DE19950496A1 - Nano-particle concentrate production comprises ultra-filtering aqueous or alcoholic dispersion of specific average particle diameter and separating into permeate and retentate - Google Patents
Nano-particle concentrate production comprises ultra-filtering aqueous or alcoholic dispersion of specific average particle diameter and separating into permeate and retentateInfo
- Publication number
- DE19950496A1 DE19950496A1 DE19950496A DE19950496A DE19950496A1 DE 19950496 A1 DE19950496 A1 DE 19950496A1 DE 19950496 A DE19950496 A DE 19950496A DE 19950496 A DE19950496 A DE 19950496A DE 19950496 A1 DE19950496 A1 DE 19950496A1
- Authority
- DE
- Germany
- Prior art keywords
- acid
- dispersions
- nanoparticles
- ultrafiltration
- derivatives
- 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- Withdrawn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
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- 239000006185 dispersion Substances 0.000 title claims abstract description 20
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- 239000012141 concentrate Substances 0.000 title claims abstract description 8
- 239000012466 permeate Substances 0.000 title claims abstract description 5
- 230000001476 alcoholic effect Effects 0.000 title claims abstract description 4
- 239000012465 retentate Substances 0.000 title claims abstract description 4
- 238000004519 manufacturing process Methods 0.000 title abstract description 7
- 238000001914 filtration Methods 0.000 title abstract description 3
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- 238000000034 method Methods 0.000 claims description 22
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- 239000011769 retinyl palmitate Substances 0.000 description 1
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 1
- 229960003656 ricinoleic acid Drugs 0.000 description 1
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 1
- ALABRVAAKCSLSC-UHFFFAOYSA-N rutin Natural products CC1OC(OCC2OC(O)C(O)C(O)C2O)C(O)C(O)C1OC3=C(Oc4cc(O)cc(O)c4C3=O)c5ccc(O)c(O)c5 ALABRVAAKCSLSC-UHFFFAOYSA-N 0.000 description 1
- 235000005493 rutin Nutrition 0.000 description 1
- 229960000581 salicylamide Drugs 0.000 description 1
- 239000001691 salvia sclarea Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000003001 serine protease inhibitor Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- KZJWDPNRJALLNS-VJSFXXLFSA-N sitosterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CC[C@@H](CC)C(C)C)[C@@]1(C)CC2 KZJWDPNRJALLNS-VJSFXXLFSA-N 0.000 description 1
- 229950005143 sitosterol Drugs 0.000 description 1
- 235000015500 sitosterol Nutrition 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 229960004274 stearic acid Drugs 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- LGJMUZUPVCAVPU-HRJGVYIJSA-N stigmastanol Chemical compound C([C@@H]1CC2)[C@@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@H](C)CC[C@@H](CC)C(C)C)[C@@]2(C)CC1 LGJMUZUPVCAVPU-HRJGVYIJSA-N 0.000 description 1
- 235000016831 stigmasterol Nutrition 0.000 description 1
- ARCJQKUWGAZPFX-UHFFFAOYSA-N stilbene oxide Chemical compound O1C(C=2C=CC=CC=2)C1C1=CC=CC=C1 ARCJQKUWGAZPFX-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 150000001629 stilbenes Chemical class 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 125000005555 sulfoximide group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- CXVGEDCSTKKODG-UHFFFAOYSA-N sulisobenzone Chemical compound C1=C(S(O)(=O)=O)C(OC)=CC(O)=C1C(=O)C1=CC=CC=C1 CXVGEDCSTKKODG-UHFFFAOYSA-N 0.000 description 1
- 230000000475 sunscreen effect Effects 0.000 description 1
- 239000000516 sunscreening agent Substances 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 235000013616 tea Nutrition 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 229940116411 terpineol Drugs 0.000 description 1
- 229960002663 thioctic acid Drugs 0.000 description 1
- 235000019303 thiodipropionic acid Nutrition 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 229940094937 thioredoxin Drugs 0.000 description 1
- 108060008226 thioredoxin Proteins 0.000 description 1
- 239000001585 thymus vulgaris Substances 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 229940042585 tocopherol acetate Drugs 0.000 description 1
- 125000002640 tocopherol group Chemical class 0.000 description 1
- 235000019149 tocopherols Nutrition 0.000 description 1
- AQWHMKSIVLSRNY-UHFFFAOYSA-N trans-Octadec-5-ensaeure Natural products CCCCCCCCCCCCC=CCCCC(O)=O AQWHMKSIVLSRNY-UHFFFAOYSA-N 0.000 description 1
- BJIOGJUNALELMI-UHFFFAOYSA-N trans-isoeugenol Natural products COC1=CC(C=CC)=CC=C1O BJIOGJUNALELMI-UHFFFAOYSA-N 0.000 description 1
- ZCIHMQAPACOQHT-ZGMPDRQDSA-N trans-isorenieratene Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/c1c(C)ccc(C)c1C)C=CC=C(/C)C=Cc2c(C)ccc(C)c2C ZCIHMQAPACOQHT-ZGMPDRQDSA-N 0.000 description 1
- LOIYMIARKYCTBW-OWOJBTEDSA-N trans-urocanic acid Chemical compound OC(=O)\C=C\C1=CNC=N1 LOIYMIARKYCTBW-OWOJBTEDSA-N 0.000 description 1
- LOIYMIARKYCTBW-UHFFFAOYSA-N trans-urocanic acid Natural products OC(=O)C=CC1=CNC=N1 LOIYMIARKYCTBW-UHFFFAOYSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- NWKBFCIAPOSTKG-UHFFFAOYSA-M trimethyl-[3-[(3-methyl-5-oxo-1-phenyl-4h-pyrazol-4-yl)diazenyl]phenyl]azanium;chloride Chemical compound [Cl-].CC1=NN(C=2C=CC=CC=2)C(=O)C1N=NC1=CC=CC([N+](C)(C)C)=C1 NWKBFCIAPOSTKG-UHFFFAOYSA-M 0.000 description 1
- RYYVLZVUVIJVGH-UHFFFAOYSA-N trimethylxanthine Natural products CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 229940040064 ubiquinol Drugs 0.000 description 1
- QNTNKSLOFHEFPK-UPTCCGCDSA-N ubiquinol-10 Chemical compound COC1=C(O)C(C)=C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)C(O)=C1OC QNTNKSLOFHEFPK-UPTCCGCDSA-N 0.000 description 1
- 229940035936 ubiquinone Drugs 0.000 description 1
- 238000013060 ultrafiltration and diafiltration Methods 0.000 description 1
- 229960002703 undecylenic acid Drugs 0.000 description 1
- 229940116269 uric acid Drugs 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 235000019155 vitamin A Nutrition 0.000 description 1
- 239000011719 vitamin A Substances 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- 229940045997 vitamin a Drugs 0.000 description 1
- 238000004804 winding Methods 0.000 description 1
- ZFNVDHOSLNRHNN-UHFFFAOYSA-N xi-3-(4-Isopropylphenyl)-2-methylpropanal Chemical compound O=CC(C)CC1=CC=C(C(C)C)C=C1 ZFNVDHOSLNRHNN-UHFFFAOYSA-N 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
- OENHQHLEOONYIE-JLTXGRSLSA-N β-Carotene Chemical compound CC=1CCCC(C)(C)C=1\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C OENHQHLEOONYIE-JLTXGRSLSA-N 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D61/00—Processes of separation using semi-permeable membranes, e.g. dialysis, osmosis or ultrafiltration; Apparatus, accessories or auxiliary operations specially adapted therefor
- B01D61/14—Ultrafiltration; Microfiltration
- B01D61/145—Ultrafiltration
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D61/00—Processes of separation using semi-permeable membranes, e.g. dialysis, osmosis or ultrafiltration; Apparatus, accessories or auxiliary operations specially adapted therefor
- B01D61/14—Ultrafiltration; Microfiltration
- B01D61/145—Ultrafiltration
- B01D61/146—Ultrafiltration comprising multiple ultrafiltration steps
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D61/00—Processes of separation using semi-permeable membranes, e.g. dialysis, osmosis or ultrafiltration; Apparatus, accessories or auxiliary operations specially adapted therefor
- B01D61/14—Ultrafiltration; Microfiltration
- B01D61/16—Feed pretreatment
Abstract
Description
Die Erfindung befindet sich auf dem Gebiet der Nanopartikel und betrifft ein neues Verfahren zur Auf konzentrierung und Reinigung entsprechender Dispersionen.The invention is in the field of nanoparticles and relates to a new method for opening Concentration and cleaning of appropriate dispersions.
