US3049571A - Stabilized degreasing solvent - Google Patents
Stabilized degreasing solvent Download PDFInfo
- Publication number
- US3049571A US3049571A US15821A US1582160A US3049571A US 3049571 A US3049571 A US 3049571A US 15821 A US15821 A US 15821A US 1582160 A US1582160 A US 1582160A US 3049571 A US3049571 A US 3049571A
- Authority
- US
- United States
- Prior art keywords
- methyl chloroform
- solvent
- zinc
- percent
- dioxane
- 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
- 239000002904 solvent Substances 0.000 title description 33
- 238000005238 degreasing Methods 0.000 title description 11
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 claims description 45
- 230000000087 stabilizing effect Effects 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 18
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 17
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 26
- 229910052725 zinc Inorganic materials 0.000 description 26
- 239000011701 zinc Substances 0.000 description 26
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 16
- 229910052751 metal Inorganic materials 0.000 description 16
- 239000002184 metal Substances 0.000 description 16
- 238000000354 decomposition reaction Methods 0.000 description 14
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 239000003112 inhibitor Substances 0.000 description 9
- 229910052742 iron Inorganic materials 0.000 description 8
- 150000002739 metals Chemical class 0.000 description 8
- 239000003381 stabilizer Substances 0.000 description 8
- 229910052782 aluminium Inorganic materials 0.000 description 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 7
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 7
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical group CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 230000007797 corrosion Effects 0.000 description 4
- 238000005260 corrosion Methods 0.000 description 4
- 150000002924 oxiranes Chemical group 0.000 description 4
- WHNBDXQTMPYBAT-UHFFFAOYSA-N 2-butyloxirane Chemical compound CCCCC1CO1 WHNBDXQTMPYBAT-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 230000015556 catabolic process Effects 0.000 description 3
- 238000006731 degradation reaction Methods 0.000 description 3
- -1 iron and aluminum Chemical class 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 229910001297 Zn alloy Inorganic materials 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- QMMOXUPEWRXHJS-HYXAFXHYSA-N (z)-pent-2-ene Chemical compound CC\C=C/C QMMOXUPEWRXHJS-HYXAFXHYSA-N 0.000 description 1
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 1
- SYQIWVMFOAHDMK-UHFFFAOYSA-N 2,2,3,3-tetramethyloxirane Chemical compound CC1(C)OC1(C)C SYQIWVMFOAHDMK-UHFFFAOYSA-N 0.000 description 1
- GELKGHVAFRCJNA-UHFFFAOYSA-N 2,2-Dimethyloxirane Chemical compound CC1(C)CO1 GELKGHVAFRCJNA-UHFFFAOYSA-N 0.000 description 1
- DJQGARJHMZLWPJ-UHFFFAOYSA-N 6-oxabicyclo[3.1.0]hex-1(5)-ene Chemical compound C1CCC2=C1O2 DJQGARJHMZLWPJ-UHFFFAOYSA-N 0.000 description 1
- 229910001369 Brass Inorganic materials 0.000 description 1
- GXBYFVGCMPJVJX-UHFFFAOYSA-N Epoxybutene Chemical compound C=CC1CO1 GXBYFVGCMPJVJX-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 241001474728 Satyrodes eurydice Species 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 239000010951 brass Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000005108 dry cleaning Methods 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000009972 noncorrosive effect Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
Classifications
-
- 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
- C23G5/0288—Epoxy compounds
-
- 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
Definitions
- This invention relates to a solvent comprising methyl chloroform containing a mixture of inhibitors effective to prevent decomposition of the methyl chloroform when the vapors thereof are in contact with metallic zinc surfaces and to prevent corrosion of the zinc and zinc alloys.
- Methyl chloroform is recognized as an excellent solvent and there has been a continuing need to render it inert to the presence of metals under the conditions of vapor degreasing.
- Stabilizers are known which are effective in stabilizing methyl chloroform against decomposition induced by contact with iron and aluminum even at elevated temperatures. It is now known, however, that while pure uninhibited methyl chloroform at elevated temperatures is relatively inert to the presence of zinc, methyl chloroform which is stabilized against decomposition due to contact with other metals, particularly iron and aluminum, tends to decompose badly in the presence of zinc and cause substantial corrosive attack on the Zinc metal.
