NO812415L - STABILIZED 1,1,1-TRICHLORETHAN MIXTURES. - Google Patents
STABILIZED 1,1,1-TRICHLORETHAN MIXTURES.Info
- Publication number
- NO812415L NO812415L NO812415A NO812415A NO812415L NO 812415 L NO812415 L NO 812415L NO 812415 A NO812415 A NO 812415A NO 812415 A NO812415 A NO 812415A NO 812415 L NO812415 L NO 812415L
- Authority
- NO
- Norway
- Prior art keywords
- methyl
- trichloroethane
- epoxybutane
- mixture according
- alcohols
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims description 27
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 title claims description 23
- -1 epoxide compound Chemical class 0.000 claims description 22
- CEBKHWWANWSNTI-UHFFFAOYSA-N 2-methylbut-3-yn-2-ol Chemical compound CC(C)(O)C#C CEBKHWWANWSNTI-UHFFFAOYSA-N 0.000 claims description 13
- 150000001298 alcohols Chemical class 0.000 claims description 13
- QPBYBLZYMNWGMO-UHFFFAOYSA-N 2,2,3-trimethyloxirane Chemical compound CC1OC1(C)C QPBYBLZYMNWGMO-UHFFFAOYSA-N 0.000 claims description 9
- 125000004971 nitroalkyl group Chemical group 0.000 claims description 8
- 239000003381 stabilizer Substances 0.000 claims description 7
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- 150000002576 ketones Chemical class 0.000 claims description 4
- MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 3
- 150000002170 ethers Chemical class 0.000 claims description 3
- 150000002825 nitriles Chemical class 0.000 claims description 3
- 239000004593 Epoxy Substances 0.000 claims description 2
- LYGJENNIWJXYER-BJUDXGSMSA-N nitromethane Chemical group [11CH3][N+]([O-])=O LYGJENNIWJXYER-BJUDXGSMSA-N 0.000 claims description 2
- 239000003921 oil Substances 0.000 description 11
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
- 229910052751 metal Inorganic materials 0.000 description 9
- 239000002184 metal Substances 0.000 description 9
- 238000005238 degreasing Methods 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 238000005520 cutting process Methods 0.000 description 6
- 150000002739 metals Chemical class 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- YKYONYBAUNKHLG-UHFFFAOYSA-N propyl acetate Chemical compound CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical class CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 230000006641 stabilisation Effects 0.000 description 3
- 238000011105 stabilization Methods 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 2
- HNVRRHSXBLFLIG-UHFFFAOYSA-N 3-hydroxy-3-methylbut-1-ene Chemical compound CC(C)(O)C=C HNVRRHSXBLFLIG-UHFFFAOYSA-N 0.000 description 2
- MXGSILCFPNVDMX-UHFFFAOYSA-N 3-hydroxyhexane-2,5-dione Chemical compound CC(=O)CC(O)C(C)=O MXGSILCFPNVDMX-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- ACIAHEMYLLBZOI-ZZXKWVIFSA-N Unsaturated alcohol Chemical compound CC\C(CO)=C/C ACIAHEMYLLBZOI-ZZXKWVIFSA-N 0.000 description 2
- 150000007824 aliphatic compounds Chemical class 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 1
- VDFVNEFVBPFDSB-UHFFFAOYSA-N 1,3-dioxane Chemical compound C1COCOC1 VDFVNEFVBPFDSB-UHFFFAOYSA-N 0.000 description 1
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
- IQOJTGSBENZIOL-UHFFFAOYSA-N 1-(2-Furanyl)-2-propanone Chemical compound CC(=O)CC1=CC=CO1 IQOJTGSBENZIOL-UHFFFAOYSA-N 0.000 description 1
- OXHNLMTVIGZXSG-UHFFFAOYSA-N 1-Methylpyrrole Chemical compound CN1C=CC=C1 OXHNLMTVIGZXSG-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- JSZOAYXJRCEYSX-UHFFFAOYSA-N 1-nitropropane Chemical compound CCC[N+]([O-])=O JSZOAYXJRCEYSX-UHFFFAOYSA-N 0.000 description 1
- GELKGHVAFRCJNA-UHFFFAOYSA-N 2,2-Dimethyloxirane Chemical compound CC1(C)CO1 GELKGHVAFRCJNA-UHFFFAOYSA-N 0.000 description 1
- UDDGYNNPOKTCHY-UHFFFAOYSA-N 2,3-bis(trifluoromethyl)but-2-enedinitrile Chemical group FC(F)(F)C(C#N)=C(C#N)C(F)(F)F UDDGYNNPOKTCHY-UHFFFAOYSA-N 0.000 description 1
