METHOD FOR TREATMENT OF KERATINIC FIBERS USING A CROSS-CUT COMPOUND, A POLYMERIC PHOTO-INITIATOR AND LIGHT IRRADIATION
A method using a polymeric photo-initiator and crosslinkable compounds with light irradiation addresses the challenge of selective and durable cosmetic deposition on keratin fibers, enhancing properties like softness and strength while allowing permanent shaping.
Patent Information
- Authority / Receiving Office
- FR · FR
- Patent Type
- Patents
- Current Assignee / Owner
- LOREAL SA
- Filing Date
- 2023-03-03
- Publication Date
- 2026-06-19
AI Technical Summary
Existing methods for treating keratin fibers fail to provide selective and durable deposition of cosmetic actives, leading to inadequate persistence and resistance to washing, while also lacking control over the location and reversibility of these deposits.
A process involving the application of a polymeric photo-initiator compound and a crosslinkable non-color compound followed by light irradiation, which creates a durable and selective coating on keratin fibers, enhancing cosmetic properties such as softness and strength.
The process results in keratin fibers with persistent cosmetic properties resistant to washing, improved sheathing, and the ability to shape fibers permanently.
Abstract
Description
Title of the invention: METHOD FOR TREATMENT OF KERATINIC FIBERS USING A RE-CROSSABLE COMPOUND, A POLYMERIC PHOTO-INITIATOR AND LIGHT IRRADIATION
[0001] The present invention relates to a process for treating, preferably for conditioning and / or shaping, keratin fibers comprising at least one step of applying to said fibers, one or more compositions, comprising at least one polymeric photo-initiator compound and at least one crosslinkable non-color compound, and then at least one step of light irradiation of said keratin fibers.
[0002] The invention also relates to a composition comprising at least one polymeric photoinitiator compound and at least one crosslinkable non-colorant compound.
[0003] It is still relevant to give keratin fibers cosmetic and usage properties that are particularly durable over time, and in particular persistent after washing.
[0004] Thus, it is particularly desirable to produce deposits of cosmetic actives on keratin fibers, and in particular on hair, which are permanent to washing and external aggressions (combing, rain, sun, hair dryer, etc.), capable of conferring lasting cosmetic properties to keratin fibers, the location of which is precisely controlled and reversible at any time.
[0005] In the past, the resistance of a cosmetic active ingredient deposit to washing could be achieved by a low solubility of the deposit in aqueous detergent media.
[0006] However, this solution does not allow for selective deposition of cosmetic actives and does not provide complete satisfaction in terms of persistence, in particular resistance to washing.
[0007] There is therefore a real need to develop processes for treating keratin fibers capable of giving keratin fibers, in a selective and homogeneous way, good cosmetic properties that last over time and in particular are residual to washing.
[0008] It is of particular interest to develop processes for treating keratin fibers capable of selectively depositing cosmetic active ingredients on keratin fibers, thereby providing better sheathing of keratin fibers, and in a lasting manner.
[0009] These objectives are achieved with the present invention, which relates in particular to a process for treating keratin fibers comprising at least the following steps: (i) the application to said keratin fibers, simultaneously or sequentially: a) of at least one polymeric photoinitiator compound, and b) of at least one crosslinkable non-colorant compound; then (ii) exposure of said keratin fibers to light radiation.
[0010] It has been observed that the process according to the invention makes it possible to give the treated keratin fibers good cosmetic properties, such as softness, body, a pleasant feel, easier detangling, and suppleness, and this in a selective manner. It has been observed in particular that the process according to the invention makes it possible to obtain a very good coating of the keratin fibers that is resistant to washing.
[0011] It has also been observed that the properties conferred on keratin fibers treated with the process according to the invention are particularly persistent to washing.
[0012] Furthermore, according to a first aspect of the invention, the process according to the invention makes it possible to repair, significantly and durably strengthen keratin fibers.
[0013] According to a second aspect of the invention, the process according to the invention makes it possible to shape the keratin fibers easily and permanently over time.
[0014] The invention also relates to a composition comprising: a) at least one polymeric photo-initiator compound, and b) at least one crosslinkable non-colorant compound.
[0015] Other objects, features, aspects and advantages of the invention will become even clearer upon reading the description and examples that follow.
[0016] In this description, and unless otherwise indicated: - the expression "at least one" is equivalent to the expression "one or more" and can be substituted for it; - the expression "between... and..." is equivalent to the expression "ranging from... to..." and can be substituted for it, and implies that the limits are included; - By the expression "greater than" and respectively the expression "less than" in the meaning of the present invention, we mean an open interval that is strictly greater than, respectively strictly less than, and therefore that the bounds are not included. - For the purposes of this application, "keratin fibers" refers more specifically to human keratin fibers, and more preferably to hair. - For the purposes of this application, "fatty acid" means an organic acid comprising in its structure a hydrocarbon chain, linear or branched, saturated or unsaturated, comprising from 6 to 40 carbon atoms, preferably from 8 to 30 carbon atoms, more preferably from 10 to 22 carbon atoms. - For the purposes of this application, "fatty alcohol" means an alcohol comprising in its structure a linear or branched, saturated or unsaturated hydrocarbon chain comprising from 6 to 60 carbon atoms, preferably from 7 to 60 carbon atoms, preferably from 7 to 40 carbon atoms, better from 8 to 40 carbon atoms, and even better from 12 to 26 carbon atoms. - An "alkylene chain" represents a divalent acyclic hydrocarbon chain in Ci-C2O; particularly in Ci-C6, more particularly in Ci-C2 when the chain is linear; possibly substituted by one or more groups, identical or different, chosen from i) hydroxy, ii) (Ci-C2)alkoxy, iii) (poly)hydroxy(C2-C4)alkoxy(di)(Ci-C2)(alkyl)amino, iv) Ra-Za-C(Zb)-Zc-, and v) Ra-Za-S(O)t—Zc- with Za, Zb, identical or different, representing an oxygen atom, a sulfur atom, or an NR group, a', Zc, representing a bond, an oxygen atom, a sulfur atom, or an NRa group; Ra, representing an alkali metal, a hydrogen atom, an alkyl group or is absent if another part of the cationic molecule and Ra' representing a hydrogen atom or an alkyl group;more specifically the groups iv) are chosen from carboxylate -C(O)O or -C(O)OMetal (Metal = alkali metal), carboxyl -C(O)-OH, guanidino H2H-C(NH2)-NH-, amidino H2H-C(NH2)-, (thio)ureo H2 NC(O)-NH- and H2N-C(S)-NH-, aminocarbonyl -C(O)-NRa'2 or aminothiocarbonyl -C(S)-NRa'2; carbamoyl Ra'-C(O)-NRa'- or thiocarbamoyl Ra'-C(S)-NRa'- with Ra', identical or different, representing a hydrogen atom or a (C1-C4) alkyl group; ; - The "aryl" or "heteroaryl" radicals, or the aryl or heteroaryl part of a radical, can be substituted by at least one substituent attached to a carbon atom, chosen from: * an alkyl radical in CrCi6, preferably in CrC8, possibly substituted by one or more radicals chosen from among the hydroxyl, alkoxy radicals in CrC2, (poly)-hydroxyalkoxy in C2-C4, acylamino, amino substituted by two alkyl radicals, identical or different, in CrC4, possibly bearing at least one hydroxyl group or, the two radicals being able to form with the nitrogen atom to which they are attached, a heterocycle comprising 5 to 7 links, preferably 5 or 6 links, saturated or unsaturated possibly substituted possibly comprising another heteroatom identical or different from the nitrogen; * a halogen atom; * a hydroxyl group; * an alkoxy radical in CrC2; * a C2-C4 (poly)-hydroxyalkoxy radical; * an amino radical; * a heterocycloalkyl radical with 5 or 6 links; * a heteroaryl radical with 5 or 6 links possibly cationic, preferably imidazolium, and possibly substituted by a (C1-C4) alkyl radical, preferably methyl; * an amino radical substituted by one or two alkyl radicals, identical or different, in the Ci-C6 configuration, possibly bearing at least: i) a hydroxyl group, ii) an amino group possibly substituted by one or two alkyl radicals in C rC3 possibly substituted, said alkyl radicals being able to form with the nitrogen atom to which they are attached, a heterocycle comprising 5 to 7 links, saturated or unsaturated possibly substituted possibly comprising at least one other heteroatom different or not from nitrogen, iii) a quaternary ammonium group -N+R'R”R'”, M for which R', R”, R'”, identical or different, represent a hydrogen atom, or a Ci-C4 alkyl group; and M represents the counterion of the corresponding organic acid, mineral, or halide, (iv) or a 5- or 6-membered heteroaryl radical possibly cationic, preferably imidazolium, and possibly substituted by a (C1-C4) alkyl radical, preferably methyl; * an acylamino radical (-NR-C(O)-R') in which the radical R is a hydrogen atom, an alkyl radical in Ci ^possibly bearing at least one hydroxyl group and the radical R' is an alkyl radical in