US2334348A - Sunburn preventive - Google Patents

Sunburn preventive Download PDF

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Publication number
US2334348A
US2334348A US39940141A US2334348A US 2334348 A US2334348 A US 2334348A US 39940141 A US39940141 A US 39940141A US 2334348 A US2334348 A US 2334348A
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Prior art keywords
skin
hair
human
vitalizing
amino
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Miglarese John
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National Marketing Machine Co
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National Marketing Machine Co
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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILET PREPARATIONS
    • A61Q17/00Barrier 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
    • A61Q17/04Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K8/00Cosmetics or similar toilet preparations
    • A61K8/18Cosmetics or similar toilet preparations characterised by the composition
    • A61K8/30Cosmetics or similar toilet preparations characterised by the composition containing organic compounds
    • A61K8/49Cosmetics or similar toilet preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K8/00Cosmetics or similar toilet preparations
    • A61K8/18Cosmetics or similar toilet preparations characterised by the composition
    • A61K8/30Cosmetics or similar toilet preparations characterised by the composition containing organic compounds
    • A61K8/49Cosmetics or similar toilet preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4906Cosmetics or similar toilet preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4913Cosmetics or similar toilet preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid
    • A61K8/492Cosmetics or similar toilet preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid having condensed rings, e.g. indol
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K8/00Cosmetics or similar toilet preparations
    • A61K8/18Cosmetics or similar toilet preparations characterised by the composition
    • A61K8/30Cosmetics or similar toilet preparations characterised by the composition containing organic compounds
    • A61K8/49Cosmetics or similar toilet preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4906Cosmetics or similar toilet preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4926Cosmetics or similar toilet preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K8/00Cosmetics or similar toilet preparations
    • A61K8/18Cosmetics or similar toilet preparations characterised by the composition
    • A61K8/30Cosmetics or similar toilet preparations characterised by the composition containing organic compounds
    • A61K8/49Cosmetics or similar toilet preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/494Cosmetics or similar toilet preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • A61K8/4946Imidazoles or their condensed derivatives, e.g. benzimidazoles
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K8/00Cosmetics or similar toilet preparations
    • A61K8/18Cosmetics or similar toilet preparations characterised by the composition
    • A61K8/30Cosmetics or similar toilet preparations characterised by the composition containing organic compounds
    • A61K8/49Cosmetics or similar toilet preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/494Cosmetics or similar toilet preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • A61K8/496Triazoles or their condensed derivatives, e.g. benzotriazoles
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K8/00Cosmetics or similar toilet preparations
    • A61K8/18Cosmetics or similar toilet preparations characterised by the composition
    • A61K8/30Cosmetics or similar toilet preparations characterised by the composition containing organic compounds
    • A61K8/49Cosmetics or similar toilet preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4973Cosmetics or similar toilet preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • A61K8/498Cosmetics or similar toilet preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin

Description

Patented Nov. 16,

I UNITED i STATE- seminar: ranvnmrrvr:

John liflglaresc, Cincinnati, Ohio, assignor to The National Marking Machine Company, Cincinnati, Ohio, a corporation oi Ohio No Drawing. Application tune at. rear,

Serial No. eraser There are on the market several sunburn preventives, generally called sun tan lotions, which contain an ingredient having the characteristic of absorbing the shorter wave lengths of the solar rays generally described as ultraviolet rays or rays having a wave length of from 3000 to 3600 Angstrom units and converting them to wave lengths greater than 4000 Angstrom units which will not burn or'injuriously affect the human skin and which will not decolorize human hair. Said ingredient, which may be termedthe vitalizing ingredient, is usually carried in a vehicle of greasy nature, such, for illustration, as petroleum jelly, and this is applied to the portions of the human skin and hair which it is desired to protect. With such sun tan lotions the vitalizing ingredient is readily and easily washed or rubbed ofi with the vehicle, and when the vehicle is thus removed all protection against sunburn goes with it. Fur- .thermore, with such sun tan lotions the lotion.

must be applied to the skin in a relatively thick layer which is clearly visible and, therefore, objectionably unsightly.

My object is to provide a sunburn preventive in which the vitalizing ingredient has an nity for human skin and hair and which, when carried in a suitable vehicle and applied to the skin and hair will adhere to the skin and hair after the vehicle has been removed, in a manner simi= lar to that of a basic dyestuff applied to silk or wool, and which cannot be washed or rubbed oh, and, therefore, will protect the user from the injurious effects of direct sunlight for a relatively long time.