- QVTPWONEVZJCCS-UHFFFAOYSA-N 2-formylbenzonitrile Chemical compound O=CC1=CC=CC=C1C#N QVTPWONEVZJCCS-UHFFFAOYSA-N 0.000 description 1
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical group CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 1
- SWBDKCMOLSUXRH-UHFFFAOYSA-N 2-nitrobenzonitrile Chemical compound [O-][N+](=O)C1=CC=CC=C1C#N SWBDKCMOLSUXRH-UHFFFAOYSA-N 0.000 description 1
- FGLBSLMDCBOPQK-UHFFFAOYSA-N 2-nitropropane Chemical compound CC(C)[N+]([O-])=O FGLBSLMDCBOPQK-UHFFFAOYSA-N 0.000 description 1
- NDVLTZFQVDXFAN-UHFFFAOYSA-N 3-(2-cyanoethylsulfanyl)propanenitrile Chemical compound N#CCCSCCC#N NDVLTZFQVDXFAN-UHFFFAOYSA-N 0.000 description 1
- BNDRWEVUODOUDW-UHFFFAOYSA-N 3-Hydroxy-3-methylbutan-2-one Chemical compound CC(=O)C(C)(C)O BNDRWEVUODOUDW-UHFFFAOYSA-N 0.000 description 1
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 1
- OVKDLPZRDQTOJW-UHFFFAOYSA-N 3-amino-2-methylbutan-2-ol Chemical compound CC(N)C(C)(C)O OVKDLPZRDQTOJW-UHFFFAOYSA-N 0.000 description 1
- VUXKVKAHWOVIDN-UHFFFAOYSA-N Cyclohexyl formate Chemical class O=COC1CCCCC1 VUXKVKAHWOVIDN-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- DNVWJWSHVBHFKS-UHFFFAOYSA-N acetonitrile N-methylmethanamine Chemical compound C(C)#N.CNC DNVWJWSHVBHFKS-UHFFFAOYSA-N 0.000 description 1
- IDVJXKFJHUNVNB-UHFFFAOYSA-N acetonitrile;n-ethylethanamine Chemical compound CC#N.CCNCC IDVJXKFJHUNVNB-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 1
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 239000003990 capacitor Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 1
- 150000001983 dialkylethers Chemical class 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000005108 dry cleaning Methods 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- MPXPIDURTPPYSY-UHFFFAOYSA-N ethynyl propanoate Chemical class CCC(=O)OC#C MPXPIDURTPPYSY-UHFFFAOYSA-N 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 1
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 1
- LDHQCZJRKDOVOX-IHWYPQMZSA-N isocrotonic acid Chemical class C\C=C/C(O)=O LDHQCZJRKDOVOX-IHWYPQMZSA-N 0.000 description 1
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 description 1
- 238000003754 machining Methods 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- PZPMLEMQMIYNIU-UHFFFAOYSA-N methanamine propanenitrile Chemical compound C(CC)#N.CN PZPMLEMQMIYNIU-UHFFFAOYSA-N 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- DGJFLIRBDQYRGG-UHFFFAOYSA-N n-methylmethanamine;propanenitrile Chemical compound CNC.CCC#N DGJFLIRBDQYRGG-UHFFFAOYSA-N 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- BYYYEOMMIGRDST-UHFFFAOYSA-N prop-1-ynyl acetate Chemical class CC#COC(C)=O BYYYEOMMIGRDST-UHFFFAOYSA-N 0.000 description 1
- JADOFECNZGDUSZ-UHFFFAOYSA-N prop-2-ynyl butanoate Chemical class CCCC(=O)OCC#C JADOFECNZGDUSZ-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical class CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- PCCVSPMFGIFTHU-UHFFFAOYSA-N tetracyanoquinodimethane Chemical compound N#CC(C#N)=C1C=CC(=C(C#N)C#N)C=C1 PCCVSPMFGIFTHU-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 238000005491 wire drawing Methods 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
- C23G5/02883—Nitrogen-containing compounds
- C23G5/02887—Nitro-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
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)
- Lubricants (AREA)
- Fats And Perfumes (AREA)
- Detergent Compositions (AREA)
Description
Den foreliggende oppfinnelse angår stabiliserte 1,1,1-trikloretan-holdige blandinger som kan anvendes for avfetting av metaller, idet en konstant pH bibeholdes. The present invention relates to stabilized 1,1,1-trichloroethane-containing mixtures which can be used for degreasing metals, while maintaining a constant pH.
