NO149092B - Kosmetisk hud- og haarpleiemiddel - Google Patents

Kosmetisk hud- og haarpleiemiddel Download PDF

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NO149092B
NO149092B NO773721A NO773721A NO149092B NO 149092 B NO149092 B NO 149092B NO 773721 A NO773721 A NO 773721A NO 773721 A NO773721 A NO 773721A NO 149092 B NO149092 B NO 149092B
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dihydroxy
trifluoroacetophenone
skin
compounds
hair care
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NO773721A
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NO149092C (no
NO773721L (no
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Rolf Brickl
Hans Eberhardt
Karl-Richard Appel
Uwe Lechner
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Thomae Gmbh Dr K
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Publication of NO149092B publication Critical patent/NO149092B/no
Publication of NO149092C publication Critical patent/NO149092C/no

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Abstract

osmetisk hud- og hårpleiemiddel.

Description

Foreliggende oppfinnelse angår kosmetiske hår og hudpleiemidler som inneholder nye substituerte fluoracylresorcinoler med den generelle formel I
I den ovenstående generelle formel I er en av
gruppene R, og R^ et hydrogenatom, og den annen av disse grupper er en alkylgruppe med 3 til 10 karbonatomer, et halogenatom,
en cyklopentyl-, cykloheksyl-, cykloheptyl- eller metylcykloheksylgruppe, eller R3 er en metylgruppe og R5 er hydrogen.
De substituerte fluoracylresorcinoler med den generelle
formel I kan fremstilles som beskrevet i vår søknad 77.1279.
Det er overraskende funnet at forbindelsene med den
generelle formel I er i besittelse av verdifulle kosmetiske hud-bevarende og hudpleiende egenskaper, og de er dessuten verdifulle bestanddeler i hårvann eller hårtonika for undertrykkelse av flassdannelse.
Av særlig fordel er den gode hudforlikelighet av
preparater inneholdende forbindelsene med formel I, idet kremer som inneholder opptil 10% av forbindelsene tåles uten irritasjon ved kontinuerlig behandling i 24 timer.
På grunn av den høye lipofile karakter og samtidig nærvær
av polare grupper, trenger forbindelsene godt inn i huden, men,
som det er vist ved undersøkelse av utskillelsesproduktene,
resorberes de bare i liten utstrekning.
Ved undersøkelse av hudforlikelighet og sensibilisering,
som utføres på marsvin, viste det seg at de svakt sensibili-
serende egenskaper hos mange resorcinoler forsvinner ved inn-
føring av trifluoracetylgruppen. Da resorcinoler som f.eks. heksyIresorcinol i mange tilfeller fremkaller allergier hos mennesker, er dette en vesentlig fordel.
Den nøyaktige årsak til flassdannelse er hittil ukjent.
Man finner imidlertid ved flassdannelse en hyperkeratose, dvs.
celledeling i epidermis finner sted raskere enn normalt, og dessuten er horndannelsen forstyrret. Efter uttalelser fra noen forfattere, f.eks. R. A. Gosse, R. W. VanderWyck, J. Soc. Cosmet. Chem. 20, 603 (1969), spiller soppen Pityrosporum ovale en
rolle ved dannelse av flass.
Noen av forbindelsene med formel I oppviser en sterk virkning mot Pitysporum ovale, og disse forbindelser reduserer også i betydelig grad hastigheten av den raske celledeling på huden og motvirker derfor flassdannelse.
Det er kjent at noen fenoler, resorcinoler, særlig alkylsubstituerte resorcinoler, og aromatiske ketoner har antiseptiske resp. antimikrobiellé egenskaper og f.eks. anvendes for fremstilling av preparater for hud- og hår-behandling
(se Jenkins og Hartung, The Chemistry of Org. Med. Prod.,
New York and London 1949, 3. utg. side 102-103 og 105-106, og US-patent 3.933.472, og dessuten dansk uti.skrift 125.885).
Det er nu overraskende funnet at de nye forbindelser
med den generelle formel I har meget god virkning mot bakterier og sopper, særlig mot mikroorganismer som spiller en rolle ved hud-lidelser. Disse forbindelser er særlig egnet for innarbeidelse i hud- og hårpleiemidler med utmerket virkning mot acne, filipenser, bakterielle hudinfeksjoner, mykoser, psoriasis og hyperkeratotiske tilstander på huden. Disse forhold er tidligere ikke beskrevet, og fra litteraturen kunne man heller ikke indirekte slutte seg til at denne anordr.ong av substituentene på benzenringen er utslagsgivende for å oppnå disse utmerkede virkninger.
