US3878229A - Sun-screening compounds III - Google Patents

Sun-screening compounds III Download PDF

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Publication number
US3878229A
US3878229A US465259A US46525974A US3878229A US 3878229 A US3878229 A US 3878229A US 465259 A US465259 A US 465259A US 46525974 A US46525974 A US 46525974A US 3878229 A US3878229 A US 3878229A
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US
United States
Prior art keywords
sun
compound
compound according
acid
skin
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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.)
Expired - Lifetime
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US465259A
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English (en)
Inventor
Albert Frederick Strobel
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ISP Investments LLC
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GAF Corp
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Filing date
Publication date
Priority to US465259A priority Critical patent/US3878229A/en
Application filed by GAF Corp filed Critical GAF Corp
Priority to CA217,454A priority patent/CA1064049A/en
Priority to GB82975A priority patent/GB1428648A/en
Priority to JP50013932A priority patent/JPS50140642A/ja
Priority to DE19752509647 priority patent/DE2509647A1/de
Priority to CH288275A priority patent/CH616842A5/de
Publication of US3878229A publication Critical patent/US3878229A/en
Application granted granted Critical
Priority to FR7513032A priority patent/FR2268789B1/fr
Assigned to CHASE MANHATTAN BANK, THE NATIONAL ASSOCIATION reassignment CHASE MANHATTAN BANK, THE NATIONAL ASSOCIATION SECURITY INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: DORSET INC. A CORP OF DELAWARE
Assigned to GAF CHEMICALS CORPORATION reassignment GAF CHEMICALS CORPORATION CHANGE OF NAME (SEE DOCUMENT FOR DETAILS). EFFECTIVE ON 04/11/1989 Assignors: DORSET INC.
Assigned to DORSET INC., A DE CORP. reassignment DORSET INC., A DE CORP. CHANGE OF NAME (SEE DOCUMENT FOR DETAILS). EFFECTIVE APRIL 10, 1989 Assignors: GAF CORPORATION, A DE CORP.
Assigned to CHASE MANHATTAN BANK (NATIONAL ASSOCIATION), THE reassignment CHASE MANHATTAN BANK (NATIONAL ASSOCIATION), THE SECURITY INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: GAF CHEMICALS CORPORATION, A CORP. OF DE
Assigned to ISP 3 CORP reassignment ISP 3 CORP ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: GAF CHEMICALS CORPORATION
Assigned to ISP INVESTMENTS INC. reassignment ISP INVESTMENTS INC. CHANGE OF NAME (SEE DOCUMENT FOR DETAILS). EFFECTIVE ON 06/06/1991 Assignors: ISP 3 CORP.
Anticipated expiration legal-status Critical
Assigned to GAF CHEMICALS CORPORATION, GAF BUILDING MATERIALS CORPORATION, SUTTON LABORATORIES, INC. reassignment GAF CHEMICALS CORPORATION RELEASED BY SECURED PARTY (SEE DOCUMENT FOR DETAILS). Assignors: CHASE MANHATTAN BANK, THE (NATIONAL ASSOCIATION)
Expired - Lifetime legal-status Critical Current

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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
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • A61K8/445—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof aromatic, i.e. the carboxylic acid directly linked to the aromatic ring

