IP Library Granted Patent US 12,187,922
Granted Patent B2
US 12,187,922 · App. 17/433,372 · Granted Jan 7, 2025

PSA composition with ultra-low temperature performance

Inventors: Ke Zhao (Shanghai, CN); Yurun Yang (Shanghai, CN)
Assignee: Avery Dennison Corporation
C09J133/08C09J7/22C09J7/385C09J2433/00
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Quick Facts
Patent No.
US 12,187,922
App. No.
17/433,372
Granted
Jan 7, 2025
Kind
B2
Abstract

Provided herein is a pressure sensitive adhesive (PSA) comprising two different acrylate polymers and a metal chelating agent to produce the PSA. The PSAs produced according to the methods described herein can be used under a broad range of working temperatures, i.e., from −99° C. to 40° C., e.g., −40° C. to 37° C. These PSAs demonstrate optimal tack and cohesiveness and/or resistance to warm water bath, when affixed to substrates.

Claims (75)

1. A pressure sensitive adhesive comprising:

a polyacrylate base polymer having a glass transition temperature,

a polyacrylate tackifier having a glass transition temperature, and

a metal chelating crosslinker,

wherein both the glass transition temperature of the polyacrylate tackifier and the glass transition temperature of the polyacrylate base polymer are lower than 90° C., and

wherein the glass transition temperature of the polyacrylate base polymer is lower than the glass transition temperature of the polyacrylate tackifier,

wherein the glass transition temperature of the polyacrylate base polymer ranges from −99° C. to −20° C. and wherein the glass transition temperature of the polyacrylate tackifier is greater than −30° C.

2. The pressure sensitive adhesive of claim 1 , wherein the adhesive is a solvent-borne PSA.

3. The pressure sensitive adhesive of claim 1 , wherein the glass transition temperature of the polyacrylate tackifier ranges from −30° C. to 90° C.

4. The pressure sensitive adhesive of claim 1 , wherein the glass transition temperature of the polyacrylate base polymer ranges from −50° C. to −35° C.

5. The pressure sensitive adhesive of claim 1 , the Tg of the polyacrylate base polymer is 5° C. to 100° C. lower than that of the polyacrylate tackifier.

6. The pressure sensitive adhesive of claim 1 , wherein the molecular weight of the polyacrylate base polymer is greater than the molecular weight of the polyacrylate tackifier.

7. The pressure sensitive adhesive of claim 1 , wherein the polyacrylate base polymer has a molecular weight ranging from 200,000 g/mol to 1,500,000 g/mol.

8. The pressure sensitive adhesive of claim 1 , wherein the polyacrylate base polymer is present in an amount ranging from 30 wt. % to 99.9 wt. %, based on the total solid weight of the pressure sensitive adhesive.

9. The pressure sensitive adhesive of claim 1 , wherein the polyacrylate base polymer and/or the polyacrylate tackifier comprise acrylic acid (AA), methyl acrylate (MA), butyl acrylate (BA), 2-ethyl hexyl acrylate (2-EHA), hydroxyethylacrylate (HEA), or combinations thereof.

10. The pressure sensitive adhesive of claim 1 , wherein the polyacrylate tackifier has a molecular weight ranging from 10,000 g/mol to 300,000 g/mol.

11. The pressure sensitive adhesive of claim 1 , wherein the polyacrylate tackifier is present in an amount ranging from 0.5 wt. % to 30 wt. %, based on the total solid weight of the pressure sensitive adhesive.

12. The pressure sensitive adhesive of claim 1 , wherein the polyacrylate base polymer comprises less than 2 wt. % rosin resin, aziridine, or epoxy or combinations thereof.

13. The pressure sensitive adhesive of claim 1 , wherein the pressure sensitive adhesive demonstrates a peel strength greater than 11.5N/inch 10N/inch on polyvinyl chloride, as measured by FINAT Test Method 1 ( 2018 ).

14. The pressure sensitive adhesive of claim 1 , wherein the pressure sensitive adhesive demonstrates a shear ranging greater than 5,000 minutes on stainless steel according to FINAT 2018.

