CA2025185A1 - Hair conditioners - Google Patents

Abstract

Abstract of the Disclosure The treatment of keratinaceous fibers to render them softer, more easily combed, shinier and more manageable is carried out using conditioning formulations which contain, as essential ingredients, a long chain amido alkyl amine, a long chain amine salt of a polymeric acid or a long chain amido alkyl amine salt of a polymeric acid, and an aminofunctional silicone polymer.

Description

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Backqround The ~onditioning, or surface modification, of human hair de$ends upan such factors as whether it has been chemically treated (ie., dy0d, per~ed, relaxed or the like) or physically abused (eg., combed while wet, overcombed, teased, rolled too tightly). Because of the v æ ying demands placed upon a conditiomn~ oomposition, it is difficult to find a formLlation which per~orms satisfactorily in all respects. For example, conditioners may be used on healthy halr to enhance wet and dry combing ease, shine, m~nag~hility and body or ful~ness. However, those which enhance combing ease have been known to leave the hair limp and with a "coated" fP~l.
The following patents refer to hair conditioning formLlations:
U.S. 4,374,825 refers to polydimethylsiloxanes with salts of fatty am mes (see col. 4) in hair conditioning compositions.
U.S. 4,529,586 shows a conditioner which contains an amcdimethicone polymer, a long chain fatty acid-based cationic emLlsifier and a cationic polymer.
U.S. 4,537,762 descrlh~c hair and skin conditioners which emplcy, as ingredients, quaternary ammonium cc~pc~nds and tertiary am m e salts of long chain acids.
U.S. 4,548,810 shows hair conditioning formulations which include long chain tertiary amine/long chaln acid reaction products (see cols. 1 and 2).

U.S. 4,72fi,s45 refers to hair rinse compositions which contain a lon~
chain amidoamune salts as emulsifiers (see the paragra p bridg mg 0015. 4 and 5).
All of these disclosures are hcreby incorporated by reference.
me Invention It has been disccvered that a novel ccmbination of three ingredients yields a conditioner which gives all of the desirable properties listed above at the same tIme, especially for chemically treated hair~-(ie., hair which has been dyed, permed, relaxed or the like).
In a preferred embodlment, 1.0 wt.~ linoleylamid~propyl dimethylamine is combined with 2.0 wt. % linoleylamidoprcpyl dimethylam m e dimer dilinoleate and 2.0 wt. % of an anuno-functional silicone polymer to yield a conditioner which ~npro~es ease of koth dry and wat combin~, hair feel (both dry and wet), and shine, body and manageability when dry.
A~vanta~es of the Invention Ihe conditioner of the Lnvention, whether used a3 a rinse-out or leave-in ccnditioner leaves hair softer, cleaner and more manageable than conventional shampoos and rinses. This is particularly true when the hair has been chemically treated befor~ use of the conditioner of the invention.
Surprislngly, the form~lations of the invention give the hair more body than formulations ccntaining quaternary or polymeric quaternary reagents ie., reagents which are known to in~rove bo~y.

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It is believed that the unique three-component combinations used m the invention--ie., comblnations of long chain alkylamidoamines, tertiary amlne salts of long chain ~atty acids and amino-f`unctional silicones unite synergistically to leave the hair easily ccmbed, whether wet or dry, and feeling soft and clean with excellent anti-static prcperties ~no "flyaway").
Lastly, the hair has significantly more body after the subject compositions are applied thereto.
These and other advantages of the invention will become apparent after a consideration of the followLng description and claims.

Description of the Invention Ih~ invention is cancerned with treatment compositions for keratinaceous fibers and to methods which emplay them.
~ he treatment compositions contain three key in~redients defined with CIFA namenclature. Cther reagents may be emplcyed in the composition, but they are generally cptional and need not be ll~PA.
Three Requlred Inqredients A. Lonq Chain Amldo Alkyl Amlne ~ h1~ cccpcrect comprises one or more cc=pc~nds conforming to formula I ~ - C( )~

wherein R is a C7_22 alXyl group, Rl is a Cl_10 alkylene linkage, and R2 and R3 are independently hydrogen or Cl_6 alkyl groups; _3_ Preferably, the ccmpcurds used are those in which R is a C18 moiety. R may be substituted, but is preferably a hy~rocarbon moiety, with one or more sites o~ unsaturation. R may be saturated.
The Rl linkage in ingredient (a) generally contains from 1 to 10 carbon atcmsO Preferably, it contains 2 to 6 carbon atoms, most preferably 2 to 4.
Ihe R2 and R3 substituents may be H or Cl_6 alkyl groups.
Preferably, they are the same group and contain from 1 to 3 carbon atoms. R2 and R3 groups contain mg 1 or 2 carbon atoms are highly preferred.
It is generally preferred that Rl, R2 and R3 nct ccntain any atoms okher than carbon and hydrogen.
Materials useful as ingredient (a) are l moleylamidcpropyl dimethylammR, oleylamidopropyl dimethylamine and stearamldoethyl diethylam1ne.
B. Long Chain Amine Salt or Lonq Chain Amido Alkyl Am~ne Salt of a Polymeric Acid qhis cccponcnt contalns cne or more ccrpound~ of fc~mula II or III:
oC~ R~ (Tr) Jrn ~-C~~ 1 R~ ~

wherein R, Rl, R2 and R3 h~ve the meanings given above; R4 is ioue of a ~ 4-68 polymeric acid znd m equals "n" and is 2 to 4.

