US3173842A - Process for waving human hair with 2, 5-dimercaptothiodiazoline - Google Patents
Process for waving human hair with 2, 5-dimercaptothiodiazoline Download PDFInfo
- Publication number
- US3173842A US3173842A US306308A US30630863A US3173842A US 3173842 A US3173842 A US 3173842A US 306308 A US306308 A US 306308A US 30630863 A US30630863 A US 30630863A US 3173842 A US3173842 A US 3173842A
- Authority
- US
- United States
- Prior art keywords
- hair
- waving
- solution
- dimercaptothiodiazoline
- human hair
- 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
Links
- 210000004209 hair Anatomy 0.000 title claims description 51
- 241000282414 Homo sapiens Species 0.000 title claims description 17
- 238000000034 method Methods 0.000 title claims description 16
- 230000008569 process Effects 0.000 title claims description 16
- LNKFHGOACPMJKQ-UHFFFAOYSA-N 2,5-bis(disulfanyl)-3,4-dihydropyrazole Chemical compound SSN1CCC(SS)=N1 LNKFHGOACPMJKQ-UHFFFAOYSA-N 0.000 title claims description 11
- 239000007864 aqueous solution Substances 0.000 claims description 10
- 239000000243 solution Substances 0.000 description 28
- 238000011282 treatment Methods 0.000 description 10
- 239000000203 mixture Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 235000019645 odor Nutrition 0.000 description 6
- 239000002085 irritant Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- 235000011114 ammonium hydroxide Nutrition 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 231100000021 irritant Toxicity 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- UPDATVKGFTVGQJ-UHFFFAOYSA-N sodium;azane Chemical compound N.[Na+] UPDATVKGFTVGQJ-UHFFFAOYSA-N 0.000 description 2
- 239000008399 tap water Substances 0.000 description 2
- 235000020679 tap water Nutrition 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 229940031098 ethanolamine Drugs 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000003700 hair damage Effects 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000003605 opacifier Substances 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000003009 skin protective agent Substances 0.000 description 1
- XUXNAKZDHHEHPC-UHFFFAOYSA-M sodium bromate Chemical compound [Na+].[O-]Br(=O)=O XUXNAKZDHHEHPC-UHFFFAOYSA-M 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- 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
-
- 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
Definitions
- the present ihvention relates to a process for the permanent waving of human hair.
- Hair Waving compositions find extensive use commercially.
- the choice of hair waving compositions is necessarily limited based on the efficacy of the hair waving composition evaluated against the toxicity, odor and skin irritant qualities thereof. While a great many compositions have varying eflicacy in the waving of human hair, the choice of commercial compositions is severely limited because of the frequent high toxicity, objectionable odor, and skin irritant qualities of the hair waving composition.
- useful hair Waving compositions frequently have other adverse side effects, such as hair damage or hair splitting.
- any hair waving solution be highly effective in the waving of human hair and also be relatively nontoxic and safe for home consumption, especially in view of the lack of effective control available in the home use of the solution. In addition, it is highly desirable that it be free from objectionable odor.
- the process of the present invention comprises contacting human hair with an aqueous solution containing from 1 to 10 and preferably from 1 to percent by weight of 2,5- dimercaptothiodiazoline.
- the hair is treated with a solution having a pH of from 8, to 9.5 prior to the waving solution treatment.
- the hair Waving solution of the present invention comprises an aqueous solution containing from 1 to and preferably from 1 to 5 percent by weight of 2,5-dimercaptothiodiazoline.
- the process of the present invention comprises contacting human hair with an aqueous solution as aforesaid.
- the solution may contain from 1 to 10 and preferably from 1 to 5 percent by weight of 2,5-dimercaptothiodiazoline.
- other additives may be employed in the solution to effect particular results provided they do not destroy the basically aqueous nature of the contacting solution, the critical aspect of the present invention being the provision of the requisite quantity of the hair waving component, 2,S-dimercaptothiodiazoline.
- Exemplificative ad ditional ingredients which may be used to modify the aqueous solution include, but are not limited, to the following: alcohols; opacifiers; conditioners; perfumes, and dyes.
- the present invention preferably utilizes 2,S-dimercaptothiodiazoline as the sole active ingredient
- the human hair may be immersed or contacted with or sprayed with the hair waving solution for any desired period of time. Naturally, it is desirable to effect the desired hair waving in as short a period as possible. It is a particular advantage of the present invention that significant hair waving results are obtained with relatively short contact times, i.e., the process of the present invention efficiently obtains a high degree of curl in as little as one minute contact time and preferably in less than thirty minutes. Extended contact times may be utilized, if desired, but no particular advantage is thereby effected.
