Polyurethane adhesive with chemical resistant

Patent metadata

Field	Value
Publication number	US-11629273-B2
Application number	US-201816487491-A
Country	US
Kind code	B2
Filing date	Feb 13, 2018
Priority date	Feb 28, 2017
Publication date	Apr 18, 2023
Grant date	Apr 18, 2023

Abstract

There is provided a pressure sensitive adhesive composition comprising a polyurethane polymer that comprises the reaction product of a polyisocyanate component and a polyol component. The polyol component has a hydrophilic-lipophilic balance (HLB) less than 10. The polyurethane further comprises 0.5 to 10 wt.-% of hydrophilic polymerized units having an HLB greater than 12, such as a reaction product of a polyethylene glycol polymer. In another embodiment, the polyurethane further comprises pendent ethylenically unsaturated groups. Also described are articles such as laminating tapes and protective films as well as methods of bonding substrates with the pressure sensitive adhesive and laminating tape.

First claim

What is claimed is:

1. A pressure sensitive adhesive composition comprising a polyurethane polymer that comprises the reaction product of a polyisocyanate component and a polyol component; wherein the polyol component comprises
at least 50 wt. % of the total polyol components comprises polyol component having a hydrophilic-lipophilic balance of less than 10; and
the polyurethane comprises 0.5 to 5 wt.-% of hydrophilic polymerized units derived from polyethylene glycol polymer having a molecular weight of at least 500 g/mole;
wherein the polyurethane does not comprise a sufficient concentration of hydrophilic groups to render the polyurethane water soluble or water dispersible and the polyurethane polymer further comprises ethylenically unsaturated groups wherein at least a portion of the ethylenically unsaturated groups are pendent.

2. The pressure sensitive adhesive composition of claim 1 wherein the polyol component comprises a polymeric polyester polyol, a polymeric polycaprolactone polyol, or a mixture thereof.

3. The pressure sensitive adhesive composition of claim 1 wherein the polyol component, isocyanate component, or combination thereof comprises at least one six-membered ring structure.

4. The pressure sensitive adhesive composition of claim 1 wherein the polyol component, isocyanate component, or combination thereof comprises alkylene groups having at least 4, 5, or 6 carbon atoms.

5. The pressure sensitive adhesive composition of claim 1 wherein the polyol component comprises an amorphous polymeric polyol.

6. The pressure sensitive adhesive of claim 1 wherein the polyisocyanate component comprises a polyisocyanate that is a liquid at 25° C.

7. The pressure sensitive adhesive of claim 1 wherein the polyol component comprises repeat units of an ortho- or meta- phthalate, and an alkylene group comprising at least 4, 5 or 6 carbon atoms.

8. The pressure sensitive adhesive of claim 1 wherein the polyol component comprises a C36 based polyester polyol.

9. The pressure sensitive adhesive of claim 1 , wherein the ethylenically unsaturated groups are the reaction product of a monomer comprising at least two hydroxyl groups and at least two ethylenically unsaturated groups.

10. The pressure sensitive adhesive of claim 1 , wherein the polyurethane polymer further comprises the reaction product of a functional acid containing compound represented by the generic formula (HX) 2 R 1 A; wherein A is a functional acid group selected from —CO 2 M, —OSO 3 M, —SO 3 M, —OPO(OM) 2, —PO(OM) 2, wherein M is H or a cation; X is O, S, NH or NR, wherein R is an alkylene group comprising 1 to 4 carbon atoms; and R 1 is an organic linking group having a valency of at least 3 and comprises 1 to 50 carbon atoms, optionally includes one or more tertiary nitrogen, ether oxygen, or ester oxygen atoms, and is free from isocyanate-reactive hydrogen containing groups.

11. The pressure sensitive adhesive of claim 10 , wherein the polyurethane comprises between 0.001 and 37 mmol A/100g PU.

12. The pressure sensitive adhesive of claim 1 wherein the polyurethane has a weight average molecular weight ranging from 75,000 to 200,000 g/mole before crosslinking of any ethylenically unsaturated groups of the polyurethane.

13. The pressure sensitive adhesive of claim 1 wherein the pressure sensitive adhesive further comprises a multi-(meth)acrylate crosslinker, an acid-reactive compound, or a combination thereof.

