US20040063592A1 - Compositions comprising at least one silicone phosphate compound and at least one amine compound, and methods for using the same - Google Patents

Compositions comprising at least one silicone phosphate compound and at least one amine compound, and methods for using the same Download PDF

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US20040063592A1
US20040063592A1 US10/259,741 US25974102A US2004063592A1 US 20040063592 A1 US20040063592 A1 US 20040063592A1 US 25974102 A US25974102 A US 25974102A US 2004063592 A1 US2004063592 A1 US 2004063592A1
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groups
compound
amino groups
chosen
amine compound
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Nghi Nguyen
Hitendra Mathur
David Cannell
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LOreal SA
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Priority to US10/259,741 priority Critical patent/US20040063592A1/en
Assigned to L'OREAL S.A. reassignment L'OREAL S.A. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: MATHUR, HITENDRA, NGUYEN, NGHI VAN, CANNELL, DAVID W.
Priority to BR0303912-9A priority patent/BR0303912A/pt
Priority to EP20030256092 priority patent/EP1402881A1/en
Priority to JP2003341709A priority patent/JP2004123747A/ja
Publication of US20040063592A1 publication Critical patent/US20040063592A1/en
Priority to US12/947,466 priority patent/US8450258B2/en
Abandoned legal-status Critical Current

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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/89Polysiloxanes
    • A61K8/896Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41Amines
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/64Proteins; Peptides; Derivatives or degradation products thereof
    • A61K8/645Proteins of vegetable origin; Derivatives or degradation products thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/64Proteins; Peptides; Derivatives or degradation products thereof
    • A61K8/65Collagen; Gelatin; Keratin; Derivatives or degradation products thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/817Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions or derivatives of such polymers, e.g. vinylimidazol, vinylcaprolactame, allylamines (Polyquaternium 6)
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/12Preparations containing hair conditioners

Definitions

  • the present invention relates to compositions, kits comprising these compositions, and methods for using these compositions for care, treatment, conditioning or durable conditioning of at least one keratinous fiber, including at least one human keratinous fiber, comprising at least one silicone compound comprising at least one phosphate group and at least one amine compound comprising greater than three amino groups, wherein the amino groups are identical or different.
  • Shampoos generally comprise surfactants, such as anionic surfactants, to clean the hair. It is known that anionic surfactants not only remove the dirt and soil but also remove the naturally-present sebum from hair. Thus, shampoos may leave the hair dull and dry, that is, with what is known in the art as “creak”. This generally makes the hair extremely difficult to comb either wet or dry, and once dry, the hair may not be amenable to styling, and may have undesirable electrostatic properties, causing the hair to “fly away.” Due to the unsatisfactory condition of shampooed hair, many consumers use a conditioning composition to improve at least one of these undesirable characteristics.
  • surfactants such as anionic surfactants
  • Conditioning agents include cationic compounds such as cationic surfactants and cationic polymers which may render the hair more manageable, at least temporarily.
  • cationic compounds such as cationic surfactants and cationic polymers which may render the hair more manageable, at least temporarily.
  • quaternized ammonium compounds may be used as hair conditioning agents. These compounds may be substantive to the hair due to the ionic interaction between their positive charge on the ammonium nitrogen atom and negative charges on the surface of the hair fibers. This ionic interaction, in effect, allows the conditioning agents to coat the hair shaft and thereby prevent tangling and matting of the individual hair fibers.
  • the ability of these cationic compounds to adsorb to and/or react with the keratinous material of the hair makes them desirable compounds for conditioning the hair, such as for detangling wet hair and imparting manageability to dry hair.
  • the effect of these conditioning agents may not be long lasting. Normally, because of the weak ionic bond between the quaternized ammonium compounds and the hair fiber, the quaternized ammonium compounds are washed off the hair easily. This is especially true during shampooing, wherein anionic surfactants are present, generally in high concentrations. In such a case, the anionic surfactants in the shampoo and the cationic conditioning agents are known to form a complex which may be easily removed from the hair during the shampooing and/or which decreases the cleansing capabilities of the anionic surfactant and the conditioning capabilities of the conditioning agent.
  • silicone compounds have been used as conditioning agents.