Ci-C2; * a carbamoyl radical ((R)2N-C(O)-) in which the R radicals, identical or not, represent a hydrogen atom, a C1-C4 alkyl radical possibly bearing at least one hydroxyl group; * an alkylsulfonylamino radical (R'-S(O)2-N(R)-) in which the R radical represents a hydrogen atom, a C1-C4 alkyl radical possibly bearing at least one hydroxyl group, and the R' radical represents a C1-C4 alkyl radical, a phenyl radical; an aminosulfonyl radical ((R)2N-S(O)2-) in which the R radicals, whether identical or not, represent a hydrogen atom, a C1-C4 alkyl radical possibly bearing at least one hydroxyl group, * a carboxylic radical in acidic or salified form (preferably with an alkali metal or an ammonium, substituted or unsubstituted); * a cyano group; * a nitro or nitroso group; * a polyhaloalkyl group, preferably trifluoromethyl; The cyclic, cycloalkyl or heterocyclic part of a non-aromatic radical can be substituted by at least one substituent chosen from the following groups: * hydroxyl; * C1-C4 alkoxy, (poly)hydroxyalkoxy C2-C4; * C1-C4 alkyl; * alkylcarbonylamino (RC(O)-N(R')-) in which the radical R' is an atom of hydrogen, an alkyl radical in C1-C4 possibly bearing at least one hydroxyl group and the radical R is an alkyl radical in Ci-C2, amino possibly substituted by one or two identical or different alkyl groups in Ci-C4 themselves possibly bearing at least one hydroxyl group, said alkyl radicals being able to form with the nitrogen atom to which they are attached, a heterocycle comprising 5 to 7 links, saturated or unsaturated possibly substituted possibly comprising at least one other heteroatom different or not from nitrogen; * alkylcarbonyloxy (RC(O)-O-) in which the radical R is an alkyl radical in CrC4, amino group possibly substituted by one or two identical or different alkyl groups in CrC4 themselves possibly bearing at least one hydroxyl group, said alkyl radicals being able to form with the nitrogen atom to which they are attached, a heterocycle comprising 5 to 7 links, saturated or unsaturated possibly substituted possibly comprising at least one other heteroatom different or not from nitrogen; * alkoxycarbonyl (RGC(O)-) in which the radical R is a Ci-C4 alkoxy radical, G is an oxygen atom, or an amino group possibly substituted by a Ci-C4 alkyl group itself possibly bearing at least one hydroxyl group, said alkyl radical being able to form with the nitrogen atom to which they are attached, a heterocycle comprising 5 to 7 links, saturated or unsaturated possibly substituted possibly comprising at least one other heteroatom different or not from nitrogen; - a cyclic, cycloalkyl, heterocyclic radical, or a non-aromatic part of an aryl or heteroaryl radical, can also be substituted by one or more oxo groups; - a "cycloalkyl" radical is a mono- or bicyclic, hydrocarbon radical, comprising 3 to 10 carbon atoms, preferably 4 to 7 carbon atoms such as cyclopentyl, or cyclohexyl; - a "hydrocarbon" chain is unsaturated when it contains one or more double bonds and / or one or more triple bonds; - an "aryl" radical represents a mono- or polycyclic carbon group, condensed or not, comprising from 6 to 22 carbon atoms, and of which at least one ring is aromatic; preferentially the aryl radical is a phenyl, biphenyl, naphthyl, indenyl, anthracenyl, or tetrahydronaphthyl; - A "heteroaryl radical" represents a mono- or polycyclic group, condensed or not, possibly cationic, comprising 5 to 22 bonds, 1 to 6 heteroatoms chosen from nitrogen, oxygen, sulfur, and selenium atoms, and of which at least one ring is aromatic; preferably a heteroaryl radical is chosen from acridinyl, benzimidazolyl, benzobistriazolyl, benzopyrazolyl, benzo-pyridazinyl, benzoquinolyl, benzothiazolyl, benzotriazolyl, benzoxazolyl, py-ridinyl, tetrazolyl, dihydrothiazolyl, imidazopyridinyl, imidazolyl, indolyl, iso-quinolyl, naphthoimidazolyl, naphthooxazolyl, naphthopyrazolyl, oxadiazolyl, oxazolyl, oxazolopyridyl, phenazinyl, phenooxazolyl, pyrazinyl, pyrazolyl, pyrilyl, pyrazoyltriazyl, pyridyl, pyridinoimidazolyl, pyrrolyl, quinolyl, te-trazolyl, thiadiazolyl, thiazolyl, thiazolopyridinyl, thiazoylimidazolyl, thio-pyrylyl, triazolyl, xanthylyl and its ammonium salt; - a "heterocyclic radical" is a radical that can contain one or two unsaturations but is not aromatic, mono- or polycyclic, condensed or not, containing 5 to 22 links, comprising 1 to 6 heteroatoms chosen from the nitrogen, oxygen, sulfur and selenium atoms; - a "heterocycloalkyl radical" is a heterocyclic radical comprising at least one saturated ring; - a "cationic heteroaryl radical" is a heteroaryl group as defined above which includes an endocyclic or exocyclic quaternized cationic group, * When the cationic charge is endocyclic, it is taken up in the electron delocalization by mesomeric effect, for example this is a pyridinium, imi-dazolium or indolinium group: with R and R' being a heterorayl substituent as defined previously and particularly a (hydroxy)(Ci-C8)alkyl group such as methyl; * when the charge is exocyclic, for example it is an R+ ammonium or phosphonium substituent such as trimethylammonium, located outside the heteroaryl such as pyridinyl, indolyl, imidazolyl, or naphthalimidyl in question: with R a heteroaryl substituent as defined above and R+ an ammonium RaRbRcN+-, phosphonium RaRbRcP+- or ammonium RaRbRcN+-(Ci-C6 )alkylamino group with Ra, Rb and Rc identical or different represent a hydrogen atom or a (CrC8)alkyl group such as methyl; - a "cationic aryl with exocyclic charge" means an aryl ring whose quaternized cationic group is located outside said ring, this includes in particular R+ ammonium or phosphonium substituents such as trimethylammonium, located outside the aryl such as phenyl or naphthyl: - an "alkyl radical" is a hydrocarbon radical in Ci-C20, linear or branched, preferably in CrC8; - an "alkenylene radical" is an unsaturated hydrocarbon divalent radical as defined previously that can contain from 1 to 4 -C=C- double bonds, conjugated or not; particularly the alkenylene group contains 1 or 2 unsaturation(s); - the expression "possibly substituted" attributed to the alkyl radical implies that said alkyl radical can be substituted by one or more radicals chosen from among the radicals i) hydroxyl, ii) alkoxy in CrC4, iii) acylamino, iv) amino possibly substituted by one or two alkyl radicals, identical or different, in Ci-C4, said alkyl radicals being able to form with the nitrogen atom which bears them a heterocycle comprising 5 to 7 links, possibly including another heteroatom different or not from the nitrogen; (v) or a quaternary ammonium group -N+ r'r”r'” m where R', R”, R”', identical or different, represent a hydrogen atom, or an alkyl group in CrC4, or -N+R'R”R'” forms a heteroaryl such as imidazolium possibly substituted by an alkyl CrC4 group, and M represents the counterion of the corresponding organic acid, mineral or halide; - an "alkoxy radical" is an alkyl-oxy radical in which the alkyl radical is a hydrocarbon radical, linear or branched, preferably CrCi6; when the alkoxy group is possibly substituted, this implies that the alkyl group is possibly substituted as defined above; - by "organic or mineral acid salt" we mean more particularly salts selected from a salt derived from i) hydrochloric acid HCl, ii) hydrobromic acid HBr, iii) sulfuric acid H2SO4, iv) alkylsulfonic acids: Alk-S(O)2OH such as methylsulfonic acid and ethylsulfonic acid; v) arylsulfonic acids: Ar-S(O)2OH such as benzenesulfonic acid and toluenesulfonic acid; vi) citric acid; vii) succinic acid; viii) tartaric acid; ix) lactic acid, x) alkoxysulfinic acids: Alk-OS(O)OH such as methoxysulfinic acid and ethoxysulfinic acid; xi) aryloxysulfinic acids such as tolueneoxysulfinic acid and phenoxysulfinic acid; xii) phosphoric acid (H3PO4); xiii) acid acetic acid CH3C(O)OH; xiv) triflic acid CF3SO3H and xv) tetrafluoroboric acid HBF4; - by "anionic counter-ion" we mean an anion or anionic group derived from the salt of an organic or mineral acid counterbalancing the cationic charge of the dye; more particularly the anionic counter-ion is chosen from i) halides such as chloride, bromide; ii) nitrates; iii) sulfonates among which the Ci-C6 alkylsulfonates: Alk-S(O)2O such as methylsulfonate or mesylate and ethylsulfonate; iv) arylsulfonates: Ar-S(O)2O such as benzenesulfonate and toluenesulfonate or tosylate; v) citrate; vi) succinate; vii) tartrate; viii) lactate; ix) alkyl sulfates: Alk-OS(O)O such as methysulfate and ethylsulfate; x) arylsulfates: Ar-OS(O)O such as benzene sulfate and toluene sulfate; xi) alkoxy sulfates: Alk-OS(O)2O such as methoxy sulfate and ethoxysulfate;xii) aryloxysulfates: Ar-OS(O)2O, xiii) phosphates: O=P(OH)2-O, O=P(O)2-OH, O=P(O)3, HO-[P(O)(O)]WP(O)(O)2 with w being an integer; xiv) acetate; xv) triflate; and xvi) borates such as tetrafluoroborate, xvii) disulfate (O=)2S(O)2 or SO42 and monosulfate HSO4; The anionic counterion, derived from the salt of an organic or mineral acid, ensures the electroneutrality of the molecule. Thus, it is understood that when the anion contains several anionic charges, the same anion can serve to ensure the electroneutrality of several cationic groups in the same molecule, or it can serve to... the electroneutrality of several molecules; for example polymers which comprise two cationic entities may contain either two "single-charged" anionic counter-ions or contain one "double-charged" anionic counter-ion such as (O=)2S(O )2 or O=P(O )2-OH; - moreover, the addition salts usable within the framework of the invention are in particular chosen from among the addition salts with a cosmetically acceptable base such as alkalizing agents as defined below as alkali metal hydroxides such as soda, potash, ammonia, amines or alkanolamines.
