JPS62205013A - Hair deformation treating agent - Google Patents

Abstract

PURPOSE:A hair deformation treating agent, obtained by blending a specific diepoxy ring-opened type dimercapto compound as a principal ingredient with other ingredients and capable of forming firm waves in the hair at a relatively low temperature in a relatively short time by simple operation. CONSTITUTION:A hair deformation treating agent, containing a compound expressed by the formula (n is an integer of 1-20, preferably 1-10; R is alkylene, substituted alkylene, phenylene, substituted phenylene, preferably 2-3C alkylene or substituted alkylene) as a principal ingredient and useful as the first solution of a two-bath cold permanent wave solution or heating type one- bath permanent wave solution. Since the above-mentioned treating agent has the above-mentioned effect and particularly no alkali agent or reducing substance and oxidizing substance in a high concentration are used in the heating type one-bath permanent wave solution, damage of the hair caused by elution of hair proteins can be reduced and the storage stability is good with slight irritancy to the skin.

Description

[Detailed description of the invention] [Industrial application field] The present invention relates to a novel hair deformation treatment agent.

[Conventional technology and its problems]

The most common way to give hair the desired wave is 1.
The first solution for Noq-Manent Wave, which contains reducing agents such as thioglycolic acid and cysteine as main ingredients, is used to reduce and open the SS bonds in hair and release the bonds between amino acid side chains. The bond is oxidized and closed using a second liquid for Q-manent wave, which is mainly composed of an oxidizing agent such as bromate, perborate, or hydrogen peroxide.1. This is a noq-manent wave method in which the wave is fixed by

As a reducing agent for the first liquid for this 9-manent wave,
Thioglycolic acid has traditionally been used in large amounts, but it has the drawbacks of being unpleasant to the user due to its bad odor, being highly irritating, and causing serious hair damage. A first solution using cysteine as a main ingredient instead of thioglycolic acid has been developed and is now in practical use.

However, although this has an improved odor compared to thioglycolic acid, it has a weak reducing power and cannot provide sufficient waves, and cysteine is easily oxidized in the air to produce cysteine, which is insoluble in water. There have been problems such as adhesion to the skin, impairing the appearance and feel, and causing skin irritation.

[Means for solving problems]

In such a situation, the present inventor conducted intensive research and found that the general formula (1) % formula % () (in the formula % n is an integer of 1 to 20, R is an alkyne Ts
, tlk-substituted alkylene group, phenylene group or substituted phenylene group) The present invention was completed by discovering that the xy ring-opening type zomerkadeto compound can form strong waves in a short period of time.

Therefore, one invention is Zoe? The present invention relates to a hair modification treatment agent containing a xylic ring-opening type zomercazoto compound 0) as a main component.

The compound represented by the formula (+) of the present invention can be prepared by reacting a diglycidyl ether derivative with sodium hydrosulfide in the presence of carbon disulfide and an alcohol, for example, according to the method of JP-A No. 55-59160, and acidifying the reaction solution. Manufactured by In the formula (seal), R particularly has 2 to 3 carbon atoms.
is preferably an alkylene group or a substituted alkylene group,
fl is particularly preferably from 1 to 10.

The hair deformation treatment agent of the present invention can be in the form of a cold two-bath type, an e-manent agent as the first liquid, or a warm-bath two-manent wave agent.

The two-bath type first liquid treatment agent is a ring-opened zomercazoto compound (dissolved in water to a concentration of 1 to 20%, preferably 2 to 10%), and adjusted to pH 4 to IIs using a buffer. Preferably, it is produced by adjusting the pf (7 to 9).The -temperature treatment agent contains 0.1 to 5.0%, preferably 0.1 to 5.0%, of the ring-opened zomercapto compound (1). is 0.
It is produced by dissolving it in water to a concentration of 5 to 3.0% and adjusting the pH to 6 to 10%, preferably 7 to 9, using a buffer.

Examples of buffering agents include citric acid/disodium hydrogen phosphate, hydrochloric acid/sodium parbital/sodium acetate, hydrochloric acid or maleic acid/trishydroxydiaminomethane, potassium dihydrogen phosphate or sodium dipotassium hydrogen phosphate. or sodium, hydrochloric acid or potassium dihydrogen phosphate or sodium/tetra, sodium borate, potassium or sodium dihydrogen phosphate/sodium or potassium hydroxide, hydrochloric acid/colicin, boric acid/sodium carbonate or sodium tetraborate, hydrochloric acid/ AminomethylzolonoQinzool, glycine/sodium or potassium hydroxide,
Examples include combinations of boric acid/sodium hydroxide, hydrochloric acid/sodium dimethylglycine, sodium bicarbonate/sodium carbonate, sodium tetraborate/sodium hydroxide, sodium bicarbonate/sodium hydroxide or water-soluble ammonium salt/ammonia. One of these is water-soluble ammonium salts, which cause less damage to the hair and less irritation to the skin.
A combination of ammonia and a water-soluble ammonium salt/basic amino acid such as arginine or lysine are preferred, and the water-soluble ammonium salt is preferably hydrochloride, carbonate or monobicarbonate. These buffering agents are incorporated in the processing agent of the present invention in a total amount of 0.05 to 10%, preferably 0.1 to 5%.

