CA1298787C

CA1298787C - Compositions used in permanent alteration of hair color

Info

Publication number: CA1298787C
Application number: CA000548765A
Authority: CA
Inventors: Michael W. Helioff; Carmen D. Bires; Robert B. Login
Original assignee: GAF Corp
Current assignee: GAF Corp
Priority date: 1986-10-24
Filing date: 1987-10-07
Publication date: 1992-04-14
Anticipated expiration: 2009-04-14
Also published as: IL84085A0; AU597454B2; DK350488A; EP0288553A1; IL84085A; JPH01501003A; WO1988003017A1; NO882650L; DK350488D0; NO882650D0; AU8278587A; EP0288553A4

Abstract

COMPOSITIONS USED IN PERMANENT
ALTERATION OF HAIR COLOR

ABSTRACT
A permanent hair color altering composition comprising an aqueous preparation on the basis of melanin dissolution and/or oxidation of a hair colorant dye intermediate, which contains as a swelling and penetration agent, a quaternized amino lactam having the formula:

X-wherein m is an integer having a value of from 1 to 4; R is alkylene having from 3 to 8 carbon atoms and is optionally substituted with C1 to C4 alkyl; R1, R2 and R3 are each independently selected from the group of alkyl, alkoxyalkyl, hydroxyalkyl, alkoxy, aryl, aralkyl, alkaryl, and alkylamidoalkyl radicals, said groups each having from 1 to 30 carbon atoms and at least one of R1, R2 and R3 is a radical having from 8 to 30 carbon atoms; and X- is a chloride, bromide or iodide anion.
The invention also relates to the use of said quaternized compounds.

Description

COMPOSITIONS USEn IN P~RMAN~NT
ALTERA~ION OF H~IR COLOR

In one aspe~t the invention relates to an aqueous eomposition containing a stahle conditioninq, ~oftening and penetrating agent for hair undergoing treatment with a color alterlng formulation.
In another a~pect the invention relates to an agent which enhance~s the dissolution of melanin and promotes penetration of an oxi~ation dye interme~iate into a hair follicle.
In still another aspect the invention relates to an additive for a hair hleaching composition and, in yet another aspect an addltive for a permanent hair coloring shampoo composition.

BACKGROUND OF T~ INVENTIOM

The maln coloring component of hair is a dark pigment, melanin, which occurs as granules embedded in the hair cortex. The aim of bleaching is to ~ecolorize selectively the natural pigments or applied piqments in the hair with minimal damage to the hair matrix. ~en hair is bleached, the color changes to lighter and lighter shades depending upon the amount of melanin qranules dissolved and removed from the hair fiher. ~ydroqen peroxide is the leading solvent for melanin used in the bleaching process; however, along with melanin removal, the peroxide reacts with keratin to cause loss of tensile propertIes and damaae to the hair. More specifically, bleaching occurs in two steps: (1) initial soluhilization o~ the color granules, and (2) decolorization of the dark - brown ~olubilized pigment. The reaction hetween melano-protein and hydroqen peroxide is confined mainly to the protein-combined cyltene r~sidues which are .

1;~98787 ~'DN-1559 subsequently converted to comhined cysteic acid. The solubilization of the melanin granules is connecte~ with the splittlng of the disulfide bridges in the melano protein an~ lt is likely that the disulfide bridge may he the stabilizing factor in melanin, as it is in keratin~s.
The bleaching process can he halted at any point or can be permitted to continue to a light blonde or platinum shade. The latter provides a good hackground for a variety of tints which can be obtained by a subsequent coloring step. Such bleaching and coloring combination is known as a double process coloring and causes hair damage by promoting porosity, brittleness, loss of tensile strength and dryness.
Per~anent hair colorants lnvolve the use of oxidation dye intermediates which are colorless substances hut which, when mixed with oxidizing ag~nts just prior to use, produce color by a process of oxi~tive condensation. ~ore speciflcally, the Intermediates, in the presence of an oxidant, couple with another oxi~ation dye intermediate molecule to form a large fused ring color compound within the hair fiber. Since the fused ring product is too large to penetrate the hair fiber, it i~s essential that good penetration is achieved by the precursor intermediate. The oxidation dye process engenders many changes in the chemical and cosmetic characteristics of the hair which are undesirable.
Specifically, the effect of alka]i swellinq of the halr fiber leads to loss of tensile strength, flexibility and promotes a porous, dry appearance. Ad~itionally, the -oxidation dye intermediates often cause skin sensitivity and reddening. Still further, the color imnarted on processed hair is often non-uniform since the preprocessed sections, have higher porosity and absorh the interemediate at a faster rate than virign growth which is more resistant to ahsor~tion.