Det er kjent at 1,1,1-trikloretan, som spesielt anvendes for avfetting av metaller og tørr-rensing av tekstiler, og i aerosoler, medfører et meget spesielt stabilitets- og korro-sjonsproblem. Anvendelse av de stabiliseringsmidler som nor-malt brukes for andre klorerte hydrokarboner for stabilisering v av 1,1,1-trikloretan, gir i alminnelighet ikke tilfredsstillende resultater. Dette fenomen er blitt tilskrevet det faktum at det er en høy reaktivitet. mellom metaller og 1,1,1-trikloretan, hvilken reaktivitet i løpet av meget kort tid gir opphav til spaltning av 1,1,1-trikloretanet og angrep på metallet. It is known that 1,1,1-trichloroethane, which is particularly used for degreasing metals and dry-cleaning textiles, and in aerosols, causes a very special stability and corrosion problem. Application of the stabilizers which are normally used for other chlorinated hydrocarbons for the stabilization of 1,1,1-trichloroethane generally does not give satisfactory results. This phenomenon has been attributed to the fact that there is a high reactivity. between metals and 1,1,1-trichloroethane, which reactivity within a very short time gives rise to decomposition of the 1,1,1-trichloroethane and attack on the metal.
For stabilisering av 1,1,1-trikloretan er det allerede blitt foreslått å anvende epoksyd-forbindelser sammen med nitro-alkaner (U.S. patent nr. 3 049 571,.nr. 3 532 761, nr. For stabilization of 1,1,1-trichloroethane, it has already been proposed to use epoxide compounds together with nitroalkanes (U.S. Patent No. 3,049,571, No. 3,532,761, No.
4 026 956 og belgisk patent nr. 763.703. Ifølge disse patenter 4,026,956 and Belgian Patent No. 763,703. According to these patents
kan forskjellige epoksyd-forbindelser anvendes for dette -formål. Da imidlertid epoksybutan er det eneste som er tilgjenge-lig under kommersielt fordelaktige betingelser, er denne forbindelse fremdeles den som anvendes i praksis. different epoxy compounds can be used for this purpose. However, since epoxybutane is the only one available under commercially advantageous conditions, this compound is still the one used in practice.
Skjønt pH-stabiliteten av 1,1,1-trikloretan-holdige blandinger stabilisert ved hjelp av epoksybutan kan anses som tilfredsstillende i de fleste tilfeller, gjenstår likevel stabili-tetsproblemer når disse blandinger anvendes for avfetting av metall-deler som er fuktet med oljer for skjærende verktøy. I dette tilfelle observeres, avhengig av den anvendte oljens art, at den 1,1,1-trikloretan-holdige blanding blir sur eller basisk, og dette gjør det nødvendig å tilpasse stabiliserings-midlets sammensetning i hvert enkelt tilfelle. Although the pH stability of 1,1,1-trichloroethane-containing mixtures stabilized with epoxybutane can be considered satisfactory in most cases, stability problems still remain when these mixtures are used for degreasing metal parts that are wetted with oils for cutting tools. In this case, it is observed, depending on the nature of the oil used, that the 1,1,1-trichloroethane-containing mixture becomes acidic or basic, and this makes it necessary to adapt the composition of the stabilizer in each individual case.
Formålet med den foreliggende oppfinnelse er å tilveie-bringe 1,1,1-trikloretan-holdige blandinger hvis pH ikke varierer, selv når de anvendes, for avfetting av metall-deler som er fuktet med forskjellige typer av oljer for skjærende verktøy. The purpose of the present invention is to provide 1,1,1-trichloroethane-containing mixtures whose pH does not vary, even when used, for degreasing metal parts that are moistened with different types of oils for cutting tools.
Oppfinnelsen angår således 1,1,1-trikloretan-holdige blan-.dinger inneholdende minst ett nitroalkan og minst en epoksyd-forbindelse, nemlig 2-metyl-2,3-epoksybutan. The invention thus relates to 1,1,1-trichloroethane-containing mixtures containing at least one nitroalkane and at least one epoxide compound, namely 2-methyl-2,3-epoxybutane.
