DE1922410A1 - Process for the production of a fragrant technical o-benzyl-p-chlorophenol and its use as an additive to cosmetic preparations - Google Patents
Process for the production of a fragrant technical o-benzyl-p-chlorophenol and its use as an additive to cosmetic preparationsInfo
- Publication number
- DE1922410A1 DE1922410A1 DE19691922410 DE1922410A DE1922410A1 DE 1922410 A1 DE1922410 A1 DE 1922410A1 DE 19691922410 DE19691922410 DE 19691922410 DE 1922410 A DE1922410 A DE 1922410A DE 1922410 A1 DE1922410 A1 DE 1922410A1
- Authority
- DE
- Germany
- Prior art keywords
- chlorophenol
- benzyl
- technical
- production
- additive
- 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.)
- Granted
Links
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/34—Alcohols
- A61K8/347—Phenols
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/005—Antimicrobial preparations
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
- C07C37/74—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by distillation
Description
1922410 FARBENFABRIKEN BAYER AG1922410 FARBENFABRIKEN BAYER AG
L£VERKUSEN-B*yerwerk 29. Patent-Abteilung Py - S / IML £ VERKUSEN-B * yerwerk 29. Patent Department Py - S / IM
Verfahren zur Herstellung eines wohlriechei sn technischen o-Benzyl-p-chlorphenols und sei^a Anwendung als Zusai- zu kosmetischen Präpai_tenMethod of making a fragrant sn technical o-benzyl-p-chlorophenols and be ^ a Use as an accessory to cosmetic preparations
Die vorliegende Erfindung betrifft ein Verfahren zur Herstellung eines p-Chlorphenol freien und darüber hinaus angenehm riechenden technischen o-Benzyl-p-chlorpherioIs sowie dessen Verwendung als bakterizid wirkender Bestandteil in auf die Haut aufzutragende», heilenden und pflegenden sowie die Haut verschönernden Präparaten, vorwiegend auf dem Kosmetiksektor.The present invention relates to a method for Production of a p-chlorophenol free and beyond pleasant smelling technical o-benzyl-p-chloropherioIs and its use as a bactericidal component in "healing and nourishing" to be applied to the skin as well as skin beautifying preparations, mainly in the cosmetics sector.
Technisches o-Benzyl-p-chlorp^enol enthält gewöhnlich 0,3.bis 1,5 Gew.-% p-Chlorphenol, das dem o-Benzyl-p-chlorphejiol einen intensiven phenolartige.. Geruch verleiht und somit seine breite Verwendung besonders axs Zusatz zu kosmetischen Präparaten unmöglich macht.Technical o-benzyl-p-chlorophenol usually contains 0.3 to 1.5% by weight of p-chlorophenol, the o-benzyl-p-chlorophejiol gives an intense phenol-like smell and thus its wide use especially axs additive to cosmetic Makes preparations impossible.
.Durch bekannte Reinigungsoperatioiien wie fraktionierte Desbillation des o-Benzyl-p-chlorphenols konnte selbst bei einer Abnahme bis zu 40 Gew.-^ Vorlauf kein genügend gerucharmes Produkt erhalten werden. Ebenso erfolglos blieben ümkristallisatlon aus verschiedenen lösungsmitteln, AuswaschenBy known purification operations such as fractionated Desbillation of the o-benzyl-p-chlorophenol could even with a decrease of up to 40 wt .- ^ lead not sufficient odorless product can be obtained. Crystallization from various solvents and washing out remained equally unsuccessful
mit 10 $-iger Sodalösung, Destillieren mit Wasserdampf oder Ausblasen mit verschiedenen Lösungsmitteln.with 10 $ soda solution, distilling with steam or Blow out with various solvents.