Certain quaternized amine compounds and Polymeric amines as disclosed in U.S. Patent ~,53~,127 and TJ.
Patent 4,579,732 have been developed to overcome some o~
the above problems. ~owever these hasic compoun~s have no~ heen found to be completely satisfactory since they react with anioni~ components which are commonly present in hair coloring or bleaching compositions. This reactivity causes undesirable a]terations in the sha~e desired. Additionally the amino groups react with hydrogen peroxide to form nitrogen oxi~es, thus increasing the effective amount of peroxide which must be employe~ in bleaching compositions. Since peroxides are known to have a drying effect on hair, it is desirahle to use as little as possihle to obtain the desired effect. Further the relatively high viscosity of the polymeric compounds together wlth the normal variation in molecular weight of the polymer chains in the product lea~ to formulation problems in reproducability of pro~uct quality and in storage of the product over extende~ periods. In ad~ition the large molecu1ar size of the polymeric products prevents their penetration into the hair fiber and instead forms a coating over the hair, which may ~evelop tack under conditions of hi~h humidity. Final]y, many hair ~ye and bleachlng compositions produce a disagreeahle odor which the prior quaternized amino compoun~s do not mask.
Accordingly, it is an ob~ect of this invention to overcome or minimize the ahove deficiencies hy providing a chemically stahle additive which obviates skin sensitization, condltions the hair durinq processing, aids in the penetration of dye intermediate without undue alkaline swelling of the hair fiber, provides complexing sites on which the colorant can form, minimizes the period of hair exposure to chemical solutions, provides a more I~ 129~787 _ 4 - 67369-479 uniform distribution of color to processed hair by promoting penetration in portions of new hair growth, preserves the tensile properties of bleached or dyed hair and successfully masks undesirable thiol odors.
These and other objects of the invention will become apparent from the following description and disclosure.
THE INVENTION
In accordance with the present invention there is provided a quaternized amino lactam which i9 incorporated in an effective amount into a permanent hair color altering formula-tion, preferably at a concentration of between about 0.01 to about 12 wt. %, most preferably between about 0.5 and about 7.5 wt. ~
based on total weight of the treating formulation. The lactams of the present invention are defined by the structure ~C=O l X_ ( I H ) +~ I ¦

wherein m is an integer having a value of from 1 to 4; R is alkylene having from 3 to 8 carbon atoms and is optionally substituted with Cl to C4 alkyl; Rl, R2 and R3 are each f A

- 12987~7 - 4a - 67369-479 independently selected from the group of alkyl, alkoxyalkyl, hydroxyalkyl, alkoxy, aryl, aralkyl, alkaryl, and alkylamidoalkyl radicals, said groups each having from 1 to 30 carbon atoms and at least one of Rl, R2 and R3 is a radical having from 8 to 30 carbon atoms; and X~ is a chloride, bromide or iodide anion, ,,'~

, preferably a chloride anion. Of these, lactams having the formula CH - _ CH
~ ~=o I + f 3 Cl are preferred and include those pyrrolldones wherein at least one of R2 and R3 is octaflecyl, hexadecyl, tetradecyl, hydrogenated ta~low or coco and wherein the other of R2 and R3 is methyl or the same as ~3.
~ost preferred are the pyrrolidones wherein R3 i9 hexadecyl or octadecyl which are employed in a concentration of between ahout 0.75 and ahout 5.0 wt. ~.
The present lactams pyrrolidones are heneficially incorporated into the color altering formulation just before use.
As "formulation" is used herein, it is to he understood that this term includes a cream, a gel, an emulsion or a watery liquid or detergent solution.
The present lactams can be used in~ivi~ually or ln admixtures and can he added to any of the commercial hair bleaching or oxidation dye intermediate formulations or compositions containing an oxidation dye intermediate including a permanent shampoo tint, a permanent hair dye, hair bleach, hair blanch or hair dye removal preparation for home or professional use. Alternatively, such color altering preparations may be made up using the components normally included in preparations currently marketed an~
the lactams of this invention added to improve properties and minlml~e hair dam~ge.

