US3723331A - Stabilization of saturated halogenated aliphatic hydrocarbons - Google Patents
Stabilization of saturated halogenated aliphatic hydrocarbons Download PDFInfo
- Publication number
- US3723331A US3723331A US00120739A US3723331DA US3723331A US 3723331 A US3723331 A US 3723331A US 00120739 A US00120739 A US 00120739A US 3723331D A US3723331D A US 3723331DA US 3723331 A US3723331 A US 3723331A
- Authority
- US
- United States
- Prior art keywords
- percent
- weight
- trioxane
- amount
- range
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 229920006395 saturated elastomer Polymers 0.000 title claims description 18
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 title claims description 15
- 230000006641 stabilisation Effects 0.000 title description 15
- 238000011105 stabilization Methods 0.000 title description 15
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 claims abstract description 27
- 238000000034 method Methods 0.000 claims abstract description 18
- 239000002904 solvent Substances 0.000 claims abstract description 14
- 150000002118 epoxides Chemical class 0.000 claims abstract description 13
- 239000007788 liquid Substances 0.000 claims abstract description 12
- -1 alkyl nitrile Chemical class 0.000 claims description 22
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 17
- 125000004971 nitroalkyl group Chemical group 0.000 claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 7
- 238000009835 boiling Methods 0.000 claims description 7
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical class CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 claims description 6
- ZDUOUNIIAGIPSD-UHFFFAOYSA-N 1,1,1-tribromoethane Chemical class CC(Br)(Br)Br ZDUOUNIIAGIPSD-UHFFFAOYSA-N 0.000 claims description 5
- KNKRKFALVUDBJE-UHFFFAOYSA-N 1,2-dichloropropane Chemical class CC(Cl)CCl KNKRKFALVUDBJE-UHFFFAOYSA-N 0.000 claims description 5
- 150000008282 halocarbons Chemical class 0.000 claims description 5
- QVLAWKAXOMEXPM-UHFFFAOYSA-N 1,1,1,2-tetrachloroethane Chemical class ClCC(Cl)(Cl)Cl QVLAWKAXOMEXPM-UHFFFAOYSA-N 0.000 claims description 4
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical class CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 4
- XFNJYAKDBJUJAJ-UHFFFAOYSA-N 1,2-dibromopropane Chemical compound CC(Br)CBr XFNJYAKDBJUJAJ-UHFFFAOYSA-N 0.000 claims description 4
- RMISVOPUIFJTEO-UHFFFAOYSA-N 2,3-dichlorobutane Chemical class CC(Cl)C(C)Cl RMISVOPUIFJTEO-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- LYGJENNIWJXYER-BJUDXGSMSA-N nitromethane Chemical group [11CH3][N+]([O-])=O LYGJENNIWJXYER-BJUDXGSMSA-N 0.000 claims description 4
- 125000006676 (C1-C4) aliphatic hydrocarbon group Chemical group 0.000 claims 1
- 230000000087 stabilizing effect Effects 0.000 abstract description 8
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 abstract description 5
- 125000001931 aliphatic group Chemical group 0.000 abstract description 4
- 229930195734 saturated hydrocarbon Natural products 0.000 abstract description 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 14
- 239000003381 stabilizer Substances 0.000 description 8
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 239000004519 grease Substances 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- NALZTFARIYUCBY-UHFFFAOYSA-N 1-nitrobutane Chemical compound CCCC[N+]([O-])=O NALZTFARIYUCBY-UHFFFAOYSA-N 0.000 description 1
- JSZOAYXJRCEYSX-UHFFFAOYSA-N 1-nitropropane Chemical compound CCC[N+]([O-])=O JSZOAYXJRCEYSX-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000013844 butane Nutrition 0.000 description 1
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000005238 degreasing Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- MPAYEWNVIPXRDP-UHFFFAOYSA-N ethanimine Chemical compound CC=N MPAYEWNVIPXRDP-UHFFFAOYSA-N 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000004658 ketimines Chemical class 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical class CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 1
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
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
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/38—Separation; Purification; Stabilisation; Use of additives
- C07C17/42—Use of additives, e.g. for stabilisation
-
- 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
- C23G5/02854—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 characterised by the stabilising or corrosion inhibiting additives
- C23G5/02861—Oxygen-containing compounds
- C23G5/02877—Ethers
Definitions
- the present invention relates to the stabilization of halogenated aliphatic hydrocarbons saturated in C, to C, and particularly trichloro-l ,1 ,l ethane.