- Methyl chloroform may be used in the cold degreasing of metals until it becomes saturated with dirt, grease and other impurities from the metal being cleaned.
- Spent solvent without the stabilizer system hereinafter proposed cannot be recovered by distillation in the zinc-lined stills commonly used in the industry without damage to the lining thereof.
- Methyl chloroform where used as a vapor degreasing solvent contains minor amounts of certain additives or stabilizers to prevent decomposition of the solvent induced by its contact with metals such as aluminum and iron.
- Inhibitors such as 1,4-di0xane alone or in combination with nitromethane, secondary butyl alcohol, or monohydric acetylenic alcohols are commonly employed.
- stabilizers are quite effective in rendering the solvent inert to attack of the metal by the degradation products, but greatly increase the ability of zinc, in the boiling solvent vapors, to cause degradation of the solvent and concomitantly increased attack of the metal.
- This undesirable property of the solvent may be eliminated, however, by the addition thereto of a vicinal inonoepoxide in the amount of from about 0.01 to 5.0 percent by Weight of the solvent mixture. It is preferred to employ the epoxide in the amount of from about 0.10 to 1.5 percent by Weight, however. If an amount less than 0.01 percent is employed no effective stabilization is achieved. Amounts greater than 5 percent may be employed but no advantage is achieved thereby.
- Vicinal epoxides refers to aliphatic epoxides containing an ethylene oxide group. While many vicinal monoepoxides are operable to some extent it is desirable to employ vicinal monoepoxides containing from 4 to 6 carbon atoms, for example, 1,2-butylene oxide, isobutylene oxide, cis-2,3- and trans-2,3-butylene oxide, 3,4- epoxybutene transand cis-2,3-pentene oxide, Z-methyl- 2,3-epoxybutane, 1,2-epoxycyclopentene and 2,3-dimethyl2,3epoxybutane.
- 1,2-butylene oxide isobutylene oxide
- cis-2,3- and trans-2,3-butylene oxide 3,4- epoxybutene transand cis-2,3-pentene oxide
- Z-methyl- 2,3-epoxybutane 1,2-epoxycyclopentene and 2,3-dimethyl2,3ep
- Example 1 To demonstrate the relative stability of uninhibited methyl chloroform to zinc a test run was made as follows:
- a flask was partly filled with uninhibited methyl chloformed due to decomposition of the solvent and ZnCl formed by corrosive action of the solvent on the zinc.
- Example 2 In the same equipment, and under the same conditions employed in Example 1, a sample (1) of methyl chloroform containing 4 percent by Weight of 1,4-dioxane, a sample (2) of methyl chloroform containing 4 percent by weight of 1,4-dioxane and 0.05 percent by weight of secondary butyl alcohol and a sample (3) of methyl chloroform containing 4 percent by weight of 1,4-dioxane and 0.5 percent by weight of nitromethane were boiled for seven days. The test strips in every case were found to be badly corroded. The methyl chloroform, sample (1) was found to contain 110 p.p.m. chloride, sample (2) Was found to contain 150 p.p.m. chloride, and sample (3) was found to contain p.p.m. chloride. However, the zinc strips in sample (3) were corroded more severely than in the other two test strips.
- Example 3 In the same equipment and under the same conditions employed in Example 1, samples of methyl chloroform were tested employing vicinal monoepoxides in combination With various stabilizers as shown in the following table:
- composition of matter comprising methyl chloroform containing a minor amount of 1,4-dioxane and having dissolved therein a stabilizing amount of a vicinal monoepoxide having from 4 to 6 carbon atoms.
- a composition of matter comprising methyl chloroform containing a minor amount of 1,4-dioxane and a minor amount of a compound selected from the group consisting of nitromethane, secondary butyl alcohol and a lower monohydric acetylenic alcohol and having dissolved therein a stabilizing amount of a vicinal aliphatic monoepoxide having from 4 to 6 carbon atoms.
- composition of matter comprising methyl chloroform containing a minor amount of nitromethane and dissolved therein a stabilizing amount of a vicinal monoepoxide having from 4 to 6 carbon atoms.