  • these compounds lack durability on the hair shaft as these compounds are generally hydrophobic. Accordingly, silicone compounds may not be deposited on the hair, or are easily removed due to their weak hydrophobic interactions with the keratinous material of the hair.
  • compositions containing certain silicone compounds, certain amine compounds and certain silicone compounds comprising an amino group have previously been disclosed.
  • Certain phosphated silicone polymers are known.
  • U.S. Pat. Nos. 5,070,171 and 5,149,765 the disclosures of which are hereby incorporated herein by reference, relate to phosphated silicone polymers which are disclosed to provide a nonvolatile lubricant antistat which can be applied to a variety of fibers.
  • U.S. Pat. No. 5,093,452 the disclosure of which is hereby incorporated herein by reference, relates to silicone phosphate organic amine salts wherein one or more pendant phosphate groups in free acid form is/are neutralized with a fatty amine group.
  • the organic amines may be chosen from alkyl amido amines, imidazoline, alkoxyethyl alkyl amines, and alkyl tertiary amines. However, these compounds may not impart durable conditioning to at least one keratinous fiber, and may not react to condition keratinous fibers in a synergistic manner.
  • U.S. Pat. No. 5,362,484 discloses a hair care composition for conditioning hair with silicone oil comprising a stable emulsion of water-insoluble hair conditioning silicone oil dispersed in a liquid carrier composed essentially of polyoxyalkylene glycol and an emulsifier consisting of a silicone phosphate salt in which the anionic moiety comprises a copolymer of dimethylpolysiloxane and polyoxyethylene.
  • the inventors have envisaged the application to at least one keratinous fiber of at least one silicone compound comprising at least one phosphate group and at least one amine compound comprising greater than three amino groups, wherein the amino groups are identical or different.
  • the inventors have discovered that such compositions, and methods comprising applying these compositions to at least one keratinous fiber condition the at least one keratinous fiber.
  • the compositions of the invention may also be used to care for, or treat, the at least one keratinous fiber. Further, in one embodiment, the inventive compositions impart a durable conditioning to the at least one keratinous fiber.
  • the present invention in one aspect, provides a composition for conditioning at least one keratinous fiber comprising at least one silicone compound comprising at least one phosphate group and at least one amine compound comprising greater than three amino groups, wherein the amino groups may be identical or different, and further wherein the at least one silicone compound and the at least one amine compound are present in a combined amount effective to condition the at least one keratinous fiber.
  • the at least one silicone compound and the at least one amine compound are present in a combined amount effective to durably condition the at least one keratinous fiber.
  • the at least one silicone compound and the at least one amine compound are present in the inventive composition in a synergistically effective amount to condition at least one keratinous fiber.
  • the present invention provides a composition for durable conditioning of at least one keratinous fiber comprising at least one silicone compound comprising at least one phosphate group and at least one amine compound comprising greater than three amino groups, wherein the amino groups may be identical or different, and further wherein the at least one silicone compound and the at least one amine compound are present in a combined amount effective to durably condition the at least one keratinous fiber.
  • the at least one silicone compound and the at least one amine compound are present in the inventive composition in a synergistically effective amount to durably condition at least one keratinous fiber.
  • the present invention is drawn to a method for conditioning at least one keratinous fiber comprising applying to the at least one keratinous fiber comprising at least one silicone compound comprising at least one phosphate group and at least one amine compound comprising greater than three amino groups, wherein the amino groups may be identical or different, and further wherein the at least one silicone compound and the at least one amine compound are present in a combined amount effective to condition the at least one keratinous fiber.
  • the at least one silicone compound and the at least one amine compound are present in the inventive composition in a synergistically effective amount to condition at least one keratinous fiber.
  • the at least one keratinous fiber may be rinsed after the application.
  • the at least one keratinous fiber may be wet with water prior to application of the composition.
  • the present invention is drawn to a method for durably conditioning at least one keratinous fiber comprising applying to the at least one keratinous fiber comprising at least one silicone compound comprising at least one phosphate group and at least one amine compound comprising greater than three amino groups, wherein the amino groups may be identical or different, and further wherein the at least one silicone compound and the at least one amine compound are present in a combined amount effective to durably condition the at least one keratinous fiber.
