CN116763672A - Preparation formula and method of air-oxidized single-agent hair dyeing product - Google Patents

Preparation formula and method of air-oxidized single-agent hair dyeing product Download PDF

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Publication number
CN116763672A
CN116763672A CN202210521173.2A CN202210521173A CN116763672A CN 116763672 A CN116763672 A CN 116763672A CN 202210521173 A CN202210521173 A CN 202210521173A CN 116763672 A CN116763672 A CN 116763672A
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China
Prior art keywords
water
air
soluble
hair dye
hair
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CN202210521173.2A
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Inventor
赵劲松
袁文钦
林晶晶
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Foshan Xizhuang Cosmetics Co ltd
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Foshan Xizhuang Cosmetics Co ltd
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Priority to CN202210521173.2A priority Critical patent/CN116763672A/en
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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/494Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • A61K8/4953Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom containing pyrimidine ring derivatives, e.g. minoxidil
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/96Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
    • A61K8/9783Angiosperms [Magnoliophyta]
    • A61K8/9789Magnoliopsida [dicotyledons]
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/10Preparations for permanently dyeing the hair
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/52Stabilizers
    • A61K2800/522Antioxidants; Radical scavengers

Abstract

The invention discloses a preparation formula and a preparation method of an air oxidation single-dose hair dye product, wherein the preparation formula comprises the following components in percentage by weight: the polyamino substituted pyrimidine ring compound accounts for 0.05 to 2.5 percent; the water-soluble metal salt is used as a catalyst, and the ratio of the water-soluble metal salt to the catalyst is 0-2%; an oxidative hair dyeing intermediate accounting for 0.1-5 percent; an oxidative hair dye coupler in an amount of 0.1-5%; extracting antioxidant and allergy relieving agent from plants with a ratio of 0.5-5%; 0.1-2% of water-soluble anionic polymer; an alkaline pH adjustor for adjusting pH to 9 to 11; a water-soluble surfactant in an amount of 1-5%; the water-soluble solvent accounts for 1-5%, and the invention uses the oxidative dye precursor which is sensitive to air, under the action of air, the oxidative dye precursor does not need to be mixed with the traditional oxidant, so that the ideal white hair coverage rate can be achieved, the packaging is simplified, the operation is convenient, the irritation of the oxidant to the scalp in the hair dyeing process can be reduced, and the commercialization is easy to realize.