Nitroalkanet i blandingene ifølge oppfinnelsen inneholder . vanligvis 1-4 karbonatomer. Det er fortrinnsvis nitrometan, The nitroalkane in the mixtures according to the invention contains . usually 1-4 carbon atoms. It is preferably nitromethane,
nitroetan, 1-nitropropan eller 2-nitropropan eller en blanding av disse forbindelser. Nitrometan og nitroetan er meget spesielt foretrukket. nitroethane, 1-nitropropane or 2-nitropropane or a mixture of these compounds. Nitromethane and nitroethane are very particularly preferred.
Mengden nitroalkan varierer vanligvis mellom 0,001 mol ogThe amount of nitroalkane usually varies between 0.001 mol and
1 mol pr. liter 1,1,1-trikloretan. Fortrinnsvis er denne mengde mellom 0,01 og 0,5 mol pr. liter. Mengder mellom 0,05 og 0,3 mol pr. liter 1,1,1-trikloretan er meget spesielt foretrukket. 1 mole per liter of 1,1,1-trichloroethane. Preferably, this amount is between 0.01 and 0.5 mol per litres. Amounts between 0.05 and 0.3 mol per liters of 1,1,1-trichloroethane is very particularly preferred.
Mengdene av 2-mety1-2,3-epoksybutan, som også er referert' til som isoamylenoksyd, er de samme som.de som er beskrevet ovenfor for nitroalkanene. The amounts of 2-methyl-2,3-epoxybutane, also referred to as isoamylene oxide, are the same as those described above for the nitroalkanes.
Foruten de ovenfor nevnte forbindelser kan blandingene inneholde en eller flere andre stabilisatorer som er vanlig for. 1,1,1-trikloretan, såsom alkoholer, estere, nitriler, indre etere og ketoner, og dessuten epoksydforbindelser som isobuten-oksyd. Blandingene som inneholder 2-metyl-2,3-epoxybutan som den eneste epoksyd-forbindelse foretrekkes imidlertid. In addition to the above-mentioned compounds, the mixtures may contain one or more other stabilizers which are common for. 1,1,1-trichloroethane, such as alcohols, esters, nitriles, internal ethers and ketones, and also epoxide compounds such as isobutene oxide. However, the mixtures containing 2-methyl-2,3-epoxybutane as the sole epoxide compound are preferred.
Alkoholene kan være mettet eller umettet. De foretrukne alkoholer inneholder 1-7 karbonatomer og kan være substituerte eller usubstituerte. Vanligvis er de usubstituerte alkoholer. The alcohols can be saturated or unsaturated. The preferred alcohols contain 1-7 carbon atoms and may be substituted or unsubstituted. Usually they are unsubstituted alcohols.
Eksempler på mettede alkoholer er metanol, etanol, propa-nol, isopropanol, butan-l-ol, butan-2-ol, tertiær butylalkohol, pentanoler såsom tertiær amylalkohol, etylenglykol-monomety1-, monoetyt, monopropy 1-eller monobuty leter, glyserol, etylengly-^kol, propylenglykol, 2-hydroksy-2-metylbutan-3-on, 3,3-dimetoksy-2 - metylbutan-2-dl og 3-amino-2-metylbutan-2-ol. Meget gode resultater er oppnådd med propanoler, tertiære og sekundære butanoler og tertiær pentanol. Den foretrukne mettede alkohol er tertiær butanol. Examples of saturated alcohols are methanol, ethanol, propanol, isopropanol, butan-1-ol, butan-2-ol, tertiary butyl alcohol, pentanols such as tertiary amyl alcohol, ethylene glycol monomethyl-, monoethyl, monopropyl or monobutyl ether, glycerol , ethylene glycol, propylene glycol, 2-hydroxy-2-methylbutan-3-one, 3,3-dimethoxy-2 - methylbutan-2-dl and 3-amino-2-methylbutan-2-ol. Very good results have been achieved with propanols, tertiary and secondary butanols and tertiary pentanol. The preferred saturated alcohol is tertiary butanol.
