DE1618178B2 - Process for the production of high-purity zinc salts of higher fatty acids - Google Patents
Process for the production of high-purity zinc salts of higher fatty acidsInfo
- Publication number
- DE1618178B2 DE1618178B2 DE19671618178 DE1618178A DE1618178B2 DE 1618178 B2 DE1618178 B2 DE 1618178B2 DE 19671618178 DE19671618178 DE 19671618178 DE 1618178 A DE1618178 A DE 1618178A DE 1618178 B2 DE1618178 B2 DE 1618178B2
- Authority
- DE
- Germany
- Prior art keywords
- zinc
- fatty acid
- zinc salts
- fatty acids
- production
- 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.)
- Withdrawn
Links
- 235000014113 dietary fatty acids Nutrition 0.000 title claims description 21
- 229930195729 fatty acid Natural products 0.000 title claims description 21
- 239000000194 fatty acid Substances 0.000 title claims description 21
- 150000004665 fatty acids Chemical class 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 150000003751 zinc Chemical class 0.000 title description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 22
- -1 fatty acid zinc salts Chemical class 0.000 claims description 18
- 239000011787 zinc oxide Substances 0.000 claims description 11
- UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 claims description 10
- 229940007718 zinc hydroxide Drugs 0.000 claims description 10
- 229910021511 zinc hydroxide Inorganic materials 0.000 claims description 10
- 239000003960 organic solvent Substances 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 150000004670 unsaturated fatty acids Chemical class 0.000 claims description 3
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims description 3
- 150000004671 saturated fatty acids Chemical class 0.000 claims description 2
- 235000003441 saturated fatty acids Nutrition 0.000 claims 1
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 5
- 229920001169 thermoplastic Polymers 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000004416 thermosoftening plastic Substances 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 235000021588 free fatty acids Nutrition 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 3
- 235000021355 Stearic acid Nutrition 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 230000001050 lubricating effect Effects 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical group CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 2
- 229960001763 zinc sulfate Drugs 0.000 description 2
- 229910000368 zinc sulfate Inorganic materials 0.000 description 2
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/003—Compounds containing elements of Groups 2 or 12 of the Periodic Table without C-Metal linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/41—Preparation of salts of carboxylic acids
- C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Die Erfindung betrifft ein Verfahren zur Herstellung von hochreinen Zinksalzen höherer gesättigter oder ungesättigter Fettsäuren, bei dem man Zinkoxid oder Zinkhydroxid mit der entsprechenden Fettsäure in einem indifferenten organischen Lösungsmittel umsetzt.The invention relates to a process for the production of high-purity zinc salts of higher saturation or unsaturated fatty acids, in which zinc oxide or zinc hydroxide is combined with the corresponding fatty acid reacted in an inert organic solvent.
Fettsaure Zinksalze sind häufig verwendete Zusätze zu thermoplastischen Kunststoffen aller Art. Vor allem bei der Formgebung, beispielsweise wenn man aus einem granulatförmigen thermoplastischen Kunstrohstoff, wie Polyvinylchlorid, Polystyrol, Polyäthylen, Polyformaldehyd, Polyacetobutyrat, Polyamid, unvulkanisiertem Kautschuk usw. nach dem Spritzguß-, Strangpreß- oder Extrusionsverfahren Fertigteile herstellen will, macht man von der Schmier- und Formtrennwirkung und von den die Temperatur- und Alterungsstabilität verbessernden Eigenschaften der fettsauren Zinksalze Gebrauch. Ferner werden fettsaure Zinksalze als Dispergiermittel beim Einfärben von thermoplastischen Kunststoffen mit organischen oder anorganischen Pigmenten verwendet.Fatty acid zinc salts are frequently used additives to all kinds of thermoplastics. Especially when it comes to shaping, for example when one is made from a granular thermoplastic Plastic, such as polyvinyl chloride, polystyrene, polyethylene, polyformaldehyde, polyacetobutyrate, polyamide, unvulcanized rubber, etc. by injection molding, extrusion or extrusion processes Want to manufacture finished parts, one makes of the lubricating and mold release effect and of the Use of fatty acid zinc salts to improve temperature and aging stability. Fatty acid zinc salts are also used as dispersants when coloring thermoplastics used with organic or inorganic pigments.
