US2719104A - Dyeing composition and process for keratinaceous material - Google Patents
Dyeing composition and process for keratinaceous material Download PDFInfo
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- US2719104A US2719104A US236275A US23627551A US2719104A US 2719104 A US2719104 A US 2719104A US 236275 A US236275 A US 236275A US 23627551 A US23627551 A US 23627551A US 2719104 A US2719104 A US 2719104A
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- 239000000203 mixture Substances 0.000 title claims description 61
- 238000004043 dyeing Methods 0.000 title claims description 48
- 239000000463 material Substances 0.000 title claims description 42
- 238000000034 method Methods 0.000 title description 10
- 229910001868 water Inorganic materials 0.000 claims description 51
- 239000000243 solution Substances 0.000 claims description 45
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 43
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 40
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 40
- 150000003839 salts Chemical class 0.000 claims description 29
- 239000007864 aqueous solution Substances 0.000 claims description 24
- 229910052742 iron Inorganic materials 0.000 claims description 20
- 229910052759 nickel Inorganic materials 0.000 claims description 20
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims description 18
- 229910052748 manganese Inorganic materials 0.000 claims description 18
- 239000011572 manganese Substances 0.000 claims description 18
- -1 THIOL COMPOUND Chemical class 0.000 claims description 17
- 229910017052 cobalt Inorganic materials 0.000 claims description 17
- 239000010941 cobalt Substances 0.000 claims description 17
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 17
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 32
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 25
- 229910052751 metal Inorganic materials 0.000 description 22
- 239000002184 metal Substances 0.000 description 22
- 229910052797 bismuth Inorganic materials 0.000 description 17
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 17
- 235000002908 manganese Nutrition 0.000 description 17
- 229910021529 ammonia Inorganic materials 0.000 description 16
- 210000002268 wool Anatomy 0.000 description 16
- 210000004209 hair Anatomy 0.000 description 12
- 239000003513 alkali Substances 0.000 description 10
- 239000003921 oil Substances 0.000 description 10
- 239000003086 colorant Substances 0.000 description 7
- 229910001385 heavy metal Inorganic materials 0.000 description 7
- GNBVPFITFYNRCN-UHFFFAOYSA-M sodium thioglycolate Chemical compound [Na+].[O-]C(=O)CS GNBVPFITFYNRCN-UHFFFAOYSA-M 0.000 description 7
- 229940046307 sodium thioglycolate Drugs 0.000 description 7
- 239000000975 dye Substances 0.000 description 6
- DOGJSOZYUGJVKS-UHFFFAOYSA-N glyceryl monothioglycolate Chemical compound OCC(O)COC(=O)CS DOGJSOZYUGJVKS-UHFFFAOYSA-N 0.000 description 6
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 6
- 239000004615 ingredient Substances 0.000 description 5
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- 235000011114 ammonium hydroxide Nutrition 0.000 description 4
- 239000000080 wetting agent Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 150000002736 metal compounds Chemical class 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 125000003396 thiol group Chemical group [H]S* 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethyl mercaptane Natural products CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 2
- 150000002696 manganese Chemical class 0.000 description 2
- PJUIMOJAAPLTRJ-UHFFFAOYSA-N monothioglycerol Chemical compound OCC(O)CS PJUIMOJAAPLTRJ-UHFFFAOYSA-N 0.000 description 2
- 150000002815 nickel Chemical class 0.000 description 2
- 239000012266 salt solution Substances 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 150000003573 thiols Chemical class 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- 102000011782 Keratins Human genes 0.000 description 1
- 108010076876 Keratins Proteins 0.000 description 1
- 229910021380 Manganese Chloride Inorganic materials 0.000 description 1
- GLFNIEUTAYBVOC-UHFFFAOYSA-L Manganese chloride Chemical compound Cl[Mn]Cl GLFNIEUTAYBVOC-UHFFFAOYSA-L 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical class [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- ZZTCCAPMZLDHFM-UHFFFAOYSA-N ammonium thioglycolate Chemical compound [NH4+].[O-]C(=O)CS ZZTCCAPMZLDHFM-UHFFFAOYSA-N 0.000 description 1
- 229940075861 ammonium thioglycolate Drugs 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 150000001621 bismuth Chemical class 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 150000001868 cobalt Chemical class 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- PPNKDDZCLDMRHS-UHFFFAOYSA-N dinitrooxybismuthanyl nitrate Chemical compound [Bi+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O PPNKDDZCLDMRHS-UHFFFAOYSA-N 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical class CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 210000003746 feather Anatomy 0.000 description 1
- 150000002505 iron Chemical class 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 150000003893 lactate salts Chemical class 0.000 description 1
- 235000002867 manganese chloride Nutrition 0.000 description 1
- 239000011565 manganese chloride Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 239000000473 propyl gallate Substances 0.000 description 1
- 229940075579 propyl gallate Drugs 0.000 description 1
- 235000010388 propyl gallate Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000002699 waste material Substances 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
- A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
-
- 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
- A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
-
- 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
- D06P3/3083—Material containing basic nitrogen containing amide groups furs feathers, dead hair, furskins, pelts preparing non-azo dyes on the material
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/916—Natural fiber dyeing
- Y10S8/917—Wool or silk
Definitions
- the present invention relates to a novel dyeing composition for keratinaceous material, such as hair, wool, fur, feathers and the like.
- the dye compositions of the present invention are capable of producing a variety of colors and a variety of shades in the various colors, depending upon variations in time, concentration and pH of the dye composition employed.
