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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Prior art keywords
shaving
pilomotor
compositions
shave
formula
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US227528A
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Zeile Karl
Stahle Helmut
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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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    • 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
    • A61K31/00Medicinal preparations containing organic active ingredients
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILET PREPARATIONS
    • A61Q9/00Preparations for removing hair or for aiding hair removal
    • A61Q9/02Shaving preparations
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D233/00Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04Heterocyclic 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
    • C07D233/28Heterocyclic 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
    • C07D233/30Oxygen or sulfur atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D233/00Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04Heterocyclic 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
    • C07D233/28Heterocyclic 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
    • C07D233/30Oxygen or sulfur atoms
    • C07D233/42Sulfur atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D233/00Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04Heterocyclic 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
    • C07D233/28Heterocyclic 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
    • C07D233/44Nitrogen atoms not forming part of a nitro radical
    • C07D233/50Nitrogen atoms not forming part of a nitro radical with carbocyclic radicals directly attached to said nitrogen atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic System
    • C07F9/02Phosphorus compounds
    • C07F9/547Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/645Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
    • C07F9/6503Five-membered rings
    • C07F9/6506Five-membered rings having the nitrogen atoms in positions 1 and 3
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/70Biological properties of the composition as a whole
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S514/00Drug, bio-affecting and body treating compositions
    • Y10S514/93Vasoconstrictor, nondecongestant

Description

United States Patent 9 Claims. (a. 16785) This invention relates to shaving compositions and especially to improved shaving compositions adapted for use in conjunction with blade razors as well as electric razors.

More particularly, 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.

Compositions comprising an ingredient which produces a pilomotor effect on the facial beard are well known. However, 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. When the contracting effects of the lotion wear off after completion of the shaving operation and the tonus of the hair follicle muscle returns to normal, the cut beard hair retracts to a point substantially below the skin surface line, giving the eifect of what is commonly referred to as a close shave. There is the further, advantage that men with a heavy beard and rapid beard growth can maintain a presentable appearance for longer periods of time and need to shave only once a day instead of twice.

A number of compounds having a pilomotor effect have been pioposed and investigated (Arzneimittelforschung, 4 (1954), 63-66). However, the common disadvantage of those investigated compounds is that they are highly unstable under evenmildl-y alkalineconditions. Hence, their employment as pilomotoringredients has been necessarily confined to compositions which are acidic in character, notably to acidic pre-shave lotions adapted for use in conjunction with electric dry shavers. Any attempt to incorporate them into 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. i

It is, therefore, an. object ofthe present invention to provide stablelacid, neutral or alkaline shaving composiamassz Patented June 22, 1955 tions which produce not only the customary eifects upon the facial beard but also a pilomotor effect.

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.

Other objects and advantages of the present invention will become apparent as the description thereof proceeds.

We have discovered that 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.

By 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. Moreover, 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

The' following examples shall further illustrate the present invention and enable others skilled in the art to understand it morecompletely. It should be understood, however, that our invention is not limited to these particular examples. The parts are parts by weight.

Since the active ingredients with pilomotor activity according to the present invention are readily soluble in water and alcohol, the preparation of 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.

EXAMPLE I Pro-shave lotion The pre-shave lotion is compounded in the usual manner from the following ingredients:

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

Total 100.00

EXAMPLE II Shaving soap in cream form The shaving soap cream is compounded in the usual manner from the following ingredients:

Parts 2 (2,6' dichlorophenyl) amino diazacyclopentene-(2) 0.30 Stearic acid 18.00 Coconut oil 12.00 Potassium hydroxide 7.00 Sodium hydroxide 1.00 Stearyl alcohol 0.70 Distilled Water 42.00

Total 100.00

EXAMPLE III Shaving soap The shaving soap is compounded in the usual manner from the following ingredients:

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

Total 100.00

EXAMPLE IV Pre-shave cream The pre-shave cream is compounded in the usual manner from the following ingredients:

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. Of course, the quantity of pilomotor ingredient in these compositions may be varied within the percentage limits set forth above to meet particular requirements. Moreover, the active pilomotor ingredient according to the present invention may be incorporated into other shaving compositions with equal success. Finally, 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.

While We have illustrated our invention with the aid of certain specific embodiments thereof, it Will be readily apparent to others skilled in the art that our invention is not limited to these embodiments and that various changes and modificaions may be made Without departing from the spirit of the invention or the scope of the appended claims.

We claim:

1. 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.

2. 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.

3. 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).

4. 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).

5. 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.

6. The method of producing a pilomotor effect, which 5 comprises applying to the skin 2-(2',6'-diethy1phenyl)- amino-1,3-diazacyc1opentene-(2) hydrochloride.

7. The method of producing a pilomotor effect, which comprises applying to the skin 2-(2',6'-dich1oropheny1)- amino 1,3-diazacyc1opentene-(2).

8. 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.

References Cited by the Examiner Najer: B111. Soc. Chem, France, No. 19 61, 2114-2126.

JULIAN S. LEVITT, Primary Examiner.

FRANK CACCIAPAGLIA, JR., Examiner.

atent No. 3,190,802 June 22, 1965 Karl Zeile et al.

It is hereby certified that ent requiring correction and the corrected below.

error appears in the above numbered patt the said Letters Patent should read as Column 4, lines 65 to 70, the formula should appear as shown below instead of as in the patent:

2 NHC\ 1| 1 CH 2 H EAL) Signed and sealed this 28th day of December 1965.

test:

NEST W. SWIDER EDWARD J. BRENNER testing Officer Commissioner of Patents

Claims (1)

1. A SHAVING SOAP HAVING UNIFORMLY DISTRIBUTED THEREIN FROM 0.1 TO 5% BY WEIGHT, BASES ON THE TOTAL WEIGHT, OF A COMPOUND SELECTED FROM A GROUP CONSISTING OF 2 - (PHENYLAMINO) - 1,3 - DIAZACYCLOPENTENES - (2) OF THE FORMULA
US227528A 1961-10-09 1962-10-01 Shaving composition and method of using same Expired - Lifetime US3190802A (en)

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DK (2) DK104852C (en)
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GB (1) GB1016514A (en)
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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
US20090263460A1 (en) * 2008-04-18 2009-10-22 Warsaw Orthopedic, Inc. Medical devices and methods including polymers having biologically active agents therein
US20090263462A1 (en) * 2008-04-18 2009-10-22 Warsaw Orthopedic, Inc. Methods for Treating Conditions Such as Dystonia and Post-Stroke Spasticity with Clonidine
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
US20090263463A1 (en) * 2008-04-18 2009-10-22 Warsaw Orthopedic, Inc. Alpha adrenergic receptor agonists for treatment of pain and/or inflammation
US20090263450A1 (en) * 2008-04-18 2009-10-22 Warsaw Orthopedic, Inc. Alpha adrenergic receptor agonists for treatment of inflammatory diseases
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
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
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US6090846A (en) * 1994-06-01 2000-07-18 Glaxo Wellcome Inc. Substituted urea and isothiourea derivatives as no synthase inhibitors
US5801188A (en) * 1997-01-08 1998-09-01 Medtronic Inc. Clonidine therapy enhancement
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US3202660A (en) 1965-08-24
FI42564C (en) 1970-09-14
NL6906535A (en) 1969-07-25
DK107029C (en) 1967-04-17
FI42564B (en) 1970-06-01
CY416A (en) 1967-11-14
SE301024B (en) 1968-05-20
NL6800891A (en) 1968-03-25
CH409980A (en) 1966-03-31
GB1016514A (en) 1966-01-12
MY6700148A (en) 1967-12-31
DK104852C (en) 1966-07-11

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