US3331743A - Cyclohexylcyclohexanone in mercaptoacetate hair-treating compositions - Google Patents
Cyclohexylcyclohexanone in mercaptoacetate hair-treating compositions Download PDFInfo
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- US3331743A US3331743A US363299A US36329964A US3331743A US 3331743 A US3331743 A US 3331743A US 363299 A US363299 A US 363299A US 36329964 A US36329964 A US 36329964A US 3331743 A US3331743 A US 3331743A
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- Prior art keywords
- hair
- cyclohexylcyclohexanone
- solution
- mercaptoacetate
- odor
- Prior art date
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- JLYNSPSTPQAEAX-UHFFFAOYSA-N 4-cyclohexylcyclohexan-1-one Chemical compound C1CC(=O)CCC1C1CCCCC1 JLYNSPSTPQAEAX-UHFFFAOYSA-N 0.000 title claims description 11
- 239000000203 mixture Substances 0.000 title description 14
- CWERGRDVMFNCDR-UHFFFAOYSA-M thioglycolate(1-) Chemical compound [O-]C(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-M 0.000 title description 8
- 238000002360 preparation method Methods 0.000 claims description 20
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical class OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 claims description 14
- 239000002537 cosmetic Substances 0.000 claims description 9
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 6
- 150000001340 alkali metals Chemical class 0.000 claims description 6
- 239000012670 alkaline solution Substances 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 2
- 150000001342 alkaline earth metals Chemical class 0.000 claims 1
- 239000000243 solution Substances 0.000 description 24
- 235000019645 odor Nutrition 0.000 description 15
- 230000002951 depilatory effect Effects 0.000 description 13
- -1 alkaline earth metal mercaptoacetates Chemical class 0.000 description 11
- UOBQDYFTAJKQAL-UHFFFAOYSA-N 2-cyclohexylcyclohexan-1-one Chemical compound O=C1CCCCC1C1CCCCC1 UOBQDYFTAJKQAL-UHFFFAOYSA-N 0.000 description 6
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 6
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 4
- 102000011782 Keratins Human genes 0.000 description 4
- 108010076876 Keratins Proteins 0.000 description 4
- LEVWYRKDKASIDU-IMJSIDKUSA-N L-cystine Chemical compound [O-]C(=O)[C@@H]([NH3+])CSSC[C@H]([NH3+])C([O-])=O LEVWYRKDKASIDU-IMJSIDKUSA-N 0.000 description 4
- 229960003067 cystine Drugs 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 3
- 239000002304 perfume Substances 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 150000003464 sulfur compounds Chemical class 0.000 description 3
- 239000002562 thickening agent Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- ZZTCCAPMZLDHFM-UHFFFAOYSA-N ammonium thioglycolate Chemical compound [NH4+].[O-]C(=O)CS ZZTCCAPMZLDHFM-UHFFFAOYSA-N 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 230000035617 depilation Effects 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000006210 lotion Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 229920000609 methyl cellulose Polymers 0.000 description 2
- 239000001923 methylcellulose Substances 0.000 description 2
- 235000010981 methylcellulose Nutrition 0.000 description 2
- 230000001473 noxious effect Effects 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 230000000754 repressing effect Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- PVSNMDAHWMHSBD-UHFFFAOYSA-N 1-cyclohexylcyclohexan-1-ol Chemical compound C1CCCCC1C1(O)CCCCC1 PVSNMDAHWMHSBD-UHFFFAOYSA-N 0.000 description 1
- XWNSFEAWWGGSKJ-UHFFFAOYSA-N 4-acetyl-4-methylheptanedinitrile Chemical compound N#CCCC(C)(C(=O)C)CCC#N XWNSFEAWWGGSKJ-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000004153 Potassium bromate Substances 0.000 description 1
- 206010040880 Skin irritation Diseases 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- HDFRDWFLWVCOGP-UHFFFAOYSA-N carbonothioic O,S-acid Chemical class OC(S)=O HDFRDWFLWVCOGP-UHFFFAOYSA-N 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910052945 inorganic sulfide Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229940094037 potassium bromate Drugs 0.000 description 1
- 235000019396 potassium bromate Nutrition 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000036556 skin irritation Effects 0.000 description 1
- 231100000475 skin irritation Toxicity 0.000 description 1
- 159000000008 strontium salts Chemical class 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- 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
- A61Q9/04—Depilatories
-
- 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
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/35—Ketones, e.g. benzophenone
-
- 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
- A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/04—Preparations for permanent waving or straightening the hair
Definitions
- compositions for the conditioning or removal of human hair for cosmetic purposes are known in the art. These compositions usually contain a sulfur compound, preferably'organic, capable of reducing the cystine disulfide linkages of the keratin component of hair under alkaline conditions.