- the hair is treated with an aqueous solution having a pH of from 8 to 9.5 prior to the waving solution treatment because hair is most susceptible to treatment under mildly basic conditions.
- Any suitable solution having the requisite pH and compatible with the present treatment may be conveniently employed, preferably mild bases, such as ethanol amine, propanol amine and sodium ammonium, i.e., a solution of sodium hydroxide and ammonium hydroxide, e.g., 10 parts ammonium hydroxide and 1 part sodium hydroxide.
- the hair may be efffectively rinsed under cold Water and neutralized in the commercial manner and re-Washed.
- the initial rinsing under cold water is effective in removing remnants of the hair waving solution.
- the commercial neutralizer and re- Wash are standard operations and serve to neutralize and remove excess waving solution and permanently set the hair.
- Representative neutralizers include aqueous solutions containing from 1 to 10 percent by weight of alkali metal brornates or perborates, optimally containing phosphates as stabilizers.
- the treatments thereof may be effected and a high degree of curl obtained with (relative safety to the user with respect to skin-irritant qualities and toxicity; for example, German Patent 959,402 uses the di-sodium salt in skin protective agents against light.
- This is highly significant in view of the critical requirement for these properties in any commercial application of the hair waving solution.
- the hair waving solution of the present invention is free from objectionable odors.
- EXAMPLE 1 The test procedures utilized were to prepare the hair waving solution and immerse the test hairs in the waving solution for 15 minutes.
- the test hairs were ten human hairs cemented together at the root and then wrapped around a 7 diameter glass rod. The ends of the bundlewere taped to the rod. After the hairs were immersed in the waving solution, they were removed and rinsed under cold tap water. They were then neutralized in a 5 percent sodium bromate solution for 10 minutes, washed again in cold tap water and removed from the rod to a piece of filter paper.
- the diameter of the curl was then measured.
- the hair was then re-wet with water and the diameter of the curl measured again.
- the tightness of the initial curl and resistance to uncurling after wetting are measures of the efiicacy of the treatment.
- EXAMPLE 2 The following table shows the results of the tests in Example 1, utilizing a variety of test treatments. The following table shows the results obtained with a waving solutions show little or no hair waving ability. This is especially surprising, since it would normally be expected that suohrelatcdmaterials would also be efiicacious in this respect.
- the compound of the present invention did not have an ob ectionable odor and no hair splitting was observed.
- a process for waving human hair which comprises: contacting human hair with an aqueous solution containing from 1 to 10 percent by weight of 2,5-dimercaptothiodiazoline.
- a process for waving human hair which comprises: contacting said hair with a solution having a pH of from 8 to 9.5 and subsequently contacting said hair with an aqueous solution containing from 1 to 10 percent by weight of 2,5-dimercaptothiodiazoline.
- a process according to claim 2 wherein said solution having a pH of from 8 to 9.5 is selected ijrom the group consisting of ethanol'amine, propanol amine, and sodium ammonium.
- a process for waving human hair which comprises: contacting said hair with an aqueous solution having a pH of from 8 to 9.5, subsequently contacting said hair with References Cited by the Examiner FOREIGN PATENTS 3/57 Germany.
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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)
- Cosmetics (AREA)
Description
United States Patent 3,173,842 PROCESS FQR WAVING HUMAN HAIR WITH 2,5-DIMERCAPTOTHIODIAZOLINE Laurence R. B. Hervey, West Concord, William S. Emerson, Lexington, and Anna Marie Thron, (Iambridge,
Mass., assignors, by mesne assignments, to Olin Mathieson Chemical Corporation, New York, N.Y., a
corporation of Virginia No Drawing. Filed Sept. 3, 1963, Ser. No. 306,303
6 Claims. (Cl. 167-871) The present ihvention relates to a process for the permanent waving of human hair.
Hair Waving compositions find extensive use commercially. The choice of hair waving compositions is necessarily limited based on the efficacy of the hair waving composition evaluated against the toxicity, odor and skin irritant qualities thereof. While a great many compositions have varying eflicacy in the waving of human hair, the choice of commercial compositions is severely limited because of the frequent high toxicity, objectionable odor, and skin irritant qualities of the hair waving composition. In addition, useful hair Waving compositions frequently have other adverse side effects, such as hair damage or hair splitting.
It is essential that any hair waving solution be highly effective in the waving of human hair and also be relatively nontoxic and safe for home consumption, especially in view of the lack of effective control available in the home use of the solution. In addition, it is highly desirable that it be free from objectionable odor.
Accordingly, it is an object of the present invention to provide a novel process for the permanent waving of human hair.
It is a still further object of the present invention to provide a process, as aforesaid, which is highly effective in the waving of human hair and also which utilizes materials which are relatively non-toxic, free from objectionable odor, and relatively negative as a skin irritant.
