CA2093478C

CA2093478C - Hair care products containing n-alkoxyalkylamides

Info

Publication number: CA2093478C
Application number: CA002093478A
Authority: CA
Inventors: Marvin E. Goldberg; Malti Bhambhani; Arthur Brandon
Original assignee: Revlon Consumer Products LLC
Current assignee: Revlon Consumer Products LLC
Priority date: 1992-07-24
Filing date: 1993-04-06
Publication date: 1997-10-07
Anticipated expiration: 2013-04-06
Also published as: EP0580453B1; ATE190223T1; DK0580453T3; AU656295B2; CA2093478A1; EP0580453A3; US5306489A; PT580453E; ES2145032T3; DE69327995D1; ZA933207B; AU3554593A; DE69327995T2; EP0580453A2

Abstract

A hair care composition comprising N-alkoxyalkylamides of the formula:

OH-CH2-(CHOH)

Description

2~93~78 HAIR CARE PRODUCTS CONTAINING N-ALKOXYALKYLAMIDES

Technical Field The invention relates to hair care compositions such as shampoo, hair conditioner, hair spray, and hair setting and styling compositions containing N-alkoxyalkylamides.
Backqround of the Invention Hair shampoos contain as active ingredients anionic detergents which foam and clean hair. While very effective in their function of cleansing, anionics can be harsh to the hair surface, leaving hair in an overly dry, unmanageable state.
Furthermore, the hair is rendered susceptible to electrostatic charge accumulation which promulgates the undesireable condition known as fly away hair. To mollify these adverse effects, it is the usual practice to incorporate selective ingredients into the shampoo formulation, other than those which contribute to product aesthetics. These selective mollifying additives, while effective in providing greater manageability and hair conditioning, unfortunately interfere with and reduce the anionic detergent's effectiveness in cleansing and foaming.
Hair conditioners and creme rinse preparations, on the other hand, employ cationic surfactants as their key ingredients. These materials, usually quaternary ammonium compounds, are substantive to the negatively charged --- 2093~7~

keratinaceous protein of hair. Because of their substantive properties, treatment of hair with a hair conditioner containing cationic quaternary ammonium compounds (generally after shampooing) provides the hair with a lubricating surface film which allows for easy combing. Hence, knots and tangles, encountered in hair combing after shampooing, are easily dissipated through hair treatment with a cationic hair conditioner. Notwithstanding their desirable characteristics, cationic hair conditioners formulated with quaternary ammonium compounds tend to overcondition the hair, making the hair undesirably heavy, "bodiless~' and unattractive in appearance.
Hair setting lotions and hair sprays are usually based upon polymeric resins which provide hair fixative effects.
Hair is given rigidity through application of these products enabling the hair to hold a style configuration in place.
Plasticizers are also formulated into the product which provide pliability to the films of the polymeric resin coating the hair. The plasticizers allow the resin film to bend, instead of rupturing or breaking under the stress of slight hair mo~ement. However, the total hair holding potential of the polymeric hair fixative is reduced when plasticizers are incorporated. As a result, the strength of the hair configuration is weakened and the hair style is shortlived.
We have now discovered that a small amount of a specific N-alkyoxyalkylamide, when incorporated with the key ingredients of a shampoo, cationic hair conditioner, or resinous hair fixative product provide a product with a ~ 2 ~ 9 3 ~ 7= ~