  • the at least one silicone compound and the at least one amine compound are present in the inventive composition in a synergistically effective amount to durably condition at least one keratinous fiber.
  • the at least one keratinous fiber may be rinsed after the application.
  • the at least one keratinous fiber may be wet with water prior to application of the composition.
  • the present invention is drawn to a method for caring for or treating at least one keratinous fiber comprising applying to the at least one keratinous fiber at least one silicone compound comprising at least one phosphate group and at least one amine compound comprising greater than three amino groups, wherein the amino groups may be identical or different, and further wherein the at least one silicone compound and the at least one amine compound are present in a combined amount effective to condition the at least one keratinous fiber.
  • the at least one silicone compound and the at least one amine compound are present in the inventive composition in a synergistically effective amount to condition at least one keratinous fiber.
  • the at least one keratinous fiber may be rinsed after the application.
  • the at least one keratinous fiber may be wet with water prior to application of the composition.
  • the present invention provides a kit for caring for, treating, conditioning, or durably conditioning comprising at least two compartments, wherein a first compartment comprises a first composition comprising at least one silicone compound comprising at least one phosphate group, and wherein a second compartment comprises a second composition comprising at least one amine compound comprising greater than three amino groups, wherein the amino groups are identical or different.
  • the present invention also provides compositions, kits comprising these compositions, and methods for using these compositions for care, treatment, conditioning or durable conditioning of at least one keratinous fiber, including at least one human keratinous fiber, comprising at least one silicone compound comprising at least one phosphate group and at least one compound chosen from at least one amine compound comprising greater than three amino groups as defined herein, silicone compounds comprising at least one amino group different from the at least one silicone compound comprising at least one phosphate group, aminosilicone compounds comprising at least one amino group wherein the aminosilicone compounds are different from the at least one silicone compound comprising at least one carboxylic acid group, aminated polysaccharides comprising at least one amino group, hydrolysates of aminated polysaccharides comprising at least one amino group, and aminated monosaccharides comprising at least one amino group, wherein the at least one silicone compound and the at least one compound are present in a combined amount effective to condition the at least one keratinous fiber.
  • amino groups as defined herein includes primary amino groups, secondary amino groups, and tertiary amino groups, and further includes amino groups which are terminal, pendant, and intercalated in a skeleton of the at least one amine compound, but does not, for example, include quaternary amino groups, amido groups, imino groups, nitrilo groups, or heteroatom analogs of any of the foregoing.
  • At least one means one or more and thus includes individual components as well as mixtures/combinations.
  • Constanting means imparting to at least one keratinous fiber at least one property chosen from combability, manageability, moisture-retentivity, luster, shine, and softness. The state of conditioning is evaluated by measuring, and comparing, the ease of combability of the treated hair and of the untreated hair in terms of combing work (gm-in). See Examples 1-8.
  • Form from means obtained from chemical reaction of, wherein “chemical reaction,” includes spontaneous chemical reactions and induced chemical reactions.
  • the phrase “formed from” is open ended and does not limit the components of the composition to those listed, e.g., as component (i) and component (ii). Furthermore, the phrase “formed from” does not limit the order of adding components to the composition or require that the listed components (e.g., components (i) and (ii)) be added to the composition before any other components.
  • “Durable conditioning” as used herein means that, following at least six shampoos after treatment, treated hair remains in a more conditioned state as compared to untreated hair.
  • Hydrocarbons include alkanes, alkenes, and alkynes, wherein the alkanes comprise at least one carbon, and the alkenes and alkynes each comprise at least two carbons; further wherein the hydrocarbons may be chosen from linear hydrocarbons, branched hydrocarbons, and cyclic hydrocarbons; further wherein the hydrocarbons may optionally be substituted; and further wherein the hydrocarbons may optionally further comprise at least one heteroatom intercalated in the hydrocarbon chain, wherein the at least one heteroatom is different from the greater than three amino groups.
  • Silicone compound includes, for example, silica, silanes, silazanes, siloxanes, and organosiloxanes; and refers to a compound comprising at least one silicon; wherein the silicone compound may be chosen from linear silicone compounds, branched silicone compounds, and cyclic silicone compounds; further wherein the silicone compound may optionally be substituted; and further wherein the silicone compound may optionally further comprise at least one heteroatom intercalated in the silicone chain, wherein the at least one heteroatom is different from the at least one silicon.
