US3190802A - Shaving composition and method of using same - Google Patents

Shaving composition and method of using same Download PDF

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Publication number
US3190802A
US3190802A US227528A US22752862A US3190802A US 3190802 A US3190802 A US 3190802A US 227528 A US227528 A US 227528A US 22752862 A US22752862 A US 22752862A US 3190802 A US3190802 A US 3190802A
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US
United States
Prior art keywords
shaving
pilomotor
compositions
shave
formula
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.)
Expired - Lifetime
Application number
US227528A
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English (en)
Inventor
Zeile Karl
Stahle Helmut
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.)
CH Boehringer Sohn AG and Co KG
Boehringer Ingelheim GmbH
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CH Boehringer Sohn AG and Co KG
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Publication of US3190802A publication Critical patent/US3190802A/en
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Expired - Lifetime legal-status Critical Current

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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
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • A61K8/4946—Imidazoles or their condensed derivatives, e.g. benzimidazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/30—Oxygen or sulfur atoms
    • C07D233/42—Sulfur atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q9/00—Preparations for removing hair or for aiding hair removal
    • A61Q9/02—Shaving preparations
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/30—Oxygen or sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/44—Nitrogen atoms not forming part of a nitro radical
    • C07D233/50—Nitrogen atoms not forming part of a nitro radical with carbocyclic radicals directly attached to said nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
    • C07F9/6503—Five-membered rings
    • C07F9/6506—Five-membered rings having the nitrogen atoms in positions 1 and 3
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/70—Biological properties of the composition as a whole