unique feel, lubricity, and sheen, without being greasy or heavy. In addition, treated hair is smoother, and easier to manage, has increased body, fullness, and softness. The N-alkyoxyamides of the invention are compatible with anionic surfactants, cationic surfactants, and polymeric resins in their respective formulation environment.
Summary of the Invention The present invention provides a hair care composition selected from the group consisting of:
a) a shampoo containing, by weight of the total composition, 1-45% cleansing surfactant, 1-55%
water, and 0.01-10% foam booster, b) a hair conditioner containing, by weight of the total composition, 10-95% water, 1.0-10% cationic surfactant or polymer, 0.1-10% conditioning agent, c) a hair spray cont~in;ng, by weight of the total composition, 0.5-10% resin, 0.01-5% neutralizer, 0.01-5% plasticizer, d) a hair mousse containing, by weight of the total composition, 0.1-10% hair fixative resin, 0.1-5%
conditioner, 0.05-5% foaming agent, and 1-50%
solvent, wherein said composition additionally contains 0.001-10% of a compound of the formula (Formula I):
O H
Il I
OH-cH2-(cHOH)p-c-N-(cnH2n)-o-(cmH2m+l) wherein p is a whole number from 1-4, (CnH2n) is a straight or branched chain alkyl bridge in which n is a whole number of 1 to 6, and (CmH2m+1) is a straight or branched chain alkyl radical in which m is a whole number of 1 to 6.
In another aspect of the present invention there is provided a method of enhancing the lubricity and sheen of hair comprising applying the above compositions to hair.

A

~ Z093~7=~

Description of the Drawings Figure 1: is a photograph at 5000X magnification of a brown hair tress which was shampooed ten times with a standard shampoo composition containing 5% methoxypropylgluconamide.
The brown hair tress shows build up of material on and between the cuticle layers of the tress.
Figure 2: is a photograph at 5000X magnification of a brown hair tress which was shampooed ten times with a standard shampoo composition without methoxypropylgluconamide. The 3a ~4 - 2093~78 tress does not show any build up of material on and between the cuticle layers as is seen on the tress in Figure 1.
Fiqure 3: is a photograph at 5000X magnification of a brown hair tress which was shampooed one time with a standard shampoo composition containing 5~~ methoxypropylgluconamide. A slight build up of material on and between the hair cuticle is seen.
Figure 4: is a photograph at SOOOX magnification of a brown hair tress which was shampooed one time with a standard shampoo composition without methoxypropylgluconamide. No build up of material is seen on the cuticle.
Fiqure 5: is a photograph at 5000X magnification of a bleached hair tress which was shampooed ten times with a standard shampoo composition containing 5% methoxypropylgluconamide. A
significant build up of material on and between the cuticles is evident.
Fiqure 6: is a photograph at 5000X magnification of a bleached hair tress which was shampooed ten times with a standard shampoo composition without methoxypropylgluconamide. No build up on and between the cuticles is seen in contrast to Figure 5.
Fiqure 7: is a photograph at 5000X magnification of a bleached hair tress which was shampooed one time with a standard shampoo composition containing 5% methoxypropylgluconamide. A slight build up of material is seen on and between the cuticles.
Fiqure 8: is a photograph at 5000X magnification of a bleached hair tress which was shampooed one time with a standard shampoo composition without methoxypropylgluconamide. In contrast to Figure 7, no build up of material is seen on and between the cuticles.

2893~78 Detailed Description The preferred hair care composition of the invention contains a compound of the formula (Formula II):