It is an additional object of the present invention to provide a process as aforesaid, which is safe and effective and commercially competitive.
Further objects and advantages of the present invention will appear hereinafter.
In accordance with the present invention, it has now been found that the foregoing objects and advantages of the present invention may be readily accomplished. The process of the present invention comprises contacting human hair with an aqueous solution containing from 1 to 10 and preferably from 1 to percent by weight of 2,5- dimercaptothiodiazoline. In the prefer-red embodiment the hair is treated with a solution having a pH of from 8, to 9.5 prior to the waving solution treatment.
The hair Waving solution of the present invention comprises an aqueous solution containing from 1 to and preferably from 1 to 5 percent by weight of 2,5-dimercaptothiodiazoline.
The process of the present invention comprises contacting human hair with an aqueous solution as aforesaid. The solution may contain from 1 to 10 and preferably from 1 to 5 percent by weight of 2,5-dimercaptothiodiazoline. In addition, other additives may be employed in the solution to effect particular results provided they do not destroy the basically aqueous nature of the contacting solution, the critical aspect of the present invention being the provision of the requisite quantity of the hair waving component, 2,S-dimercaptothiodiazoline. Exemplificative ad ditional ingredients which may be used to modify the aqueous solution include, but are not limited, to the following: alcohols; opacifiers; conditioners; perfumes, and dyes.
It is noted that the present invention preferably utilizes 2,S-dimercaptothiodiazoline as the sole active ingredient;
but the present invention encompasses within its scope utilizing other conventional active ingredients in combination with 2,5-dimercaptothiodiazoline.
The human hair may be immersed or contacted with or sprayed with the hair waving solution for any desired period of time. Naturally, it is desirable to effect the desired hair waving in as short a period as possible. It is a particular advantage of the present invention that significant hair waving results are obtained with relatively short contact times, i.e., the process of the present invention efficiently obtains a high degree of curl in as little as one minute contact time and preferably in less than thirty minutes. Extended contact times may be utilized, if desired, but no particular advantage is thereby effected.
In the preferred embodiment, the hair is treated with an aqueous solution having a pH of from 8 to 9.5 prior to the waving solution treatment because hair is most susceptible to treatment under mildly basic conditions. Any suitable solution having the requisite pH and compatible with the present treatment may be conveniently employed, preferably mild bases, such as ethanol amine, propanol amine and sodium ammonium, i.e., a solution of sodium hydroxide and ammonium hydroxide, e.g., 10 parts ammonium hydroxide and 1 part sodium hydroxide.
After the hair waving treatment, the hair may be efffectively rinsed under cold Water and neutralized in the commercial manner and re-Washed. The initial rinsing under cold water is effective in removing remnants of the hair waving solution. The commercial neutralizer and re- Wash are standard operations and serve to neutralize and remove excess waving solution and permanently set the hair. Representative neutralizers include aqueous solutions containing from 1 to 10 percent by weight of alkali metal brornates or perborates, optimally containing phosphates as stabilizers.
It is a significant aspect of the present invention that the treatments thereof may be effected and a high degree of curl obtained with (relative safety to the user with respect to skin-irritant qualities and toxicity; for example, German Patent 959,402 uses the di-sodium salt in skin protective agents against light. This is highly significant in view of the critical requirement for these properties in any commercial application of the hair waving solution. In addition, and especially important in commercial use, the hair waving solution of the present invention is free from objectionable odors.
The present invention will be more readily apparent from a consideration of the following illustrative examples:
EXAMPLE 1 The test procedures utilized were to prepare the hair waving solution and immerse the test hairs in the waving solution for 15 minutes. The test hairs were ten human hairs cemented together at the root and then wrapped around a 7 diameter glass rod. The ends of the bundlewere taped to the rod. After the hairs were immersed in the waving solution, they were removed and rinsed under cold tap water. They were then neutralized in a 5 percent sodium bromate solution for 10 minutes, washed again in cold tap water and removed from the rod to a piece of filter paper.
The diameter of the curl was then measured.
The hair was then re-wet with water and the diameter of the curl measured again.
The tightness of the initial curl and resistance to uncurling after wetting are measures of the efiicacy of the treatment.
EXAMPLE 2 The following table shows the results of the tests in Example 1, utilizing a variety of test treatments. The following table shows the results obtained with a waving solutions show little or no hair waving ability. This is especially surprising, since it would normally be expected that suohrelatcdmaterials would also be efiicacious in this respect.
The compound of the present invention did not have an ob ectionable odor and no hair splitting was observed.
Table 1 Our] Diameter pH of V Waving Treatment Waving After Solution Initial Rcwet- (in.) ting (in.)