The hair deformation treatment agent rFi of the present invention uses the following (1) peptides or derivatives thereof, and (ii>divalent metal salts) for the purpose of improving wave forming effect 1 and preventing hair damage.

(i) It is preferable to use one type or two or more types of cationic or amphoteric gelamer.

(1) Peptide or its derivative ■Basic 7-minoril (e.g. lysine, arginine/)
A dimer or more peptide synthesized from one or two of
or a dimer or more peptide synthesized from one or two acidic amino acids (e.g. glutamic acid, asnoq-lagic acid); ■Keratin proteins from wool, 5 feathers, hooves, horns, etc.
, keratin hydrolyzate cationized product, albumin, globulin, Kong I described in JP-A-57-88111
A hydrolyzate produced by the method described in JP-A-57-85308 etc. as a decomposed derivative of l-cynin, casein protein or soybean protein; ■ Naturally occurring hormones or physiologically active peptides 1 such as insulin , oxidized glutathione, and the like. Among these, one having a molecular weight of 10,000 or less, preferably 5,000 or less? Lyrisone; hydrolyzate of keratin protein, soybean protein, etc.; insulin/ is particularly preferred.

These peptides or derivatives thereof may be used alone or in combination of two or more in an amount of 0.01 to 50% by weight (hereinafter simply expressed as %) in one hair modification treatment agent.

Preferably, it is blended in an amount of 0.1 to 10%.

(iil Divalent metal salt The following general formula % formula % (wherein A is B-", Ca", Zn" %Ni2+
and Mg 2+ cations selected from the group consisting of B
are F-, C1-, Br-, r, So"-, PO"-
, OH-, and CO2, and rII indicates the valence of B), or acetate, citrate of the divalent metal (A), Examples include organic acid salts such as lactate, succinate, and tartrate, and among these, acetates or chlorides of calcium, zinc, nickel, magnesium, and barium are particularly preferred.

These divalent metal salts may be used singly or in combination of two or more, and in the final use form, the metal ion is 10 to 50009P.
mm, preferably 100 to 1000 pprn.

(III) Cationic or amphoteric, t? The following compounds are water-soluble or are soluble in water in the presence of inorganic salts or organic salts, which are synthesized according to the description in Rimer JP-A No. 56-92812.

0) Copolymer of acidic vinyl monomer and basic vinyl monomer Typical example is acidic vinyl monomer or its salt 4
5 to 55 mol%, basic vinyl monomer or its salt 45 to
An amphoteric copolymer obtained by copolymerizing a monomer mixture consisting of 55 mol% at 150°C in the presence of a known radical polymerization initiator and in the presence or absence of a known promoter. can be mentioned.

The molar ratio referred to here refers to the case where each vinyl monomer has one acidic group or basic group in one molecule, and 1
In the case of monomers with multiple acidic or basic groups in the molecule.

The molar ratio is adjusted appropriately so that the net charge is approximately 0.

An acidic vinyl monomer is a compound having a vinyl group in one molecule that can be monopolymerized with an acidic group such as a carxyl group, a sulfonic acid group, or a phosphoric acid group, such as acrylic acid, methacrylic acid, or crotonic acid. , vinylbenzoic acid, 2-7crylamide 2-methylzolo/e sulfonic acid.

Styrene sulfonic acid, vinyl sulfonate/acid, allyl sulfonic acid, methallyl sulfone ff, 3-methacrylzolo, 4
7, unsaturated-basic acids such as sulfonic acid, and itaconic acid,
Examples include unsaturated dibasic acids such as maleic acid and fumaric acid, and monoesters of stiffness. Also.

Examples of their salts include sodium salts, potassium salts, ammonium salts, and the like.

A basic vinyl monomer has a primary amino group, 2
A compound having a basic group such as a primary amino group or a tertiary amino group and a polymerizable vinyl group, such as zomethylaminoethyl methacrylate, diethylaminoethyl methacrylate, dimethylaminoethyl acrylate,
Diethylaminoethyl acrylate.

Examples include zomethylaminoglobyl acrylate, zomethylaminoderobyl methacrylamide, zomethylaminoderobyl acrylamide, 2-vinylbilycine, 4-vinylpyricine, dimethyltorylamine, sialylmethylamine, and quaternized products thereof. Quaternary compounds include hydrides, methylates, ethyl compounds, etc., and the counter anion is a chlorine ion.

