IP Library Granted Patent US 7,390,777
Granted Patent B2
US 7,390,777 · App. 10/780,449 · Granted Jun 24, 2008

1,2-dichloroethylene compositions

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Quick Facts
Patent No.
US 7,390,777
App. No.
10/780,449
Granted
Jun 24, 2008
Kind
B2
Abstract

Describes compositions of 1,2-dichloroethylene, particularly trans-1,2-dichloroethylene, stabilized with effective stabilizing amounts of a combination of (a) C3 to C12 alkylene oxide, e.g., butylene oxide, (b) alcohol chosen from aliphatic and cycloaliphatic alcohols having from 2 to 8 carbon atoms, e.g., isopropanol, and (c) a material chosen from (i) C1 to C5 alkoxyphenol, e.g., 4-methoxyphenol, (ii) free radical stabilizer having at least one 2,2,6,6-tetra(lower alkyl)-1-piperidinyloxy-yl group, and (iii) mixtures of (i) and (ii). Also describes use of such compositions for vapor degreasing of soiled articles, e.g., metal parts and soldered circuit boards.

Claims (48)

1. A non-azeotropic solvent composition consisting essentially of trans 1,2-dichloroethylene and an effective stabilizing amount of each of:

a. alkylene oxide having from 3 to 12 carbon atoms and a vicinal epoxy group,

b. alcohol chosen from aliphatic and cycloaliphatic alcohols having from 2 to 8 carbon atoms, and

c. material chosen from (i) lower alkoxyphenol, (ii) free radical stabilizer having at least one 2,2,6,6-tetra(lower alkyl)-1-piperidinyloxy-yl group or 2,2,5,5-tetra(lower alkyl)pyrrolidinyloxy group, or (iii) mixtures of (i) and (ii), wherein the trans 1,2-dichloroethylene is the primary solvent-providing halohydrocarbon of the solvent composition.

2. A composition according to claim 1 wherein the alkylene oxide has from 3 to 4 carbon atoms.

3. A composition according to claim 2 wherein the alkylene oxide is butylene oxide.

4. A composition according to claim 1 wherein the alcohol is an aliphatic alcohol having from 3 to 4 carbon atoms.

5. A composition according to claim 1 wherein the lower alkoxyphenol is a 4-alkoxyphenol.

6. A composition according to claim 5 wherein the 4- alkoxyphenol is 4-methoxyphenol.

7. A composition consisting essentially of trans 1,2-dichloroethylene and an effective stabilizing amount of each of:

a. butylene oxide,

b. isopropyl alcohol, and

c. a free radical stabilizer material having at least one 2,2,6,6-tetra(lower alkyl)-1-piperidinyloxy-yl free radical group.

8. The composition of claim 7 further containing an effective stabilizing amount of 4-methoxyphenol.

9. A composition consisting essentially of trans 1,2-dichloroethylene and an effective stabilizing amount of each of:

a. butylene oxide,

b. isopropyl alcohol, and

c. 4-methoxyphenol.

10. A liquid non-azeotropic halohydrocarbon vapor degreasing solvent composition comprising 1,2-dichloroethylene as the primary halohydrocarbon degreasing solvent and an effective stabilizing amount of each of:

a. alkylene oxide having from 3 to 12 carbon atoms and a vicinal epoxy group,

b. alcohol chosen from aliphatic and cycloaliphatic alcohols having from 2 to 8 carbon atoms, and

c. material chosen from (i) lower alkoxyphenol, (ii) free radical stabilizer having at least one 2,2,6,6-tetra(lower alkyl)-1-piperidinyloxy-yl group or 2,2,5,5-tetra(lower alkyl)pyrrolidinyloxy group, or (iii) mixtures of (i) and (ii).