- the dyed materials are permanently dyed the desired color and are particularly desirable for hair dyeing, inasmuch as they are harmless when used as herein described.
- compositions of the present invention are composed of a plurality of components.
- the essential components are three, (1) a water soluble thiol compound, such as a water soluble thiol salt or an ester, (2) a soluble heavy metal salt and (3) an alkali.
- the compositions may contain a plurality of additional optional ingredients.
- a desirable ingredient is a wetting agent of the non-soapy type. Typical of these wetting agents are alkylaryl sulphonates, sulphated lauryl alcohol and sulphonated oils.
- the composition may be thickened with a water soluble gum as an additional optional ingredient. The particular forms of the compositions will be described in more detail hereinafter.
- thioglycolic acid employed in the form of its salts such as sodium and ammonium salts
- other thiol compounds which are water soluble may be used. These include the glycerol ester of thioglycolic acid, as Well as other esters of thioglycolic acid.
- 2 -mercaptyl. ethanol SHCI-IzCHzOH
- any Water soluble compound having a thiol group may be employed.
- the heavy metal salts include a considerable number, of which cobalt, nickel, iron, manganese and bismuth are particularly desirable. A variety of colors may be obtained from these metals, varying from a bright yellow with bismuth to a very dark brown, almost black color when using nickel. Cobalt and manganese give a variety of brown colors, Whereas iron produces a reddish brown color.
- the heavy metal may be employed in any of a variety of water soluble salts. Of these the sulphates, chlorides, acetates, lactates, nitrates, some carbonates and subcarbonates may be employed. It will be appreciated that the salt which is selected for any particular metal should be a water soluble salt.
- any water soluble alkaline material may be employed.
- this alkali is an organic alkali and preferably volatile; such as ammonia, amines and the like.
- Suitable amines include methyl, ethyl, propyl, isopropyl amines or diamines, monoethanolamine, morpholine and numerous other similar compounds.
- Inorganic alkaline materials such as sodium and potassium hydroxides, carbonates, phopshates and the like, which do not interfere with the heavy metal salts may be employed.
- the dyeing compositions in condition for actual use are in aqueous solution. Under these circumstances a complex is formed of the alkali, the thiol compound and the metal salt. These complexes are colored and are water soluble. They have an apparent afiinity for any material containing keratin and can be used for dyeing keratinaceous materials by the simple application of the aqueous solution thereto. For the purpose of obtaining a uniform dyeing, it is preferred to have the composition contain a non-soapy wetting agent, which serves to bring the aqueous solution into uniform contact with all of the filaments. The complex appears to form a further complex with the thiol groups contained in the keratinaceous material.
- these dyeing compositions may be packaged in a variety of ways.
- Some of the finished dyeing compositions are unstable when kept for extended periods of time, and accordingly it is preferred that they be mixed shortly prior to the time of use.
- iron and manganese tend to oxidize the thiol group in the thiol compound and accordingly cause the mixture to lose its dyeing power when stored over extended periods of time. Accordingly, with such compositions it is preferred to maintain the iron and manganese salts separate from the thiol compounds until immediately prior to use.
- Antioxidants such as propylgallate may be used to delay the oxidation of such mixed dyeing compositions.
- solutions containing soluble nickel salts have been kept for several months in admixture with the thiol compound without any apparent deterioration of the dyeing power of the material. It is often desirable to package these compositions in the form of two aqueous solutions, one containing the soluble metal salt and the other containing the alkali and the thiol compound. One of these solutions can then also contain the wetting agent and a water soluble gum as a thickening agent.
- the respective solutions may be formulated in the form of a cream with an emulsified oil base or mixed with a sulphonated oil.
- the materials may be supplied in the form of the dry ingredients which can be mixed by the user. Any of this variety of ways of preparing the composition may be employed.
- the dyeing operation may also be effected by first treating the material to be dyed with the thiol compound and then treating the material, either with or without prior rinsing with the heavy metal salt solution. In this manner, the color develops first right in the material being dyed rather than as a color complex which is added as such to the material. It should be pointed out that where the thiol compound and the metal salt are used separately as described immediately above, the thiol solution alone need be alkaline for reaction with the keratinaceous material.
- the heavy metal salt solution may be acid, neutral or alkaline as desired, and the dyeing action is still obtainable.
- the pH of the dyeing composition may be varied widely to produce different effects. Some of the metals employed in the present dying compositions will transmit the dye to white wool yarn under a Wide range of pH, ranging from slightly acid to strongly alkaline. A pref- 3 erable pH is from 8 to 10.5. The depth of the color varies directly with the pH, the deepest color being achieved at the highest pH. For example, by varying the pH of nickel-containing dyeing compositions, it is possible to vary the color from light brown to a very dark brown or almost black.
- Variations in color may also be obtained by varying the amounts of the metal present and the concentration of the complex used. It is preferred to employ the alkali, the thiol compound and the metal compound in substantially equivalent amounts. It will be apparent that an excess of any of the components of the composition will not adversely affect the action of the combination but will be essentially a waste of that particular component. Colors may also be varied by the use of combinations of metals rather than a single metal. As illustrated in the following examples the metal compound should preferably be present in an amount at least about 3.3 per cent by weight of the total dyeing solution and preferably from about to per cent. While it is preferred to employ the alkali, the thiol compound and the metal compound in substantially equivalent amounts they may be varied considerably as shown in the examples.
- composition In employing the composition it is merely necessary to apply the composition to the material to be dyed and usually from 5 to 10 minutes is sufficient time to effect a satisfactory dyeing operation. Usually beyond this time period no further dyeing action is obtained. Variation in the color may be obtained by shortening the dyeing period below the 5 to 10 minutes which effects the full action of the dye.