A further object is to provide a sunburn preventive which is substantially colorless and which, when applied to human skin and hair, and after the vehicle has been removed, will be in such a thin layer and colorless to such a degree that it is not clearly visible or of such greasy nature as to detract from the appearance of the user.

My improved vitalizing element has flve important characteristics: I

1. It is highly fluorescent in ultraviolet light or light rays. of wave lengths from 3000 to 3600 Angstrom units. This indicates a high absorption I in this region;

2. It is light in color and, therefore, substanskin and hair opaque to ultraviolet light even after removal of the vehicle.

My vitalizing ingredients may be described chemically as heterocyclic, aromatic, light col- 5 cred, fluorescent. basic compounds, I

' It is recognized that there are two essential parts of a fluorescent molecule; first the lumino- 'phore," which in this case is the heterocyclic and aromatic rings; and second the fluorophore,

which in this case is a basic auxochromic group.

It is known that it is not necessary to have either a heterocyclic ring, or a basic auxochrome in order to have fluorescence, for it is possible to have an aromatic ring for the luminophore, and ceraromatic ring, for the auxochrome.

I have obtained satisfactory results with the following formulae for thevitalizing ingredient. The numbering oi positions is in accord with Chemical Abstracts, vol. 31 on.

.i-ethyl 3-dimethylamino carbazole amino group gives the molecule an amnity for human skin and hair.

4-methyl 7-diethylamino coumarine The coumarine nucleus is the luminophore and the diethylamino group is the auxochrome pro moting fluorescence and causing aiflnity for skin and hair.

o 3-methyl b' -dimethylamzno azimidobenzene 0&1: N

The methyl-azimidobenzene nucleus is the luminophore, the dimethylamino groupis the auxochrome promoting fluorescence and giving 00 an aflinityfor skin and hair.

tain other unsaturated groups, such as another In adz-(para amino phenyl) -amino benzimidazole Here there are actually three auxochromes, the 2.-phenyl,' the para amino and the 5-amino groups. The phenyl group promotes only weak fluorescence, but the para-amino and 5-amino groups give a much stronger fluorescence and give an afllnity for skin "and hair.

z-phenul 5-amino benzoxazqle' Z-(pam amino phenyl) (i-methyl benzthiazole (commonly called dehydrothic-para-toluidine) CH3\ S\ I The benzthiazole is the luminophore. Here there are two auxochromes, the 2-phenyl and the paraamino groups. The phenyl gives only a weak fluorescence, the para-amino gives a much stronger fluorescence and gives the compound an amnity for skin and hair.

S-dimethylamino acridine Here the luminophore is the pyridine and unsubstituted benzene ring. The other benzene ring and dimethylamino group are the auxochromes. The benzene ring gives only a faint fluorescence, the dimethylamino group gives a strong fluorescence and in addition gives the molecule an affinity for skin and hair.

It is to be noted that each of the above mentioned compounds includes an amino or a substituted amino group, and that appears to be a characteristic which isessential to render a fluorescent dyestufi useful in my present invention.

The first three desired properties, namely fluorescence under ultraviolet light of wave length 3000 to 3600 Angstrom units, substantial lack of 60 color, and solubility in suitable solvents, may be rapidly and easily checked. The fourth, nontoxicity to human skin, requires the usual biological methods of testing. The fifth, afilnity for the human skin and hair, may be examined by testing the ailinity the compound has for protein fibers, namely silk and wool. Merely immerse the piece of silk or wool in an aqueous or alcoholic solution of the compound and wash and rinse thoroughly in warm water. Then examine the piece of silk or wool under an ultraviolet light, such as the General Electric H4 Black Bulb, in the substantial absence of visible light. A strong fluorescence shows the compound has an affinity for these protein fibers and has an aiilnity for human skin and hair. The aiiinity for skin and hair is not as great as is the afllnity for silk and wool, probably the skin is living matter. In the for human skin and hair by the expression "substantive to human skin and hair." By that, I mean that the fluorescent compound, although colorless, reacts with or is absorbed in human skin and hair, without the after the mannerof a substantive dye.

My compounds are all definite chemical compounds with definite solubilities and other properties. These compounds are intrinsically fluorescent and therefore do not require the addition of extraneous substances, such as acids or bases, to promote fluorescence. For example the naphthol sulfonic acids will not fiuoresce in a medium of pH less than 9, and quinine sulfate will not fiuoresce in a medium of pH more than 5. Both of these extreme values would irritate tender skin.

My compounds may be applied, either in the form of a solution, such as a mixture of ethanol, water and glycerol; dissolved or dispersed into a paste with such vehicles as vanishing cream or Carbowax"; or merely diluted with some inert powder, such as talcum powder or zinc stearate, and dusted on the skin and hair.