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It is generally preferred that R4 be a dimer or trimer of a long chain fatty acid. Suitable R4 groups ar~ residues of such acids a oleic, linoleic and the like. Mixtures are operable.
Compcunds in which R~ is a dimer are preferred. In these compcunds m and n will bcth equal 2. In those cases where R4 is trimeric, m and n will be 3. While R4 may represent residues of acids which contain 4 acid groups, thÆse arc genrally less preferred.
In formLlas II and III, R, Rl, R2 and ~ have t~e same meanmgs given for formLla I, above. It is preferred that the R portion of the molecule be a C18 moiety.
Materials useful as ingredient (b) are: d1~Pthyl lauramlne d~mer dilinoleate, linoleylamidopropyl dimethylamine dimer dilinoleate, oleylamidopropyl dimethylamine dimer dilinoleate, and the like. Mixtures can be used.

C. ~minnfunctianal Silicone Polymer This comQcnent ccntains ane or re m~terials of fonm~la IV:

~1-0~Si (C~3)~ OlX- -- ,~s rP~ ~) ~H

_ ~
whexein ~ an~ ~ are independertly selected ~rom ~2-~6 s~
and br~nched-dhaln alkylene linkages, ~ is selected from H, Si(CH3)3 or Si(CH3)2oCH3, ~ is either OH or CH3, and x and y are such tha~ th~ molecNlar weight of polymer is from about 300 to about 500,000- -5-~J ~

In formula IV, it is genexally preferred that ~ and ~ be branched-or straight-chain C2_4 alkyl m~ieties~ It is highly preferrel that ~ be a -CH2CH2CH2- moiety or a -CH2CH(CH3)CH2 moiety while ~ is a C2 moiety, preferably -CH2CH2-. In a highly preferred embodlment, ~ is ~ CH(CH3)CH2-, R6 is ~ ~ , R7 is SilCH3)3 and ~ is CH3.

Materials useful as ~ ient (c) include Dow Co ~ 929 EmLlsion, Dcw Corning Q2-7224 Conditioning Agent, Genral Electric 176-12096, General Electric SM2059 and Ciba Gelgy Ultratex MES.
sitio~s The treatment compositions of the invention will genexally contain ingredients (a) thrcugh (c), as well as okher ingredients, in the am~unts set cut in Table 1.
I~ELE I

Wei~ht Per¢entaaes Inqredient Brcad Preferred Hiahly Ran~e Ranae Preferred a. Amine 0.1-3.0 0.5-1.5 0.8-1.2 b. Amine ~Alt of polymeric 0.1-4.0 0.5-2.5 1.5-2.5 acid c. Aminofunctional silicone polymer 0.1-4.0 0.5-2.5 1.5-2.5 d. EmLlsifiers 1.0-15.0 3.0-10.0 6.0-8.0 e. Preservatives 0.01-1.0 0.5-0.9 0.70-0.80 f. Other adjuNants 0.5-10.0 1.0-3.0 1.5-2.5 g. Water q.s. to 100 q.s. to 100 q.s. to 100.

Okher Inoredients As Iable 1 shcws, applicants envision the use of a variety of materials in the treatment compositions of the inNention~
Among the ingredients to be added are fixatives, em~lsifiers, preservatives, st~bilizers, solvents, dispersina agents, fragrances, colorants, fillers, and the like.

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Other adjuvants may be included. These would include bo~ying agents and rheological modifiers, such as the hydrcc~rbon polymer manufactured by Petrolite Specialty Polymer Grcup and sold under the trade name V~bar 825, mineral oil, petrolatum, paraffin wax, etc. N0utralizing agents, such as lactic acid, glycolic acid, citric acid, ~ oric acid or any acid typically used in hair care p ~ s may be e~ployed.
m e carrier for delivering the compositionæ of the present invention will generally be an aqueous vehicle. This may take any of a variety of forms, e.g. solutions, aqueous emLlsions, aqueous gels, and the like. As used herein, the term "aqueous carrie~' is Lntended to include situations in whi d wat~r is essentially the only material that constituties the vehicle, as well as those situa~ions in which the water is mixed with substantial quantities of other ingredients, e.g. solvents, thicXening agents, emLlsifying agents, gelling agents, etc.
Preparation of the ccmPositions ThR compositions of the invention are prep2red by using the techniques set out in the examples.

