IP Library Granted Patent US 11,377,577
Granted Patent B2
US 11,377,577 · App. 15/560,323 · Granted Jul 5, 2022

Pressure sensitive adhesives

Inventors: Jinping Wu (Exton, PA); Xiaoxing Dong (West Chester, PA); Jin Lu (West Chester, PA)
Assignee: Arkema France
C09J175/16B05D3/067C08F290/067C09D175/16C08G2170/40
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Quick Facts
Patent No.
US 11,377,577
App. No.
15/560,323
Granted
Jul 5, 2022
Kind
B2
Abstract

Pressure sensitive adhesive (PSA) compositions that include at least one urethane (meth)acrylate oligomer having a molecular weight between about 2,000 g/mol and about 50,000 g/mol and an OH number of from 0.01 mg KOH/g to 100 mg KOH/g, at least one mono (meth)acrylate functional monomer and at least one tackifying resin. The PSA systems may also optionally include other additives, such as at least one initiator system that includes at least one photo-initiator or free radical initiator. The PSA systems are liquid at a temperature of 25° C.±2° C. with a viscosity of 15,000 cPs or less and are adapted to form smooth, uniform coatings or films upon curing without the application of heat, whereby the resulting films have advantageous properties with respect to peel strength, tack and shear resistance. In embodiments, the PSA systems include less than 1 wt % of solvent and less than 1 wt % of water or are free of solvent and are free of water.

Claims (32)

1. A curable composition comprising:

a) about 30 wt % to 75 wt % of at least two urethane (meth)acrylate oligomers, each of said oligomers having an average in number molecular weight Mn of from 2,000 g/mol to 50,000 g/mol;

b) about 10 wt % to 60 wt % of at least one mono (meth)acrylate functional monomer;

c) about 1 wt % to 50 wt % of at least one tackifying resin; and

d) up to 5 wt % of at least one initiator system;

e) up to 5 wt % of at least one multifunctional monomer;

f) up to 3 wt % of at least one wetting agent; and

g) optionally, other additives,

wherein the sum of percentages of a) + b) + c) + d) + e) + f) + g) is 100%; and

wherein the at least two urethane (meth)acrylate oligomers have a mean OH value from 2 mg KOH/g to 50 mg KOH/g and an average in number-functionality of 1.2 to 1.8 (meth)acrylates.

2. The curable composition of claim 1 , wherein the d) at least one initiator system comprises at least one photo-initiator selected from the group consisting of α-hydroxyketones, phenylglyoxylates, benzyldimethylketals, α-aminoketones, mono-acyl phosphines, bis-acyl phosphines, phosphine oxides and metallocenes and combinations thereof.

3. The curable composition of claim 1 , wherein component a) has an average in number-functionality of from 1.3 to 1.7 (meth)acrylates.

4. The curable composition claim 1 , wherein said composition has a glass transition temperature Tg of 20° C. or less when cured or wherein the composition is liquid at a temperature of 25° C. ±2° C.

5. The curable composition of claim 4 , wherein the c) at least one tackifying resin c) is hydrogenated.

6. The curable composition of claim 1 , wherein the composition comprises less than 1 wt % of non-reactive solvent and less than 1 wt % of water.

7. The curable composition of claim 1 , wherein the c) at least one tackifying resin has a softening temperature of 80° C. or less.

8. The curable composition of claim 1 , wherein the b) at least one mono (meth)acrylate functional monomer is selected from the group consisting of alkoxylated tetrahydrofurfuryl acrylate, isobornyl acrylate, tetrahydrofurfuryl acrylate, caprolactone acrylate, 2(2-ethoxyethoxy) ethyl acrylate, 2-phenoxyethyl acrylate, tetrahydrofurfuryl methacrylate, isooctyl acrylate, 2-octyl acrylate, 2-ethylhexyl acrylate and combinations thereof.

9. The curable composition of claim 1 , wherein the c) at least one tackifying resin is selected from the group consisting of piperylene-based hydrocarbon resins which may be hydrogenated and hydrogenated or non-hydrogenated rosin esters, modified by maleic anhydride rosin esters.

10. The curable composition of claim 1 , wherein said composition is an adhesive curable composition which is a pressure sensitive adhesive curable composition.

11. The curable composition of claim 1 , wherein the b) at least one mono (meth)acrylate functional monomer is selected from the group consisting of alkoxylated tetrahydrofurfuryl acrylate and isobornyl acrylate.

12. The curable composition of claim 1 , wherein each of said urethane (meth)acrylate oligomers a) has an average in number molecular weight Mn of from 5,000 g/mol to 25,000 g/mol.

13. The curable composition of claim 1 , wherein the d) at least one initiator system comprises 1-hydroxy-cyclohexyl-phenyl ketone.

14. A film, wherein it is formed by curing a curable composition as defined in claim 1 .

15. A method of coating a substrate comprising:

applying the curable composition as defined in claim 1 to a substrate and then

curing said curable composition, wherein the curing comprises curing by exposure to one of the group consisting of visible radiation, UV radiation, LED radiation, laser radiation, electron-beam radiation, peroxide, peroxide and an accelerator, heat and combinations thereof.

16. The method of claim 15 , wherein the said applying comprises applying by spraying, knife coating, roller coating, casting, drum coating, dipping and combinations thereof.

17. A cured composition, wherein it is obtained by the curing of a curable composition as defined in claim 1 .

18. The cured composition of claim 17 , wherein it is a cured adhesive composition.

19. The cured composition of claim 17 , wherein it is a cured coating composition.

20. The cured composition of claim 17 , wherein said cured composition is a pressure sensitive adhesive in the form of an adhesive tape, an adhesive sheet, an adhesive spray, a product package, a product label, a construction article or a medical product.

21. The cured composition of claim 20 , wherein it is for packaging, labelling, construction, model making, medicine and construction applications.

Assignments (2)
CHANGE OF ADDRESS Recorded Jul 4, 2025
From: ARKEMA FRANCE
To: ARKEMA FRANCE
Reel/Frame 071814/0739 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 22, 2018
From: WU, JINPING; DONG, XIAOXING; LU, JIN
To: ARKEMA FRANCE
Reel/Frame 045315/0818 →