In whatever manner the essential ingredients be carried, the method of application is the same. The composition is rubbed on the skin or hair and allowed to remain on for at least flve minutes. The fluorescent compound afilxes itself to the skin or hair in much the same manner that a colored dyestufl afllxes itself to textile fibers from a dye bath. The vehicle is then washed or rubbed off. The amount that remains on affixed to the skin or hair is sufficient to give protection against harmful ultraviolet rays for a period of twenty-four hours.

follows A. Into 100 mls. of a mixture of 70 parts ethanol, 25 parts water, and 5 parts glycerol by volume, dissolve 3 grams of any one of the said vitalizing ingredients;

B. Into 100 grams of vanishing cream, thoroughly grind or incorporate 3 grams of any one of the said vitalizing ingredients;

C. Into 100 grams oi. Carbowax, a water soluble synthetic wax obtainable from Carbide and Carbon Chemical Corporation, thoroughly grind or incorporate 3 grams of any one 01 the said vitalizing ingredients.

55 D. Into 100 grams of talcum powder, or zinc stearate, thoroughly incorporate 5 grams of any one of the said vitalizing ingredients.

In practice I have dissolved or dispersed, or ground into or incorporated into the various vehicles mentioned, a small quantity of the various vitalizing ingredients mentioned, and forming a paste. I have rubbed this on the skin and hair to be protected, and permitted it to remain in such condition for about five minutes; during that time I have found that a sufflcient quantity of the vitalizing ingredient has, by reason of its afllnity to the skin and hair, become aifixed thereto. I have then washed or rubbed substantially all of the vehicle from the skin and hair. The remaining vitalizing element on the skin and hair was in such a thin layer and being substantially colorless was not objectionably visible and did not detract from the appearance of the person to which it was applied. I have demonspecification and claims I 5 I have referred 'to this characteristic of -afllnity use of any mordant,

My preferred compositions of matter are as 2,334,343 strated that with persons more than usually sus- .vitalizing ingredient becomes affixed to human skin and hair somewhat in the manner of basic dyestuffs adherence to silk or wool, that it will remain on the skin and hair only for a period of about 24 hours, after which it is removable by bathing or rubbing, or in some manner it disappears. This is probably due to the fact that the living tissues to which it is applied function to remove it. A fresh application of my sunburn preventive was applied each day for several days of exposure, and finally the sun tan became sumciently intense to substantially protect the person from sunburn.

My improved method of applying sunburn preventive to the human skin and hair is as follows:

The vitalizing ingredient is dispersed'in a vehicle of a non-greasy character and readily removable, or in a powder such as ordinary face powder which will adhere to the skin and hair. This is applied to the skin and hair in the ordinary manner and permitted to remain for a short time. I have had satisfactory results by permitting it to remain for fivevminutes. During that time a suflicient amount of the vitalizing ingreclient for sunburn prevention separates from the vehicle and'adheres to the skin and hair, due to its afiinity for the skin and hair. Then the vehicle and other ingredients contained therein are washed orrubbed ofl, with the result that only a microscopic layer of the vitalizing ingredient remains, and since that is substantially colorless, it is not objectionably visible and does not detract from the appearance of the user.

I claim as my invention:

1. A sunburn preventive to be applied as a coating to human skin and hair for the purpose of rendering the outer surfaces thereof, after removal of the coating, opaque to ultraviolet light comprising a non-toxic carrier having dispersed therein a colorless, fluorescent, basic compound, substantive to human skin and hair, selected from the group consisting of Q-ethyl 3-dimethylamino CHa carbazole CHI z-(para amino phony!) S-amtno benzimiduzole z-phenyl S-amino benzomazole z-(pam amino phenyl) 6-methzil benzthiazole s-dimethylamino acridine 3. A sunburn preventive to be applied as a coating to human skin and hair for the purposeof rendering the outer surfaces thereof opaque to ultraviolet light, after removal of the coating, comprising a suitable carrier having dispersed therein the compound, 4-methy1 7-diethylamino coumarine, having the following structural formula:

some n:

US2334348A 1941-06-23 1941-06-23 Sunburn preventive Expired - Lifetime US2334348A (en)