Die Herstellung von Wirkstoffen mit besonders kleiner Teilchengrößen, sogenannten "Nanoteilchen" gehört derzeit zu einem der expandierensten Forschungsthemen. Zur Herstellung sowohl anorgani scher als auch organischer Nanopartikel sind inzwischen die unterschiedlichsten Verfahren bekannt. Stellvertretend für den umfangreichen Stand der Technik sei auf den Aufsatz von S. Chihlar, M. Türk und K. Schaber in Proceedings World Congress on Particle Technology 3, Brighton, 1998 verwiesen, in welchem vorgeschlagen wird, Nanoteilchen durch rasche Entspannung von überkritischen Lösungen (Rapid Expansion of Supercritical Solutions RESS) herzustellen. Bei diesem Verfahren löst man bei spielsweise Cholesterin in überkritischem Kohlendioxid und entspannt die Lösung in eine Vakuum kammer. Im Zuge der geschilderten Verfahren werden jedoch infolge der Mitverwendung von Lö sungsmitteln stets mehr oder minder verdünnte Zubereitungen erhalten, die sich nicht ohne weiteres, d. h. ohne Zusammenbacken der Teilchen auf eine für die Anwendung erforderliche Konzentration an reichern lassen.The production of active substances with particularly small particle sizes, so-called "nanoparticles" is currently one of the most expanding research topics. To produce both inorganic In the meantime, a wide variety of processes are known both from shear and organic nanoparticles. The article by S. Chihlar, M. Türk and. Is representative of the extensive state of the art K. Schaber in Proceedings World Congress on Particle Technology 3, Brighton, 1998, in which is proposed, nanoparticles by rapid relaxation of supercritical solutions (Rapid Expansion of Supercritical Solutions RESS). With this method one solves for example cholesterol in supercritical carbon dioxide and relaxes the solution in a vacuum chamber. In the course of the described procedures, however, due to the co-use of Lö always receive more or less diluted preparations that are not easily d. H. to a concentration required for the application without caking of the particles let enrich.
Die Aufgabe der vorliegenden Erfindung hat folglich darin bestanden, ein Verfahren zur Verfügung zu stellen, mit dessen Hilfe man Nanopartikel-Dispersionen in hoher Ausbeute aufkonzentrieren kann, ohne daß es zu einer Re-Agglomeration kommt. Gleichzeitig sollte eine selektive Entfernung von ein- oder mehrwertigen Salzen erzielt werden. The object of the present invention was therefore to provide a method with the help of which nanoparticle dispersions can be concentrated in high yield, without re-agglomeration. At the same time, selective removal of or multivalent salts.
Gegenstand der Erfindung ist ein Verfahren zur Herstellung von Nanopartikelkonzentraten, bei dem man wäßrige oder alkoholische, gegebenenfalls salzhaltige Dispersionen von Nanopartikeln mit einem mittleren Durchmesser von 10 bis 200, vorzugsweise 25 bis 150 und insbesondere 50 bis 100 nm min destens einer Ultrafiltration unterwirft und dabei in ein verdünntes, gegebenenfalls Salze enthaltendes Permeat und ein Retentat getrennt wird, welches mindestens 90% der eingesetzten Nanopartikel ent hält.The invention relates to a method for producing nanoparticle concentrates, in which aqueous or alcoholic, optionally salt-containing dispersions of nanoparticles with a average diameter of 10 to 200, preferably 25 to 150 and in particular 50 to 100 nm min subject to ultrafiltration and thereby into a dilute, optionally containing salts Permeate and a retentate is separated, which ent ent least 90% of the nanoparticles used holds.
Überraschenderweise wurde gefunden, daß sich im Sinne des erfindungsgemäßen Verfahrens agglo merationsfrei Nanopartikelkonzentrate erhalten lassen, die zudem praktisch salzfrei sind. Das Verfah ren kommt ohne die Mitverwendung von Trennhilfsstoffen aus, arbeitet bei moderaten Temperaturen und ist dabei technisch einfach, wenig energieaufwendig und ausgesprochen effektiv.Surprisingly, it was found that agglomerate in the sense of the inventive method Meration-free nanoparticle concentrates are obtained, which are also practically salt-free. The procedure ren works without the use of release aids, works at moderate temperatures and is technically simple, requires little energy and is extremely effective.
Als anorganische Nanopartikel kommen grundsätzlich alle Arten von Oxiden, Hydroxiden und Salzen in Frage. Insbesondere geeignet sind anorganische Pigmente, wie sie u. a. als Farbstoffe im Bereich der dekorativen Kosmetik oder aber als UV-Filter für Sonnenschutzmittel eingesetzt werden. Als Farbstoffe finden Weißpigmente wie Talkum, Zinkoxid, Kaolin, Titandioxid oder Farbpigmente wie Eisenoxide, Chromoxide, Ultramann und Manganviolett Anwendung. Außerdem werden häufig noch Pigmente wie Bismutoxychlorid, Glimmer, mit Titandioxid beschichteter Glimmer und Fischsilber eingesetzt, die einen Perlglanz erzeugen. Beispiele für geeignete Metalloxide sind insbesondere Zinkoxid und Titandioxid und daneben Oxide des Eisens, Zirkoniums, Siliciums, Mangans, Aluminiums und Cers sowie deren Gemische. Als Salze können Silicate (Talk), Bariumsulfat oder Zinkstearat eingesetzt werden. Für An wendungen im Bereich der Schmierstoffe und Kunststoffhilfsmittel eignen sich auch Schwefel sowie Mineralien, vorzugsweise Hydrotalcit als Ausgangsstoffe für die Nanoisierung.In principle, all types of oxides, hydroxides and salts come in as inorganic nanoparticles Question. Inorganic pigments such as u. a. as dyes in the field of decorative cosmetics or as a UV filter for sunscreens. As dyes find white pigments such as talc, zinc oxide, kaolin, titanium dioxide or color pigments such as iron oxides, Chromium oxides, ultraman and manganese violet application. In addition, pigments such as Bismuth oxychloride, mica, titanium dioxide coated mica and fish silver are used Create pearlescent. Examples of suitable metal oxides are, in particular, zinc oxide and titanium dioxide and in addition oxides of iron, zirconium, silicon, manganese, aluminum and cerium and their Mixtures. Silicates (talc), barium sulfate or zinc stearate can be used as salts. For An Applications in the field of lubricants and plastic additives are also suitable for sulfur as well Minerals, preferably hydrotalcite as raw materials for nanoization.