15. The pressure sensitive adhesive of claim 1 , wherein the pressure sensitive adhesive has a peel strength on polyvinyl chloride ranging from 5 N/inch to 20 N/inch.

16. The pressure sensitive adhesive of claim 1 , wherein the pressure sensitive adhesive is capable of remaining attached to a substrate when the pressure sensitive adhesive has been subjected to a temperature ranging from −99° C. to −20° C. for a period of 1 month to 10 years.

17. The pressure sensitive adhesive of claim 1 , wherein the pressure sensitive adhesive is capable of remaining attached to a substrate when the pressure sensitive adhesive has been subjected to a temperature ranging from 20° C. to 40° C. for a period of 1 month to 10 years.

18. The pressure sensitive adhesive of claim 1 , wherein the pressure sensitive adhesive is capable of remaining attached to a substrate when the pressure sensitive adhesive has been in contact with water for a period of 0.5 hour to 24 hours.

19. The pressure sensitive adhesive of claim 1 , wherein the metal chelating agent is a triple aluminum having the structure of the formula below:

wherein the glass transition temperature of the polyacrylate tackifier ranges from −35° C. to −50° C. and the molecular weight of the polyacrylate tackifier ranges from 10,000 g/mol to 300,000 g/mol,

wherein the polyacrylate tackifier is present in an amount ranging from 1 wt. % to 10 wt. % based on the solid weight of the pressure sensitive adhesive; and

wherein the metal chelating crosslinker is present in an amount of 0.1 wt. % to 5 wt. %.

20. The pressure sensitive adhesive of claim 1 , wherein the metal chelating agent is present in an amount ranging from 0.1 wt. % to 5 wt. %, based on the total solid weight of the pressure sensitive adhesive.

21. The pressure sensitive adhesive of claim 1 , wherein the glass transition temperature of the polyacrylate base polymer ranges from −50° C. to −40° C. and the molecular weight of the polyacrylate base polymer ranges from 350,000 g/mol to 450,000 g/mol, and wherein the glass transition temperature of the polyacrylate tackifier ranges from −30° C. to 50° C. and the molecular weight of the polyacrylate tackifier ranges from 100,000 g/mol to 200,000 g/mol.

22. The pressure sensitive adhesive of claim 1 ,

wherein the glass transition temperature of the polyacrylate base polymer ranges from −99° C. to −20° C. and the molecular weight of the polyacrylate base polymer ranges from 200,000 g/mol to 1,500,000 g/mol,

wherein the polyacrylate base polymer is present in an amount ranging from 70 wt. % to 80 wt. %, based on the total solid weight of the pressure sensitive adhesive.

23. The pressure sensitive adhesive of claim 1 ,

wherein the glass transition temperature of the polyacrylate base polymer ranges from −50° C. to −40° C. and the molecular weight of the polyacrylate base polymer ranges from 350,000 g/mol to 1,500,000 g/mol;

wherein the polyacrylate base polymer is present in an amount ranging from 80 wt. % to 99.9 wt. %, based on the total solid weight of the pressure sensitive adhesive;

wherein the glass transition temperature of the polyacrylate tackifier ranges from −30° C. to 50° C. and the molecular weight of the polyacrylate tackifier ranges from 10,000 g/mol to 300,000 g/mol;

wherein the polyacrylate tackifier is present in an amount ranging from 0.5 wt. % to 10 wt. % based on the solid weight of the pressure sensitive adhesive;

wherein the metal chelating crosslinker is present in an amount ranging from 0.8 wt. % to 1.2 wt. %; and

wherein the pressure sensitive adhesive demonstrates a peel strength of at least 11.5 N/inch to 30 N/inch on polyvinyl chloride, as measured by FINAT-1 (2018) and a static shear on stainless steel of greater than 5000 minutes. as measured by FINAT-8 (2018).