[0017] The process for treating keratin fibers according to the invention is preferably a process for the care and / or shaping of keratin fibers, in particular human keratin fibers such as hair.
[0018] More preferably, the process according to the invention is a process for the care / repair of keratin fibers, and more particularly of hair.
[0019] Advantageously, the process according to the invention is a non-coloring process. In other words, the process according to the invention does not allow the coloring of said keratin fibers. The process according to the invention does not involve the application of a sufficient quantity of dye(s), such as direct dyes, oxidation dyes, and / or pigments, to color said keratin fibers. Polymeric photoinitiator compounds a)
[0020] The process according to the invention comprises the application on said keratin fibers of at least one polymeric photo-initiator compound.
[0021] For the purposes of the present invention, "photo-initiator compound" means a compound capable of absorbing light and transforming itself by generating atoms or molecules exhibiting radical chemical reactivity (see, for example, Macromol. Rapid Commun. Christian Decker, 23, 1067-1093 (2002); Encyclopedia of Polymer Science and Technology, "photopolymerisation free radical"; ibid, "photopolymerisation, cationic"; Macromol. Symp. 143, 45-63 (1999)).
[0022] For the purposes of the present invention, "polymeric photoinitiator compound" means a photoinitiator compound comprising in its structure the repetition of several units from one or more recurring monomers.
[0023] Advantageously, the polymeric photo-initiator compounds a) according to the invention are different from photosensitizers.
[0024] For the purposes of this invention, "photosensitizer" means a compound capable of modifying the wavelength of light irradiation, thereby releasing energy that can be captured by a receiving compound.
[0025] Preferably, the polymeric photo-initiator compounds a) according to the invention comprise units of the following formula -O-CnH2n+i- with n an integer between 1 and 5, more preferably between 2 and 4, and at least one photoreactive group (i.e. that reacts to light, for example by absorption of light such as UV radiation).
[0026] More preferably, the polymeric photoinitiator compound(s) a) according to the invention comprise a main chain formed of units of formula -O-CnH2n+i- , with n an integer between 1 and 5 (or even between 2 and 4), and one or more photo-reactive groups chosen from among acetophenone groups, benzylketal groups, benzoin groups, phosphinic oxide type groups, benzophenone groups, thioxanthone groups, and mixtures thereof; more preferably from among thioxanthone groups.
[0027] More preferably, the polymeric photoinitiator compound(s) a) according to the invention are selected from 1,3-di({a-2-(phenylcarbonyl)benzoylpoly[oxy(l-methylethylene)]}oxy)-2,2-bis({a-2-(phenylcarbonyl)benzoylpoly[oxy(l-methylethylene)]}oxymethyl)propane (CAS number: 1003567-82-5), {a-2-(phenylcarbonyl)benzoylpoly(oxyethylene)-poly[oxy(l-methylethylene)]-poly(oxyethylene)} 2-(phenylcarbonyl)benzoate (CAS numbers: 1003557-16-1 and 1182753-56-5, for example sold under the reference Speed Cure 7005 - Benzophenone tetramer-type by Arkema), the 1,3-di({-[1-chloro-9-oxo-9h-thioxanthen-4-yl)oxy]acetylpoly[oxy(1-methylethylene)]}oxy)-2,2-bis({a-[1-chloro-9-oxo-9h-thioxanthen-4-yl)oxy]acetyl poly[oxy(l-methylethylene)]}oxymethyl)propane (CAS number: 1182755-49-2, for example sold under the reference Speed Cure 7010 - Polyol ester-type by Arkema, average molecular weight of 1839 g / mol), polybutylene glycol bis(4-benzoylphenoxy)acetate (CAS number: 515136-48-8, for example sold under the reference Omnipol BP by IGM Resin), bis(benzophenone-2-carboxylic acid) polyethylene glycol ester (CAS number: 1246194-73-9, for example sold under the reference Omnipol 2702 by IGM Resin), polybutyleneglycol bis(9-oxo-9H-thioxanthenyloxy)acetate (CAS number: 813452-37-8, for example sold under the references Omnipol TX and Omnipol BL 728 by IGM Resin), poly(ethyleneglycol) bis(p-dimethylamino benzoate) (CAS number: 71512-90-8, for example sold under the reference Omnipol AS A by IGM Resin),polyethylene glycol di([3-4[4-(2-dimethylamino-2-benzyl) (CAS number: 886463-10-1, for example sold under the reference Omnipol 910 by IGM Resin), the polymer 1,3-propanediol, 2-ethyl-2-(hydroxymethyl)- with oxirane, 4-(dimethylamino)benzoate (CAS number: 2067275-86-7, for example sold under the reference GENOPOL* AB-2 by Rahn AG), and mixtures thereof.
[0028] The polymeric photoinitiator compound(s) a) according to the invention can also be chosen from the benzophenone derivative marketed under the reference GENOPOL BP-2 by Rahn AG, the thioxanthone derivative marketed under the reference GENOPOL TX-2 by Rahn AG, and their mixtures.
[0029] Preferably, the polymeric photoinitiator compound(s) a) according to the invention have a weight average molecular weight greater than or equal to 600g / mol, more preferably a molecular weight in the range of 700 to 3000 g / mol, better of 1000 to 2000 g / mol.
[0030] The mass distribution of the polymeric photoinitiator compound(s) a) is measured by SEC MALS analysis (SEC: Size Exclusion Chromatography - MALS: Multi-Angle Laser Scattering in English) using an HPLC chromatograph, in order to obtain the actual values, expressed in g / mol.
[0031] Preferably, the content of polymeric photoinitiator compound(s) a) in the composition containing it / them is in the range of 0.001 to 10% by weight, more preferably from 0.01 to 8% by weight, more preferably from 0.1 to 5% by weight, better from 0.2 to 2% by weight, relative to the total weight of the composition containing it / them. Non-colorable crosslinkable compounds b)
[0032] The process according to the invention comprises the application on said keratin fibers of at least one crosslinkable non-coloring compound.
[0033] For the purposes of the present invention, a "non-coloring compound" means a compound that does not allow the coloring of said keratin fibers. A non-coloring compound according to the invention is different from direct dyes, oxidation dyes (base and oxidation couplers), and pigments.
[0034] For the purposes of the present invention, "crosslinkable non-color compound" means a non-color compound, polymeric or non-polymeric, comprising one or more crosslinkable functions and capable of forming one or more three-dimensional networks by the establishment, by chemical means (for example under the action of at least one photoinitiator a) ) and / or under the action of light radiation, of bridges between the macromolecular chains.
[0035] The crosslinkable non-color compound(s) b) according to the invention may preferably be chosen from non-polymeric crosslinkable non-color compounds, polymeric crosslinkable non-color compounds, and mixtures thereof, better from polymeric crosslinkable non-color compounds.
[0036] More preferably, the non-color crosslinkable compound(s) b) according to the invention comprise at least one crosslinkable function preferably selected from the (meth)acrylate, vinyl and / or thiol functions.