- trioxane it is also known to use trioxane as a stabilizer.
- the interval of stabilization time preceding the appearance 'of acid vapors or of a coloration varies from only minutes to 48 hours, which is insufficient for the prolonged use of trichloro-l,1,l ethane in degreasing or cleaning of metal or other objects.
- the objective of this invention is to remedy the inconvenience cited above by allowing efficient and prolonged stabilization of the aliphatic halogenated hydrocarbons and thus the carrying out of the grease removal and/or cleaning of metal parts, plastics, textile or other materials, without noticing any degradation of the solvent and of the materials to be treated.
- the stabilization of the aliphatic saturated halogenated solvents in C, to C, and particularly of trichloro-l,l,l ethane is accomplished by incorporating therein trioxane associated with an aliphatic alcohol, particularly tertio butanol and/or an epoxide which is liquid at ordinary temperature, particularly butylene oxide.
- trioxane is associated with from 0.1 to 7.5 percent of said aliphatic alcohol and/or from 0.1 to 4 percent of said epoxide.
- the combination is then incorporated into the halogenated solvent.
- thiol such as alkyl orthoformate, alkyl orthoacetate, aliphatic or cyclic acetal, aliphatic organic acid
- imino-ether such as N-alkyl alkoxy-l ethanimine and ketimine such as N- alkyl isopropanimine
- an oxygen containing heterocyclic nucleus such as pyrannic heterocycle and/or a nitrogen containing heterocyclic nucleus such as pyrrolic, pyrrolinic and morpholinic heterocycle
- the aforementioned alkyl groupings have from one to four carbon atoms and the boiling points of the compounds associated with trioxane and used in the stabilization formulas should not differ by more than 50, and preferably by not more than 25 C, from the boiling point of the halogenated saturated aliphatic hydrocarbon in question.
- the foregoing materials may be associated with the trioxane in an amount within the range of 0.1 to 4 percent by weight and preferably in an amount within the range of 0.3 to 2 percent by weight, based upon the solvent composition.
- the following list of compounds may be cited, but this list cannot be considered as limiting: dichloroethanes, trichloroethanes, and particularly trichloro-l, 1,1 ethane, tetrachloroethanes, dichloro-1,2 propane, dichloro-l,2 and -2,3 butanes, tribromo ethanes and dibromo-l ,2-propane.
- the invention relates also to the stabilized compounds comprising one or several halogenated saturated aliphatic hydrocarbons in C, to C,, particularly trichloro-l,l ,1 ethane containing from 0.001 to 15 percent by weight of trioxane associated with 0.1 to 7.5 percent by weight of an aliphatic alcohol, particularly tertio butanol, and/or with 0.1 to 4 percent by weight of an expoxide liquid at ordinary temperature, particularly butylene oxide.
- These compounds may also contain an alkyl nitrile in C, to C,, such as acetonitrile, propionitrile and butyronitrile, in an amount within the range of 0.1 to 4 percent by weight and preferably 0.3 to 2 percent by weight, and/or nitroalkane in C, to C,, such as nitromethane, nitroethane, nitropropane, and nitrobutane, in an amount within the range of 0.1 to 4 percent by weight and preferably 0.3 to 2 percent by weight.
- an alkyl nitrile in C, to C such as acetonitrile, propionitrile and butyronitrile
- nitroalkane in C, to C, such as nitromethane, nitroethane, nitropropane, and nitrobutane
- 40 ml trichloro-1,l,l ethane are placed in a reflux condenser along with the stabilizer in the form of an aluminum plate of 99.9 percent purity, 1 mm thick, mm long and 12 mm wide. This plate is partly immersed into the trichloro-l,l,l ethane.
- the heating time in the reflux condenser preceding the release of acid vapors and/or the buildup of a coloration of trichloro-l ,l ,1 ethane indicates the stabilization aptitude of the tested stabilizer combination.
- compositions were prepared with 1,1,l-trichloroethane containing the components as set forth in the following table and the compositions were submitted to tests for stabilization as in Example 4.
