US3534135A - Method for setting hair with dithiourea and derivatives thereof - Google Patents
Method for setting hair with dithiourea and derivatives thereof Download PDFInfo
- Publication number
- US3534135A US3534135A US603398A US3534135DA US3534135A US 3534135 A US3534135 A US 3534135A US 603398 A US603398 A US 603398A US 3534135D A US3534135D A US 3534135DA US 3534135 A US3534135 A US 3534135A
- Authority
- US
- United States
- Prior art keywords
- hair
- dithiourea
- solution
- setting
- derivatives
- 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
- 238000000034 method Methods 0.000 title description 13
- KCOYHFNCTWXETP-UHFFFAOYSA-N (carbamothioylamino)thiourea Chemical compound NC(=S)NNC(N)=S KCOYHFNCTWXETP-UHFFFAOYSA-N 0.000 title description 7
- 150000003839 salts Chemical class 0.000 description 22
- 239000000243 solution Substances 0.000 description 18
- 239000000203 mixture Substances 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 8
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical class NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 8
- 102000011782 Keratins Human genes 0.000 description 7
- 108010076876 Keratins Proteins 0.000 description 7
- 102000004169 proteins and genes Human genes 0.000 description 7
- 108090000623 proteins and genes Proteins 0.000 description 7
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 239000008365 aqueous carrier Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 150000001649 bromium compounds Chemical class 0.000 description 3
- 239000012876 carrier material Substances 0.000 description 3
- 150000003841 chloride salts Chemical class 0.000 description 3
- 150000002823 nitrates Chemical class 0.000 description 3
- 150000003891 oxalate salts Chemical class 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000003929 acidic solution Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 230000003806 hair structure Effects 0.000 description 2
- PSFDQSOCUJVVGF-UHFFFAOYSA-N harman Chemical compound C12=CC=CC=C2NC2=C1C=CN=C2C PSFDQSOCUJVVGF-UHFFFAOYSA-N 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000002304 perfume Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000012047 saturated solution Substances 0.000 description 2
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 2
- 230000002269 spontaneous effect Effects 0.000 description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 description 2
- HGPNKTHAVDVUNT-UHFFFAOYSA-N 2-dodecylpyridine;hydrochloride Chemical compound [Cl-].CCCCCCCCCCCCC1=CC=CC=[NH+]1 HGPNKTHAVDVUNT-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- -1 alkali metal bromates Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- SXDBWCPKPHAZSM-UHFFFAOYSA-M bromate Chemical class [O-]Br(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-M 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- QBWCMBCROVPCKQ-UHFFFAOYSA-N chlorous acid Chemical class OCl=O QBWCMBCROVPCKQ-UHFFFAOYSA-N 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000000249 desinfective effect Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 210000004761 scalp Anatomy 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- AQLJVWUFPCUVLO-UHFFFAOYSA-N urea hydrogen peroxide Chemical compound OO.NC(N)=O AQLJVWUFPCUVLO-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 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
- 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
- A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
Definitions
- the present invention relates to setting or fixing hair, more particulraly to setting hair which, in softened condition has been subjected to permanent waving.
- a hair setting composition and a method of setting hair are provided which will restore the disulfide bridges between protein chains of the keratin of the hair which were split by means of reducing agents such as thioglycolates in order to make the hair sufficiently deformable for the permanent waving of the same.
- reducing agents such as thioglycolates
- bifunctional compounds were suggested as fixing agents, which by reaction of their functional groups with the SH groups of adjacent protein chains are capable to form a molecular bridge, and thereby permanently set the hair in the shape given to the same.
- these compounds, including the bridges between the protein chains are different from the compounds present in the natural hair structure and, furthermore, cause irreversible and disadvantageous changes in the structure of the hair.
- Suitable for this purpose are several oxidizing agents and, in fact, for the setting of permanent waves, hydrogen peroxide and addition products thereof such as urea peroxide and alkali perborates as well as salts of oxygencontaining hydrohalic acids such as alkali metal bromates and chlorites have been used.
- alkali metal polythionates were proposed for the fixing of permanent waves, because these last-mentioned compounds, due to their very mild oxidizing effect, would not cause any damage to the hair.
- the last-mentioned compounds are incapable of achieving the desired degree of fixing of the hair so that permanently waved hair treated in this manner will not be sufficiently resistant against humidity or moisture and under such conditions will lose its shape. It appears that the effect of the polythionates is too weak to cause the conversion of a sufficiently large proportion of the SH groups of the softened hair into cross-lined SS bridges.
- the softened permanently waved hair is effectively set without forming in the hair structure any compounds which are foreign to natural hair, by applying to the softened hair a hair setting composition which consists essentially of a carrier material which is compatible with hair and in which is distributed a salt of dithiourea (diformamidine disulfide) or of an N-alkyl derivative of dithiourea.
- a hair setting composition which consists essentially of a carrier material which is compatible with hair and in which is distributed a salt of dithiourea (diformamidine disulfide) or of an N-alkyl derivative of dithiourea.
