US2975101A - Dyeing of hair and other keratinous materials - Google Patents
Dyeing of hair and other keratinous materials Download PDFInfo
- Publication number
- US2975101A US2975101A US709479A US70947958A US2975101A US 2975101 A US2975101 A US 2975101A US 709479 A US709479 A US 709479A US 70947958 A US70947958 A US 70947958A US 2975101 A US2975101 A US 2975101A
- Authority
- US
- United States
- Prior art keywords
- hair
- solution
- dyeing
- triphenol
- employed
- 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
- 238000004043 dyeing Methods 0.000 title claims description 18
- 210000004209 hair Anatomy 0.000 title description 37
- 239000000463 material Substances 0.000 title description 9
- 238000000034 method Methods 0.000 claims description 18
- CQOZJDNCADWEKH-UHFFFAOYSA-N 2-[3,3-bis(2-hydroxyphenyl)propyl]phenol Chemical compound OC1=CC=CC=C1CCC(C=1C(=CC=CC=1)O)C1=CC=CC=C1O CQOZJDNCADWEKH-UHFFFAOYSA-N 0.000 claims description 13
- 239000007864 aqueous solution Substances 0.000 claims description 8
- 239000000243 solution Substances 0.000 description 31
- 239000007800 oxidant agent Substances 0.000 description 19
- GGNQRNBDZQJCCN-UHFFFAOYSA-N benzene-1,2,4-triol Chemical compound OC1=CC=C(O)C(O)=C1 GGNQRNBDZQJCCN-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000000376 reactant Substances 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 238000011282 treatment Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241001070941 Castanea Species 0.000 description 3
- 235000014036 Castanea Nutrition 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000001476 alcoholic effect Effects 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 238000005470 impregnation Methods 0.000 description 3
- 150000007522 mineralic acids Chemical class 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 3
- MLIWQXBKMZNZNF-KUHOPJCQSA-N (2e)-2,6-bis[(4-azidophenyl)methylidene]-4-methylcyclohexan-1-one Chemical compound O=C1\C(=C\C=2C=CC(=CC=2)N=[N+]=[N-])CC(C)CC1=CC1=CC=C(N=[N+]=[N-])C=C1 MLIWQXBKMZNZNF-KUHOPJCQSA-N 0.000 description 2
- QKGQHTCUNGPCIA-UHFFFAOYSA-N 2,4,5-Trihydroxytoluene Chemical compound CC1=CC(O)=C(O)C=C1O QKGQHTCUNGPCIA-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- ZRDJERPXCFOFCP-UHFFFAOYSA-N azane;iodic acid Chemical class [NH4+].[O-]I(=O)=O ZRDJERPXCFOFCP-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
- ICIWUVCWSCSTAQ-UHFFFAOYSA-M iodate Chemical compound [O-]I(=O)=O ICIWUVCWSCSTAQ-UHFFFAOYSA-M 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- FOHHNHSLJDZUGQ-UHFFFAOYSA-N 3-(dibutylamino)-1-[1,3-dichloro-6-(trifluoromethyl)-9-phenanthrenyl]-1-propanol Chemical compound FC(F)(F)C1=CC=C2C(C(O)CCN(CCCC)CCCC)=CC3=C(Cl)C=C(Cl)C=C3C2=C1 FOHHNHSLJDZUGQ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241000158728 Meliaceae Species 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002085 enols Chemical class 0.000 description 1
- 150000002193 fatty amides Chemical class 0.000 description 1
- 210000003746 feather Anatomy 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 229960003242 halofantrine Drugs 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- -1 hydrogen salt Chemical class 0.000 description 1
- 159000000014 iron salts Chemical class 0.000 description 1
- 235000015110 jellies Nutrition 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- NALMPLUMOWIVJC-UHFFFAOYSA-N n,n,4-trimethylbenzeneamine oxide Chemical compound CC1=CC=C([N+](C)(C)[O-])C=C1 NALMPLUMOWIVJC-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- CCDXIADKBDSBJU-UHFFFAOYSA-N phenylmethanetriol Chemical compound OC(O)(O)C1=CC=CC=C1 CCDXIADKBDSBJU-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- HELHAJAZNSDZJO-OLXYHTOASA-L sodium L-tartrate Chemical compound [Na+].[Na+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O HELHAJAZNSDZJO-OLXYHTOASA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011697 sodium iodate Substances 0.000 description 1
