IP Library › Granted Patent US 12,291,646
Granted Patent B2
US 12,291,646 · App. 17/654,613 · Granted May 6, 2025

Photocurable (meth)acrylate compositions

Inventors: Shuhua Jin (Cheshire, CT); Chih-Min Cheng (Westford, MA)
Assignee: Henkel AG & Co. KGAA
C09D175/14B01D67/0088B01D69/02B01D69/12B01D71/5211B01D71/54C09D7/43C09D7/65B01D61/025B01D2325/30
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 12,291,646
App. No.
17/654,613
Granted
May 6, 2025
Kind
B2
Abstract

Photocurable (meth)acrylate compositions for forming features on the surfaces of membranes, and particularly, on membranes used in osmosis and reverse-osmosis applications, such as membrane filters.

Claims (40)

1. A photocurable composition comprising:

a) a (meth)acrylate-functionalized polyether urethane component, wherein the (meth)acrylate-functionalized polyether urethane component is present in an amount of about 20% to about 60% by weight based on the total weight of the curable composition;

b) a (meth)acrylate monomer;

c) an organic filler; and

d) a photoinitiator,

wherein when exposed to UV or visible light the curable composition forms a cured reaction product, the cured reaction product demonstrates a loss of mass of: 1) less than 2% when exposed to acidic, aqueous conditions of a pH=1.5 for about 4 weeks at a temperature of about 50° C. and/or 2) less than 3% when exposed to basic, aqueous conditions of a pH=12.5 for about 4 weeks at a temperature of about 50° C.

2. The curable composition of claim 1 , wherein the cured reaction product has a Shore D hardness of about 20 or greater.

3. The curable composition of claim 1 , wherein the curable composition has a viscosity of about 10,000 to about 100,000 cps.

4. The curable composition of claim 1 , wherein the curable composition has a thixotropic index of about 1.5 to about 6.

5. The curable composition of claim 1 , wherein the (meth)acrylate-functionalized polyether urethane component is a polyether urethane acrylate oligomer.

6. The curable composition of claim 1 , wherein the (meth)acrylate monomer is present in an amount of about 10% to about 60% by weight based on the total weight of the curable composition.

7. The curable composition of claim 1 , wherein the (meth)acrylate monomer is a polyethylene glycol diacrylate.

8. The curable composition of claim 1 , wherein the organic filler is present in an amount of about 0.1% to about 40% by weight based on the total weight of the curable composition.

9. The curable composition of claim 1 , wherein the organic filler is a hydrophobic polyolefin-based organic thickener.

10. The curable composition of claim 1 , wherein the organic filler is selected from the group consisting of polyvinylchloride powder, polypropylene powder, and combinations thereof.

11. The curable composition of claim 1 , wherein the photoinitiator is present in an amount of about 0.2% to about 5% by weight based on the total weight of the curable composition.

12. The curable composition of claim 1 , wherein the photoinitiator is a polymeric structure to which is attached at least one chromophore that is excited by radiation in the UV light or visible light range.

13. A composite membrane structure comprising:

a) a membrane comprising at least one surface; and

b) the cured reaction product of the curable composition of claim 1 disposed on at least a portion of the at least one surface of the membrane.

14. The composite membrane structure of claim 13 , wherein the cured reaction product is adhesively bonded to at least a portion of the at least one surface of the membrane.

15. The composite membrane structure of claim 13 , wherein the cured reaction product is disposed on at least a portion of the at least one surface of the membrane in a pre-determined pattern.

16. The composite membrane structure of claim 15 , wherein the pre-determined pattern is selected from the group consisting of stripes, waves, circles, ovals, arcs, squares, rectangles, diamonds, pentagons, hexagons, stars, chevrons, a random pattern, and combinations thereof.

17. A method of a producing a hydrolytically stable cured reaction product comprising the steps of:

a) providing a curable composition comprising:

i) a (meth)acrylate-functionalized polyether urethane component, wherein the (meth)acrylate-functionalized polyether urethane component is present in an amount of about 20% to about 60% by weight based on the total weight of the curable composition;

ii) a (meth)acrylate monomer;

iii) an organic filler; and

iv) a photoinitiator, and

b) exposing the curable composition to a source of UV or visible light to form a cured reaction product,

wherein hydrolytic stability is demonstrated when the cured reaction product demonstrates a loss of mass of: 1) less than 2% when exposed to acid, aqueous conditions of a pH=1.5 for about 4 weeks at a temperature of about 50° C. or 2) less than 3% when exposed to basic, aqueous conditions of a pH=12.5 for about 4 weeks at a temperature of about 50° C.