24. The pressure sensitive adhesive of claim 1 ,

wherein the glass transition temperature of the polyacrylate base polymer ranges from −50° C. to −40° C. and the molecular weight of the polyacrylate base polymer ranges from 350,000 g/mol to 450,000 g/mol;

wherein the polyacrylate base polymer is present in an amount ranging from 85 wt. % to 98 wt. %, based on the total solid weight of the pressure sensitive adhesive;

wherein the glass transition temperature of the polyacrylate tackifier ranges from −30° C. to 50° C. and the molecular weight of the polyacrylate tackifier ranges from 10,000 g/mol to 300,000 g/mol;

wherein the polyacrylate tackifier is present in an amount ranging from 0.5 wt. % to 10 wt. % based on the solid weight of the pressure sensitive adhesive;

wherein the metal chelating crosslinker is present in an amount ranging from 0.8 wt. % to 1.2 wt. %; and

wherein the pressure sensitive adhesive demonstrates a peel strength of at least 11.7 N/inch to 30 N/inch on polyvinyl chloride, as measured by FINAT-1 (2018) and a static shear on stainless steel is greater than 5000 minutes, as measured by FINAT-8 (2018);

wherein the pressure sensitive adhesive is capable of remaining attached to a substrate when the pressure sensitive adhesive has been subjected to a temperature ranging from −40° C. to 37° C. for a period of 0.5 hour to 10 years; and

wherein the pressure sensitive adhesive is capable of remaining attached to a substrate when the pressure sensitive adhesive has been in contact with water for a period of 0.5 hour to 1 month.

25. A laminate composition comprising a facestock layer and a pressure sensitive adhesive layer comprising the pressure sensitive adhesive of claim 1 .

26. The laminate composition of claim 25 , wherein the pressure sensitive adhesive layer has a thickness ranging from 8 μm to 80 um.

27. The laminate composition of claim 25 , wherein the facestock layer is a film comprising one or more resins selected from the group consisting of polyester, Polypropylene (PP), PP synthesis paper, ABS, polyvinyl chloride (PVC), polyacrylate, polycarbonate (PC), polyamide, polyimide (PI), polyamidoimide, polyacetal, polyphenylene oxide (PPO), polysulfone, polyethersulfone (PES), polyphenylene sulfide, polyether ether ketone (PEEK), polyetherimide (PEI), metallized polyethylene terephthalate (PET), polyvinyl fluoride (PVF), polyethylene ether (PEE), fluorinated ethylene propylene (FEP), polyurethane (PUR), liquid crystal polymers (LCPs, class of aromatic polyester), polyvinylidene fluoride (PVDF), aramid fibers, DIALAMY, (polymer alloys), polyethylene naphthalate (PEN), ethylene/tetrafluoroethylene, (E/TFE), polyphenyl sulfone (PPSU).

28. The laminate composition of claim 25 , wherein the laminate further comprises a topcoat layer disposed on top of the facestock layer.

29. A label comprising the pressure sensitive adhesive of claim 1 .

30. A process for producing a pressure sensitive adhesive, the process comprising:

dissolving in a solvent

a) a polyacrylate base polymer;

b) a polyacrylate tackifier; and

c) a metal chelating crosslinker;

to form a pressure sensitive adhesive solution, wherein the glass transition temperature of the polyacrylate base polymer ranges from −99° C. to −20° C. and wherein the glass transition temperature of the polyacrylate tackifier is greater than −30° C.

31. The process of claim 30 , wherein the solvent is selected from the group consisting of toluene, ethyl acetate, isopropanol, xylene, n-hexane, n-heptane, methyl cyclohexane, butyl acetate, acetone, butanone, and 2-Acetoxy-1-methoxypropane.

32. The process of claim 30 , wherein the method further comprises the step of coating a facestock with the pressure sensitive adhesive solution, and drying the pressure sensitive adhesive solution to produce a label.

33. The process of claim 30 , wherein the method further comprises the step of coating a release liner with the pressure sensitive adhesive solution, drying the pressure sensitive adhesive solution on release liner to produce a dried PSA/liner composition, and applying the dried PSA/liner composition to a facestock to produce a label.

