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EP0101699A1 - Utilisation d'esters de l'acide 2-(1-oxo-alkyl)-5-phenyl-2,4-pentadiene comme substances photofiltres - Google Patents

Utilisation d'esters de l'acide 2-(1-oxo-alkyl)-5-phenyl-2,4-pentadiene comme substances photofiltres

Info

Publication number
EP0101699A1
EP0101699A1 EP83900710A EP83900710A EP0101699A1 EP 0101699 A1 EP0101699 A1 EP 0101699A1 EP 83900710 A EP83900710 A EP 83900710A EP 83900710 A EP83900710 A EP 83900710A EP 0101699 A1 EP0101699 A1 EP 0101699A1
Authority
EP
European Patent Office
Prior art keywords
phenyl
alkyl
oxo
radical
carbon atoms
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Withdrawn
Application number
EP83900710A
Other languages
German (de)
English (en)
Inventor
Ernst-Joachim Brunke
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Dragoco Gerberding and Co GmbH
Original Assignee
Dragoco Gerberding and Co GmbH
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Dragoco Gerberding and Co GmbH filed Critical Dragoco Gerberding and Co GmbH
Publication of EP0101699A1 publication Critical patent/EP0101699A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • 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
    • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
    • 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
    • A61K8/37—Esters of carboxylic acids

Definitions

  • Sunlight consists of radiation components of different wavelength ranges. In addition to visible light, there is also infrared (IR) and ultraviolet (UV) radiation.
  • IR infrared
  • UV ultraviolet
  • the high-energy UV radiation contained in sunlight causes tanning of the skin, but also "sunburn” (erythema) [overview - in: W. Bruhn, Deutsche maschiner-Zeitung, 117, 1159-1162, 1362-1366, 1872-1876 (1977)].
  • the UV part of the sunlight is divided into three areas:
  • UV-A UV-A
  • Methyl shows the relatively small decrease in absorbance with long-term radiation (1, 3 and 6 hours).
  • the other esters of general formula 1 also show a UV maximum at 330 nm due to the same chromophoric group, however due to the different molecular weights, each with a different specific absorbance.
  • the radiation stability corresponds to that of the ethyl ester.
  • the substances of general formula 1 are liquid and can be easily incorporated into a wide variety of cosmetic formulations and are stable to emulsions. Self-odor and self-discoloration are low.
  • the compound of the general formula 1 does not change or discolor significantly under the influence of prolonged exposure to sunlight, it protects the material to which it was incorporated, but also the layers underneath, for a long time.
  • the compounds of formula 1 can be used alone or in combination with other UV absorbers in sunscreen cosmetics of various preparation forms (oil, cream, milk, spray), using customary carrier materials, diluents, fillers and auxiliaries. Examples of such materials are:
  • Natural and synthetic glycerides Natural and synthetic glycerides, natural and synthetic waxes, paraffin, whale, fatty acids, fatty alcohols (stearyl, oleyl, palmityl, cetyl alcohol etc.), Eucerin (5% wool fatty alcohols and 95% aliphatic hydrocarbons), wool fat, sorbitan fatty acid esters , Polyethylene sorbitan fatty acid esters, fatty alcohol polyglycol ethers and esters, carboxyvinyl polymers, gelatin, tragacanth, pectins, agar agar, methyl, ethyl or carboxymethyl cellulose or polyacrylic acid (as carrier)
  • - lower alcohols such as ethanol, isopropanol and glycols, Polyalcohols (ethylene glycol, glycerin) or water (as a solvent), - ionogenic or non-ionic, cation- or anion-active, or ampholytic emulsifiers, preservatives, dyes and perfume compositions (as auxiliaries).
  • the compounds of formula 1 are also suitable as light stabilizers for natural fibers such as cotton or wool (delaying or preventing the fading of colors), or for films, foils, threads, fibers and other molded articles made of synthetic plastics and as a component of filters and protective layers for photographic purposes or packaging material.
  • the content of compounds of formula 1 in cosmetic or technical applications is not critical per se and largely depends on the intended use. In general, the concentration in the end product can be 0.1 to 10% (but also more).
  • the compounds of formula 1 are easy to prepare.
  • esters of general formula 1 can be prepared from cinnamaldehyde (5) and a 1-oxo-alkyl-carboxylic acid ester (6), strong organic bases such as piperidine or pyrrolidine being used with preference, even in the presence of weak organic acids were.
  • strong organic bases such as piperidine or pyrrolidine being used with preference, even in the presence of weak organic acids were.
  • the compounds 1 are each present as a mixture of isomers (approx. 2: 3).
  • the UV-A light protection filter substances 2 and 3 already on the market have absorption maxima at ⁇ - 340 or 355 nm and must therefore be used in combination with a UV-B filter substance.
  • the compounds of formula 1 can be incorporated in concentrations of 0.1 to 10 5%, preferably 0.5 to 5%, in different cosmetic preparations such as oils, creams, lotions or in preparations for technical applications.
  • the compounds of formula 1 which because of the same chromophoric group each have the same absorption behavior in the UV range, have different physical properties (for example viscosity).
  • the compounds 1 can therefore advantageously be used in various cosmetic or technical preparation forms.
  • a sun protection oil was obtained which can be applied directly or in the form of a spray to the skin.
  • Triglyceride of caprylic and capric acid (1: 1) 10.0 g cetyl and stearyl alcohol (1: 1) 2.0 g cetyl / stearyl- ⁇ -ethylhexanoate (approx. 1: 1) 4.0 g isopropyl palmitate 6, 0 g stearyl / cetyl polyglycol ether 7.0 g silicone oil CP 100 0.5 g 2-acetyl-5-phenyl-2,4-pentadienoic acid ester of the formula 1 [preferential with triethylene glycol butyl ether residue, or ethylene glycol or 1.4 butanediol residue (as diester)] 4.0 g of perfume oil 0.5 g 34 0 g
  • Example 8 The constituents are emulsified at 70 ° C. as in Example 4, Example 8
  • Alkyl polyglycol emulsifier 2.0 g