- composition of matter comprising methyl chloroform containing a minor amount of secondary butyl alcohol and having dissolved therein a stabilizing amount of a vicinal monoepoxide having from 4 to 6 carbon atoms.
- a vapor degreasing solvent composition comprising methyl chloroform containing a small stabilizing amount of 1,4-dioxane and having dissolved therein from 0.05 to 5 percent by Weight of a vicinal monoepoxide having from 4 to 6 carbon atoms.
- a vapor degreasing solvent composition comprising methyl chloroform containing stabilizing amounts of 1,4- dioxane and nitromethane and having dissolved therein from 0.05 to 5 percent by weight of a vicinal monoepoxide having from 4 to 6 carbon atoms.
- a vapor degreasing solvent composition comprising methyl chloroform containing stabilizing amounts of 1,4- dioxane and secondary butyl alcohol having dissolved therein from 0.05 to 5 percent by weight of a vicinal monoepoxide having from 4 to 6 carbon atoms.
- a vapor degreasing solvent composition comprising methyl chloroform containing stabilizing amounts of 1,4- dioxane and a monohydric acetylene alcohol having dissolved therein from 0.05 to 5 percent by weight of a vicinal monoepoxide having from 4 to 6 carbon atoms.
- composition of matter comprising methyl chloroform containing a stabilizing amount of 1,4-dioxane and from 0.10 to 1.5 percent by weight butylene oxide.
- composition of matter comprising methyl chlorofor-m containing a stabilizing amount of 1,4-dioxane and from 0.10 to 1.5 weight percent of amylene oxide.
- composition of matter comprising methyl chloroform containing a stabilizing amount of 1,4-dioxane and from 0.10 to 1.5 weight percent of hexylene oxide.
- composition of matter comprising methyl chloroform containing a stabilizing amount of nitrornethane and from 0.10 to 1.5 weight percent of butylene oxide.
- a composition of matter comprising methyl chloroform containing a stabilizing amount of nitromethane and from 0.10 to 1.5 weight percent of amylene oxide.
- composition of matter comprising methyl chloroform containing a stabilizing amount of secondary butyl alcohol and from 0.10 to 1.5 weight percent of butylene oxide.
- a composition of matter comprising methyl chloroform containing a stabilizing amount of a secondary butyl alcohol and from 0.10 to 1.5 weight percent of amylene oxide.
- composition of matter comprising methyl chloroform containing a stabilizing amount of secondary butyl alcohol and from 0.10 to 1.5 weight percent of hexylene oxide.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Mechanical Engineering (AREA)
- Metallurgy (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preventing Corrosion Or Incrustation Of Metals (AREA)
- Epoxy Compounds (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL113941D NL113941C (en(2012)) | 1960-03-18 | ||
| NL261754D NL261754A (en(2012)) | 1960-03-18 | ||
| US15821A US3049571A (en) | 1960-03-18 | 1960-03-18 | Stabilized degreasing solvent |
| DED35049A DE1173306B (de) | 1960-03-18 | 1960-12-27 | Gegen Zersetzung bei Beruehrung mit Metallen stabilisiertes 1, 1, 1-Trichloraethan |
| GB868/61A GB916129A (en) | 1960-03-18 | 1961-01-09 | Stabilized methyl chloroform |
| FR855774A FR1284254A (fr) | 1960-03-18 | 1961-03-16 | Solvant dégraissant stabilisé |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US15821A US3049571A (en) | 1960-03-18 | 1960-03-18 | Stabilized degreasing solvent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3049571A true US3049571A (en) | 1962-08-14 |
Family
ID=21773819
