DE1902155A1 - Stabilisierende Gemische fuer Chlorfluoralkane sowie ein Verfahren zum Stabilisieren von Chlorfluoralkanen - Google Patents
Stabilisierende Gemische fuer Chlorfluoralkane sowie ein Verfahren zum Stabilisieren von ChlorfluoralkanenInfo
- Publication number
- DE1902155A1 DE1902155A1 DE19691902155 DE1902155A DE1902155A1 DE 1902155 A1 DE1902155 A1 DE 1902155A1 DE 19691902155 DE19691902155 DE 19691902155 DE 1902155 A DE1902155 A DE 1902155A DE 1902155 A1 DE1902155 A1 DE 1902155A1
- Authority
- DE
- Germany
- Prior art keywords
- group
- stabilizing
- oxide
- amounts
- mixtures
- 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.)
- Pending
Links
- 239000000203 mixture Substances 0.000 title claims description 72
- 230000000087 stabilizing effect Effects 0.000 title claims description 23
- 238000000034 method Methods 0.000 title claims description 13
- 239000000126 substance Substances 0.000 claims description 29
- 239000003381 stabilizer Substances 0.000 claims description 19
- -1 alkylene epoxide Chemical class 0.000 claims description 18
- 150000007857 hydrazones Chemical class 0.000 claims description 16
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 claims description 12
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 9
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 claims description 8
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 claims description 8
- 150000003934 aromatic aldehydes Chemical class 0.000 claims description 8
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 230000007062 hydrolysis Effects 0.000 claims description 8
- 238000006460 hydrolysis reaction Methods 0.000 claims description 8
- 125000001931 aliphatic group Chemical group 0.000 claims description 7
- 150000001336 alkenes Chemical class 0.000 claims description 7
- WWUVJRULCWHUSA-UHFFFAOYSA-N 2-methyl-1-pentene Chemical compound CCCC(C)=C WWUVJRULCWHUSA-UHFFFAOYSA-N 0.000 claims description 6
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical group CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 claims description 4
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 4
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 claims description 4
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 claims description 4
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 claims description 4
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 4
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 claims description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 3
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 claims description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 3
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
- 239000005977 Ethylene Substances 0.000 claims 1
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 1
- 229910052742 iron Inorganic materials 0.000 claims 1
- 150000002924 oxiranes Chemical class 0.000 claims 1
- 238000002474 experimental method Methods 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- 238000012360 testing method Methods 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 239000010902 straw Substances 0.000 description 9
- 230000002195 synergetic effect Effects 0.000 description 9
- 150000001298 alcohols Chemical class 0.000 description 8
- 238000000354 decomposition reaction Methods 0.000 description 8
- 239000000443 aerosol Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000003112 inhibitor Substances 0.000 description 6
- 230000007797 corrosion Effects 0.000 description 5
- 238000005260 corrosion Methods 0.000 description 5
- 239000003380 propellant Substances 0.000 description 5
- 230000006641 stabilisation Effects 0.000 description 5
- 238000011105 stabilization Methods 0.000 description 5
- 150000005846 sugar alcohols Polymers 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- XWCDCDSDNJVCLO-UHFFFAOYSA-N Chlorofluoromethane Chemical compound FCCl XWCDCDSDNJVCLO-UHFFFAOYSA-N 0.000 description 4
- 239000004593 Epoxy Substances 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 3
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 3
- 239000006260 foam Substances 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
- 150000003333 secondary alcohols Chemical class 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 229940029284 trichlorofluoromethane Drugs 0.000 description 3
- 239000004604 Blowing Agent Substances 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- 229920005830 Polyurethane Foam Polymers 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- NMDSDEDZLWCSNZ-UHFFFAOYSA-N ethanol;trichloro(fluoro)methane Chemical compound CCO.FC(Cl)(Cl)Cl NMDSDEDZLWCSNZ-UHFFFAOYSA-N 0.000 description 2
- 238000005187 foaming Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000011496 polyurethane foam Substances 0.000 description 2