Es ist bekannt, fettsaure Zinksalze herzustellen, indem man stöchiometrische Mengen von Zinkoxid oder Zinkhydroxid und freien Fettsäuren so hoch erhitzt, daß eine homogene Schmelze entsteht. Bei der dabei stattfindenden Reaktion bildet sich das fettsaure Zinksalz und die stöchiometrische Menge Wasser, das durch Verdampfen aus dem Reaktionsgemisch entfernt wird. Weiter können fettsaure Zinksalze hergestellt werden, indem man eine auf über 70° C erhitzte wäßrige Lösung eines fettsauren Natriumsalzes mit einem wasserlöslichen Zinksalz, z. B. Zinksulfat, umsetzt und das ausfallende fettsaure Zinksalz mechanisch durch Filtrieren oder Zentrifugieren abtrennt und anschließend einem Wasch- und Trockenprozeß unterwirft.It is known to produce fatty acid zinc salts by adding stoichiometric amounts of zinc oxide or zinc hydroxide and free fatty acids are heated so high that a homogeneous melt is formed. at the reaction taking place forms the fatty acid zinc salt and the stoichiometric amount of water, which is removed from the reaction mixture by evaporation. Fatty acid zinc salts can also be used be prepared by adding an aqueous solution of a fatty acid sodium salt heated to above 70.degree with a water soluble zinc salt, e.g. B. zinc sulfate, and the precipitating fatty acid Zinc salt is mechanically separated by filtration or centrifugation and then a washing and Subjects to drying process.
Zur Erzielung der gewünschten Fofmtrenn- und Schmierwirkung bei der Verarbeitung thermoplastischer Kunststoffe ist eine bestimmte Konzentration an derartigen fettsauren Zinksalzen in den Formmassen erforderlich.To achieve the desired film separating and lubricating effect when processing thermoplastics Plastics has a certain concentration of such fatty acid zinc salts in the molding compounds necessary.
Es zeigte sich nun, daß die nach den bekannten Verfahren hergestellten fettsauren Zinksalze noch einen merklichen Gehalt an störenden Verunreinigungen, wie nicht umgesetztes Zinkoxid, Zinkhydroxid oder freie Fettsäure sowie Einschlüsse von Natriumsulfat, Zinksulfat oder fettsaurem Natriumsalz enthalten, die die optische Klarheit glasklarer Kunststoffe sowie deren Thermostabilität während der thermoplastischen Verarbeitung zu Formteilen erheblich beeinträchtigen. Maßnahmen zur Erhöhung des Reinheitsgrads derart hergestellter fettsaurer Zinksalze sind zwar möglich, sie erfordern jedoch einen erheblichen technischen Aufwand.It has now been found that the fatty acid zinc salts prepared by the known processes are still a noticeable content of disruptive impurities, such as unreacted zinc oxide, zinc hydroxide or free fatty acid as well as inclusions of sodium sulfate, zinc sulfate or fatty acid sodium salt contain the optical clarity of crystal clear plastics as well as their thermal stability during significantly affect thermoplastic processing into molded parts. Measures to increase the degree of purity of fatty acid zinc salts produced in this way are possible, but require a considerable technical effort.
Es wurde nun gefunden, daß man die genannten Nachteile vermeiden und auf einfache Weise Zinksalze höherer Fettsäuren mit hoher Reinheit und hoo her Ausbeute herstellen kann, wenn man einen Überschuß von Zinkoxid oder Zinkhydroxid mit einer gesättigten oder ungesättigten Fettsäure mit 12 bis 24 Kohlenstoffatomen in Gegenwart eines indifferenten organischen Lösungsmittels bei Temperaturen zwischen 100 und 150° C umsetzt.It has now been found that the disadvantages mentioned can be avoided and zinc salts can be used in a simple manner higher fatty acids with high purity and high yield can be produced if you use an excess of zinc oxide or zinc hydroxide with a saturated or unsaturated fatty acid with 12 to 24 carbon atoms in the presence of an inert organic solvent at temperatures between 100 and 150 ° C converts.