- White wool yarn was dyed with this solution for periods of 5, 10 and 15 minutes. In this instance the dyeing reaction did not appear to be complete within five minutes but had been approximately completed in ten minutes. All of these samples were somewhat lighter than the samples dyed in Examples 1 and 2.
- Example 4 The dyeing solution in Example 3 was diluted with an equal volume of water. White wool yarn was dyed with this diluted solution for periods of 5, l0 and 15 minutes. The sample treated for five minutes was a light cream to tan color, the ten minute sample was a tan color, and the fifteen minute sample was a fairly dark tan color.
- Example 5 The solution of Example 3 was diluted with twice its volume of water and white wool yarn was again dyed for periods of 5, 10 and 15 minutes. The solution was effective to tint the yarn, the depth of the tint increasing with the length of time. The fifteen minute sample was slightly lighter in color than the ten minute sample of Example 4.
- White wool yarn was dyed with this solution for periods of 5, 10 and 15 minutes.
- the five-minute sample was a distinct tan color, whereas the 10 and 15 minutes samples were progressively darker.
- Cotton yarn and wool yarn were treated simultaneously with the dyeing solution.
- the wool yarn immediately picked up the dye color, whereas the cotton remained its original white color.
- Solution A was a water white solution and was applied to hair and was rinsed out completely. The hair, while still damp was then treated with solution B which was only slightly colored, and the hair immediately took on a deep brown color.
- Example 12 Grams Glyceryl thioglycolate 50% (Evans Chemetics Thiovanol) 12.0 Bismuth nitrat 10.0 Isopropylamine and water sufficient to make 100.0 cc.
- the above examples are also useful for the dyeing of human hair.
- one of the nickel dyeing solutions was employed to dye blond hair. At a pH of 8.5 the hair took on a light brown color, at a pH of 9.5 the hair took on a quite deep brown color, whereas at a pH of 10.5 the hair became almost black.
- a dyeing composition for keratinaceous material comprising an aqueous solution of a water soluble thiol 6 compound, a water soluble salt of a metal selected from the group consisting of cobalt, nickel, iron, manganese and bismuth in an amount equal to at least about 3.3 per cent by weight of the total composition and a water soluble alkaline material, the solution having a pH Within the approximate range of 8-105.
- a dyeing composition for keratinaceous material comprising an aqueous solution of a water soluble salt of thioglycolic acid, a water soluble salt of a metal selected from the group consisting of cobalt, nickel, iron, manganese and bismuth in an amount equal to at least about 3.3 per cent by weight of the total composition and a volatile alkali, the solution having a pH Within the approximate range of 8-105.
- a dyeing composition for keratinaceous material comprising an aqueous solution of sodium thioglycolate, a water soluble salt of a metal selected from the group consisting of cobalt, nickel, iron, manganese and bismuth in an amount equal to at least about 3.3 per cent by Weight of the total composition and ammonia, the solution having a pH within the approximate range of 8-105.
- a dyeing composition for keratinaceous material comprising an aqueous solution of sodium thioglycolate, a water soluble cobalt salt in an amountequal to at least about 3.3 per cent by weight of the total composition and ammonia, the solution having a pH within the approximate range of 8-105.
- a dyeing composition for keratinaceous material comprising an aqueous solution of sodium thioglycolate, a water soluble nickel salt in an amount equal to at least about 3.3 per cent by weight of the total composition and ammonia, the solution having a pH within the approximate range of 8-105.
- a dyeing composition for keratinaceous material comprising an aqueous solution of sodium thioglycolate, a water soluble iron salt in an amount equal to at least about 3.3 per cent by weight of the total composition and ammonia, the solution having a pH within the approximate range of 8-105.
- a dyeing composition for keratinaceous material comprising an aqueous solution of sodium thioglycolate, a water soluble manganese salt in an amount equal to at least about 3.3 per cent by weight of the total composition and ammonia, the solution having a pH Within the approximate range of 8-105.
- a dyeing composition for keratinaceous material comprising an aqueous solution of sodium thioglycolate, a water soluble bismuth salt in an amount equal to at least about 3.3 per cent by weight of the total composition and ammonia, the solution having a pH within the approximate range of 8-105.
- a dyeing composition for keratinaceous material comprising an aqueous solution of a water soluble ester of thioglycolic acid, a Water salt of a metal selected from the group consisting of cobalt, nickel, iron, manganese and bismuth in an amount equal to at least about 3.3 per cent by weight of the total composition, and a volatile alkali, the solution having a pH within the approximate range of 8-105.
- a dyeing composition for keratinaceous material comprising an aqueous solution of glyceryl thioglycolate, a water soluble salt of a metal selected from the group consisting of cobalt, nickel, iron, manganese and bismuth in an amount equal to at least about 3.3 per cent by weight of the total composition and ammonia, the solution having a pH within the approximate range of 8-105.
- a dyeing composition for keratinaceous material comprising an aqueous solution of 2-mercaptoethanol, a water soluble salt of a metal selected from the group consisting of cobalt, nickel, iron, manganese and bismuth in an amount equal to at least about 3.3 per cent by weight of the total composition and ammonia, the solution having a pH within the approximate range of 8-105.
- a process of dyeing keratinaceous material which comprises applying thereto an aqueous solution of a water soluble thiol compound, a water soluble salt of a heavy metal in an amount equal to at least about 3.3 per cent by weight of the total composition and a water soluble alkaline material, the solution having a pH within the approximate range of 8-10.5.