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lZ98787 Generally, the permanent hair dye formulations of this invention are those employed for changing the color of hair, covering up white hair, shading the hair after lightening or æimu]taneous bleaching and dyeing or ~ouble process blonding to provide color alteration of long color durability.
The permanent dye formulations of this invention conventionally include an oxidation dye intermediate such as an analog or a derivative of a phenylene diamine, an aminophenol, a phenol or naphthol which, upon oxi~ation couples with itself or another analog or derivative of phenylene diamine to form a large fused ring compound having at least one unæaturated chromophoric bond within the hair fiber. The color developed from the colorless intermediate depends on the substituents or terminal groups of the diamine, for example, such groups as an aromatic amine or pheno~, an aromatic nitro group or trace amounts of heavy metal. Other factors w'nich alter the shade of the dyed hair include concentration, alkaninity, base composition and the combination of intermediates involved ln the oxidation reaction. The dyeing or bleaching of hair generally requires from about l~ to about 40 minutes of processing time. T~se of the present lactams can reduce processing time by at least lO~. T~e following ,able I provides a representative group of dye intermediates, color couplers and modlfiers employed to obtain specific hair shades. Also, any of the dyes disclosed in U.S. Patent 4,532,127 are æuitably emptoye~
in this invention.

12987B~

~3 3 1"~, . . a ~3.

3~ j:8 r 3 j3 r gl333ii3j 3 1 ~33~!3~l33}~3 3 ~ 3 3~, 33~

3't 3 j ~ ~

~2987~7 Other compounds which act as color modifiers or couplers include m-diamines, m-amino phenol9, polyhydroxy phenols, which are also stabilizer~s and antioxi~ants, and naphthols. The later are often used as secondary ~ye intermedlates in the formulation. Pyridine derivatives have also been suggested for use as a dye intermediate in place of phenylene diamines. In some cases direct dyes can be added to the formulations to provide color highlights.
T~e color vehicle for the dye intermediates is employed at a pH usually between about 9 and 11 which can be adjusted with ammonium hydroxide to the desired level of alkalinity. The ammonium hydroxide base is preferred since ammonia assists in swelling the hair fiber and by being easily removed. More specifically, the color vehicle lS an aqueous solution of soap or synthetic detergent which provides wetting and penetration of the dye intermediate. Ammonium oleate, alkanol amides and shampoo detergents such as fatty alkyl sulfates, fatty acid polypeptide condensates and oxyethy1ated fatty alcohols are most commonly employed.
In addition to the dye intermediate an~ color vehicle, formulations may also include intereme~iate solubility aids such as propylene glycol, ethyl alcohol or isopropyl alcohol and conditioners such as glycerol, lanolin, oleyl alcohol, cetyl alcohol, etc. and antioxidants such as a sulfite, primarily sodium sulfite or bisulfite, and thioglycolic acid whic~ are usually included to prevent premature oxidation. The addition of the present lactams to this formulation obviates the need for other conditioners, promotes penetration of the intermediate into the hair fiber particularly in the areas of new growth, substantially reduces skin sensitization, promotes hair fiber swelling and results in a mare uniform lZ9878~

distribution of color while giving the hair a soft, silky, conditioned texture after processing. Also, the lactam moiety, particularly the pyrrolidonyl moiety of the present compounds, exsrts a stabilizing effect on the quaternized amino group so that the present compounds do not react with peroxides or anionic components. This stabilizing effect enabtes the use of smaller amounts of these components to achieve the desired effect.
Although the practical amount of lactam added to the formulation is within the range of from about O.OI to about 7.5 wt. ~ of the total formulation, it is to be understood that larger amounts, up to about l2 wt. ~ can be employed without deleterious effect, economics heing the limiting consideration.
T~e oxidation dye intermediate formulation is applied to the hair with a oxldation ~ye developer. The developer is an oxidant mixed with the intermediate formulation ~ust before application and is usually applied ln equal parts with the intermediate formulation; although when hydrogen peroxide is used as the developer, between about l.5 and about 2 parts peroxide per part of intermediate can be used to cause bleaching and coloring in a single application. Creams or aqueous solutions of 5 to 7~ hydrogen peroxide or urea peroxide are the primary i 25 developers commercially employed. Mowever other developers which have heen suggested include chloroates, persulfates, perborates and sodium dichromate. me lactams of this invention can also he added to the developer formultion for more uniform distrihution and/or thickening effect as in cream applications.
T~e above dye components are of ten formulated into shampoos with oleate soaps or ethoxylated fatty alcohols to prevent drip and run-off.