Definitions

  • Sun-screening compositions containing such compounds and a cosmetically acceptable diluent or carrier, and methods of using such compositions, are also disclosed.
  • the present invention relates to sun-screening compositions, methods of using the same and novel sunscreening compounds.
  • Ultraviolet radiation on the skin such as from the sun, of a wavelength of 290 3 l 3 mp. is known to produce erythema, particularly in fair skinned subjects.
  • ultraviolet radiation of from 315 320 my. to 350 400 mp. promotes a tanning ofthe skin.
  • a sun-screening composition must at least remove substantially all of the burning rays, and in many instances a good portion of the tanning rays.
  • R, and R are independently straight or branched chain lower alkyl; Y is C C alkylene; R is alkyl of 8 to 18 carbon atoms; X is a cosmetically acceptable monoor divalent anion; and n is l or 2 to provide an electrically neutral compound.
  • X is halide, sulfate, phosphate, p-(lower alkyl) benzene sulfonate, benzoates, R COO HOOCR -,COO' or OOCR -,COO*, where R is alkyl of l to 18 carbon atoms and R,-, is alkylene of l to 18 carbon atoms.
  • Such compounds show absorption of ultraviolet light in the range of 290 315 my. and have good substantivity on the skin.
  • the compounds of formula (I) are water soluble, but the degree of water solubility decreases as the number of carbon atoms in R and/or R and/or R,-, in-
  • lower alkyl denotes a univalent saturated branched or straight hydrocarbon chain containing from 1 to 6 carbon atoms. Representative of such lower alkyl groups are thus methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec.butyl, tert.butyl, pentyl, isopentyl, neopentyl, tert.pentyl, hexyl, and the like.
  • alkylene of 2 to 6 carbon atoms denotes a divalent saturated straight or branched hydrocarbon obtained by removing a hydrogen atom from the lower alkyl defined above, excluding methyl.
  • alkyl of l to 18 carbon atoms and alkyl of 8 to 18 carbon atoms denote a univalent saturatd -.branched or straight hydrocarbon chain containing from I to 18 carbon atoms or 8 to 18 carbon atoms,
  • alkyl groups are thus methyl, ethyl, propyl, isopropyl, butyl, isobutyl,
  • alkylene of l to 18 carbon atoms and alkylene of 8 to 18 carbon atoms denote a divalent saturated branched or straight hydrocarbon chain obtained by removing a hydrogen atom from the alkyl defined above.
  • halide denotes chloride, bromide, iodide and fluoride, preferably chloride or bromide.
  • R and R are C -C straight or branched chain alkyl.
  • the no carboxylic acid is one wherein R is lower alkylene, and most preferably alkylene of l to 4 carbon atoms.
  • Compounds which are active as sun-screening agents are known and include such widely diverse compounds as dibenzylacetone, quinine sulfate and ethyl umbelliferone.
  • Alkyl esters of p-dialkylaminobenzoic acid have also been proposed for use as sun-screening agents in US. Pat. Nos. 2,853,423; 3,403,207; and 3,479,428. In view of this highly empirical nature of the ability of a compound selectively to absorb ultraviolet radiation in the narrow range of 290 to 315 mu, it was not expected that the compounds of formula (I) would be useful as sun-screening agents.
  • the quaternary salts of formula (I) where X is halide can be prepared by reacting at room temperature, with or without a solvent. approximately stoichiometric quantities of a dialkylaminoalkyl pdialkylaminobenzoate (ll) and an alkyl halide (lll) to form the quaternary ammonium halide (lV according to process (A) below:
  • Compounds of formula (I) where X is other than halide can be formed treating the quaternary ammonium halide (IV) with silver oxide to produce the mono quaternary ammonium hydroxide.
  • the excess silver oxide and precipitated silver halide is removed by filtration and the aqueous solution of mono-quaternary ammonium hydroxide then is reacted with an appropriate acid to introduce the desired anion, such as sulfonic acid, phosphoric acid, p-(lower alkyl) benzenesulfonic acid, benzoic acid or a monoor dicarboxylic acid of the formula R COO l-l or R (COOH)
  • the quaternary ammonium halide (1V) can be reacted with the desired acid in approximately stoichiometric quantities, in accordance with processes (B) or (C).
  • dialkylaminoalkyl p-dialkylaminobenzoate (ll) used in process (A) is known, e.g. see US. Pat. No. 820,830, and can conveniently be made by alkylating an alkyl p-aminobenzoate with an alkyl halide in an organic solvent, and reacting the resulting alkyl pdialkylaminobenzoate with a dialkylaminoalkanol.
  • dialkylaminoalkyl pdialkylaminobenzoate may be:
  • the aliphatic dicarboxylic acid R (COOH)- used in reaction (C) may be malonic acid, succinic acid, adipic acid, 2,2-dimethylglutaric acid, suberic acid, sebacic acid, dodecanedioic acid, tetradecanedioic acid, hexadecanedioic acid, and nonadecanedioic acid.
  • the sun-screening agents of formula (I) are applied to the skin in the form of a sun-screen composition
  • a sun-screen composition comprising the compound offormula (l) and a cosmetically acceptable diluent or carrier.