- a method for stabilizing halogenated saturated aliphatic hydrocarbon solvents having from one to four carbon atoms comprising the steps of forming a combination consisting essentially of trioxane, associated with at least one member selected from the group consisting of a lower alcohol and a liquid epoxide and adding said combination to the hydrocarbon, wherein 0.001 to 15 percent by weight of trioxane is associated with from 0.1 to 7.5 percent by weight of the alcohol when present and 0.1 to 4 percent by weight of the liquid epoxide when present.
- halogenated hydrocarbon is selected from the group consisting of dichloroethanes, trichloroethanes, tetrachloroethanes, 1,2-dichloropropanes, 1,2-dichloro and 2,3-dichlorobutanes, tribromoethanes and 1,2- dibromopropane.
- a stabilized composition consisting essentially of a halogenated saturated aliphatic hydrocarbon having from one to four carbon atoms containing from 0.001 to 15 percent by weight of trioxane and at least one member comprising from 0.1 to 7.5 percent by weight of a lower alcohol and from 0.1 to 4 percent by weight of a liquid epoxide.
- composition as claimed in claim 9 containing in addition a compound selected from the group consisting of a C, to C, alkyl nitrile and a C, to C nitroalkane in which the compound is present in an amount within the range of 0.1 to 4 percent by weight.
- composition asclaimed in claim in which the alkyl nitrile is acetonitrile and the nitroalkane is nitromethane.
- a stabilized composition consisting essentially of a halogenated saturated C to C aliphatic hydrocarbon solvent stabilized with trioxane present in an amount within the range of 0.001 to l5 percent by weight, at least one of the members selected from the group consisting of a lower alcohol and a liquid epoxide and mixtures thereof in which the alcohol is present in an amount within the range of 0.1 to 7.5 percent by weight when present, and the liquid epoxide is present in an amount within the range of 0.1 to 4 percent by weight when present, and at least one compound selected from the group consisting of a C to C alkyl nitrile'and a C 1,2-dichloropropanes, 1,2-dichloro and 2,3- dichlorobutanes, tribromoethanes and 1,2- dibromopropane.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Materials Engineering (AREA)
- Mechanical Engineering (AREA)
- Metallurgy (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Detergent Compositions (AREA)
- Cleaning And De-Greasing Of Metallic Materials By Chemical Methods (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR128693 | 1967-11-17 | ||
| US12073971A | 1971-03-03 | 1971-03-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3723331A true US3723331A (en) | 1973-03-27 |
Family
ID=26180925
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US00120739A Expired - Lifetime US3723331A (en) | 1967-11-17 | 1971-03-03 | Stabilization of saturated halogenated aliphatic hydrocarbons |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3723331A (enrdf_load_stackoverflow) |
| BE (1) | BE719662A (enrdf_load_stackoverflow) |
| CH (1) | CH489448A (enrdf_load_stackoverflow) |
| DE (1) | DE1793235C3 (enrdf_load_stackoverflow) |
| FR (1) | FR1567940A (enrdf_load_stackoverflow) |
| GB (1) | GB1198583A (enrdf_load_stackoverflow) |
| NL (1) | NL159647B (enrdf_load_stackoverflow) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3864413A (en) * | 1970-01-22 | 1975-02-04 | Norman L Beckers | Stabilized metal chloroform |
| US4018837A (en) * | 1972-08-16 | 1977-04-19 | The Dow Chemical Company | Stabilized methylchloroform |
| US4324757A (en) * | 1979-07-02 | 1982-04-13 | The Dow Chemical Company | Halogenated hydrocarbons inhibited against denickelification with lower alkylcyanide compounds |
| US4973420A (en) * | 1989-05-04 | 1990-11-27 | Hoechst Celanese Corporation | Stripper composition for removal of protective coatings |