Definitions

  • the present invention relates to shaving compositions, such as shaving soaps, shaving sticks, brush-type shaving creams, brushless shaving creams, aerosol shaving foams, pre-shave lotions and pre-shave creams, which are composed of the customary ingredients for such compositions and, in addition, contain a compound which is stable under acid as well as alkaline conditions and produces a temporary pilomotor effect upon the hairs ofthe facial beard.
  • shaving compositions such as shaving soaps, shaving sticks, brush-type shaving creams, brushless shaving creams, aerosol shaving foams, pre-shave lotions and pre-shave creams, which are composed of the customary ingredients for such compositions and, in addition, contain a compound which is stable under acid as well as alkaline conditions and produces a temporary pilomotor effect upon the hairs ofthe facial beard.
  • compositions comprising an ingredient which produces a pilomotor effect on the facial beard are well known.
  • the concept of such compositions has heretofore been capable of application exclusively to pre-shave lotions adapted for use prior to shaving with electric dry shavers.
  • the pilomotor action of such preshave lotions is caused by the fact that the arrectus pilorum (hair follicle muscle) is contracted upon contact with the lotion and remains contracted for a period of time sufficient to last through the shaving operation or a little longer. This contraction of the arrectus pilorum causes the air stubble to be pushed further above the skin surrace line by about 0.2-0.3 mm. so that the beard hair can be cut in this position by the electric razor.
  • blade razor shaving compositions such as shaving soaps or shaving creams of the brush or brushless type, which are alkaline in character, has met with failure because they decompose under the alkaline conditions existing in blade razor shaving compositions, forming decomposition products having no pilomotor effect whatsoever.
  • Another object of the present invention is to provide a stable ingredient having a pilomotor effect for shaving compositions, such as shaving soaps and creams of the brush or brushless type as well as electric pre-shave lotions and creams.
  • Z-(phenylamino)-l,3-diazacyciopentenes-(Z) of the formula wherein R and R are selected'from the group consisting of methyl, ethyl and chlorine, and their dermatologically acceptable, non-toxic acid addition salts produce excellent pilomotor effects and are stable under acid, neutral as well as alkaline conditions, and that the above objects and advantages may be achievedby incorporating compounds of the Formula I or their non-toxic acid addition salts into customary shaving compositions, such as shaving soaps and creams of the brush, brushless or aerosol foam type or electric pro-shave lotions and creams.
  • customary shaving compositions we mean electric pre-sl1ave and blade razor shaving compositions which are described in Cosmetics, Science and Technology, edited by Edward Sagarin, Interscience Publishers, Inc., New York (1957). However, it should be understood that our invention may be practiced in conjunction with any shaving composition, regardless of whether the composition is acid, neutral or alkaline in character.
  • the compounds of the Formula I or'their non-toxic acid addition salts are advantageously added to and blended into customary shaving compositions in amounts of 0.1 to 5% by weight based on the total 'weightof the shaving composition.
  • Shaving compositions thus modified with the Z-(phenylamino) 1,3-diazacyclopentenes-(2) of the Formula I or their non-toxic acid addition salts have the advantage .of being completely stable even over long periods of storage.
  • the 2-(phenylamino)'-1,3-diazacyclopentene- (2) component imparts to. such vcompositions pilomotor properties in addition to the other properties.
  • the pilomotor eifect of shaving compositions modified in accordance with the present invention is characterized by an extraordinarily rapid onset and satisfactory duration throughout the shaving operation. i
  • the 2- (phenylarnino)-1,3-diazacyclopentene-(2) compounds of the Formula I above and their non-toxic acid addition salts are novel compounds. They, as well as a method for their preparation, are described in our copending application, filed on even date, entitled Z-(Arylamino)-l,3-Diazacycloalkenes. a
  • aqueous alcoholic solutions presents no difliculty of any kind.
  • Soaps and creams are advantageously modified with a solutlon promoter, such as glycerin or other glycols.
  • Parts 2 (2',6' diethylphenyl) amino-1,3-diazacyclopentene-(2) hydrochloride 0.50 Aidpic acid di-isopropyl ester 10.00 Ethanol 60.00 Boric acid 1.00 Perfume 0.50 Distilled water 28.00
  • Parts 2 (2',6' dimethylphenyl)-amino-1,3-diazacyclopentene-(2) 0.20 1,3-butylene glycol 4.00 Stearic acid 52.00 Coconut oil 15.00 KOH 13.30 NaOH 0.50 Perfume 1.00 Distilled water 14.00
  • the alkaline wet-shave as well as the acidic pro-shave compositions illustrated above containing the compounds of the Formula I as the active pilomotor ingredient are stable over extended periods of time and exhibit excellent pilomotor effects.
  • the quantity of pilomotor ingredient in these compositions may be varied within the percentage limits set forth above to meet particular requirements.
  • the active pilomotor ingredient according to the present invention may be incorporated into other shaving compositions with equal success.
  • the particular compounds illustrated may be replaced by any of the other compounds embraced by Formula I above or their non-toic dermatologically acceptable acid addition salts. Examples of such acid addition salts are the hydrobromide, hydroiodide, sulfate, nitrate, suocinate, maleate, tartrate, citrate and the like.
  • a shaving soap having uniformly distributed therein from 0.1 to 5% by weight, based on the total weight, of a compound selected from a group consisting of 2 (phenylamino) 1,3 -diazacyclopentenes (2) of the formula wherein R and R are selected from the group consisting of methyl, ethyl and chlorine, and their non-toxic, demratologically acceptable acid addition salts.
  • a shaving cream having uniformly distributed therein from 0.1 to 5% by weight, based on the total weight, of a compound selected from the group consisting of 2 (phenylamino) 1,3 diazacyclopentenes (2) of the formula wherein R and R are selected from the group consisting of methyl, ethyl and chlorine, and their non-toxic, dermatologically acceptable acid addition salts.
  • a shaving cream having uniformly distributed therein from 0.1 to 5% by weight, based on the total weight, of 2 (2',6-dichlorophenyl) amino-diazacyclopentene- (2).
  • a shaving soap having uniformly distributed therein from 0.1 to 5% by weight, based on the total weight, of 2-(2',6'-dimethylplrenyl)-amino 1,3 diazacyclopentene- (2).
  • the method of producing a pilomotor effect which comprises applying to the skin a compound selected from the group consisting of 2-(phenylamino)-l,3-diazacyclopentenes-( 2) of the formula wherein R and R are selected from the group consisting of methyl, ethyl and chlorine, and their non-toxic, dermatologically acceptable acid addition salts.
  • the method of producing a pilomotor effect, which 5 comprises applying to the skin 2-(2',6'-diethy1phenyl)- amino-1,3-diazacyc1opentene-(2) hydrochloride.
  • the method of producing a pilomotor effect which comprises applying to the skin 2-(2',6'-dich1oropheny1)- amino 1,3-diazacyc1opentene-(2).
  • the method of producing a pilomotor efiect which comprises applying to the skin 2-(2,6-dimethy1pheny1)- amino-1,3-diazacyclopentene- (2) 9.
  • the method of producing a pilomonor effect, which 6 comprises applying to the skin 2-(2'-chloro-6'-methy1- phenyl -a1nino- 1,3-diazacyc1opentene- (2) hydrochloride.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Epidemiology (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Birds (AREA)
  • Dermatology (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Cosmetics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
US227528A 1961-10-09 1962-10-01 Shaving composition and method of using same Expired - Lifetime US3190802A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEB0064319 1961-10-09