  • the term .cosmetically acceptable diluent or carrier denotes a nontoxic, non-irritating substance which when mixed with the compound of formula (I) makes the compound more suitable to be appliedto the skin.
  • the compositions can thus be solutions, oils, lotions, ointments, liquid or solid creams, aerosols and the like.
  • the sun-screening composition of the invention is formed by admixing dissolving or dispersing the sunscreening compound of formula (1) into the desired cosmetically acceptable diluent or carrier.
  • Solutions are formed by dissolving the sun-screening compound in water or other solvent.
  • Oils are prepared by using vegetable andlor mineral oils, such as sesame oil and/or white mineral oil as the cosmetically acceptable diluent or carrier.
  • Creams may be prepared by adding lanolin and a suitable absorbent base to the vegetable and/or mineral oils. Oil-in-water emulsions may be employed as the vehicle to form lotions, but are not preferred since such compositions tend to wash off more easily than others. by
  • An alcoholic lotion containing an alcohol, such as ethanol or isopropanol, and a film-forming substance as the cosmetically acceptable diluent or carrier is preferred, since this tends to provide more permanent protection even after exposure of the skin to water.
  • Preferred film-forming agents for alcoholic lotions are cator oil, lauryl and oleyl alcohols, glycol and glyceryl oleates, mannitol and sorbitol oleate, laurate or ricinoleate, butyl stearate, ethyl oleate, laurate, or ricinoleate and methyl oleate, laurate or ricinoleate.
  • Perfumes, anti-oxidants, colorants. insect-repellants and the like may be included in the sun-screening composition, if desired.
  • the sun-screening composition of the invention contains an effective amount of the sun-screening compound of formula (I) to prevent erythema.
  • an amount of 0.01 to preferably 0.05 to 3%, by weight, of the total composition, of the sun-screening compound of formula (I) may be used.
  • the composition is applied topically every few hours, as needed, in the same manner as conventional sun-screening compositions.
  • the compounds of the invention may also be used to protect blond and light-colored hair from the deleterious effects of ultraviolet radiation.
  • the compounds of formula (I) are admixed with the cosmetically acceptable diluent or carrier to provide a composition containing from 0.05 to 10%, by weight,-', ,5 preferably 2 to 5%, by weight, of the compound of formula (l).
  • the hair-protection compositions are applied to the hair in the same manner as a conventional hair lotion, hair cream or hair tonic, before exposure to ultraviolet radiation, and thereafter as desired.
  • Cosmetically acceptable diluents or carriers used in such conventional hair preparations may be used in the hairprotection composition of the invention.
  • a 2%, by weight, solution of the candidate compound in 50% ethanol-50% water is then rubbed into the skin, dried in air, and part of the air-dried surface is rinsed with water for 2 minutes. Examination of the rinsed and unrised sections of skin was then made in UV (black) light. The retention of the UV absorber on the skin is determined by observing the color of the treated and untreated sections under UV light and comparing the color tothe reference solutions.
  • Tests for sunburn protection are carried out by applying a 2%, by weight, solution of the candidate compound in 50% ethanol-50% water to a small patch of skin, followed by exposure to sun for 2 hours.
  • a compound must prevent erythema after exposure for 2 hours to the sun at a latitude of New York City.
  • TEST PROCEDURE FOR HAlR The substantivity of the candidate compound to hair is tested in the following manner.
  • the candidate compound is dissolved in mls. of water to provide a 0.1%, by weight, aqueous solution.
  • 10 gms. of hair is immersed in the resulting aqueous solution, stirred for one-half hour, removed, rinsed and dried.
  • the UV- absorption of the aqueous solution into which the hair was immersed is measured both before and after the immersion of the hair in the solution, using the same technique described above.
  • the of the compound left after rinsing determines the amount of substantivit
  • the following Examples illustrate the invention. In the Examples, all percentages and parts are by weight unless stated otherwise.
  • compound (B) When the pH of the aqueous solution is adjusted to 8.5, compound (B) has higher substantivity on the skin and gives good protection against sunburn.
  • the precipitated product is filtered from the mixture and dried.
  • R, and R are independently straight or branched chain lower alkyl; Y is C C alkylene; R is alkyl of 8 to 18 carbon atoms; X is an anion selected CH COO the mixture 3.
  • R is straight or branched chain alkyl of ll to 18 carbon atoms.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Dermatology (AREA)
  • Cosmetics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US465259A 1974-04-29 1974-04-29 Sun-screening compounds III Expired - Lifetime US3878229A (en)