  • “Substituted,” as used herein, means comprising at least one substituent.
  • substituents include atoms, such as oxygen atoms and nitrogen atoms, as well as functional groups, such as hydroxyl groups, ether groups, alkoxy groups, acyloxyalkyl groups, oxyalkylene groups, polyoxyalkylene groups, carboxylic acid groups, amine groups, acylamino groups, amide groups, halogen containing groups, ester groups, thiol groups, sulphonate groups, thiosulphate groups, siloxane groups, and polysiloxane groups.
  • the substituent(s) may be further substituted.
  • Ethylene oxide group refers to a group of formula —CH 2 CH 2 —O—.
  • “Propylene oxide group” as defined herein includes groups of formula —CH 2 CH 2 CH 2 —O—, groups of formula (CH 3 )CHCH 2 —O—, and groups of formula —CH 2 (CH 3 )CH—O—.
  • Keratinous fiber as defined herein may be human keratinous fiber, and may be chosen from, for example, hair, eyelashes, and eyebrows.
  • Polymers include homopolymers and copolymers formed from at least two different types of monomers.
  • “Synergy,” as used herein, refers to the phenomenon in which the effect of at least two components (e.g., the at least one silicone compound comprising at least one phosphate group and the at least one amine compound comprising at least three amino groups) is more than additive, i.e., the effect observed with the at least two components is greater than that observed for either component alone.
  • compositions comprising at least one silicone compound chosen from a certain class of silicone compounds and at least one amine compound chosen from a certain class of amine compounds had at least one property that make it particularly desirable for use on keratinous fibers.
  • compositions comprising at least one silicone compound comprising at least one phosphate group and at least one amine compound comprising greater than three amino groups (which amino groups may be identical or different) were found to condition the hair and also found to be useful in caring for and treating the hair.
  • these compositions may impart to the at least one keratinous fiber a durable conditioning even after shampooing the at least one keratinous fiber subsequent to treatment with such a composition.
  • the present invention provides compositions for conditioning of at least one keratinous fiber comprising at least one silicone compound comprising at least one phosphate group and at least one amine compound comprising greater than three amino groups, wherein the amino groups may be identical or different, and further wherein the at least one silicone compound and the at least one amine compound are present in a combined amount effective to condition the at least one keratinous fiber.
  • the ratio of amino groups in the at least one amine compound to phosphate groups in the at least one silicone compound may not be determinative of the effectiveness of the inventive composition in conditioning at least one keratinous fiber as long as the at least one amine compound comprises greater than three amino groups.
  • the examples below show that the molecular weight, the concentration, and/or the nature of the silicone compound may affect the effectiveness of the composition comprising at least one silicone compound and the at least one amine compound in conditioning at least one keratinous fiber.
  • the at least one silicone compound comprising at least one phosphate group may be chosen from water-soluble silicone compounds comprising at least one phosphate group, oil soluble silicone compounds comprising at least one phosphate group, water-dispersible silicone compounds comprising at least one phosphate group, and silicone compounds comprising at least one phosphate group which are soluble in organic solvents.
  • the at least one silicone compound comprising at least one phosphate group further comprises at least one alkoxylated chain, wherein the at least one alkoxy group may be chosen from terminal alkoxy groups, pendant alkoxy groups, and alkoxy groups which are intercalated in the skeleton of the at least one silicone compound.
  • the at least one phosphate group may be chosen from terminal phosphate groups and pendant phosphate groups. Further, the at least one phosphate group may be chosen from groups of formula —O—P(O)(OH) 2 , groups of formula —O—P(O)(OH)(OR), and groups of formula —O—P(O)(OR) 2 , wherein R may be chosen from H, inorganic cations, and organic cations.
  • inorganic cations include alkali metals, such as, for example, potassium lithium, and sodium.
  • a non-limiting example of organic cations is at least one additional silicone compound which may be identical to or different from the at least one silicone compound bonded to the other oxygen of the phosphate group.
