IP Library › Granted Patent US 7,960,331
Granted Patent B2
US 7,960,331 · App. 12/192,229 · Granted Jun 14, 2011

Replacement solvents having improved properties and methods of using the same

View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 7,960,331
App. No.
12/192,229
Granted
Jun 14, 2011
Kind
B2
Abstract

CFC replacement solvent compositions, methods of using the same and methods of making the same. These compositions meet or exceed the solvency, flammability, and compatibility requirements for CFC's while providing similar or improved environmental and toxicological properties. These solvent compositions have applications including, but not limited to, oxygen handling, refrigeration or heat pumps, electronics, implantable prosthetic devices, and optical equipment.

Claims (252)

1. A cleaning method comprising:

applying to a device a solvent composition comprising

(1) a first compound selected from the group consisting of fluorinated alkanes, diones, heterocyclics, cycloalkenes, anhydrides, ketones, cycloalkenes, aromatics, acetates, ethers, esters, alcohols, and alkenes, and

(2) a second compound which contains one bromine atom and is selected from the group consisting of partially fluorinated aromatics, ketones, ethers, and alkenes,

wherein the first compound is selected from the group consisting of

1-chloro-2,2,2-trifluoroethyl difluoromethyl ether (isoflurane);

2-chloro-1,1,2-trifluoroethyl difluoromethyl ether (enflurane);

methyl 2,2,2-trifluroethyl-1-(trifluoromethyl)ether;

heptafluoropropyl 1,2,2,2-tetrafluoroethyl ether;

perfluorodibutyl ether;

3,3,3-trifluoro-bis-2,2-(trifluoromethyl)-1-propanol;

1,2-(Z)-bis(perfluoro-n-butyl)ethylene;

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)-2-propanol;

2H,3H-decafluoropentane (Vertrel XF);

ethyl-perfluorobutyl ether;

1,1,1,5,5,5-hexafluoro-2,4-pentanedione;

perfluoro-2-butyltetrahydrofuran;

1H,2H,4H-nonafluorocyclohexane;

1-methoxy-2-trifluoromethyl-1,3,3,3-tetrafluoro-1-propene;

fluoromethyl 2,2,2-trifluoro-1-(trifluoromethyl)ethyl ether (SEVOFLURANE);

(E)-2,3-dichlorohexafluoro-2-butene;

3,3-dichloro-1,1,1,2,2-pentafluoropropane (HCFC-225);

methyl-1,1,2,2,3,3-hexafluoropropyl ether;

trifluoroacetic anhydride;

2,2-difluoroethyl-1,1,2,2-tetrafluoroethyl ether;

1,3-dichloro-1,1,2,2,3-pentafluoropropane (HCFC-225cb, AK-225G);

bis(2,2,2-trifluoroethyl)ether;

methyl heptafluoropropyl ketone;

difluoromethyl-2,2,3,3-tetrafluoropropyl ether;

bis(difluoromethoxy)-tetrafluoroethane;

2-chloro-1,1,2-trifluoroethyl ethyl ether;

1-(2,2,2-trifluoroethoxy)nonafluoro-cyclohexene;

1,2-dichloro-3,3,4,4,5,5,6,6-octafluoro-cyclohexene;

ethyl-1,1,2,2-tetrafluoroethyl ether;

perfluorotoluene;

methyl trifluoroacetate;

methyl pentafluoropropanoate; and

1,2-dichloro-hexafluoro-cyclopentene, and

wherein the second compound is selected from the group consisting of

4-bromo-3-chloro-3,4,4-trifluoro-1-butene;

1-bromo-2-(trifluoromethyl)-3,3,3-trifluoropropene;

4-bromo-1,1,1,3,4,4-hexafluoro-2-(trifluoromethyl)-2-butene;

4-bromo-1,1,1,4,4-pentafluoro-2-(trifluoromethyl)-2-butene;

3-bromo-1,1,2,3,4,4,4-heptafluorobutene;

1,1,1,4,4-pentafluoro-4-bromo-2-trifluoromethyl-2-butene;