Priority Applications (7)

Application Number Priority Date Filing Date Title
US465259A US3878229A (en) 1974-04-29 1974-04-29 Sun-screening compounds III
CA217,454A CA1064049A (en) 1974-04-29 1975-01-07 Salts of alkanolamine esters of para dialkylaminobenzoic acid and their use as sun-screening agents
GB82975A GB1428648A (en) 1974-04-29 1975-01-08 Quaternary compounds of dialkyl benzoic derivatives sun- screening compositions containing the compounds and their appli cation as sun-screening agents
JP50013932A JPS50140642A (enrdf_load_stackoverflow) 1974-04-29 1975-01-31
DE19752509647 DE2509647A1 (de) 1974-04-29 1975-03-05 Neue derivate der dialkylaminoalkyl- p-dialkyl-aminobenzoesaeureester
CH288275A CH616842A5 (enrdf_load_stackoverflow) 1974-04-29 1975-03-06
FR7513032A FR2268789B1 (enrdf_load_stackoverflow) 1974-04-29 1975-04-25

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US465259A US3878229A (en) 1974-04-29 1974-04-29 Sun-screening compounds III

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US3878229A true US3878229A (en) 1975-04-15

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US465259A Expired - Lifetime US3878229A (en) 1974-04-29 1974-04-29 Sun-screening compounds III

Country Status (7)

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US (1) US3878229A (enrdf_load_stackoverflow)
JP (1) JPS50140642A (enrdf_load_stackoverflow)
CA (1) CA1064049A (enrdf_load_stackoverflow)
CH (1) CH616842A5 (enrdf_load_stackoverflow)
DE (1) DE2509647A1 (enrdf_load_stackoverflow)
FR (1) FR2268789B1 (enrdf_load_stackoverflow)
GB (1) GB1428648A (enrdf_load_stackoverflow)

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU569940B2 (en) * 1984-06-21 1988-02-25 Van Dyk & Company Benzene sulfonate quaternary ammonium salts of sunscreen carboxylic acids
US5427773A (en) * 1993-08-25 1995-06-27 Isp Van Dyk Inc. Quaternary salts of dialkylaminobenzamides
US5474691A (en) * 1994-07-26 1995-12-12 The Procter & Gamble Company Dryer-added fabric treatment article of manufacture containing antioxidant and sunscreen compounds for sun fade protection of fabrics
US5543083A (en) * 1994-07-26 1996-08-06 The Procter & Gamble Company Fatty amine derivatives of butylated hydroxy toluene for the protection of surfaces from physical and chemical degradation
US5705474A (en) * 1994-07-26 1998-01-06 The Procter & Gamble Company Rinse added fabric softener compositions containing sunscreens for sun-fade protection for fabrics
US5723435A (en) * 1994-07-26 1998-03-03 The Procter & Gamble Company Rinse added fabric softener compositions containing antioxidants for sun-fade protection fabrics
US6607735B2 (en) 2000-12-21 2003-08-19 Johnson & Johnson Consumer Companies, Inc. Method for reducing the appearance of dark circles under the eyes
US20040191206A1 (en) * 2000-10-02 2004-09-30 Curtis Cole Methods for reduction of inflammation and erythema
US20040213754A1 (en) * 2000-10-02 2004-10-28 Cole Curtis A. Method for cleansing sensitive skin using an alkanolamine
US20050238730A1 (en) * 2001-11-21 2005-10-27 Agnes Le Fur Compositions comprising an ethanolamine derivative and organic metal salts
US20080063844A1 (en) * 2001-06-29 2008-03-13 Mannington Mills, Inc. Surface coverings containing aluminum oxide
US7396526B1 (en) 1998-11-12 2008-07-08 Johnson & Johnson Consumer Companies, Inc. Skin care composition
CN109232285A (zh) * 2018-10-16 2019-01-18 新乡学院 一种具有抗菌活性的苯佐卡因双取代衍生物的合成方法和应用