Use of the Compositions The compositions are generally applied aS pourable emulsicns. They may, however, be semi-solids, ie., gels, creams, or ointments.
While it is preferred that they be rinsed from the h31r after application, they may ke applied, eg., by spraying, to the hair and left to dry.
If used in aeroso~ produc~s, the ccmpositions of the invention may contain suitable amKunts of prcpellants, foaming agents, and the like to facilitate application.
The compositions may be applied to hair via one or more treat~ent steps. Gbnerally abcut 1-3 shampooings followed by about 1-2 rinses are operable.
Substrates While ~L~ and 'Ihuman hair" are mentioned throo3hcut the descripkion, it is cc~templated that the treatment cQmpc6itions will be used to treat a wide variety of keratinacecus substrates.
In general "living" hair, ie., on a mammalian or cther heaq~bcdy is contemplated. HcweNer, th~se compositicns may also be used on "non-living" substrates, such as wigs, doll's hair, fhr and the like.
Examples The follQwing examples are illustrative of the present invention. It is to be urderrtood, hcwever that the invention is ~t limited hereto.
Percentages are given in percent by weigh~, based cn tckal cc~positicn weight.

Example 1 wt.
Raw Material __ _ _ Pereent Cetearyl Alechol and Ceteareth - 20* 3.50 Cetyl Aleohol 2.00 Glyeeryl Tribehenate 2.00 Methyl paraben 0.10 Propyl paraben 0.05 Hydrrcarton polymer 2.00 stearoxy dimethicone 0.60 1,3~dimethylol-5,5-dimethyIhydantoin 0.30 2 phRnoxyethanol 0.30 Glyeolie Aeid 1.00 Ilnoleyla~idoprcpyl dimethylamme dimex dil moleate 2.00 Oleylamidcpropyl dimethylamme l.oo Fragranee 0.40 Amocimethicone, nonexynol 10 (and) tallowtrimonium chloride** 2.00 Deionized water 82.75 100 . 00 *Ratio of Ceteryl alcchol to Ceteareth-20 is 80:20.
**Ratio of silicone:noncxynol:chloride is 30:4:1.

In preparing the compositions of this inNention, ~he proce~=ral step3 are q~ite conwentional and typir~l of an oil-in-water em~lsion. Ihe o11 phase iB hRated to 60C - 65'C and added, with stirring, to the water phase at the same temperature.
The batch is muxed while being cooled. At 25-C - 35'C, the fragrance and silicone are added. After appropriate mixing, the batch is packaged.

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EXample 2 The composition of Example 2 is prepared in the sa~e manner as EXample wt.
Raw Material Percent Deionized water 85.048045 Methyl paraben 0.100000 Prcpyl paraben 0.050000 Stearamidoprcpyl dimethylamune 1.000000 Stearyl dimethylam me dimer ilinoleate2.000000 Trimethylsilylamodimethicone (an~) octoxynol 40 (and) isolaureth - 6 (and) glycol* 2.000000 FD~C Yellow #6 0.000475 FD~C Yellow #5 0.001480 Cetearyl alcchol (and) ceteareth-20 3.500000 Cetyl alcchol 1.000000 Glycol stearate 1.500000 Paraff m 2.000000 Mlneral Oil 1.000000 nM~M Hydantoin 0.300000 Phenoxyethanol 0.300000 Fragrance 0.200000 100.ooooo *The ratio of silicone:oc~oxynol:isolaureth:glycol is 30:4:2:1.
Ex~mple 3 The ccmpositicn of Example 3 is prepared in the same manner æ those of Examples 1 and 2 ~t.
Raw Material ~ _ Percent Ce~earyl Alcohol and Ccke~retn - 20* 3.50 Cetyl Alcchol 2.00 Glyceryl Tribehena~e 2.00 Mbthyl paraben 0.10 Pr3pyl paraben 0.05 Hydroc3rbcn polymer 2.00 Stearoxy dimethicone 0.60 1,3-dimethylol-5,5~dimethylhydantoin 0.30 2 phenoxyethanol 0.30 Lactic Acid 1.00 Linoleylamidcpropyl dimethylamine dimer dilinoleate 2.00 Llnleylamidcpropyl dLmethylam me 1.00 Fragrance 0.40 Trimethylsilylanodimethicone (and) octcxynol 40 (and) isolaureth-6 (and) glycol 2.00 Deionized ~ater 82.75 100. 00 Example 4 - Evaluations The composition of Example 3 was evalua~ed against a ccmmercial product which uses a conventional quaternary ~ um chloride as the active ingredient. The evaluatian was done on tinted hair, two weeks after the tin~ had been applied, with the compositian of Example 3 applied to onerhalf of the mcdbl's hQad and the commercial pro*uct to the other side. Ihe eNaluations were done by a panel of skilled beauticians.