  • the at least one silicone compound comprising at least one phosphate group is chosen from silicone compounds of formula (I):
  • R 1 which may be identical or different, are each chosen from H, organic cations, inorganic cations, optionally substituted hydrocarbons (such as alkyl groups and alkenyl groups comprising from 1 to 22 carbon atoms), optionally substituted aromatic groups,
  • c, and d which may be identical or different, are each integers ranging from 0 to 20;
  • e is an integer ranging from 0 to 19;
  • x is an integer ranging from 0 to 21;
  • c, d, and e which may be identical or different, are each integers ranging from 0 to 20;
  • x is an integer ranging from 0 to 21;
  • a is an integer ranging from 0 to 200;
  • b is an integer ranging from 0 to 200;
  • R′ which may be identical or different, are each chosen from optionally substituted hydrocarbons, such as alkyl groups and alkenyl groups comprising from 1 to 22 carbon atoms, optionally substituted aromatic groups, groups of formula (III) as defined above and salts thereof; and
  • R which may be identical or different, are each chosen from optionally substituted hydrocarbons, such as alkyl groups and alkenyl groups comprising from 1 to 22 carbon atoms, optionally substituted aromatic groups, optionally substituted divalent hydrocarbons, such as alkylene groups and alkenylene groups comprising from 1 to 22 carbon atoms, optionally substituted divalent aromatic groups, groups of formula (III) as defined above and salts thereof, and groups of formula (V):
  • the (CH 2 ) 3 end is bonded to the silicon of the compound of formula (IV) and the (EO) or (PO) end, if present, is bonded to the oxygen of the compound of formula (I);
  • c, d, and e which may be identical or different, are each integers ranging from 0 to 20;
  • EO is an ethylene oxide group
  • PO is a propylene oxide group
  • At least one R is chosen from groups of formula (V) and salts thereof;
  • At least one R 1 is chosen from groups of formula (IV) and salts thereof and at least one other R 1 is chosen from H, organic cations, and inorganic cations.
  • Non-limiting examples of the inorganic cations include alkali metals, such as potassium, lithium, and sodium.
  • Non-limiting examples of the at least one silicone compound include those commercially available from Phoenix Chemical, Inc. of New Jersey under the name of Pecosil®, such as Pecosil® PS-100, Pecosil® PS-112, Pecosil® PS-150, Pecosil® PS-200, Pecosil® WDS-100, Pecosil® WDS-200, Pecosil® PS-100 B, and Pecosil® PS-100 K and those commercially available from Siltech under the name Silphos A-100 and Silphos A-150.
  • Other non-limiting examples of the at least one silicone compound include those described in U.S. Pat. Nos. 5,070,171, 5,093,452, and 5,149,765 the disclosures of which are incorporated herein by reference.
  • the at least one silicone compound is present in the inventive composition in an amount ranging from 0.01% to 50% by weight relative to the total weight of the composition. In another embodiment, the at least one silicone compound is present in an amount ranging from 0.1% to 30% by weight relative to the total weight of the composition.
  • the at least one silicone compound according to the present invention may be commercially available, and may come from suppliers in the form of a dilute solution. The amounts of the at least one silicone compound disclosed herein therefore reflect the weight percent of active material.
  • the greater than three amino groups of the at least one amine compound are chosen from primary amino groups, secondary amino groups and tertiary amino groups. In one embodiment, the greater than three amino groups are identical. In another embodiment, the greater than three amino groups are different.
  • the at least one amine compound of the present invention comprises greater than three amino groups. In one embodiment, the at least one amine compound of the present invention comprises at least four amino groups, such as greater than four amino groups. In one embodiment, the at least one amine compound of the present invention comprises at least five amino groups, such as greater than five amino groups. In one embodiment, the at least one amine compound of the present invention comprises at least six amino groups, such as greater than six amino groups. In one embodiment, the at least one amine compound of the present invention comprises at least ten amino groups, such as greater than ten amino groups.
  • the at least one amine compound may, for example, be chosen from hydrocarbons comprising greater than three amino groups, and silicone compounds comprising greater than three amino groups different from the at least one silicone compound comprising at least one phosphate group.
  • the at least one amine compound may, for example, be chosen from aminosilicone compounds comprising at least three amino groups wherein the aminosilicone compounds are different from the at least one silicone compound comprising at least one carboxylic acid group.
  • suitable aminosilicone compounds comprising at least three amino groups are DC 2-8566 and DC 2-8902, both of which are commercially available from Dow Corning.
