US3349039A - Cleaning composition - Google Patents

Cleaning composition Download PDF

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Publication number
US3349039A
US3349039A US288918A US28891863A US3349039A US 3349039 A US3349039 A US 3349039A US 288918 A US288918 A US 288918A US 28891863 A US28891863 A US 28891863A US 3349039 A US3349039 A US 3349039A
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Prior art keywords
cleaning
dry cleaning
trans
dichloroethylene
weight
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US288918A
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Renault Daniel Auguste M Henri
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Produits Chimiques Pechiney Saint Gobain
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Produits Chimiques Pechiney Saint Gobain
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Classifications

    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06L—DRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
    • D06L1/00—Dry-cleaning or washing fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods
    • D06L1/02—Dry-cleaning or washing fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods using organic solvents
    • D06L1/04—Dry-cleaning or washing fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods using organic solvents combined with specific additives
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/50—Solvents
    • C11D7/5004—Organic solvents
    • C11D7/5018—Halogenated solvents
    • C—CHEMISTRY; METALLURGY
    • C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23G—CLEANING OR DE-GREASING OF METALLIC MATERIAL BY CHEMICAL METHODS OTHER THAN ELECTROLYSIS
    • C23G5/00—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents
    • C23G5/02—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents using organic solvents
    • C23G5/028—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents using organic solvents containing halogenated hydrocarbons
    • C23G5/02806—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents using organic solvents containing halogenated hydrocarbons containing only chlorine as halogen atom
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06L—DRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
    • D06L1/00—Dry-cleaning or washing fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods
    • D06L1/02—Dry-cleaning or washing fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods using organic solvents
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/08—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with halogenated hydrocarbons