- 229940032753 sodium iodate Drugs 0.000 description 1
- 235000015281 sodium iodate Nutrition 0.000 description 1
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 1
- 239000001433 sodium tartrate Substances 0.000 description 1
- 229960002167 sodium tartrate Drugs 0.000 description 1
- 235000011004 sodium tartrates Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
-
- 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
- A61K8/34—Alcohols
- A61K8/347—Phenols
-
- 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
- A61Q5/10—Preparations for permanently dyeing the hair
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/02—Material containing basic nitrogen
- D06P3/04—Material containing basic nitrogen containing amide groups
- D06P3/30—Material containing basic nitrogen containing amide groups furs feathers, dead hair, furskins, pelts
- D06P3/305—Material containing basic nitrogen containing amide groups furs feathers, dead hair, furskins, pelts with oxidation dyes
Definitions
- This invention relates to the dyeing of hair, including human hair, and other keratinous materials.
- 2,4,5-trihydroxytoluene is capable of dyeing, wool in shades from light reddish-brown to dark brown, depending upon whether the solution is adjusted to an acid or an alkaline pH-value, by operating at 90 "C. for l hour.
- a process for dyeing hair is also known, in which use is made of the 1,2,4-trihydroxy compounds of benzene (which may also contain other s'ubstituents) in the form of their corresponding'1,2,4- triacyl derivatives; such derivatives are saponified a few moments before their application by boiling them in aqueous alcoholic solution in the presence of an excess of an alkaline reactant, such as sodium carbonate.
- thesesaponified derivatives are applied in alkaline medium; whatever the method of oxidation employed (simsirable because of the subsequent chemical treatments.
- a process for dyeing hair and other keratinous material comprises subjectingthe same to the simultaneous action of at least one triphenol of the following general formula:
- Rj represents a hydrogen orhalo gen atom'or an ing and drying the hair or other material.
- the global triphenol concentration of the solution applied to the hair ,or other keratinous material may vary within fairly widelirnits but is preferably between 0.01
- the pH-value of the solutions may vary between 1 V lathe-case where the solution employed contains one of thev aforesaid oxidising agents, account should be taken, in selecting the working pH, of the nature of this oxidising agent.
- an alkali metal or ammo-i 5 nium iodate onperiodate. is employed asthe oxidising reactant, it is preferable not to reduce the pH below 3 alcoholic solutions of 1,2,4-trihydroxybenzene or of'2,4,5-
- trihydroxytoluene which may advantageously be adjusted to an acid pH for application to the hair, the shade being thereafter developed on ⁇ the hair itself by the addition of analiphatic'o'r araliphatic primary amineor again, if-
- u aqueous or aqueous ⁇ alcoholic solution of thetriphenol or of the mixture of triphenols is' prepared, to which theiinorganicoxidiz-Q ,iug agent or agents is or are added at the time of apple The cation to. the hair or other keratinous product.
- pH of the solution may beadjus te'dto the desired value
- the use'of metallic salts does .in I V and the oxidizing agent
- the pH theriresulting simply by the addition of any appropriate reactant. If preferred it is Iev'en'possible to usejthe solution as such that is to 1 1T sa'y,withoutanyothercOnstituent than the'triphenols p 2915.101 9, w e
- the solution is preferably left in contact with the hair or other keratinous material for 5-60 minutes and the gair is then briefly rinsed, shampooed, rinsed again and ried.