- the process of dyeing keratinaceous material which comprises applying thereto an aqueous solution of a soluble salt .of thioglycolic acid, a soluble salt of a metal selected from the group consisting of cobalt, nickel, iron, manganese and bismuth in an amount equal to at least about 3.3 per cent by weight of the total composition, and a water soluble alkaline material, the solution having a pH within the approximate range of 810.5.
- the process of dyeing keratinaceous material which comprises applying thereto an aqueous solution of a soluble salt of thioglycolic acid, a soluble salt of a metal selected from the group consisting of cobalt, nickel, iron, manganese and bismuth in an amount equal to at least about 3.3 per cent by Weight of the total composition, and a volatile alkali, the solution having a pH within the approximate range of 8-10.5.
- the process of dyeing keratinaceous material which comprises applying thereto an aqueous solution of a soluble salt of thioglycolic acid, a soluble salt of a metal selected from the group consisting of cobalt, nickel, iron, manganese and bismuth in an amount equal to at least about 3.3 per cent by weight of the total composition, and and ammonia, the solution having a pH within the approximate range of 8-10.5.
- the process of dyeing keratinaceous material which comprises applying thereto an aqueous solution of ammonium thioglycolate, a water soluble salt of a metal selected from the group consisting of cobalt, nickel, iron, manganese and bismuth in an amount equal to at least about 3.3 per cent by weight of the total composition and ammonia, the Solution having a pH within the approximate range of 810.5.
- the process of dyeing keratinaceous material which comprises applying thereto an aqueous solution of sodium thioglycolate, a water soluble salt of a metal selected from 8 the group consisting of cobalt, nickel, iron, manganese and bismuth in an amount equal to at least about 3.3 per cent by weight of the total composition and ammonia, the solution having a pH within the approximate range of 53-105.
- the process of dyeing keratinaceous material which comprises applying thereto an aqueous solution of glyceryl thioglycolate, a water soluble salt of a metal selected from the group consisting of cobalt, nickel, iron, manganese and bismuth in an amount equal to at least about 3.3 per cent by weight of the total composition and ammonia, the solution having a pH within the approximate range of 8-10.5.
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- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Textile Engineering (AREA)
- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Inorganic Chemistry (AREA)
- Cosmetics (AREA)
- Coloring (AREA)
Description
United States Patent DYEING COMPOSITION AND PROCESS FOR KERATINACEOUS MATERIAL Carl G. Westerberg, Sierra Madre, Calif.
No Drawing. Application July 11, 1951,
Serial No. 236,275
19 Claims. (Cl. 16788) The present invention relates to a novel dyeing composition for keratinaceous material, such as hair, wool, fur, feathers and the like. The dye compositions of the present invention are capable of producing a variety of colors and a variety of shades in the various colors, depending upon variations in time, concentration and pH of the dye composition employed. The dyed materials are permanently dyed the desired color and are particularly desirable for hair dyeing, inasmuch as they are harmless when used as herein described.
It is therefore an object of the present invention to provide novel hair dyeing compositions capable of producing a variety of colors and a variety of shades in the various colors.
It is another object of the present invention to provide a novel hair-dyeing composition which is completely harmless, and which is capable of simple and easy use by the inexperienced user to produce evenly dyed hair which permanently retains the desired color.
The compositions of the present invention are composed of a plurality of components. The essential components are three, (1) a water soluble thiol compound, such as a water soluble thiol salt or an ester, (2) a soluble heavy metal salt and (3) an alkali. In addition, the compositions may contain a plurality of additional optional ingredients. A desirable ingredient is a wetting agent of the non-soapy type. Typical of these wetting agents are alkylaryl sulphonates, sulphated lauryl alcohol and sulphonated oils. The composition may be thickened with a water soluble gum as an additional optional ingredient. The particular forms of the compositions will be described in more detail hereinafter.
Considerable variation is possible in each of the essential ingredients. Thus, with reference to the thiol compound, it has been found that thioglycolic acid employed in the form of its salts such as sodium and ammonium salts, is particularly desirable and readily available for this purpose. However, other thiol compounds which are water soluble may be used. These include the glycerol ester of thioglycolic acid, as Well as other esters of thioglycolic acid. Similarly, 2 -mercaptyl. ethanol (SHCI-IzCHzOH) may be used. In place of these specific materials any Water soluble compound having a thiol group may be employed.
As to the heavy metal salts that may be employed, these include a considerable number, of which cobalt, nickel, iron, manganese and bismuth are particularly desirable. A variety of colors may be obtained from these metals, varying from a bright yellow with bismuth to a very dark brown, almost black color when using nickel. Cobalt and manganese give a variety of brown colors, Whereas iron produces a reddish brown color. The heavy metal may be employed in any of a variety of water soluble salts. Of these the sulphates, chlorides, acetates, lactates, nitrates, some carbonates and subcarbonates may be employed. It will be appreciated that the salt which is selected for any particular metal should be a water soluble salt.
Fee
Almost any water soluble alkaline material may be employed. Preferably this alkali is an organic alkali and preferably volatile; such as ammonia, amines and the like. Suitable amines include methyl, ethyl, propyl, isopropyl amines or diamines, monoethanolamine, morpholine and numerous other similar compounds. Inorganic alkaline materials, such as sodium and potassium hydroxides, carbonates, phopshates and the like, which do not interfere with the heavy metal salts may be employed.