O H
., .
OH-cH2-(cHoH)p-c-N-(cnH2n)-o-(cmH2m+l) wherein p is a whole number from 1 to 4, (CnH2n) is a straight or branched chain alkyl bridge in which n is a whole number of 1 to 4, and is preferably 3, and (CmH2m+l) is a straight or branched chain alkyl radical in which m is a whole number of 1 to 4, and is preferably 1.
The most preferred compound of Formula II above is wherein p is 4, n is 3, and m is 1. This compound is methyoxy propyl gluconamide (hereinafter "MPG") as has the following formula (Formula III):
O H
III ~- -oH-cH2-(cHoH)4-c-N-(cH2)3-o-cH3 The term "hair care composition" means, in accordance with the invention, a shampoo, hairspray, gel, conditioner, mousse, or the like.
It is suggested that the hair care composition of the invention contain about .001-10% of the Formula I, II, or III
compounds, with .005-7% preferred and .005-5% preferred.
When the compounds of the invention are incorporated into shampoos, the resulting shampoo provides e~cellent lubricity, sheen, and manageability to hair without any greasy or heavy feel. The hair is also smoother and easier to manage, 2093~78 and has improved body, fullness, and softness.Generally suitable shampoo formulations comprise 1-45% anionic surfactant, and about 1-55% water. Additionally the shampoo may contain foam boosters, thickeners, chelating agents, preservatives, etc.
If foam boosters are added, generally .01-10% is suggested. Suitable foam boosters include cocamide MEA, cocamide DEA, lauramide DEA, capramide DEA, cetearyl alcohol, cetyl alcohol, cetyl betaine, cocamide MIPA, cocamidoethyl betaine, cocamidopropylamine oxide, cocamidopropyl betaine, cocamidopropyl hydroxysultaine, cocamide oxide, coconut alcohol, coco-sultaine, lauryl betaine, lauryl sultaine, lauryl alcohol, myristamide DEA, myristamide MEA, oleyl betaine, sodium sarcosinates, postassium coco hydrolyzed silk protein etc. are suitable.
A great variety of thickeners are suitable including cellulose derivatives such as hydroxyethyl cellulose, hydroxypropyl cellulose, C9_15 alcohols, Carbomers, guar gum, magnesium silicate, as well as various acrylic acid derivatives, PEG monostearates, etc. ~ range of 0.01-10% is suggested.
Generally about 0.001-1% preservative is suggested. The suitable preservatives are those used traditionally in shampoo or other hair care compositions.
It may be also desired to add a chelating agent which is capable of complexing with and inactivating metal ions to prevent adverse effects to the formulation. Generally about 0.001-1% chelating agent is suggested. Suitable chelating 20-93~78 agents are EDTA, HEDTA, TEA-EDTA, sodium metasilicate, sodium metaphosphate, sodium citrate, or mixtures thereof.
The compounds of Formula I, II, and III also provide excellent properties to hair when added to hair conditioning compositions. Generally, about 0.001-10% of the compounds of the invention will suffice, with 0.005-7~O preferred and 0.005-5% most preferred.
Suitable conditioning compositions comprise about 1.0-10% of a cationic polymer, 10-95% water, and 0.1-10% of a conditioning agent. Suitable cationic polymers include cationic quaternary ammonium compounds such as cetyl trimethyl ammonium chloride, cetrimonium chloride, stearylamidopropyl ethyldimonium ethosulfate, Polyquat 11, oleylamidopropyl amine oxide, guar hydroxypropyl trimonium chloride, trimethylsilylamodimethicone, stearyl dimethyl benzyl ammonium chloride, cetyl pyridinium chloride, dicetyl dimethyl ammonium chloride, or mixtures thereof.
Suitable conditioning agents include cetyl alcôhol, hydrolyzed collagen, stearamidopropyl dimethyl amine, wheat germ oil, silk protein, keratin amino acids, co_dimonium silk amino acids, panthenol, dimethicone, dimethicone copolyol, or mixtures thereof.
The conditioning agents may also contain emulsifiers, thickeners, acidulants, preservatives, fragrances, etc.
Emulsifiers are generally desireable and include ethoxylated cetyl/stearyl alcohol, cetearyl alcohol, etc.
About .01-5% emulsifier is suggested.