- a mercaptan or mercapto carboxylic acid salt e.g., mercaptoacetic acid salt
- water the pH of the solution adjusted to a suitable alkaline value generally between about 8.5 and 10.5
- the resulting alkaline solution applied to the hair in order to soften or relax and condition the hair for change in configuration.
- the treated hair is manipulated to a desired configuration which is then set by treating the hair with a solution of an oxidizing agent, such as potassium bromate or hydrogen peroxide.
- chemical depilatories have been known for sometime and are usually based on inorganic sulfides, mercaptans or mercaptoacetic acid salts.
- the generally preferred depilatory preparations are in cream or paste form suitable for easy application to localized areas of the human skin.
- the chemical depilatories act by reducing the cystine disulfide linkages of the keratin molecule in human hair.
- the resulting sulfhydryl degradation products react with the alkali present in the depilatory to cause swelling and disintegration of the hair.
- the pH value should be above about 11 for rapid, effective depilation; lower pH values require longer contact time with subsequent skin irritation due to the alkali present.
- Keratin is a protein composed of a number of amino acids including cystine, and it is the cystine components that provide the lateral disulfide linkages between the polypeptide chains in the protein fibers.
- An object of the present invention is to provide novel hair-treating cosmetic preparations based on mercaptoacetates.
- a further object is to produce novel depilatory compositions which do not deteriorate on prolonged storage.
- the production of novel cold permanent hair waving solutions is another object of the invention.
- Aqueous alkaline mercaptoacetate hair-treating compositions in which 2-cyclohexylcycylohexanone can be effectively employed may contain additives, such as for example, methyl cellulose or polystyrene thickening agents, wetting agents and emulsifiers, etc., as illustrated in U.S.P. 2,631,965, 2,689,815, 2,719,815 (relating to hair waving solutions) and U.S.P. 2,352,524 and 2,823,168 (relating to depilatory compositions).
- mercaptoacetate preparations for treating hair contain between about 4% to 7% by weight of mercaptoacetic acid in the form of the ammonium, alkali metal or alkaline earth metal salt.
- the mercaptoacetate compositions preferably have a pH value between about 8.5 and 10.5, while for depilatory use they possess a pH- value from about 10 to about 12.5.
- the cold permanent waving solutions usually contain ammonium mercaptoacetate together with thickeners, notably methyl cellulose in amount of about 1-10% by weight of the total solution.
- the depilatory compositions preferably have a pH value of from about 10.0 to 12.5 and contain the calcium or strontium salt of mercaptoacetic acid generally together with suitable thickeners, clays, etc. to provide desired liquid or paste type compositions.
- the lotions so obtained are not discolored nor do they develop objectionable sulfide odor on storage at room temperature for 34 days whereas the solution to which no addition Was made, developed a strong sulfide odor on standing under the same conditions.
- the odor repressing agent of this invention is a colorless to pale yellow liquid having a pleasing odor.
- it may contain the isomeric 4-cyclohexylcyclohexanone in various amounts.
- the commercially available product may also contain relatively small amounts (i.e., less than 5% by weight) of cyclohexanone, cyclohexanol and or cyclohexylcyclohexanol. Such small amounts do not affect the 4 odor repressing properties of 2-cyclohexylcyclohexanone and act as non-reactive diluents at worst.
- 4-cyclohexylcyclohexanone can be used in place of the more common Z-cyclohexylcyclohexanone with similar results.
- a cosmetic preparation for the treatment of hair comprising an alkaline solution of a mercaptoacetic acid salt selected from the group consisting of ammonium, alkali metal and alkaline earth metal mercaptoacetates and an amount of cyclohexylcyclohexanone suflicient to effectively repressthe sulfide-type odor produced bythe mercaptoaceate compound.
- a mercaptoacetic acid salt selected from the group consisting of ammonium, alkali metal and alkaline earth metal mercaptoacetates and an amount of cyclohexylcyclohexanone suflicient to effectively repressthe sulfide-type odor produced bythe mercaptoaceate compound.