12~B787 The hair Aye operations may be followed by a final conAitioning treatment, a neutralizinq rinse or an acid balanced shampoo containing in addition to cationic or amphoteric surfactants, cation-active emollients. The present lactams may also be added to such neutralizing applications for conditioning effect.
Some typical hair dye formulations are illustrated by the followlng OXIDATION DYE IWTERMEDIATE

A. ASH BLONDE HAIR DYE

IngreAients ~ by Wt.
Oleic aciA 35.
Ethoxylated Sorbitan 10.00 Oleate (5 .~ole Ethoxylate) Soriban Oleate 3.50 PEG-40 Sorhitan Lanolate l.75 Lecithin Hydroxylated 1.25 EDTA (ethylene diamine tetra acetic aciA) 0.10 Sodium Sulfite 0.50 Deionized/Di~tilleA Water31.l9 Ammonium Hydroxide, 2~% lO.00 Isopropyl Alcohol 2.50 P-Phenylenediamine 0.60 O-Aminophenol 0.l0 P-Aminophenol 0.01 4-Nitro-1,2-Diaminobenzene 0.30 Pyrogallol 0.70 Resorcinol 0.20 Hy~roquinone 0.10 Perfume 0.20 N-n-Dodecyl Pyrrolidone 2.00 1 00. 00 12987~7 B. BLUE VIOLET RAIR DYE

Ingredlents ~ by Wt Oleic acid 35.00 Ethoxylated Sorbitan 10.00 Oleate (5 ~ole Ethoxylate) Soriban Oleate 3 PEG-40 Sorbitan Lanolate1 75 Lecithin Hydroxylated 1.?,5 EDTA (ethylene diamine tetra acetic acid) 0.10 Sodium Sulfite DeionizedjDistilled Water29 ~0 Ammonium Hydroxide, 28~10.00 Isopropyl Alcohol 2 50 P-Phenylenediamine 0 55 P-Aminophenol 0.90 l,5 Dihydroxy naphthalene0.80 2,4-Diaminoanisole Sulfate0.?5 Pyrocatachol 0.80 Perfume O . .~0 N-n-Dodecyl Pyrrolidone ?.. 00 i00.00 ,'' ., .

C. B1ACK HAIR DYE

Ingredlents % by Wt Oleic acid 35.00 Æthoxylated Sorbitan lO.OO
Oleate (5 Mole Ethoxylate) Soriban Oleate 3.50 PEG-40 Sorbitan Lanolate l.75 Lecithin Hydroxylated 1.25 EDTA (ethylene diamine tetra acetic acid) O.lO
Sodium Sulfite 0.50 neionized/Distilled l~later 2~.2~
Amwonium Hydroxide, 28~ lO.OO
Isopropyl A].cohol 2.50 P-Phenylenediamine 3.75 * 2,4-Diaminoanisole,l;
P-Phenylenediamine,2 0.05 l,5-Dihydroxy naphthalene 0.06 P-Aminodiphenylamine 0.05 Perfume n.20 N-n-Dodecyl Pyrrolidone 2.00 100.00 * fusion mixture~

~', . - -- .
- ~

129~87 D. MEDIUM RED HAIR DYE

Ingredlents ~ by Wt Oleic acid 35.00 Ethoxylated Sorbitan 10.00 Oleate (5 ~lole Ethoxylate) Soriban Oleate 3.50 PEG-40 Sorbitan Lanolate 1.75 Lecithin Hydroxylated 1.25 EDTA (ethylene diamine tetra acetic acid) 0.10 Sodium Sulfite 0.50 Deionized/Distilled Water23.25 Ammonium Hydroxide, 28% 10.00 Isopropyl Alcohol 2.50 2-Nitro-p-Phenylenediamine 2.50 4-Nitro-o-Phenylenedlamine 0.50 P-Phenylenediamine 1.00 P-Aminophenol 1.00 * 4-Nitro-o-Phenylenediamine,l;
2-Nitro-p-Phenylenediamine,l0.15 4-~mino-2-Nitrophenol l.50 Pyrogallol 2.0 Resorcinol 1.3 Perfume 0.20 N-n-Dodecyl Pyrrolidone 2.00 ~ 00. 00 * fusion mixtures -The same developer solution can he used for each of the above hair dyes. Thq following formu~ation is representative of a suitable developer.