21)93~7~

Thickeners are also desireable and include cellulose derivatives, PPG-Buteth derivatives, etc. Generally .01-5%
thickener is suggested.
Acidulants may be added to keep the pH of the conditioner in the range of 2.5-6.0 Suitable acidulants are citric acid and the like, generally in a range of .001-1%.
The compounds of Formula I, II, and III also provide sheen, lubricity and softness to hair when used in hair sprays or hair fixative compositions. The Formula I, II, and III
compounds are generally added in amounts of 0.001-10%, with 0.005-7% preferred and 0.005-5% most preferred.
A suitable hair spray composition comprises 0.5-10%
resin, .001-5% resins, 0.01-5% neutralizers, 0.01-5%
plasticizers and about 15-40% solvent and, if desired, 5-60%
propellant.
Suitable resins include vinyl acetate/crotonic acid/vinyl neodecanoate copolymer, octyl acrylamide/acrylates/butyl amino ethyl methacryla~e copolymer, vinyl acetate/crotonic acid, polyvinylpyrollidone , polyvinyl pyrollidone vinyl acetate copolymer, PVP acrylates copol~mer, the ethyl ester of polyvinyl methylether/maleic anhydride, polyvinylpyrrolidone acetate, polymeric quaternary ammonium salts prepared by the reaction of ethyl methacrylate/abietylmethacrylate/diethylamino ethyl methacrylate copolymer with dimethyl sulfate, a polymeric quaternary ammonium salt prepared by the reaction of ethyl methacrylate/oleylmethacrylate/diethylamino ethyl methacrylate copolymer with dimethyl sulfate. Suitable neutralizers ~093~78 include amino methyl propanol, etc. Suitable plasticizers include ethyoxylated lanolin alcohols, C12 15 alcohols benzoate: glycerine, etc. Suitable solvents include isopropyl alcohol, anhydrous ethanol, or mixtures thereof.
The compounds of Formula I, II, and III may also be added to other hair fixative type compositions such as aerosol hair sprays, hair setting lotions and styling aids. Suitable hair setting lotions contain about 0.01-10% of hair fixative, 0.01-5% plasticizer, 20-70% solvent, or mixtures thereof.
Suitable hair fixatives include polyvinylpyrrolidone vinyl acetate, polyquaternium compounds, polyvinylpyrrolidone, or mixtures thereof. Suitable plastlcizers include glycerine, ethyoxylated lanolin alcohols, C12 15 alcohols benzoate, etc. Suitable solvents include methylene chloride, isopropyl alcohol, anhydrous ethanol or mixtures thereof.
The compounds of Formula I, II, and III may also be incorporated into mousse compositions. Suitable mousse compositions contain 0.1-10% of hair fixative, 0.1-5%
conditioner, 0.05-5% foaming agent, and 1-50% solvent. The hair fixatives, conditioners and foaming agents are as mentioned herein. Suitable foaming agents include octoxynol, etc.
The invention will be further described in connection with the following examples which are set forth for the purposes of illustration only.

3 4 ~ ~

Example 1 A hair spritzer was made according to the following formula:
w/w%
SD alcohol 40 B 80.00 AMP 0.71 Resin 28-2930 5.00 Amphomer 1.5 Dimethicone copolyol 0.30 Silk Protein 0.10 Cocamidopropyl Betaine 0.10 Water qs Fragrance 0-30 Methoxypropylgluconamide 0.10 Benzophenone 3 0.30 Example 2 A hair styling gel was made as follows:
w/w%
Water 74.21 Carbomer 940 17.00 Water 2.00 PVPK-30 4.80 Trieth2nolamine 0.60 Kathon C~* 0-04 DMDM Hydantoin 0.40 * denotes trade-mark 2093~78 PEG-75 Lanolin 0.50 PEG-75 Lanolin 0.50 Fragrance 0-03 Methyl paraben 0.10 PEG 40 hydrogenated Castor Oil 0.30 Hydrolyzed Silk 0.10 Panthenol 0.10 Benzophenone 4 0.05 Methoxypropylgluconamide 0.10 Example 3 A shampoo for dry and damaged hair was made as follows:
w/w%
Water qs Sodium Lauryl Ether Sulfate 14.00 Decyl Polyglucose 14.00 Lauramide DEA 3.00 Citric Acid 0.05 Methylparaben 0.10 Propylparaben 0.05 Guar Hydroxypropyltrimonium Chloride 0.30 Water 10.00 Glycol Stearate 1.70 Myristic Acid 0.20 Sodium Lauryl Ether Sulfate 10.00 Dimethicone Copolyol 0.20 -- ~ 2 ~ 7= ~