14. The pressure sensitive adhesive of claim 13 wherein the crosslinker is a urethane (meth)acrylate oligomer that comprise alkylene oxide repeat units.

15. The pressure sensitive adhesive composition of claim 1 wherein the adhesive has a 180° peel to glass of at least 15 to 200 N/dm at a peel rate of 300 mm/minute at room temperature after a 72 hour dwell time at 65° C. and 90% relative humidity.

16. The pressure sensitive adhesive composition of claim 1 wherein the pressure sensitive adhesive has a chemical resistance rating of 3-5 in oleic acid or a 70% isopropyl alcohol aqueous solution after 72 hours at 70° C.

17. The pressure sensitive adhesive composition of claim 1 wherein the polyurethane polymer is soluble in methyl ethyl ketone.

18. The pressure sensitive adhesive composition of claim 1 wherein polyurethane polymer is dissolved in a non-aqueous organic solvent.

19. The pressure sensitive adhesive composition of claim 1 wherein the polyethylene glycol polymer has a terminal group comprising two hydroxyl groups.

20. A pressure sensitive adhesive composition comprising a polyurethane polymer that comprises the reaction product of a polyisocyanate component and a polyol component; wherein the polyol component comprises
at least 50 wt.% of the total polyol components comprises polyol component having a hydrophilic-lipophilic balance of less than 10; and
the polyurethane comprises 0.5 to 5 wt.-% of hydrophilic polymerized units derived from polyethylene glycol polymer having a molecular weight of at least 500 g/mole;
wherein the polyurethane does not comprise a sufficient concentration of hydrophilic groups to render the polyurethane water soluble or water dispersible; and
wherein the pressure sensitive adhesive further comprises a multi-(meth)acrylate crosslinker, an acid-reactive compound, or a combination thereof.

21. The pressure sensitive adhesive composition of claim 20 wherein the polyol component comprises a polymeric polyester polyol, a polymeric polycaprolactone polyol, or a mixture thereof.

22. The pressure sensitive adhesive composition of claim 20 wherein the polyol component, isocyanate component, or combination thereof comprises at least one six-membered ring structure.

23. The pressure sensitive adhesive composition of claim 20 wherein the polyol component, isocyanate component, or combination thereof comprises alkylene groups having at least 4, 5, or 6 carbon atoms.

24. The pressure sensitive adhesive composition of claim 20 wherein the polyol component comprises an amorphous polymeric polyol.

25. The pressure sensitive adhesive of claim 20 wherein the polyisocyanate component comprises a polyisocyanate that is a liquid at 25° C.

26. The pressure sensitive adhesive of claim 20 wherein the polyol component comprises repeat units of an ortho- or meta- phthalate, and an alkylene group comprising at least 4, 5 or 6 carbon atoms.

27. The pressure sensitive adhesive of claim 20 wherein the polyol component comprises a C36 based polyester polyol.

28. The pressure sensitive adhesive of claim 20 , wherein the polyurethane polymer further comprises the reaction product of a functional acid containing compound represented by the generic formula (HX) 2 R 1 A; wherein A is a functional acid group selected from —CO 2 M, —OSO 3 M, —SO 3 M, —OPO(OM) 2 , —PO(OM) 2, wherein M is H or a cation; X is O, S, NH or NR, wherein R is an alkylene group comprising 1 to 4 carbon atoms; and R 1 is an organic linking group having a valency of at least 3 and comprises 1 to 50 carbon atoms, optionally includes one or more tertiary nitrogen, ether oxygen, or ester oxygen atoms, and is free from isocyanate-reactive hydrogen containing groups.

29. The pressure sensitive adhesive of claim 20 , wherein the polyurethane comprises between 0.001 and 37 mmol A/100g PU.

30. The pressure sensitive adhesive of claim 20 wherein the po

Assignees

• 3M Innovative Properties Company

Inventors

• Lu Yongshang
• Hao Encai
• Xia Jianhui
• Qie Lili
• Amos David T
• Ho Charlie Chia-Tie
• Polski Lauren A
• Ross Richard B

Classifications

• B32B15/085

  comprising polyolefins · CPC title

• B32B2262/0246

  Acrylic resin fibres · CPC title

• B32B15/088

  comprising polyamides · CPC title

• B32B2266/025

  Polyolefin · CPC title

• C08G2170/40

  Compositions for pressure-sensitive adhesives · CPC title