Als organische Nanopartikel, die im Sinne des erfindungsgemäßen Verfahrens aufkonzentriert und gereinigt werden können, kommen folgende Verbindungen in Betracht:As organic nanoparticles, which are concentrated and The following compounds can be cleaned:
Sterole (oder synonym Stenole) sind tierische bzw. pflanzliche Steroide zu verstehen, die nur am C-3
eine Hydroxylgruppe, sonst aber keine funktionellen Gruppen tragen. In der Regel besitzen die Sterole
27 bis 30 Kohlenstoffatome und eine Doppelbindung in 5/6, gegebenenfalls 7/8, 8/9 oder anderen Po
sitionen. Neben diesen ungesättigten Spezies kommen als Sterole auch die durch Härtung erhältlichen
gesättigten Verbindungen in Frage, die als Stanole bezeichnet werden und von der vorliegenden Erfin
dung mitumschlossen werden. Ein Beispiel für ein geeignetes tierisches Sterol ist Cholesterol. Typische
Beispiele für geeignete Phytosterole, welche aus anwendungstechnischen Gründen bevorzugt werden,
sind beispielsweise Ergosterole, Campesterole, Stigmasterole, Brassica-sterole sowie vorzugsweise
Sitosterole bzw. Sitostanole und insbesondere β-Sitosterole bzw. β-Sitostanole. Neben den genannten
Phytosterolen werden vorzugsweise deren Ester eingesetzt. Die Säurekomponente der Esters kann auf
Carbonsäuren der Formel (I) zurückgehen,
Sterols (or synonym stenols) are animal or vegetable steroids to be understood which only carry a hydroxyl group at C-3, but no other functional groups. In general, the sterols have 27 to 30 carbon atoms and a double bond in 5/6, optionally 7/8, 8/9 or other positions. In addition to these unsaturated species, sterols also include the saturated compounds obtainable by curing, which are referred to as stanols and are included in the present invention. An example of a suitable animal sterol is cholesterol. Typical examples of suitable phytosterols, which are preferred for technical reasons, are, for example, ergosterols, campesterols, stigmasterols, brassica sterols and preferably sitosterols or sitostanols and in particular β-sitosterols or β-sitostanols. In addition to the phytosterols mentioned, their esters are preferably used. The acid component of the ester can be traced back to carboxylic acids of the formula (I)
R1CO-OH (I)
R 1 CO-OH (I)
in der R1CO für einen aliphatischen, linearen oder verzweigten Acylrest mit 2 bis 22 Kohlenstoffatomen und 0 und/oder 1, 2 oder 3 Doppelbindungen steht. Typische Beispiele sind Essigsäure, Propionsäure, Buttersäure, Valeriansäure, Capronsäure, Caprylsäure, 2-Ethylhexansäure, Caprinsäure, Laurinsäure, Isotridecansäure, Myristinsäure, Palmitinsäure, Palmoleinsäure, Stearinsäure, Isostearinsäure, Öl säure, Elaidinsäure, Petroselinsäure, Linolsäure, konjugierte Linolsäure (CLA), Linolensäure, Elaeo stearinsäure, Arachinsäure, Gadoleinsäure, Behensäure und Erucasäure sowie deren technische Mi schungen, die z. B. bei der Druckspaltung von natürlichen Fetten und Ölen, bei der Reduktion von Al dehyden aus der Roelen'schen Oxosynthese oder als Monomerfraktion bei der Dimerisierung von un gesättigten Fettsäuren anfallen. Bevorzugt sind technische Fettsäuren mit 12 bis 18 Kohlenstoffatomen wie beispielsweise Kokos-, Palm-, Palmkern- oder Talgfettsäure. Besonders bevorzugt ist der Einsatz von Estern des β-Sitosterols bzw. β-Sitostanols mit Fettsäuren mit 12 bis 18 Kohlenstoffatomen. Diese Ester können sowohl durch direkte Veresterung der Phytostenole mit den Fettsäuren oder aber durch Umesterung mit Fettsäureniedrigalkylestern oder Triglyceriden in Gegenwart geeigneter Katalysatoren, wie z. B. Natriumethylat oder speziell auch Enzymen hergestellt werden [vgl. EP-A2 0195311 (Yoshika wa)].in which R 1 CO represents an aliphatic, linear or branched acyl radical having 2 to 22 carbon atoms and 0 and / or 1, 2 or 3 double bonds. Typical examples are acid, acetic acid, propionic acid, butyric acid, valeric acid, caproic acid, caprylic acid, 2-ethylhexanoic acid, capric acid, lauric acid, isotridecanoic acid, myristic acid, palmitic acid, palmoleic acid, stearic acid, isostearic acid, oleic acid, elaidic acid, petroselinic acid, linoleic acid, conjugated linoleic acid (CLA), Linolenic acid, Elaeo stearic acid, arachic acid, gadoleic acid, behenic acid and erucic acid and their technical mixes, the z. B. in the splitting of natural fats and oils, in the reduction of Al dehyden from Roelen's oxosynthesis or as a monomer fraction in the dimerization of unsaturated fatty acids. Technical fatty acids with 12 to 18 carbon atoms such as coconut, palm, palm kernel or tallow fatty acid are preferred. The use of esters of β-sitosterol or β-sitostanol with fatty acids having 12 to 18 carbon atoms is particularly preferred. These esters can either by direct esterification of the phytostenols with the fatty acids or by transesterification with fatty acid lower alkyl esters or triglycerides in the presence of suitable catalysts, such as. B. sodium ethylate or specifically also enzymes [cf. EP-A2 0195311 (Yoshika wa)].
Typische Beispiele für Antioxidantien sind Aminosäuren (z. B. Glycin, Histidin, Tyrosin, Tryptophan) und deren Derivate, Imidazole (z. B. Urocaninsäure) und deren Derivate, Peptide wie D,L-Carnosin, D- Carnosin, L-Carnosin und deren Derivate (z. B. Anserin), Carotinoide, Carotine (z. B. α-Carotin, β- Carotin, Lycopin) und deren Derivate, Chlorogensäure und deren Derivate, Liponsäure und deren Deri vate (z. B. Dihydroliponsäure), Aurothioglucose, Propylthiouracil und andere Thiole (z. B. Thioredoxin, Glutathion, Cystein, Cystin, Cystamin und deren Glycosyl-, N-Acetyl-, Methyl-, Ethyl-, Propyl-, Amyl-, Butyl- und Lauryl-, Palmitoyl-, Oleyl-, γ-Linoleyl-, Cholesteryl- und Glycerylester) sowie deren Salze, Dilaurylthiodipropionat, Distearylthiodipropionat, Thiodipropionsäure und deren Derivate (Ester, Ether, Peptide, Lipide, Nukleotide, Nukleoside und Salze) sowie Sulfoximinverbindungen (z. B. Buthioninsulfo ximine, Nomocysteinsulfoximin, Butioninsulfone, Penta-, Hexa-, Heptathioninsulfoximin) in sehr gerin gen verträglichen Dosierungen (z. B. pmol bis µmol/kg), ferner (Metall)-Chelatoren (z. B. α- Hydroxyfettsäuren, Palmitinsäure, Phytinsäure, Lactoferrin), α-Hydroxysäuren (z. B. Citronensäure, Milchsäure, Apfelsäure), Huminsäure, Gallensäure, Gallenextrakte, Bilirubin, Biliverdin, EDTA, EGTA und deren Derivate, ungesättigte Fettsäuren und deren Derivate (z. B. γ-Linolensäure, Linolsäure, Öl säure), Folsäure und deren Derivate, Ubichinon und Ubichinol und deren Derivate, Vitamin C und Deri vate (z. B. Ascorbylpalmitat, Mg-Ascorbylphosphat, Ascorbylacetat), Tocopherole und Derivate (z. B. Vitamin-E-acetat), Vitamin A und Derivate (Vitamin-A-palmitat) sowie Koniferylbenzoat des Benzoe harzes, Rutinsäure