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US15821A Expired - Lifetime US3049571A (en) | 1960-03-18 | 1960-03-18 | Stabilized degreasing solvent |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3049571A (en(2012)) |
| DE (1) | DE1173306B (en(2012)) |
| FR (1) | FR1284254A (en(2012)) |
| GB (1) | GB916129A (en(2012)) |
| NL (2) | NL261754A (en(2012)) |
Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3281480A (en) * | 1961-08-09 | 1966-10-25 | Pittsburgh Plate Glass Co | Stabilization of methyl chloroform |
| DE1246702B (de) * | 1962-10-18 | 1967-08-10 | Dynamit Nobel Ag | Stabilisierung von 1, 1, 1-Trichloraethan |
| US3536766A (en) * | 1968-12-26 | 1970-10-27 | Dow Chemical Co | Stabilized methyl chloroform composition |
| US3681469A (en) * | 1970-09-21 | 1972-08-01 | Dow Chemical Co | Stabilization of 1,1,1-trichloroethane |
| US3878256A (en) * | 1962-10-18 | 1975-04-15 | Dynamit Nobel Ag | Stabilization of 1,1,1-trichloroethane with a four component system |
| US3959397A (en) * | 1962-10-18 | 1976-05-25 | Dynamit Nobel Aktiengesellschaft | Stabilization of 1,1,1-trichloroethane with a three component system |
| US4069265A (en) * | 1962-10-18 | 1978-01-17 | Dynamit Nobel Aktiengesellschaft | Stabilization of 1,1,1-trichloroethane with a four component system |
| EP0044111A1 (fr) * | 1980-07-15 | 1982-01-20 | SOLVAY & Cie (Société Anonyme) | Compositions stabilisées de 1,1,1-trichloroéthane |
| US4327232A (en) * | 1981-02-19 | 1982-04-27 | The Dow Chemical Company | Cyclopropane ring-containing compounds as inhibitor components in methylchloroform |
| US4351973A (en) * | 1980-10-06 | 1982-09-28 | The Dow Chemical Company | Stabilized methylchloroform |
| FR2503697A1 (fr) * | 1981-04-13 | 1982-10-15 | Solvay | Compositions stabilisees de 1,1,1-trichloroethane |
| US4356038A (en) * | 1979-07-25 | 1982-10-26 | Imperial Chemical Industries Limited | Stabilization of chlorinated aliphatic hydrocarbons and use of stabilized composition in cleaning articles |
| US4394284A (en) * | 1981-02-03 | 1983-07-19 | The Dow Chemical Company | Stabilized methylchloroform composition |
| US4597890A (en) * | 1985-02-15 | 1986-07-01 | The Dow Chemical Company | Solvent blend for removing flux residues |
| US5759985A (en) * | 1995-07-21 | 1998-06-02 | Advanced Chemical Design, Inc. | Compositions for the stabilization of bromochloromethane |
| US5801136A (en) * | 1994-08-19 | 1998-09-01 | Advanced Chemical Design, Inc. | Stabilized solvents and method for cleaning metallic, electrical and plastic substrates utilizing environmentally safe solvent materials |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA737892A (en) * | 1963-12-12 | 1966-07-05 | W. Bauer Albert | Cleaning composition |
| CA1008087A (en) * | 1972-08-16 | 1977-04-05 | Wesley L. Archer | Stabilized methylchloroform |
| DE2717322A1 (de) * | 1977-04-19 | 1978-10-26 | Wacker Chemie Gmbh | Stabilisiertes von 1,1,1-trichloraethan |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2371645A (en) * | 1943-09-16 | 1945-03-20 | Westvaco Chlorine Products Cor | Degreasing process |
| GB773187A (en) * | 1955-12-08 | 1957-04-24 | Hoechst Ag | Method of stabilizing halogenated methanes |
| US2811252A (en) * | 1954-03-30 | 1957-10-29 | Dow Chemical Co | Methyl chloroform inhibited with dioxane |
| US2838458A (en) * | 1955-09-30 | 1958-06-10 | Dow Chemical Co | Inhibited methyl chloroform |
| US2923747A (en) * | 1958-04-07 | 1960-02-02 | Dow Chemical Co | Prevention of corrosion |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2364588A (en) * | 1943-04-19 | 1944-12-05 | Shell Dev | Stabilization of halobutenes |
-
0
- NL NL113941D patent/NL113941C/xx active