Description

Preparation formula and method of air-oxidized single-agent hair dyeing product
Technical Field
The invention relates to a preparation formula of a single-agent hair dyeing product, in particular to a preparation formula and a method of an air-oxidized single-agent hair dyeing product, and belongs to the technical field of hair dyeing.
Background
Oxidative or permanent hair coloring products predominate in the modern hair coloring product market. The product can effectively cover white hair and change the color of hair. Oxidative hair dye products generally consist of two doses. One is an alkaline component containing a dye precursor and the other is a developer containing active oxygen, typically hydrogen peroxide. The hair dyeing needs to mix the two doses according to the operation instruction proportion and immediately and uniformly apply the mixture to the hair. The pH value after mixing is still alkaline, under the alkaline condition, the hair and hair scales are temporarily opened, the dye precursor permeates into the hair layer through the hair scales, oxidation, coupling and condensation reactions are carried out to form large dye molecules, and when the reactions occur, the melanin and hydrogen peroxide in the hair are subjected to oxidation reaction and fade, the hair scales stay on the hair for a certain time and are washed clean, the hair scales are closed, and the color can be permanently changed. Therefore, the oxidizing agent such as hydrogen peroxide plays roles in promoting the oxidation reaction of the intermediate and lightening the color in the hair dyeing process.
In the hair dyeing crowd, a great part of the complaint of dyeing is that the hair is dyed from light to dark, such as gold hair, brown hair to black and white hair to black, the light hair color is not required to be extracted in the process, and only the hair dyeing intermediate is required to react into dark dye molecules, so that the purpose of covering the primary hair color is achieved. Because of the irritation of the scalp by oxidizing agents such as hydrogen peroxide, which damage the hair, there are already some shallow and deep oxidative hair dyeing products on the market which use air as the oxidizing agent. Such products are primarily supplemented with air-sensitive dye precursor actives such as 1,2, 4-Trihydroxyphenol (THB), or 5, 6-dihydroxyindole. The just man series proposed by the American kem company is a product which uses THB as a main efficacy raw material and is compounded with a traditional oxidation type hair dyeing intermediate. However, since THB is potentially allergic, it is listed as a forbidden raw material in cosmetic regulations in our country for safety reasons, and this type of product is recovered in europe and the united states also before 2022 summer [1]. In the natural hair dyeing product of the Japanese flower king company, 5, 6-dihydroxyindole is used as a main efficacy raw material, the raw material is a natural melanin precursor, but the raw material is too sensitive to air, is not easy to store, is too fast to react with the air after being smeared on the hair, and often needs to be reused, the ideal result is difficult to achieve for 1 time, the color is also difficult to last, the dihydroxyindole is high in price, and the popularization of the product is limited by the defects.
Disclosure of Invention
The invention aims to provide a preparation formula and a preparation method of an air oxidation single-dose hair dye product, which are used for solving the problems in the background art.
In order to achieve the above purpose, the present invention provides the following technical solutions: the preparation formula of the air oxidation single-dose hair dye product comprises the following components in parts by weight: the polyamino substituted pyrimidine ring compound accounts for 0.05 to 2.5 percent; the water-soluble metal salt is used as a catalyst, and the ratio of the water-soluble metal salt to the catalyst is 0-2%; an oxidative hair dyeing intermediate accounting for 0.1-5 percent; an oxidative hair dye coupler in an amount of 0.1-5%; extracting antioxidant and allergy relieving agent from plants with a ratio of 0.5-5%; 0.1-2% of water-soluble anionic polymer; an alkaline pH adjustor for adjusting pH to 9 to 11; a water-soluble surfactant in an amount of 1-5%; the water-soluble solvent accounts for 1-5%.