und deren Derivate, α-Glycosylrutin, Ferulasäure, Furfurylidenglucitol, Carnosin, Butylhydroxytoluol, Butylhydroxyanisol, Nordihydroguajakharzsäure, Nordihydroguajaretsäure, Rosma rinsäure, Trihydroxybutyrophenon, Harnsäure und deren Derivate, Mannose und deren Derivate, Su peroxid-Dismutase, Zink und dessen Derivate (z. B. ZnO, ZnSO4) Selen und dessen Derivate (z. B. Se len-Methionin), Stilbene und deren Derivate (z. B. Stilbenoxid, trans-Stilbenoxid) und die erfindungs gemäß geeigneten Derivate (Salze, Ester, Ether, Zucker, Nukleotide, Nukleoside, Peptide und Lipide) dieser genannten Wirkstoffe.Typical examples of antioxidants are amino acids (e.g. glycine, histidine, tyrosine, tryptophan) and their derivatives, imidazoles (e.g. urocanic acid) and their derivatives, peptides such as D, L-carnosine, D-carnosine, L-carnosine and their derivatives (e.g. anserine), carotenoids, carotenes (e.g. α-carotene, β-carotene, lycopene) and their derivatives, chlorogenic acid and their derivatives, lipoic acid and their derivatives (e.g. dihydroliponic acid) , Aurothioglucose, propylthiouracil and other thiols (e.g. thioredoxin, glutathione, cysteine, cystine, cystamine and their glycosyl, N-acetyl, methyl, ethyl, propyl, amyl, butyl and lauryl, palmitoyl -, Oleyl, γ-linoleyl, cholesteryl and glyceryl esters) and their salts, dilauryl thiodipropionate, distearyl thiodipropionate, thiodipropionic acid and their derivatives (esters, ethers, peptides, lipids, nucleotides, nucleosides and salts) as well as sulfoximine compounds (e.g. buthioninsulfo ximine, Nomocysteinsulfoximin, Butioninsulfone, Penta-, Hexa-, Heptathio ninsulfoximine) in very low tolerable doses (e.g. B. pmol to µmol / kg), also (metal) chelators (e.g. α-hydroxy fatty acids, palmitic acid, phytic acid, lactoferrin), α-hydroxy acids (e.g. citric acid, lactic acid, malic acid), humic acid, bile acid, Bile extracts, bilirubin, biliverdin, EDTA, EGTA and their derivatives, unsaturated fatty acids and their derivatives (e.g. γ-linolenic acid, linoleic acid, oleic acid), folic acid and their derivatives, ubiquinone and ubiquinol and their derivatives, vitamin C and derivatives (e.g. ascorbyl palmitate, Mg ascorbyl phosphate, ascorbyl acetate), tocopherols and derivatives (e.g. vitamin E acetate), vitamin A and derivatives (vitamin A palmitate) and coniferyl benzoate of benzoin, rutinic acid and their derivatives , α-glycosyl rutin, ferulic acid, furfurylidene glucitol, carnosine, butylated hydroxytoluene, butylated hydroxyanisole, nordihydroguajak resin acid, nordihydroguajaretic acid, rosin acid, trihydroxybutyrophenone, uric acid and its derivatives, mannose and its derivatives, suase oxide and its derivatives (e.g. ZnO, ZnSO 4 ) selenium and its derivatives (e.g. B. Se len-methionine), stilbenes and their derivatives (z. B. stilbene oxide, trans-stilbene oxide) and the fiction, suitable derivatives (salts, esters, ethers, sugars, nucleotides, nucleosides, peptides and lipids) of these active ingredients.
Flavone, wie z. B. Flavon (Primel), Chrysin (Pappel), Galangin (Glagantwurzel), Apigenin (Löwenmaul, Kamille, Dahlie), Luteolin (Fingerhut, Dahlie), Kämpferol (Faulbaum, Rittersporn, Schlehen), Querutin (Eiche, Goldlack, Stiefmütterchen), Quercetin (Eiche, Goldlack, Stiefmütterchen), Morin (Maulbeer baum), Robinetin (Akazien), Gossynetin (Baumwolle, Hibiscus), Myricetin (Johannisbeere, Hama melis), Fisetin (Fisetholz), Rutin (Citrusfrüchte, Stiefmütterchen, Lindenblüten, Tee, Johanniskraut, Aka zien), Hesperidin (Orangenschalen), Naringin (Pampelmusen), Daidzein (Soja), Genistein (Soja, Rot klee), Prumetin (Pflaumenbaum), Biochanin (Kichererbse, Klee), Santal (Sandelholz, Rotholz), Praten sein (Klee), Bioflavonoide aus Gingko, Eibe und Zypresse.Flavones such as B. Flavon (primrose), chrysin (poplar), galangin (glagantroot), apigenin (snapdragon, Chamomile, dahlia), luteolin (foxglove, dahlia), fighter oil (rot tree, delphinium, sloes), quercutin (Oak, gold lacquer, pansies), quercetin (oak, gold lacquer, pansies), morin (mulberry tree), robinetin (acacia), gossynetin (cotton, hibiscus), myricetin (currant, hama melis), fisetin (fisetholz), rutin (citrus fruits, pansies, linden flowers, tea, St. John's wort, Aka zien), hesperidin (orange peel), naringin (grapefruit), daidzein (soy), genistein (soy, red clover), prumetin (plum tree), biochanin (chickpea, clover), santal (sandalwood, redwood), praten his (clover), bioflavonoids from gingko, yew and cypress.
Weiterhin können synthetische oder natürliche Wachse eingesetzt werden, wie z. B. Paraffinwachse, hydriertes. Ricinusöl, Cetylplamitat, Ethylenoxid-Wachse, Perlglanzwachse, Carnaubawachs, Bienen wachs, Sonnenblumenwachs und Apfelwachs.Furthermore, synthetic or natural waxes can be used, such as. B. paraffin waxes, hydrogenated. Castor oil, cetyl plasticity, ethylene oxide waxes, pearlescent waxes, carnauba wax, bees wax, sunflower wax and apple wax.
Ebenfalls als Ausgangsstoffe geeignet sind bei Raumtemperatur feste Fettsäuren und Fettalkohole mit 12 bis 22 Kohlenstoffatomen, wie z. B. Laurinsäure, Isotridecansäure, Myristinsäure, Palmitinsäure, Stearinsäure und Behensäure sowie deren technische Mischungen, bzw. Cetylalkohol, Palmoleylalko hol, Stearylalkohol und Behenylalkohol sowie deren technische Mischungen. Ebenfalls geeignet sind Mischungen der genannten Fettalkoholen mit Alkylpolyglucosiden, wobei Mischungen von Cetearylal kohol mit Cetearylglucosiden im Mischungsverhältnis 10 : 90 bis 90 : 10 besonders bevorzugt sind.Fatty acids and fatty alcohols that are solid at room temperature are also suitable as starting materials with 12 to 22 carbon atoms, such as. B. lauric acid, isotridecanoic acid, myristic acid, palmitic acid, Stearic acid and behenic acid and their technical mixtures, or cetyl alcohol, palmoleyl alcohol hol, stearyl alcohol and behenyl alcohol and their technical mixtures. Are also suitable Mixtures of the fatty alcohols mentioned with alkyl polyglucosides, mixtures of cetearylal alcohol with cetearyl glucosides in a mixing ratio of 10:90 to 90:10 are particularly preferred.
Als Ausgangsstoffe für das erfindungsgemäße Verfahren kommen auch Metallseifen in Frage, wie z. B. die Calcium-, Magnesium-, Aluminium- und/oder Zinksalze von Carbonsäuren mit 10 bis 18 Kohlen stoffatomen, insbesondere der Undecylensäure, Stearinsäure, Hydroxystearinsäure oder Ricinolsäure. Metal soaps are also suitable as starting materials for the process according to the invention, such as. B. the calcium, magnesium, aluminum and / or zinc salts of carboxylic acids with 10 to 18 carbons Substance atoms, especially undecylenic acid, stearic acid, hydroxystearic acid or ricinoleic acid.