Definitions

  • This invention relates to a cleaning fluid formulated of organic chemical compounds and materials and it relates more particularly to a cleaning fluid for use in the dry cleaning of textiles formed of natural and/or synthetic fibers and in the cleaning of other materials and surfaces, such as parts formed of metal and the like materials.
  • a suitable dry cleaning fluid should embody a number of characteristics such as chemical stability, non-inflammability, easy and complete distillation for complete removal from the textile material and for solvent recovery, and non-toxicity. It should have high solvent power for the removal of grease, dirt and the like substances. It should have no effect on the textile fibers or other materials that are treated. It should be compatible with various additives usually employed in dry cleaning systems and the dry cleaning solvent should be low in cost.
  • the dry cleaning solvents which have been used in present practice include tetrachloroethylene and trichloroethylene. Because of the relatively high boiling points of these materials, complete removal of solvent in the drying step and in the deodorizing step consumes a considerable amount of time and thus adds undesirably to the length of the cleaning cycle which includes washing, wringing, drying, and deodorizing.
  • Dichloroethylene has a lower boiling point but it has been incapable of use to the present in dry cleaning because it is flammable, having a flash point at about 4 C.
  • trans-dichloroethylene in admixture to contain at least 15% by weight of one or more of the aforementioned compounds ethyl bromide, methylene chloride, or trichlorotrifiuoroethanes, and preferably an amount within the range of 15-30% by weight. Best results are secured with the combination of trans-dichloroethylene in admixture with about 20% by weight trifluoro-l,1,2-trichloro-1,2,2-ethane.
  • trans-dichloroethylene and trifluoro-l,1,2-trichloro-1,2,2-ethane is preferred because the tWo components have closely related boiling point ranges whereby they are capable of being distilled together to maintain their original ratio during distillation and redistillation or in the recovery of the solvent system.
  • the dry cleaning composition can be formulated to contain other substances in the form of additives such as are usually employed in dry cleaning systems, as represented by surface active agents, cleaning reinforcing agents, water, soaps, and the like, which additives are incorporated in the usual proportions, preferably in an amount less than 1% by weight.
  • additives such as are usually employed in dry cleaning systems, as represented by surface active agents, cleaning reinforcing agents, water, soaps, and the like, which additives are incorporated in the usual proportions, preferably in an amount less than 1% by weight.
  • the cleaning composition prepared in accordance with the practice of this invention also defines beneficial use as a solvent for cleaning or degreasing in general and particularly metals and insulation materials such as are employed in electric and telephone equipment, motors and the like.
  • Example 1 Composition: Percent by wt. Trans-dichloroethylene Trifluoro-l,1,2-trichloro-1,2,2-ethane 20 8 kg. of textile material, consisting of various garments formed of different types of fibers and highly soiled with greasy spots on wristbands, collars and buttonholes, were introduced into the dry cleaning machine.
  • the tank of the machine was filled with liters of the dry cleaning system described above and the cleaning process was carried out in accordance with known techniques consisting of the steps of washing, wringing, drying and deodorizing.
  • the temperature of the cleaning system was maintained at about 2023 C. and the washing step with the solvent was continued for about 7 minutes, followed by the steps of wringing, drying and deodorizing which consumed 3 and 6 minutes, respectively, to provide for a total cleaning cycle of 16 minutes.
  • the clothes removed from the washing machine were spotless and no greying was noticed on any of the garments.
  • Example 2 Composition: Parts by wt. Trans-dichloroethylene 80 Tirfluoro-l,1,2-trichloro-1,2,2-ethane 20 Liquid detergent (alkyl aryl sulfonate) marketed by Lever Brothers under the name Sactisol 0.1 Water 0.1
  • Example 2 The foregoing solvent system is employed in a cleaning cycle as describe din Example 1.
  • the cleaning composition of Example 2 is effective for the removal of water spots
  • the dry cleaning machine was loaded with 8 kg. of soiled garments of the following textile fibers, namely glycol polyterephthalate and wool (trousers), polyacrylonitrile (pull-over sweater), polyamide 6/6 (Anorak),
  • viscose artificial silk (bodice), glycol polyterephthalate (kilted skirts), wool (suits).
  • Remnants of the aforementioned textile materials in the form of strips have also been introduced for the purpose of verifying the dimensional stability as well as the mechanical resistance during cleaning.
  • the total cleaning cycle was as follows:
  • the garments removed from the washing machine were practically unaltered insofar as the textiles formed of natural fibers as well as synthetic fibers, and cleaning was complete.
  • Example 4 8570% by weight trans-dichloroethylene 1530% by weight of either ethyl bromide or methylene chloride or trifluorotrichloroethane, or mixtures thereof It will be aparent from the foregoing that we have provided a dry cleaning solvent system which is capable of more efiicient and effective use in the cleaning and dry cleaning processes by reason of maintaining the desirable characteristics heretofore specified [or a dry cleaning solvent While achieving marked reduction in the distillation temperature without increase in the inflammability of the resulting product.
  • a liquid cleaning composition consisting essentially lof a major portion of trans-dichloroethyleno and a minor portion of a compound selected from the group consisting of ethyl bromide, methylene chloride, and triiluorotrichloroethanes, said compound being present in admixture with the trans-dichloroethylene in an amount within the range of l5-30% by weight.
  • a liquid dry cleaning composition consisting essentially of a major portion of trans-dichlorocthylene. a minor portion of a compound selected from the group consisting of ethyl bromide, methylene chloride and trifiuorotrichloroethanes, said compound being present in an amount within the range of 15-30% by weight of the dry cleaning system and in which a surface active agent is present in an amount less than 1% by weight.
  • a liquid dry cleaning composition as claimed in claim 3 which includes water present in an amount less than 1% by weight.
  • a cleaning composition consisting essentially of a major portion of trans-dichloroethylene, about 20% by weight of trfiuoro-l,l,2-trichloro-l,2,2,-cthane, and less than 1% by weight of a surface active agent.