As a preferable technical scheme of the invention, the polyamino substituted pyrimidine ring compound is a tetraamino substituted pyrimidine ring compound, and the addition amount of the 2,3,4, 6-tetraamino pyrimidine is 0.05-5%, preferably 0.05-2.5%.
As a preferable technical scheme of the invention, the metal salt catalyst comprises one or more of divalent manganese salt, divalent ferric salt, trivalent ferric salt and silver salt, and the addition amount is 0-5%, preferably 0-2%.
As a preferable technical scheme of the invention, the oxidative hair dyeing intermediate comprises one or more of p-phenylenediamine and salts thereof, toluene-2, 5-diamine and salts thereof, N-2-hydroxyethyl p-phenylenediamine sulfate, p-aminophenol and 4-amino-m-cresol, and the addition amount is 0.1-6%, preferably 0.1-5%.
As a preferred embodiment of the invention, the oxidative hair dye coupler must contain at least one or more electron-rich structural couplers, the-X group is one of hydroxyl and amino, the-Y group is one of hydroxyl and amino, the-Z group is one of methyl, ethyl and short-chain ether, at least one other conventional coupler is used for assisting in coloring, resorcinol and m-aminophenol are added in an amount of 0-5%, preferably 0.1-3%.
As a preferable technical scheme of the invention, the plant extraction antioxidant and the allergy relieving agent can be plant extracts containing flavonoids, polyphenols and terpenes, and can be powder and water agents, the adding amount is 0.1-6%, and the preferable adding amount is 0.5-5%.
As a preferable technical scheme of the invention, the addition amount of the water-soluble anionic polymer is 0.1-2%; the addition amount of the water-soluble surfactant is 1-5%.
As a preferred embodiment of the present invention, the alkaline pH adjuster is one of an organic base and an inorganic weak base, and adjusts the pH to 9 to 11, preferably to 9 to 10.5.
As a preferable technical scheme of the invention, the water-soluble solvent is one of alcohol, propylene glycol, glycerol and ethoxydiglycol, and the addition amount is 0.5-10%, preferably 1-5%.
As a preferred technical scheme of the invention, the preparation method of the single-dose hair dye product by air oxidation comprises the following steps:
s1: adding hot water into a main pot, dispersing a water-soluble anionic polymer into 80-DEG C hot water, fully swelling, homogenizing and uniformly stirring, adding a water-soluble surfactant, uniformly stirring, and cooling to 50 ℃;
s2: dissolving dye precursors including polyaminopyrimidine ring compound, oxidative dyeing intermediate and coupling body, water-soluble solvent, catalyst and plant extract in 60 deg.C hot water in a proper container, adding into main pot after dissolving to clarify, stirring, and cooling to 45 deg.C;
s3: adding perfume and antiseptic, and stirring to obtain the air oxidized single-agent hair dyeing product.
Compared with the prior art, the invention has the beneficial effects that:
1. the invention relates to a preparation formula and a method of an air oxidation single-dose hair dyeing product, which utilize an oxidative dye precursor sensitive to air, under the action of air, the air oxidation single-dose hair dyeing product can achieve ideal white hair coverage rate without being mixed with a traditional oxidant, simplifies packaging, is convenient to operate, can reduce the irritation of the oxidant to scalp in the hair dyeing process, is easy to realize commercialization, can achieve ideal color deposition (light hair dyeing depth and white hair coverage) by simply combing on the hair for 30-50 minutes, has color durability comparable to or even better than the effect of the two-dose products of the same type, and is milder because the oxidant except air is not needed, and the damage to the scalp and the hair in the hair dyeing process is greatly reduced.
Drawings
FIG. 1 is a schematic molecular diagram of a 2,3,4, 6-tetraaminopyrimidine of the present invention;
FIG. 2 is a schematic diagram of a coupler molecule according to the present invention;
FIG. 3 is a schematic diagram of the table of examples 1-4 of the present invention.
Detailed Description
The following description of the embodiments of the present invention will be made clearly and completely with reference to the accompanying drawings, in which it is apparent that the embodiments described are only some embodiments of the present invention, but not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