Als Farbstoffe kommen dabei beispielsweise direktziehende Farbstoffe aus der Gruppe der Ni trophenylendiamine, Nitroaminophenole, Anthrachinone oder Indophenole in Betracht, wie z. B. die unter den internationalen Bezeichnungen bzw. Handelsnamen HC Yellow 2, HC Yellow 4, Basic Yellow 57, Disperse Orange 3, HC Red 3, HC Red BN, Basic Red 76, HC Blue 2, Disperse Blue 3, Basic Blue 99, HC Violet 1, Disperse Violet 1, Disperse Violet 4, Disperse Black 9, Basic Brown 16, Basic Brown 17, Pikraminsäure und Rodol 9 R bekannten Verbindungen sowie 4-Amino-2-nitrodiphenylamin-2'- carbonsäure, 6-Nitro-1,2,3,4-tetrahydrochinoxalin, (N-2,3-Dihydroxypropyl-2-nitro-4-trifluormethyl)-ami nobenzol und 4-N-Ethyl-1,4-bis(2'-hydroxyethylamino)-2-nitrobenzol-hydrochlorid. Weiterhin können auch in der Natur vorkommende Farbstoffe wie beispielsweise Henna rot, Henna neutral, Henna schwarz, Kamillenblüte, Sandelholz, schwarzer Tee, Faulbaumrinde, Salbei, Blauholz, Krappwurzel, Catechu, Sedre und Alkannawurzel sowie Indigo, Cochenille, Shikonin, Alizarin, Juglon und Hema toxilin verwendet werden. Alternativ lassen sich Oxidationsfarbstoffe einsetzen, die aus Entwickler- und Kupplerkomponente bestehen. Als Entwicklerkomponenten werden beispielsweise primäre aro matische Amine mit einer weiteren, in para- oder ortho-Position befindlichen freien oder substituierten Hydroxy- oder Aminogruppe, Diaminopyridinderivate, heterocyclische Hydrazone, 4-Aminopyrazolon derivate sowie 2,4,5,6-Tetraaminopyrimidin und dessen Derivate eingesetzt. Spezielle Vertreter sind u. a. p-Toluylendiamin, p-Aminophenol, N,N-Bis-(2-hydroxy-ethyl)-p-phenylendiamin, 2-(2,5-Diamino phenoxy)ethanol, 1-Phenyl-3-carboxyamido-4-amino-pyrazolon-5 und 4-Amino-3-methylphenol, 2-(2- Hydroxyethyl)-1,4-aminobenzol und 2,4,5,6-Tetraaminopyrimidin. Als Kupplerkomponenten werden in der Regel m-Phenylendiaminderivate, Naphthole, Resorcin und Resorcinderivate, Pyrazolone, m-Ami nophenole sowie Pyridin-Derivate verwendet. Als Kupplersubstanzen eignen sich insbesondere 1- Naphthol, Pyrogallol, 1,5-, 2,7- und 1,7-Dihydroxynaphthalin, 5-Amino-2-methylphenol, m-Aminophenol, Resorcin, Resorcinmonomethylether, m-Phenylendiamin, 1-Phenyl-3-methyl-pyrazolon-5, 2,4-Dichlor-3- aminophenol, 1,3-Bis-(2,4-diaminophenoxy)-propan, 2-Chlorresorcin, 2-Chlor-6-methyl-3-aminophenol, 2-Methylresorcin, 2,5-Dimethylresorcin, 2,6-Dihydroxypyridin und 2,6-Diaminopyridin. Des weiteren kön nen auch natürliche Farbpigmente aus Pflanzen, wie z. B. Chlorophylle, Carotine und Anthocyane ein gesetzt werden.Direct dyes from the group of Ni are used as dyes trophenylenediamines, nitroaminophenols, anthraquinones or indophenols, such as. B. the under the international names or trade names HC Yellow 2, HC Yellow 4, Basic Yellow 57, Disperse Orange 3, HC Red 3, HC Red BN, Basic Red 76, HC Blue 2, Disperse Blue 3, Basic Blue 99, HC Violet 1, Disperse Violet 1, Disperse Violet 4, Disperse Black 9, Basic Brown 16, Basic Brown 17, picramic acid and Rodol 9 R known compounds and 4-amino-2-nitrodiphenylamine-2'- carboxylic acid, 6-nitro-1,2,3,4-tetrahydroquinoxaline, (N-2,3-dihydroxypropyl-2-nitro-4-trifluoromethyl) -ami nobenzene and 4-N-ethyl-1,4-bis (2'-hydroxyethylamino) -2-nitrobenzene hydrochloride. Can continue also naturally occurring dyes such as henna red, henna neutral, henna black, chamomile flower, sandalwood, black tea, sapwood, sage, blue wood, madder root, Catechu, Sedre and Alkanna root as well as indigo, cochineal, shikonin, alizarin, juglon and hema toxin can be used. Alternatively, oxidation dyes can be used, which are made from developer and coupler component exist. For example, primary aro Matic amines with a further free or substituted one in the para or ortho position Hydroxy or amino group, diaminopyridine derivatives, heterocyclic hydrazones, 4-aminopyrazolone derivatives and 2,4,5,6-tetraaminopyrimidine and its derivatives used. Are special representatives u. a. p-toluenediamine, p-aminophenol, N, N-bis- (2-hydroxyethyl) -p-phenylenediamine, 2- (2,5-diamino phenoxy) ethanol, 1-phenyl-3-carboxyamido-4-amino-pyrazolon-5 and 4-amino-3-methylphenol, 2- (2- Hydroxyethyl) -1,4-aminobenzene and 2,4,5,6-tetraaminopyrimidine. As coupler components are in usually m-phenylenediamine derivatives, naphthols, resorcinol and resorcinol derivatives, pyrazolones, m-ami nophenols and pyridine derivatives are used. 1- are particularly suitable as coupler substances Naphthol, pyrogallol, 1,5-, 2,7- and 1,7-dihydroxynaphthalene, 5-amino-2-methylphenol, m-aminophenol, Resorcinol, resorcinol monomethyl ether, m-phenylenediamine, 1-phenyl-3-methyl-pyrazolon-5, 2,4-dichloro-3- aminophenol, 1,3-bis (2,4-diaminophenoxy) propane, 2-chlororesorcinol, 2-chloro-6-methyl-3-aminophenol, 2-methylresorcinol, 2,5-dimethylresorcinol, 2,6-dihydroxypyridine and 2,6-diaminopyridine. Furthermore, NEN also natural color pigments from plants, such as. B. chlorophylls, carotenes and anthocyanins be set.
Für die Herstellung von Nanopigmenten geeignete UV-Lichtschutzfaktoren sind z. B.Suitable UV light protection factors for the production of nanopigments are e.g. B.
- - 3-Benzylidencampher bzw. 3-Benzylidennorcampher und dessen Derivate, z. B. 3-(4-Methylben zyliden)campher wie in der EP-B1 0693471 beschrieben;- 3-benzylidene camphor or 3-benzylidene norcampher and its derivatives, e.g. B. 3- (4-Methylbene cylidene) camphor as described in EP-B1 0693471;
- - 4-Aminobenzoesäurederivate, vorzugsweise 4-(Dimethylamino)benzoesäure-2-ethylhexylester, 4- (Dimethylamino)benzoesäure-2-octylester und 4-(Dimethylamino)benzoesäureamylester;- 4-aminobenzoic acid derivatives, preferably 4- (dimethylamino) benzoic acid 2-ethylhexyl ester, 4- 2-octyl (dimethylamino) benzoate and amyl 4- (dimethylamino) benzoate;
- - Ester der Zimtsäure, vorzugsweise 4-Methoxyzimtsäure-2-ethylhexylester, 4-Methoxyzimtsäure propylester, 4-Methoxyzimtsäureisoamylester 2-Cyano-3,3-phenylzimtsäure-2-ethylhexylester (Oc tocrylene); - Esters of cinnamic acid, preferably 2-ethylhexyl 4-methoxycinnamate, 4-methoxycinnamic acid propyl ester, 4-methoxycinnamic acid isoamyl ester 2-cyano-3,3-phenylcinnamic acid 2-ethylhexyl ester (Oc tocrylene);
- - Ester der Salicylsäure, vorzugsweise Salicylsäure-2-ethylhexylester, Salicylsäure-4-isopropylben zylester, Salicylsäurehomomenthylester;- Esters of salicylic acid, preferably salicylic acid 2-ethylhexyl ester, salicylic acid 4-isopropylbene methyl ester, salicylic acid homomethyl ester;
- - Derivate des Benzophenons, vorzugsweise 2-Hydroxy-4-methoxybenzophenon, 2-Hydroxy-4-meth oxy-4'-methylbenzophenon, 2,2'-Dihydroxy-4-methoxybenzophenon;- Derivatives of benzophenone, preferably 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-meth oxy-4'-methylbenzophenone, 2,2'-dihydroxy-4-methoxybenzophenone;
- - Ester der Benzalmalonsäure, vorzugsweise 4-Methoxybenzmalonsäuredi-2-ethylhexylester;- Esters of benzalmalonic acid, preferably di-2-ethylhexyl 4-methoxybenzmalonate;
- - Triazinderivate, wie z. B. 2,4,6-Trianilino-(p-carbo-2'-ethyl-1'-hexyloxy)-1,3,5-triazin und Octyl Tria zon, wie in der EP-A10818450 beschrieben;- Triazine derivatives, such as. B. 2,4,6-Trianilino- (p-carbo-2'-ethyl-1'-hexyloxy) -1,3,5-triazine and octyl tria zon as described in EP-A10818450;
- - Propan-1,3-dione, wie z. B. 1-(4-tert.Butylphenyl)-3-(4'methoxyphenyl)propan-1,3-dion;Propane-1,3-diones, such as e.g. B. 1- (4-tert-butylphenyl) -3- (4'methoxyphenyl) propane-1,3-dione;
- - Ketotricyclo(5.2.1.0)decan-Derivate, wie in der EP-810694521 beschrieben.- Ketotricyclo (5.2.1.0) decane derivatives, as described in EP-810694521.