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Cited By (31)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2433939A (en) * 1942-11-04 1948-01-06 Celanese Corp Fluorescent-dyed cellulose acetate fabric
US2600375A (en) * 1946-06-14 1952-06-17 Ciba Ltd Amino-coumarin-sulfonates
US2620282A (en) * 1952-12-02 Fibrous synthetic material of
US2649385A (en) * 1953-08-18 Optically bleached fibrous material
US2649375A (en) * 1950-10-26 1953-08-18 Eastman Kodak Co Light-sensitive photographic element
US2654713A (en) * 1951-11-22 1953-10-06 Sandoz Ag Pulverizable and readily soluble brightening agents
US2661305A (en) * 1949-11-01 1953-12-01 Holliday Co Ltd L B Method for improving the brightness of textile materials and product
DE911368C (en) * 1948-10-21 1954-05-13 Bayer Ag Whitening agents for organic materials
US2715632A (en) * 1953-01-23 1955-08-16 Du Pont Whitening agents for cellulosic fiber
US2876130A (en) * 1955-12-21 1959-03-03 Palco Chemical Company Process for brightening suede
US2950986A (en) * 1957-08-22 1960-08-30 Union Carbide Corp Ultraviolet light absorbing compositions
US2968856A (en) * 1957-03-08 1961-01-24 American Cyanamid Co Method for continuously straightening sheet material
US3107252A (en) * 1959-12-01 1963-10-15 Irwin I Lubowe Allantoin salt
US3183231A (en) * 1963-07-17 1965-05-11 American Cyanamid Co Cyanonaphthoxazole brighteners
US3206306A (en) * 1959-04-09 1965-09-14 Azoplate Corp Material for electrophotographic purposes
US3271412A (en) * 1961-08-19 1966-09-06 Bayer Ag Coumarine compounds having triazole substituents
US3279068A (en) * 1964-01-23 1966-10-18 Barnes Hind Pharm Inc Method of detecting carious tissue
US3288801A (en) * 1962-06-07 1966-11-29 Sandoz Ltd Fluorescent 1, 2, 3-triazole derivatives of 3-phenyl-coumparin
US3696193A (en) * 1966-04-21 1972-10-03 Ciba Geigy Ag Cosmetic preparation containing 2-phenyl-benzoxazoles
US4098882A (en) * 1974-09-26 1978-07-04 L'oreal Anti-solar composition
FR2395025A1 (en) * 1977-06-23 1979-01-19 Henkel Kgaa cosmetics intended to be protected against light, in particular light in the region to the ultraviolet spectrum
US4284621A (en) * 1978-04-18 1981-08-18 Bayer Aktiengesellschaft Agents for protection against light
US4322212A (en) * 1979-12-13 1982-03-30 Henkel Kommanditgesellschaft Auf Aktien Oxidation hair dyes comprising substituted benzotriazoles
US4522808A (en) * 1980-08-15 1985-06-11 Societe Anonyme Dite: L'oreal Anti-sunburn compositions containing 2-phenyl-indole derivatives
US5217709A (en) * 1988-10-28 1993-06-08 L'oreal Sunscreening compositions containing 5-benzylidene-3-oxacyclopentanone
US5252322A (en) * 1989-09-22 1993-10-12 The Gillette Company Skin tanning compositions containing imidazoles
WO2003086341A2 (en) * 2002-04-17 2003-10-23 Ciba Specialty Chemicals Holding Inc. Aminophenylbenzothiazole compounds
US20080194522A1 (en) * 2004-08-25 2008-08-14 Gong Chen Development of Fluorogenic Substrates For Monoamine Oxidases (Mao-A and Mao-B)
US20090246154A1 (en) * 2006-07-27 2009-10-01 Barbara Wagner Use of aminophenylbenzotriazole derivatives for protecting human and animal skin and hair from the harmful effects of uv radiation and cosmetic compositions thereof
US20130190497A1 (en) * 2006-07-27 2013-07-25 The Trustees Of Columbia University In The City Of New York Fluorescent substrates for monoamine transporters as optical false neurotransmitters
US9075014B2 (en) 2010-01-29 2015-07-07 The Trustees Of Columbia University In The City Of New York pH-responsive fluorescent false neurotransmitters and their use