| US6010997A (en) * | 1998-06-25 | 2000-01-04 | Alliedsignal Inc. | Compositions of 1-bromopropane, nitromethane or acetonitrile and an alcohol |
| US6048832A (en) * | 1998-06-25 | 2000-04-11 | Alliedsignal Inc. | Compositions of 1-bromopropane, 4-methoxy-1,1,1,2,2,3,3,4,4-nonafluorobutane and an organic solvent |
| US6103684A (en) * | 1998-06-25 | 2000-08-15 | Alliedsignal Inc. | Compositions of 1-bromopropane and an organic solvent |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3694368A (en) * | 1971-02-26 | 1972-09-26 | Allied Chem | Ternary azeotropic compositions |
| FR2437392A1 (fr) * | 1978-06-30 | 1980-04-25 | Rhone Poulenc Ind | Stabilisation du trichloro-1,1,1 ethane |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3251891A (en) * | 1962-01-18 | 1966-05-17 | Pittsburgh Plate Glass Co | Stabilized compositions |
| US3326988A (en) * | 1964-07-13 | 1967-06-20 | Pittsburgh Plate Glass Co | Stabilized methyl chloroform compositions with improved evaporation characteristics |
| US3564061A (en) * | 1965-08-17 | 1971-02-16 | Pechiney Saint Gobain | Stabilization of halogenated solvents |
| US3564063A (en) * | 1958-02-03 | 1971-02-16 | Ppg Industries Inc | Stabilized methylchloroform compositions |
-
1967
- 1967-11-17 FR FR128693A patent/FR1567940A/fr not_active Expired
-
1968
- 1968-08-16 CH CH1234568A patent/CH489448A/fr not_active IP Right Cessation
- 1968-08-19 BE BE719662D patent/BE719662A/xx not_active IP Right Cessation
- 1968-08-20 DE DE1793235A patent/DE1793235C3/de not_active Expired
- 1968-08-20 NL NL6811831.A patent/NL159647B/xx not_active IP Right Cessation
- 1968-08-20 GB GB39831/68A patent/GB1198583A/en not_active Expired
-
1971
- 1971-03-03 US US00120739A patent/US3723331A/en not_active Expired - Lifetime
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3564063A (en) * | 1958-02-03 | 1971-02-16 | Ppg Industries Inc | Stabilized methylchloroform compositions |
| US3251891A (en) * | 1962-01-18 | 1966-05-17 | Pittsburgh Plate Glass Co | Stabilized compositions |
| US3326988A (en) * | 1964-07-13 | 1967-06-20 | Pittsburgh Plate Glass Co | Stabilized methyl chloroform compositions with improved evaporation characteristics |
| US3564061A (en) * | 1965-08-17 | 1971-02-16 | Pechiney Saint Gobain | Stabilization of halogenated solvents |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3864413A (en) * | 1970-01-22 | 1975-02-04 | Norman L Beckers | Stabilized metal chloroform |
| US4018837A (en) * | 1972-08-16 | 1977-04-19 | The Dow Chemical Company | Stabilized methylchloroform |
| US4324757A (en) * | 1979-07-02 | 1982-04-13 | The Dow Chemical Company | Halogenated hydrocarbons inhibited against denickelification with lower alkylcyanide compounds |
| US4973420A (en) * | 1989-05-04 | 1990-11-27 | Hoechst Celanese Corporation | Stripper composition for removal of protective coatings |
| US6010997A (en) * | 1998-06-25 | 2000-01-04 | Alliedsignal Inc. | Compositions of 1-bromopropane, nitromethane or acetonitrile and an alcohol |
| US6048832A (en) * | 1998-06-25 | 2000-04-11 | Alliedsignal Inc. | Compositions of 1-bromopropane, 4-methoxy-1,1,1,2,2,3,3,4,4-nonafluorobutane and an organic solvent |
| US6103684A (en) * | 1998-06-25 | 2000-08-15 | Alliedsignal Inc. | Compositions of 1-bromopropane and an organic solvent |
| US6365565B1 (en) | 1998-06-25 | 2002-04-02 | Honeywell International Inc. | Compositions of 1-bromopropane and an organic solvent |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1198583A (en) | 1970-07-15 |
| CH489448A (fr) | 1970-04-30 |
| BE719662A (enrdf_load_stackoverflow) | 1969-02-19 |
| DE1793235A1 (de) | 1971-12-16 |
| NL6811831A (enrdf_load_stackoverflow) | 1969-05-20 |
| FR1567940A (enrdf_load_stackoverflow) | 1969-05-23 |
| DE1793235B2 (de) | 1979-02-15 |
| DE1793235C3 (de) | 1979-10-04 |
| NL159647B (nl) | 1979-03-15 |
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