I det følgende skal det illustreres at virkningene avtar merkbart når det foretas mindre strukturelle forandringer med hensyn til substituentene og deres stilling i molekylet med formel I. For de følgende forsøk ble det til dels anvendt forbindelser med kjente substitusjonsmønstere, og derved oppnås en direkte illustrasjon av at forbindelsene med den generelle formel I er bedre enn alle kjente forbindelser. For å bestemme struktur-virknings-sammenhengene og for å påvise en overlegen virkning hos forbindelser med formel I sammenlignet med forbindelser som tidligere er beskrevet i de ovennevnte publika-sjoner, ble følgende forbindelser benyttet:
CC = 4-n-heksylresorcinol
(Chem. Org. Med. Prod., s. 102)
DD = 2,4-dihydroksy-5-n-heksyl-acetofenon
EE = 2,2-diklor-2',4<1->dihydroksy-5-n-heksyl-acetofenon
EEE = 2,2,2-triklor-2',4'-dihydroksy-5-n-heksyl-acetofenon
E = 2,2,2-trifluor-2',4'-dihydroksy-5-n-heksyl-acetofenon
(Eksempel I-VI i foreliggende beskrivelse)
FF = 2,4-dihydroksy-3-metyl-acetofenon
FFF = 2-metyl-resorcinol
(analog Chem. Org. Med. Prod., s. 102)
GG = 2,2,2-triklor-2<1>,4'-dihydroksy-3-metyl-acetofenon
T = 2,2,2-trifluor-2',4'-dihydroksy-3-metyl-acetofenon
(med formel I)
Forbindelsene ble undersøkt med hensyn til sine virkninger mot slike mikroorganismer som Staphylococcus aureus SG 511, Streptococcus Aronson, Corynebacterium acnes, Candida albicans og Trichophyton mentagrophytes. Verdiene ble bestemt delvis med rekkefortynningsprøven S.D.T., delvis med hullprøven A.D.T. som minimal hemmende konsentrasjon MIC i ug/ml.
Forbindelsene i tabellene svarer til formelen
A. Struktur-virkningssammenheng med resp. uten -COCF^-gruppe:
a.
Resultat:
De beste virkninger oppnås når benzenringen foruten COCF^-gruppen også inneholder to hydroksylgrupper i o- og p-stilling.
Den således oppnådde forbindelse A kan virkningsmessig forbedres ytterligere når de i hovedkravet angitte substituer.ter innføres i 3- og 5-stilling. Forbindelsene med formel I oppviser de beste virkninger mot en rekke gram-positive bakterier, men også meget gode virkninger mot en rekke sopper, og de er dermed overlegne i forhold til alle lignende, kjente forbindelser.
De fra US-patent 3.933.472 kjente forbindelser
A' = 2,2,3'-triklor-4'-hydroksy-5<1->nitroacetofenon
(se eksempel 4)
B<1> = 2,2-diklor-4<1->hydroksy-3<1>,5'-dinitroacetofenon
(se eksempel 5)
C = 2,2,3'-triklor-4'-metoksy-5'-nitroacetofenon
(se eksempel 8) og
D' = 2,2,2-trifluor-4'-hydroksy-3',5'-dinitroacetofener
(se spalte 2, linje 34 i US-patent 3.933.472)
og den fra dansk utlegningsskrift 125.885 kjente forbindelse E' = 2',4'-dimetoksyacetofenon
(eksempel 2)
ble, da de er kjemisk beslektet med de nye forbindelser med formel I, undersøkt med hensyn til sin hemmende virkning ved rekke-fortynningsprøven (S.D.T) på Staphylococcus aureus SG.511, Streptococcus Aronson og Corynebacterium acnes som bakterier og Trichophyton mentagrophytes som sopp og med hensyn til sine toksi-siteter ved de i stamansøkningen beskrevne metoder, og på grunnlag av de derved oppnådde resultater ble forholdet mellom LD5q og minimal hemmende konsentrasjon bestemt, idet dette forhold angir toksisk indeks og dermed sikkerheten ved anvendelse av disse stoffer som aktivt middel. Med forbindelsene A', B', C<1>, D' og E' ble samtidig de følgende forbindelser med formel I
E = 2,4-dihydroksy-5-n-heksyl-trifluoracetofenon (sm.p. 90°C)
F = 2,4-dihydroksy-3-isobutyl-trifluoracetofenon (sm.p. 114°C)
G = 2,4-dihydroksy-3-isopenty1-trifluoracetofenon (sm.p. 101°C)
J = 2,4-dihydroksy-5-n-nonyl-trifluoracetofenon (sm.p. 87°C)
N = 2,4-dihydroksy-3-cyklopentyl-trifluoracetofenon (sm.p. 166°C)
0 = 2,4-dihydroksy-3-cykloheptyl-trifluoracetofenon (sm.p. 174°C)
P = 2,4-dihydroksy-3-isopropyl-trifluoracetofenon (sm.p. 145°C)
U = 2,4-dihydroksy-5-klor-trifluoracetofenon (sm.p. 110°C)
W = 2 , 4-dihydro]-".sy-5-n-decyl-trif luoracetof enon (sm.p. 89°C)
X = 2,4-dihydroksy-3-n-pentyl-trifluoracetofenon (sm.p. 105°C) Y = 2,4-dihydroksy-3-n-propyl-trifluoracetofenon (sm.p. 114°C) AA= 2,4-dihydro-5-isopropyl-trifluoracetofenon (sm.p. 97°C) og
BB= 2,4-dihydroksy-3-(4'-metyl-cykloheksyl)-trifluoracetofenon
(sm.p. 143°C)
undersøkt, særlig med hensyn til den toksiske indeks.
Den følgende tabell inneholder de derved fundne verdier:
Resultat:
Forbindelsene E til BB viser både mot gram-positive og også mot den hyppig forekommende sopp Trichophyton ment. en vesentlig forbedret virkning, men de utmerker seg også samtidiq ved en vesentlig forbedret toksisk indeks, målt i forhold til de nærmest beslektede forbindelser A<1> til D' fra det ovennevnte US-patent. Det er bemerkelsesverdig at den kjemisk nærmest beslektede forbindelse D' også i de høyeste undersøkte konsentrasjoner (320 ug/ml) var virkningsløs mot alle mikroorganismer (Staph. aureus, Strept. Aronson, Strept. pyogenes, Escherichia Coli, Pseudomonas aeruginosa, Candida albicans, Trichophyton mentagrophytes og Aspergillus niger). Forbindelsen E' er med hensyn til sin virkning mot Corynebacterium acnes
og Trichophyton mentagrophytes klart underlegen i forhold til forbindelsene E til BB.
Forbindelsene med den generelle formel I kan inn-arbeides i vanlige kosmetiske tilberedelsesformer. Som sådanne kan f.eks. nevnes skumaerosoler, pudder-spraypreparater, puddere, sjampoer, kremer, salver, tinkturer,
pastaer eller geler. Doseringen av de aktive stoffer ligger mellom 0,05 og 1%, fortrinnsvis 0,1 til 0,8 vekt%
Eksempel I
Skumaerosol (Fylling/boks 60 g), inneholdende 0,5 vekt% 2, 4- dihydroksy- 5- n- heksyl- trifluoracetofenon
(hurtig nedbrutt skum)
a) Oppløsning av aktivt stoff
I etanol oppløses i rekkefølge aktivt stoff,
"Cremophor" EL og den franske brennevinessens ved romtemperatur. I vann oppløses "Tween" 80 og "Texapon" N 25 likeledes ved romtemperatur, blandes med den etanoliske opp-løsning og filtreres.
b) AerosolfremstiIling
50,1 g av oppløsningen av aktivt stoff fylles på
en aluminiumboks som er dobbelt lakkert innvendig og er av passende størrelse. Boksen som er lukket med en ventil, fylles derefter med 9,9 g drivgassblanding på et aerosol-trykkfyllingsanlegg.
Eksempel II
Pudder-spray (fylling/boks 100 g), inneholdende 0,5 vekt% 2, 4- dihydroksy- 5- n- heksyl- trifluoracetofenon
a) Pudder av aktivt stoff
Det aktive stoff males sammen med "Aerosil" og ANM-mais
over en stiftmølle og utgnis med isopropylmyristat.
b) Aerosolfremstilling
3,5 g av pudderet av aktivt stoff fylles på en
aluminiumboks av egnet størrelse. Boksen som er lukket med en pudderventil, fylles derefter med 96,5 g drivgassblanding på et trykkfyllingsanlegg.
Eksempel III
Pudder inneholdende 0,5 vekt% 2,4-dihydroksy-5-n-heksyl-trifluoracetofenon
Det aktive stoff mikroniseres sammen med "Aerosil" 200, blandes med magnesiumstearat, laktose og ANM-mais og males derefter i en stiftmølle.
Eksempel IV
Sjampo inneholdende 0,1 vekt% 2,4-dihydroksy-5-n-heksyl-trif luoracetof enon
I en del av vannet oppløses "Nipagin"/"Nipasol" under oppvarmning, og derefter innrøres godt efter hverandre ved romtemperatur "Comperlan", "Zetesol" 856 T, "Lamepon" S-TR, "Euperlan", "Cetiol" HE og farvestoff. Efter tilsetning av aktivt stoff og god homogenisering innblandes parfymen.
Eksempel V
Gel inneholdende 0,5 vekt% 2,4-dihydroksy-5-n-heksyl-trifluoracetofenon
I en del av vannet oppløses "Nipagin" og "Nipasol" under oppvarmning, og ved 50°C under sterk omrøring tilsettes "Carbopol". Mikronisert aktivt stoff suspenderes i resten av vannet som er tilsatt "Tween", og settes til "Carbopol"-suspensjonen. Derefter innrøres silikonoljen, og under videre omrøring med trietanolamin innstilles viskositeten.
Eksempel VI
Krem med 0, 8 vekt% 2, 4- dihydroksy- 5- n- heksyl- trifluoracetofenon
Isopropylmyristat, silikonolje, "Tween", "Span" og "Lanette" smeltes ved 75°C og holdes ved denne temperatur. Propylenglykol, Nip/Nip (8:2) og vann kokes raskt opp og avkjøles til 75°C. I isopropylmyristatsmelten innrøres det aktive stoff, denne blanding innrøres i propylenglykolblandingen, og den ferdige blanding får avkjøles.
Eksempel VII
Gel inneholdende 0,5 vekt% 2,4-dihydroksy-3-isopropyl-trif luoracetof enon
I en del av vannet oppløses "Nipagin" og "Nipasol" under oppvarmning, og ved 50°C under sterk omrøring tilsettes "Carbopol". Mikronisert aktivt stoff suspenderes i resten av vannet som er tilsatt "Tween", og settes til "Carbopol"-suspensjonen. Derefter innrøres silikonoljen, og under videre omrøring med trietanolamin innstilles viskositeten.
Eksempel VIII
Krem med 1, 0 vekt% 2, 4- dihydroksy- 5- n- nonyl- trifluoracetofenon
Isopropylmyristat, silikonolje, "Tween", "Span" og "Lanette" smeltes ved 75°C og holdes ved denne temperatur.
Propylenglykol, Nip/Nip (8:2) og vann kokes raskt opp og avkjøles til 7 5°C. I isopropylmyristatsmelten innrøres det aktive stoff, denne blanding innrøres i propylenglykolblandingen, og den ferdige blanding får avkjøles.