1-bromo-1,3,3,3-tetrafluoro-2-(trifluoromethyl)-1-propene;

(Z)-1-bromo-perfluoro-2-butene;

4-bromo-1,1,2,3,3,4,4-heptafluorobutene;

(Z)-2-bromo-1,1,1,3,4,4,4-heptafluoro-2-butene;

(E)-2-bromo-1,1,1,3,4,4,4-heptafluoro-2-butene;

(E)-1-bromo-perfluoro-2-butene;

(E)-2-bromo-1,1,1,4,4,4-hexafluoro-2-butene;

1-bromo-bis(perfluoromethyl) ethylene;

1-(bromodifluoromethoxy)-2-(trifluoromethyl)-1,3,3,3-tetrafluoro-1-propene;

2-bromo-3,3,4,4,4-pentafluorobutene;

3-bromo-2,3,4,4,4-pentafluorobutene;

4-bromo-2,3,3,4,4-pentafluorobutene;

(Z)-1-(bromodifluoromethoxy)-1,2,3,3,3-pentafluoro-1-propene;

3-bromo-3,3-difluoro-2-(trifluoromethyl)-propene;

(Z)-1-bromo-1,1,4,4,4-pentafluoro-2-butene;

(E)-1-(bromodifluoromethoxy)-1,2,3,3,3-pentafluoro-1-propene;

1-(bromodifluoromethoxy)-2-(trifluoromethyl)-3,3,3-trifluoro-1-propene;

2-bromo-1,1,2,2-tetrafluoroethoxy-trifluomethene;

(E)-1-bromo-1,1,4,4,4-pentafluoro-2-butene;

4-bromo-3,3,4,4-tetrafluoro-1-butene;

(Z)-1-bromo-1,2-difluoro-2-(2,2,2-trifluoroethoxy)-ethene;

(bromodifluoromethyl)-pentafluorobenzene;

(Z)-1-(bromodifluoromethoxy)-2-(trifluoromethyl)ethane;

2-bromoheptafluorotoluene;

(2,2,2-trifluoroethyl)(2-bromo-2,2-difluoroethyl)ether;

3-bromoheptafluorotoluene;

4-bromoheptafluorotoluene;

1-(bromodifluoromethoxy)-1-(trifluoromethyl)ethene;

(E)-1-(bromodifluoromethoxy)-2-(trifluoromethyl)ethene;

1-bromo-2,4,6-tris(trifluoromethyl)benzene;

4-bromo-1,1,2,3,3-pentafluorobutene;

(E)-1-(bromodifluoromethoxy)-2-(trifluoromethoxy)ethene;

(Z)-1-(bromodifluoromethoxy)-2-(trifluoromethoxy)ethene;

1,1,4,4,4-pentafluoro-1-bromo-2-butanone;

1,1,5,5,5-pentafluoro-1-bromo-3-pentanone;

3-bromo-2,3,3-trifluoropropene;

3-bromo-1,3,3-trifluoropropene; and

3-bromo-3,3-difluoro-1-propene.

2. The cleaning method according to claim 1 , wherein the device is one of an oxygen handling system, refrigeration system, implantable prosthetic device, electronic, or optical equipment.

3. A method for applying a polymer coating, comprising,

dissolving the polymer coating material in a solvent composition comprising

(1) a first compound selected from the group consisting of fluorinated alkanes, diones, heterocyclics, cycloalkanes, anhydrides, ketones, cycloalkenes, aromatics, acetates, ethers, esters, alcohols, and alkenes, and

(2) a second compound which contains one bromine atom and is selected from the group consisting of partially fluorinated aromatics, ketones, ethers, and alkenes, and applying the polymer coating material dissolved in said solvent to an item,

wherein the first compound is selected from the group consisting of

1-chloro-2,2,2-trifluoroethyl difluoromethyl ether (isoflurane);

2-chloro-1,1,2-trifluoroethyl difluoromethyl ether (enflurane);

methyl 2,2,2-trifluroethyl-1-(trifluoromethyl)ether;

heptafluoropropyl 1,2,2,2-tetrafluoroethyl ether;

perfluorodibutyl ether;

