US3296077A - Pilomotor shaving compositions and method of using same - Google Patents
Pilomotor shaving compositions and method of using same Download PDFInfo
- Publication number
- US3296077A US3296077A US213609A US21360962A US3296077A US 3296077 A US3296077 A US 3296077A US 213609 A US213609 A US 213609A US 21360962 A US21360962 A US 21360962A US 3296077 A US3296077 A US 3296077A
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- United States
- Prior art keywords
- shaving
- pilomotor
- compositions
- formula
- composition
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- 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
-
- 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
-
- 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
- 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.
- 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 eifect upon the hairs of the 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 eifect upon the hairs of the facial beard.
- compositions comprising an ingredient which produces a pilometer eitect on the facial beard are well known.
- theconcept of such compositions has heretofore been capable of application exclusively to pre-shave lotions adapted for use prior to shaving with electric dryshavers.
- the pilomotor action of such pre-shave 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 suflicient to last through the shaving operation or a little longer. This contraction of the arrectus pilorum causes the hair stubble to be pushed further above the skin surface line by about 0.2-0.3 mm., so that the beard hair can be cut in this position by the electric razor.
- 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 p-re-shave lotions and creams.
- Z-amino-imidazoline compounds of the formula N x-avnf HN (I) wherein X is selected from the group consisting of naphthyl, tetrahydronaphthyl and substituents of a formula wherein R and R are selected from the group consisting of hydrogen, halogen, lower alkyl, lower alkoxy, aryl and aryloxy, 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 achieved by 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 pre-shave lotions and creams.
- customary shaving compositions such as shaving soaps and creams of the brush, brushless or aerosol foam type or electric pre-shave lotions and creams.
- customary shaving compositions I mean electric pre-shave and blade razor shaving compositions which are described in Cosmetics, Science and Technology, edited by Edward Sagarin, Inte-rscience Publishers, Inc., New York (1957). However, it should be understood that my 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 0.01 to 10%, preferably 0.1 to 1%, by weight based on the total weight of the shaving composition.
- Shaving compositions thus modified with the 2-aminoimid'azoline compounds of the Formula I or their nontoxic acid addition salts have the advantage of being completely stable even over long periods of storage.
- the imidazoline derivative component imparts to such compositions 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 extraordinary rapid onset and satisfactory duration throughout the shaving operation.
- the Z-arnino-imidazoline compounds of the Formula I above and their non-toxic acid addition salts are known compounds and may be prepared by well known methods, such as by reacting a Z-alkyl-mercapto-imidazoline with an amine of the formula X-L-NHZ wherein X has the meanings defined above in connection with Formula I.
- the sole exception is 2-(l,2',3',4'- tetrahydronaphthyl-l')-amino-imidazoline and its nontoxic acid addition salts.
- aqueous alcoholic solutions presents no difiiculty of any kind.
- Soaps and creams are advantageously modified with a solution promoter, such as glycerin or other glycols.
- Example I.Pre-shave lotion The pre-shave lotion is compounded in the usual manner from the following ingredients:
- Example lI.Shaving soap in cream form The shaving soap cream is compounded in the usual manner from the following ingredients:
- Example III -Shaving soap
- the shaving soap is compounded in the usual manner from the following ingredients:
- Example I V.Pre-shave cream
- the pre-shave cream is compounded in the usual man-
- the mildly alkaline wet-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 nontoxic, dermatologically acceptable acid addition salts. Examples of such acid addition salts are the hydrobromide, hydroiodide, sulfate, nitrate, succinate, maleate, tartrate, citrate and the like.
- An alkaline shaving composition having uniformly dispersed therethrough 0.01 to 10% 'by weight of the composition a pilomotor acting compound selected from the group consisting of 2-amino-imidazolines of the for-.
- X is selected from the group consisting of naphthyl, tetrahydronaphthyl and a radical of the formula wherein R and R are selected from the group consisting of hydrogen and halogen and their non-toxic, dermatologically-acceptable acid addition salts.
- An alkaline shaving composition having uniformly dispersed therethrough 0.01 to 10% by weight of the composition of Z-benzylamino-imidazoline hydrochloride which imparts a pilomotor effect.