Claims (4)

1. Kosmetisk hud- og hårpleiemiddel som inneholder en bestanddel som hemmer bakterier, karakterisert ved at denne bestanddel består av én eller flere forbindelser med den generelle formel I hvor en av gruppene R., og R^ er et hydrogenatom, og den annen av disse grupper er en alkylgruppe med 3 til 10 karbonatomer, et halogenatom, en cyklopentyl-, cykloheksyl-, cykloheptyl-eller metylcykloheksylgruppe, eller R^ er en metylgruppe og R,, er hydrogen.
2. Hud- og hårpleiemiddel som angitt i krav 1, karakterisert ved at det som aktiv bestanddel inneholder 2,4-dihydroksy-5-n-heksyl-trifluoracetofenon.
3. Hud- og hårpleiemiddel som angitt i krav 1, karakterisert ved at det som aktiv béstanddel inneholder 2,4-dihydroksy-5-n-nonyl-trifluoracetofenon.
4. Hud-, og hårpleiemiddel som angitt i krav 1, karakterisert ved at det som aktiv bestanddel inneholder 2,4-dihydroksy-3-isopropyl-trifluoracetofenon.
NO773721A 1976-04-14 1977-10-31 Kosmetisk hud- og haarpleiemiddel NO149092C (no)

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US4503256A (en) * 1981-07-02 1985-03-05 Noristan Limited Phlorophenone derivatives, processes for preparing such compounds, uses and pharmaceutical compositions of phlorophenone compounds
US4562292A (en) * 1983-08-18 1985-12-31 The Regents Of The University Of California Trifluoromethylketone sulfides and reversible enzyme inhibition therewith
IT1212907B (it) * 1983-12-21 1989-11-30 Romeo Aurelio Preparazione di fenoli alogenati
US5225607A (en) * 1985-08-09 1993-07-06 Imperial Chemical Industries Plc Insecticidal ethers
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AT351510B (de) 1979-07-25
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NO149092C (no) 1984-02-15
NO773721L (no) 1977-10-17
AU507258B2 (en) 1980-02-07
FI771158A7 (no) 1977-10-15
DE2616479C2 (de) 1986-12-04
DE2616479A1 (de) 1977-11-03
NZ183860A (en) 1984-07-06
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NO147598C (no) 1983-05-11
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US4225619A (en) 1980-09-30
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CA1101438A (en) 1981-05-19
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NO771279L (no) 1977-10-17
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