De umettede alkoholer som vanligvis brukes er usubstituerte alkoholer inneholdende 3-6 karbonatomer. Blant disse foretrekkes ally1-alkohol, 2-metylbut-3-en-2-ol og 2-metylbut-3-yn-2-ol. Den foretrukne umettede alkohol er 2-metylbut-3-yn-2-ol. The unsaturated alcohols that are usually used are unsubstituted alcohols containing 3-6 carbon atoms. Among these, allyl alcohol, 2-methylbut-3-en-2-ol and 2-methylbut-3-yn-2-ol are preferred. The preferred unsaturated alcohol is 2-methylbut-3-yn-2-ol.
De vanligst brukte estere er monoestere og diestere som inneholder 2-8 karbonatomer, som er mettet eller umettet og som kan være substituert med halogener eller hydroksylgrupper, såsom etyl-, propyl-, isopropyl-, butyl-, sek.-butyl-, tert.-butyl-, amyl-, heksy 1- og . cykloheksyl-f ormiater , metyl-, etyl-,• propyl- , isopropyl-, butyl-, amyl-, etynyl- og propynyl-acetater, metyl-, etyl-, propyl-, isopropyl-, butyl-, amyl- og etynyl-propionater,. metyl-, etyl-, propyl-, isopropyl- og prop-2-ynyl-butyrater, metyl-, etyl-, propyl-, isopropyl-, butyl-, sek.-butyl- og tert.-butyl-akrylater og metakrylater, metyl- og etyl-krotona-ter og isokrotonater,. etyl- og metyl-sorbinater, etyl-diformiat og etyl-diacetat. Usubstituerte mon-estere som inneholder 4-6 karbonatomer er egnet. Meget gode resultater er oppnådd med etylacetat, isobutylacetat, n-propylacetat, metyl-metakrylat og n-butylacetat. Metyl-metakrylat, etylacetat og n-propylacetat har vist seg å være særlig egnet. The most commonly used esters are monoesters and diesters containing 2-8 carbon atoms, which are saturated or unsaturated and which may be substituted with halogens or hydroxyl groups, such as ethyl-, propyl-, isopropyl-, butyl-, sec-butyl-, tert .-butyl-, amyl-, hexy 1- and . cyclohexyl formates, methyl, ethyl,• propyl, isopropyl, butyl, amyl, ethynyl and propynyl acetates, methyl, ethyl, propyl, isopropyl, butyl, amyl and ethynyl -propionates,. methyl, ethyl, propyl, isopropyl and prop-2-ynyl butyrates, methyl, ethyl, propyl, isopropyl, butyl, sec-butyl and tert-butyl acrylates and methacrylates, methyl and ethyl crotonates and isocrotonates. ethyl and methyl sorbinates, ethyl diformate and ethyl diacetate. Unsubstituted monoesters containing 4-6 carbon atoms are suitable. Very good results have been obtained with ethyl acetate, isobutyl acetate, n-propyl acetate, methyl methacrylate and n-butyl acetate. Methyl methacrylate, ethyl acetate and n-propyl acetate have been found to be particularly suitable.
De mest brukte nitriler er eventuelt substituerte,The most commonly used nitriles are optionally substituted,
mettede eller umettede, alifatiske eller aromatiske forbindelser inneholdende 2-7 karbonatomer, såsom acetonitril, propionitril, acrylnitril, butyr-nitril, metakry1-nitril, malon-nitril, benznitril, dimetylamin-acetonitril, metylamin-propionitril, dimetylamin-propionitril, dietylamin -acetonitril, metyletyl-amin-acetonitril, tiodipropio-nitril, tetracyan - etylen, tetra-cyankvinodimetan, tetracyanditiin, 1,2-dicyan-l,2-bis-(tri-fluormetyl)-etylen, cyan-benzaldehyd, nitro-benznitril og cyan-pyridin. Blant disse er acetonitril, propionitril og acrylnitril de mest egnede. saturated or unsaturated, aliphatic or aromatic compounds containing 2-7 carbon atoms, such as acetonitrile, propionitrile, acrylonitrile, butyr-nitrile, methacrylonitrile, malon-nitrile, benznitrile, dimethylamine-acetonitrile, methylamine-propionitrile, dimethylamine-propionitrile, diethylamine-acetonitrile , methylethylamine-acetonitrile, thiodipropionitrile, tetracyan - ethylene, tetra-cyanoquinodimethane, tetracyandithiin, 1,2-dicyan-1,2-bis-(tri-fluoromethyl)-ethylene, cyano-benzaldehyde, nitro-benznitrile and cyan -pyridine. Among these, acetonitrile, propionitrile and acrylonitrile are the most suitable.