Referring to fig. 1-3, the invention provides a preparation formula and a method for an air oxidation single-dose hair dye product, which comprises the following technical scheme:
the weight ratio of the added components is as follows: the polyamino substituted pyrimidine ring compound accounts for 0.05 to 2.5 percent; the water-soluble metal salt is used as a catalyst, and the ratio of the water-soluble metal salt to the catalyst is 0-2%; an oxidative hair dyeing intermediate accounting for 0.1-5 percent; an oxidative hair dye coupler in an amount of 0.1-5%; extracting antioxidant and allergy relieving agent from plants with a ratio of 0.5-5%; 0.1-2% of water-soluble anionic polymer; an alkaline pH adjustor for adjusting pH to 9 to 11; a water-soluble surfactant in an amount of 1-5%; the water-soluble solvent accounts for 1-5%.
In order to achieve the white hair coverage effect of the commercially available common double-agent hair dye in the traditional hair dyeing operation time, electron-rich polyphenol or polyamino dye precursors sensitive to air are required to be added into the formula of the single-agent hair dyeing product by utilizing air oxidation, and the dye precursors of the phloroglucinol are listed as forbidden raw materials in national regulations to influence the commercialized application of the dye precursors, the polyamino substituted pyrimidine ring compound can be a tetramino substituted pyrimidine ring compound, and the structure of the polyamino substituted pyrimidine ring compound is shown in the figure 1, and 2,3,4, 6-tetraminopyrimidine. The commercial 2,3,4, 6-tetraaminopyrimidine is in a sulfate structure, and the substance is easy to react with a dye coupling agent and can be carried out in air. The addition amount is 0.05-5%, preferably 0.05-2.5%.
To further enhance color deposition, a water-soluble metal salt catalyst is added to the formulation to catalyze the oxidation of the dye intermediate in the hair. The water-soluble metal salt catalyst comprises one or more of divalent manganese salt, divalent or trivalent ferric salt and silver salt, and the anionic group can be nontoxic sulfuric acid ion, chloride ion, nitrate ion, carbonate ion, phosphate ion or organic acid such as fumarate, citrate, tartrate and the like. The water-soluble divalent manganese salt is preferably added in an amount of 0 to 2%, more preferably 0.1 to 1%.
An oxidative hair dyeing intermediate comprising one or more of p-phenylenediamine and salts thereof, toluene-2, 5-diamine and salts thereof, N, N-bis (2-hydroxyethyl) p-phenylenediamine sulfate, p-aminophenol, 4-amino-m-cresol and the like, wherein the addition amount is 0.1 to 6% according to the required target color, preferably 0.1 to 5%;
oxidative hair dye couplers must contain at least one or more electron-rich structural couplers, the structure of which is shown in figure 2, -X groups are hydroxyl or amino, -Y groups can be hydroxyl or amino, -Z groups can be methyl, ethyl, or short chain alkyl ether groups or other electron donating substituents. Preferably, it may be 2, 4-diaminophenoxyethanol hydrochloride or sulfate, 2-hydroxy-4-aminotoluene, 2-amino-4-hydroxyethylamino anisole, more preferably, it may be 2, 4-diaminophenoxyethanol hydrochloride or sulfate, and the amount of 2-hydroxy-4-aminotoluene added may vary from 0.1 to 3% depending on the desired target color. The formula can be added with other conventional coupling agents for assisting in coloring, such as resorcinol, 4-chlororesorcinol, 2-methylresorcinol, m-aminophenol, 1-naphthol, 1-5-dinaphthol, 2, 7-dinaphthol, 2, 6-diaminopyridine and the like, and the addition amount can be varied from 0.1 to 3 percent according to the required target color.
To achieve the shelf life of a commercially available product, a small amount of antioxidant needs to be added. However, the addition of conventional antioxidants, such as sodium sulfite and sodium ascorbate, greatly affects the coloring effect of the product. Through multipartite screening by the inventor, the plant antioxidant selected by the invention can play a role in stabilizing dye intermediates, but does not influence the coloring effect of products, and the plant antioxidant can be plant extracts containing flavonoid, polyphenol and terpene active substances, and can be powder or water agents, such as polygonum multiflorum extract, ginseng extract, purslane extract, karaoke extract and the like. And tested, the antioxidant not only plays a role in stabilizing, but also has a allergy-relieving effect, even can promote coloring, and the addition amount is 0.1-6%, preferably 0.5-5%.