Glycerin 0.20 Trisodium HEDTA 0.23 Methoxypropylgluconamide 0.25 Kathon CG 0.09 Example 4 A hair fixative gel was made as follows:
w/w%
Water qs Polyvinylpyrrolidone ~ 4.00 Hydrolyzed Silk Protein 0.10 Water 35.00 Propylene Glycol 0.30 Methylparaben 0.10 Polyquat 11* 1.00 Polysorbate 20* 0.50 Kathon CG 0.04 Fragrance 0.30 Methoxypropylgluconamide 0.0001 ExamPle 5 A hair conditioner was made as follows:
w/w%
Water 72.18 Polyvinylpyrrolidone 1.00 Propylene glycol 2.00 .
Dicetylcimonium chloride 1.00 Octylmethoxy cinnamate 0.01 Hydroxyethyl cellulose 1.25 * denotes trade-mark 093 '~78 Fragrance 0.60 Water 20.00 Cetyl alcohol 0.50 Stearamido propyl stearamine 0.50 ceatearyl alcohol/ceteareth 202.00 Propyl paraben 0.02 Methyl paraben 0.10 Methyoxypropyl gluconamide (50%)0.25 Hydrolyzed Silk 0.10 Kathon CG 0.04 ExamPle 6 An aerosol hair spray was prepared according to the following formula:
w/w%
SD 40B alcohol QS
AMP 0.60 Vinyl acetate crotonic acid copolymer 5.000 Vinyl neodecanoate Polysorbate 80 0.200 Polysorbate 20, acetylated alcohol 0.100 PPG-20 Methyl glucose ether 0.070 Fragrance 0.200 Ethyl ester of hydrolyzed silk 0.100 Methoxypropyl gluconamide 0.050 About 70 parts of the above mixture was mixed with about 17 parts Dymel 152A and 13 parts of Hydrocarbon A17.

2093~78 Example 7 An aerosol hairspray was made as follows:
w/w%
SD 4OB alcohol QS
AMP 0.65 Vinyl acetate/crotonic acid 7.00 vinyl neodecanoate copolymer Fragrance 0.20 Ethyl ester of hydrolyzed silk 0.10 Water 25.00 Cyclomethicone 0.10 Methoxypropylgluconamide 0.05 About 70 parts of the above formulation was mixed with 10 parts of Hydrocarbon A31 and 20 parts of Dymel A.
Example 8 A shaving foam was made as follows:
w/w%
Water QS
Methylparaben 0.20 GLycerin 8.00 Allantoin 0.25 PVP 0.25 Dioctyl sodium sulfosuccinate 1.00 TEA (98%) 3.70 Palmitic acid 6.00 Stearic acid 2.00 Propylparaben 0.10 - 20931~7~