- An alkaline shaving composition having uniformly dispersed therethrough 0.01 to 10% by weight of the composition of 2(l-naphthylamino)-imidazoline which im-.
- An alkaline shaving composition having uniformly dispersed therethrough 0.01 to 10% by weight of the composition 2 (1 tetrahydronaphthylamino) imidazoline which imparts a pilomotor effect.
- An alkaline shaving composition having uniformly dispersed therethrough 0.01 to 10% by weight of the composition of 2-(p-chlorobenzylamino)-imidazoline hydrochloride which imparts a pilomotor elfect.
- a method of producing a pilomotor effect on the skin which comprises applying to the skin a compound selected from the group consisting of Z-amino-imidazolines of the formula N x-Nnhf 1 EN...
- X is selected from the group consisting of naphthyl, tetrahydronaphthyl and a radical of the formula wherein R and R are selected from the group consisting of hydrogen and halogen and their non-toxic, dermatologically-acceptable acid addition salts.
- a method of producing a pilomotor efiect on the skin which comprises applying to the skin an alkaline shaving composition having dispersed therethrough 0.01 to 10% by weight of the composition of a compound selected from the group consisting of 2-amino-imidazolines of the formula N XNH-( W HN wherein X is selected from the group consisting of naphthyl, tetrahydronaphthyl and a radical of the formula wherein R and R are selected from the group consisting of hydrogen and halogen and their non-toxic, dermatologically-acceptable acid addition salts.
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
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Description
United States Patent Ofiice 3 ,296,077 Patented Jan. 3, 1967 7 Claims. 61. 167-35) 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 eifect upon the hairs of the facial beard.
Compositions comprising an ingredient which produces a pilometer eitect on the facial beard are well known. However, theconcept of such compositions has heretofore been capable of application exclusively to pre-shave lotions adapted for use prior to shaving with electric dryshavers. The pilomotor action of such pre-shave 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 suflicient to last through the shaving operation or a little longer. This contraction of the arrectus pilorum causes the hair stubble to be pushed further above the skin surface 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 ofi 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 effect 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 proposed and investigated (Arzneimittelforschung, 4 (1954), 63-66). However, the common disadvantage of those investigated compounds is that they are highly unstable under even mildly alkaline conditions. Hence, their employment as pilomotor ingredients 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 efiect whatsoever.
It is therefore an object of the present invention to provide stable acid, neutral or alkaline shaving compositions which produce not only the customary effects upon the facial beard but also a pilomotor efiect.
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 p-re-shave lotions and creams.
Other objects and advantages of the present invention will become apparent as the description thereof proceeds. I have discovered that Z-amino-imidazoline compounds of the formula N x-avnf HN (I) wherein X is selected from the group consisting of naphthyl, tetrahydronaphthyl and substituents of a formula wherein R and R are selected from the group consisting of hydrogen, halogen, lower alkyl, lower alkoxy, aryl and aryloxy, 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 achieved by 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 pre-shave lotions and creams.
By customary shaving compositions I mean electric pre-shave and blade razor shaving compositions which are described in Cosmetics, Science and Technology, edited by Edward Sagarin, Inte-rscience Publishers, Inc., New York (1957). However, it should be understood that my 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 0.01 to 10%, preferably 0.1 to 1%, by weight based on the total weight of the shaving composition.
Shaving compositions thus modified with the 2-aminoimid'azoline compounds of the Formula I or their nontoxic acid addition salts have the advantage of being completely stable even over long periods of storage. Moreover, the imidazoline derivative component imparts to such compositions 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 extraordinary rapid onset and satisfactory duration throughout the shaving operation.
The Z-arnino-imidazoline compounds of the Formula I above and their non-toxic acid addition salts are known compounds and may be prepared by well known methods, such as by reacting a Z-alkyl-mercapto-imidazoline with an amine of the formula X-L-NHZ wherein X has the meanings defined above in connection with Formula I. The sole exception is 2-(l,2',3',4'- tetrahydronaphthyl-l')-amino-imidazoline and its nontoxic acid addition salts. However, they and their preparation are described in my copending application 213,603, now abandoned, filed on even date, eititled 2-(1',2',3,4'.- Tetrahydronaphthyll -Amino-Imid azoline.