34. The process of claim 32 , wherein the method further comprises applying the label to an article to produce a labeled article, wherein the label is capable of remaining attached to the article after the labeled article has been kept under a temperature that ranges from −99° C. to 40° C. for a period at least 8 hours and/or the label is capable of remaining attached to the article after the label has been in contact with water for a period of at least 0.5 hour.

35. A process for applying a pressure sensitive adhesive to an article, the process comprising:

applying the label produced from the process of claim 32 to the article at an application temperature equal to or less than −40° C.

36. The process of claim 34 , wherein the article is a frozen blood product package.

37. The process of claim 35 , wherein the glass transition temperature of the polyacrylate base polymer is less than the application temperature.

38. The process of claim 35 , wherein the pressure sensitive adhesive demonstrates a peel strength of at least 11.5N/inch to 30 N/inch on polyvinyl chloride, as measured by FINAT Test Method 1 (2018) and a static shear on stainless steel greater than 8000 minutes.

39. The process of claim 35 , wherein the pressure sensitive adhesive remains attached to the article after being subjected to a temperature ranging from −40° C. to 40° C.

40. The process of claim 35 , wherein the pressure sensitive adhesive remains applied to the article after being in contact with water for a period of 0.5 hour to 1 month.

41. A pressure sensitive adhesive solution comprises components of the pressure sensitive adhesive of claim 1 , and a solvent.

42. The pressure sensitive adhesive solution of claim 41 , wherein the polyacrylate base polymer solution is present in an amount ranging from 30 wt. % to 90 wt. % based on the total weight of the pressure sensitive adhesive solution.

43. The pressure sensitive adhesive solution of claim 41 , wherein the solvent is present in an amount ranging from 10 wt. % to 70 wt. % based on the total weight of the pressure sensitive.