Lanolin oil 0.30 BHT 0.01 Jojoba oil 1.50 Water 2.00 Fragrance 1.00 Methoxypropylgluconamide 0.50 About 96 parts of the above formulation was mixed with 4 parts of hydrocarbon propellant.
Example 9 A shaving gel was made as follows:
w/w%
Water QS
FD~C Blue #l QS
Hydroxypropylcellulose 0.15 Sorbitol 6.00 Triethanolamine (98%) 8.00 Palmitic acid 10.00 Propylene glycol isostearate 3.00 Fragrance 0.50 Methoxypropylgluconamide 0.50 About 96 parts of the above formulation was mixed with 4 parts of hydrocarbon propellant.
ExamPle 10 A brushless shave cream was made as follows:
w/w%
Water QS
Polyquaternium 10 0.05 2~93~78 PEG 14M 0.2Q
Butylene glycol 2.50 Glycerin 3.00 Cocamido propyl betaine 4.00 Methyl paraben 0.35 Propyl paraben 0.20 Stearic acid 16.00 Glycol stearate 2.00 Phenyl trimethicone 2.50 Dimethicone 1.00 Sorbitan laurate 0.50 Polysorbate 20 2.00 Lanolin, isopropyl lanolate 7.00 TEA (98%) 1.60 Fragrance 0.50 Methoxypropylgluconamide 0.50 Example 11 Brown and bleached hair tresses were washed one time and ten times with a shampoo composition alone, and a shampoo composition to which 5% methoxypropylgluconamide was added.
The tresses were observed under the microscope at 5000X
magnification. As illustrated in Figures 1-8 supra, the tresses shampooed ten times with shampoo containing 5%
methoxypropylgluconamide exhibited a significant build up of material on the hair cuticle as compared to the hair tresses shampooed ten times with the same shampoo composition without methoxypropylgluconamide. Even the bleached and brown hair 2093~78 tresses which were shampooed only once with shampoo containing 5% methoxypropylgluconamide exhibited a build up of material which was not seen in the hair tresses shampooed with the same shampoo composition without methoxypropylgluconamide.
While the invention has been described in connection with the preferred embodiments it is intended to cover alternatives, modifications, and equivalents as may be included within the spirit and scope of the invention as defined by the appended claims.

Claims

1. A hair care composition selected from the group consisting of:
a) a shampoo containing, by weight of the total composition, 1-45% cleansing surfactant, 1-55% water, and 0.01-10% foam booster, b) a hair conditioner containing, by weight of the total composition, 10-95% water, 1.0-10% cationic surfactant or polymer, 0.1-10% conditioning agent, c) a hair spray containing, by weight of the total composition, 0.5-10% resin, 0.01-5% neutralizer, 0.01-5% plasticizer, d) a hair mousse containing, by weight of the total composition, 0.1-10% hair fixative resin, 0.1-5% conditioner, 0.05-5% foaming agent, and 1-50% solvent, wherein said composition additionally contains 0.001-10% of a compound of the formula (Formula I):

wherein p is a whole number from 1 to 4, (CnH2n) is a straight or branched chain alkyl bridge in which n is a whole number of 1 to 6, and (CmH2m+1) is a straight or branched chain alkyl radical in which m is a whole number of 1 to 6.

2. The composition of claim 1 wherein the hair care composition is a shampoo.

3. The composition of claim 2 wherein the Formula I compound n is 1 to 4 and m is 1 to 4.

4. The composition of claim 3 wherein the Formula I compound p is 4, n is 3, and m is 1.

5. The composition of claim 2 wherein the shampoo additionally contains one or more of 0.01-10%
thickener, 0.001-1% chelating agent, and 0.001-1% preservative, or mixtures thereof.

6. The composition of claim 1 which is a hair conditioner.

7. The composition of claim 6 wherein the Formula I compound n is 1 to 4 and m is 1 to 4.

8. The composition of claim 7 wherein the Formula I compound p is 4, n is 3, and m is 1.

9. The composition of claim 6 wherein the hair conditioner additionally contains one or more of 0.01-5% emulsifier, 0.01-5% thickener, and 0.001-1% acidulant.

10. The composition of claim 1 which is a hair spray.

11. The composition of claim 10 wherein the Formula I compound n is 1 to 4 and m is 1 to 4.

12. The composition of claim 11 wherein the Formula I compound p is 4, n is 3, and m is 1.

13. The composition of claim 10 wherein the hair spray additionally contains 5-60% propellant.

14. The composition of claim 1 which is a hair mousse.

15. The composition of claim 14 wherein the Formula I compound n is 1 to 4, and m is 1 to 4.

16. The composition of claim 15 wherein the Formula I compound p is 4, n is 3, and m is 1.

17. A method enhancing the lubricity and sheen of hair comprising applying to the hair the compositions of claim 1.