- the above described effective salt is dissolved in an aqueous liquid as the carrier material and the N-alkyl derivative preferably is a N-lower alkyl derivative.
- the effective proportion of the above described salts generally will be between about 2% by weight of the hair setting composition and a maximum percentage which equals the concentration of a saturated solution of the salt in the aqueous liquid.
- hair setting composition as described above will cause substantial restoration of the initial disulfide bridges between the protein chains of the hair keratin which were split in order to soften the hair so as to make it amenable to waving or other deformation.
- hair deformation is referred to herein generally as hair waving
- the present invention is not limited to the setting or fixing of permanently waved hair but can also be utilized in connection with the setting or fixing of, for instance, straightened hair, or hair which for whatever reason had been softened under splitting of the above described disulfide bridges.
- one or more salts of dithiourea or of N-alkyl derivatives thereof are used for the fixing or setting of the softened, for instance permanently waved, hair.
- the salts of the N-alkyl derivatives which may be used in accordance with the present invention are preferably N-lower-alkyl derivatives, since higher alkyl derivatives of this kind are of markedly reduced effectiveness.
- the type of the anion of these salts is substantially without significance.
- the chlorides or bromides are used but good results are also obtained by utilizing other organic or inorganic salts of thiourea or of N-loWeralkyl derivatives thereof, for instance, nitrates or oxalates.
- the salts which form the effective setting agent of the present invention have the following structural formula:
- R denotes either hydrogen or an alkyl group, and the alkyl group preferably is methyl, ethyl or propyl. It will be noted that the structural formula includes four secondary valences C N.
- the salts of dithiourea and derivatives thereof which are used according to the present invention are stable in solid condition and are also harmless when stored and used in solution since they tend neither to spontaneous decomposition nor is there any danger of inflammation.
- the salts are used in an acidic aqueous solution since these salts have their best fixing effect in an acidic medium and, on the other hand, when applied in an acidic solution, the alkaline permanent waving solution will be quickly neutralized so that the conventional acidic rinse can be dispensed with.
- dithiourea compounds which are utilized according to the present invention tend in weak acidic solutions slowly to split off colloidal sulfur. This phenomenon also takes place during contact of the hair setting composition of the present invention on the hair with alkaline hair waving solution. It is well known that elementary sulfur has a disinfecting and generally favorable effect on the scalp so that the slow formation of colloidal sulfur represents another favorable side effect of the present invention.
- the effective salts which are utilized according to the present invention may be combined with suitable, preferable aqueous carrier substances which are compatible with hair, as well as with other preparations and additives of hair cosmetic preparations, such as emulsifiers, wetting agents, thickeners and the like.
- the concentration of the salts of thiourea and/or the above described derivatives thereof in the hair setting composition according to the present invention generally will be at least equal to 2% of the weight of the hair setting composition and preferably equal to between about 5% and of the weight thereof.
- the upper limit of the 4 concentration will be that of a saturated solution of the effective salt in the carrier liquid.
- EXAMPLE I 8.0 g. dithiourea-dichloride and 0.8 g. sodiumlaurylsulfate (Texapon Z highly concentrated) are dissolved in ml. water, and the pH of the solution is 1.8.
- One-half of the thus obtained solution is foamed onto the hair while the same is wound on curlers or rollers and allowed to react with the hair for about 3 minutes. Thereafter, the curlers or rollers are removed and the other half of the solution is foamed onto the hair and again allowed to react for 3 minutes. This is followed by rinsing, and thereby the hair setting is completed.
- EXAMPLE II 12.0 g. dithiourea-dibromide and 1.0 g. laurylpyridinechloride are dissolved in ml. water, and the pH of the solution is 2.0.
- the hair treatment is carried out as described in Example I.
- EXAMPLE III 12.0 g. dithiourea-dichloride, 2.0 g. thiourea and 3.0 g. dry perfume (polyglycol 10,000 with 15% perfume oil) are dissolved in 100 ml. water, and the pH of the solution is 1.8.
- One-half of the solution is applied to the hair while the same is wound on curlers and allowed to react for 3 minutes. Thereafter, the curlers are removed and the other half of the solution is applied to the hair and again allowed to react for 3 minutes, followed by rinsing with water.
- EXAMPLE IV 30.9 g. dithiourea-dichloride and 22.0 g. disodiumhydrogenphosphate- 12 H O are dissolved in 500 ml. water, to form a solution having a pH of 4.0.
- EXAMPLE V 20.0 g. N,N-diisopropyl-dithiourea-dibromide are dissolved in 500 ml. water, to form a solution having a pH of 2.2.
- the hair is treated with the thus formed solution as described in Example IV.
- EXAMPLE VI 10.0 g. N,N-diethyl-dithiourea-dibromide are dissolved in 100 ml. water, to form a solution having a pH of 2.2.
- the hair is then set as described in Example III.
- EXAMPLE VII 8.0 g. N,N-dimethyl-dithiourea-dibromide and 0.6 g. sodiumlaurylsulfate (Texapon Z, highly concentrated) are dissolved in 60 ml. water, to form a solution having a pH of 1.9.
