IP Library Granted Patent US 11,884,867
Granted Patent B2
US 11,884,867 · App. 17/606,867 · Granted Jan 30, 2024

Polymerizable surfactants having water whitening resistance and methods for use

Inventors: Lichang Zhou (Lawrenceville, NJ); Adnan Siddiqui (Tenafly, NJ); Dongcheel Lee (Bucheon-Si, KR); Derek Pakenham (Hamilton, NJ); Eugene J. Anderson (Marlton, NJ); Shailesh Majmudar (Stamford, CT); Eunyong Kim (Siheung, KR); Homayoun Jamasbi (Lansdale, PA); An Tran (Newtown, PA); Peng Zhang (Singapore, SG)
Assignee: RHODIA OPERATIONS
C09K23/02C08G65/2636C09D5/022C09D7/45C09D7/65C09D133/04C09J7/38C09J11/08C09J2301/302C09J2301/408C09J2301/414C09J2471/00
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Quick Facts
Patent No.
US 11,884,867
App. No.
17/606,867
Granted
Jan 30, 2024
Kind
B2
Abstract

Disclosed are ethylenically unsaturated salts of allyl (poly)ether sulfates utilized as reactive surfactants or emulsifiers during emulsion polymerization.

Claims (31)

1. A polymerizable surfactant composition comprising: a polymerizable surfactant of formula (I):

wherein R 1 is a bicyclo [d,e,f] heptyl or bicyclo [d,e,f] heptenyl group wherein d is 2, 3, or 4, e is 1 or 2, f is 0 or 1, and the sum of d+e+f=5, and which may, optionally, be substituted on one or more of the ring carbon atoms by one or more (C 1 -C 6 )alkyl groups;

wherein “x” is an integer from 1-40,

wherein “y” is an integer from 1-50;

wherein M + is H + , Na + , NH4 + , K + or Li + ; and optionally, at least one surfactant.

2. The polymerizable surfactant composition of claim 1 , wherein M + is Na + or NH 4 + .

3. The polymerizable surfactant composition of claim 1 , wherein “x” is an integer from 1-20, and wherein “y” is an integer from 1-30.

4. The polymerizable surfactant composition of claim 1 , wherein the at least one surfactant comprising any one of sodium alkylbenzene sultanates or any salt thereof, alkyl sulfosuccinates or any salt thereof, alkyldiphenyloxide disulfonates or any salt thereof, ethoxylated alkylphenol sulfates or any salt thereof, ethoxylated alkylphenol phosphates or any salt thereof, fatty alcohol sulfates or any salt thereof, fatty alcohols phosphates or any salt thereof, alkyl alcohol ethoxylate sulfate or any salt thereof.

5. The polymerizable surfactant composition of claim 1 , wherein “x” is an integer from 1-5.

6. The polymerizable surfactant composition of claim 1 , wherein “y” is an integer from 5-15.

7. A process for preparing a coating comprising introducing the composition of claim 1 as an emulsifier during emulsion polymerization.

8. A polymerizable composition comprising: a polymerizable surfactant of formula (I):

wherein R 1 is a bicyclo [d,e,f] heptyl or bicyclo [d,e,f ] heptenyl group wherein d is 2, 3, or 4, e is 1 or 2, f is 0 or 1, and the sum of d+e+f=5, and which may, optionally, be substituted on one or more of the ring carbon atoms by one or more (C 1 -C 6 ) alkyl groups;

wherein “x” is an integer from 1-40,

wherein “y” is an integer from 1-50;

wherein M + is H + , Na + , NH4 + , K + or Li + ; and

one or more (co)polymerizable monomers comprising acrylate monomers, styrene monomers, or vinyl ester monomers, and

optionally, at least one surfactant.

9. The polymerizable composition of claim 8 , wherein M + is Na + or NH 4 + .

10. The polymerizable composition of claim 8 , wherein “x” is an integer from 1-20, and wherein “y” is an integer from 1-30.

11. The polymerizable composition of claim 8 , wherein the at least one surfactant comprising any one of sodium alkylbenzene sultanates or any salt thereof, alkyl sulfosuccinates or any salt thereof, alkyldiphenyloxide disulfonates or any salt thereof, ethoxylated alkylphenol sulfates or any salt thereof, ethoxylated alkylphenol phosphates or any salt thereof, fatty alcohol sulfates or any salt thereof, fatty alcohols phosphates or any salt thereof.

12. The polymerizable composition of claim 8 , wherein “x” is an integer from 1-5.

13. The polymerizable composition of claim 8 , wherein “y” is an integer from 5-15.

14. The polymerizable surfactant composition of claim 1 , further comprising at least one ingredient selected from chain transfer agents, additives to adjust pH, and compounds utilized as protective colloids.

15. The polymerizable composition of claim 8 , further comprising at least one ingredient selected from chain transfer agents, additives to adjust pH, and compounds utilized as protective colloids.

16. A pressure sensitive adhesive with improved water whitening and water resistance properties comprising a polymer resulting from the polymerizable surfactant composition of claim 1 .

17. A pressure sensitive adhesive with improved water whitening and water resistance properties comprising a polymer resulting from the polymerizable composition of claim 8 .

18. A paint with improved watermark resistance and surfactant leaching resistance properties comprising a polymer resulting from the polymerization of the polymerizable surfactant composition of claim 1 .

19. A paint with improved watermark resistance and surfactant leaching resistance properties comprising a polymer resulting from the polymerization of the polymerizable composition of claim 8 .

20. The paint of claim 19 further comprising acrylic latex.

21. The paint of claim 18 further comprising acrylic latex.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 26, 2024
From: RHODIA OPERATIONS
To: SPECIALTY OPERATIONS FRANCE
Reel/Frame 066374/0642 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 5, 2023
From: ZHOU, LICHANG; SIDDIQUI, ADNAN; LEE, DONGCHEEL; PAKENHAM, DEREK; ANDERSON, EUGENE J.; MAJMUDAR, SHAILESH; KIM, EUNYONG; JAMASBI, HOMAYOUN; TRAN, AN; ZHANG, PENG
To: RHODIA OPERATIONS
Reel/Frame 062281/0260 →