The dyeing compositions in condition for actual use are in aqueous solution. Under these circumstances a complex is formed of the alkali, the thiol compound and the metal salt. These complexes are colored and are water soluble. They have an apparent afiinity for any material containing keratin and can be used for dyeing keratinaceous materials by the simple application of the aqueous solution thereto. For the purpose of obtaining a uniform dyeing, it is preferred to have the composition contain a non-soapy wetting agent, which serves to bring the aqueous solution into uniform contact with all of the filaments. The complex appears to form a further complex with the thiol groups contained in the keratinaceous material.
For the purpose of marketing these dyeing compositions they may be packaged in a variety of ways. Some of the finished dyeing compositions are unstable when kept for extended periods of time, and accordingly it is preferred that they be mixed shortly prior to the time of use. Thus iron and manganese tend to oxidize the thiol group in the thiol compound and accordingly cause the mixture to lose its dyeing power when stored over extended periods of time. Accordingly, with such compositions it is preferred to maintain the iron and manganese salts separate from the thiol compounds until immediately prior to use. Antioxidants such as propylgallate may be used to delay the oxidation of such mixed dyeing compositions.
In contrast to the instability of these iron and man ganese compositions, solutions containing soluble nickel salts have been kept for several months in admixture with the thiol compound without any apparent deterioration of the dyeing power of the material. It is often desirable to package these compositions in the form of two aqueous solutions, one containing the soluble metal salt and the other containing the alkali and the thiol compound. One of these solutions can then also contain the wetting agent and a water soluble gum as a thickening agent. As an alternative the respective solutions may be formulated in the form of a cream with an emulsified oil base or mixed with a sulphonated oil. In addition the materials may be supplied in the form of the dry ingredients which can be mixed by the user. Any of this variety of ways of preparing the composition may be employed.
The dyeing operation may also be effected by first treating the material to be dyed with the thiol compound and then treating the material, either with or without prior rinsing with the heavy metal salt solution. In this manner, the color develops first right in the material being dyed rather than as a color complex which is added as such to the material. It should be pointed out that where the thiol compound and the metal salt are used separately as described immediately above, the thiol solution alone need be alkaline for reaction with the keratinaceous material. The heavy metal salt solution may be acid, neutral or alkaline as desired, and the dyeing action is still obtainable.
The pH of the dyeing composition may be varied widely to produce different effects. Some of the metals employed in the present dying compositions will transmit the dye to white wool yarn under a Wide range of pH, ranging from slightly acid to strongly alkaline. A pref- 3 erable pH is from 8 to 10.5. The depth of the color varies directly with the pH, the deepest color being achieved at the highest pH. For example, by varying the pH of nickel-containing dyeing compositions, it is possible to vary the color from light brown to a very dark brown or almost black.
Variations in color may also be obtained by varying the amounts of the metal present and the concentration of the complex used. It is preferred to employ the alkali, the thiol compound and the metal compound in substantially equivalent amounts. It will be apparent that an excess of any of the components of the composition will not adversely affect the action of the combination but will be essentially a waste of that particular component. Colors may also be varied by the use of combinations of metals rather than a single metal. As illustrated in the following examples the metal compound should preferably be present in an amount at least about 3.3 per cent by weight of the total dyeing solution and preferably from about to per cent. While it is preferred to employ the alkali, the thiol compound and the metal compound in substantially equivalent amounts they may be varied considerably as shown in the examples.
In employing the composition it is merely necessary to apply the composition to the material to be dyed and usually from 5 to 10 minutes is sufficient time to effect a satisfactory dyeing operation. Usually beyond this time period no further dyeing action is obtained. Variation in the color may be obtained by shortening the dyeing period below the 5 to 10 minutes which effects the full action of the dye.
The following examples will serve to illustrate the invention:
Example 1 Thioglycolic acid 70% cc 7.0 NHiOH 28% cc 30.0 Sulphonated oil cc 1.0 NiCl2.6H2O gr 10.0
H2O to make 100.0 cc.
Example 2 Thioglycolic acid 70% cc 7.0 NHQOH 28% cc 20.0 Sulphonated oil cc 1.0 NiCl2.6H2O "grams" 10.0
H2O to make 100.0 cc.
White wool yarn was dyed for periods of 5, 10 and minutes. Again the dyeing reaction was substantially complete in the first five minutes and there was little variation in color between the samples. These samples were approximately the same color as the dyed wool samples of Example 1.
Example 3 Thioglycolic acid 70% cc 7.0 NH4OH 28% 10.0 Sulphonated il cc 1.0 NiCl2.6H2O grams 10.0
H2O to make 100.0 cc.
White wool yarn was dyed with this solution for periods of 5, 10 and 15 minutes. In this instance the dyeing reaction did not appear to be complete within five minutes but had been approximately completed in ten minutes. All of these samples were somewhat lighter than the samples dyed in Examples 1 and 2.
4 Example 4 The dyeing solution in Example 3 Was diluted with an equal volume of water. White wool yarn was dyed with this diluted solution for periods of 5, l0 and 15 minutes. The sample treated for five minutes was a light cream to tan color, the ten minute sample was a tan color, and the fifteen minute sample was a fairly dark tan color.
Example 5 The solution of Example 3 was diluted with twice its volume of water and white wool yarn was again dyed for periods of 5, 10 and 15 minutes. The solution was effective to tint the yarn, the depth of the tint increasing with the length of time. The fifteen minute sample was slightly lighter in color than the ten minute sample of Example 4.
Example 6 Glyceryl thioglycolate 50% (Evans Chemetics Thiovanol) cc 10.0 NHQOH 28% cc 10.0 NiCl2.6H2O grams 10.0 Sulphonated oil cc 1.0
H20 to make 100.0 cc.