Description

United States Patent 3,349,039 CLEANING COMPQSITION Daniel Auguste Marie Henri Renault, Boulogne-sur-Seine,
France, assignor to Produits Chimiques Pechiney-Saint- Gobain, Neuilly-sur-Seine, France No Drawing. Filed June 19, 1963, Ser. No. 288,918 Claims priority, application France, June 26, 1962, 901,995 5 Claims. (Cl. 252-172) This invention relates to a cleaning fluid formulated of organic chemical compounds and materials and it relates more particularly to a cleaning fluid for use in the dry cleaning of textiles formed of natural and/or synthetic fibers and in the cleaning of other materials and surfaces, such as parts formed of metal and the like materials.
With reference particularly to a solvent system for use in dry cleaning of textile materials, a suitable dry cleaning fluid should embody a number of characteristics such as chemical stability, non-inflammability, easy and complete distillation for complete removal from the textile material and for solvent recovery, and non-toxicity. It should have high solvent power for the removal of grease, dirt and the like substances. It should have no effect on the textile fibers or other materials that are treated. It should be compatible with various additives usually employed in dry cleaning systems and the dry cleaning solvent should be low in cost.
The dry cleaning solvents which have been used in present practice include tetrachloroethylene and trichloroethylene. Because of the relatively high boiling points of these materials, complete removal of solvent in the drying step and in the deodorizing step consumes a considerable amount of time and thus adds undesirably to the length of the cleaning cycle which includes washing, wringing, drying, and deodorizing.
Dichloroethylene has a lower boiling point but it has been incapable of use to the present in dry cleaning because it is flammable, having a flash point at about 4 C.
It is an object of this invention to produce a dry cleaning solvent system which meets the desirable characteristics heretofore described and overcomes the deficiencies of solvent systems presently in use in that it has a much lower boiling point and is therefore more easily and quickly removed during the drying and deodorizing steps thereby materially to shorten the dry cleaning cycle, and it is a related object to produce a new and improved cleaning fluid system which not only finds beneficial use in the dry cleaning of textile materials but which can also be used advantageously in the cleaning of metal and other surfaces for the removal of grease, dirt and the like.
It is an object of this invention to produce a dry cleaning process which includes the steps of washing the textile material with a liquid cleaning composition containing as its major ingredient trans-dichloroethylene whereby the solvent system can be more easily and quickly removed from the textile material and which is formulated to contain as a minor ingredient a component selected from the group consisting of ethyl bromide, methylene chloride, and trifluorotrichloroethane whereby the system is rendered non-inflammable and ceases to have a flash point, and it is a related object to produce a liquid dry cleaning composition of the type described.
It has been found that the desired objectives are achieved to produce a non-flammable dry cleaning system which is stable, easily distilled, inert to textile fibers, and of low cost when the system is formulated of trans-dichloroethylene in admixture to contain at least 15% by weight of one or more of the aforementioned compounds ethyl bromide, methylene chloride, or trichlorotrifiuoroethanes, and preferably an amount within the range of 15-30% by weight. Best results are secured with the combination of trans-dichloroethylene in admixture with about 20% by weight trifluoro-l,1,2-trichloro-1,2,2-ethane.
The combination of trans-dichloroethylene and trifluoro-l,1,2-trichloro-1,2,2-ethane is preferred because the tWo components have closely related boiling point ranges whereby they are capable of being distilled together to maintain their original ratio during distillation and redistillation or in the recovery of the solvent system.
In accordance with the practice of this invention, the dry cleaning composition can be formulated to contain other substances in the form of additives such as are usually employed in dry cleaning systems, as represented by surface active agents, cleaning reinforcing agents, water, soaps, and the like, which additives are incorporated in the usual proportions, preferably in an amount less than 1% by weight. The cleaning composition prepared in accordance with the practice of this invention also defines beneficial use as a solvent for cleaning or degreasing in general and particularly metals and insulation materials such as are employed in electric and telephone equipment, motors and the like.
The following examples are given by way of illustration, but not by way of limitation, of this invention:
Example 1 Composition: Percent by wt. Trans-dichloroethylene Trifluoro-l,1,2-trichloro-1,2,2-ethane 20 8 kg. of textile material, consisting of various garments formed of different types of fibers and highly soiled with greasy spots on wristbands, collars and buttonholes, were introduced into the dry cleaning machine. The tank of the machine was filled with liters of the dry cleaning system described above and the cleaning process was carried out in accordance with known techniques consisting of the steps of washing, wringing, drying and deodorizing.
The temperature of the cleaning system was maintained at about 2023 C. and the washing step with the solvent was continued for about 7 minutes, followed by the steps of wringing, drying and deodorizing which consumed 3 and 6 minutes, respectively, to provide for a total cleaning cycle of 16 minutes.
The clothes removed from the washing machine were spotless and no greying was noticed on any of the garments.
Example 2 Composition: Parts by wt. Trans-dichloroethylene 80 Tirfluoro-l,1,2-trichloro-1,2,2-ethane 20 Liquid detergent (alkyl aryl sulfonate) marketed by Lever Brothers under the name Sactisol 0.1 Water 0.1
The foregoing solvent system is employed in a cleaning cycle as describe din Example 1. In addition to the results secured in Example 1, the cleaning composition of Example 2 is effective for the removal of water spots To illustrate the ability to dry clean textiles formed of the various synthetic polymeric fibers as well as natural fibers, the dry cleaning machine was loaded with 8 kg. of soiled garments of the following textile fibers, namely glycol polyterephthalate and wool (trousers), polyacrylonitrile (pull-over sweater), polyamide 6/6 (Anorak),
viscose artificial silk (bodice), glycol polyterephthalate (kilted skirts), wool (suits).
Remnants of the aforementioned textile materials in the form of strips have also been introduced for the purpose of verifying the dimensional stability as well as the mechanical resistance during cleaning.
The total cleaning cycle was as follows:
About 7 minutes for washing with the temperature of the washing bath at about 2023 0;
About 3 minutes for wringing;
About 4 minutes for drying and deodorizing.
This provides for a total dry cleaning cycle of about 14 minutes.
The garments removed from the washing machine were practically unaltered insofar as the textiles formed of natural fibers as well as synthetic fibers, and cleaning was complete. The dimensional stability tests, completed by mechanical resistance tests carried out with an eclatomer and dynamometer, showed no noticeable change compared with tests carried out on samples having the same fiber composition but which were not submitted to the action of the cleaning system.
The procedures of Examples 1, 2 and 3 can be precticed with the following composition:
Example 4 8570% by weight trans-dichloroethylene 1530% by weight of either ethyl bromide or methylene chloride or trifluorotrichloroethane, or mixtures thereof It will be aparent from the foregoing that we have provided a dry cleaning solvent system which is capable of more efiicient and effective use in the cleaning and dry cleaning processes by reason of maintaining the desirable characteristics heretofore specified [or a dry cleaning solvent While achieving marked reduction in the distillation temperature without increase in the inflammability of the resulting product.
It will be understood that changes may be made in the details of formulation and use without departing from the spirit of the invention, especially as defined in the following claims.
I claim:
1. A liquid cleaning composition consisting essentially lof a major portion of trans-dichloroethyleno and a minor portion of a compound selected from the group consisting of ethyl bromide, methylene chloride, and triiluorotrichloroethanes, said compound being present in admixture with the trans-dichloroethylene in an amount within the range of l5-30% by weight.
2. A liquid cleaning composition as claimed in claim 1 in which the compound present in admixture with the trans-dichloroethylene is tritluoro-l,l.2-trichloro-l1,2,- ethane present in an amount of about 20% by weight.
3. A liquid dry cleaning composition consisting essentially of a major portion of trans-dichlorocthylene. a minor portion of a compound selected from the group consisting of ethyl bromide, methylene chloride and trifiuorotrichloroethanes, said compound being present in an amount within the range of 15-30% by weight of the dry cleaning system and in which a surface active agent is present in an amount less than 1% by weight.
4. A liquid dry cleaning composition as claimed in claim 3 which includes water present in an amount less than 1% by weight.
5. A cleaning composition consisting essentially of a major portion of trans-dichloroethylene, about 20% by weight of trfiuoro-l,l,2-trichloro-l,2,2,-cthane, and less than 1% by weight of a surface active agent.
References Cited UNITED STATES PATENTS 1,979,399 11/1934 Morgan 252-39 2,388,962 11/1945 Flett 252-l6l 2,947,792 8/1960 Skeeters 260652.5
3,042,479 7/1962 Hicks et al. 25217l X OTHER REFERENCES Mellan: Industrial Solvents (2nd edition) (1950) Rcinhold Pub. Corp., New York (pp. 332-334 relied on).
Hackhs Chemical Dictionary (third edition) (1944). The Blakiston Company, Pa. (page 269 relied on).
LEON D. ROSDOL, Primary Examiner.
JULIUS GREENWALD, Examiner.
I. T. FEDIGAN, \V. E. SCHULZ, Assistant Errmziuwxr.

