IP Library Granted Patent US 10,307,719
Granted Patent B2
US 10,307,719 · App. 15/177,791 · Granted Jun 4, 2019

Polymeric invert emulsifiers

Inventors: William C Floyd, III (Greenville, SC); Charles F Palmer, Jr. (Greenville, SC)
Assignee: Ethox Chemicals, LLC
B01F17/0028A01N25/30B01F17/005C08G65/22C09K8/36
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Quick Facts
Patent No.
US 10,307,719
App. No.
15/177,791
Granted
Jun 4, 2019
Kind
B2
Abstract

A polymeric invert emulsifier is provided which is particularly suitable for use in demanding environments.

Claims (51)

1. A polymeric invert emulsifier defined by Formula 1:

X[(CH 2 CHR 1 O) n (CH 2 CHR 2 O) m R 3 ] o    Formula 1

wherein X comprises at least one unreacted hydroxyl or amine;

each R 1 is independently —H or —CH 3 ;

each R 2 is independently —H, unsubstituted or substituted branched aryl moiety of 1-22 carbons; or unsubstituted or substituted linear aryl moiety of 1-22 carbons; or unsubstituted or substituted branched alkyl moiety of 1-22 carbons; or unsubstituted or substituted linear alkyl moiety of 1-22 carbons; or —CH 2 OR 4 with the proviso that at least one R 2 is not hydrogen or methyl;

each R 3 is independently —H, unsubstituted or substituted saturated or unsaturated aryl hydrocarbon of 1-25 carbons; or unsubstituted or substituted saturated or unsaturated alkyl hydrocarbon of 1-25 carbons; or an ester group —C(═O)R 5 ;

R 4 is a substituted or unsubstituted branched aryl moiety of 1-22 carbons; or a substituted or unsubstituted linear aryl moiety of 1-22 carbons; or a substituted or unsubstituted branched alkyl moiety of 1-22 carbons; or a substituted or unsubstituted linear alkyl moiety of 1-22 carbons;

R 5 is a substituted or unsubstituted saturated or unsaturated aryl moiety of 1-25 carbons; or a substituted or unsubstituted saturated alkyl moiety of 1-25;

n is an integer of 3-300;

m is an integer of 2-300; and

o is an integer of 2-12.

2. The polymeric invert emulsifier of claim 1 wherein said X comprises a linear or branched alkyl of 3-100 carbons.

3. The polymeric invert emulsifier of claim 1 wherein at least one R 1 is —H.

4. The polymeric invert emulsifier of claim 3 wherein each R 1 is —H.

5. The polymeric invert emulsifier of claim 1 wherein m is an integer of 3-300.

6. The polymeric invert emulsifier of claim 1 wherein R 3 is independently —H or a hydrocarbon chain of 1-3 carbons.

7. The polymeric invert emulsifier of claim 1 having a molecular weight of 1,000-20,000 Da.

8. The polymeric invert emulsifier of claim 1 comprising at least one unreacted hydroxyl.

9. The polymeric invert emulsifier of claim 8 comprising at least one unreacted amine.

10. A polymeric invert emulsifier defined by Formula 1:

X[(CH 2 CHR 1 O) n (CH 2 CHR 2 O) m R 3 ] o    Formula 1

wherein X is a linking group derived from an organic compound containing at least two hydroxyl or amine groups capable of reacting with ethylene oxide;

each R 1 is independently —H or —CH 3 ;

each R 2 is independently —H, unsubstituted or substituted branched aryl moiety of 1-22 carbons; or unsubstituted or substituted linear aryl moiety of 1-22 carbons; or unsubstituted or substituted branched alkyl moiety of 1-22 carbons; or unsubstituted or substituted linear alkyl moiety of 1-22 carbons; or —CH 2 OR 4 with the proviso that at least one R 2 is not hydrogen or methyl;

each R 3 is independently —H, unsubstituted or substituted saturated or unsaturated aryl hydrocarbon of 1-25 carbons; or unsubstituted or substituted saturated or unsaturated alkyl hydrocarbon of 1-25 carbons; or an ester group —C(═O)R 5 ;

R 4 is a substituted or unsubstituted branched aryl moiety of 1-22 carbons; or a substituted or unsubstituted linear aryl moiety of 1-22 carbons; or a substituted or unsubstituted branched alkyl moiety of 1-22 carbons; or a substituted or unsubstituted linear alkyl moiety of 1-22 carbons;

R 5 is a substituted or unsubstituted saturated or unsaturated aryl moiety of 1-25 carbons; or a substituted or unsubstituted saturated alkyl moiety of 1-25;

n is an integer of 3-300;

m is an integer of 2-300; and

o is an integer of 2-12; and

further comprising a second emulsifier.