Cited By (39)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2620282A (en) * 1952-12-02 Fibrous synthetic material of
US2649385A (en) * 1953-08-18 Optically bleached fibrous material
US2433939A (en) * 1942-11-04 1948-01-06 Celanese Corp Fluorescent-dyed cellulose acetate fabric
US2600375A (en) * 1946-06-14 1952-06-17 Ciba Ltd Amino-coumarin-sulfonates
DE963268C (en) * 1946-06-14 1957-05-02 Ciba Geigy A method of washing nitrogen-containing fully synthetic fibrous or substances filmfoermigen
DE911368C (en) * 1948-10-21 1954-05-13 Bayer Ag Whitening agents for organic materials
US2661305A (en) * 1949-11-01 1953-12-01 Holliday Co Ltd L B Method for improving the brightness of textile materials and product
US2649375A (en) * 1950-10-26 1953-08-18 Eastman Kodak Co Light-sensitive photographic element
US2654713A (en) * 1951-11-22 1953-10-06 Sandoz Ag Pulverizable and readily soluble brightening agents
US2715632A (en) * 1953-01-23 1955-08-16 Du Pont Whitening agents for cellulosic fiber
US2876130A (en) * 1955-12-21 1959-03-03 Palco Chemical Company Process for brightening suede
US2968856A (en) * 1957-03-08 1961-01-24 American Cyanamid Co Method for continuously straightening sheet material
US2950986A (en) * 1957-08-22 1960-08-30 Union Carbide Corp Ultraviolet light absorbing compositions
US3244516A (en) * 1959-04-09 1966-04-05 Azoplate Corp Electrophotographic mateiral and process
US3206306A (en) * 1959-04-09 1965-09-14 Azoplate Corp Material for electrophotographic purposes
US3107252A (en) * 1959-12-01 1963-10-15 Irwin I Lubowe Allantoin salt
US3271412A (en) * 1961-08-19 1966-09-06 Bayer Ag Coumarine compounds having triazole substituents
US3288801A (en) * 1962-06-07 1966-11-29 Sandoz Ltd Fluorescent 1, 2, 3-triazole derivatives of 3-phenyl-coumparin
US3183231A (en) * 1963-07-17 1965-05-11 American Cyanamid Co Cyanonaphthoxazole brighteners
US3279068A (en) * 1964-01-23 1966-10-18 Barnes Hind Pharm Inc Method of detecting carious tissue
US3696193A (en) * 1966-04-21 1972-10-03 Ciba Geigy Ag Cosmetic preparation containing 2-phenyl-benzoxazoles
US4098882A (en) * 1974-09-26 1978-07-04 L'oreal Anti-solar composition
FR2395025A1 (en) * 1977-06-23 1979-01-19 Henkel Kgaa cosmetics intended to be protected against light, in particular light in the region to the ultraviolet spectrum
US4284621A (en) * 1978-04-18 1981-08-18 Bayer Aktiengesellschaft Agents for protection against light
US4322212A (en) * 1979-12-13 1982-03-30 Henkel Kommanditgesellschaft Auf Aktien Oxidation hair dyes comprising substituted benzotriazoles
EP0030680B1 (en) * 1979-12-13 1983-08-24 Henkel Kommanditgesellschaft auf Aktien Hair dye compositions
US4522808A (en) * 1980-08-15 1985-06-11 Societe Anonyme Dite: L'oreal Anti-sunburn compositions containing 2-phenyl-indole derivatives
US5217709A (en) * 1988-10-28 1993-06-08 L'oreal Sunscreening compositions containing 5-benzylidene-3-oxacyclopentanone
US5252322A (en) * 1989-09-22 1993-10-12 The Gillette Company Skin tanning compositions containing imidazoles
WO2003086341A2 (en) * 2002-04-17 2003-10-23 Ciba Specialty Chemicals Holding Inc. Aminophenylbenzothiazole compounds
WO2003086341A3 (en) * 2002-04-17 2004-04-01 Ciba Sc Holding Ag Aminophenylbenzothiazole compounds
US20050175554A1 (en) * 2002-04-17 2005-08-11 Barbara Wagner Aminophenylbenzothiazole compounds
US20090060853A1 (en) * 2002-04-17 2009-03-05 Barbara Wagner Aminophenylbenzothiazole compounds
US20090068129A1 (en) * 2002-04-17 2009-03-12 Barbara Wagner Aminophenylbenzothiazole compounds
US20080194522A1 (en) * 2004-08-25 2008-08-14 Gong Chen Development of Fluorogenic Substrates For Monoamine Oxidases (Mao-A and Mao-B)
US20090246154A1 (en) * 2006-07-27 2009-10-01 Barbara Wagner Use of aminophenylbenzotriazole derivatives for protecting human and animal skin and hair from the harmful effects of uv radiation and cosmetic compositions thereof
US8221729B2 (en) * 2006-07-27 2012-07-17 Basf Se Use of aminophenylbenzotriazole derivatives for protecting human and animal skin and hair from the harmful effects of UV radiation and cosmetic compositions thereof
US20130190497A1 (en) * 2006-07-27 2013-07-25 The Trustees Of Columbia University In The City Of New York Fluorescent substrates for monoamine transporters as optical false neurotransmitters
US9075014B2 (en) 2010-01-29 2015-07-07 The Trustees Of Columbia University In The City Of New York pH-responsive fluorescent false neurotransmitters and their use

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