Ingredient ~ by Wt.
Hydrogen Peroxide, 30~ 20.00 Nonoxynol-9 5.00 Nonoxynol-4 2.00 Phosphoric Acid 0.50 Cetyl Alcohol 0.50 Stearyl Alcohol 0.50 Deionized Water 71.50 1 00 . 00 If desired lactam can be adde~ to the above developing formu]ation instead of tO t~e dye formulation or the amount of lactam can be divided hetween both the dye and developer formulations. The concentration of lactam in dye and developer system can range between ahout 0.75~ and about 7.5~ by weight, preferably between ahout l~ and about 5% by weight.
Bleaching involves a process for partial or complete oxidative degradation of the natural color pigment, i.e. melanin granules mainly present in cortex of hair fiber, or removal of applied dye pigment in or on the hair. As a side reaction, hleaching also attacks the hair cuticle proteins, i.e. the keratin protein, and causes oxidative modifications o~ both the cuticle and cortex proteins: thus decolorizlng dissolved-melanin color granules and reducing the cross-linking capacity of cystine by oxldation to cysteic acid.

12987~7 The most common hleaching agent comprises an aqueous soltuion of hydrogen peroxide of between ahout 5 to 9~ strength in a formulation adjusted to a p~ of from about 9 to about 11, although urea ~eroxide and other hydrogen peroxide creams incorporating a thickening agent such as a fatty alcohol or an alkanolamide can also be used.
The peroxide bleaching agent is employed with an activator which is added just before use, ammonium hydroxide being preferred hy most practitioners since the ammonia swells the hair fiber to allow for peroxide penetration and is volatile which permits easy removal.
Other activators which have been employed include sodium carbonate and ethanolamines. Bleach accelerators and boosters such as persulfate salts of ammonia, potassium and sodlum may be used as ~ell and condltioners e.g.
ammonium oleate soap, a lipophilic surCactant~ cholesterol and lanolin derivatives, are generally included in the peroxide formulation. Notwithstanding the generous use of such condltioning agents, noticea~le drying, sptitting and texture loss to the hair occurs. Subse~uent reoxid3tion restores the cystine of most of the cysteine residues formed during reduction to disulfide bonds. Reported recoveries are approximately ~O~. Ctill, the bleaching process causes damage such as tangles, dryness, brittleness, greater porosity, swelling, frizzing, etc.
The present lactams can be added to these formulations in the above amounts to minimize skin sensitivity, to preserve the tensile properties of the hair and to provide a strong conditioning action by forming a thin film over the hair cuticle which eliminates or minimizes hair dryness and breakage. Also, hecause of their high penetrating power and hair swellin~ properties, the present lactams are capable of diminishing the time hair is exposed to the chemical oxidation process.

125~8787 FDN-155~

Some typical hair bleaching formulations include the following.

BLEACR FORMULATION A

Ingredient ~ by ~eight Polyethylene glyeol oleyl eth 14.02 Ethanol 7.01 Monoethanolamine 4.67 Ethoxylated nonyl phenol 2.80 2 2 50~ 2.33 K persulfate NH4 persulfat~ 2.95 Na persulfate Disodium EDTA
Na ~etasilicate 0.13 H2O 6.15 49.18 BLEAGH FORMUI.ATION B

Ingredient ~ by ~eiqht Cetyl Alcohol Glyceryl Monostearate and Polyethylene 2.50 Glycol 100 Stearate ~Arlacel 165~ 2 Deionized H2O
Hydrogen Peroxide, 35~ (dilution grade) 88.57 Phosphoric Acid, 10~ C.P. to pR 3.5 to 4.0 100.00 129~3787 ~LEACH FORMULATION C