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US3190802A true US3190802A (en) 1965-06-22

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US227528A Expired - Lifetime US3190802A (en) 1961-10-09 1962-10-01 Shaving composition and method of using same
US227527A Expired - Lifetime US3202660A (en) 1961-10-09 1962-10-01 Process for the preparation of 3-arylamino-1, 3-diazacycloalkenes

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US227527A Expired - Lifetime US3202660A (en) 1961-10-09 1962-10-01 Process for the preparation of 3-arylamino-1, 3-diazacycloalkenes

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US (2) US3190802A (enrdf_load_stackoverflow)
CH (1) CH409980A (enrdf_load_stackoverflow)
CY (1) CY416A (enrdf_load_stackoverflow)
DK (2) DK107029C (enrdf_load_stackoverflow)
FI (1) FI42564C (enrdf_load_stackoverflow)
GB (1) GB1016514A (enrdf_load_stackoverflow)
MY (1) MY6700148A (enrdf_load_stackoverflow)
NL (2) NL6800891A (enrdf_load_stackoverflow)
SE (2) SE218182C1 (enrdf_load_stackoverflow)

Cited By (37)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3462433A (en) * 1965-10-01 1969-08-19 Boehringer Sohn Ingelheim Derivatives of 2-(2'-halo-anilino)1,3-diazacyclo-pentene-(2)
US3959160A (en) * 1973-05-16 1976-05-25 Wilkinson Sword Limited Aerosol shaving foam compositions
US4125620A (en) * 1974-10-01 1978-11-14 Boehringer Ingelheim Gmbh 2-[(2',6'-Disubstituted-phenyl)-imino]-imidazolidines and salts thereof
US4201211A (en) * 1977-07-12 1980-05-06 Alza Corporation Therapeutic system for administering clonidine transdermally
US4262005A (en) * 1978-05-31 1981-04-14 The Boots Company Limited Compounds, compositions and methods for controlling pests
US4287201A (en) * 1980-03-03 1981-09-01 Merck & Co., Inc. Anovulatory method and chicken feed compositions
US4312879A (en) * 1980-08-14 1982-01-26 Richardson-Merrell Inc. Clonidine and lofexidine as antidiarrheal agents
US4450170A (en) * 1980-07-09 1984-05-22 Beecham Group Limited Treatment of diarrhoea with 2-aminoimidazoline derivatives
US4853216A (en) * 1987-04-02 1989-08-01 Bristol-Myers Company Process and composition for the topical application of alpha1 adrenergic agonist for pilomotor effects
US20030114425A1 (en) * 1995-04-20 2003-06-19 Boehringer Ingelheim Pharma Kg Compounds and methods for treating urinary incontinence
US20070277873A1 (en) * 2006-06-02 2007-12-06 Emcore Corporation Metamorphic layers in multijunction solar cells
US20080102097A1 (en) * 2006-10-31 2008-05-01 Zanella John M Device and method for treating osteolysis using a drug depot to deliver an anti-inflammatory agent
US20090263459A1 (en) * 2008-04-18 2009-10-22 Warsaw Orthopedic, Inc. Methods and compositions for treating intervertebral disc herniations
US20090263441A1 (en) * 2008-04-18 2009-10-22 Warsaw Orthopedic, Inc. Drug depots having diffreent release profiles for reducing, preventing or treating pain and inflammation
US20090263489A1 (en) * 2008-04-18 2009-10-22 Warsaw Orthopedic, Inc. Analgesic and anti-inflammatory compositions and methods for reducing, preventing or treating pain and inflammation
US20090263448A1 (en) * 2008-04-18 2009-10-22 Warsaw Orthopedic, Inc. Clonidine Formulation in a Polyorthoester Carrier
US20090264490A1 (en) * 2008-04-18 2009-10-22 Warsaw Orthopedic, Inc. Clonidine formulations in a biodegradable polymer carrier