- a cosmetic preparation for the treatment of hair comprising a solution of a mercaptoacetic acid salt selected from the group consisting of ammonium, alkali metal and alkaline earth metal mercaptoacetates, said solution having a pH value in excess of 8.5 but not exceeding about 12.5 and an amount'of 'cyclohexylcyclohexanone suflicient to efiectivelyrepress the sulfide-type odor of the preparation.
- a cosmetic preparation for the treatment of hair comprising a solution of a mercaptoacetic acid salt selected from the group consisting of ammonium, alkali metal and alkaline earth metal mercaptoacetates, said solution having a pH value in excess of 8.5 but not exceeding about 12.5 and from about 0.15%'to about 2.0% 'by weight of cyclohexylcyclohexanone.
- a hair waving preparation comprising a solution of ammonium mercaptoacetate having a pH value of from 8.5 to 10.5 and from about 0.15% to about 2.0% by weight of cyclohexylcyclohexanone.
- a depilatory formulation comprising a solution of alkaline earth metal mercaptoacetate, said solution having a pH value of from about 10.5 to about 12.5 .and from' about 0.15% to about 2.0% by weight of cyclohexylcyclohexanone.
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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)
- Emergency Medicine (AREA)
- Cosmetics (AREA)
Description
United States Patent 3,331,743 CYCLOHEXYLCYCLOHEXANONE IN MERCAPTO- ACETATE HAIR-TREATING COMPOSITIONS Marvin K. Cook, Brooklyn, N.Y., assignor to Allied Chemical Corporation, New York, N.Y., a corporation of New York No Drawing. Filed Apr. 28, 1964, Ser. No. 363,299 5 Claims. (Cl. 16787.1)
ABSTRACT OF THE DISCLOSURE Novel cosmetic preparations for the treatment of hair comprising ammonium, alkali metal and alkaline earth metal mercaptoacetates in combination with cycylohexylcyclohexanone which do not deteriorate on storage and which are substantially free of unpleasant sulfide odors normally characteristic of such preparations.
Compositions for the conditioning or removal of human hair for cosmetic purposes are known in the art. These compositions usually contain a sulfur compound, preferably'organic, capable of reducing the cystine disulfide linkages of the keratin component of hair under alkaline conditions.
For example, in the generally known method of waving hair by the cold permanent waving process, a mercaptan or mercapto carboxylic acid salt (e.g., mercaptoacetic acid salt) is dissolved in water, the pH of the solution adjusted to a suitable alkaline value generally between about 8.5 and 10.5, and the resulting alkaline solution applied to the hair in order to soften or relax and condition the hair for change in configuration. The treated hair is manipulated to a desired configuration which is then set by treating the hair with a solution of an oxidizing agent, such as potassium bromate or hydrogen peroxide.
Further, chemical depilatories have been known for sometime and are usually based on inorganic sulfides, mercaptans or mercaptoacetic acid salts. The generally preferred depilatory preparations are in cream or paste form suitable for easy application to localized areas of the human skin. The chemical depilatories act by reducing the cystine disulfide linkages of the keratin molecule in human hair. The resulting sulfhydryl degradation products react with the alkali present in the depilatory to cause swelling and disintegration of the hair. In general, the pH value should be above about 11 for rapid, effective depilation; lower pH values require longer contact time with subsequent skin irritation due to the alkali present.
The use of the aforementioned sulfur compounds in hair-treating preparations, either for cold permanent waving or depilation of the hair, is based on the ability of the sulfur compounds to rupture the disulfide linkages of the keratin fibers. Keratin is a protein composed of a number of amino acids including cystine, and it is the cystine components that provide the lateral disulfide linkages between the polypeptide chains in the protein fibers.
A common defect of hair-treating preparations containing mercapto compounds e.g. mercaptoacetates, is development of a hydrogen sulfide or similar noxious odor. It is known to employ perfuming agents in hair-treating compositions; the choice of perfuming agent is restricted by the relatively high alkalinity of the preparations. Thus, the use of saponifiable esters or aldolizable aldehydes is inadvisable. Also the presence of the -SH group may cause conversion of perfume alcohols to malodorous mercaptans.
An object of the present invention is to provide novel hair-treating cosmetic preparations based on mercaptoacetates. A further object is to produce novel depilatory compositions which do not deteriorate on prolonged storage. The production of novel cold permanent hair waving solutions is another object of the invention.
These objects are attained by the incorporation of 2- cyclohexylcyclohexanone in the alkaline mercaptoacetate containing hair-treating preparation in an amount sufiicient to mask the noxious odors generally associated with such compositions. Only small amounts of 2-cyclohexylcyclohexanone are required and a preferred effective amount to use is from about 0.15% to about 2.0% of the total weight of the cosmetic preparation.