White wool yarn was dyed with this solution for periods of 5, 10 and 15 minutes. The five-minute sample was a distinct tan color, whereas the 10 and 15 minutes samples were progressively darker.
Example 7 Glyceryl thioglycolate 50% cc 10.0 NH4OH 28% cc 30.0 NiCl2.6H2O grams 10.0 Sulphonated oil cc 1.0
H20 to make 100.0 cc.
Example 8 Mercaptoethanol cc 6.0 NH4OH 28% cc 20.0 Sulphonated oil cc 1.0 NiCl2.6H2O rams" 10.0
H2O to make 100.0 cc.
White wool yarn was dyed for five minutes with this solution and took on a very dark brown color.
Cotton yarn and wool yarn were treated simultaneously with the dyeing solution. The wool yarn immediately picked up the dye color, whereas the cotton remained its original white color.
Example 9 Solution A:
Thioglycolic acid 70% cc 7.0 NH4OH 28% cc 20.0 Sulphonated oil cc 1.0 H20 to make 100.0 cc.
Solution B:
NiCl2.6H2O grams 10.0 Sulphonated oil cc 1.0
H20 to make 100.0 cc.
Solution A was a water white solution and was applied to hair and was rinsed out completely. The hair, while still damp was then treated with solution B which was only slightly colored, and the hair immediately took on a deep brown color.
Mix A and B prior to use.
These solutions were made up and were then mixed immediately prior to use. The results obtained with this are the same as those obtained with Example 2. This example demonstrates the possibility of preparing separate solutions which may be sold as such and which may be mixed immediately prior to use.
Example 11 Grams Thioglycolic acid 6.0 Cobalt a tat 10.0
Morpholine and water suflicient to make 100.0 cc. and
a pH of 9.5.
White wool yarn dyed with this solution took on a deep brown color.
Example 12 Grams Glyceryl thioglycolate 50% (Evans Chemetics Thiovanol) 12.0 Bismuth nitrat 10.0 Isopropylamine and water sufficient to make 100.0 cc.
and a pH of 10.
White wool yarn was dyed with this solution and took on a brilliant yellow color.
Example 13 Grams Glyceryl thioglycolate 12.0 Ferric sulphat 10.0
Ammonia and water sufiicient to make 100.0 cc. and
a pH of 10.5.
White wool yarn was dyed with this solution and the yarn immediately took on a reddish brown typically iron color.
Example 14 Grams Mercaptoethanol 6.0 Manganous chloride 10.0
Water and ammonia sufiicient to make 100.0 cc. and a pH of 8.
White wool yarn was dyed with this solution and took on a very dark brown color.
The above examples are also useful for the dyeing of human hair. For example, one of the nickel dyeing solutions was employed to dye blond hair. At a pH of 8.5 the hair took on a light brown color, at a pH of 9.5 the hair took on a quite deep brown color, whereas at a pH of 10.5 the hair became almost black.
In addition, various samples of white wool yarn were dyed with mixtures of bismuth and nickel. By this means it was able to control the depth of the brown color so that any minute variation between the bright yellow color obtained with the bismuth and the deep brown obtained with nickel was obtainable.
As many apparently Widely different embodiments of this invention may be made Without departing from the spirit and scope thereof, it is to be understood that I do not limit myself to the specific embodiments herein.
What I claim is:
1. A dyeing composition for keratinaceous material comprising an aqueous solution of a water soluble thiol 6 compound, a water soluble salt of a metal selected from the group consisting of cobalt, nickel, iron, manganese and bismuth in an amount equal to at least about 3.3 per cent by weight of the total composition and a water soluble alkaline material, the solution having a pH Within the approximate range of 8-105.
2. A dyeing composition for keratinaceous material comprising an aqueous solution of a water soluble salt of thioglycolic acid, a water soluble salt of a metal selected from the group consisting of cobalt, nickel, iron, manganese and bismuth in an amount equal to at least about 3.3 per cent by weight of the total composition and a volatile alkali, the solution having a pH Within the approximate range of 8-105.
3. A dyeing composition for keratinaceous material comprising an aqueous solution of sodium thioglycolate, a water soluble salt of a metal selected from the group consisting of cobalt, nickel, iron, manganese and bismuth in an amount equal to at least about 3.3 per cent by Weight of the total composition and ammonia, the solution having a pH within the approximate range of 8-105.
4. A dyeing composition for keratinaceous material comprising an aqueous solution of sodium thioglycolate, a water soluble cobalt salt in an amountequal to at least about 3.3 per cent by weight of the total composition and ammonia, the solution having a pH within the approximate range of 8-105.
5. A dyeing composition for keratinaceous material comprising an aqueous solution of sodium thioglycolate, a water soluble nickel salt in an amount equal to at least about 3.3 per cent by weight of the total composition and ammonia, the solution having a pH within the approximate range of 8-105.
6. A dyeing composition for keratinaceous material comprising an aqueous solution of sodium thioglycolate, a water soluble iron salt in an amount equal to at least about 3.3 per cent by weight of the total composition and ammonia, the solution having a pH within the approximate range of 8-105.
7. A dyeing composition for keratinaceous material comprising an aqueous solution of sodium thioglycolate, a water soluble manganese salt in an amount equal to at least about 3.3 per cent by weight of the total composition and ammonia, the solution having a pH Within the approximate range of 8-105.
