Biodegradable, pressure-sensitive adhesive based on polyester-polyurethane

Patent metadata

Field	Value
Publication number	US-10626309-B2
Application number	US-201415100042-A
Country	US
Kind code	B2
Filing date	Dec 15, 2014
Priority date	Dec 16, 2013
Publication date	Apr 21, 2020
Grant date	Apr 21, 2020

Abstract

A biodegradable, pressure sensitive adhesive based on the chemical reaction product of
one or more aliphatic polyester polyols having a hydroxyl functionality of between >2 and <4; one or more aliphatic polyester-polyols having a hydroxyl functionality of between >1 and ≤2; one or more chain extenders having dual hydroxyl functionalities and having a molecular weight of ≤200 g/mo; and, one or more aliphatic diisocyanates;

characterized in that the ratio of the total number of isocyanate groups to the total number of hydroxyl groups in the materials used to form the reaction product is between ≥0.4 and <1.0, and preferably is between ≥0.6 and ≤0.9.

First claim

The invention claimed is:

1. A biodegradable, pressure sensitive adhesive based on the chemical reaction product of:
one or more of a first aliphatic polyester polyol having a hydroxyl functionality of between >2 and <4;
one or more of a second aliphatic polyester polyol having a hydroxyl functionality of between ≤2 and >1;
one or more chain extenders having dual hydroxyl functionalities and having a molecular weight of ≤200 g/mol, and
one or more aliphatic diisocyanates,
in which the ratio of the total number of isocyanate groups to the total number of hydroxyl groups in the materials introduced in the chemical reaction to yield the chemical reaction product is between ≥0.4 and <1.0.

2. The biodegradable, pressure sensitive adhesive according to claim 1 , which is a hydroxyl-functionalized polyurethane hotmelt prepolymer.

3. The, biodegradable, pressure sensitive adhesive according to claim 1 , wherein at least one of the aliphatic polyester polyols has a hydroxyl number of between ≥200 mmol OH/kg and ≤2000 mmol OH/kg.

4. The biodegradable, pressure sensitive adhesive according to claim 1 , wherein at least one of the first aliphatic polyester polyols has a hydroxyl number of between ≥200 mmol OH/kg and ≤2000 mmol OH/kg.

5. The biodegradable, pressure sensitive adhesive according to claim 1 , wherein the percentage of hydroxyl groups originating from the first aliphatic polyester polyols is at least 2.5% of all hydroxyl groups introduced in forming the biodegradable, pressure sensitive adhesive.

6. The biodegradable, pressure sensitive adhesive according to claim 1 , wherein:
at least one of the first aliphatic polyester polyols has a hydroxyl number of between ≥200 mmol OH/kg and ≤2000 mmol OH/kg; and,
at least one of the second aliphatic polyester polyols has a hydroxyl number of between ≥200 mmol OH/kg and ≤8000 mmol OH/kg, and the percentage of hydroxyl groups originating from the first aliphatic polyester polyols is between 2.5% inclusive and 50% inclusive, based on all hydroxyl groups introduced for forming the biodegradable, pressure sensitive adhesive.

7. The biodegradable, pressure sensitive adhesive according to claim 1 , wherein:
at least one of the first aliphatic polyester polyols has a hydroxyl number of between ≥200 mmol OH/kg and ≤2000 mmol OH/kg; and,
at least one of the second aliphatic polyester polyols has a hydroxyl number of between ≥200 mmol OH/kg and ≤8000 mmol OH/kg; and,
and the percentage of hydroxyl groups originating from the aliphatic polyester polyols having a hydroxyl functionality of between greater than two and less than four and a hydroxyl number of between greater than or equal to 200 mmol OH/kg and less than or equal to 2000 mmol OH/kg is between 2.5% inclusive and 50% inclusive of all hydroxyl groups introduced for forming the pressure-sensitively adhesive, biodegradable, chemical reaction product.

8. The biodegradable, pressure sensitive adhesive according to claim 1 , wherein at least one of the aliphatic polyester polyols is a polycaprolactone polyol.