11. The liquid composition of claim 10 wherein the 1,2-dichloroethylene is principally trans-1,2-dichloroethylene.

12. A composition consisting essentially of trans 1,2-dichloroethylene and an effective stabilizing amount of each of:

a. alkylene oxide having from 3 to 12 carbon atoms and a vicinal epoxy group,

b. isopropanol, and

c. material chosen from (i) lower alkoxyphenol, (ii) free radical stabilizer having at least one 2,2,6,6-tetra(lower alkyl)-1-piperidinyloxy-yl group or 2,2,5,5-tetra(lower alkyl)pyrrolidinyloxy group, or (iii) mixtures of (i) and (ii).

13. A composition consisting essentially of trans 1,2-dichloroethylene and an effective stabilizing amount of each of:

a. alkylene oxide having from 3 to 12 carbon atoms and a vicinal epoxy group,

b. alcohol chosen from aliphatic and cycloaliphatic alcohols having from 2 to 8 carbon atoms, and

c. material chosen from free radical stabilizer having at least one 2,2,6,6-tetra(methyl)-1-piperidinyloxy-yl group.

14. A composition consisting essentially of trans 1,2-dichloroethylene and an effective stabilizing amount of each of:

a. alkylene oxide having from 3 to 12 carbon atoms and a vicinal epoxy group,

b. alcohol chosen from aliphatic and cycloaliphatic alcohols having from 2 to 8 carbon atoms, and

c. material chosen from free radical stabilizer having at least one 2,2,5,5-tetra(lower alkyl)pyrrolidinyloxy group.

15. A liquid halohydrocarbon vapor degreasing solvent composition comprising 1,2-dichloroethylene as the primary degreasing solvent and an effective stabilizing amount of each of:

a. butylene oxide,

b. isopropanol, and

c. material chosen from (i) 4-methoxyphenol, (ii) free radical stabilizer having at least one 2,2,6,6-tetra(methyl)-4-hydroxy-1-piperidinyloxy, or (iii) mixtures of (i) and (ii),

wherein the 1,2-dichloroethylene is principally trans-1,2-dichloroethylene.

16. A composition according to claim 13 wherein the free radical stabilizer is a material having a 2,2,6,6-tetra(methyl)-1-piperidinyloxy-4-yl group.

17. A composition according to claim 16 wherein to free radical stabilizer is a material having the free radical group: 2,2,6,6-tetramethyl-4-hydroxy-1-piperidinyloxy, 2,2,6,6-tetramethyl-4-amino-piperidinyloxy, 2,2,6,6-tetramethyl-4-dimethylamino-piperidinyloxy, 2,2,6,6-tetramethyl-4-ethanoyloxy piperidinyloxy, 2,2,6,6-tetramethyl-4-oxo-1-piperidinyloxy or 2,2,6,6-tetramethyl-4-{(methylsulfonyl)oxy}-1-piperidinyloxy.

18. A composition according to claim 16 wherein the free radical stabilizer is a material having the 2,2,6,6-tetramethyl-1-piperidinyloxy-4-yl benzoate free radical group.

19. A composition according to claim 16 wherein the free radical stabilizer is a bis(2,2,6,6-tetramethyl-1-piperidinyloxy-4-yl) ester of a saturated dicarboxylic acid.

20. A composition according to claim 19 wherein the saturated dicarboxylic acid contains from 2 to 13 carbon atoms.

21. A composition according to claim 20 wherein the free radical stabilizer is bis(2,2,6,6-tetramethyl-1-piperidinyloxy-4-yl) sebacate.

22. A composition according to claim 14 wherein the 2,2,5,5-tetra(lower alkyl)pyrrolidinyloxy group is 2,2,5,5-tetramethyl pyrrolidinyloxy.

23. A composition according to claim 14 wherein the free radical stabilizer is a material having a 2,2,5,5-tetramethyl-3-amino-pyrrolidinyloxy, 2,2,5,5-tetramethyl-1-oxa-3-azacyclopentyl-3-oxy, or 2,2,5,5-tetramethyl-3-pyrrolinyl-1-oxy-3carboxylic acid group.