De særlig egnete interne etere er monosykliske eller polysykliske etere som vekselvis kan inneholde andre hetero-atomer og som inneholder en eller flere substituerte eller usubstituerte, mettede eller umettede ringer med 5 eller 6 karbonatomer, såsom 1,3 dioksan, 1,4-dioksan, 1,3,5-trioksan, 1,3-dioksolan, dioksen, dioksadien, tioksan, oksazol, tetrahydro-furan, difeny1-eter.og lignende. The particularly suitable internal ethers are monocyclic or polycyclic ethers which can alternately contain other heteroatoms and which contain one or more substituted or unsubstituted, saturated or unsaturated rings with 5 or 6 carbon atoms, such as 1,3-dioxane, 1,4-dioxane, 1,3,5-trioxane, 1,3-dioxolane, dioxane, dioxadiene, thioxane, oxazole, tetrahydrofuran, diphenyl ether and the like.
Ketoner som kan benyttes er substituerte eller.usubstituerte ketoner inneholdende 3-7 karbonatomer, såsom for eksempel aceton,, mety 1-ety 1-keton , dietyl-keton, mety 1-propy 1-keton, mety1-isopropyl-keton, 1-(furan-2-y1)-propanon, 3-hydroksy-heksan-2,5-dion, 2-metyl-2-hydroksypentan-4-on og lignende. Ketones that can be used are substituted or unsubstituted ketones containing 3-7 carbon atoms, such as, for example, acetone, methyl 1-ethyl 1-ketone, diethyl ketone, methyl 1-propyl 1-ketone, methyl 1-isopropyl ketone, 1- (furan-2-yl)-propanone, 3-hydroxy-hexane-2,5-dione, 2-methyl-2-hydroxypentan-4-one and the like.
Andre forbindelser, og særlig alkoksyalkaner såsom alkoksy-etaner, nitrater som alky1-nitrater inneholdende 1-5 karbonatomer, aminer som alifatiske aminer inneholdende 2-6 karbonatomer, pyrroler'såsom n-metyl-pyrrol, og andre aromatiske forbindelser såsom toluen, eller alifatiske forbindelser såsom di-isobutylen, Other compounds, and in particular alkoxyalkanes such as alkoxyethanes, nitrates such as alkyl nitrates containing 1-5 carbon atoms, amines such as aliphatic amines containing 2-6 carbon atoms, pyrroles such as n-methyl-pyrrole, and other aromatic compounds such as toluene, or aliphatic compounds such as di-isobutylene,
kan også inkorporeres i stabiliseringsmidlet som til slutt brukes for 1,1,1-trikloretan. can also be incorporated into the stabilizer ultimately used for 1,1,1-trichloroethane.
De forskjellige andre stabilisatorer som anvendes er. vanligvis tilstede i mengder mellom 0,01 og 2 mol pr..liter 1,1,1-trikloretan og fortrinnsvis i mengder mellom 0,1 og 0,8 mol pr. liter. The various other stabilizers used are. usually present in amounts between 0.01 and 2 moles per liter of 1,1,1-trichloroethane and preferably in amounts between 0.1 and 0.8 moles per liter. litres.
Blandinger som er meget effektivt stabilisert ifølge oppfinnelsen inneholder, foruten 2-metyl-2,3-epoksybutan og nitro-metan eller nitro-etan, en mettet alkohol, mer spe-. sielt tertiær butylalkohol, og en umettet alkohol, mer spesielt - 2-metylbut-3-yn-2-ol. Mixtures which are very effectively stabilized according to the invention contain, in addition to 2-methyl-2,3-epoxybutane and nitro-methane or nitro-ethane, a saturated alcohol, more spe-. particularly tertiary butyl alcohol, and an unsaturated alcohol, more particularly - 2-methylbut-3-yn-2-ol.
De ifølge oppfinnelsen stabiliserte 1,1,1-trikloretan-blandinger kan brukes for ethvert formål hvor det kreves god stabilisering av den anvendte 1,1,1-trikloretan. De anvendes fortrinnsvis for å avfette metaller og mer spesielt for avfetting av metaller som er fuktet med oljer for skjærende verktøy. Betegnelsen "oljer for skjærende verktøy" omfatter enhver type olje eller fett anvendt ved operasjoner som maskinbehandling, utboring, polering og trådtrekking av metaller. The 1,1,1-trichloroethane mixtures stabilized according to the invention can be used for any purpose where good stabilization of the 1,1,1-trichloroethane used is required. They are preferably used for degreasing metals and more particularly for degreasing metals that have been moistened with oils for cutting tools. The term "cutting tool oils" includes any type of oil or grease used in operations such as machining, boring, polishing and wire drawing of metals.