[0037] Advantageously, the non-polymeric crosslinkable non-color compound(s) may be selected from non-polymeric crosslinkable non-color compounds comprising at least one crosslinkable function, preferably selected from (meth)acrylate, vinyl and / or thiol functions.
[0038] More preferably, the non-polymeric, crosslinkable, non-colorant compound(s) are selected from pentaerythritol tetrakis(3-mercaptopropionate), di(ethylene glycol) divinyl ether, linseed oil, argan oil, jojoba oil, 2-oleamido-l,3-octadecanediol, beta-carotene, ceramides, olive oil, vitamin F, sesame oil, apricot oil, coriander oil, echium plantagineum oil, sunflower oil, camelina sativa oil, oleic acid, dilinoleic acid, rapeseed oil, soybean oil, limnanthes alba oil, kukui oil, chaulmoogra oil, hemp oil, tung oil, corn oil, triethoxyvinylsilane, allyltriethoxysilane, trimethoxy(7-octen-l-yl)silane, itaconic acid, diallyl maleic ester, and mixtures thereof.
[0039] Preferably, the crosslinkable non-color compounds b) are chosen from polymeric crosslinkable non-color compounds.
[0040] The non-color crosslinkable polymeric compounds usable according to the invention can be siliconed or non-siliconized.
[0041] Advantageously, the polymeric crosslinkable non-color compound(s) may be selected from polymeric crosslinkable non-color compounds comprising at least one crosslinkable function, preferably selected from the (meth)acrylate, vinyl and / or thiol functions.
[0042] Among the non-color crosslinkable polymeric compounds, one can cite non-color crosslinkable polymeric compounds comprising one or more photodimerizable groups.
[0043] For the purposes of this invention, a "photodimerizable" group is defined as a chemical group that undergoes photodimerization reactions under irradiation. In the context of this invention, photodimerization is a chemical reaction between two double bonds (of the 2+2 type) or two pairs of double bonds (of the 4+4 type), and more particularly between two double bonds (of the 2+2 type).
[0044] The case of a reaction between two double bonds can be schematically represented as follows: I * It
[0045] These photodimerization reactions are defined in the document “Advanced Organic Chemistry, J Marck, 4th edition, Wiley Interscience, NY 1992, p 855”.
[0046] Thus, the double bond, when photo-stimulated, generally when subjected to UV radiation, is able to react with another double bond by cyclization, with or without the presence of a photoinitiator or a chemical initiator.
[0047] The activation of this double bond is generally induced by the presence of an electron-withdrawing substituent in the alpha position of this photodimerizable double bond. Examples of electron-withdrawing substituents include aromatic rings, such as the phenyl group possibly substituted by one or more halogen atoms, or electron-withdrawing groups such as NO2, CN, R'-YC(Y')-, R'-C(Y')-Y-, R'-YC(Y')-Y-, R'-YS(O)2-, -S(O)2-Y-R', with R' representing a hydrogen atom or a (Ci-C4)alkyl group possibly substituted by one or more halogen atoms, Y, and Y', identical or different, representing an oxygen, sulfur, or NR atom, with R" representing a hydrogen atom or a (Ci-C6)alkyl group.
[0048] Preferably, the photodimerizable pendant groups usable according to the invention are chosen from the following monovalent radicals of formulas (I) and (II), as well as their geometric isomers: -4--A-4- b H} 7 ï, ■ | ( ) ¥=Z^ Ç||) / S / %. formulas (I) and (II) in which: - Y and Z independently designate a nitrogen atom or a C(R) group with R representing a hydrogen atom or a (Ci-C4)alkyl group such as methyl; - A represents a bond or a divalent group chosen from the radicals (Ci-C8)alkylene, arylene, heteroarylene, cycloalkylene, heterocycloalkylene, (thio)carbonyl, (C2-C8)alkenylenes and their combinations; - B represents a monovalent group chosen from among (CrC8)alkyl radicals, aryl radicals, possibly cationic heteroaryl radicals, cycloalkyl radicals, possibly cationic heterocycloalkyl radicals, (thio)carbonyl radicals, (C2-C8)alkenyl radicals and their combinations; - X represents a divalent group chosen from the radicals (C2-C8)alkylenes, arylene, heteroarylene, cycloalkylene, heterocycloalkylene, (thio)carbonyls, (C2-C8)alkenylenes and their combinations; - p represents an integer between 1 and 5 inclusively, in particular between 1 and 3, preferably p equals 1; - ^A^ represents the bond that connects the monovalent radical part to the rest of the molecule; And Each of the groups mentioned may possibly be substituted by one or more halogen atoms or groups chosen from among the (Ci-C6)alkyl, hydroxy, amino, (di)(Ci-C6)alkylamino, phenyl, carboxy, (Ci-C6)alkoxy, (Ci-C6)alkoxy(thio)carbonyls, hydrogeno(thio)-carbonyls, sulfonato ROS(O)2- or RS(O) 2-O-, amide RR'NC(O)- or RC(O)-N(R')- or acyl RC(O)-, ammonium RR'R”N+- with R, R', and R”, identical or different, representing a hydrogen atom or a (Ci-C4)alkyl group.
[0049] The dimerizable pendant groups according to the invention are in particular those cited in US patents 2,811,510, EP 0 313 220, EP 0 313 221, EP 092 901, GB 2 030 575 and GB 2 076 826, as well as in the articles "Chemical review Vol 83,5 1983, p 507" "Polym, Paint colour Journal 1988, 178, p 209" and "Current Trends in Polymer Pho-tochemistry, Ellis Morwood edition, NY, 1995".
[0050] By way of example, one can more specifically cite the photodi-merizable pendant groups chosen from the monovalent radicals of the following compounds: - stilbene, - styrylpyridinium (stilbazolium) with the formula and their geometric isomers: Or : - R1 and R3, identical or different, represent a halogen atom or a (Ci-C6)alkyl group; or two contiguous R1 or R3 groups together with the carbon atoms that bear it form a benzo group; - R2 represents the hydrogen atom, a (Ci-C6)alkyl group possibly substituted by one or more halogen atoms such as chlorine or hydroxy, preferably R2 represents a (Ci-C6)alkyl group such as methyl, ethyl, propyl; - q and r represent an integer between 0 and 4 inclusive; and - Q-, represents an anionic counter ion preferably chosen from ha-logenide ions such as chlorides, bromides, iodides, perchlorates, tetrafluoroborates, methyl sulfate, phosphates, sulfates, methanesulfonates, p-toluenesulfonate; - ^^|^,"I present the bond which links the monovalent radical part to the rest of the molecule, it being understood that the pendant group A2 can be linked to the rest of the molecule via R2; preferably the bond ^^^.^ is located on the phenyl in the para position of the styryl group on Ai or linked to the rest of the molecule via R2 on A2; preferably the styryl group of Ai and A2 is located in the para position of the pyridinium group; - styrylazolium with the formula and their geometric isomers: Or : - A represents a sulfur atom, an oxygen atom, or an NR2 or C(R2)2 group; and Q, r, q, R1, R2, and R3 being as defined previously, preferably the bond ^^^..is located on the phenyl in the para position of the group stryryle, - styrylpyrazine, - chalcone, - (thio)cinnamate and (thio)cinnamamide, - Malimides, - (thio)coumarin, - thymine, - uracil, - butadiene - anthracene, - pyridone, - pyrrolizinone, - acridizinium salts, - furanone, - phenylbenzoxazole, and - their derivatives.
[0051] According to a particular embodiment, the photodimerizable pendant group(s) are selected from: a) the photodimerizable group(s) bearing a stylbazolium function of formula (la) or (Ib) and their geometric isomers: R' X (the) in which: - R represents a hydrogen atom, a C1-C4 alkyl group or a C1-C4 hydroxyalkyl group; - R' represents a hydrogen atom or an alkyl group in C1-C4, and - X- denotes an anionic counter ion preferably chosen from among halide ions such as chlorides, bromides, iodides, perchlorates, tetrafluoroborates, methyl sulfate, phosphates, sulfates, methanesulfonates, p-toluenesulfonate; preferably the styryte group is located para to the py-ridinium group and / or para to the L bond. R* X (Ib) in which - R' ' denotes a divalent alkylene radical having from 2 to 8 carbon atoms, - R' represents a hydrogen atom or an alkyl group in Ci-C4, and - X having the same meaning as that described for the previous formula (the); - .^^.-^having the same meaning as before; preferably the styryre group is located para to the pyridinium group; Or b) photodimerizable groups bearing a styrylazolium function of formula (lia): R. X (lia) R .'-H"' * : in which: - Ri designates the hydrogen atom, an alkyl group in Ci-C4 or a hydroxyalkyl group in CrC4; - A denotes a sulfur atom, an oxygen atom, or an NR' or C(R') 2, R' group; with R' representing the hydrogen atom or a Ci-C4 alkyl group, R' preferably representing the hydrogen atom; and - X having the same meaning as that described for the previous formula (the); - ...^J-^-^having the same meaning as before; Preferably the styryre group is located on the phenyl group in the para position
[0052] Examples of hydrophobic pendant groups that can be used according to the invention include: - (Ci-C30)alkyl groups, saturated or unsaturated, possibly substituted and / or interrupted by one or more heteroatoms, - the alkenyl groups, - aryl groups such as phenyl, pyridyl, furyl, indoyl, benzofuryl, thiophenyl, imizadoyl, oxazoyl, thiazoyl, pyrazinyl, pyrimidinyl; - fluorinated groups such as fluorocarbon groups, such as -CF3, -CHF2, -OCF3, -SCF3, CF3C(O)-, - silicone groups such as -SiRaRbRc such as -Si(CH3)3, polydimethylsiloxane-PDMS, -Si(OR)3, PDMS α,co-diaminopropyl, PDMS α,co-dihydroxyalkyl, PDMS a,co-dicarboxyalkyl, with Ra, Rb and Rc, identical or different, representing a (Ci-C8)alkyl group possibly interrupted and / or terminated by one or more non-contiguous heteroatoms such as O, or S; and R representing a (Ci-C6)alkyl group.