Aqueous alkaline mercaptoacetate hair-treating compositions in which 2-cyclohexylcycylohexanone can be effectively employed may contain additives, such as for example, methyl cellulose or polystyrene thickening agents, wetting agents and emulsifiers, etc., as illustrated in U.S.P. 2,631,965, 2,689,815, 2,719,815 (relating to hair waving solutions) and U.S.P. 2,352,524 and 2,823,168 (relating to depilatory compositions). Generally, commercial mercaptoacetate preparations for treating hair contain between about 4% to 7% by weight of mercaptoacetic acid in the form of the ammonium, alkali metal or alkaline earth metal salt. For use in cold permanent hair waving the mercaptoacetate compositions preferably have a pH value between about 8.5 and 10.5, while for depilatory use they possess a pH- value from about 10 to about 12.5. The cold permanent waving solutions usually contain ammonium mercaptoacetate together with thickeners, notably methyl cellulose in amount of about 1-10% by weight of the total solution. The depilatory compositions preferably have a pH value of from about 10.0 to 12.5 and contain the calcium or strontium salt of mercaptoacetic acid generally together with suitable thickeners, clays, etc. to provide desired liquid or paste type compositions.
The preparation of the novel hair-treating cosmetic preparations of this invention will be described in the 'following examples. It is to be understood however, that these examples are merely illustrative and are not intended to limit the scope of the invention claimed herein. All parts given are by weight, except where otherwise noted.
EXAMPLE I Preparation 0 hair waving solution Typical commercial mercaptoacetate hair waving lotions containing about 6.5% mercaptoacetic acid sufiicient ammonium hydroxide to give the solution a pH value about 9.2 were prepared from the following components:
[Amounts expressed as percent by volume] *Tween is a polyoxyethylene sorbitan monooleate produced by Atlas Chemical Industries.
The lotions so obtained are not discolored nor do they develop objectionable sulfide odor on storage at room temperature for 34 days whereas the solution to which no addition Was made, developed a strong sulfide odor on standing under the same conditions.
Human hair swatches were immersed for 30 minutes in separate containers of these cold wave solutions. Solu- W 7 3 tion (a) was the commercial mercaptoacetate wave prep? aration whereas solution (b) contained the addition of 0.5% of 2-cyclohexylcyclohexanone and solution contained 1.0% 2 cyclohexylcyclohexanone. The hair swatches were removed from the softening or wave solution, treated with potassium bromate-neutralizer solution and rinsed.
Hair swatches:
7 Solution (a) Appreciable sulfide odor- Solution (b) No odor. Solution (c) No odor.
' EXAMPLE I1 Depilatory composition A conventional depilatory preparation having a pH of 11.0 was produced from the following ingredients: cetyl alcohol (8 parts), stearyl alcohol (8 parts), calcium mer- The depilatory was applied to the skin, allowed to remain in contact for about five minutes before washing off with water. The sample of depilatory containing no cyclohexylcyclohexanone developed an unpleasant sulfide odor that persisted on theskin even after repeated washing.
The samples containing 2-cyclohexylcyclohexanone did not develop any sulfide" odor and the skin after washing was clean with a pleasant odor.
The odor repressing agent of this invention 2-cycl0- hexylcyclohexanone is a colorless to pale yellow liquid having a pleasing odor. As obtained commercially it may contain the isomeric 4-cyclohexylcyclohexanone in various amounts. The commercially available product may also contain relatively small amounts (i.e., less than 5% by weight) of cyclohexanone, cyclohexanol and or cyclohexylcyclohexanol. Such small amounts do not affect the 4 odor repressing properties of 2-cyclohexylcyclohexanone and act as non-reactive diluents at worst. For the purposes of this invention, 4-cyclohexylcyclohexanone can be used in place of the more common Z-cyclohexylcyclohexanone with similar results.