- - 2-Phenylbenzimidazol-5-sulfonsäure und deren Alkali-, Erdalkali-, Ammonium-, Alkylammonium-, Alkanolammonium- und Glucammoniumsalze;- 2-phenylbenzimidazole-5-sulfonic acid and its alkali, alkaline earth, ammonium, alkylammonium, Alkanolammonium and glucammonium salts;
- - Sulfonsäurederivate von Benzophenonen, vorzugsweise 2-Hydroxy-4-methoxybenzophenon-5-sul fonsäure und ihre Salze;- Sulfonic acid derivatives of benzophenones, preferably 2-hydroxy-4-methoxybenzophenone-5-sul fonic acid and its salts;
- - Sulfonsäurederivate des 3-Benzylidencamphers, wie z. B. 4-(2-Oxo-3-bornylidenmethyl)benzolsul fonsäure und 2-Methyl-5-(2-oxo-3-bornyliden)sulfonsäure und deren Salze.- Sulfonic acid derivatives of 3-benzylidene camphor, such as. B. 4- (2-Oxo-3-bornylidenemethyl) benzenesul fonic acid and 2-methyl-5- (2-oxo-3-bornylidene) sulfonic acid and their salts.
- - Benzoylmethanderivate, wie beispielsweise 1-(4'-tert.Butylphenyl)-3-(4'-methoxyphenyl)propan-1,3- dion, 4-tert.-Butyl-4'-methoxydibenzoyl-methan (Parsol 1789), oder 1-Phenyl-3-(4'-isopropylphenyl)- propan-1,3-dion.- Benzoylmethane derivatives, such as 1- (4'-tert-butylphenyl) -3- (4'-methoxyphenyl) propane-1,3- dione, 4-tert-butyl-4'-methoxydibenzoyl-methane (Parsol 1789), or 1-phenyl-3- (4'-isopropylphenyl) - propane-1,3-dione.
Weitere geeignete UV-Lichtschutzfilter sind der Übersicht von P. Finkel in SÖFW-Journal 122, 543 (1996) zu entnehmen.Other suitable UV light protection filters can be found in P. Finkel's overview in SÖFW-Journal 122, 543 (1996).
Des weiteren geeignete Einsatzstoffe sind Riechstoffe. Natürliche Riechstoffe sind Extrakte von Blüten (Lilie, Lavendel, Rosen, Jasmin, Neroli, Ylang-Ylang), Stengeln und Blättern (Geranium, Patchouli, Petitgrain), Früchten (Anis, Koriander, Kümmel, Wacholder), Fruchtschalen (Bergamotte, Zitrone, Orangen), Wurzeln (Macis, Angelica, Sellerie, Kardamon, Costus, Iris, Calmus), Hölzern (Pinien-, San del-, Guajak-, Zedern-, Rosenholz), Kräutern und Gräsern (Estragon, Lemongras, Salbei, Thymian), Nadeln und Zweigen (Fichte, Tanne, Kiefer, Latschen), Harzen und Balsamen (Galbanum, Elemi, Ben zoe, Myrrhe, Olibanum, Opoponax). Weiterhin kommen tierische Rohstoffe in Frage, wie beispiels weise Zibet und Castoreum. Typische synthetische Riechstoffverbindungen sind Produkte vom Typ der Ester, Ether, Aldehyde, Ketone, Alkohole und Kohlenwasserstoffe. Riechstoffverbindungen vom Typ der Ester sind z. B. Benzylacetat, Phenoxyethylisobutyrat, p-tert.-Butylcyclohexylacetat, Linalylacetat, Dimethylbenzylcarbinylacetat, Phenylethylacetat, Linalylbenzoat, Benzylformiat, Ethylmethylphenyl glycinat, Allylcyclohexylpropionat, Styrallylpropionat und Benzylsalicylat. Zu den Ethern zählen bei spielsweise Benzylethylether, zu den Aldehyden z. B. die linearen Alkanale mit 8 bis 18 Kohlenstoff atomen, Citral, Citronellal, Citronellyloxyacetaldehyd, Cyclamenaldehyd, Hydroxycitronellal, Lilial und Bourgeonal, zu den Ketonen z. B. die Jonone, α-Iso-methylionon und Methylcedrylketon, zu den Alko holen Anethol, Citronellol, Eugenol, Isoeugenol, Geraniol, Linalool, Phenylethylalkohol und Terpineol, zu den Kohlenwasserstoffen gehören hauptsächlich die Terpene und Balsame. Weiterhin geeignet sind Ambroxan, Heliotropin, Vanillin, Ethylvanillin, Cumann, Campher, Menthol, Indol und Maltol sowie die Extrakte von Reis, Reisschalen, Myrrhe, Olibanum, Mistel und Salvia Sclarea.Suitable starting materials are also fragrances. Natural fragrances are extracts from flowers (Lily, lavender, roses, jasmine, neroli, ylang-ylang), stems and leaves (geranium, patchouli, Petitgrain), fruits (anise, coriander, caraway, juniper), fruit peel (bergamot, lemon, Oranges), Roots (Macis, Angelica, Celery, Cardamom, Costus, Iris, Calmus), Woods (Pine, San del, guaiac, cedar, rosewood), herbs and grasses (tarragon, lemongrass, sage, thyme), Needles and twigs (spruce, fir, pine, mountain pines), resins and balms (Galbanum, Elemi, Ben zoe, myrrh, olibanum, opoponax). Animal raw materials are also possible, such as wise civet and castoreum. Typical synthetic fragrance compounds are products of the type Esters, ethers, aldehydes, ketones, alcohols and hydrocarbons. Fragrance compounds of the type the esters are e.g. B. benzyl acetate, phenoxyethyl isobutyrate, p-tert-butylcyclohexyl acetate, linalyl acetate, Dimethylbenzylcarbinylacetate, phenylethyl acetate, linalylbenzoate, benzyl formate, ethylmethylphenyl glycinate, allyl cyclohexyl propionate, styrallyl propionate and benzyl salicylate. The ethers include for example benzyl ethyl ether, to the aldehydes z. B. the linear alkanals with 8 to 18 carbon atoms, citral, citronellal, citronellyloxyacetaldehyde, cyclamenaldehyde, hydroxycitronellal, lilial and Bourgeonal, to the ketones z. B. the Jonone, α-iso-methyl ionone and methyl cedryl ketone, to the Alko get anethole, citronellol, eugenol, isoeugenol, geraniol, linalool, phenylethyl alcohol and terpineol, The hydrocarbons mainly include the terpenes and balms. Are also suitable Ambroxan, Heliotropin, Vanillin, Ethylvanillin, Cumann, Camphor, Menthol, Indol and Maltol as well as the Extracts of rice, rice husks, myrrh, olibanum, mistletoe and Salvia sclarea.