  • the at least one amine compound may, for example, be chosen from aminated polysaccharides comprising greater than three amino groups, such as, for example, chitosan, and hydrolysates of aminated polysaccharides comprising greater than three amino groups.
  • the at least one amine compound may, for example, be chosen from polymers.
  • Suitable polymers for use as the at least one amine compound are polymers comprising greater than three amino groups as defined herein.
  • suitable polymers include homopolymers comprising greater than three amino groups, copolymers comprising greater than three amino groups, and terpolymers comprising greater than three amino groups.
  • the at least one amine compound comprising greater than three amino groups may be chosen from, for example, polymers comprising greater than three amino groups formed from (i) at least one monomer unit comprising greater than three amino groups as defined herein, and, optionally, (ii) at least one additional monomer unit different from the at least one monomer (i); and polymers comprising greater than three amino groups formed from (i) at least one monomer comprising at least one amino group as defined herein, and, optionally, (ii) at least one additional monomer unit different from the at least one monomer (i).
  • the at least one additional monomer different from the at least one monomer (i) may or may not comprise at least one amino group as defined herein.
  • the at least one amine compound is chosen from polyamines.
  • polyamines comprise at least two repeating units, wherein each unit comprises at least one amino group as defined herein.
  • polyamines are chosen from polyethyleneimines.
  • Polyethyleneimines suitable for use in the compositions of the present invention may optionally be substituted.
  • Non-limiting examples of polyethyleneimines which may be used in the composition according to the present invention are the LupasolTM products commercially available from BASF.
  • Suitable examples of LupasolTM polyethyleneimines include LupasolTM PS, Lupasol PL, LupasolTM PR8515, LupasolTM G20, LupasolTM G35 as well as LupasolTM SC® Polythyleneimine Reaction Products (such as LupasolTM SC-61 B®, LupasolTM SC-62J®, and LupasolTM SC-86X®).
  • Other non-limiting examples of polyethyleneimines which may be used in the composition according to the present invention are the EpominTM products commercially available from Aceto.
  • Suitable examples of EpominTM polyethyleneimines include EpominTM SP-006, EpominTM SP-012, EpominTM SP-018, and EpominTM P-1000.
  • the at least one amine compound comprising greater than three amino groups is chosen from proteins and protein derivatives.
  • suitable proteins and protein derivatives for use in the present invention include those listed at pages 1701 to 1703 of the C.T.F.A. International Cosmetic Ingredient Dictionary and Handbook, 8 th edition, vol. 2, (2000).
  • the at least one amine compound comprising greater than three amino groups is chosen from wheat protein, soy protein, oat protein, collagen, and keratin protein.
  • the at least one amine compound comprising greater than three amino groups is not chosen from proteins and protein derivatives. In one embodiment, the at least one amine compound comprising greater than three amino groups is not chosen from compounds comprising lysine, compounds comprising arginine, and compounds comprising histidine. In one embodiment, the at least one amine compound comprising greater than three amino groups is chosen from compounds comprising lysine, compounds comprising arginine, compounds comprising histidine, and compounds comprising hydroxylysine.
  • the at least one amine compound is present in the inventive composition in an amount ranging from 0.01% to 30% by weight relative to the total weight of the composition. In another embodiment, the at least one amine compound is present in an amount ranging from 0.1% to 15% by weight relative to the total weight of the composition.
  • the at least one amine compound according to the present invention may be commercially available, and may come from suppliers in the form of a dilute solution. The amounts of the at least one amine compound disclosed herein therefore reflect the weight percent of active material.
  • the at least one silicone compound and the at least one amine compound are present in the inventive composition in a synergistically effective amount to condition at least one keratinous fiber.
  • Example 1 provides for a simple screening test, the combability test (See Garcia, M. L., and Diaz, J., J. Soc. Cosmet. Chem. 27, 370-398 (1976)), to determine the presence of synergy and what constitutes a synergistically effective amount of the at least one silicone compound and the at least one amine compound in such mixtures.
  • the combability test is known in the art to correlate well to the amount of conditioning that is afforded hair by a composition. Wet combing work of normal hair is determined prior to treatment.