(CR~AM FO~I) Ingredient ~ by Weight Cetyl Alcohol 10.00 Glyceryl Monostearate and Polyethylene Glycol 100 Stearate [Arlacel 165] 2.50 Deionized Water 70.36 Hydrogen Peroxide, 35~, (dilution grade) 17.14 Phosphoric Acid, 10% C.P. to pH 3.5 to 4.0 100.00 Other areas in the cosmetic color alteration of hair where the lactams of this invention can be applied include hair blanching which employs sulfur dioxide or potassium permanganate followed bv sodium thiosulfate to convert hair of mixed grey to snowy white an~ processes for certain hair dye removal techniques which employ a weak solution of sodium hydrosulfite, sodium thiosulfate or aminoiminomethane sulfinic acid.
The present lactams, particularly the 2~ pyrroli~ones, can he incorporated into any of the foregoing formulations simply by mixing in the prescribea amount, preferably just before use, at ambient temperature and pressure and mixed for a period sufficient to provide uniform distrihution.
Having thus generally described the invention, reference is now had to the following examples which illustrate preferred embodiments but which are not to be construed as limiting to the scope of the invention as more broadly set forth above and in the appended claims.

;

.
:
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EXAMPLE I

An evaluation of the quaternized lactam, ~imethyl octadecyl-~-(2- pyrrolidonyl)methyll ammonium chloride addltive in a standa~d type of hair bleach (Helene Curtis 5A White Frosting Bleach~ was made as described below.
Each of the representative compositions X and Y
comprising the hair bleach formulation were divided into equal portions. The first divided portions of X-Y were combined and immediately applied to portions of the hair selected for frosting on the left side of the scalp of the subject undergoing testing. The subject had (color) hair of good texture and quality. To the remaining divided X-Y
portions, after being combined, 1 wt. ~ of the quaternized dimethyl oct~decyl-~l- ( 2-pyrrolidonyl~methyl] ammonium chloride was added. The later mixture of combined X-Y
portions, containing the quaternized l~ctam, was applied to equal portions of the 'nair selected for frosting on the right side of the scalp of said subjec~.

a~ a~

- l9 -X. Ingredients in ~leach wt Polyoxyethylene glycol oleyl ether14.02 Citric acid 7.01 Ethyl alcohol 4.67 Monoethanol amine 2.80 Ethoxylated nonyl phenol 2.33 H22 (50%) 6.8g Potassium persulfate 2.95 Ammonium persulfate 0.92 Sodium persulfate 2.95 Disodium ethylenediamine tetra acetic acid 0.13 Sodium metasilicate 6.15 Deionized distilled water 4~.18 Y. Developer Wt. %

H22 (30~) 20.00 Nonoxynol-9 5.00 ~Jonoxynol-4 2.00 Phosphoric acid 0.50 Cetyl alcohol 0.50 Stearyl alcohol 0 50 Water 71.50 The combined lotions on each side of the scalp were separately maintained on the hair for the prescribe~
period, 30 minutes, after which the lotions were rinsed away with water. The hair was hlown dry and the following evaluations comparing the hair on the right and left si~e of the scalp were made. The results are reported in Table II.

lZ98787 -- ~0 --TABLE II
Left Side Riqht ,Side ~LEACHING PROCES~S
Ease of Application good excellent Processing Time 30 min. 30 min.
Scalp and Skin Irritation none none Ease of Rinse-Out good good WET EVALUATION OF HAI~
Feel fair excellent Dryness slight completely dryness conditioned Combability fair exce].lent Manageability good excellent Snarling some none Porosity slight none DRY EVALUATION OF HAIR
Combability f ~ ir excellent Snarling some none Degree of Bleach yellowvery pale yel.low Breakage none none Softness good better Body good excellent Manageability good excellent Conditloning smooth smoother Luster good excellent Color yellowvery pale yellow Blending (on hair shaft)fair excellent Coverage at ends fair excellent Llfting of color (pigmented hair) good excellent Color Retention good excellent Fading some very tittle Skin and Scalp Irritation none none FDN-1559129878~