3,3,3-trifluoro-bis-2,2-(trifluoromethyl)-1-propanol;

1,2-(Z)-bis(perfluoro-n-butyl)ethylene;

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)-2-propanol;

2H,3H-decafluoropentane (Vertrel XF);

ethyl-perfluorobutyl ether;

1,1,1,5,5,5-hexafluoro-2,4-pentanedione;

perfluoro-2-butyltetrahydrofuran;

1H,2H,4H-nonafluorocyclohexane;

1-methoxy-2-trifluoromethyl-1,3,3,3-tetrafluoro-1-propene;

fluoromethyl 2,2,2-trifluoro-1-(trifluoromethyl)ethyl ether (SEVOFLURANE);

(E)-2,3-dichlorohexafluoro-2-butene;

3,3-dichloro-1,1,1,2,2-pentafluoropropane (HCFC-225);

methyl-1,1,2,2,3,3-hexafluoropropyl ether;

trifluoroacetic anhydride;

2,2-difluoroethyl-1,1,2,2-tetrafluoroethyl ether;

1,3-dichloro-1,1,2,2,3-pentafluoropropane (HCFC-225cb, AK-225G);

bis(2,2,2-trifluoroethyl)ether;

methyl heptafluoropropyl ketone;

difluoromethyl-2,2,3,3-tetrafluoropropyl ether;

bis(difluoromethoxy)-tetrafluoroethane;

2-chloro-1,1,2-trifluoroethyl ethyl ether;

1-(2,2,2-trifluoroethoxy)nonafluoro-cyclohexene;

1,2-dichloro-3,3,4,4,5,5,6,6-octafluoro-cyclohexene;

ethyl-1,1,2,2-tetrafluoroethyl ether;

perfluorotoluene;

methyl trifluoroacetate;

methyl pentafluoropropanoate; and

1,2-dichloro-hexafluoro-cyclopentene, and

wherein the second compound is selected from the group consisting of

4-bromo-3-chloro-3,4,4-trifluoro-1-butene;

1-bromo-2-(trifluoromethyl)-3,3,3-trifluoropropene;

4-bromo-1,1,1,3,4,4-hexafluoro-2-(trifluoromethyl)-2-butene;

4-bromo-1,1,1,4,4-pentafluoro-2-(trifluoromethyl)-2-butene;

3-bromo-1,1,2,3,4,4,4-heptafluorobutene;

1,1,1,4,4-pentafluoro-4-bromo-2-trifluoromethyl-2-butene;

1-bromo-1,3,3,3-tetrafluoro-2-(trifluoromethyl)-1-propene;

(Z)-1-bromo-perfluoro-2-butene;

4-bromo-1,1,2,3,3,4,4-heptafluorobutene;

(Z)-2-bromo-1,1,1,3,4,4,4-heptafluoro-2-butene;

(E)-2-bromo-1,1,1,3,4,4,4-heptafluoro-2-butene;

(E)-1-bromo-perfluoro-2-butene;

(E)-2-bromo-1,1,1,4,4,4-hexafluoro-2-butene;

1-bromo-bis(perfluoromethyl) ethylene;

1-(bromodifluoromethoxy)-2-(trifluoromethyl)-1,3,3,3-tetrafluoro-1-propene;

2-bromo-3,3,4,4,4-pentafluorobutene;

3-bromo-2,3,4,4,4-pentafluorobutene;

4-bromo-2,3,3,4,4-pentafluorobutene;

(Z)-1-(bromodifluoromethoxy)-1,2,3,3,3-pentafluoro-1-propene;

3-bromo-3,3-difluoro-2-(trifluoromethyl)-propene;

(Z)-1-bromo-1,1,4,4,4-pentafluoro-2-butene;

(E)-1-(bromodifluoromethoxy)-1,2,3,3,3-pentafluoro-1-propene;

1-(bromodifluoromethoxy)-2-(trifluoromethyl)-3,3,3-trifluoro-1-propene;

2-bromo-1,1,2,2-tetrafluoroethoxy-trifluoroethene;