8. A dyeing composition for keratinaceous material comprising an aqueous solution of sodium thioglycolate, a water soluble bismuth salt in an amount equal to at least about 3.3 per cent by weight of the total composition and ammonia, the solution having a pH within the approximate range of 8-105.
9. A dyeing composition for keratinaceous material comprising an aqueous solution of a water soluble ester of thioglycolic acid, a Water salt of a metal selected from the group consisting of cobalt, nickel, iron, manganese and bismuth in an amount equal to at least about 3.3 per cent by weight of the total composition, and a volatile alkali, the solution having a pH within the approximate range of 8-105.
10. A dyeing composition for keratinaceous material comprising an aqueous solution of glyceryl thioglycolate, a water soluble salt of a metal selected from the group consisting of cobalt, nickel, iron, manganese and bismuth in an amount equal to at least about 3.3 per cent by weight of the total composition and ammonia, the solution having a pH within the approximate range of 8-105.
11. A dyeing composition for keratinaceous material comprising an aqueous solution of 2-mercaptoethanol, a water soluble salt of a metal selected from the group consisting of cobalt, nickel, iron, manganese and bismuth in an amount equal to at least about 3.3 per cent by weight of the total composition and ammonia, the solution having a pH within the approximate range of 8-105.
12. A process of dyeing keratinaceous material which comprises applying thereto an aqueous solution of a water soluble thiol compound, a water soluble salt of a heavy metal in an amount equal to at least about 3.3 per cent by weight of the total composition and a water soluble alkaline material, the solution having a pH within the approximate range of 8-10.5.
13. The process of dyeing keratinaceous material which comprises applying thereto an aqueous solution of a soluble salt .of thioglycolic acid, a soluble salt of a metal selected from the group consisting of cobalt, nickel, iron, manganese and bismuth in an amount equal to at least about 3.3 per cent by weight of the total composition, and a water soluble alkaline material, the solution having a pH within the approximate range of 810.5.
14. The process of dyeing keratinaceous material which comprises applying thereto an aqueous solution of a soluble salt of thioglycolic acid, a soluble salt of a metal selected from the group consisting of cobalt, nickel, iron, manganese and bismuth in an amount equal to at least about 3.3 per cent by Weight of the total composition, and a volatile alkali, the solution having a pH within the approximate range of 8-10.5.
15. The process of dyeing keratinaceous material which comprises applying thereto an aqueous solution of a soluble salt of thioglycolic acid, a soluble salt of a metal selected from the group consisting of cobalt, nickel, iron, manganese and bismuth in an amount equal to at least about 3.3 per cent by weight of the total composition, and and ammonia, the solution having a pH within the approximate range of 8-10.5.
16. The process of dyeing keratinaceous material which comprises applying thereto an aqueous solution of ammonium thioglycolate, a water soluble salt of a metal selected from the group consisting of cobalt, nickel, iron, manganese and bismuth in an amount equal to at least about 3.3 per cent by weight of the total composition and ammonia, the Solution having a pH within the approximate range of 810.5.
17. The process of dyeing keratinaceous material which comprises applying thereto an aqueous solution of sodium thioglycolate, a water soluble salt of a metal selected from 8 the group consisting of cobalt, nickel, iron, manganese and bismuth in an amount equal to at least about 3.3 per cent by weight of the total composition and ammonia, the solution having a pH within the approximate range of 53-105.
18. The process of dyeing keratinaceous material which comprises applying thereto an aqueous solution of glyceryl thioglycolate, a water soluble salt of a metal selected from the group consisting of cobalt, nickel, iron, manganese and bismuth in an amount equal to at least about 3.3 per cent by weight of the total composition and ammonia, the solution having a pH within the approximate range of 8-10.5.
19. The process of dyeing keratinaceous material which comprises applying thereto an aqueous solution of 2- mercaptoethanol, a water soluble salt of a metal selected from the group consisting of cobalt, nickel, iron, manganese and bismuth in an amount equal to at least about 3.3 per cent by weight of the total composition and ammonia, the solution having a pH within the approximate range of 810.5.
References Cited in the fileof this patent UNITED STATES PATENTS 1,937,365 Stoddard Nov. 28, 1933 2,261,094 Speakman Oct. 28, 1941 2,540,980 Den Beste Feb. 6, 1951 FOREIGN PATENTS 117,071 Australia June 3, 1943 318,045 France Oct. 4, 1902 OTHER REFERENCES Hall: Textile Colorist, February 1942, pp. 63-65.
Winter: Hair Dyes of Today, Soap Perfumery and Cosmetics, December 1938, pp. 1080-1084 and 1088; pp. 1081, 1082 and 1084 particularly pertinent.
Allen: Review of Hair Dyes, Soap Perfumery and Cosmetics, September 1938, pp. 815-817, and 819; p. 819 particularly pertinent.