[0053] Preferably the hydrophobic pendant group(s) are chosen from a (C2-C22)alkyl group, more preferably from a (C3-Ci6)alkyl group, better the (C3-Ci2)alkyl groups.
[0054] The backbone of the non-coloring polymer, comprising at least one photodimerizable pendant group and at least one hydrophobic pendant group, can be of various types. This polymer backbone can be natural or synthetic. Polysaccharides are examples of natural polymer backbones.
[0055] Examples of polysaccharides include xanthan gum, carrageenan, chitosan, cellulose and its derivatives, alginate, starch, dextran, pullulan, galactomannan and their biologically acceptable salts, as well as their derivatives.
[0056] Examples of synthetic skeletons include poly(vinyl) polymers and polydiorganosiloxanes.
[0057] Among the poly(vinyl) polymers, we can mention poly(vinyl acetate) (PVA), partially or totally hydrolyzed and polyvinyl alcohol.
[0058] As regards polymers having photodimerizable pendant groups bearing a stylbazolium function, they are obtained by reaction of the polymer in question with a chemical entity comprising a group of formula (la) or (Ib).
[0059] Preferably, the chemical entity comprising a group (la) carries a reactive group W of the aldehyde or acetal type.
[0060] Examples of chemical entities that can be used to graft styrylpyridinium-type groups include quaternary salts of 2-(4-formylstyryl)-pyridinium, 4-(4-formyl-styryl)-pyridinium, 2-(3-formylstyryl)-pyridinium, N-methyl-2-(4-formylstyryl)pyridinium, N-methyl-3-(4-formylstyryl)-pyridinium, N-methyl-2-(3-formylstyryl)-pyridinium, N-methyl-2-(2-formylstyryl)pyridinium, N-ethyl-2-(4-formyl-styryl)-pyridinium, N-(2-hydroxyethyl)-2-(4-formylstyryl)-pyridinium, N-(2-hydroxyethyl)-4-(4-formylstyryl)-pyridinium, N-methyl-4-(4-formylstyryl)-pyridinium, N-methyl-4-(3-formylstyryl)-pyridinium.
[0061] The quaternary salts of pyridinium can be chloride, bromide, iodide, perchlorate, tetrafluoroborate, methosulfate, phosphate, sulfate, methanesulfonate, and p-toluenesulfonate salts. Such chemical entities are described in GB-A-2030575.
[0062] Examples of entities include 4-(4-formylphenylethenyl)l-methylpyridinium methosulfate, l-(3-ethoxycarbonylmethyl)-4-[2-(4-formylphenyl)ethenyl]pyridinium bromide,
[0063]
[0064] l-(methoxycarbonylpropyl)-4-[2-(4-formylphenyl)ethenyl]pyridinium bromide. Such entities are described in US 2007 / 0112094. Preferably, n-methyl-4-(4-formylstyryl)pyridinium methylsulfate (RN= 74401-04-0) is used, notably marketed by the company WAKO. The synthesis, described below, of these polymers functionalized with photodimerizable groups such as those comprising a styryl group and hydrophobic groups is feasible by following the protocol of T. Uhlich et al. (Reactive & Functional Polymers, 28, 55-40 (1995)). jvrj W Compounds of formula (III) to (VIII') in which, - R, identical or different, represents a hydrogen atom, or a (Ci-Ci0)alkyl group, possibly substituted and / or interrupted by one or more heteroatoms, preferably R represents a hydrogen atom or a (Ci-C4)alkyl group such as methyl, ethyl, or propyl, more preferably R represents a hydrogen atom; - R1 represents a hydrogen atom, or a (Ci-Cio)alkyl group, possibly substituted and / or interrupted by one or more heteroatoms, preferably R1 represents a hydrogen atom or a (Ci-C4)alkyl group; - R2 represents a (Ci-C30)alkyl group, saturated or unsaturated, possibly substituted and / or interrupted by one or more heteroatoms, an alkenyl group, an aryl group such as phenyl, pyridyl, furyl, indoyl, benzofuryl, thiophenyl, imizadoyl, oxazoyl, thiazoyl, pyrazinyl, pyrimidinyl; a fluorinated group such as a fluorocarbon group such as -CF3, -CHF2, -OCF3, -SCF3, CF3C(O)- a silicone group such as -SiRaRbRc such as -Si(CH3)3, polydimethylsiloxane-PDMS, -Si(OR)3, PDMS α,co-diaminopropyl, PDMS α,co-dihydroxyalkyl, PDMS α,co-dicarboxyalkyl, with Ra, Rb and Rc, identical or different, representing a (Ci-C8)alkyl group optionally interrupted and / or terminated by one or more non-contiguous heteroatoms such as O, or S; and R representing a (Ci-C6)alkyl group; preferably R2 represents a (C2-C22)alkyl group, more preferably (C3-Ci6)alkyl; - A represents a group derived from a photodimerizable compound, preferably styrylpy-ridinium such as (I), (II), (Ai), (A2), (la), (Ib) or (lia) as defined above, more particularly chosen from (AJ or (la) as defined above; - X represents an oxygen atom or a sulfur atom, preferably oxygen; - X', and X”, represent an oxygen atom, sulfur atom or an N(R3) group with R3 representing a hydrogen atom or a (Ci-C4)alkyl group, preferably X' and X” represent an oxygen atom; Most of the products obtained have the formula (VI).
[0065] Advantageously, these chemical entities react with a polyvinyl alcohol or polyvinyl acetal type polymer as described in the documents cited above and also such as polymer (III) described in the diagram above for which X, X' and X” represent an oxygen atom, R and R1 being as described above.
[0066] For example, a polyvinyl alcohol grafted polymer having the following structural motifs is thus obtained, A representing a group (I), (AJ or (la): Oh oh HAS
[0067] Polyvinyl alcohol polymers grafted with stryrylpyridinium groups are described in particular in the publication Ichimura K et al, Preparation and Characteristics of photocross-linkable poly(vinyl alcohol), Journal of polymer science, polymer chemistry edition, Vol 20, 1419-1432 (1982).
[0068] The polymers can be obtained by reaction of partially hydrolyzed polyvinyl alcohol or polyvinyl acetate with formyl or acetal group styrylpyridinium salts as described in GB-A-2030575, WO 96 / 29312, US 5061603, GB-A-2076826, EP-A-092901.
[0069] Cellulose polymers grafted with styrylpyridinium groups are notably described in US 2007 / 0112094.
[0070] Preferably, the chemical entity comprising a (AJ) group or (the) carries a reactive group which is a halogen atom such as chlorine.
[0071] In this variant, the chemical entity corresponds, for example, to the formula:
[0072] Advantageously, the crosslinkable polymer comprising the (Ib) groups is obtained for example by reaction of the above entity with the polysaccharide chosen from those defined previously.
[0073] For their part, polymers having photodimerizable groups bearing a styrylazolium function are obtained by reaction of the polymer with a chemical entity comprising a group of formula (lia).
[0074] Preferably, the chemical entity comprising a (lia) group carries a reactive W group of the aldehyde or acetal type.
[0075] Examples of chemical entities that can be used to graft styrylazolium-type groups include those described in EP-A-313220.
[0076] Advantageously, these chemical entities react with a polyvinyl alcohol or polyvinyl acetal type polymer as described in the documents cited above.
[0077] A polyvinyl alcohol grafted polymer comprising motifs of the following structure is thus obtained: with B corresponding to the group or (lia) as defined previously:
[0078] Polyvinyl alcohol polymers grafted with styrylazolium groups are described in particular in EP-A-313220. In that document, these polymers can be obtained by reaction of polyvinyl alcohol or polyvinyl acetate partially hydrolyzed with styrylazolium salts with aldehyde or acetal group.