In this ~valuation, fourteen models were treated. The parameters measured included: ease of combing, in bo~h the wet and dry stages: feel of the hair, in both the wet and dry stages;
and shine, body, and manageability in the dry stage.
It was found that the compositian of EXample 3 was clearly superior to the commercial product, as it had ketter wet ocmbing with the hair feeling softer and cleaner; better dry combing with the halr feeling softer and cleaner and with more body.
In a second test, the composition of Example 3 was evaluated against a commercial product cantaining a polymeric quaternary ammonium e~lt combined with an amphoteric compound. me eNaluation was done on tinted hair, on a '~lf-head" basis, immediately after the tint was sh~pooed from the hair. A tok21 of thirteen models were evaluated in the same manner as the first test.

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It was found that the composition of Example 3 had better wet combing on every head tested. ~ot only was the haLr easier to comb, but it was also sof~er an~ felt clean. In the dry stage, it was softer, easier to comb, felt clean, and, surprisingly, had more body. (Polymeric quaternaries of the type fcund in this commercial product deliver nokiceable bcdy to hair.) It must be noted that when these compositions are used to treat highlighted, permed, or relaxed hair, they are foNnd to be efficacicNs for the conditioning parameters previously mentioned.

Rasonable variations, such as those which would occur to a skilled artisan, can be made herein without departing from the sccpe of the invention.

Claims (10)

1. A hair treatment composition comprising:
(a) a long chain amidoalkyl substituted amine of formula I:

(I) wherein R is a C7-22 alkyl group, R1 is a C1-10 alkylene linkage, and R2 and R3 are independently hydrogen or C1-6 alkyl grcups;
(b) a long chain amine salt of a polymeric acid or a long chain amido alkyl amine salt of a polymeric acid conforming to either formula II or III:
(II) (III) wherein R, R1, R2 and R3 have the meanings given above; R4 is a residue of a C34-68 polymeric acid; and m equals n and is 2 to 4; and (c) an aminofunctional silicone polymer of formula IV:

<IMG (IV) wherein R5 and R6 are independently selected frcm C2-C6 straight and beanched chain alkylene linkages and R7 is H, Si(CH3)3 or Si(CH3)2OCH3, R8 is OH or CH3 and x and y are such that the molecular weight of the polymer is from about 300 to about 500,000.

2. The composition of Claim 1 containing about 0.5 to about 1.5 wt.% of (a), about 0.5 to abaut 2.5 wt.% of (b), and about 0.5 to about 2.5 wt.% of (c).

3. The composition of Claim 2 wherein (a) is at least one compound selected from the group consisting of linoleylamidopropyl dimethylamine, stearamidoethyl diethylamine and oleylamidopropyl dimethylamine.

4. The composition of claim 2 wherein (b) is at least one compound selected from the group consisting of: linoleylamidopropyl dimethylamine dimer dilinoleate, dimethyl lauramine dimer dilinoleate, stearamidopropyl dimethylamine dimer dilinoleate and oleylamidcpropyl dimethylamine dimer dilinoleate.

5. The compostion of Claim 2 wherein (c) is a trimethylsilylamodimethicone.

6. The composition of claim 2 wherein (c) is an amodimethicone.

7. The composition of claim 5 wherein (a) is linoleyl amidopropyldimethylamine and (b) is linoleylamidopropyldimethylamine dimer dilinoleate.

8. The composition of claim 6 wherein (a) is linoleylamidopropyl dimethylamine and (b) is linoleylamidopropyl dimethylamine dimer dilinoleate.

9. A method of improving the combability of hair comprising the step of treating the hair with a composition containing:
(a) a long chain amino alkyl substituted amine of formula I:
(I) wherein R is a C7-22 alkyl group, R1 is a C1-10 alkylene linkage, and R2 and R3 are independently hydrogen or C1-6 alkyl groups;

(b) a long chain amine salt of a polymeric acid a long chain amido alkyl amine salt of a polymeric acid conforming to either Formula II or III:

(II) (III) wherein R, R1, R2 and R3 have the meanings given above; R is a residue of a C34-68 polymeric acid; and m equals n and is 2 to 4; and (c) an aminofunctional silicone polymer of formula IV:

(IV) wherein R5 and R6 are independently selected from C2-C6 straight and beached chain alkylene linkages and R7 is H, Si(CH3)3 or Si(CH3)2 OCH3, R8 is OH or CH3 and x and y are such that the molecular weight of the polymer is from about 300 to about 500,000.

10. The method of Claim 7 wherein the composition contains from about 0.5 to about 1.5 wt.% (a), from about 0.5 to about 2.5 wt% (b) and from about 0.5 to about 2.5 wt. % (c).