-The quaternized lactam, dimethyl octadecyl-~N-(2-pyrrolldonyl)methyll ammonium chloride was also evaluated ~ as an addit~ve to a standard hair dye formulation namely ~ (Loving Care~- Medium Brown!. Each of the representative compositions A, B and C comprising the hair dye formulation were divided in equal portion~. The first dlvi~ed portions A-C were combine~ and immediately applied to the left side of the hair on the scalp of the subject undergoing testing. The subject had dark brown and grey hair of fine texture and quality. To the remaining divided portions A-C, after heing combined, 1 wt. ~ of the quaternized dimethyl octadecyl-~N-(2-pyrrolidonyl)methyl~
ammonium chloride was added. The later combined A-C
portion, containing tlle quaternized lactam, was applied to the hair on the right side of the scalp of said suhject.

fi~

A. Ingredients for Color Wt.

Water qs Tall oil acid 7.50 Propylene glycol 4.40 Iso C3 alcohol 4.35 Octoxynol-l 3.50 Nonoxynol-4 2.00 NH40H, 26 Baume 1.15 Ethoxydiglycol 0.75 Cocamide diethanolamlde 3.50 Polyethyleneglycol-8 tallow amine 0.50 Sulfated Castor Oil 1.50 Erythorbic Acid 0.50 Ethylenediaminetetraacetic acld 0.0l Glycol 0.25 Na sulfits 0-05 N,N-bis(2-hydroxyethyl)-p-phenylenediamine su~.fate 0.18 l-Naphthol 0.0 Resorcinol 0.3l p-Phenylenediamine 0.3~
Fragrance 0.50 Adjust pH to 9.8 B. Ingredlents for Developer Wt. ~

H202, 30% 20.00 Nonoxynol-9 5.00 Nonoxynol-4 2.00 Phosphoric Acid 0.50 Cetyl Alcohol 0-50 Stearyl Alcohol 0.50 Water 71.50 129878~

C. Ingredients in Condltioner Lotion Wt. ~

Hydroxyethyl Cellulose l.00 Ethoxydiglycol 0.50 Polyquaternium - 6 0.50 Cocoamphocar~oxypropionate 25.00 Cocamldopropyl ~etaine 10.00 Glycol 5-00 Quaternium - 15 0.25 Sorbic Acid 0.20 Phosphoric Acid to pH 3.0 Fragrance 0.20 Water qs The lotions on the hair on each side of the scalp were allowed to remaln for a period of 30 minutes, after which they were rinsed away with water. The hair was then shampooed and blown dry. The following evaluations comparing the hair on the right and left side of the scalp were made. The results of this evaluation are reported in Table III.

- ~4 _ TABLE III
Left Side Right Side HAIR COLORING PROCESS
Ease of Application good excellent Processing Time30 min. 30 min.
Skin and Scalp Irritationnone none Penetration good excellent Ease of Rinse-Out good good WET EVALUATION OF HAIR
Feel fair good Dryness dry fully conditioned Combability fair gooa Manageability fair good Snarling slight none Porosity slight none DRY EVALUATION OF HAIR
Combability fair good Snarling some none Coverage of grey good excellent Overall coverage good excellent Softness fair good Body fair excellent Manageahility fair excellent Conditioning li t t le very good ~5 Luster fair excellent . _ Tone at Roots lighter somewhat darker 81ending on Shaft fair good Coverage at ends good excellent Lifting of color (pigmented hair) good exceltent Color Retention (overall) good excellent Fading (overall) some none Skin and Scalp Irritation none none , 12g8787 Comparable results are obtained with the other lactams of this invention, particularly important are methyl didodecyl-rN-t2-pyrrolidonyl)methyl? chloride, methyl dihexadecyl-[N-(2-pyrrolidonyl)methyl? chlorlde, methyl dloctadecyl-~N-(2-pyrrolidonyl)methyl? chloride, dimethyl hexadecyl-r~T-(2-pyrrolidonyl)methyl] chloride, dimethyl tetradecyl-~N-(2-pyrrolidonyl)methyl? chlori~e, dimethyl octadecyl-~N-(2-pyrrolidonyl)methylJ chloride.

In a similar manner, between ahout 0.5 wt. ~ and about 7.5 wt. % of the lactams of this invention can be added to a conventional shampoo tint to improve dye penetration and dye reslstance to fading. As described, the lactam is added just prior to use.
Many other su~stitutions and modifications will become apparent from the foregoing disclosure without departing from the scope o~ this invention.