- the inorganic oxidizing agent or agents may be introduced into the triphenol solution either in the form of powder or in aqueous solution.
- the process is carried out in two stages, by first applying the solution of the triphenol or triphenols, free from any oxidizing agent, and allowing this solution to remain in contact with the hair or with the product to be dyed for 5-60 minutes in order to complete the impregnation, partly drying the hair, if desired after rinsing with water, and then applying an aqueous solution of the selected oxidizing agent and leaving it in contact for the period necessary for the development of the shade, generally from 5-20 minutes, the hair then being rinsed, shampooed, rinsed again and dried.
- the pH of the triphenol solution applied in the first stage is not adapted to the nature of the oxidizing agent employed or to the desired effect, or if the brief rinsing which has followed this first application has caused the pH on the hair to revert to a higher excessive value, said value may be modified by adding to the solution containing the oxidizing agent an appropriate reactant, for example an organic or inorganic acid, an acid hydrogen salt or a buffer.
- an appropriate reactant for example an organic or inorganic acid, an acid hydrogen salt or a buffer.
- the oxidising agent employed is an iodate or periodate it is preferable not to reduce the pH value below 3 and to avoid the use of strong inorganic acids for obtaining low pH values.
- the concentration of the oxidizing agent in the solution containing it may be comprised between fairly wide limits, depending upon the desired shade and upon the own solubility of the oxidizing agents which may be employed.
- the quantity of oxidizing agent to be employed corresponds to about 0.5 to g. per 100 cc. of the triphenol solution employed, whether or not this solution itself contains the oxidizing agent.
- the volumes of triphenol solution and/ or of oxidizing agent to be employed are based in each case on the bulk of hair to be treated or on the quantity of other keratinous material to be dyed.
- the dyeing process of the invention may be carried out not only by means of aqueous solutions as described above, but also by means of creams, pastes or jellies, the adjustment to the required consistency being effected by any conventional method used in hair dyeing.
- Example I A solution having the following composition is prepared:
- the pH of this solution is 4.
- 2 g. of potassium periodate are added thereto.
- the solution is left'in contact with the hair for 20 minutes, and the hair is then rinsed, shampooed, rinsed again and dried.
- the shade obtained is light chestnut and has a very natural appearance.
- Example III The following composition is employed:
- Example VI A solution having the following composition is prepared:
- the invention is of especial importance in relation to the dyeing of human hair it may also be applied, for example, to keratinous materials in the form of fibers, felts, furs and feathers.
- a process for dyeing live human hair at room temperature which comprises applying thereto, a freshly prepared aqueous solution containing a triphenol of the general formula HO OH wherein R is selected from the group consisting of by drogen, halogen, alkyl, alkoxy and hydroxyalkyl, said solution being adjusted to a pH value of at most 7 and containing an oxidizing agent selected from the group consisting of alkali metal and ammonium iodates, periodates and persulphates.
- a process for dyeing live human hair at room temperature which comprises applying thereto, a freshly prepared aqueous solution containing a triphenol of the general formula HO OH 3.
- a process for dyeing live human hair at room temperature which comprises applying thereto, a freshly prepared aqueous solution containing -a triphenol of the gen: eral formula HO OH HO R wherein R is selected from the group consisting of hydrogen, halogen, alkyl, alkoxy and hydroxyalkyl, said solution being adjusted to a pH value of at least 3 and at most 7 and containing an oxidizing agent selected from the group consisting of alkali metal and ammonium iodates, periodates and presulphates, said solution containing 0.01 mole to 1 mole of said triphenol per litre and 0.5 to 10 grams of said oxidizing agent per cc.