In das Verfahren können auch Enzyme eingesetzt werden, wie z. B. Cholin-Oxidase (aus Bakterien), Peroxidase (aus Sojabohnen), Laccasen und Tyrosinasen (aus Pilzen); Geeignete Enzyminhibitoren sind z. B. Phenylboronsäure und deren Derivate, Pentapeptide vom Typ Gly-Pro-Phe-Pro-Leu und Pep tide, die diese Sequenz enthalten, Bacitracin, Aminoethylbenzolsulfonylfluorid, die alle als Serin- Protease-Inhibitoren zur Regelung der Hautschuppung wirksam sind. Als Tyrosinase-Inhibitoren (Skin- Whitener) können Koji-Säure, Arbutin, Epicatechingallat, Bacelain, Dihydromyrecitin, Ascorbinsäure sowie 1000-1500 D-Proteine aus Seidenproteinhydroylsaten eingesetzt werden. Als Elastase-Inhibi toren zur Hautverjüngung können beispielsweise Cholesterol- und Phytosterolsulfat eingesetzt werden.Enzymes can also be used in the process, such as e.g. B. choline oxidase (from bacteria), Peroxidase (from soybeans), laccases and tyrosinases (from mushrooms); Suitable enzyme inhibitors are z. B. phenylboronic acid and its derivatives, pentapeptides of the type Gly-Pro-Phe-Pro-Leu and Pep tides containing this sequence, bacitracin, aminoethylbenzenesulfonyl fluoride, all as serine Protease inhibitors are effective for regulating skin flaking. As tyrosinase inhibitors (skin Whiteners) can include koji acid, arbutin, epicatechin gallate, bacelain, dihydromyrecitin, ascorbic acid and 1000-1500 D proteins from silk protein hydroylsates are used. As an elastase inhibi Gates for skin rejuvenation can be used, for example, cholesterol and phytosterol sulfate.
Des weiteren können alle weiteren bei Raumtemperatur festen kosmetischen Inhaltsstoffe, wie z. B.Furthermore, all other cosmetic ingredients solid at room temperature, such as. B.
- - Chitin- und Chitin-Derivate, wie z. B. Chitosan,- Chitin and chitin derivatives, such as. B. Chitosan,
- - Phospholipide (Lecithine),- phospholipids (lecithins),
- - Salicylsäureamid- Salicylic acid amide
- - Coffein- caffeine
- - Allantoin- Allantoin
- - Boswelliasäure,- boswellic acid,
- - Ferulasäure,- ferulic acid,
- - Glycyrrhizin,- glycyrrhizin,
- - Oryzanol- Oryzanol
- - Inulin- inulin
nach dem erfindungsgemäßen Verfahren in Nanopartikel überführt werden. Vorzugsweise werden sol che Dispersionen eingesetzt, welche die Nanopartikel in Mengen von 0,1 bis 10, vorzugsweise 1 bis 8 und insbesondere 2 bis 5 Gew.-% enthalten.be converted into nanoparticles by the process according to the invention. Preferably sol che dispersions used, the nanoparticles in amounts of 0.1 to 10, preferably 1 to 8 and in particular contain 2 to 5% by weight.
Die Dispersionen können wäßrig sein, sie können als Lösemittel jedoch auch niedere aliphatische Al kohole, wie vorzugsweise Ethanol, Propanol, Isopropylalkohol, Ethylenglycol, Propylenglycol oder Gly cerin enthalten. Herstellungsbedingt können auch Elektrolytsalze, wie z. B. Alkali- und/oder Erdalkali halogenide, -carbonate, -hydrogencarbonate, -sulfate, -phosphate oder -silicate in Mengen von 0,1 bis 10, vorzugsweise 0,5 bis 8 und insbesondere 1 bis 5 Gew.-% - bezogen auf die Dispersionen - zuge gen sein. Typische Beispiele für unerwünschte Elektrolytsalze, die es im Sinne des erfindungsgemäßen Verfahrens abzutrennen gilt, sind Natriumcarbonat, Calciumsulfat, Magnesiumsulfat und insbesondere Natriumchlorid.The dispersions can be aqueous, but they can also be lower aliphatic Al as solvents alcohols, such as preferably ethanol, propanol, isopropyl alcohol, ethylene glycol, propylene glycol or Gly contain cerin. Due to the manufacturing process, electrolyte salts such as e.g. B. alkali and / or alkaline earth halides, carbonates, bicarbonates, sulfates, phosphates or silicates in amounts of 0.1 to 10, preferably 0.5 to 8 and in particular 1 to 5% by weight, based on the dispersions be. Typical examples of undesirable electrolyte salts that are used in the sense of the invention Process to be separated are sodium carbonate, calcium sulfate, magnesium sulfate and in particular Sodium chloride.
Unter dem Begriff Ultrafiltration versteht der Fachmann ein Trennverfahren für makromolekulare Stoffe, die ein Molekulargewicht im Bereich von 1000 bis 200 000, entsprechend einem mittleren Durchmesser von 0,1 bis 0,001 µm. Die Ultrafiltration gehört wie die Mikrofiltration und die Umkehr osmose zu den durch einen auf der Feedseite angelegten Druck betriebenen Membrantrennverfahren und arbeitet typischerweise bei einer Druckdifferenz von 1 bis 10 und vorzugsweise 4 bis 6 bar. Für die Ultrafiltration kommen vorwiegend asymmetrisch strukturierte oder in Kompositweise gefertigte, poröse Membranen verschiedener organischer oder anorganischer Materialien, wie Polymere (z. B. Polysulfo ne, Polyacrylnitril, Celluloseacetat) oder Keramik (z. B. Zirkoniumoxid, Aluminiumoxid/Titandioxid) in Betracht. Es ist natürlich darauf zu achten, daß der cut-off der Membranen unterhalb des minimalen Durchmessers der Nanopartikel liegt. Die Ultrafiltration kann bei einem pH-Wert im Bereich von 1 bis 14 betrieben werden, wobei für Polymermembranen ein Bereich von 2 bis 11 besonders vorteilhaft ist. Die Betriebstemperatur kann 20 bis 100°C betragen, wobei es für Polymermembranen wiederum vorteil hafter ist, eine Temperatur im Bereich von 20 bis 50°C einzuhalten. Die Anordnung der Membranen kann im Sinne des erfindungsgemäßen Verfahrens beispielsweise in Platten-, Wickel-, Rohr-, Kapillar- oder Hohlfasermodulen erfolgen. Die Rückhaltegrenze ("cut-off") kann dabei im Bereich von 300 bis 100 000, vorzugsweise 1000 bis 15 000 Dalton liegen. Die Ultrafiltration kann dabei für eine begrenzte Aufkonzentrierung im "cross-flow"- oder zur vollständigen Abtrennung des Lösungsmittels im "dead end"-Modus betrieben werden. Die Diafiltration stellt einen Sonderfall der Ultrafiltration dar, bei dem die zu filtrierende Lösung kontinuierlich oder taktweise mit Wasser versetzt und durch die anschließen de Wasserabtrennung entsalzt wird. In einer bevorzugten Ausführungsform werden die Dispersionen daher in einer ersten Ultrafiltration aufkonzentriert und anschließend in der Diafiltration entsalzt, wobei dies im gleichen oder in verschiedenen Trennmodulen durchgeführt werden kann. The term “ultrafiltration” is understood by the person skilled in the art to mean a separation process for macromolecular Substances that have a molecular weight in the range of 1000 to 200,000, corresponding to an average Diameter from 0.1 to 0.001 µm. Ultrafiltration is like microfiltration and reversal osmosis to the membrane separation process operated by a pressure applied to the feed side and typically works at a pressure difference of 1 to 10 and preferably 4 to 6 bar. For the Ultrafiltration mainly come in asymmetrically structured or composite, porous Membranes of various organic or inorganic materials, such as polymers (e.g. polysulfo ne, polyacrylonitrile, cellulose acetate) or ceramic (e.g. zirconium oxide, aluminum oxide / titanium dioxide) in Consideration. It is of course important to ensure that the cut-off of the membranes is below the minimum Diameter of the nanoparticles. Ultrafiltration can be carried out at a pH in the range of 1 to 14 are operated, a range from 2 to 11 being particularly advantageous for polymer membranes. The Operating temperature can be 20 to 100 ° C, which in turn is advantageous for polymer membranes It is more important to maintain a temperature in the range of 20 to 50 ° C. The arrangement of the membranes can in the sense of the method according to the invention, for example, in plate, winding, tube, capillary or hollow fiber modules. The cut-off can be in the range from 300 to 100,000, preferably 1000 to 15,000 Daltons. The ultrafiltration can be used for a limited Concentration in the "cross-flow" - or for complete separation of the solvent in the "dead end "mode. Diafiltration is a special case of ultrafiltration in which the solution to be filtered is continuously or intermittently mixed with water and connected through de water separation is desalted. In a preferred embodiment, the dispersions therefore concentrated in a first ultrafiltration and then desalted in the diafiltration, where this can be done in the same or in different separation modules.