[0079] According to one embodiment, the polymer bearing photodimerizable group(s) and hydrophobic group(s) is in the form of particles, in particular dispersed particles. Thus, in the latter case, the polymer particles are more particularly polyvinyl alcohol particles.
[0080] According to a preferred embodiment, the polymer bearing photodi-merizable group(s) and hydrophobic group(s) of the invention is soluble in the cosmetic medium.
[0081] Thus, according to one embodiment, the polymer is a polyvinyl acetate (PVA) type polymer partially functionalized by one or more hydroxyl function(s) and one or more function(s) of formula (IX): (IX)
[0082] The degree of polymerization of PVA can be between 100 and 5000 and the rate of substitution, in % of functions of formula (I) as defined above, can be between 0.1 and 25.
[0083] The following diagram represents a variant where the polymer is the polymer (III) as defined above bearing functions grafted by stylbazolium entities such as those of formula (Al) as defined above, which is capable of crosslinking under the effect of light, as illustrated below.
[0084] These materials react to radiation which may include both a UV light component and a visible light component, in particular a low dose of UV.
[0085] Preferably, the following diagram represents the polymer which is PVA-SbQ (PVAcetate type polymer bearing some hydrolyzed functions and some functions grafted by stylbazolium entities), which is able to crosslink under the effect of light, with or without photoinitiator, as illustrated below.
[0086] These materials are particularly appreciated because they can react to radiation that may include both a UV light component and a visible light component, in particular a low dose of UV.
[0087] Pendant groups having reactivity in both UV and visible light are preferred.
[0088] According to another variant, the crosslinkable polymer is represented by a natural polymer which is functionalized by photodimerizable groups.
[0089] This may in particular be a polysaccharide, which may in particular be selected from chondroitin sulfate, keratan, keratan sulfate, heparin, sulfate
[0090]
[0091]
[0092]
[0093]
[0094]
[0095] heparin, xanthan gum, carrageenan, hyaluronic acid, chitosan, cellulose and its derivatives, alginate, starch, dextran, pullulan, galactomannan and their biologically acceptable salts. The degree of functionalization is of course adjusted to be able to confer the required degree of cross-linking upon activation. According to the invention, the degree of functionalization in photodimerizable pattern is at least 0.1%, or even at least 0.5%, or even at least 2%. Preferably, the photodimerizable groups are carried by a polyvinyl acetate or polysaccharide type polymer. A single polymer can be used, bearing photodimerizable pendant groups of different or similar natures. Alternatively, a mixture of polymers with different functionalities can be used. Consequently, reactions can occur between two photodimerizable groups of the same or different chemical natures. Activated double bonds can react with another double bond of the same chemical nature or with another double bond of a different chemical nature. As an example of a polymer usable in the invention, one may cite the partially or totally hydrolyzed polyvinyl acetate polymer comprising the units below, in particular the polymer called PVA-SbQ-propyl in which the amount of SbQ motif is between, inclusive, 0.5% and 6% molar, preferably between 1.5% and 5% molar, the amount of propyl group is between, inclusive, 2% and 20% molar, preferably between 5% and 15% molar, better from 8% to 12%, the amount of hydroxyl group is between, inclusive, 50% and 97.5% molar, preferably between 60% and 97.5% molar, better from 80% to 90% molar: H CO s CH CH; OH --CH---CH. with Q, represents an anionic counter-ion, preferably chosen from among the ha- ions lo-nides such as chlorides, bromides, iodides, perchlorates, tetrafluoroborates, methyl sulfate, phosphates, sulfates, methanesulfonates, p-toluenesulfonate, more preferentially mesylate CH3OSO3.
[0096] According to a particular embodiment, the molecular weight Mw of PVA is between 10,000 and 100,000 g / mol, preferably between 15,000 and 80,000 g / mol, more particularly from 20,000 to 50,000, even better from 25,000 to 35,000 g / mol.
[0097] According to a particular embodiment, the molecular weight Mw of PVA is on the order of 27000 g / mol.
[0098] As examples of non-color crosslinkable polymeric silicone compounds, one can also mention in particular the polymers comprising acryloxypropylmethylsiloxane units marketed under the reference UMS 182 by the company Gelest.
[0099] Preferably, the polymeric crosslinkable non-coloring compounds b) are selected from (mercaptopropyl)methylsiloxane / dimethylsiloxane copolymers (e.g., SMS-022 or SMS-042 from Gelest), (mercaptopropyl)methylsiloxane homopolymers (e.g., SMS-992 from Gelest), organopolysiloxanes with side chains comprising at least one mercapto group (e.g., KF-2001 or KF-2004 from Shin-Etsu), polysiloxanes with (meth)acrylic groups, (acryloxypropyl)methylsiloxane / dimethylsiloxane copolymers, polyquaternium-114, and mixtures thereof. More preferably, the polymeric crosslinkable non-coloring compound b) is polyquaternium-114.
[0100] Preferably, the crosslinkable non-coloring compound(s) b) are selected from pentaerythritol tetrakis(3-mercaptopropionate), di(ethylene glycol) divinyl ether, linseed oil, argan oil, jojoba oil, 2-oleamido-l,3-octadecanediol, beta-carotene, ceramides, olive oil, vitamin F, sesame oil, apricot oil, coriander oil, echium plantagineum oil, sunflower oil, camelina sativa oil, oleic acid, dilinoleic acid, rapeseed oil, soybean oil, meadowfoam oil, kukui oil, chaulmoogra oil, hemp oil, oil of tung, corn oil, triethoxyvinylsilane, allyltriethoxysilane, trimethoxy(7-octen-l-yl)silane, itaconic acid, diallyl maleic ester, (mercaptopropyl)methylsiloxane / dimethylsiloxane copolymers (e.g., SMS-022 or SMS-042 from Gelest),homopolymers (mercaptopropyl)methylsiloxane (e.g., SMS-992 from Gelest), organopolysiloxanes with side chains containing at least one mercapto group (e.g., KF-2001 or KF-2004 from Shin-Etsu), polysiloxanes with (meth)acrylic groups, (acryloxypropyl)methylsiloxane / dimethylsiloxane copolymers, polyquaternium-114, and mixtures thereof.
[0101] More preferably, the crosslinkable non-colorant compound(s) b) are selected from linseed oil, polyquaternium-114, and chain organopolysiloxanes laterals comprising at least one mercapto group (for example KF-2001 or KF-2004 from Shin-Etsu), polysiloxanes with (meth)acrylic groups, and their mixtures.
[0102] Even better, the crosslinkable non-color compound(s) b) are chosen from among the crosslinkable non-color compounds b) polymeric, and in particular chosen from polyquaternium-114, organopolysiloxanes with side chains having at least one mercapto group (for example KF-2001 or KF-2004 from Shin-Etsu), polysiloxanes with (meth)acrylic groups, and mixtures thereof; or even, the crosslinkable non-color compound b) is polyquaternium-114.
[0103] Preferably, the content of crosslinkable non-color compound(s) b) in the composition containing it / them is in the range of 0.01 to 40% by weight, more preferably 0.1 to 30% by weight, more preferably 0.5 to 25% by weight, better 1 to 25% by weight, relative to the total weight of the composition containing it / them.
[0104] Preferably, the content of non-color crosslinkable polymeric compound(s) b) in the composition containing it / them is in the range of 0.01 to 40% by weight, more preferably 0.1 to 30% by weight, more preferably 0.5 to 25% by weight, better 1 to 25% by weight, relative to the total weight of the composition containing it / them.
[0105] Preferably, the polyquaterium-114 content in the composition containing it is in the range of 0.01 to 40% by weight, more preferably 0.1 to 30% by weight, more preferably 0.5 to 25% by weight, better 1 to 25% by weight, relative to the total weight of the composition containing it.
[0106] Preferably, the content of non-polymeric crosslinkable non-colorant compound(s) b) in the composition containing it / them is in the range of 0.01 to 40% by weight, more preferably 0.1 to 30% by weight, more preferably 0.5 to 25% by weight, better 1 to 25% by weight, relative to the total weight of the composition containing it / them.
[0107] During step (i) of the process according to the invention, the polymeric photoinitiator compound(s) and the crosslinkable non-colorant compound(s) may be included in the same composition (C) or in at least two separate compositions (A) and (B).
[0108] When the polymeric photoinitiator compound(s) and the crosslinkable non-colorant compound(s) are included in several separate compositions, the compositions comprising them may be applied simultaneously or sequentially; preferably simultaneously. Compositions (A) and (B) may optionally be mixed immediately before application (extemporaneously) to obtain composition (C).