44. A label comprising the laminate composition of claim 25 .

Assignments (2)
CHANGE OF CORPORATE ADDRESS Recorded Jul 9, 2024
From: AVERY DENNISON CORPORATION
To: AVERY DENNISON CORPORATION
Reel/Frame 068236/0627 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 24, 2021
From: ZHAO, KE; YANG, YURUN
To: AVERY DENNISON CORPORATION
Reel/Frame 057270/0802 →
Continuity (1)
Related Publication 20220169900A1 · Jun 2, 2022
References Cited (85)
US 4762888A · Sun et al. · 1988 [cited by applicant]
US 4879178A · Sun et al. · 1989 [cited by applicant]
US 5876745A · Muraoka · 1999 [cited by examiner]
US 6153288A · Shih et al. · 2000 [cited by applicant]
US 7462390B2 · Kim et al. · 2008 [cited by applicant]
US 7927703B2 · Xia et al. · 2011 [cited by applicant]
US 8137807B2 · Clapper et al. · 2012 [cited by applicant]
US 8258240B2 · Suzuki et al. · 2012 [cited by applicant]
US 8299182B2 · Inokuchi et al. · 2012 [cited by applicant]
US 8445597B2 · Tomita · 2013 [cited by applicant]
US 8664326B2 · Lee et al. · 2014 [cited by applicant]
US 8828539B2 · Hirose et al. · 2014 [cited by applicant]
US 8846813B2 · Natsui et al. · 2014 [cited by applicant]
US 9011995B2 · Park et al. · 2015 [cited by applicant]
US 9029468B2 · Inui et al. · 2015 [cited by applicant]
US 9464212B2 · Jeong et al. · 2016 [cited by applicant]
US 9828533B2 · Zhang · 2017 [cited by applicant]
US 10266629B2 · Inui et al. · 2019 [cited by applicant]
US 20060036040A1 · Takeko et al. · 2006 [cited by applicant]
US 20060234074A1 · Yun et al. · 2006 [cited by applicant]
US 20110033700A1 · Caylus · 2011 [cited by applicant]
US 20130005911A1 · Okamoto et al. · 2013 [cited by applicant]
US 20130052457A1 · Inui et al. · 2013 [cited by applicant]
US 20130071656A1 · Yamagata et al. · 2013 [cited by applicant]
US 20130274419A1 · Okamoto et al. · 2013 [cited by applicant]
US 20140037951A1 · Shigetomi et al. · 2014 [cited by applicant]
US 20140057091A1 · Krawinkel et al. · 2014 [cited by applicant]
US 20140298862A1 · Yang · 2014 [cited by examiner]
US 20150132567A1 · Shimokuri et al. · 2015 [cited by applicant]
US 20160108295A1 · Ma et al. · 2016 [cited by applicant]
US 20170312852A1 · Brehm et al. · 2017 [cited by applicant]
US 20190002734A1 · Zhang · 2019 [cited by applicant]
US 20190160797A1 · Sakairi et al. · 2019 [cited by applicant]
US 20190194507A1 · Chiba et al. · 2019 [cited by applicant]
CN 1993440 · 2007 [cited by applicant]
CN 100551985 · 2009 [cited by applicant]
CN 100580044 · 2010 [cited by applicant]
CN 101978014 · 2011 [cited by applicant]
CN 101996521 · 2011 [cited by applicant]
CN 101331202 · 2011 [cited by applicant]
CN 102220097 · 2011 [cited by applicant]
CN 101490195 · 2011 [cited by applicant]
CN 101511961 · 2012 [cited by applicant]
CN 103013398 · 2013 [cited by applicant]
CN 101724366 · 2013 [cited by applicant]
CN 103562333 · 2014 [cited by applicant]
CN 103571405 · 2014 [cited by applicant]
CN 103635556 · 2014 [cited by applicant]
CN 103694914 · 2014 [cited by applicant]
CN 102933677 · 2015 [cited by applicant]
CN 102757735 · 2015 [cited by applicant]
CN 102822296 · 2015 [cited by applicant]
CN 102732190 · 2015 [cited by applicant]
CN 102373028 · 2016 [cited by applicant]
CN 103270126 · 2016 [cited by applicant]
CN 104334664 · 2016 [cited by applicant]
CN 106928865 · 2017 [cited by applicant]
CN 107022329 · 2017 [cited by applicant]
CN 107629741 · 2018 [cited by applicant]
CN 106459706 · 2019 [cited by applicant]
CN 109310078 · 2019 [cited by applicant]
EP 1869135 · 2010 [cited by applicant]
EP 1631637 · 2010 [cited by applicant]
EP 2256174 · 2010 [cited by applicant]
EP 1737921 · 2011 [cited by applicant]
EP 1969078 · 2011 [cited by applicant]
EP 2048214 · 2012 [cited by applicant]
EP 2177583 · 2012 [cited by applicant]
EP 2385089 · 2013 [cited by applicant]
EP 2553032 · 2014 [cited by applicant]
EP 2730630 · 2014 [cited by applicant]
EP 2810998 · 2014 [cited by applicant]
EP 3122833 · 2017 [cited by applicant]
EP 3147339 · 2017 [cited by applicant]
EP 2551319 · 2017 [cited by applicant]
WO 2008116033 · 2008 [cited by applicant]
WO 2011119363 · 2011 [cited by applicant]
WO 2012128294 · 2012 [cited by applicant]
WO 2015143649 · 2015 [cited by applicant]
WO 2017116723 · 2017 [cited by applicant]
WO 2018025895 · 2018 [cited by applicant]
WO 2018043624 · 2018 [cited by applicant]
Adhesives & Sealants Industry, “Manufacturing Pressure-Sensitive Adhesive Products: A Coating and Laminating Process,” downloaded from https://www.adhesivesmag.com/articles/86079-manufacturing-pressure-sensitive-adhesiv… [cited by applicant]
International Search Report and Written Opinion dated Oct. 30, 2019 issued in corresponding IA No. PCT/CN2019/076142 filed Feb. 26, 2019. [cited by applicant]
International Preliminary Report on Patentability dated Aug. 25, 2021 issued in corresponding IA No. PCT/CN2019/076142 filed Feb. 26, 2019. [cited by applicant]