Eksemplene som følger indikerer ikke. på noen måte noen begrensning. The examples that follow do not indicate. in any way any limitation.
Eksempel 1Example 1
Dette eksempel er et sammenligningseksempel.This example is a comparison example.
300 cm 3 trikloretan stabilisert med 0,541 mol/l tertiær buty1-alkohol, 0,164 mol/l nitrometan, 0,208 mol/l 2-metylbut-3-yn-2-ol og 0,079 mol/l epoksybutan, og 75 cm 3 olje for skjærende verktøy (henholdsvis kaleol-olje i Eksperiment 1, kalsium-stearat i Eksperiment 2 og polybutylcuprisil i Eksperiment 3) haes i en 500 cm^ rundbunnet kolbe forsynt med et termometer og utstyrt med et SOXI-ILET-type ekstraksjonsapparat med en kapasitet på 100 cm 3, som igjen er tilkoblet en kondensator, og det hele er beskyttet mot lyset. 300 cm 3 trichloroethane stabilized with 0.541 mol/l tertiary buty1-alcohol, 0.164 mol/l nitromethane, 0.208 mol/l 2-methylbut-3-yn-2-ol and 0.079 mol/l epoxybutane, and 75 cm 3 oil for cutting tools (respectively kaleol oil in Experiment 1, calcium stearate in Experiment 2 and polybutylcuprisil in Experiment 3) are placed in a 500 cm^ round-bottomed flask fitted with a thermometer and equipped with a SOXI-ILET type extraction apparatus with a capacity of 100 cm 3, which is again connected to a capacitor, and the whole thing is protected from the light.
Blandingen holdes på kokepunktet . i 72 timer, og oppvarmin-gen justeres slik at ekstraksjonsapparatet fylles og tømmes helt med 30 minutters intervaller. Følgelig varierer konsentra-sjonen av olje for skjærende verktøy i blandingen kontinuerlig mellom 20 og.27,6 volum%, og imiterer således de forhold som ' forekommer i industrimaskiner for avfetting i dampfasen. The mixture is kept at the boiling point. for 72 hours, and the heating is adjusted so that the extraction apparatus is filled and emptied completely at 30-minute intervals. Consequently, the concentration of oil for cutting tools in the mixture varies continuously between 20 and 27.6% by volume, thus imitating the conditions that occur in industrial machines for degreasing in the vapor phase.
Etter kokeperioden på 72 timer tømmes innholdet i eks- tråksjonsapparatet ned i kolben, kondensatoren monteres i skrå stilling og oppløsningsmidlet gjenvinnes ved destillasjon. Degraderingen av dette oppløsningsmidlet bestemmes ved at surheten måles, og resultatene er angitt i Tabell I nedenfor. After the boiling period of 72 hours, the contents of the extraction apparatus are emptied into the flask, the condenser is mounted in an inclined position and the solvent is recovered by distillation. The degradation of this solvent is determined by measuring the acidity, and the results are given in Table I below.
Eksempel 2 Example 2
Arbeidsoperasjonene i Eksempel 1 gjentas, men prosessen blir utført ved bruk av 1,1>1-trikloretan stabilisert med 0,541 mol/l tertiær butylalkohol, 0,164 mol/l nitrometan, 0,208 mol/l 2-metyl-but-3-yn-2-ol og 0,079 mol/1 2-metyl-2,3-epoksybutan. The work operations in Example 1 are repeated, but the process is carried out using 1,1>1-trichloroethane stabilized with 0.541 mol/l tertiary butyl alcohol, 0.164 mol/l nitromethane, 0.208 mol/l 2-methyl-but-3-yn-2 -ol and 0.079 mol/1 2-methyl-2,3-epoxybutane.
Degraderingen av dette oppløsningsmiddel bestemmes ved måling av surheten, og verdiene er angitt i Tabell II nedenfor. The degradation of this solvent is determined by measuring the acidity, and the values are given in Table II below.