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Dermatology (AREA)
  • Emergency Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Cosmetics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Les composés répondent à la formule 1 dans laquelle, R1 représente un reste alkyle droit ou ramifié ou un reste cycloalkyle à 1 à 18 atomes de carbone, un reste (poly)-alkoxy-alkyle avec en tout de 2 à 16 atomes de carbone, ou un reste (poly)-alkoxy avec 2 à 12 atomes de carbone, estérifié avec un reste d'acide 2-(1-oxo-alkyle)- 5- phényl-2,4- pentadiène.$(15,)$-R2 représente un reste alkyle droit ou ramifié ayant de 1 à 18 atomes de carbone; la ligne ondulée représente des isomères géométriques. Ces composés sont utilisés comme substances protectrices de la lumière dans les domaines cosmétiques et techniques.
EP83900710A 1982-02-24 1983-02-24 Utilisation d'esters de l'acide 2-(1-oxo-alkyl)-5-phenyl-2,4-pentadiene comme substances photofiltres Withdrawn EP0101699A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3206586 1982-02-24
DE3206586A DE3206586C1 (de) 1982-02-24 1982-02-24 Verwendung von 2-Acetyl-5-phenyl-2,4-pentadiensaeureestern als Lichtschutzfiltersubstanzen

Publications (1)

Publication Number Publication Date
EP0101699A1 true EP0101699A1 (fr) 1984-03-07

Family

ID=6156564

Family Applications (1)

Application Number Title Priority Date Filing Date
EP83900710A Withdrawn EP0101699A1 (fr) 1982-02-24 1983-02-24 Utilisation d'esters de l'acide 2-(1-oxo-alkyl)-5-phenyl-2,4-pentadiene comme substances photofiltres

Country Status (5)

Country Link
EP (1) EP0101699A1 (fr)
JP (1) JPS59500374A (fr)
DE (1) DE3206586C1 (fr)
IT (1) IT1160197B (fr)
WO (1) WO1983002941A1 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3938468A1 (de) * 1989-11-18 1991-05-23 Basf Ag 1,1-dialkoxy-2-oxo-6-aryl-3,5-alkadiene
AR020923A1 (es) 1998-10-23 2002-06-05 Unilever Nv Una composicion de filtro solar

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3125597A (en) * 1964-03-17 chj oh
US2381886A (en) * 1945-08-14 Esters
US3002992A (en) * 1958-10-10 1961-10-03 Givaudan Corp Alkoxyalkyl esters of p-methoxycinnamic acid

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO8302941A1 *

Also Published As

Publication number Publication date
IT1160197B (it) 1987-03-04
DE3206586C1 (de) 1983-07-21
IT8319757A0 (it) 1983-02-24
JPS59500374A (ja) 1984-03-08
WO1983002941A1 (fr) 1983-09-01

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Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

AK Designated contracting states

Designated state(s): AT CH DE FR GB LI NL

17P Request for examination filed

Effective date: 19840223

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN

18D Application deemed to be withdrawn

Effective date: 19860711

RIN1 Information on inventor provided before grant (corrected)

Inventor name: BRUNKE, ERNST-JOACHIM