I claim:
1. A cosmetic preparation for the treatment of hair comprising an alkaline solution of a mercaptoacetic acid salt selected from the group consisting of ammonium, alkali metal and alkaline earth metal mercaptoacetates and an amount of cyclohexylcyclohexanone suflicient to effectively repressthe sulfide-type odor produced bythe mercaptoaceate compound. V V
2. A cosmetic preparation for the treatment of hair comprising a solution of a mercaptoacetic acid salt selected from the group consisting of ammonium, alkali metal and alkaline earth metal mercaptoacetates, said solution having a pH value in excess of 8.5 but not exceeding about 12.5 and an amount'of 'cyclohexylcyclohexanone suflicient to efiectivelyrepress the sulfide-type odor of the preparation. 7
3. A cosmetic preparation for the treatment of hair comprising a solution of a mercaptoacetic acid salt selected from the group consisting of ammonium, alkali metal and alkaline earth metal mercaptoacetates, said solution having a pH value in excess of 8.5 but not exceeding about 12.5 and from about 0.15%'to about 2.0% 'by weight of cyclohexylcyclohexanone. V
4. A hair waving preparation comprising a solution of ammonium mercaptoacetate having a pH value of from 8.5 to 10.5 and from about 0.15% to about 2.0% by weight of cyclohexylcyclohexanone. V
5. A depilatory formulation comprising a solution of alkaline earth metal mercaptoacetate, said solution having a pH value of from about 10.5 to about 12.5 .and from' about 0.15% to about 2.0% by weight of cyclohexylcyclohexanone.
References Cited UNITED STATES PATENTS 3,124,614 3/1964 Dankert et al l67 94 X ALBERT T. MEYERS, Primary Examiner. SAM ROSEN, Examiner.
VERA C. CLARKE, Assistant Examiner.
Claims (1)
1. A COSMETIC PREPARATION FOR THE TREATMENT OF HAIR COMPRISING AN ALKALINE SOLUTION OF A MERCAPTOACETIC ACID SALT SELECTED FROM THE GROUP CONSISTING OF AMMONIUM, ALKALI METAL AND ALKALINE EARTH METAL MERCAPTOACETATES AND AN AMOUNT OF CYCLOHEXYLCYCLOHEXANONE SUFFICIENT TO EFFECTIVELY REPRESS THE SULFIDE-TYPE ODOR PRODUCED BY THE MERCAPTOACEATE COMPOUND.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US363299A US3331743A (en) | 1964-04-28 | 1964-04-28 | Cyclohexylcyclohexanone in mercaptoacetate hair-treating compositions |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US363299A US3331743A (en) | 1964-04-28 | 1964-04-28 | Cyclohexylcyclohexanone in mercaptoacetate hair-treating compositions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3331743A true US3331743A (en) | 1967-07-18 |
Family
ID=23429656
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US363299A Expired - Lifetime US3331743A (en) | 1964-04-28 | 1964-04-28 | Cyclohexylcyclohexanone in mercaptoacetate hair-treating compositions |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US3331743A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3971391A (en) * | 1973-03-08 | 1976-07-27 | L'oreal | Process for improving the quality of living, human hair by lanthionization |
| FR2551973A1 (en) * | 1983-09-20 | 1985-03-22 | Shiseido Co Ltd | NEUTRALIZATION AGENT FOR COLD PERMANENT |
| FR2563430A1 (en) * | 1982-11-08 | 1985-10-31 | Shiseido Co Ltd | WAVE LOTION FOR PERMANENT COLD |
| FR2563429A1 (en) * | 1982-11-08 | 1985-10-31 | Shiseido Co Ltd | WAVE LOTION FOR PERMANENT COLD |
| US5319136A (en) * | 1993-09-10 | 1994-06-07 | Elf Atochem North America, Inc. | Preparation of pure ammonium thioglycolate |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3124614A (en) * | 1964-03-10 | Preparation of z-substituteb |
-
1964
- 1964-04-28 US US363299A patent/US3331743A/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3124614A (en) * | 1964-03-10 | Preparation of z-substituteb |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3971391A (en) * | 1973-03-08 | 1976-07-27 | L'oreal | Process for improving the quality of living, human hair by lanthionization |
| FR2563430A1 (en) * | 1982-11-08 | 1985-10-31 | Shiseido Co Ltd | WAVE LOTION FOR PERMANENT COLD |
| FR2563429A1 (en) * | 1982-11-08 | 1985-10-31 | Shiseido Co Ltd | WAVE LOTION FOR PERMANENT COLD |
| FR2551973A1 (en) * | 1983-09-20 | 1985-03-22 | Shiseido Co Ltd | NEUTRALIZATION AGENT FOR COLD PERMANENT |
| US5319136A (en) * | 1993-09-10 | 1994-06-07 | Elf Atochem North America, Inc. | Preparation of pure ammonium thioglycolate |
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