- NL NL261754D patent/NL261754A/xx unknown
-
1960
- 1960-03-18 US US15821A patent/US3049571A/en not_active Expired - Lifetime
- 1960-12-27 DE DED35049A patent/DE1173306B/de active Pending
-
1961
- 1961-01-09 GB GB868/61A patent/GB916129A/en not_active Expired
- 1961-03-16 FR FR855774A patent/FR1284254A/fr not_active Expired
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2371645A (en) * | 1943-09-16 | 1945-03-20 | Westvaco Chlorine Products Cor | Degreasing process |
| US2811252A (en) * | 1954-03-30 | 1957-10-29 | Dow Chemical Co | Methyl chloroform inhibited with dioxane |
| US2838458A (en) * | 1955-09-30 | 1958-06-10 | Dow Chemical Co | Inhibited methyl chloroform |
| GB773187A (en) * | 1955-12-08 | 1957-04-24 | Hoechst Ag | Method of stabilizing halogenated methanes |
| US2923747A (en) * | 1958-04-07 | 1960-02-02 | Dow Chemical Co | Prevention of corrosion |
Cited By (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3281480A (en) * | 1961-08-09 | 1966-10-25 | Pittsburgh Plate Glass Co | Stabilization of methyl chloroform |
| DE1246702B (de) * | 1962-10-18 | 1967-08-10 | Dynamit Nobel Ag | Stabilisierung von 1, 1, 1-Trichloraethan |
| US3878256A (en) * | 1962-10-18 | 1975-04-15 | Dynamit Nobel Ag | Stabilization of 1,1,1-trichloroethane with a four component system |
| US3959397A (en) * | 1962-10-18 | 1976-05-25 | Dynamit Nobel Aktiengesellschaft | Stabilization of 1,1,1-trichloroethane with a three component system |
| US4069265A (en) * | 1962-10-18 | 1978-01-17 | Dynamit Nobel Aktiengesellschaft | Stabilization of 1,1,1-trichloroethane with a four component system |
| US3536766A (en) * | 1968-12-26 | 1970-10-27 | Dow Chemical Co | Stabilized methyl chloroform composition |
| US3681469A (en) * | 1970-09-21 | 1972-08-01 | Dow Chemical Co | Stabilization of 1,1,1-trichloroethane |
| US4356038A (en) * | 1979-07-25 | 1982-10-26 | Imperial Chemical Industries Limited | Stabilization of chlorinated aliphatic hydrocarbons and use of stabilized composition in cleaning articles |
| FR2486967A1 (fr) * | 1980-07-15 | 1982-01-22 | Solvay | Compositions stabilisees de 1,1,1-trichloroethane |
| EP0044111A1 (fr) * | 1980-07-15 | 1982-01-20 | SOLVAY & Cie (Société Anonyme) | Compositions stabilisées de 1,1,1-trichloroéthane |
| US4351973A (en) * | 1980-10-06 | 1982-09-28 | The Dow Chemical Company | Stabilized methylchloroform |
| US4394284A (en) * | 1981-02-03 | 1983-07-19 | The Dow Chemical Company | Stabilized methylchloroform composition |
| US4327232A (en) * | 1981-02-19 | 1982-04-27 | The Dow Chemical Company | Cyclopropane ring-containing compounds as inhibitor components in methylchloroform |
| FR2503697A1 (fr) * | 1981-04-13 | 1982-10-15 | Solvay | Compositions stabilisees de 1,1,1-trichloroethane |
| US4795837A (en) * | 1981-04-13 | 1989-01-03 | Solvay & Cie (Societe Anonyme) | Stabilized compositions of 1,1,1-trichloroethane |
| US4597890A (en) * | 1985-02-15 | 1986-07-01 | The Dow Chemical Company | Solvent blend for removing flux residues |
| US5801136A (en) * | 1994-08-19 | 1998-09-01 | Advanced Chemical Design, Inc. | Stabilized solvents and method for cleaning metallic, electrical and plastic substrates utilizing environmentally safe solvent materials |
| US5759985A (en) * | 1995-07-21 | 1998-06-02 | Advanced Chemical Design, Inc. | Compositions for the stabilization of bromochloromethane |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1284254A (fr) | 1962-02-09 |
| DE1173306B (de) | 1964-07-02 |
| NL113941C (en(2012)) | |
| GB916129A (en) | 1963-01-23 |
| NL261754A (en(2012)) |
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