Eine technische 5gew.-%ige Dispersion von Zinkoxid-Nanopartikeln in Isopropylalkohol wurde bei 25°C und einer Druckdifferenz von 5 bar einer Ultrafiltration unterworfen. Zur Gewährlei stung eines ausreichend hohen Permeatflusses wurde eine keramische UF-Membran mit einem cut-off von 15 kD (90 Gew.-% nomineller Rückhalt für Partikel mit einem Molekulargewicht von 15 kD) ein ge setzt. Das Lösungsmittel sowie enthaltene Elektrolytsalze permeierten ungehindert durch die Membran und wurden in den Herstellprozeß für die Nanopartikel zurückgeführt, während die Nanopartikel durch die Membran zurückgehalten wurden. Mittels des Einsatzes der Deadend-Ultrafiltration war es möglich, den Partikelgehalt im Konzentrat so zu erhöhen, daß der Filtrationsrückstand eine stichfeste Konsistenz aufwies.A technical 5% by weight dispersion of zinc oxide nanoparticles in isopropyl alcohol was subjected to ultrafiltration at 25 ° C. and a pressure difference of 5 bar. To guarantee A ceramic UF membrane with a cut-off was provided to ensure a sufficiently high permeate flow of 15 kD (90 wt .-% nominal retention for particles with a molecular weight of 15 kD) a ge puts. The solvent and contained electrolyte salts permeated freely through the membrane and have been returned to the manufacturing process for the nanoparticles while the nanoparticles the membrane was retained. By using deadend ultrafiltration it was possible to increase the particle content in the concentrate so that the filtration residue has a firm consistency exhibited.
Eine wäßrige Dispersion mit einem Gehalt von 0,6 g Chitosan-Nanopartikeln und 2,5 Gew.-% Natriumchlorid wurde analog Beispiel 1 einer Ultrafiltration unterworfen und aufkonzentriert. Hierzu wurde eine Polyamidmembran mit einem cut-off von 3,5 kD (90 Gew.-% nomineller Rückhalt für Partikel mit einem Molekulargewicht von 3,5 kD) eingesetzt. Anschließend wurde das Konzentrat kontinuierlich mit entsalztem Wasser versetzt, diafiltriert und dabei entsalzt, wobei eine äquivalente Menge Wasser über die Membran abgezogen wurde. Das gereinigte Konzentrat wies noch eine Salzmenge von 0,1 Gew.-% auf.An aqueous dispersion containing 0.6 g chitosan nanoparticles and 2.5% by weight Sodium chloride was subjected to ultrafiltration as in Example 1 and concentrated. For this a polyamide membrane with a cut-off of 3.5 kD (90% by weight nominal retention for particles with a molecular weight of 3.5 kD). The concentrate then became continuous deionized water, diafiltered and desalted, with an equivalent amount of water was drawn off over the membrane. The cleaned concentrate still had a salt amount of 0.1% by weight on.
Claims (10)
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Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2060313A3 (en) * | 2007-11-15 | 2009-06-03 | Evonik Degussa GmbH | Method for fractioning oxidic nanoparticles with cross-stream membrane filtration |
US11053152B2 (en) | 2015-12-18 | 2021-07-06 | Heraeus Quarzglas Gmbh & Co. Kg | Spray granulation of silicon dioxide in the preparation of quartz glass |
US11236002B2 (en) | 2015-12-18 | 2022-02-01 | Heraeus Quarzglas Gmbh & Co. Kg | Preparation of an opaque quartz glass body |
US11299417B2 (en) | 2015-12-18 | 2022-04-12 | Heraeus Quarzglas Gmbh & Co. Kg | Preparation of a quartz glass body in a melting crucible of refractory metal |
US11339076B2 (en) | 2015-12-18 | 2022-05-24 | Heraeus Quarzglas Gmbh & Co. Kg | Preparation of carbon-doped silicon dioxide granulate as an intermediate in the preparation of quartz glass |
US11492285B2 (en) | 2015-12-18 | 2022-11-08 | Heraeus Quarzglas Gmbh & Co. Kg | Preparation of quartz glass bodies from silicon dioxide granulate |
US11492282B2 (en) | 2015-12-18 | 2022-11-08 | Heraeus Quarzglas Gmbh & Co. Kg | Preparation of quartz glass bodies with dew point monitoring in the melting oven |
US11708290B2 (en) | 2015-12-18 | 2023-07-25 | Heraeus Quarzglas Gmbh & Co. Kg | Preparation of a quartz glass body in a multi-chamber oven |
US11952303B2 (en) | 2015-12-18 | 2024-04-09 | Heraeus Quarzglas Gmbh & Co. Kg | Increase in silicon content in the preparation of quartz glass |
-
1999
- 1999-10-20 DE DE19950496A patent/DE19950496A1/en not_active Withdrawn
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2060313A3 (en) * | 2007-11-15 | 2009-06-03 | Evonik Degussa GmbH | Method for fractioning oxidic nanoparticles with cross-stream membrane filtration |
US8764992B2 (en) | 2007-11-15 | 2014-07-01 | Evonik Degussa Gmbh | Method of fractionating oxidic nanoparticles by crossflow membrane filtration |
US11053152B2 (en) | 2015-12-18 | 2021-07-06 | Heraeus Quarzglas Gmbh & Co. Kg | Spray granulation of silicon dioxide in the preparation of quartz glass |
US11236002B2 (en) | 2015-12-18 | 2022-02-01 | Heraeus Quarzglas Gmbh & Co. Kg | Preparation of an opaque quartz glass body |
US11299417B2 (en) | 2015-12-18 | 2022-04-12 | Heraeus Quarzglas Gmbh & Co. Kg | Preparation of a quartz glass body in a melting crucible of refractory metal |
US11339076B2 (en) | 2015-12-18 | 2022-05-24 | Heraeus Quarzglas Gmbh & Co. Kg | Preparation of carbon-doped silicon dioxide granulate as an intermediate in the preparation of quartz glass |
US11492285B2 (en) | 2015-12-18 | 2022-11-08 | Heraeus Quarzglas Gmbh & Co. Kg | Preparation of quartz glass bodies from silicon dioxide granulate |
US11492282B2 (en) | 2015-12-18 | 2022-11-08 | Heraeus Quarzglas Gmbh & Co. Kg | Preparation of quartz glass bodies with dew point monitoring in the melting oven |
US11708290B2 (en) | 2015-12-18 | 2023-07-25 | Heraeus Quarzglas Gmbh & Co. Kg | Preparation of a quartz glass body in a multi-chamber oven |
US11952303B2 (en) | 2015-12-18 | 2024-04-09 | Heraeus Quarzglas Gmbh & Co. Kg | Increase in silicon content in the preparation of quartz glass |
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