Claims (1)
1. A DYEING COMPOSITION FOR KERATINACEOUS MATERIAL COMPRISING AN AQUEOUS SOLUTION OF A WATER SOLUBLE THIOL COMPOUND, A WATER SOLUBLE SALT OF A METAL SELECTED FROM THE GROUP CONSISTING OF COBALT, NICKEL, IRON, MANGANESE AND BISMUTH IN AN AMOUNT EQUAL TO AT LEAST ABOUT 3.3 PER CENT BY WEIGHT OF THE TOTAL COMPOSITION AND A WATER SOLUBLE ALKALINE MATERIAL, THE SOLUTION HAVING A PH WITHIN THE APPROXIMATE RANGE OF 8-10.5.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US236275A US2719104A (en) | 1951-07-11 | 1951-07-11 | Dyeing composition and process for keratinaceous material |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US236275A US2719104A (en) | 1951-07-11 | 1951-07-11 | Dyeing composition and process for keratinaceous material |
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|---|---|
| US2719104A true US2719104A (en) | 1955-09-27 |
Family
ID=22888839
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| US236275A Expired - Lifetime US2719104A (en) | 1951-07-11 | 1951-07-11 | Dyeing composition and process for keratinaceous material |
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| US (1) | US2719104A (en) |
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2904385A (en) * | 1956-07-17 | 1959-09-15 | Oreal | Dyeing animal fibres and compositions therefor |
| US3086832A (en) * | 1958-03-21 | 1963-04-23 | Process for finishing dyeings | |
| US3215605A (en) * | 1962-04-25 | 1965-11-02 | Revlon | Method for coloring hair and other keratinaceous fibers with metal salts |
| US3665935A (en) * | 1970-06-16 | 1972-05-30 | Kingshott Investments Propriet | Method of straightening keratinous fibers |
| US3966903A (en) * | 1973-05-04 | 1976-06-29 | Shiseido Co., Ltd. | Sulfite or bisulfite hair-waving composition containing a wave accelerating agent |
| US3973574A (en) * | 1965-11-25 | 1976-08-10 | Fumio Umezawa | Waving and straightening hair by producing metal chelates in the keratin of the hair |
| US4173453A (en) * | 1976-04-09 | 1979-11-06 | CDC Research Inc. | Topical hair coloring formulation in the form of suspension, lotion and cream |
| US4302199A (en) * | 1980-12-29 | 1981-11-24 | The Procter & Gamble Company | Hair dyeing 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 |
| US5635168A (en) * | 1994-09-21 | 1997-06-03 | Business Resources Group, Inc. | Composition for treating hair |
| US5942009A (en) * | 1997-03-28 | 1999-08-24 | Brg, Ltd. | Same-day waving and coloring of hair |
| US20030079300A1 (en) * | 2001-08-20 | 2003-05-01 | Cannell David W. | Methods for relaxing and re-waving hair comprising at least one reducing agent and at least one hydroxide compound |
| FR3158638A1 (en) * | 2024-01-31 | 2025-08-01 | L'oreal | Cosmetic treatment process for keratin fibers comprising the application of at least one bismuth salt and water |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR318045A (en) * | 1902-01-24 | 1902-10-04 | Bernard | A hair and beard dyeing process |
| US1937365A (en) * | 1932-04-25 | 1933-11-28 | Victor J Thill | Preparation for coloring hair |
| US2261094A (en) * | 1934-12-10 | 1941-10-28 | Speakman John Bamber | Treatment of keratins |
| US2540980A (en) * | 1946-10-16 | 1951-02-06 | Raymond Lab Inc | Process and composition for treating keratinous material |
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1951
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR318045A (en) * | 1902-01-24 | 1902-10-04 | Bernard | A hair and beard dyeing process |
| US1937365A (en) * | 1932-04-25 | 1933-11-28 | Victor J Thill | Preparation for coloring hair |
| US2261094A (en) * | 1934-12-10 | 1941-10-28 | Speakman John Bamber | Treatment of keratins |
| US2540980A (en) * | 1946-10-16 | 1951-02-06 | Raymond Lab Inc | Process and composition for treating keratinous material |
Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2904385A (en) * | 1956-07-17 | 1959-09-15 | Oreal | Dyeing animal fibres and compositions therefor |
| US3086832A (en) * | 1958-03-21 | 1963-04-23 | Process for finishing dyeings | |
| US3215605A (en) * | 1962-04-25 | 1965-11-02 | Revlon | Method for coloring hair and other keratinaceous fibers with metal salts |
| US3973574A (en) * | 1965-11-25 | 1976-08-10 | Fumio Umezawa | Waving and straightening hair by producing metal chelates in the keratin of the hair |
| US3665935A (en) * | 1970-06-16 | 1972-05-30 | Kingshott Investments Propriet | Method of straightening keratinous fibers |
| US3966903A (en) * | 1973-05-04 | 1976-06-29 | Shiseido Co., Ltd. | Sulfite or bisulfite hair-waving composition containing a wave accelerating agent |
| US4173453A (en) * | 1976-04-09 | 1979-11-06 | CDC Research Inc. | Topical hair coloring formulation in the form of suspension, lotion and cream |
| US4302199A (en) * | 1980-12-29 | 1981-11-24 | The Procter & Gamble Company | Hair dyeing 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 |
| US5635168A (en) * | 1994-09-21 | 1997-06-03 | Business Resources Group, Inc. | Composition for treating hair |
| US5942009A (en) * | 1997-03-28 | 1999-08-24 | Brg, Ltd. | Same-day waving and coloring of hair |
| US20030079300A1 (en) * | 2001-08-20 | 2003-05-01 | Cannell David W. | Methods for relaxing and re-waving hair comprising at least one reducing agent and at least one hydroxide compound |
| US7622104B2 (en) * | 2001-08-20 | 2009-11-24 | L'oreal S.A. | Methods for relaxing and re-waving hair comprising at least one reducing agent and at least one hydroxide compound |
| FR3158638A1 (en) * | 2024-01-31 | 2025-08-01 | L'oreal | Cosmetic treatment process for keratin fibers comprising the application of at least one bismuth salt and water |
| WO2025163274A1 (en) * | 2024-01-31 | 2025-08-07 | L'oreal | Method for the cosmetic treatment of keratin fibres, comprising the application of at least one bismuth salt and water |
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