IP Library Granted Patent US 8,993,492
Granted Patent B2
US 8,993,492 · App. 13/585,220 · Granted Mar 31, 2015

Crosslinking composition for hydrocarbon gels

Inventors: Larry W. Gatlin (San Antonio, TX); Glen E. Walden (The Woodlands, TX); Ernest McMillan (Kingwood, TX)
Assignee: CST Performance Products Corp.
C07F9/08C09K8/64C09K8/685C09K8/82C10L7/02
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Quick Facts
Patent No.
US 8,993,492
App. No.
13/585,220
Granted
Mar 31, 2015
Kind
B2
Abstract

A crosslinking composition for hydrocarbon gels containing phosphate ester gelling agents comprising a modified imidazoline or pyrimidine including an alkyl group (or unsaturated carbon chain) or of 10 to 22 carbon atoms, a polyamine, and ferric sulfate. The method of making the crosslinking agent features adding the polyamine after reaction of the other ingredients; unique gels formed with the crosslinking agent are particularly effective for LNG at very cold temperatures.

Claims (30)

1. A crosslinking composition for making gels in hydrocarbons comprising the reaction product of, in parts by weight (“p/w”):

(a) 13-17 p/w of a compound of the formula R 3 —O R 4 —O 1-2 H where R 3 is a linear or branched alkyl group of 3-6 carbon atoms and each R 4 is independently a linear or branched alkyl group of 2-6 carbon atoms, or a mixture of such compounds,

(b) 8.5-10.5 p/w of an imidazoline or pyrimidine of the formula

where R 1 is an amino alkyl group containing 2 to 6 carbon atoms and R 2 is an alkyl group (or unsaturated carbon chain) or of 10 to 22 carbon atoms.

(c) 3.6-4.5 p/w of an amide or mixture of amides made by reacting a vegetable oil and a polyamine of the formula

where w is a number from 0-15, x is a number from 2-8, y is 0 or 1, z is a number from 0 to 8, and m and n are independently selected numbers from 0 to 15,

(d) 1.6-2.0 p/w of a vegetable oil diethanolamide,

(e) 0-5.0 p/w sodium dodecene sulfonate in 40-60% water,

(f) 0-5.0 p/w glycerin,

(g) 54-67 p/w ferric sulfate, 40-80% in water, and

(h) 0.1-4 p/w polyamine of the formula

where w is a number from 0-15, x is a number from 2-8, y is 0 or 1, z is a number from 0 to 8, and m and n are independently selected numbers from 0 to 15, said crosslinking composition being effective to form a gel in with a phosphate ester gelling agent in LNG at a temperature of from −20° C. to −28° C.

2. Crosslinking composition of claim 1 wherein said polyamine (h) comprises dimethylaminopropyl amine.

3. Crosslinking composition of claim 1 wherein said imidazoline (b) comprises an imidazoline made by reacting diethylene triamine with tall oil.

4. Crosslinking composition of claim 1 wherein said amide (c) comprises an amide made by reacting soybean oil with dimethyl aminopropylamine.

5. Crosslinking composition of claim 1 wherein said diethanolamide (d) comprises a diethanolamide made by reacting coconut oil with diethanolamine.

6. Crosslinking composition of claim 1 wherein R 1 in said imidazoline (b) contains two amine groups.

7. Crosslinking composition of claim 1 wherein said polyamine (h) comprises didecylamionohexylamine.

8. Crosslinking composition of claim 1 wherein said compound (a) comprises ethylene glycol 2-butane ethanol.

9. Method of making a crosslinking composition for hydrocarbon gels comprising (a) mixing together (i) 13-17 parts by weight one or more compounds of the formula R 3 —O R 4 —O 1-2 H where R 3 is a linear or branched alkyl group of 3-6 carbon atoms and each R 4 is independently a linear or branched alkyl group of 2-6 carbon atoms, or a mixture of such compounds,

(ii) 8.5-10 parts by weight of an imidazoline or pyrimidine of the formula

where R 1 is an amino alkyl group containing 2 to 6 carbon atoms and R 2 is an alkyl group (or unsaturated carbon chain) or of 10 to 22 carbon atoms, or a pyrimidine having similar substituent groups, (iii) 3.6-4.5 parts by weight of an amide or mixture of amides made by reacting a vegetable oil and a polyamine of the formula

where w is a number from 0-15, x is a number from 2-8, y is 0 or 1, z is a number from 0 to 8, and m and n are independently selected numbers from 0 to 15,

(iv) 1.6-2.0 parts by weight of a vegetable oil diethanolamide, (v) 4.0-5.0 parts by weight sodium dodecene sulfonate in 40-60% water, and (vi) 5.0-5.0 parts by weight glycerin, thereby causing an exotherm, (b) further mixing into said mixture 0.1-4 parts by weight of a polyamine of the formula

where w, x, y, z, m, and n are as indicated above, (c) mixing into said mixture 54-67 parts by weight ferric sulfate (40-80% in water), and (d) cooling said mixture throughout said mixing in steps (a), (b), and (c) to control said exotherm.

10. Method of claim 9 wherein said polyamine in step (b) comprises dimethylaminopropyl amine.

11. Method of claim 9 wherein said imidazoline in step (a) (ii) comprises an imidazoline made by reacting diethylene triamine with tall oil.

12. Method of claim 9 wherein said amide (a) (iii) comprises an amide made by reacting soybean oil with dimethyl aminopropylamine.

13. Method of claim 9 wherein said diethanolamide in step (a) (iv) comprises a diethanolamide made by reacting coconut oil with diethanolamine.

14. Method of claim 9 wherein said compound (a) (i) comprises ethylene glycol 2-butane ethanol.

Assignments (3)
MERGER Recorded Mar 20, 2017
From: CST PERFORMANCE PRODUCTS CORP.
To: LAMBERTI USA INCORPORATED
Reel/Frame 041637/0961 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 23, 2013
From: CONLEN SURFACTANT TECHNOLOGY, INC.; CONLEN AGRO SCIENCES, INC.
To: CST PERFORMANCE PRODUCTS CORP.
Reel/Frame 031068/0621 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 14, 2012
From: GATLIN, LARRY W.; WALDEN, GLEN E.; MCMILLAN, ERNEST
To: CONLEN SURFACTANT TECHNOLOGY, INC.
Reel/Frame 028784/0156 →
Continuity (1)
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