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS59140694A (ja) * 1983-01-31 1984-08-13 Sharp Corp ダイナミツクｒａｍのリフレツシユ方法

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3536723A (en) * 1966-09-27 1970-10-27 Menarini Soc In Accomandita Se P - (2 - alkyloxy - benzoyl) - aminobenzoates of n - dialkylamine - alkyl and their quaternary salts

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3536723A (en) * 1966-09-27 1970-10-27 Menarini Soc In Accomandita Se P - (2 - alkyloxy - benzoyl) - aminobenzoates of n - dialkylamine - alkyl and their quaternary salts

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU569940B2 (en) * 1984-06-21 1988-02-25 Van Dyk & Company Benzene sulfonate quaternary ammonium salts of sunscreen carboxylic acids
US5427773A (en) * 1993-08-25 1995-06-27 Isp Van Dyk Inc. Quaternary salts of dialkylaminobenzamides
US5427774A (en) * 1993-08-25 1995-06-27 Isp Van Dyk Inc. Heterocyclic quaternary salts of para-dialkylamino benzamide derivatives
US5869443A (en) * 1994-07-26 1999-02-09 The Procter & Gamble Company Dryer-added fabric treatment article of manufacture containing antioxidant and sunscreen compounds for sun fade protection of fabrics
US5705474A (en) * 1994-07-26 1998-01-06 The Procter & Gamble Company Rinse added fabric softener compositions containing sunscreens for sun-fade protection for fabrics
US5723435A (en) * 1994-07-26 1998-03-03 The Procter & Gamble Company Rinse added fabric softener compositions containing antioxidants for sun-fade protection fabrics
US5733855A (en) * 1994-07-26 1998-03-31 The Procter & Gamble Company Dryer-added fabric treatment article of manufacture containing antioxidant and sunscreen compounds for sun fade protection of fabrics
US5474691A (en) * 1994-07-26 1995-12-12 The Procter & Gamble Company Dryer-added fabric treatment article of manufacture containing antioxidant and sunscreen compounds for sun fade protection of fabrics
US5543083A (en) * 1994-07-26 1996-08-06 The Procter & Gamble Company Fatty amine derivatives of butylated hydroxy toluene for the protection of surfaces from physical and chemical degradation
US7396526B1 (en) 1998-11-12 2008-07-08 Johnson & Johnson Consumer Companies, Inc. Skin care composition
US20040213754A1 (en) * 2000-10-02 2004-10-28 Cole Curtis A. Method for cleansing sensitive skin using an alkanolamine
US20040191206A1 (en) * 2000-10-02 2004-09-30 Curtis Cole Methods for reduction of inflammation and erythema
US20030202951A1 (en) * 2000-12-21 2003-10-30 Curtis Cole Method for reducing the appearance of dark circles under the eyes
US6607735B2 (en) 2000-12-21 2003-08-19 Johnson & Johnson Consumer Companies, Inc. Method for reducing the appearance of dark circles under the eyes
US20080063844A1 (en) * 2001-06-29 2008-03-13 Mannington Mills, Inc. Surface coverings containing aluminum oxide
US20050238730A1 (en) * 2001-11-21 2005-10-27 Agnes Le Fur Compositions comprising an ethanolamine derivative and organic metal salts
CN109232285A (zh) * 2018-10-16 2019-01-18 新乡学院 一种具有抗菌活性的苯佐卡因双取代衍生物的合成方法和应用

Also Published As

Publication number Publication date
CH616842A5 (enrdf_load_stackoverflow) 1980-04-30
JPS50140642A (enrdf_load_stackoverflow) 1975-11-11
FR2268789B1 (enrdf_load_stackoverflow) 1979-08-17
FR2268789A1 (enrdf_load_stackoverflow) 1975-11-21
DE2509647A1 (de) 1975-11-13
GB1428648A (en) 1976-03-17
CA1064049A (en) 1979-10-09

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