  • the hair is then divided into three groups and treated, one group with a composition comprising both the at least one silicone compound and the at least one amine compound, a second group with a control solution containing the at least one silicone compound alone, and a third group with a control solution containing the at least one amine compound alone.
  • the increase in work or force required to comb wet hair is compared for hair treated with the inventive composition versus the hair treated with the controls to determine if a synergistic effect is observed.
  • compositions of the present invention as well as those used in the methods of the present invention may, for example, be in the form of a shampoo, a conditioner, a hair dye, a hair bleach, a permanent waving product, a relaxing product, a styling product, or a hair care product, such as a hair treatment.
  • inventive compositions may further comprise at least one solvent.
  • Non-limiting examples of the at least one solvent include water and organic solvents.
  • Non-limiting examples of organic solvents include C 1 -C 4 alkanols, such as ethanol and isopropanol; glycerol; glycols and glycol ethers, such as 2-butoxyethanol, propylene glycol, propylene glycol monomethyl ether, diethylene glycol monoethyl and monomethyl ether, and aromatic alcohols, such as benzyl alcohol and phenoxyethanol, and mixtures thereof.
  • the inventive compositions may be acidic or basic.
  • these compositions may further comprise at least one suitable additive chosen from additives commonly used in compositions for keratinous fibers.
  • the at least one suitable additive include anionic surfactants different from the at least one silicone compound and from the at least one amine compound, cationic surfactants different from the at least one silicone compound and from the at least one amine compound, nonionic surfactants different from the at least one silicone compound and from the at least one amine compound, amphoteric surfactants different from the at least one silicone compound and from the at least one amine compound, zwitterionic surfactants different from the at least one silicone compound and from the at least one amine compound, thiol compounds, fragrances, penetrating agents, antioxidants, sequestering agents, opacifying agents, solubilizing agents, emollients, colorants, screening agents (such as sunscreens and UV filters), preserving agents, vitamins, silicones, polymers such as thickening polymers different from the at least one silicone compound and from
  • a solution containing a combined amount of 5% by weight of Pecosil® PS100 (3.92% by weight) and LupasolTM PR8515 (1.08% by weight) and having a pH adjusted to 6 was used to treat bleached hair swatches (0.5 g of solution/g hair). After 2 minutes of treatment, the hair swatches were rinsed with warm water for 1 minute. Before and after treatment, the force needed to comb through the wet hair swatches was determined using an Instron Tensile Tester. After the initial treatment and combability test, the hair swatches were shampooed 6 times with 10% SLES, and the combability of the shampooed hair swatches was determined. The percent improvement (% improvement) is defined as:
  • W a Combing Work after treatment, or Combing Work after 6 shampoos following treatment
  • results indicate that durable conditioning of hair is possible with a solution comprising 2% of the silicone compound/amine compound composition. Further, the results indicate that the durable conditioning effect increased as did the concentration of the at least one silicone compound and the at least one amine compound.
  • the amphoteric surfactant system consisted of the silicone compound and the amine compound in a combined amount of 3% and 6% disodium cocoamphodipropionate (Mackam 2CSF40 CG commercially available from McIntyre).
  • the nonionic surfactant system consisted of the silicone compound and the amine compound in a combined amount of 3%, 4% glyceryl stearate and PEG-100 (Arlacel 165 FI commercially available from Uniquema), and 4% cetearyl alcohol (Lanetter O commercially available from Cognis). The results from the wet combability tests are shown in Table 5.
  • the amphoteric surfactant system consisted of the silicone compound and the amine compound in a combined amount of 3% and 6% disodium cocoamphodipropionate (Mackam 2CSF40 CG commercially available from McIntyre) at pH 10.5.
  • the nonionic surfactant system consisted of the silicone compound and the amine compound in a combined amount of 3%, 4% glyceryl stearate and PEG-100 (Arlacel 165 FI commercially available from Uniquema), and 4% cetearyl alcohol (Lanetter O commercially available from Cognis) at pH 10.5.
  • the results from the wet combability tests are shown in Table 6.
  • bleached hair swatches were treated with one of two shampoo-based solutions containing both a silicone compound (Pecosil® PS-100) and an amine compound (Lupasol G-35) and an amphoteric surfactant (either a sulfate compound or a carboxylate compound).