18. The method of claim 17 , wherein the cured reaction product has a Shore D hardness of about 20 or greater.

19. The method of claim 17 , wherein the (meth)acrylate-functionalized polyether urethane component is a polyether urethane acrylate oligomer.

20. The method of claim 17 , wherein the (meth)acrylate monomer is present in an amount of about 10% to about 60% by weight based on the total weight of the curable composition.

21. The method of claim 17 , wherein the (meth)acrylate monomer is a polyethylene glycol diacrylate.

22. The method of claim 17 , wherein the organic filler is present in an amount of about 0.1% to about 40% by weight based on the total weight of the curable composition.

23. The method of claim 17 , wherein the organic filler is a hydrophobic polyolefin-based organic thickener.

24. The method of claim 19 , wherein the organic filler is selected from the group consisting of polyvinylchloride powder, polypropylene powder, and combinations thereof.

25. The method of claim 17 , wherein the photoinitiator is present in an amount of about 0.2% to about 5% by weight based on the total weight of the curable composition.

26. The method of claim 17 , wherein the photoinitiator has a polymeric structure to which is attached at least one chromophore that is excited by radiation in the UV light or visible light range.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 4, 2022
From: JIN, SHUHUA; CHENG, CHIH-MIN
To: HENKEL IP & HOLDING GMBH
Reel/Frame 060719/0412 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 4, 2022
From: HENKEL IP & HOLDING GMBH
To: HENKEL AG & CO. KGAA
Reel/Frame 060719/0518 →
Continuity (3)
Continuation PCTUS2020051644 · Sep 18, 2020
Provisional Application 62902659 · Sep 19, 2019
Related Publication 20220204809A1 · Jun 30, 2022
References Cited (38)
US 4254230A · Howard · 1981 [cited by examiner]
US 4258123A · Nagashima et al. · 1981 [cited by applicant]
US 4439600A · Moran, Jr. · 1984 [cited by examiner]
US 4505793A · Tamoto et al. · 1985 [cited by applicant]
US 4693953A · Torikai · 1987 [cited by examiner]
US 5094749A · Seita · 1992 [cited by examiner]
US 5395862A · Neckers et al. · 1995 [cited by applicant]
US 5451343A · Neckers et al. · 1995 [cited by applicant]
US 5545676A · Palazzotto et al. · 1996 [cited by applicant]
US 8933146B2 · Sommer · 2015 [cited by examiner]
US 8993897B2 · Sekito · 2015 [cited by examiner]
US 9238221B2 · Van Berchum · 2016 [cited by examiner]
US 9718910B2 · Otani · 2017 [cited by examiner]
US 10213743B2 · Van Berchum · 2019 [cited by examiner]
US 10633499B2 · Van Engelen · 2020 [cited by examiner]
US 20040011429A1 · Bradford et al. · 2004 [cited by applicant]
US 20080159706A1 · Andre et al. · 2008 [cited by applicant]
US 20090012202A1 · Jacobine et al. · 2009 [cited by applicant]
US 20110097645A1 · Van Baak · 2011 [cited by examiner]
US 20120094184A1 · Abe · 2012 [cited by examiner]
US 20120276373A1 · Port et al. · 2012 [cited by applicant]
US 20130103157A1 · Kourtis · 2013 [cited by examiner]
US 20150166704A1 · Otani et al. · 2015 [cited by applicant]
US 20180320021A1 · Potzmann · 2018 [cited by applicant]
US 20190284430A1 · Sigel · 2019 [cited by examiner]
CA 2610961A1 · 2017 [cited by examiner]
CN 1206472A · 1999 [cited by examiner]
CN 001896156 · 2007 [cited by applicant]
CN 105801807 · 2016 [cited by applicant]
CN 107921373A · 2018 [cited by examiner]
EP 0369645 · 1990 [cited by applicant]
EP 0563925 · 1993 [cited by applicant]
JP 08060043 · 1996 [cited by applicant]
WO WO2011027138A1 · 2011 [cited by examiner]
WO 2013114297 · 2013 [cited by applicant]
WO WO2015110827A1 · 2015 [cited by examiner]
PCT International Search Report issued in connection with International Application No. PCT/US2020/051644 mailed Jan. 22, 2021. [cited by applicant]
PCT International Search Report issued in connection with International Application No. PCT/US2020/051652 mailed Dec. 30, 2020. [cited by applicant]