Water 7 1%; 2,5-D imercaptothiodiazoline 1 ,1 1 A 2,5-Dimercaptothiodiazoline, add
NH4OE 8. 5 1 1 Methyl dithioearbazinate 5 1%; 1% Methyl dithiocarbazinate, add NHiOH. 8. 5 1%; 1th 3,5-Dithiol-4-amino-1,2,5-triaz0le, solubilized with NHAOH 9. 2 134 1%; 3-Thio1-5-amino-1,2,4-triazole add NH4OH 8. 7 "A6 1%; 2-An1ino-5-thiol-1,3,4-thiadiazole, add I NHJOH 8. 9 %5 l 2,5-Dirnercaptothiodiazoline, hair soaked in a solution of pH 8.5 before waving solution treatment 1 1 V 6 or essential characteristics thereof. The presentembodij ment is therefore to be considered as in all respects illustrative and not restrictive, the scope of the invention being indicated by the appended claims, and all changes which come within the meaning and range of equivalency are intended to be embraced therein.
What is claimed is:
1. A process for waving human hair which comprises: contacting human hair with an aqueous solution containing from 1 to 10 percent by weight of 2,5-dimercaptothiodiazoline.
2. A process for waving human hair which comprises: contacting said hair with a solution having a pH of from 8 to 9.5 and subsequently contacting said hair with an aqueous solution containing from 1 to 10 percent by weight of 2,5-dimercaptothiodiazoline.
3. A process according to claim 2 wherein said solution having a pH of from 8 to 9.5 is selected ijrom the group consisting of ethanol'amine, propanol amine, and sodium ammonium.
4. A process according to claim 1 wherein said solution contains from 1 to 5 percent by weight of 2,5-dimercaptothiodiazoline.
5. A process according to claim 1 wherein said hair is contacted with said solution for from 1 to 30 minutes.
6. A process for waving human hair which comprises: contacting said hair with an aqueous solution having a pH of from 8 to 9.5, subsequently contacting said hair with References Cited by the Examiner FOREIGN PATENTS 3/57 Germany.
LEWIS GOTTS, Primary Examiner.
JULIAN S. LEVITT, Examiner.
Claims (1)
1. A PROCESS FOR WAVING HUMAN HAIR WHICH COMPRISES: CONTACTING HUMAN HAIR WITH AN AQUEOUS SOLUTION CONTAINING FROM 1 TO 10 PERCENT BY WEIGHT OF 2,5-DIMERCAPTOTHIODIAZOLINE.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US306308A US3173842A (en) | 1963-09-03 | 1963-09-03 | Process for waving human hair with 2, 5-dimercaptothiodiazoline |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US306308A US3173842A (en) | 1963-09-03 | 1963-09-03 | Process for waving human hair with 2, 5-dimercaptothiodiazoline |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3173842A true US3173842A (en) | 1965-03-16 |
Family
ID=23184724
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US306308A Expired - Lifetime US3173842A (en) | 1963-09-03 | 1963-09-03 | Process for waving human hair with 2, 5-dimercaptothiodiazoline |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US3173842A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4296764A (en) * | 1979-12-26 | 1981-10-27 | Chesebrough-Pond's Inc. | Hair waving and straightening method |
| US4630621A (en) * | 1985-09-27 | 1986-12-23 | Susanne Pontani | Method and composition for simultaneously permanently waving and dyeing human hair |
| US5161553A (en) * | 1986-09-19 | 1992-11-10 | Clairol Incorporated | Process for simultaneously waving and coloring hair |
| FR2854568A1 (en) * | 2003-05-06 | 2004-11-12 | Oreal | USE OF DITHIOLS IN A PERMANENT HAIR DEFORMATION COMPOSITION |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE959402C (en) * | 1953-03-13 | 1957-03-07 | Basf Ag | Light stabilizers |
-
1963
- 1963-09-03 US US306308A patent/US3173842A/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE959402C (en) * | 1953-03-13 | 1957-03-07 | Basf Ag | Light stabilizers |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4296764A (en) * | 1979-12-26 | 1981-10-27 | Chesebrough-Pond's Inc. | Hair waving and straightening method |
| US4630621A (en) * | 1985-09-27 | 1986-12-23 | Susanne Pontani | Method and composition for simultaneously permanently waving and dyeing human hair |
| US5161553A (en) * | 1986-09-19 | 1992-11-10 | Clairol Incorporated | Process for simultaneously waving and coloring hair |
| FR2854568A1 (en) * | 2003-05-06 | 2004-11-12 | Oreal | USE OF DITHIOLS IN A PERMANENT HAIR DEFORMATION COMPOSITION |
| WO2004098488A3 (en) * | 2003-05-06 | 2004-12-29 | Oreal | Use of dithiols in a hair-perming composition |
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