Moisture curable polyurethane adhesive composition

Patent metadata

Field	Value
Publication number	US-11629277-B2
Application number	US-202117178361-A
Country	US
Kind code	B2
Filing date	Feb 18, 2021
Priority date	Aug 23, 2018
Publication date	Apr 18, 2023
Grant date	Apr 18, 2023

Abstract

This invention relates to moisture curable polyurethane adhesive compositions and more particularly to moisture curable polyurethane adhesive compositions having improved initial tack and moisture permeability when cured. In one embodiment the disclosed moisture curable polyurethane adhesive compositions are suited for use as hot melt adhesives for use in manufacturing textile, clothing and/or footwear articles.

First claim

What is claimed is:

1. A moisture curable polyurethane adhesive composition, comprising an isocyanate-functional polyurethane prepolymer which is the reaction product of a mixture, including:
a) polyols comprising
(a1) an amorphous polyester polyol having a crystallinity of less than 10% determined by DSC according to ISO 11357,
(a2) a semi-crystalline polyester polyol having crystalline and non-crystalline regions and a crystallinity of 20% to 90%, determined by DSC according to ISO 11357, and
(a3) a polyether polyol having an Mn in the range of 400 g/mol to 2500 g/mol, and

b) a polyisocyanate;
wherein the mixture contains less than 5% by weight of crystalline polyols based on the total weight of the moisture curable polyurethane adhesive composition.

2. The moisture curable polyurethane adhesive composition according to claim 1 , wherein the amorphous polyester polyol is produced by polycondensation of an aromatic polycarboxylic acid, an aliphatic polyol and optionally an aliphatic polycarboxylic acid.

3. The moisture curable polyurethane adhesive composition according to claim 1 , wherein the semi-crystalline polyester polyol produced by polycondensation of an aliphatic dicarboxylic acid and two or more aliphatic diols.

4. The moisture curable polyurethane adhesive composition according to claim 3 , wherein one of the aliphatic diols comprises ethylene glycol.

5. The moisture curable polyurethane adhesive composition according to claim 1 , wherein the polyether polyol is selected from polyethylene glycol, polypropylene glycol, polytetramethylene glycol, polybutylene glycol, and mixtures thereof.

6. The moisture curable polyurethane adhesive composition according to claim 1 , wherein the molar ratio of NCO groups in the polyisocyanates to OH groups in the polyols is larger than 2.

7. The moisture curable polyurethane adhesive composition according to claim 1 , wherein the moisture curable polyurethane adhesive composition of the present invention has a melt viscosity at 100° C. in the range of 500 to 9000 mPa·s, measured according to EN ISO 2555 by Brookfield Digital Viscometer RVT using spindle 27 at 10 rpm.

8. The moisture curable polyurethane adhesive composition according to claim 1 , wherein the moisture curable polyurethane adhesive composition when cured exhibits an initial tack of no less than 0.7 N/inch, according to ASTM D2724-1987.

9. The moisture curable polyurethane adhesive composition according to claim 1 , wherein the moisture curable polyurethane adhesive composition when cured exhibits a moisture vapor transmission rate of no less than 4500 g/(m 2 day), according to JIS L1099-2006.

10. The moisture curable polyurethane adhesive composition according to claim 1 being a hot melt adhesive.

11. A moisture permeable adhesive film, formed from the moisture curable polyurethane adhesive composition of claim 1 .

12. Cured reaction products of the moisture curable polyurethane adhesive composition according to claim 1 .

13. An article comprising cured reaction products of the moisture curable polyurethane adhesive composition according to claim 1 .

14. An article of clothing or footwear comprising cured reaction products of the moisture curable polyurethane adhesive composition according to claim 1 .

15. A moisture curable, polyurethane hot melt adhesive composition, comprising an isocyanate-functional polyurethane prepolymer which is the reaction product of a mixture comprising:
(a1) 5% to 35% by weight of an amorphous polyester polyol having an Mn in the range of 400 g/mol to 5000 g/mol and a crystallinity of less than 10%,
(a2) 5% to 35% by weight of a semi-crystalline polyester polyol having crystalline and non-crystalline regions and an Mn in the range of 400 g/mol to 5000 g/mol and a crystallinity of at least 50 to less than 90%, and
(a3) 20% to 70% by weight of a polyether polyol having an Mn in the range of 400 g/mol to 2500 g/mol, and
b) 10% to 30% by weight of a polyisocyanate,
wherein the mixture contains less than 5% by weight of crystalline polyols and in which the weight percentages are based on the total weight of the moisture curable polyurethane adhesive composition.

16. The moisture curable polyurethane hot melt adhesive composition of claim 15 wherein the moisture curable polyurethane adhesive composition when cured exhibits an initial tack of no less than 0.7 N/inch and/or a Moisture Vapor Transmission Rate (MVTR) of no less than 4500 g/(m 2 ·day).

17. The moisture curable polyurethane adhesive hot melt composition of claim 15 comprising less than 1% by weight of crystalline polyols.

18. A method of making a laminate, comprising providing a first moisture permeable substrate having a bonding surface;
providing a second moisture permeable substrate having a bonding surface;
providing the moisture curable, polyurethane hot melt adhesive composition of claim 1 ,
heating the moisture curable, polyurethane hot melt adhesive composition to a temperature in the range of 70 to 130° C. to place it in a molten form;
applying the heated moisture curable, polyurethane hot melt adhesive composition to the first substrate bonding surface;
disposing the second substrate bonding surface on the applied moisture curable, polyurethane hot melt adhesive composition;
cooling the applied moisture curable, polyurethane hot melt adhesive composition; and
exposing the applied moisture curable, polyurethane hot melt adhesive composition to moisture to cure the adhesive.

Assignees

• Henkel Ag & Co Kgaa

Inventors

• Zhu Hongye
• Xie Dan

Classifications

• B32B27/12

  next to a fibrous or filamentary layer · CPC title

• B32B2274/00

  Thermoplastic elastomer material · CPC title

• B32B7/12

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

• B32B27/322

  comprising halogenated polyolefins, e.g. PTFE · CPC title

• C08G18/7671

  containing only one alkylene bisphenyl group · CPC title