Examples include compounds such as halogen ions such as bromide ions, hydroxyl ions, and methyl sulfate groups.

2) Polymer of amphoteric monomer As a typical example, the amphoteric monomer represented by the general formula (1) is polymerized in the presence of a radical polymerization initiator at a temperature range of 20 to 120°C. ° Polymers can be mentioned.

(In formula (1), b R4s IIL? h rLa is a hydrogen atom or a methyl group * J s Rs is a methyl group or an ethyl group, human is 10- or -NH-, and X is -co□-
So.

or -PH03, where tn and n are integers of 1 to 3. ) The amphoteric monomer represented by general formula (I) can be synthesized by reacting a suitable aminoalkyl ester or aminoalkyl amide of acrylic acid or methacrylic acid with a lactone, sultone or cyclic phosphite.

These compounds include 1, for example, 3-dimethyl (methacroyloxyethyl) ammonium delononyl sulfonate, 3-zomethyl (methacroylamidopropyl)
Examples include ammonium sol, e-sulfonate, and the like.

The polymerization reaction can be carried out by conventionally known methods such as bulk polymerization, aqueous solution polymerization, reverse phase suspension polymerization, and precipitation polymerization, and can be carried out smoothly at a reaction temperature of 20 to 150°C in the presence of a radical polymerization initiator. It will be held in

Examples of radical polymerization initiators include sodium persulfate, potassium persulfate, ammonium persulfate, 2.2'-azobis(2-remizonoderonone) dihydrochloride, benzoyl peroxide, hydrogen peroxide, sodium peracetate, and hydroperoxide. Acid cumene.

Azobisisobutylnitrile and the like are used. The amount of the radical polymerization initiator to be used varies depending on its type, but it is generally preferred to use the radical polymerization initiator in an amount of about 0.01 to 5% by weight based on the total monomers.

Are these cationic or amphoteric? The amount of remer used alone or in combination of two or more is 0.01 to 20% by weight (hereinafter simply expressed as %) per hair deforming treatment agent.

It is preferably blended in an amount of 0.1 to 10%.

Furthermore, other conventionally known ingredients may be added to the hair deformation treatment agent of the present invention within a range that does not impede the effects of the present invention. Examples of other ingredients include higher alcohols, cationic and anionic surfactants, urea, silicone, aluminum stearate, aluminum compounds such as light bread, organic acids such as citric acid and malic acid, hydrochloric acid, etc. Inorganic acids such as ethylenecyamine, mono-, sea-, or tri-ethanolamine, basic pumino acids such as morpholine, arginine, and lysine, alkali agents such as ammonia and caustic soda, hair nourishing agents, bactericidal agents, colorants, fragrances, etc. It will be done.

When the hair deformation treatment agent of the present invention is used as the first liquid of a cold bath 2-Q-manent waving agent, it is carried out in a conventional manner using a commonly used second liquid. Warming-bath type) Q-My Wave agent and 1-,
When using it, the following method is used.

That is, first, a treatment agent is applied to one hair.

Before applying the treatment agent, the hair is wrapped around a ronde, curler, heatable hand-held setting device, etc.
It is desirable to form the desired waves L2, but if you want gentle waves, you can use a hair dryer or a brush to give the hair a normal blow finish. The amount of application varies depending on conditions such as heating temperature, but it is usually preferably 10 to 150 g per application. Next, the two hairs are subjected to VC addition at 40 to 160°C. What is the heating temperature and time?

The degree of hair damage and the type of peptide used.

Buffer type 5 PHt Treatment agent agent ff 1 K varies depending on the type of buffering agent, and high B treatment is advantageous for healthy hair that has not been treated with hair dye, bleach, etc., but hair damage due to heating Considering 40~1 (50℃, t¥!
It is preferable that f is 40 to 80°C. Also, use a cap to prevent moisture from evaporating from each hair during heating.

Further humidification is effective. The lower the temperature, the longer the heating time is required, but for the same reason, the heating time is preferably 30 minutes or less, and preferably between 3 and 10 minutes. On the other hand, for chemical treatments such as Q-ma, hair dye, and bleach, it is desirable to select milder treatment conditions.

〔Effect of the invention〕

Using the hair deformation treatment agent of the present invention, it is possible to form strong waves on the hair in a relatively short time with relatively low heating using a simple operation. Since it does not use reducing substances or oxidizing substances, it can reduce hair damage caused by the elution of hair proteins, and it is less irritating to the skin and has good storage stability. It has the advantage that various handling problems associated with the agent can also be solved.

〔Example〕

Next, the present invention will be described with reference to examples, but the present invention is not limited to these examples.

Example 1 A first solution of a cold and warm Q-manent wave agent having the composition shown in Table 1 was prepared, and the stability of the solution, the application of the 9-mer, and the feel after the e-mer treatment were evaluated. Table 2 shows the results.
Shown below.

