IP Library Granted Patent US 8,178,648
Granted Patent B2
US 8,178,648 · App. 12/266,368 · Granted May 15, 2012

Diaminium bis-3,5-dicarboxybenzensulfonate and tri-diaminium bis-3,5-dicarboxybenzensulfonate and methods for producing same

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Quick Facts
Patent No.
US 8,178,648
App. No.
12/266,368
Granted
May 15, 2012
Kind
B2
Abstract

A composition of matter comprising a diamine salt and sulfoisophthalic acid in a ratio other than one salt to one acid and a process for producing a diamine salt of sulfoisophthalic acid comprising generating a sulfoisophthalic acid and charging the sulfoisophthalic acid with diamine.

Claims (51)

1. A composition of matter comprising:

a diamine wherein said diamine is selected from the group consisting of: straight, branched and cyclic aliphatic chains;

a sulfoisophthalic acid;

wherein the molar ratio of said diamine to said sulfoisophthalic acid is a 1:2 ratio or a 3:2 ratio.

2. The composition of matter of claim 1 , wherein said diamine is selected from the group consisting of: a primary, a secondary, a tertiary, and combination of primary and secondary, and combination of primary and tertiary, a combination of secondary and tertiary, and a combination of primary, secondary and tertiary amines.

3. The composition of matter of claim 1 , wherein said diamine is 1,6-hexamethylene diamine.

4. The composition of matter of claim 1 , wherein said diamine is 1,4-butanediamine.

5. The composition of matter of claim 1 , wherein said diamine is 2,2,4- and 2,4,4-trimethyl 1,6 hexanediamine.

6. The composition of matter of claim 1 , wherein said diamine is 4,4′-methylenebis(cyclohexylamine).

7. The composition of matter of claim 1 , wherein said diamine is N,N,N′N′-tetramethylethylenediamine.

8. The composition of matter of claim 1 , wherein said composition comprises a mixed salt further comprising three diamine groups.

9. The composition of matter of claim 8 , wherein each of said three diamine groups is different.

10. The composition of matter of claim 8 , wherein two of said three diamine groups is different from a third of said three diamine groups.

11. The composition of matter of claim 8 , wherein all of said three diamine groups are the same.

12. The composition of matter of claim 1 , wherein said composition is provided in solution.

13. A method for producing a diamine salt of sulfoisophthalic acid, said method comprising:

generating a sulfoisophthalic acid; and

charging said sulfoisophthalic acid with diamine in a 1:2 ratio or a 3:2 ratio of said diamine to said sulfoisophthalic acid, wherein said sulfoisophthalic acid is a free acid.

14. The method of claim 13 , wherein said diamine is selected from the group consisting of: straight, branched, and cyclic aliphatic chains.

15. The method of claim 13 , wherein said diamine is selected from the group consisting of: a primary, a secondary, a tertiary, a combination of primary and secondary, a combination of primary and tertiary, a combination of secondary and tertiary, and a combination of primary, secondary and tertiary amines.

16. The method of claim 13 , wherein said diamine is 1,6-hexamethylene diamine.

17. The method of claim 13 , wherein said diamine is 1,4-butanediamine.

18. The method of claim 13 , wherein said diamine is 2,2,4- and 2,4,4-trimethyl 1,6 hexanediamine.

19. The method of claim 13 , wherein said diamine is 4,4′-methylenebis(cyclohexylamine).

20. The method of claim 13 , wherein said diamine is N,N,N′N′-tetramethylethylenediamine.

21. The method of claim 13 wherein said step of generating comprises:

adding isophthalic acid to oleum 30% to create a mixture at a first temperature range of about 60° C. to about 80° C.;

heating said mixture to a temperature between about 190° to about 210° C.;

holding said mixture at a temperature between about 190° C. to about 210° C.;

cooling said mixture to a temperature about less than 170° C.;

adding said mixture to a quantity of water to create an aqueous solution, while keeping the temperature below about 125° C.;

cooling said mixture to a temperature between about 0° C. to about 125° C.;

adding a solution of diamine while temperature is maintained between about 0° C. to about 125° C.;

holding said mixture to a temperature between about 0° C. to about 125° C.;

cooling said mixture to a temperature between about 0° C. to about 50° C.;

holding said mixture at a temperature range of about 0° C. to about 50° C.;

filtering said solution to isolate a solid;

washing said solid; and

drying said solid;

wherein said solid is solid diaminium bis-3,5-dicarboxybenzensulfonate.

22. The method of claim 21 , wherein the method further comprises:

adding the solid diaminium bis-3,5-dicarboxybenzensulfonate to a solvent at a temperature between about 50° C. to about 125° C.;

adding a solution of diamine while holding the temperature between about 50° C. to about 125° C.;

holding said mixture at a temperature range of about 50° C. to about 125° C.;

cooling said mixture to a temperature between about 0° C. to about 50° C.;

holding said mixture at a temperature between about 0° C. to about 50° C.;

filtering said mixture to isolate a solid;

washing said solid; and

drying said solid;

wherein said solid is a tri-diaminium bis-3,5-dicarboxybenzensulfonate.

23. The method of claim 13 , wherein said salt is diaminium bis-3,5-dicarboxybenzensulfonate.

Assignments (2)
NOTICE OF GRANT OF SECURITY INTEREST IN PATENTS Recorded Apr 28, 2015
From: FUTUREFUEL CHEMICAL COMPANY
To: REGIONS BANK, AS COLLATERAL AGENT
Reel/Frame 035517/0708 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 21, 2009
From: TORNO, TRACY A.; STALKER, CANDICE; SOUSA-RAGLE, MARIA ADRIANA; COLEMAN, TODD; HAMPTON, RONNIE
To: FUTUREFUEL CHEMICAL COMPANY
Reel/Frame 022132/0640 →