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Cosmetics (AREA)
- Coloring (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR348511X | 1957-01-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2975101A true US2975101A (en) | 1961-03-14 |
Family
ID=8892640
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US709479A Expired - Lifetime US2975101A (en) | 1957-01-22 | 1958-01-17 | Dyeing of hair and other keratinous materials |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US2975101A (ja) |
| BE (1) | BE564088A (ja) |
| CH (1) | CH348511A (ja) |
| DE (1) | DE1126565B (ja) |
| GB (1) | GB827439A (ja) |
| NL (1) | NL224268A (ja) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3920384A (en) * | 1974-07-17 | 1975-11-18 | Clairol Inc | Autoxidizable hair dye containing preparations |
| JPS5135441A (en) * | 1974-07-17 | 1976-03-25 | Bristol Myers Co | Jidosankaseimohatsusenryoto sonoseiho |
| US4529404A (en) * | 1976-06-30 | 1985-07-16 | Clairol Incorporated | Hair dye preparation |
| 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 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1489344A (en) * | 1974-01-18 | 1977-10-19 | Unilever Ltd | Hair dyeing composition |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1663202A (en) * | 1926-03-29 | 1928-03-20 | Kritchevsky Wolf | Hair dye |
| US2733186A (en) * | 1951-04-19 | 1956-01-31 | Compositions for the dyeing of hair | |
| GB745531A (en) * | 1953-01-01 | 1956-02-29 | Gillette Industries Ltd | Improvements in or relating to the dyeing of hair and other keratinous material |
| GB745532A (en) * | 1953-01-01 | 1956-02-29 | Gillette Industries Ltd | Improvements in or relating to the dyeing of hair and other keratinous material |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE663781C (de) * | 1936-05-08 | 1938-08-13 | I G Farbenindustrie Akt Ges | Haarfaerbemittel |
| AT179384B (de) * | 1951-04-19 | 1954-08-25 | Union Francaise Commerciale Et Industrielle Sa | Verfahren zur Herstellung eines unschädlichen Haarfärbemittels |
| AT188027B (de) * | 1951-11-19 | 1956-12-27 | Union Francaise Commerciale Et Industrielle Sa | Verfahren zur Herstellung eines unschädlichen Haarfärbemittels |
-
0
- NL NL224268D patent/NL224268A/xx unknown
- BE BE564088D patent/BE564088A/xx unknown
-
1958
- 1958-01-17 US US709479A patent/US2975101A/en not_active Expired - Lifetime
- 1958-01-17 GB GB1753/58A patent/GB827439A/en not_active Expired
- 1958-01-20 DE DES56643A patent/DE1126565B/de active Pending
- 1958-01-21 CH CH348511D patent/CH348511A/fr unknown
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1663202A (en) * | 1926-03-29 | 1928-03-20 | Kritchevsky Wolf | Hair dye |
| US2733186A (en) * | 1951-04-19 | 1956-01-31 | Compositions for the dyeing of hair | |
| GB745531A (en) * | 1953-01-01 | 1956-02-29 | Gillette Industries Ltd | Improvements in or relating to the dyeing of hair and other keratinous material |
| GB745532A (en) * | 1953-01-01 | 1956-02-29 | Gillette Industries Ltd | Improvements in or relating to the dyeing of hair and other keratinous material |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3920384A (en) * | 1974-07-17 | 1975-11-18 | Clairol Inc | Autoxidizable hair dye containing preparations |
| JPS5135441A (en) * | 1974-07-17 | 1976-03-25 | Bristol Myers Co | Jidosankaseimohatsusenryoto sonoseiho |
| US4054413A (en) * | 1974-07-17 | 1977-10-18 | Clairol Incorporated | Autoxidizable hair dye containing preparations |
| JPS6039645B2 (ja) * | 1974-07-17 | 1985-09-06 | ブリストル マイヤーズ カンパニー | 自動酸化性毛髪染料とその製法 |
| US4529404A (en) * | 1976-06-30 | 1985-07-16 | Clairol Incorporated | Hair dye preparation |
| 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1126565B (de) | 1962-03-29 |
| BE564088A (ja) | |
| CH348511A (fr) | 1960-08-31 |
| GB827439A (en) | 1960-02-03 |
| NL224268A (ja) |
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