Claims (1)

1. A LIQUID CLEANING COMPOSITION CONSISTING ESSENTIALLY OF A MAJOR PORTION OF TRANS-DICHLOROETHYLENE AND A MINOR PORTION OF A COMPOUND SELECTED FROM THE GROUP CONSISTING OF ETHYL BROMIDE, METHYLENE CHLORIDE, AND TRIFLUOROTRICHOLROETHANES, SAID COMPOUND BEING PRESENT IN ADMIXTURE WITH THE TRANS-DICHLOROETHYLENE IN AN AMOUNT WITHIN THE RANGE OF 15-30% BY WEIGHT.
US288918A 1962-06-26 1963-06-19 Cleaning composition Expired - Lifetime US3349039A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR901995A FR1334439A (en) 1962-06-26 1962-06-26 New dry cleaning solvent

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BE (1) BE633999A (en)
DE (1) DE1244706B (en)
FR (1) FR1334439A (en)
GB (1) GB1020833A (en)
LU (1) LU43952A1 (en)
NL (1) NL294460A (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3455835A (en) * 1966-04-12 1969-07-15 Du Pont Azeotropic composition
US4767561A (en) * 1987-09-23 1988-08-30 E. I. Du Pont De Nemours And Company Azeotrope or azeotrope-like composition of trichlorotrifluoroethane, methanol and 1,2-dichloroethylene
US4804493A (en) * 1988-05-24 1989-02-14 E. I. Du Pont De Nemours And Company Stabilized azeotrope or azeotrope-like composition of 1,1,2-trichloro-1,2,2-trifluoroethane and trans-1,2-dichloroethylene
US4808331A (en) * 1988-05-24 1989-02-28 E. I. Du Pont De Nemours And Company Azeotrope or azeotrope-like composition of 1,1,2,-trichloro-1,2,2-trifluoroethane, trans-1,2-dichloroethylene and cyclopentane
FR2882358A1 (en) * 2005-02-23 2006-08-25 Arkema Sa Composition, useful e.g. as foaming agent to manufacture thermoplastic polymer foams, comprises trans-1,2-dichloroethylene, 1,1,1,3,3-pentafluoropropane and 1,1,1,2-tetrafluoroethane

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1375734A (en) * 1963-05-20 1964-10-23 Pechiney Saint Gobain Dry cleaning agent
DE1289231B (en) * 1968-01-24 1969-02-13 Kali Chemie Ag Preparations for cleaning, in particular for magnetic recording systems and electrical equipment

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1979399A (en) * 1933-06-08 1934-11-06 Ralph A Morgen Dry cleaning process
US2388962A (en) * 1938-01-24 1945-11-13 Allied Chem & Dye Corp Dry cleaning composition
US2947792A (en) * 1954-02-16 1960-08-02 Diamond Alkali Co Stabilization of tetrachloroethylene with a mixture of a hydroxy alkyne and isoeugenol
US3042479A (en) * 1960-11-29 1962-07-03 Du Pont Chlorofluorohydrocarbons in dry cleaning compositions and process

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1979399A (en) * 1933-06-08 1934-11-06 Ralph A Morgen Dry cleaning process
US2388962A (en) * 1938-01-24 1945-11-13 Allied Chem & Dye Corp Dry cleaning composition
US2947792A (en) * 1954-02-16 1960-08-02 Diamond Alkali Co Stabilization of tetrachloroethylene with a mixture of a hydroxy alkyne and isoeugenol
US3042479A (en) * 1960-11-29 1962-07-03 Du Pont Chlorofluorohydrocarbons in dry cleaning compositions and process

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3455835A (en) * 1966-04-12 1969-07-15 Du Pont Azeotropic composition
US4767561A (en) * 1987-09-23 1988-08-30 E. I. Du Pont De Nemours And Company Azeotrope or azeotrope-like composition of trichlorotrifluoroethane, methanol and 1,2-dichloroethylene
US4804493A (en) * 1988-05-24 1989-02-14 E. I. Du Pont De Nemours And Company Stabilized azeotrope or azeotrope-like composition of 1,1,2-trichloro-1,2,2-trifluoroethane and trans-1,2-dichloroethylene
US4808331A (en) * 1988-05-24 1989-02-28 E. I. Du Pont De Nemours And Company Azeotrope or azeotrope-like composition of 1,1,2,-trichloro-1,2,2-trifluoroethane, trans-1,2-dichloroethylene and cyclopentane
FR2882358A1 (en) * 2005-02-23 2006-08-25 Arkema Sa Composition, useful e.g. as foaming agent to manufacture thermoplastic polymer foams, comprises trans-1,2-dichloroethylene, 1,1,1,3,3-pentafluoropropane and 1,1,1,2-tetrafluoroethane
WO2006090042A1 (en) * 2005-02-23 2006-08-31 Arkema France Trans-1,2 dichloroethylene composition
US20080306175A1 (en) * 2005-02-23 2008-12-11 Arkema France Trans-1,2 Dichloroethylene Composition
US20100056658A1 (en) * 2005-02-23 2010-03-04 Arkema France Trans-1,2 dichloroethylene composition
US7875657B2 (en) 2005-02-23 2011-01-25 Arkema France Trans-1,2 dichloroethylene composition

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FR1334439A (en) 1963-08-09
GB1020833A (en) 1966-02-23
LU43952A1 (en) 1963-12-22
NL294460A (en)
DE1244706B (en) 1967-07-20
BE633999A (en)

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