Evaluation method [1] Stability After preparation, the solution was left sealed at room temperature for one week, and changes in the properties of the solution compared to immediately after production were observed.

(Evaluation criteria): ○...Transparent After soaking for 10 minutes at 30°C.

Rinse with water, then cold-warm, Q-manent wave agent 2nd solution (sodium bromate 5%, water 95%) V (
After soaking for 15 minutes at room temperature, the hair was rinsed with water, removed from the rond, and the formation of waves was visually evaluated.

(Evaluation criteria): O Slightly strong ○Normal ΔSlightly weak ×Weak (3) Feeling after NoQ-ma treatment (2) Regarding hair damage after e-ma treatment.

Evaluation was made based on the difference in feel from untreated hair.

(Evaluation criteria): Smoothness ○ Same as untreated hair △ Fairly bad × Poor; '1.1. Table 2 Example 2 A warm-warm type 9-manent wave agent having the composition shown in Table 3 was prepared, and its wave formation and wave holding power were investigated. The results are shown in Table 3.

[Measurement method] Wavy degree and wave holding power measurement test (10 healthy Japanese hairs from il15 were combined into a bundle, and a crow tube (diameter 1
0 mm), and place it in each treatment agent at 30℃ and 50℃.
℃ and 80°C for 20 minutes each. After rinsing thoroughly with water, the hair bundle is removed from the glass tube and becomes coiled. The length of the hair coil at this time was measured.

The wave degree was calculated from the following formula.

Wavy degree (e) > = -X 100-Y The sample was immersed in a 0.5% aqueous solution of sodium lauryl sulfate (VC) for 1 minute and then gently moved for cleaning. Next, rinse this thoroughly.

The length of the hair coil was measured again. Wave holding power is 1
The wave retention rate was evaluated using the following formula.

Wave temperature immediately after treatment Set the SH group concentration to be the same for each reducing agent** Soak in the first solution (7% thioglycolic acid, pH 9,0) for 10 minutes. ) for 10 min PH adjustment: 0.2M ammonium chloride/ammonia buffer Solvent: H8CH,C110HC1(,0(CI(,C
H4), CHICHO[ICf(, SH·rt-pronolinol 2% Example 3 The following warm-warm type Q-manent wave agent was prepared.

Prescription example I A 1tscu, 1cHouci+, o(cu, cu
,o),cI(,cuouctt,su 2.Oe/
JB keratin protein hydrolyzate (v0w630)
1.0C Stearyltrimethylammonium chloride 1.0D ? Lyoxyethylene lauryl ether (E, 0.23 mol) 1.0E Ammonium bicarbonate 3. OF Arginine
G fragrance adjusted to PH8.5
0.2 H ion exchange water Balance 100.0 Manufactured by dissolving Man, B, and E in ion exchange water, adding a solution in which C1DKG was dissolved, and finally adjusting p)I with F.

Prescription example 2 A H2O) [4I(0[(CH20(CI(2CHt
O)ocHtcHo)lclItsH1,5eQB Calcium Chloride 1. OC cetyltrimethylammonium chloride chloride 2. O.D.
Ammonium chloride 2.5E
Ammonia water (28%) p) H9.0
F fragrance Q, I G Ion-exchanged water Balance 100.0 Dissolve A, B, and D in ion-exchanged water, add a solution of F to C, and finally adjust the pH with E to produce.

Prescription example 3 ^f(SCH,CHOHCH,0(CH,C)1,0)
, CH, CHOIICH, Sf (2,0(ha)Cn-zorononol 20
．． OD Stearyltrimethylammonium chloride 2.0E Glycylg-11cin
3.5F Ricin
Adjust pH to 9.0 G fragrance 0.
2! (Ion exchange water balance 100.0 Dissolve B and E in ion exchange water, add a solution containing CKA, D and G, and finally adjust the pH with F to produce.

Prescription example 4 A H8CH,CHOHCH,0(C)(tCH,0)
, CH,CHOi(C)I,SH2,o('/JB dimethylaminoethyl methacrylate/acrylamide
0.5-2-methylzolo, Q sulfonic acid copolymer C sodium chloride 3. O.D.
Sunaryltrimethylammonium chloride
2. OE ammonium chloride
1. OF Ammonia water
G fragrance adjusted to pH 9.0
. , 2 H ion exchange water balance 100.0 Add ^, B, C, and E to the ion exchange water.

After dissolving, add the solution containing DKG, and finally adjust the pH with F.
Adjust and manufacture.

that's all

Claims (1)

[Claims] 1. The following general formula ▲ Numerical formula, chemical formula, table, etc. A hair deforming treatment agent containing a diepoxy ring-opened dimercapto compound represented by the following formula as a main component.