- the hair is treated with the thus formed solution, as described in Example I.
- Method for setting hair which has been softened by splitting disulfide bridges between protein chains of the hair keratin, comprising the steps of applying to said thus softened hair a hair setting composition consisting essentially of an aqueous carrier which is compatible with hair and having distributed therethrough an effective amount of a substance selected from the group consisting of a water-soluble salt of diformamidine disulfide and N-lower alkyl derivatives thereof.
- a method as defined in claim 1, wherein said salt is selected from the group consisting of chlorides, bromides, nitrates and oxalates.
- said efi ective amount is equal to between about 2% by weight of said hair setting composition and the saturation concentration of said substance in said aqueous carrier.
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEW0040583 | 1965-12-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3534135A true US3534135A (en) | 1970-10-13 |
Family
ID=7602524
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US603398A Expired - Lifetime US3534135A (en) | 1965-12-23 | 1966-12-20 | Method for setting hair with dithiourea and derivatives thereof |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US3534135A (enrdf_load_stackoverflow) |
| BE (1) | BE686608A (enrdf_load_stackoverflow) |
| DE (1) | DE1492257A1 (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3642429A (en) * | 1967-10-26 | 1972-02-15 | Oreal | Cosmetic composition for treating hair |
| US3862221A (en) * | 1967-08-02 | 1975-01-21 | Oreal | N,N{40 -di(hydroxymethylcarbamyl)cystamine |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2195623A (en) * | 1937-09-01 | 1940-04-02 | Monsanto Chemicals | Sponge rubber |
| US2783272A (en) * | 1956-05-08 | 1957-02-26 | Du Pont | Production of formamidine sulfinic acid |
| US2853132A (en) * | 1955-06-17 | 1958-09-23 | Ciba Ltd | Pest combating composition and methods employing diformamidine sulfides |
-
1965
- 1965-12-23 DE DE19651492257 patent/DE1492257A1/de active Pending
-
1966
- 1966-09-08 BE BE686608D patent/BE686608A/xx unknown
- 1966-12-20 US US603398A patent/US3534135A/en not_active Expired - Lifetime
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2195623A (en) * | 1937-09-01 | 1940-04-02 | Monsanto Chemicals | Sponge rubber |
| US2853132A (en) * | 1955-06-17 | 1958-09-23 | Ciba Ltd | Pest combating composition and methods employing diformamidine sulfides |
| US2783272A (en) * | 1956-05-08 | 1957-02-26 | Du Pont | Production of formamidine sulfinic acid |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3862221A (en) * | 1967-08-02 | 1975-01-21 | Oreal | N,N{40 -di(hydroxymethylcarbamyl)cystamine |
| US3642429A (en) * | 1967-10-26 | 1972-02-15 | Oreal | Cosmetic composition for treating hair |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1492257A1 (de) | 1969-11-06 |
| BE686608A (enrdf_load_stackoverflow) | 1967-02-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5332570A (en) | Reducing solution for permanent wave | |
| US3892845A (en) | Hair shade adjuster | |
| US3654936A (en) | Process for straightening human hair | |
| US3910289A (en) | Permanent wave composition for hair and process of using it | |
| US4834971A (en) | Hair permanent-waving method and aftertreatment composition | |
| US4812307A (en) | Crosslinking of hair thiols using glutathione disulfide | |
| US4859459A (en) | Method of shaping human hair using dipropylene glycol monomethyl ether | |
| US3840656A (en) | Process for improving the durability and quality of a hair set and new products for carrying out this process | |
| JPS6220169B2 (enrdf_load_stackoverflow) | ||
| KR860006258A (ko) | 퍼머넨트 웨이브 중화제 조성물 및 퍼머넨트 웨이브 형성방법 | |
| US4666712A (en) | Cold permanent wave composition | |
| EP0313561B1 (en) | Compositions used in permanent structure altering of hair | |
| JPS629566B2 (enrdf_load_stackoverflow) | ||
| US2869559A (en) | Non-volatile mercaptan and hydroxyamine impregnated end wrap and method of use | |
| US3847165A (en) | Acidic permanent waving solution and process for its use | |
| US2817342A (en) | Method of permanently reshaping a keratin-containing substance | |
| US4038995A (en) | Hair treating composition containing a mink oil fatty acid quaternary ammonium salt | |
| GB2027080A (en) | Permanent hair waving method | |
| US3534135A (en) | Method for setting hair with dithiourea and derivatives thereof | |
| US3880174A (en) | Permanent hair shaping composition and method for using the same | |
| US2564722A (en) | Process for treating hair to impart a permanent set thereto | |
| EP0356508A1 (en) | Permanent wave process and compositions | |
| JPH072634A (ja) | 毛髪のパーマネント加工剤および加工方法 | |
| US3582259A (en) | Method of treating hair to improve quality and "hold" of "sets" imparted thereto | |
| US3459198A (en) | Waving and straightening human hair with 1,4-dimercapto-2,3-butane diol and substituted products thereof |