[0109] According to a particular embodiment of the invention, step (i) of the keratin fiber treatment process corresponds to: (i) application to said keratin fibers, simultaneously or sequentially: - of a composition (A) comprising at least one polymeric photoinitiator compound (a), and - of a composition (B) comprising at least one crosslinkable non-colorant compound b).
[0110] According to this embodiment, composition (A) can be applied to said keratin fibers before or after the application of composition (B); preferably, composition (A) is applied to said keratin fibers before the application of composition (B). More preferably, the process does not include a step of rinsing said keratin fibers between the applications of compositions (A) and (B).
[0111] Preferably, the polymeric photoinitiator compound(s) and the crosslinkable non-colorant compound(s) are contained in a single composition (C). In other words, step (i) of the process for treating keratin fibers preferably corresponds to the application to said keratin fibers of a composition (C) comprising at least one polymeric photoinitiator compound (a) and at least one crosslinkable non-colorant compound (b), as described above. More preferably, composition (C) is anhydrous.
[0112] Preferably, the composition(s) (A), (B) and / or (C) implemented in step (i) of the process according to the invention comprise, independently of each other, in addition at least one vehicle, more preferably chosen from fats, water, and mixtures thereof. Fats
[0113] Preferably, the composition or compositions implemented in step (i) of the process according to the invention may, independently of each other, further comprise at least one fatty substance.
[0114] For the purposes of this invention, "fatty substance" means an organic compound insoluble in water at 25°C and atmospheric pressure (760 mm Hg, i.e. 1.013.105 Pa), i.e., with a solubility in water of less than 5% (in g / mL of water) and preferably less than 1%, even more preferably less than 0.1%.
[0115] For the purposes of the invention, non-siliconized fats comprise from 6 to 60 carbon atoms, preferably from 7 to 60 carbon atoms, more preferably from 7 to 40 carbon atoms, better from 8 to 40 carbon atoms.
[0116] Fatty substances are generally soluble in organic solvents under the same conditions of temperature and pressure, such as chloroform, ethanol, benzene, petroleum jelly or decamethylcyclopentasiloxane.
[0117] Advantageously, the fat or fats are chosen from among liquid fats.
[0118] For the purposes of this invention, "liquid fats" means a fat in a liquid state at 25°C and atmospheric pressure (760 mm Hg, i.e. 1.013.105 Pa).
[0119] They preferably have a viscosity less than or equal to 2 Pa.s, better less than or equal to 1 Pa.s and even better less than or equal to 0.1 Pa.s at a temperature of 25 °C and at a shear rate of 1 s1.
[0120] The fats usable in the composition according to the invention are preferably not oxyalkylated, and preferably do not contain a carboxylic acid COOH (or carboxylate -COO) function.
[0121] The fats that can be used in the composition according to the invention are different from the crosslinkable non-color compounds b), as described above.
[0122] Advantageously, the fats according to the invention can be chosen from hydrocarbons, silicone oils, fatty alcohols preferably comprising from 6 to 60 carbon atoms (more preferably from 7 to 60 carbon atoms, more preferably from 7 to 40 carbon atoms, better from 8 to 40 carbon atoms), fatty esters preferably comprising from 6 to 60 carbon atoms (more preferably from 7 to 60 carbon atoms, more preferably from 7 to 40 carbon atoms, better from 8 to 40 carbon atoms), fatty ethers preferably comprising from 6 to 60 carbon atoms (more preferably from 7 to 60 carbon atoms, more preferably from 7 to 40 carbon atoms, better from 8 to 40 carbon atoms), and mixtures thereof.
[0123] By "liquid hydrocarbon" is meant a hydrocarbon composed solely of carbon and hydrogen atoms, liquid at 25°C and at atmospheric pressure (760 mm Hg, i.e. 1.013 x 1005 Pa), of mineral or vegetable or synthetic origin.
[0124] More particularly, the hydrocarbons can be chosen from C6-C16 hydrocarbons or hydrocarbons with more than 16 carbon atoms and up to 60 carbon atoms, and in particular alkanes, oils of animal origin, oils of vegetable origin, glycerides or fluorinated oils of synthetic origin, fatty alcohols, esters of fatty acids and / or fatty alcohols, silicones.
[0125] Advantageously, the fat or fats are chosen from among non-siliconized fats.
[0126] It is recalled that, for the purposes of the invention, alcohols, esters, and fatty ethers more particularly have one or more hydrocarbon groups, linear or branched, saturated or unsaturated, comprising from 6 to 60 carbon atoms (more preferably from 7 to 60 carbon atoms, more preferably from 7 to 40 carbon atoms, better still from 8 to 40 carbon atoms), optionally substituted, in particular by one or more hydroxyl groups OH (in particular from 1 to 4 hydroxyl groups). If they are unsaturated, these compounds may comprise one to three unsaturations, of preference of 1 to 3 carbon-carbon double bonds, conjugated or not.
[0127] With regard to C6-Ci6 alkanes, these may be linear or branched, possibly cyclic. Preferably, the usable fat(s) are chosen from among linear or branched C8-Ci4 alkanes, more preferably C9-Ci3, and even more preferably C9-Ci2. Examples include hexane, undecane, dodecane, tridecane, and isoparaffins such as isohexadecane, isodecane, or isododecane. Linear or branched hydrocarbons with more than 16 carbon atoms may be chosen from paraffin oils, petrolatum, polydecenes, and hydrogenated polyisobutene such as Parleam®.
[0128] Among usable fats having an overall solubility parameter according to the HANSEN solubility space less than or equal to 20 (MPa)1 / 2, we can mention oils, which can be chosen from natural or synthetic, hydrocarbon, possibly fluorinated, possibly branched oils, alone or in mixture.
[0129] According to an advantageous embodiment, the composition(s) applied in step (i) comprises at least one fatty substance selected from hydrocarbon oils. The oil(s) may be volatile or non-volatile.
[0130] The hydrocarbon oil(s) may be chosen from: * hydrocarbon oils having 8 to 14 carbon atoms, and in particular: - C8-Ci4 branched alkanes such as petroleum-derived C8-Ci4 isoalkanes (also called isoparaffins) such as isododecane (also called 2,2,4,4,6-pentamethylheptane), isodecane, and for example oils sold under the trade names Isopars' or Permetyls, - linear alkanes, for example such as n-dodecane (C12) and n-tetradecane (C14) sold by Sasol under the references PARAFOL 12-97 and PARAFOL 14-97 respectively, as well as their mixtures, the undecane-tridecane mixture, the mixtures of n-undecane (Cl 1) and n-tridecane (Cl3) obtained in examples 1 and 2 of application WO 2008 / 155059 of Société Cognis, and their mixtures as well as the mixtures of n-undecane (C11) and n-tridecane (Cl3) Cetiol Ultimate® of BASF. * Short-chain esters (having 3 to 8 carbon atoms in total) such as ethyl acetate, methyl acetate, propyl acetate, n-butyl acetate * vegetable hydrocarbon oils, other than crosslinkable non-coloring compounds b) possibly present in the composition containing them, such as triglycerides consisting of fatty acid esters and glycerol, the fatty acids of which may have chain lengths ranging from C4 to C24, the latter being linear or branched, saturated or unsaturated; these oils include, in particular, triglycerides of heptanoic acid or octanoic acid, or even wheat germ, sunflower, grapeseed, sesame, oils corn, apricot, castor, shea, avocado, olive, soy, sweet almond, palm, rapeseed, cotton, hazelnut, macadamia, jojoba, alfalfa, poppy, pumpkin, sesame, squash, rapeseed, blackcurrant, evening primrose, millet, barley, quinoa, rye, safflower, candlenut, passionflower, rosehip, coconut; shea butter; or caprylic / capric acid triglycerides such as those sold by Stéarineries Dubois or those sold under the names Miglyol 810®, 812® and 818® by Dynamit Nobel, * synthetic ethers having 10 to 40 carbon atoms; * linear or branched hydrocarbons, of mineral or synthetic origin such as petrolatum, polydecenes, hydrogenated polyisobutene such as Parleam®, squalane, paraffin oils, and mixtures thereof, * esters such as oils with the formula R'C(O)-O-R2 in which R1 represents the remainder of a linear or branched fatty acid containing 1 to 40 carbon atoms and R2 represents a hydrocarbon chain, particularly a branched one, containing 1 to 40 carbon atoms, provided that R1 + R2 is >10, such as Purcellin oil (cetostearyl octanoate), isopropyl myristate, isopropyl palmitate, benzoates of alcohols in C12 to C15, hexyl laurate, diisopropyl adipate, isononyl isononanoate, 2-ethylhexyl palmitate, isostearyl isostearate, 2-hexyldecyl laurate, 2-octyldecyl palmitate, myristate 2-Octyl-dodecyl, heptanoates, octanoates, decanoates or ricinoleates of alcohols or polyalcohols such as propylene glycol dioctanoate; hydroxylated esters such as isostearyl lactate, di-isostearyl malate, 2-octyl-dodecyl lactate;polyol esters and pentaerythritol esters, more preferably linear or branched C8-Ci0 fatty acid esters and linear or branched Ci2-Ci8 fatty alcohol esters alone or in mixture with alkanes from the complete hydrogenation / reduction of fatty acids from Cocos Nucifera (Coconut) oil, particularly dodecane or cococaprylate / caprate mixtures with dodecane, such as those with the INCI name coconut alkanes (and) Coco-caprylate / caprate marketed under the name VEGELIGHT 1212LC® by Grant Industries. * fatty alcohols with branched and / or unsaturated carbon chains having 12 to 26 carbon atoms such as octyl dodecanol, isostearyl alcohol, oleic alcohol, 2-hexyldecanol, 2-butyloctanol, and 2-undecylpentadecanol.