Ea wurde nun gefunden, daß"ma,ι ein wohlriechendes völlig von p-Chlorphenol befreites Produkt dadurch erhält, dali man technisches p-chlorphenolhaltiges o-Benzyl-p-chlorphenol mit It has now been found that a fragrant product completely freed from p-chlorophenol is obtained by using technical o-benzyl-p-chlorophenol containing p-chlorophenol
Le A 12 182Le A 12 182
00 9846/191100 9846/1911
einem kleinen Anteil Acetophenon destilliert und dom Yurlaui abtrennt. Das eingesetzte o-Benzyl-p-chlorphenol kann hierbei bis zu 3-Gew.-% p-Chlorphenol enthalten. Die zu dessen Abtrennung erforderliche Acetophenon-Menge kann im Bereich von 1 bis 20 Gew.-^ bezogen auf eingesetztes o-Benzyl-p-chlorphenol schwanken. Normalerweise sind der Einsatz von 4 bis 5 Gew.-^ Acetophenon und die Abnahme einer Vorlaufmenge von 8 bis 12 Gew.-^ ausreichend, um bei der Destillation den gewünschten Effekt zu erzielen. Der abgetrennte Vorlauf kann für denselben Prozeß noch einmal verwendet werden. Die Destillation kann in einem Druckbereich von etwa 0,001 bis 100 Torr, vorzugsweise von etwa 0,5 bis 15 Torr durchgeführt werden.a small portion of acetophenone distilled and dom Yurlaui separates. The o-benzyl-p-chlorophenol used can contain up to 3% by weight of p-chlorophenol. The one to separate it required amount of acetophenone can be in the range from 1 to 20 wt .- ^ based on the o-benzyl-p-chlorophenol used vary. Usually the use is from 4 to 5 wt .- ^ Acetophenone and the decrease in a lead amount of 8 to 12 Wt .- ^ sufficient to produce the desired in the distillation To achieve effect. The separated head can be used again for the same process. The distillation can be carried out in a pressure range of from about 0.001 to 100 torr, preferably from about 0.5 to 15 torr.
Das auf diese Weise erhaltene Produkt ist, wie die gaschromatographische Analyse zeigt, völlig frei von p-Chlorphenol und Acetophenon. »Es beaitzt einen angenehmen bittermandelölartigen Geruch, der eine breite Verwendung dieser bakterizid wirkenden Substanz als Zusatz zu allen Zubereitungen, die zu Heil-, Pflege- oder Verschörierungs zwecken auf die Haut aufgetragen werden können, gestattet, wobei der Schwerpunkt der Anwendung auf dem kosmetischen Sektor liegt.The product obtained in this way is like that obtained by gas chromatography Analysis shows completely free of p-chlorophenol and acetophenone. “It has a pleasant bitter almond oil-like taste Smell, the wide use of this bactericidal substance as an additive to all preparations that can be applied to the skin for healing, care or embellishment purposes, with the focus of application in the cosmetic sector.
In eine Destillationsapparatur (500 ml Dreihalskolben) aus Glas ohne Fraktlonierungsaufsatz werden 480 g eines technischen o-Benzyl-p-chlorphenols mit einem Erstarrungspunkt von 42,2 G und der Zusammensetzung vonInto a distillation apparatus (500 ml three-necked flask) Glass without a Fraktlonierungsaufsatz is 480 g of a technical o-Benzyl-p-chlorophenols with a freezing point of 42.2 G and the composition of
90,6 Gew,-$ o-Benzyl-p-chlorphenol, 8,9 Gew.-$ o-Benzy!phenol und 0,5 Gew.-^ p-Chlorphenol90.6 wt .- $ o-benzyl-p-chlorophenol, 8.9 wt .- $ o-benzyl phenol and 0.5 wt .- ^ p-chlorophenol
und 20 g (4 Gew.-$ im Gemisch) Acetophenon eingefüllt. Nach Aufschmelzen werden beide Substanzen durch Schütteln gut vermischt und dann im Vakuum bei 4 Torr überdestilliert. In einem Temperaturbereich von 86 - 169° C destillieren 42 g Vorlauf über. Der Hauptlaui (452 g) siedet bei 169 - 175° Cand 20 g (4% by weight in the mixture) of acetophenone. To Melting the two substances are mixed well by shaking and then distilled over in vacuo at 4 Torr. 42 g distill in a temperature range of 86 - 169 ° C Forward over. The main water (452 g) boils at 169-175 ° C
Le A 12 182 -2- Le A 12 182 -2-
00S846/00S846 /
l·l
und besteht aus. einem angenehm nach Bittermandelöl riechendem Produkt mit einem Schmelzpunkt von 43,8 C und folgender Zusammensetzung: 92,0 Gew-~?S o-Benzyl-p-chlorphenol undand consists of. a pleasant smell of bitter almond oil Product with a melting point of 43.8 C and the following Composition: 92.0 wt- ~? S o-benzyl-p-chlorophenol and
8,0 Gew.-^ Q-Benzy!phenol.8.0 weight percent benzyl phenol.