(E)-1-bromo-1,1,4,4,4-pentafluoro-2-butene;

4-bromo-3,3,4,4-tetrafluoro-1-butene;

(Z)-1-bromo-1,2-difluoro-2-(2,2,2-trifluoroethoxy)-ethene;

(bromodifluoromethyl)-pentafluorobenzene;

(Z)-1-(bromodifluoromethoxy)-2-(trifluoromethyl)ethane;

2-bromoheptafluorotoluene;

(2,2,2-trifluoroethyl)(2-bromo-2,2-difluoroethyl)ether;

3-bromoheptafluorotoluene;

4-bromoheptafluorotoluene;

1-(bromodifluoromethoxy)-1-(trifluoromethyl)ethane;

(E)-1-(bromodifluoromethoxy)-2-(trifluoromethyl)ethane;

1-bromo-2,4,6-tris(trifluoromethyl)benzene;

4-bromo-1,1,2,3,3-pentafluorobutene;

(E)-1-(bromodifluoromethoxy)-2-(trifluoromethoxy)ethene;

(Z)-1-(bromodifluoromethoxy)-2-(trifluoromethoxy)ethene;

1,1,4,4,4-pentafluoro-1-bromo-2-butanone;

1,1,5,5,5-pentafluoro-1-bromo-3-pentanone;

3-bromo-2,3,3-trifluoropropene;

3-bromo-1,3,3-trifluoropropene; and

3-bromo-3,3-difluoro-1-propene.

4. The polymer coating application method of claim 3 , wherein the polymer coating is applied by one of spraying, dipping, and brushing.

5. A material blowing method comprising:

dissolving a suitable material for the blowing application in a solvent composition comprising

(1) a first compound selected from the group consisting of fluorinated alkanes, diones, heterocyclics, cycloalkanes, anhydrides, ketones, cycloalkenes, aromatics, acetates, ethers, esters, alcohols, and alkenes, and

(2) a second compound which contains one bromine atom and is selected from the group consisting of partially fluorinated aromatics, ketones, ethers, and alkenes,

wherein the first compound is selected from the group consisting of

1-chloro-2,2,2-trifluoroethyl difluoromethyl ether (isoflurane);

2-chloro-1,1,2-trifluoroethyl difluoromethyl ether (enflurane);

methyl 2,2,2-trifluroethyl-1-(trifluoromethyl)ether;

heptafluoropropyl 1,2,2,2-tetrafluoroethyl ether;

perfluorodibutyl ether;

3,3,3-trifluoro-bis-2,2-(trifluoromethyl)-1-propanol;

1,2-(Z)-bis(perfluoro-n-buty)ethylene;

1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)-2-propanol;

2H,3H-decafluoropentane (Vertrel XF);

ethyl-perfluorobutyl ether;

1,1,1,5,5,5-hexafluoro-2,4-pentanedione;

perfluoro-2-butyltetrahydrofuran;

1H,2H,4H-nonafluorocyclohexane;

1-methoxy-2-trifluoromethyl-1,3,3,3-tetrafluoro-1-propene;

fluoromethyl 2,2,2-trifluoro-1-(trifluoromethyl)ethyl ether (SEVOFLURANE);

(E)-2,3-dichlorohexafluoro-2-butene;

3,3-dichloro-1,1,1,2,2-pentafluoropropane (HCFC-225);

methyl-1,1,2,2,3,3-hexafluoropropyl ether;

trifluoroacetic anhydride;

2,2-difluoroethyl-1,1,2,2-tetrafluoroethyl ether;

1,3-dichloro-1,1,2,2,3-pentafluoropropane (HCFC-225cb, AK-225G);

bis(2,2,2-trifluoroethyl)ether;

methyl heptafluoropropyl ketone;

difluoromethyl-2,2,3,3-tetrafluoropropyl ether;

bis(difluoromethoxy)-tetrafluoroethane;

2-chloro-1,1,2-trifluoroethyl ethyl ether;

1-(2,2,2-trifluoroethoxy)nonafluoro-cyclohexene;