In order to facilitate combing and application, and to stay on the hair for a certain period of time without dripping, hair dyes are generally required to have a certain consistency. Aqueous thickening systems are more advantageous for product application and penetration than emulsifying systems, and therefore require the addition of a certain amount of water-soluble polymer, preferably a water-soluble anionic polymer, for thickening purposes. The water-soluble anionic polymer can be xanthan gum, carbomer and other thickening agents which do not affect the coloring, and the addition amount can be 0.1-2% according to the required consistencies, which are generally 3000-20000 mpas.
When the pH value is in alkaline condition, the hair scales of the hair can be opened, and the micromolecular dye intermediate can be oxidized, coupled and condensed in the hair layer to form macromolecular dye molecules, so that the purpose of lasting color locking is achieved. The invention needs to add alkaline pH regulator to adjust the product to alkaline. The basic pH adjustor can be an organic base such as ethanolamine, isopropanolamine, or an inorganic weak base such as ammonium hydroxide, and adjusts the pH to 9-11, preferably to 9-10.5.
For fast wetting of the hair, a small amount of dense foam is produced, so that the hair can be fully contacted with air, a small amount of surfactant is required, and the water-soluble surfactant can be an anionic surfactant, such as sodium fatty alcohol ether sulfate, an amphoteric surfactant, such as cocamidopropyl betaine, or a nonionic surfactant, such as alkyl glucoside, in an amount of 1-5%.
A water-soluble solvent which is added in order to increase the solubility of the dye precursor and the permeability on hair, such as alcohol, isopropyl alcohol, propylene glycol, glycerin, ethoxydiglycol, etc., in an amount of 0.5 to 10%, preferably 1 to 5%, depending on the amount of the dye intermediate added.
The preparation method of the air oxidation single-dose hair dye product comprises the following steps:
the first step: adding hot water into a main pot, dispersing a polymer into the hot water (80 ℃), fully swelling, uniformly stirring, adding a surfactant, uniformly stirring, and cooling to 50 ℃;
and a second step of: dissolving dye precursors including oxidative hair dyeing intermediates and coupling bodies, solvents, catalysts and plant extracts in hot water (60 ℃) in a proper container, adding the mixture into a main pot, uniformly stirring, and cooling to 45 ℃;
and a third step of: adding perfume and antiseptic, and stirring to obtain the air oxidized single-agent hair dyeing product.
The components added in the formulas of examples 1-4 are shown in the table of figure 3, and the preparation method comprises the steps of adding hot water into a main pot, dispersing carbopol 940 into the hot water (80 ℃), fully swelling, uniformly stirring, adding a surfactant, uniformly stirring, and cooling to 50 ℃; dissolving dye precursors including oxidative hair dyeing intermediates and coupling bodies, solvents, catalysts and plant extracts in hot water (60 ℃) in a proper container, adding the mixture into a main pot, uniformly stirring, and cooling to 45 ℃; adding perfume and antiseptic, and stirring to obtain the single-agent hair dye product of examples 1-4.
The hair used for testing is the hair with 80% white hair rate of the people after washing and sun drying which are not dyed by the hair dye, and the white wool, and the two hair bundles are used as arbitration. The operation is that the products prepared in examples 1-4 are respectively and evenly smeared on wool and white hair of people, stay for 30 minutes, wash hair dye on hair by flushing, wash shampoo, dry by blowing the wind barrel with cold air. The result of dyeing is shown in the table of figure 3.
In fig. 3:
a. the product name of the carbopol sold by the Lubo company is940。
b. Glucoside surfactant sold by basf limited under the trade name2000UP。
Although embodiments of the present invention have been shown and described, it will be understood by those skilled in the art that various changes, modifications, substitutions and alterations can be made therein without departing from the principles and spirit of the invention, the scope of which is defined in the appended claims and their equivalents.