Zinkoxid bzw. Zinkhydroxid ist im Reaktionsgemisch vorteilhaft in einem 2- bis 10%igem, insbesondere 4- bis 6e/oigen Überschuß, bezogen auf die molare Menge der verwendeten Fettsäure, enthalten. Als Fettsäuren gemäß vorliegender Erfindung eignen sich gesättigte und ungesättigte Monocarbonsäuren mit 12 bis 24 Kohlenstoffatomen, wie Stearinsäure und Palmitinsäure sowie deren Gemische.Zinc oxide or zinc hydroxide is advantageously contained in the reaction mixture in a 2 to 10%, in particular 4 to 6 e / o, excess, based on the molar amount of the fatty acid used. Suitable fatty acids according to the present invention are saturated and unsaturated monocarboxylic acids having 12 to 24 carbon atoms, such as stearic acid and palmitic acid and mixtures thereof.
Die Umsetzung wird besonders vorteilhaft bei der Siedetemperatur des Lösungsmittels unter den jeweils herrschenden Druckbedingungen vorgenommen, da hierbei das bei der Umsetzung entstehende Wasser leicht durch Destillation entfernt werden kann.The reaction is particularly advantageous at the boiling point of the solvent below each made under the prevailing pressure conditions, since this is the result of the implementation Water can be easily removed by distillation.
Nach dem erfindungsgemäßen Verfahren wird das im indifferenten organischen Lösungsmittel unlösliche, nicht umgesetzte Zinkoxid oder Zinkhydroxid mechanisch entfernt, z. B. durch Filtration oder Zentrifugation, während die nicht umgesetzte freie Fettsäure beim Abkühlen des Reaktionsgemische in Lösung bleibt und so bei der Isolierung des fettsauren Zinksalzes mit dem Lösungsmittel entfernt wird.According to the process according to the invention, the insoluble in the inert organic solvent, unreacted zinc oxide or zinc hydroxide mechanically removed, e.g. B. by filtration or centrifugation, while the unreacted free fatty acid on cooling the reaction mixture in solution remains and is removed with the solvent during the isolation of the fatty acid zinc salt.
Das bei der Reaktion freiwerdende Wasser kann durch Abscheiden oder durch Abdestillieren aus dem Gemisch entfernt werden.The water released during the reaction can be separated off or distilled off from the Mixture are removed.
Als indifferente organische Lösungsmittel sind besonders aromatische Kohlenwasserstoffe geeignet, die bei Raumtemperatur flüssig sind und deren Siedetemperatur zwischen 100 und 150° C liegt, z. B. Toluol, Xylole, Äthylbenzol, Propyl- und Isopropylbenzol usw. Die Löslichkeit der fettsauren Zinksalze beträgt im Bereich der Reaktionstemperatur ein Vielfaches der Löslichkeit bei Raumtemperatur. Zinkoxid und Zinkhydroxid sind sowohl bei der Reaktionstemperatur als auch bei Raumtemperatur in den Lösungsmitteln weitgehend unlöslich.Aromatic hydrocarbons are particularly suitable as inert organic solvents are liquid at room temperature and their boiling point is between 100 and 150 ° C, z. B. toluene, Xylenes, ethylbenzene, propyl- and isopropylbenzene etc. The solubility of the fatty acid zinc salts in the range of the reaction temperature is a multiple of the solubility at room temperature. zinc oxide and zinc hydroxide are in both the reaction temperature and room temperature Solvents largely insoluble.
Die in dem Beispiel genannten Teile sind Gewichtsteile. The parts mentioned in the example are parts by weight.