p-Chlorphenol oder Acetophenon sind im so gewonnenen Produkt laut gasChromatograph!seher Analyse nicht enthalten. Die Gegenwart von o-Benzylphenol ist wegen eines dem o-Benzyl-pchlorphenol ähnlichen Wirkungsspektrums nicht störend.p-chlorophenol or acetophenone are in the product obtained in this way according to gasChromatograph! seher analysis not included. the Presence of o-benzylphenol is due to one of the o-benzyl-pchlorophenol similar spectrum of activity not disturbing.
Le A 12 182 -3-Le A 12 182 -3-
0098A6/19110098A6 / 1911
Claims (1)
Priority Applications (9)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19691922410 DE1922410C3 (en) | 1969-05-02 | Process for the production of fragrant, p-chlorophenol-free technical o-benzyl-p-chlorophenol | |
CH552170A CH546719A (en) | 1969-05-02 | 1970-04-14 | A PROCESS FOR THE PREPARATION OF A NON-SMELLING O-BENZYL-P-CHLOROPHENOL FREE OF PCHLOROPHENOL AND ITS USE AS AN ADDITIVE TO COSMETIC PREPARATIONS. |
JP45035505A JPS4835066B1 (en) | 1969-05-02 | 1970-04-27 | |
US32466A US3696006A (en) | 1969-05-02 | 1970-04-27 | O-benzyl-p-chlorophenol substantially completely free from p-chlorophenol as an impurity and its production by distillation with acetophenone |
CA081,182A CA958369A (en) | 1969-05-02 | 1970-04-27 | Process for the purification of o-benzyl-p-chlorophenol containing p-chlorophenol |
FR7015974A FR2047175A5 (en) | 1969-05-02 | 1970-04-30 | |
BE749819D BE749819A (en) | 1969-05-02 | 1970-04-30 | PROCESS FOR THE PREPARATION OF A TECHNICAL O-BENZYL-P-CHLOROPHENOL WITH A PLEASANT ODOR, P-CHLOROPHENOL-FREE, AND APPLICATION OF THIS COMPOUND AS A BACTERICIDE ADDITIVE FOR PREPARATIONS |
NL7006477A NL7006477A (en) | 1969-05-02 | 1970-05-01 | |
GB21272/70A GB1261466A (en) | 1969-05-02 | 1970-05-04 | Process for the production of o-benzyl-p-chlorophenol |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19691922410 DE1922410C3 (en) | 1969-05-02 | Process for the production of fragrant, p-chlorophenol-free technical o-benzyl-p-chlorophenol |
Publications (3)
Publication Number | Publication Date |
---|---|
DE1922410A1 true DE1922410A1 (en) | 1970-11-12 |
DE1922410B2 DE1922410B2 (en) | 1977-02-24 |
DE1922410C3 DE1922410C3 (en) | 1977-10-06 |
Family
ID=
Also Published As
Publication number | Publication date |
---|---|
US3696006A (en) | 1972-10-03 |
NL7006477A (en) | 1970-11-04 |
FR2047175A5 (en) | 1971-03-12 |
CH546719A (en) | 1974-03-15 |
CA958369A (en) | 1974-11-26 |
BE749819A (en) | 1970-10-30 |
DE1922410B2 (en) | 1977-02-24 |
JPS4835066B1 (en) | 1973-10-25 |
GB1261466A (en) | 1972-01-26 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
C3 | Grant after two publication steps (3rd publication) | ||
E77 | Valid patent as to the heymanns-index 1977 | ||
8339 | Ceased/non-payment of the annual fee |