US20090263461A1 (en) * 2008-04-18 2009-10-22 Warsaw Orthopedic, Inc. Alpha adrenergic receptor agonists for treatment of degenerative disc disease
US20090264489A1 (en) * 2008-04-18 2009-10-22 Warsaw Orthopedic, Inc. Method for Treating Acute Pain with a Formulated Drug Depot in Combination with a Liquid Formulation
US20090264491A1 (en) * 2008-04-18 2009-10-22 Warsaw Orthopedic, Inc. Methods and compositions for treating post-operative pain comprising clonidine
US20090263460A1 (en) * 2008-04-18 2009-10-22 Warsaw Orthopedic, Inc. Medical devices and methods including polymers having biologically active agents therein
US20090263450A1 (en) * 2008-04-18 2009-10-22 Warsaw Orthopedic, Inc. Alpha adrenergic receptor agonists for treatment of inflammatory diseases
US20090263451A1 (en) * 2008-04-18 2009-10-22 Warsaw Orthopedic, Inc. Anti-Inflammatory and/or Analgesic Agents for Treatment of Myofascial Pain
US20090263462A1 (en) * 2008-04-18 2009-10-22 Warsaw Orthopedic, Inc. Methods for Treating Conditions Such as Dystonia and Post-Stroke Spasticity with Clonidine
US20090263454A1 (en) * 2008-04-18 2009-10-22 Warsaw Orthopedic, Inc. Alpha and beta adrenergic receptor agonists for treatment of pain and / or inflammation
US20090264477A1 (en) * 2008-04-18 2009-10-22 Warsaw Orthopedic, Inc., An Indiana Corporation Beta adrenergic receptor agonists for treatment of pain and/or inflammation
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US20090263321A1 (en) * 2008-04-18 2009-10-22 Warsaw Orthopedic, Inc. Compositions and Methods for Treating Post-Operative Pain Using Clonidine and Bupivacaine
US20100098746A1 (en) * 2008-10-20 2010-04-22 Warsaw Orthopedic, Inc. Compositions and methods for treating periodontal disease comprising clonidine, sulindac and/or fluocinolone
US20100137369A1 (en) * 2008-12-01 2010-06-03 Medtronic, Inc. Flowable pharmaceutical depot
US20100228097A1 (en) * 2009-03-04 2010-09-09 Warsaw Orthopedic, Inc. Methods and compositions to diagnose pain
US20100239632A1 (en) * 2009-03-23 2010-09-23 Warsaw Orthopedic, Inc. Drug depots for treatment of pain and inflammation in sinus and nasal cavities or cardiac tissue
US20110014259A1 (en) * 2009-07-17 2011-01-20 Warsaw Orthopedic, Inc. Alpha adrenergic receptor agonists for prevention or treatment of a hematoma, edema, and/or deep vein thrombosis
US20110027340A1 (en) * 2009-07-31 2011-02-03 Warsaw Orthopedic, Inc. Implantable drug depot for weight control
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US9610243B2 (en) 2008-04-18 2017-04-04 Warsaw Orthopedic, Inc. Clonidine compounds in a biodegradable polymer
USRE48948E1 (en) 2008-04-18 2022-03-01 Warsaw Orthopedic, Inc. Clonidine compounds in a biodegradable polymer

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Also Published As

Publication number Publication date
CH409980A (de) 1966-03-31
NL6800891A (enrdf_load_stackoverflow) 1968-03-25
DK104852C (da) 1966-07-11
SE301024B (enrdf_load_stackoverflow) 1968-05-20
FI42564C (fi) 1970-09-14
DK107029C (da) 1967-04-17
MY6700148A (en) 1967-12-31
SE218182C1 (enrdf_load_stackoverflow) 1968-01-16
US3202660A (en) 1965-08-24
NL6906535A (enrdf_load_stackoverflow) 1969-07-25
FI42564B (enrdf_load_stackoverflow) 1970-06-01
GB1016514A (en) 1966-01-12
CY416A (en) 1967-11-14

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