31,9 Teile Zinkoxid, 213 Teile Stearinsäure, 0,15 Teile p-Toluolsulfonsäure werden in 240 Teile Äthylbenzol eingerührt und die Mischung anschließend auf die Siedetemperatur des Äthylbenzols (etwa 136° C)31.9 parts of zinc oxide, 213 parts of stearic acid, 0.15 part of p-toluenesulfonic acid are dissolved in 240 parts of ethylbenzene stirred in and the mixture then brought to the boiling point of ethylbenzene (about 136 ° C)
erhitzt. Man hält das Reaktionsgemisch 20 Minuten bei dieser Temperatur, kondensiert die Äthylbenzoldämpfe mittels eines Rückflußkühlers und zieht das während der Reaktion entstandene mitgeführte Wasser über einen Abscheider seitlich ab. Danach verdünnt man das Reaktionsgemisch mit 712 Teilen Äthylbenzol und filtriert die in der Hitze ungelösten Restbestandteile ab, die vornehmlich aus Zinkoxid oder Zinkhydroxid bestehen. Nach Abkühlen desheated. The reaction mixture is kept at this temperature for 20 minutes and the ethylbenzene vapors are condensed by means of a reflux condenser and draws the water entrained during the reaction from the side via a separator. The reaction mixture is then diluted with 712 parts Ethylbenzene and filters off the residual constituents undissolved in the heat, mainly zinc oxide or zinc hydroxide. After the
3 43 4
zunächst noch klären Filtrats auf eine Temperatur Das Zinkstearat war kristallin und hatte einen scharunter 40° C fällt das gebildete Zinkstearat aus, das fen Schmelzpunkt von 127° C. Die Analyse ergab durch Filtration isoliert wird. Nach einem anschlie- 10,6% Zn (theor. 10,34% Zn). Nicht umgesetzte ßenden Trockenprozeß erhält man 230 Teile hoch- Ausgangssubstanzen sowie andere störende Verunreines Zinkstearat, das sind etwa 97% der Theorie. 5 reinigungen konnten nicht nachgewiesen werden.First of all, the filtrate should be cleared to a temperature. The zinc stearate was crystalline and had a sharp edge The zinc stearate formed precipitates at 40 ° C. and has a melting point of 127 ° C. The analysis showed is isolated by filtration. After a subsequent 10.6% Zn (theor. 10.34% Zn). Not implemented ßenden drying process one receives 230 parts high starting substances and other disruptive impurities Zinc stearate, that's about 97% of theory. 5 cleanings could not be verified.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB0093076 | 1967-06-19 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1618178A1 DE1618178A1 (en) | 1970-12-10 |
| DE1618178B2 true DE1618178B2 (en) | 1975-06-19 |
Family
ID=6986751
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19671618178 Withdrawn DE1618178B2 (en) | 1967-06-19 | 1967-06-19 | Process for the production of high-purity zinc salts of higher fatty acids |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1618178B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0061308A1 (en) * | 1981-03-19 | 1982-09-29 | Takeda Chemical Industries, Ltd. | Indancarboxylic acid zinc salts and production thereof |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2616814A (en) * | 1949-09-30 | 1952-11-04 | Mahler Paul | Composition of calcium salts of tall oil and a method of making it |
| US2945051A (en) * | 1955-10-19 | 1960-07-12 | American Cyanamid Co | Metallic salts of commercial stearic acid |
| NL269887A (en) * | 1960-10-04 | |||
| US3255223A (en) * | 1962-10-29 | 1966-06-07 | Yardney International Corp | Method of preparing stable silvercontaining compositions |
-
1967
- 1967-06-19 DE DE19671618178 patent/DE1618178B2/en not_active Withdrawn
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0061308A1 (en) * | 1981-03-19 | 1982-09-29 | Takeda Chemical Industries, Ltd. | Indancarboxylic acid zinc salts and production thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1618178A1 (en) | 1970-12-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8281 | Inventor (new situation) |
Free format text: GUENTHER, WOLFGANG, DR., 6700 LUDWIGSHAFEN, DE MOSTHAF, HELMUT, DR., 6702 BAD DUERKHEIM, DE MUECKE,GERD, DR., 6700 LUDWIGSHAFEN, DE |
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| 8230 | Patent withdrawn |