11. The polymeric invert emulsifier of claim 10 wherein X is a derived from a polyol or polyamine wherein at least two hydroxyl or amine hydrogens are replaced with —(CH 2 CHR 1 O) n (CH 2 CHR 2 O) m R 3 .

12. The polymeric invert emulsifier of claim 11 wherein X is a derived from a polyol or polyamine wherein at least three hydroxyl or amine hydrogens are replaced with —(CH 2 CHR 1 O) n (CH 2 CHR 2 O) m R 3 .

13. The polymeric invert emulsifier of claim 10 wherein all of the labile hydroxyl or amine hydrogens of said X are replaced with (CH 2 CHR 1 O) n (CH 2 CHR 2 O) m R 3 .

14. The polymeric invert emulsifier of claim 10 wherein said X is a derivative of a material selected from the group consisting of ethylene glycol, ethylene diamine, glycerin, trimethylol propane, pentaerythritol, sorbitol, and polyvinyl alcohol.

15. The polymeric invert emulsifier of claim 10 wherein said second emulsifier is a phosphate ester, sulfate, alcohol alkoxylates, alcohol alkoxylate sulfate or alcohol alkoxylate phosphate ester.

16. The polymeric invert emulsifier of claim 15 wherein said second emulsifier is selected from an oleyl alcohol wherein said oleyl alcohol is reacted with three to seven moles of ethylene oxide and phosphate or C6-C24 linear and branched alcohols.

17. The polymeric invert emulsifier of claim 10 wherein said second emulsifier is selected from ethoxylates of lauryl alcohol, ethoxylates of stearyl alcohol, ethoxylates of tridecyl alcohol, ethoxylates of oleyl alcohol, and mixtures thereof.

18. The polymeric invert emulsifier of claim 10 wherein at least one R 1 is —H.

19. The polymeric invert emulsifier of claim 18 wherein each R 1 is —H.

20. The polymeric invert emulsifier of claim 10 wherein m is an integer of 3-300.

21. The polymeric invert emulsifier of claim 10 wherein R 3 is independently —H or a hydrocarbon chain of 1-3 carbons.

22. The polymeric invert emulsifier of claim 10 having a molecular weight of 1,000-20,000 Da.

23. An emulsion comprising the polymeric invert emulsifier of claim 1 .

24. The emulsion of claim 23 comprising an aqueous phase encapsulated in a continuous hydrocarbon phase.

25. The emulsion of claim 24 wherein said aqueous phase is an acidic solution.

26. The emulsion of claim 25 wherein said aqueous phase is a caustic or alkaline solution.

27. An emulsion comprising the polymeric invert emulsifier of claim 10 .

28. The emulsion of claim 27 wherein comprising an aqueous phase encapsulated in a continuous hydrocarbon phase.

29. The emulsion of claim 28 wherein said aqueous phase is an acidic solution.

30. The emulsion of claim 28 wherein said aqueous phase is a caustic or alkaline solution.

Assignments (2)
SECURITY INTEREST Recorded Nov 13, 2024
From: ETHOX CHEMICALS, LLC
To: FIRST NATIONAL BANK OF PENNSYLVANIA
Reel/Frame 069243/0445 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 9, 2016
From: FLOYD, WILLIAM C, III; PALMER, CHARLES F, JR
To: ETHOX CHEMICALS, LLC
Reel/Frame 038944/0503 →
Continuity (3)
Provisional Application 62174689 · Jun 12, 2015
Provisional Application 62184609 · Jun 25, 2015
Related Publication 20160361699A1 · Dec 15, 2016