Hot-melt adhesive composition comprising bio-based polyester polyols

Patent metadata

Field	Value
Publication number	US-12104097-B2
Application number	US-202117301422-A
Country	US
Kind code	B2
Filing date	Apr 2, 2021
Priority date	Oct 15, 2018
Publication date	Oct 1, 2024
Grant date	Oct 1, 2024

Abstract

The present invention relates to a hot-melt adhesive composition comprising at least one polyester polyol based on Betulin and at least one NCO-terminated compound as well as a method for the production of a laminated article using the inventive hot-melt adhesive composition.

First claim

The invention claimed is:

1. A 1K-polyurethane hot-melt adhesive composition comprising an NCO-terminated compound comprising Betulin units, wherein the NCO-terminated compound comprising Betulin units is the reaction product of:
a) at least one polyester polyol that is the reaction product of a reactant mixture comprising Betulin, a dicarboxylic acid, and at least one compound selected from the group consisting of a short-chain polyol, an amine, and a triglyceride; and
b) at least one NCO-terminated polyisocyanate compound.

2. The 1K-polyurethane hot-melt adhesive composition according to claim 1 having a softening point of no more than 120 determined according to the method of Ring & Ball.

3. The 1K-polyurethane hot-melt adhesive composition according to claim 1 having a viscosity of 1000 to 100000 mPas, determined at 130° C. according to DIN EN ISO 2555/2000-01 (Brookfield Thermosel, spindle 27, 10 rpm).

4. The 1K-polyurethane hot-melt adhesive composition according to claim 1 wherein the at least one polyester polyol is the reaction product of a reactant mixture comprising Betulin, a dicarboxylic acid, and a short-chain polyol.

5. The 1K-polyurethane hot-melt adhesive composition according to claim 1 wherein the at least one polyester polyol comprises 5 to 80 mol-% of Betulin moieties.

6. The 1K-polyurethane hot-melt adhesive composition according to claim 1 wherein the at least one polyester polyol is the reaction product of a reactant mixture comprising Betulin, a dicarboxylic acid, and a triglyceride.

7. The 1K-polyurethane hot-melt adhesive composition according to claim 1 wherein the dicarboxylic acid is selected from succinic acid, adipic acid, acelaic acid, sebacic acid, lauric acid, myristic acid, furandicarboxylic acid, isophthalic acid, terephthalic acid, orthophthalic acid, dimerized fatty acids and mixtures thereof.

8. The 1K-polyurethane hot-melt adhesive composition according to claim 1 wherein the at least one NCO-terminated polyisocyanate compound is derived from methylenediphenyl diisocyanate (MDI) or its isomers.

9. The 1K-polyurethane hot-melt adhesive composition according to claim 1 wherein the at least one NCO-terminated polyisocyanate compound is in the form of a monomer, an oligomer, a prepolymer or mixtures thereof;
wherein the monomer is a polyisocyanate selected from the group consisting of 1,5-naphthylene diisocyanate (NDI), 2,4′-diphenylmethylene diisocyanate (MDI), 4,4′-diphenylmethylene diisocyanate (MDI), isomers of toluylene diisocyanate (TDI), triphenylmethylene triisocyanate (MTI), hydrated diphenylmethylene triisocyanate (H12MDI), tetramethylenexylylene diisocyanate (TMXDI), isophorone diisocyanate (IPDI), xylylene diisocyanate (XDI), hexane-1,6-diisocyanate (HDI), pentamethylene diisocyanate (PDI), dicyclohexylmethane diisocyanate, and mixtures thereof; and
wherein the prepolymer is a reaction product of excess polyisocyanate with an OH-group and/or NH-group carrying compound.

10. The 1K-polyurethane hot-melt adhesive composition according to claim 1 wherein a) and b) are reacted with a ratio of NCO to OH of 5:1 to 1:1.

11. The 1K-polyurethane hot-melt adhesive composition according to claim 1 wherein a) and b) are reacted with a ratio of NCO to OH of 2.5:1 to 1.05:1.

12. The 1K-polyurethane hot-melt adhesive composition according to claim 1 wherein the hot-melt adhesive is moisture curable.

13. The 1K-polyurethane hot-melt adhesive composition according to claim 1 which has a solid content of 100%.

14. The 1K-polyurethane hot-melt adhesive composition according to claim 1 wherein the hot-melt adhesive composition does not contain any water or solvent.

15. The 1K-polyurethane hot-melt adhesive composition according to claim 1 having an application temperature of no more than 170° C.

16. An article comprising the 1K-polyurethane hot-melt adhesive composition according to claim 1 .

17. A cured reaction product of the 1K-polyurethane hot-melt adhesive composition according to claim 1 .

18. A method for the production of a laminated article comprising:
i) providing a first substrate;
ii) providing a second substrate;
iii) applying the 1K-polyurethane hot-melt adhesive composition according to claim 1 to at least part of at least one of the first or second substrates, and
iv) contacting the first and second substrates with the applied adhesive to form a laminated article,
wherein the hot-melt adhesive is applied at temperatures of no more than 170° C.

19. The method of claim 18 further comprising exposing the laminated article to moisture to cure the applied adhesive to an irreversible solid form.

Assignees

• Henkel Ag & Co Kgaa

Inventors

• Franken Uwe
• Brandt Adrian
• Kux Alexander
• Jonscher Karin
• Beck Horst

Classifications

• C09J5/06

  involving heating of the applied adhesive · CPC title

• C08G18/7657

  containing two or more aromatic rings · CPC title

• C08G18/3221

  hydroxylated esters of carboxylic acids other than higher fatty acids · CPC title

• C08G2170/20

  Compositions for hot melt adhesives · CPC title

• B32B7/12

  using interposed adhesives or interposed materials with bonding properties · CPC title