En sammenligning av resultatene i Eksempel 1 og 2 viser at en 1,1,1-trikloretan-blanding stabilisert med nitrometan og 1,2-epoksybutan kan angripes ved innvirkning av forskjellige typer oljer og er bare egnet for visse ikke-aggresive oljer, mens blandingen ifølge oppfinnelsen, i hvilken 1,2-epoksybutan er erstattet med en tilsvarende mengde 2-mety1-2,3-epoksybutan, er egnet i alle tilfeller. A comparison of the results in Examples 1 and 2 shows that a 1,1,1-trichloroethane mixture stabilized with nitromethane and 1,2-epoxybutane can be attacked by different types of oils and is only suitable for certain non-aggressive oils, while the mixture according to the invention, in which 1,2-epoxybutane is replaced by a corresponding amount of 2-methyl-2,3-epoxybutane, is suitable in all cases.
Claims (9)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8015767A FR2486967A1 (en) | 1980-07-15 | 1980-07-15 | STABILIZED COMPOSITIONS OF 1,1,1-TRICHLOROETHANE |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO812415L true NO812415L (en) | 1982-01-18 |
Family
ID=9244232
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO812415A NO812415L (en) | 1980-07-15 | 1981-07-14 | STABILIZED 1,1,1-TRICHLORETHAN MIXTURES. |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP0044111A1 (en) |
| DK (1) | DK313881A (en) |
| ES (1) | ES8303546A1 (en) |
| FI (1) | FI812210L (en) |
| FR (1) | FR2486967A1 (en) |
| GR (1) | GR75674B (en) |
| NO (1) | NO812415L (en) |
| PT (1) | PT73339B (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NO834067L (en) * | 1982-11-08 | 1984-05-09 | Dow Chemical Co | SOLVENT MIXTURE TO REMOVE FLUID |
| US4524011A (en) * | 1982-11-08 | 1985-06-18 | The Dow Chemical Company | Flux removal solvent blend |
| US4597890A (en) * | 1985-02-15 | 1986-07-01 | The Dow Chemical Company | Solvent blend for removing flux residues |
| FR2585349B1 (en) * | 1985-07-25 | 1988-03-04 | Solvay | STABILIZED COMPOSITIONS OF 1,1,1-TRICHLORETHANE |
| EP0534829A1 (en) * | 1991-09-27 | 1993-03-31 | Elf Atochem S.A. | Process and additive for stabilising compositions based on halogenated solvents, compositions obtained and their use for degreasing or cleaning metal objects |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL113941C (en) * | 1960-03-18 | |||
| FR1444410A (en) * | 1964-07-20 | 1966-07-01 | Pittsburgh Plate Glass Co | Methyl chloroform compositions |
| NL140224C (en) * | 1969-05-07 | |||
| US3767585A (en) * | 1971-10-12 | 1973-10-23 | Nippon Soda Co | Stable solvent composition |
| US4026956A (en) * | 1972-09-13 | 1977-05-31 | Ppg Industries, Inc. | Storage stabilized methylchloroform formulations |
| FR2429767A1 (en) * | 1978-06-30 | 1980-01-25 | Rhone Poulenc Ind | PROCESS FOR STABILIZING TRICHLORO-1,1,1 ETHANE |
-
1980
- 1980-07-15 FR FR8015767A patent/FR2486967A1/en not_active Withdrawn
-
1981
- 1981-07-01 GR GR65406A patent/GR75674B/el unknown
- 1981-07-06 EP EP81200765A patent/EP0044111A1/en not_active Withdrawn
- 1981-07-09 PT PT73339A patent/PT73339B/en unknown
- 1981-07-14 DK DK313881A patent/DK313881A/en not_active Application Discontinuation
- 1981-07-14 ES ES503943A patent/ES8303546A1/en not_active Expired
- 1981-07-14 FI FI812210A patent/FI812210L/en not_active Application Discontinuation
- 1981-07-14 NO NO812415A patent/NO812415L/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK313881A (en) | 1982-01-16 |
| GR75674B (en) | 1984-08-02 |
| ES503943A0 (en) | 1983-02-01 |
| PT73339A (en) | 1981-08-01 |
| PT73339B (en) | 1982-07-30 |
| ES8303546A1 (en) | 1983-02-01 |
| EP0044111A1 (en) | 1982-01-20 |
| FR2486967A1 (en) | 1982-01-22 |
| FI812210L (en) | 1982-01-16 |
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