpolyol that is the reaction product of a reaction mixture comprising: a) at least one diol with at least one primary hydroxy group and at least one secondary hydroxy group; and b) at least one saturated aliphatic dicarboxylic acid having a carbon chain of at least 12 carbon atoms.

2. The crystalline polyesterpolyol according to claim 1 wherein the at least one diol is selected from the group consisting of 1,2-propane diol, 1,3-butane diol, 1,4-pentane diol, 1,5-hexane diol, 1,6-heptane diol and 1,7-octane diol.

3. The crystalline polyesterpolyol according to claim 1 wherein the at least one dicarboxylic acid comprises a carbon chain of 12 to 24 carbon atoms.

4. The crystalline polyesterpolyol according to claim 1 wherein the at least one dicarboxylic acid is selected from the group consisting of 1,12-dodecanedioic acid, 1,14-tetradecanedioic acid, 1,16-hexadecanedioicacid and 1,18-octadecanedioic acid as well as anhydrides, esters and chlorides derived from any of said acids.

5. The crystalline polyesterpolyol according to claim 1 wherein the polyesterpolyol has melting point of −30 to 50° C., determined by DSC with a heating rate of 10K/min.

6. The crystalline polyesterpolyol according to claim 1 wherein the polyesterpolyol has melting point of −30 to 50° C. and defined melting and crystallization peaks, determined by DSC with a heating rate of 10K/min.

7. The crystalline polyesterpolyol according to claim 1 wherein the polyesterpolyol is liquid at ambient temperature and has defined melting and crystallization peaks, determined by DSC with a heating rate of 10K/min.

8. The crystalline polyesterpolyol according to claim 1 wherein the polyesterpolyol is liquid at ambient temperature and has defined melting and crystallization peaks below 50° C., determined by DSC with a heating rate of 10K/min.

9. The crystalline polyesterpolyol according to claim 1 wherein the polyesterpolyol has melting point of −30 to 50° C. and defined polymorphic crystallization peaks below 50° C., determined by DSC with a heating rate of 10K/min.

10. The crystalline polyesterpolyol according to claim 1 wherein the reaction mixture comprises additional diols.

11. The crystalline polyesterpolyol according to claim 1 wherein the reaction mixture comprises additional diols selected from the group consisting of 1,3-propane diol, diethylene glycol, NPG, ethylene glycol, 1,4-butane diol, 1,6-hexane diol and mixtures thereof.

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

13. The crystalline polyesterpolyol according to claim 1 wherein the reaction mixture further comprises additional dicarboxylic acids.

14. The crystalline polyesterpolyol according to claim 1 wherein the reaction mixture further comprises at least one additional dicarboxylic acid 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, as well as anhydrides, chlorides and ester derived from any of said acids.

15. The crystalline polyesterpolyol according to claim 1 wherein the at least one diol and the at least one dicarboxylic acid are present in the reaction mixture in a molar ratio of 1.5:1 to 1:1.

16. An adhesive composition comprising a polyesterpolyol according to claim 1.

17. The adhesive composition according to claim 16 being liquid at a temperature of 25° C.

18. The adhesive composition according to claim 16 being a curable polyurethane adhesive.

19. The adhesive composition according to claim 16 being a two-component, curable polyurethane adhesive that is liquid at ambient temperature.

Description

BRIEF DESCRIPTION OF THE FIGURES

[0032] FIG. 1 shows the DSC diagrams of a comparative polyesterpolyol obtained from a reaction mixture comprising 1,4-pentane diol and a dicarboxylic acid with a C10 carbon chain. The amorphous character of the polyesterpolyol can be clearly identified by the provided DSC.

[0033] FIGS. 2 and 3 show DSC diagrams of inventive polyesterpolyols which were obtained by reaction of 1,4-pentane diol with a dicarboxylic acid having a C12 and C14 carbon chain, respectively. The unexpected crystalline morphology of each polyesterpolyol can be clearly depicted by the distinct melting peaks in the DSC diagrams.

[0034] FIG. 4 shows the DSC diagram of an inventive polyesterpolyol derived by reacting 1,3-butane diol with a dicarboxylic acid having a C12 carbon chain. The unexpected polymorphous properties of the polyesterpolyol is clearly expressed in the distinct crystallization peak during melting.

[0035] FIG. 5 shows the DSC diagram of an inventive polyesterpolyol derived by reacting 1,2-propylene glycol with a dicarboxylic acid having a C12 carbon chain. The polymorphous properties of the polyesterpolyol is clearly expressed in the distinct crystallization peak during melting.

[0036] FIG. 6 shows the DSC diagram of a comparative polyesterpolyol derived from the reaction of 1,4-butane diol with a dicarboxylic acid having a C12 carbon chain. As can be clearly seen from the provided diagram, the polyesterpolyol does not exhibit the polymorphous properties observed in connection with the similar inventive polyesterpolyols obtained from the reaction of the same dicarboxylic acid with 1,3-butane diol, 1,4-pentane diol and 1,2-propylene glycol, respectively.