The following examples shall further illustrate the present invention and enable others skilled in the art to understand it more completely. It should be understood, however, that my 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 difiiculty of any kind. Soaps and creams are advantageously modified with a solution promoter, such as glycerin or other glycols.
Example I.Pre-shave lotion The pre-shave lotion is compounded in the usual manner from the following ingredients:
Parts 2-benzylamino-imidazoline hydrochloride 0.50 Adipic acid di-isopropyl ester 10.00 Ethanol 60.00
Boric acid 1.00 Perfume 0.50 Distilled water 28.00
Total 100.00
Example lI.Shaving soap in cream form The shaving soap cream is compounded in the usual manner from the following ingredients:
Parts 2-.( 1-naphthylamino-imidazoline 0.30 Stearic acid 18.00 Coconut oil 12.00 Potassium hydroxide 7.00 Sodium hydroxide 1.00 1,2-propylene glycol 8.00 Perfume 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-( l-tetrahydronaphthyl-amino) -imidazoline 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 I V.Pre-shave cream The pre-shave cream is compounded in the usual man- The mildly alkaline wet-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 nontoxic, dermatologically acceptable acid addition salts. Examples of such acid addition salts are the hydrobromide, hydroiodide, sulfate, nitrate, succinate, maleate, tartrate, citrate and the like.
While I have illustrated my invention with the aid of certain specific embodiments thereof, it will be readily apparent to others skilled in'the art that my invention is not limited to these embodiments and that various changes and modifications may be made without departing from the spirit of the invention or the scope of the appended claims.
I claim:
1. An alkaline shaving composition having uniformly dispersed therethrough 0.01 to 10% 'by weight of the composition a pilomotor acting compound selected from the group consisting of 2-amino-imidazolines of the for-.
mula
N XNH( HN.
wherein X is selected from the group consisting of naphthyl, tetrahydronaphthyl and a radical of the formula wherein R and R are selected from the group consisting of hydrogen and halogen and their non-toxic, dermatologically-acceptable acid addition salts.
2. An alkaline shaving composition having uniformly dispersed therethrough 0.01 to 10% by weight of the composition of Z-benzylamino-imidazoline hydrochloride which imparts a pilomotor effect.
3. An alkaline shaving composition having uniformly dispersed therethrough 0.01 to 10% by weight of the composition of 2(l-naphthylamino)-imidazoline which im-.
parts a pilomotor effect.
4. An alkaline shaving composition having uniformly dispersed therethrough 0.01 to 10% by weight of the composition 2 (1 tetrahydronaphthylamino) imidazoline which imparts a pilomotor effect.
5. An alkaline shaving composition having uniformly dispersed therethrough 0.01 to 10% by weight of the composition of 2-(p-chlorobenzylamino)-imidazoline hydrochloride which imparts a pilomotor elfect.
6. A method of producing a pilomotor effect on the skin which comprises applying to the skin a compound selected from the group consisting of Z-amino-imidazolines of the formula N x-Nnhf 1 EN...
wherein X is selected from the group consisting of naphthyl, tetrahydronaphthyl and a radical of the formula wherein R and R are selected from the group consisting of hydrogen and halogen and their non-toxic, dermatologically-acceptable acid addition salts.
7. A method of producing a pilomotor efiect on the skin which comprises applying to the skin an alkaline shaving composition having dispersed therethrough 0.01 to 10% by weight of the composition of a compound selected from the group consisting of 2-amino-imidazolines of the formula N XNH-( W HN wherein X is selected from the group consisting of naphthyl, tetrahydronaphthyl and a radical of the formula wherein R and R are selected from the group consisting of hydrogen and halogen and their non-toxic, dermatologically-acceptable acid addition salts.
References Cited by the Examiner 5 FOREIGN PATENTS 1,032,482 6/1958 Germany.
OTHER REFERENCES Arzneimittel Forschung, vol. 4, 1954, pp. 63-67.