- 125000000075 primary alcohol group Chemical group 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 1
- FXNDIJDIPNCZQJ-UHFFFAOYSA-N 2,4,4-trimethylpent-1-ene Chemical group CC(=C)CC(C)(C)C FXNDIJDIPNCZQJ-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 102100033213 Teneurin-1 Human genes 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- 230000009172 bursting Effects 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- KYKAJFCTULSVSH-UHFFFAOYSA-N chloro(fluoro)methane Chemical compound F[C]Cl KYKAJFCTULSVSH-UHFFFAOYSA-N 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- WIZOZORCIQKFQD-UHFFFAOYSA-N ethane methane Chemical compound C.C.C.C.C.C.CC WIZOZORCIQKFQD-UHFFFAOYSA-N 0.000 description 1
- RMBYHXZZYKLTJJ-UHFFFAOYSA-N ethanol;methane Chemical compound C.CCO RMBYHXZZYKLTJJ-UHFFFAOYSA-N 0.000 description 1
- OMRRUNXAWXNVFW-UHFFFAOYSA-N fluoridochlorine Chemical compound ClF OMRRUNXAWXNVFW-UHFFFAOYSA-N 0.000 description 1
- XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical compound FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 description 1
- 239000005338 frosted glass Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000008266 hair spray Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000004971 nitroalkyl group Chemical group 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 108010063973 teneurin-1 Proteins 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
Classifications
-
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Detergent Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT1171868 | 1968-01-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1902155A1 true DE1902155A1 (de) | 1969-12-11 |
Family
ID=11137205
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19691902155 Pending DE1902155A1 (de) | 1968-01-18 | 1969-01-17 | Stabilisierende Gemische fuer Chlorfluoralkane sowie ein Verfahren zum Stabilisieren von Chlorfluoralkanen |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3627834A (en, 2012) |
| JP (1) | JPS4937031B1 (en, 2012) |
| BE (1) | BE727043A (en, 2012) |
| BR (1) | BR6905677D0 (en, 2012) |
| DE (1) | DE1902155A1 (en, 2012) |
| ES (1) | ES362637A1 (en, 2012) |
| FR (1) | FR2000367A1 (en, 2012) |
| NL (1) | NL6900516A (en, 2012) |
| SU (1) | SU374809A3 (en, 2012) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2682377A1 (fr) * | 1991-10-11 | 1993-04-16 | Atochem | Stabilisation du 1,1-dichloro-1-fluoroethane. |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4217310A (en) * | 1978-08-18 | 1980-08-12 | Ppg Industries, Inc. | Stabilization of cyclohexene oxide |
| DE4028747A1 (de) * | 1990-09-11 | 1992-03-12 | Hoechst Ag | Stabilisierung von cf(pfeil abwaerts)3(pfeil abwaerts)-chcl(pfeil abwaerts)2(pfeil abwaerts) oder cclf(pfeil abwaerts)2(pfeil abwaerts)-chclf oder deren mischungen gegen die reaktion mit kaeltemaschinenoel |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3043888A (en) * | 1959-02-09 | 1962-07-10 | Pittsburgh Plate Glass Co | Stabilization |
| US3090818A (en) * | 1960-05-11 | 1963-05-21 | Du Pont | Chlorofluoroalkane compositions |
| US3152191A (en) * | 1960-08-08 | 1964-10-06 | Pittsburgh Plate Glass Co | Liquid halogenated hydrocarbon stabilized with a primary alkanol and an alkyl aldehyd hydrazone |
| BE621364A (en, 2012) * | 1961-03-10 | |||
| NL284875A (en, 2012) * | 1961-10-30 | |||
| GB1097387A (en) * | 1965-09-16 | 1968-01-03 | Ici Ltd | Chlorofluoroalkane compositions |
| US3445527A (en) * | 1966-01-21 | 1969-05-20 | Daikin Ind Ltd | Stabilized chlorofluoroalkane composition |
-
1969
- 1969-01-13 NL NL6900516A patent/NL6900516A/xx unknown
- 1969-01-14 US US791145A patent/US3627834A/en not_active Expired - Lifetime
- 1969-01-14 SU SU1297340A patent/SU374809A3/ru active
- 1969-01-16 FR FR6900647A patent/FR2000367A1/fr not_active Withdrawn
- 1969-01-17 DE DE19691902155 patent/DE1902155A1/de active Pending
- 1969-01-17 BR BR205677/69A patent/BR6905677D0/pt unknown
- 1969-01-17 ES ES362637A patent/ES362637A1/es not_active Expired
- 1969-01-17 BE BE727043D patent/BE727043A/xx unknown
- 1969-01-18 JP JP44003753A patent/JPS4937031B1/ja active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2682377A1 (fr) * | 1991-10-11 | 1993-04-16 | Atochem | Stabilisation du 1,1-dichloro-1-fluoroethane. |
| EP0538085A1 (fr) * | 1991-10-11 | 1993-04-21 | Elf Atochem S.A. | Stabilisation du 1,1-dichloro-1-fluoroéthane |
Also Published As
| Publication number | Publication date |
|---|---|
| NL6900516A (en, 2012) | 1969-07-22 |
| SU374809A3 (en, 2012) | 1973-03-20 |
| FR2000367A1 (en, 2012) | 1969-09-05 |
| BE727043A (en, 2012) | 1969-07-17 |
| US3627834A (en) | 1971-12-14 |
| BR6905677D0 (pt) | 1973-01-16 |
| JPS4937031B1 (en, 2012) | 1974-10-04 |
| ES362637A1 (es) | 1970-11-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| SH | Request for examination between 03.10.1968 and 22.04.1971 |