1,2-dichloro-3,3,4,4,5,5,6,6-octafluoro-cyclohexene;

ethyl-1,1,2,2-tetrafluoroethyl ether;

perfluorotoluene;

methyl trifluoroacetate;

methyl pentafluoropropanoate; and

1,2-dichloro-hexafluoro-cyclopentene, and

wherein the second compound is selected from the group consisting of

4-bromo-3-chloro-3,4,4-trifluoro-1-butene;

1-bromo-2-(trifluoromethyl)-3,3,3-trifluoropropene;

4-bromo-1,1,1,3,4,4-hexafluoro-2-(trifluoromethyl)-2-butene;

4-bromo-1,1,1,4,4-pentafluoro-2-(trifluoromethyl)-2-butene;

3-bromo-1,1,2,3,4,4,4-heptafluorobutene;

1,1,1,4,4-pentafluoro-4-bromo-2-trifluoromethyl-2-butene;

1-bromo-1,3,3,3-tetrafluoro-2-(trifluoromethyl)-1-propene;

(Z)-1-bromo-perfluoro-2-butene;

4-bromo-1,1,2,3,3,4,4-heptafluorobutene;

(Z)-2-bromo-1,1,1,3,4,4,4-heptafluoro-2-butene;

(E)-2-bromo-1,1,1,3,4,4,4-heptafluoro-2-butene;

(E)-1-bromo-perfluoro-2-butene;

(E)-2-bromo-1,1,1,4,4,4-hexafluoro-2-butene;

1-bromo-bis(perfluoromethyl) ethylene;

1-(bromodifluoromethoxy)-2-(trifluoromethyl)-1,3,3,3-tetrafluoro-1-propene;

2-bromo-3,3,4,4,4-pentafluorobutene;

3-bromo-2,3,4,4,4-pentafluorobutene;

4-bromo-2,3,3,4,4-pentafluorobutene;

(Z)-1-(bromodifluoromethoxy)-1,2,3,3,3-pentafluoro-1-propene;

3-bromo-3,3-difluoro-2-(trifluoromethyl)-propene;

(Z)-1-bromo-1,1,4,4,4-pentafluoro-2-butene;

(E)-1-(bromodifluoromethoxy)-1,2,3,3,3-pentafluoro-1-propene;

1-(bromodifluoromethoxy)-2-(trifluoromethyl)-3,3,3-trifluoro-1-propene;

2-bromo-1,1,2,2-tetrafluoroethoxy-trifluoroethene;

(E)-1-bromo-1,1,4,4,4-pentafluoro-2-butene;

4-bromo-3,3,4,4-tetrafluoro-1-butene;

(Z)-1-bromo-1,2-difluoro-2-(2,2,2-trifluoroethoxy)-ethene;

(bromodifluoromethyl)-pentafluorobenzene;

(Z)-1-(bromodifluoromethoxy)-2-(trifluoromethyl)ethane;

2-bromoheptafluorotoluene;

(2,2,2-trifluoroethyl)(2-bromo-2,2-difluoroethyl)ether;

3-bromoheptafluorotoluene;

4-bromoheptafluorotoluene;

1-(bromodifluoromethoxy)-1-(trifluoromethyl)ethene;

(E)-1-(bromodifluoromethoxy)-2-(trifluoromethyl)ethene;

1-bromo-2,4,6-tris(trifluoromethyl)benzene;

4-bromo-1,1,2,3,3-pentafluorobutene;

(E)-1-(bromodifluoromethoxy)-2-(trifluoromethoxy)ethene;

(Z)-1-(bromodifluoromethoxy)-2(trifluoromethoxy)ethene;

1,1,4,4,4-pentafluoro-1-bromo-2-butanone;

1,1,5,5,5-pentafluoro-1-bromo-3-pentanone;

3-bromo-2,3,3-trifluoropropene;

3-bromo-1,3,3-trifluoropropene; and

3-bromo-3,3-difluoro-1-propene.

6. The material blowing method of claim 5 , wherein the blowing application is foam blowing.

Continuity (2)
Division 11043091 · Jan 27, 2005
Related Publication 20090005282A1 · Jan 1, 2009