10 Chem. Abs, vol. 54, pp. 588-589.
JULIAN S. LEVITI, Primary Examiner.
FRANK CACCIAPAGLIA, JR., Examiner.
15 A. P. FAGELSON, Assistant Examiner.
Claims (1)
1. AN ALKALINE SHAVING COMPOSITION HAVING UNIFORMLY DISPERSED THERETHROUGH 0.01 TO 10% BY WEIGHT OF THE COMPOSITION A PILOMOTOR ACTING COMPOUND SELECTED FROM THE GROUP CONSISTING OF 2-AMINO-IMIDAZOLINES OF THE FORMULA
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DET20557A DE1147712B (en) | 1961-08-04 | 1961-08-04 | Shaving preparations with pilomotor activity |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3296077A true US3296077A (en) | 1967-01-03 |
Family
ID=7549753
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US213609A Expired - Lifetime US3296077A (en) | 1961-08-04 | 1962-07-31 | Pilomotor shaving compositions and method of using same |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3296077A (en) |
| CH (1) | CH416946A (en) |
| DE (1) | DE1147712B (en) |
| FI (1) | FI41059B (en) |
| GB (1) | GB943943A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4036972A (en) * | 1973-02-23 | 1977-07-19 | Boehringer Ingelheim Gmbh | 2-(N-thienylmethyl-phenylamino)-imidazolines-(2) and salts thereof |
| US4125620A (en) * | 1974-10-01 | 1978-11-14 | Boehringer Ingelheim Gmbh | 2-[(2',6'-Disubstituted-phenyl)-imino]-imidazolidines and salts thereof |
| 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 |
| US5688497A (en) * | 1996-09-04 | 1997-11-18 | Warner-Lambert Company | Shaving aid with physiological cooling effect |
| US20150224080A1 (en) * | 2008-06-09 | 2015-08-13 | Allergan, Inc. | Methods of treating alpha adrenergic mediated conditions |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4046874A (en) * | 1974-02-13 | 1977-09-06 | Mead Johnson & Company | Soapless shave composition |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1032482B (en) * | 1956-12-22 | 1958-06-19 | Thomae Gmbh Dr K | Skin pretreatment agents for shaving, especially for electric shaving |
-
1961
- 1961-08-04 DE DET20557A patent/DE1147712B/en active Pending
-
1962
- 1962-07-16 CH CH852762A patent/CH416946A/en unknown
- 1962-07-27 GB GB29011/62A patent/GB943943A/en not_active Expired
- 1962-07-31 US US213609A patent/US3296077A/en not_active Expired - Lifetime
- 1962-08-03 FI FI1461/62A patent/FI41059B/fi active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1032482B (en) * | 1956-12-22 | 1958-06-19 | Thomae Gmbh Dr K | Skin pretreatment agents for shaving, especially for electric shaving |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4036972A (en) * | 1973-02-23 | 1977-07-19 | Boehringer Ingelheim Gmbh | 2-(N-thienylmethyl-phenylamino)-imidazolines-(2) and salts thereof |
| US4125620A (en) * | 1974-10-01 | 1978-11-14 | Boehringer Ingelheim Gmbh | 2-[(2',6'-Disubstituted-phenyl)-imino]-imidazolidines and salts thereof |
| 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 |
| US5688497A (en) * | 1996-09-04 | 1997-11-18 | Warner-Lambert Company | Shaving aid with physiological cooling effect |
| US20150224080A1 (en) * | 2008-06-09 | 2015-08-13 | Allergan, Inc. | Methods of treating alpha adrenergic mediated conditions |
| US9623006B2 (en) * | 2008-06-09 | 2017-04-18 | Allergan, Inc. | Methods of treating α adrenergic mediated conditions |
| US9849113B2 (en) | 2008-06-09 | 2017-12-26 | Allergan, Inc. | Methods of treating α adrenergic mediated conditions |
Also Published As
| Publication number | Publication date |
|---|---|
| FI41059B (en) | 1969-04-30 |
| GB943943A (en) | 1963-12-11 |
| DE1147712B (en) | 1963-04-25 |
| CH416946A (en) | 1966-07-15 |
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