Assignments (12)
MERGER Recorded Aug 9, 2017
From: AXIALL OHIO, INC.
To: EAGLE US 2 LLC
Reel/Frame 043242/0798 →
RELEASE OF SECURITY INTEREST Recorded Sep 18, 2016
From: BARCLAYS BANK PLC, AS COLLATERAL AGENT
To: AXIALL CORPORATION; ROYAL MOULDINGS LIMITED; PLASTIC TRENDS, INC.; AXIALL OHIO, INC.; GEORGIA GULF CORPORATION; EXTERIOR PORTFOLIO, LLC
Reel/Frame 039857/0569 →
SUBSTITUTION OF ADMINISTRATIVE AGENT & ASSIGNMENT OF RIGHTS UNDER CREDIT AGREEMENT AND LOAN DOCUMENTS Recorded Sep 16, 2016
From: GENERAL ELECTRIC COMPANY, AS ADMINISTRATIVE AGENT
To: WELLS FARGO CAPITAL FINANCE, LLC, AS ADMINISTRATIVE AGENT
Reel/Frame 040055/0033 →
RELEASE OF SECURITY INTEREST Recorded Sep 16, 2016
From: WELLS FARGO CAPITAL FINANCE, LLC
To: EAGLE SPINCO, INC.; EAGLE HOLDCO 3 LLC; EAGLE US 2 LLC; EAGLE CONTROLLED 2 OHIO SPINCO, INC.; EAGLE NATRIUM LLC; EAGLE PIPELINE, INC.; PHH MONOMERS L.L.C.; EAGLE CONTROLLED 1 CANADIAN SPINCO, INC.
Reel/Frame 039768/0655 →
SUBSTITUTION OF ADMINISTRATIVE AGENT AS SUCCESSOR BY MERGER Recorded Sep 15, 2016
From: GENERAL ELECTRIC CAPITAL CORPORATION, AS ADMINISTRATIVE AGENT
To: GENERAL ELECTRIC COMPANY, ADMINISTRATIVE AGENT AS SUCCESSOR BY MERGER
Reel/Frame 040053/0855 →
SECURITY AGREEMENT Recorded Mar 3, 2015
From: AXIALL CORPORATION; ROYAL MOULDINGS LIMITED; PLASTIC TRENDS, INC.; GEORGIA GULF CORPORATION; EXTERIOR PORTFOLIO, LLC; AXIALL OHIO, INC.
To: BARCLAYS BANK PLC, AS COLLATERAL AGENT
Reel/Frame 035121/0600 →
RELEASE OF SECURITY INTEREST Recorded Mar 2, 2015
From: U.S. BANK NATIONAL ASSOCIATION
To: AXIALL OHIO, INC.
Reel/Frame 035115/0559 →
CHANGE OF NAME Recorded Jul 10, 2013
From: EAGLE CONTROLLED 2 OHIO SPINCO, INC.
To: AXIALL OHIO, INC.
Reel/Frame 030764/0631 →
SECURITY AGREEMENT Recorded Feb 11, 2013
From: EAGLE CONTROLLED 2 OHIO SPINCO, INC.
To: U.S. BANK NATIONAL ASSOCIATION, AS NOTES COLLATERAL AGENT
Reel/Frame 029787/0794 →
PATENT SECURITY AGREEMENT Recorded Jan 29, 2013
From: EAGLE SPINCO, INC.; EAGLE HOLDCO 3 LLC; EAGLE US 2 LLC; EAGLE CONTROLLED 2 OHIO SPINCO, INC.; EAGLE NATRIUM LLC; PHH MONOMERS, L.L.C.; EAGLE PIPELINE, INC.; EAGLE CONTROLLED 1 CANADIAN SPINCO, INC.
To: GENERAL ELECTRIC CAPITAL CORPORATION
Reel/Frame 029717/0932 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 28, 2013
From: PPG INDUSTRIES OHIO, INC.
To: EAGLE CONTROLLED 2 OHIO SPINCO, INC.
Reel/Frame 029702/0982 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 22, 2005
From: DOBRASKO, MICHAEL P.; OLINGER, RONALD D.
To: PPG INDUSTRIES OHIO, INC.
Reel/Frame 017013/0004 →