Claims

1. A permanent hair color altering composition containing a permanent hair color altering vehicle and an effective hair pene-trating amount of a penetrating agent of a quaternized amino lac-tam having the formula:

X-wherein m is an integer having a value of from 1 to 4; R is alky-lene having from 3 to 8 carbon atoms and is optionally substituted with C1 to C4 alkyl; R1, R2 and R3 are each independently selected from the group of alkyl, alkoxyalkyl, hydroxyalkyl, alkoxy, aryl, aralkyl, alkaryl, and alkylamidoalkyl radicals, said groups each having from 1 to 30 carbon atoms and at least one of R1, R2 and R3 is a radical having from 8 to 30 carbon atoms;
and X- is a chloride, bromide or iodide anion.

2. A composition of Claim 1 containing between about 0.5 wt. % and about 7.5 wt. % of said quaternized amino lactam.

3. A hair bleaching composition of Claim 1 containing between about 0.01 wt. % and about 12 wt. % of said quaternized amino lactam.

4. The hair bleaching composition of Claim 3 containing hydrogen peroxide and an ammonia containing activator.

5. The composition of Claim 4 wherein said composition is an aqueous solution.

6. The composition of Claim 4 wherein said composition is a cream.

7. A permanent hair coloring composition containing between about 0.01 wt. % and about 12 wt. % of the quaternized amino lactam of Claim 1.

8. The hair coloring composition of Claim 7 containing an oxidation dye as the hair coloring agent and an oxidizing agent.

9. The composition of Claim 8 wherein said composition is an aqueous solution.

10. The composition of Claim 8 wherein said composition is a cream.

11. The composition of Claim 8 formulated in a shampoo composition.

12. A permanent hair coloring composition comprising an alkaline solution of a phenylene diamine hair dyeing agent at pH of from 9 to 11, a peroxide containing oxidizing dye developer and an effective conditioning amount of the quaternized amino lactam of Claim 1.

13. The permanent hair color altering composition of Claim 1 wherein said lactam has the formula C1-wherein at least one of R2 and R3 is selected from the group consisting of octadecyl, tetradecyl, hexadecyl, hydrogenated tallow and coco and the other of R2 and R3 is methyl or the same as R3.

14. The process of applying to the hair a bleaching composition containing an effective hair conditioning amount of the quaternized amino lactam of Claim 1.

15. The process of Claim 14 wherein the effective amount of quaternized amino lactam is between about 0.5 and about 7.5 wt. %, based on total composition.

16. The process of Claim 14 wherein said quaternized amino lactam is added to said bleaching composition immediately before applying to the hair.

17. The process of applying to the hair a permanent hair coloring composition and an effective hair conditioning amount of the quaternized amino lactam of Claim 1.

18. The process of Claim 17 wherein the effective amount of quaternized amino lactam is between about 0.5 and about 7.5 wt. %, based on total composition.

19. The process of Claim 17 wherein said quaternized amino lactam is added to the hair coloring composition immediately before applying to the hair.

20. The process of Claim 19 wherein said permanent hair coloring composition consists essentially of a dye formulation and a developing formulation and wherein said quaternized amino lactam is added to at least one of said formulations prior to their mixture and application to hair.

21. The process of applying to the hair a shampoo tint containing an effective hair conditioning amount of the quaternized amino lactam of Claim 1.

22. The process of Claim 21 wherein said effective amount of quaternized amino lactam is between about 0.5 and about 7.5 wt. %, based on total composition.

23. The process of Claim 14 wherein m of the quaternized amino lactam has a value of 1.

24. The process of Claim 17 wherein m of the quaternized amino lactam has a value of 1.

25. The process of applying to the hair a bleaching composition containing an effective hair conditioning amount of the quaternized amino lactam of Claim 13.

26. The process of applying to the hair a permanent hair coloring composition and an effective hair conditioning amount of the quaternized amino lactam of Claim 13.

27. The process of Claim 26 wherein said permanent hair coloring composition consists essentially of a dye formulation and a developing formulation and wherein said quaternized amino lactam is added to at least one of said formulations prior to their mixture and application to hair.

28. The process of applying to the hair a shampoo tint containing an effective hair conditioning amount of the quaternized amino lactam of Claim 13.