  • the sulfate-containing shampoo contained the silicone compound and the amine compound in a combined amount of 3% by weight relative to the total weight of the composition formed from 2.32% Pecosil® PS-100 and 0.68% Lupasol G-35, 10% sodium laryl ether sulfate and 6% disodium cocoamphodipropionate at pH 5.5.
  • the carboxylate-containing shampoo contained the silicone compound and the amine compound in a combined amount of 1% by weight relative to the total weight of the composition formed from 0.78% Pecosil® PS-100 and 0.22% Lupasol G-35, 4% trideceth-7 carboxylic acid, and 7.7% disodium cocoamphodipropionate at pH 5.5.
  • the results from the wet combability tests are shown in Table 7. TABLE 7 Durable Conditioning Effects of the Silicone Compound/Amine Compound Composition in Shampoo Systems % Improvement % Improvement After After Shampoo System Treatment 6 Shampoos Sulfate/Amphoteric 78.21 43.21 Carboxylate/Amphoteric 89.43 59.18

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US10/259,741 2002-09-30 2002-09-30 Compositions comprising at least one silicone phosphate compound and at least one amine compound, and methods for using the same Abandoned US20040063592A1 (en)

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US10/259,741 US20040063592A1 (en) 2002-09-30 2002-09-30 Compositions comprising at least one silicone phosphate compound and at least one amine compound, and methods for using the same
BR0303912-9A BR0303912A (pt) 2002-09-30 2003-09-29 Composição para o condicionamento, composição para o condicionamento durável, método para o condicionamento, método para o condicionamento durável, método para o cuidado ou tratamento e kit para o cuidado, tratamento, condicionamento ou condicionamento durável
EP20030256092 EP1402881A1 (en) 2002-09-30 2003-09-29 Compositions comprising at least one silicone phosphate compound and at least one amine compound, and methods for using the same
JP2003341709A JP2004123747A (ja) 2002-09-30 2003-09-30 少なくとも一のシリコーンホスファート化合物と少なくとも一のアミン化合物を含有する組成物及び該組成物の使用方法
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US20070107141A1 (en) * 2005-11-16 2007-05-17 L'oreal Process for styling dyed hair and inhibiting its color loss during shampooing
US20070110690A1 (en) * 2005-11-16 2007-05-17 L'oreal Process for inhibiting hair from becoming frizzy
US20090074683A1 (en) * 2007-09-14 2009-03-19 L'oreal Compositions and methods for treating keratinous substrates

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US8128917B2 (en) 2005-06-16 2012-03-06 L'oréal Aqueous polyamine-containing carrier systems for water-insoluble materials
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US20070110691A1 (en) * 2005-11-16 2007-05-17 L'oreal Process for inhibiting dyed hair fibers from losing their color during shampooing
US20070107141A1 (en) * 2005-11-16 2007-05-17 L'oreal Process for styling dyed hair and inhibiting its color loss during shampooing
US20070110690A1 (en) * 2005-11-16 2007-05-17 L'oreal Process for inhibiting hair from becoming frizzy
US7608569B2 (en) * 2005-11-16 2009-10-27 L'oréal Process for inhibiting hair from becoming frizzy using a polyethyleneimine/anionic silicone mixture
US7727288B2 (en) 2005-11-16 2010-06-01 L'oreal Process for styling dyed hair and inhibiting its color loss during shampooing
US20100233113A1 (en) * 2005-11-16 2010-09-16 L'oréal Process for inhibiting dyed hair fibers from losing their color during shampooing
US8236743B2 (en) * 2005-11-16 2012-08-07 L'oréal Process for inhibiting dyed hair fibers from losing their color during shampooing
US20120269756A1 (en) * 2005-11-16 2012-10-25 L'oréal Process for inhibiting dyed hair fibers from losing their color during shampooing
US8648023B2 (en) * 2005-11-16 2014-02-11 L'oréal Process for inhibiting dyed hair fibers from losing their color during shampooing
US20090074683A1 (en) * 2007-09-14 2009-03-19 L'oreal Compositions and methods for treating keratinous substrates
US8658140B2 (en) * 2007-09-14 2014-02-25 L'oreal Compositions and methods for treating keratinous substrates

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