Claims (10)

1. The preparation formula of the air oxidation single-dose hair dye product is characterized by comprising the following components in parts by weight: the polyamino substituted pyrimidine ring compound accounts for 0.05 to 2.5 percent; the water-soluble metal salt is used as a catalyst, and the ratio of the water-soluble metal salt to the catalyst is 0-2%; an oxidative hair dyeing intermediate accounting for 0.1-5 percent; an oxidative hair dye coupler in an amount of 0.1-5%; extracting antioxidant and allergy relieving agent from plants with a ratio of 0.5-5%; 0.1-2% of water-soluble anionic polymer; an alkaline pH adjustor for adjusting pH to 9 to 11; a water-soluble surfactant in an amount of 1-5%; the water-soluble solvent accounts for 1-5%.
2. A formulation for preparing an air-oxidized single-dose hair dye product according to claim 1, wherein: the polyamino substituted pyrimidine ring compound is tetraamino substituted pyrimidine ring compound, and the addition amount of 2,3,4, 6-tetraamino pyrimidine is 0.05-5%, preferably 0.05-2.5%.
3. A formulation for preparing an air-oxidized single-dose hair dye product according to claim 1, wherein: the metal salt catalyst comprises one or more of divalent manganese salt, divalent ferric salt, trivalent ferric salt and silver salt, and the addition amount is 0-5%, preferably 0-2%.
4. A formulation for preparing an air-oxidized single-dose hair dye product according to claim 1, wherein: the oxidative hair dyeing intermediate comprises one or more of p-phenylenediamine and salts thereof, toluene-2, 5-diamine and salts thereof, N-2-hydroxyethyl p-phenylenediamine sulfate, p-aminophenol and 4-amino-m-cresol, and the addition amount is 0.1-6%, preferably 0.1-5%.
5. A formulation for preparing an air-oxidized single-dose hair dye product according to claim 1, wherein: the oxidative hair dye coupler must contain at least one or more electron-rich structural couplers, the-X group is one of hydroxyl and amino groups, the-Y group can be hydroxyl and amino groups, the-Z group can be one of methyl, ethyl and short-chain ether groups, and at least one other conventional coupler for assisting in coloring, resorcinol and m-aminophenol can be added in an amount of 0-5%, preferably 0.1-3%.
6. A formulation for preparing an air-oxidized single-dose hair dye product according to claim 1, wherein: the plant extract antioxidant and the allergy relieving agent can be plant extracts containing flavonoids, polyphenols and terpenes, and can be powder and water agent, and the addition amount is 0.1-6%, preferably 0.5-5%.
7. A formulation for preparing an air-oxidized single-dose hair dye product according to claim 1, wherein: the addition amount of the water-soluble anionic polymer is 0.1-2%; the addition amount of the water-soluble surfactant is 1-5%.
8. A formulation for preparing an air-oxidized single-dose hair dye product according to claim 1, wherein: the alkaline pH regulator is one of an organic base and an inorganic weak base, and the pH is regulated to 9-11, preferably 9-10.5.
9. A formulation for preparing an air-oxidized single-dose hair dye product according to claim 1, wherein: the water-soluble solvent is one of alcohol, propylene glycol, glycerol and ethoxydiglycol, and the addition amount is 0.5-10%, preferably 1-5%.
10. A method for preparing an air-oxidized single-dose hair dye product, which is characterized by comprising the following steps:
s1: adding hot water into a main pot, dispersing a water-soluble anionic polymer into hot water at 80 ℃, fully swelling, homogenizing and uniformly stirring, adding a water-soluble surfactant, uniformly stirring, and cooling to 50 ℃;
s2: dissolving dye precursors including polyaminopyrimidine ring compound, oxidative dyeing intermediate and coupling body, water-soluble solvent, catalyst and plant extract in 60 deg.c hot water in proper container, adding into main pot after dissolving to clear, stirring, and cooling to 45 deg.c;
s3: adding perfume and antiseptic, and stirring to obtain the air oxidized single-agent hair dyeing product.
CN202210521173.2A 2022-05-13 2022-05-13 Preparation formula and method of air-oxidized single-agent hair dyeing product Pending CN116763672A (en)

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101528310A (en) * 2006-08-10 2009-09-09 库姆公司 A catalyzed air oxidation haircolor
CN103006514A (en) * 2012-12-31 2013-04-03 周垂虎 Rapid vegetal hair dyeing agent integrating washing with dyeing
CN110638667A (en) * 2019-10-10 2020-01-03 广州市皇天日用品有限公司 Safe and stable single-agent hair dye and preparation method thereof

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101528310A (en) * 2006-08-10 2009-09-09 库姆公司 A catalyzed air oxidation haircolor
CN103006514A (en) * 2012-12-31 2013-04-03 周垂虎 Rapid vegetal hair dyeing agent integrating washing with dyeing
CN110638667A (en) * 2019-10-10 2020-01-03 广州市皇天日用品有限公司 Safe and stable single-agent hair dye and preparation method thereof

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
穆伟伟 等: "天然植物染发剂", 广州化工, vol. 43, no. 19, 8 October 2015 (2015-10-08), pages 8 - 12 *

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