9. The biodegradable, pressure sensitive adhesive according to claim 1 , wherein at least one of the aliphatic polyester polyols is an adipate which comprises ethylene glycol or diethylene glycol as monomer unit.

10. The biodegradable, pressure sensitive adhesive according to claim 1 , wherein at least one of the aliphatic diisocyanates is 4,4′-diisocyanatodicyclohexylmethane or hexamethylene diisocyanate.

11. The biodegradable, pressure sensitive adhesive according to claim 1 , wherein the chain extender is selected from: 2-methyl-1,3 -propanediol, 3-methyl-1,5-pentanediol, ethylene glycol, diethylene glycol, triethylene glycol and, tetraethylene glycol.

12. A biodegradable pressure-sensitive adhesive or a bonding material which comprises a biodegradable, pressure sensitive adhesive based on the chemical reaction product according to claim 1 .

13. The biodegradable pressure-sensitive adhesive or bonding material according to claim 12 , wherein the chemical crosslinking is accomplished by reacting the biodegradable, pressure sensitive adhesive based with a diisocyanate, triisocyanate or higher-functionality isocyanate or with a mixture of said isocyanates, the ratio of the total number of all isocyanate groups to the total number of all hydroxyl groups in the materials introduced overall in the chemical reaction to yield the biodegradable, pressure sensitive adhesive or bonding material is <1.0.

14. A method for producing a biodegradable, pressure sensitive adhesive according to claim 1 , wherein the reaction takes place in the absence of a solvent, or the reaction takes place in an organic solvent, or the reaction takes place in an aqueous medium.

15. A single-sided or double-sided pressure-sensitive adhesive tape or in a single-sidedly or double-sidedly adhering cling film which comprises a biodegradable, pressure sensitive adhesive according to claim 1 .

16. The biodegradable, pressure sensitive adhesive based on the chemical reaction product according to claim 1 , in which the ratio of the total number of isocyanate groups to the total number of hydroxyl groups in the materials introduced in the chemical reaction to produce the biodegradable, pressure sensitive adhesive based on the chemical reaction product is between ≥0.6 and ≤0.9.

17. The biodegradable, pressure sensitive adhesive according to claim 6 , wherein the percentage of hydroxyl groups originating from the first aliphatic polyester polyols have a hydroxyl number of between ≥200 mmol OH/kg and ≤2000 mmol OH/kg is between 5.0% inclusive and 40% inclusive, based on all hydroxyl groups introduced into the reaction for forming the biodegradable, pressure sensitive adhesive.

18. The biodegradable, pressure sensitive adhesive according to claim 7 , wherein:
the percentage of hydroxyl groups originating from the aliphatic polyester polyols having a hydroxyl functionality of between greater than two and less than four and a hydroxyl number of between greater than or equal to 200 mmol OH/kg and less than or equal to 2000 mmol OH/kg is between 5.0% inclusive and 40% inclusive of all hydroxyl groups introduced for forming the pressure-sensitively adhesive, biodegradable, chemical reaction product.

19. A method for producing the biodegradable pressure-sensitive adhesive or the bonding material according to claim 12 , wherein the method takes place in the absence of a solvent, or the method takes place in the presence of an organic solvent, or the method takes place in an aqueous medium.

20. The biodegradable, pressure sensitive adhesive according to claim 10 , wherein at least one of the aliphatic diisocyanates is 4,4′-diisocyanatodicyclohexylmethane.

21. The biodegradable, pressure sensitive adhesive according to claim 11 , wherein the chain extender is selected from: diethylene glycol, triethylene glycol and tetraethylene glycol.

Assignees

• Tesa Se

Inventors

• Ihrig Ralf
• Schümann Uwe
• Spies Manfred
• Weiland Kirstin

Classifications

• C08G18/4277

  Caprolactone and/or substituted caprolactone · CPC title

• C09J175/06 Primary

  from polyesters · CPC title

• C08G18/4241

  from dicarboxylic acids and dialcohols in combination with polycarboxylic acids and/or polyhydroxy compounds which are at least trifunctional · CPC title

• C09J2475/00

  Presence of polyurethane · CPC title

• C08G18/12

  using two or more compounds having active hydrogen in the first polymerisation step · CPC title