[0131] Advantageously, the fats can be chosen from silicone oils, in particular volatile silicone oils, non-volatile silicone oils, and mixtures thereof.
[0132] Examples of volatile silicone oils include volatile linear or cyclic silicone oils, in particular those having a viscosity less than or equal to 8 centistokes (cSt) (8 x 10⁶ m² / s), and having, in particular, from 2 to 10 silicon atoms, and in in particular, of 2 to 7 silicon atoms, these silicones possibly comprising alkyl or alkoxy groups having from 1 to 10 carbon atoms. As volatile silicone oils usable in the invention, one can cite, in particular, dimethicones of viscosity 5 and 6 cSt, octamethyl cyclotetrasiloxane, decamethyl cyclopentasiloxane, dodecamethyl cyclohexasiloxane, heptamethyl hexyltrisiloxane, heptamethyloctyl trisiloxane, hexamethyl disiloxane, octamethyl trisiloxane, decamethyl tetrasiloxane, dodecamethyl pentasiloxane, tetradecamethyl hexasiloxane, and mixtures thereof.
[0133] Examples of non-volatile silicone oils include non-volatile linear or cyclic polydimethylsiloxanes (PDMS); polydimethylsiloxanes containing alkyl, alkoxy, amino and / or phenyl groups, during or at the end of the silicone chain, groups having from 2 to 24 carbon atoms; phenyl silicones such as phenyl trimethicones, phenyl dimethicones, phenyl trimethylsiloxy diphenyl siloxanes, diphenyl dimethicones, diphenyl methyldiphenyl trisiloxanes, 2-phenyl ethyl trimethylsiloxysilicates and pentaphenyl silicone oils.
[0134] Particularly preferred silicone oils are chosen from among C8-C40 alkyl-amodimethicones, volatile silicone oils, and mixtures thereof; more preferably from volatile silicone oils; and even better from dimethicones of viscosity 5 and 6 cSt, octamethyl cyclotetrasiloxane, decamethyl cyclopentasiloxane, dodecamethyl cyclohexasiloxane, dodecamethyl pentasiloxane, tetradecamethyl hexasiloxane, and mixtures thereof.
[0135] Preferably, the content of silicone oil(s) is less than or equal to 10% by weight relative to the weight of the composition containing it(s), more particularly less than or equal to 5% by weight and more preferably less than or equal to 2% by weight, relative to the total weight of the composition containing it(s).
[0136] Preferably, the content of volatile silicone oil(s) is less than or equal to 10% by weight relative to the weight of the composition containing it, more particularly less than or equal to 5% by weight and more preferably less than or equal to 2% by weight, relative to the total weight of the composition containing it or them.
[0137] Preferably, the fat or fats are chosen from C6-C60 hydrocarbons, silicone oils, C8-C40 fatty alcohols, C8-C40 fatty esters, C8-C40 fatty ethers, and mixtures thereof.
[0138] More preferably, the fat or fats are chosen from among C6-Ci6 alkanes, C16-C6o hydrocarbons, silicone oils, C8-C40 fatty alcohols, C8-C40 fatty esters, C8-C40 fatty ethers, and mixtures thereof.
[0139] More preferably, the fatty substance(s) are chosen from hexane, undecane, dodecane, tridecane, isohexadecane, isododecane, isodecane, octyldodecanol, isostearyl alcohol, 2-hexyldecanol, isononanoate isononyl, ethyl palmitate, isopropyl palmitate, isopropyl myristate, ethyl myristate, isocetyl stearate, ethyl laurate, 2-ethylhexyl isononanoate, ethyl octanoate, ethyl caprate, isodecyl neopentanoate, isostearyl neopentanoate, bis-cetearyl amodimethicone, 5 and 6 cSt viscosity dimethicones, octamethyl cyclotetrasiloxane, decamethyl cyclopentasiloxane, dodecamethyl cyclohexasiloxane, dodecamethyl pentasiloxane, tetradecamethyl hexasiloxane, and mixtures thereof.
[0140] Even better, the fat or fats are chosen from hexane, undecane, dodecane, tridecane, isohexadecane, isododecane, isodecane, octyldodecanol, isostearyl alcohol, 2-hexyldecanol, isononyl isononanoate, ethyl palmitate, isopropyl palmitate, isopropyl myristate, ethyl myristate, isocetyl stearate, ethyl laurate, 2-ethylhexyl isononanoate, ethyl octanoate, ethyl caprate, isodecyl neopentanoate, isostearyl neopentanoate, bis-cetearyl amodimethicone, and mixtures thereof.
[0141] According to a particular embodiment of the invention, the composition(s) (A), (B) and / or (C) implemented in step (i) of the process according to the invention comprise, independently of each other, in addition at least one C8-C40 fatty acid, at least C8-C40 fatty alcohols, at least one triglyceride and / or at least one wax.More preferably according to this embodiment, the C8-C40 fatty acid(s) may be chosen from oleic acid, stearic acid, behenic acid, ricinoleic acid, linoleic acid, linolenic acid, and mixtures thereof; the C8-C40 fatty alcohol(s) may be chosen from lauric alcohol, myristyl alcohol, oleyl alcohol, cetyl alcohol, stearyl alcohol, and mixtures thereof; the triglyceride(s) may be chosen from vegetable oils such as olive oil, corn oil, avocado oil, almond oil, and mixtures thereof; the wax(s) may be chosen from beeswax, jojoba wax, and mixtures thereof.
[0142] Preferably, the fat content in the composition containing it is in the range of 10 to 99% by weight, more preferably 25 to 98% by weight, more preferably 40 to 95% by weight, better 50 to 95% by weight, relative to the total weight of the composition containing it.
[0143] Preferably, the content of liquid fat(s) in the composition containing it is in the range of 10 to 99% by weight, more preferably 25 to 98% by weight, more preferably 40 to 95% by weight, better 50 to 95% by weight, relative to the total weight of the composition containing it
[0144] Preferably, the content of C8-C40 fatty ester(s) in the composition containing them is in the range of 10 to 99% by weight, more preferably 25 to 98% by weight, more preferably 40 to 95% by weight, better 50 to 95% by weight, relative to the total weight of the composition(s) container. Water
[0145] According to a particular embodiment of the invention, the composition or compositions implemented in step (i) of the process according to the invention are, independently of each other, aqueous.
[0146] More particularly, the composition or compositions implemented in step (i) may have, independently of each other, a total water content of between 20 and 99% by weight, more preferably between 30 and 90% by weight, better between 35 and 80% by weight, and even better between 40 and 70% by weight, relative to the total weight of the composition containing it.
[0147] Advantageously, the composition or compositions implemented in step (i) of the process according to the invention may, independently of each other, further comprise at least one organic solvent.
[0148] For the purposes of the invention, it is understood that the organic solvents are liquid at 25°C and atmospheric pressure, different from fats as described above, and preferably miscible in water.
[0149] Preferably, the organic solvent(s) are chosen from C1-C6 monoalcohols, C2-C6 polyols, C2-C6 polyol ethers; more preferably chosen from ethanol, isopropanol, propylene glycol, butylene glycol, pentylene glycol, hexylene glycol, dipropylene glycol, diethylene glycol, glycerin, 2-butoxyethanol, propylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monomethyl ether, and mixtures thereof.
[0150] More preferably, the composition(s) implemented in step (i) of the process according to the invention further comprise, independently of each other, at least one C2-C6 polyol, more particularly selected from propylene glycol, butylene glycol, pentylene glycol, hexylene glycol, dipropylene glycol, diethylene glycol, glycerin, and mixtures thereof.
[0151] For the purposes of the present invention, C2-C6 polyols do not contain an ether function. Therefore, for the purposes of the present invention, C2-C6 polyols are different from C2-C6 polyol ethers.
[0152] Preferably, when one or more organic solvents are present in one of the compositions implemented in step (i) of the process according to the invention, the total content of organic solvent(s) is between 0.01 and 99% by weight, more preferably between 0.1 and 30% by weight, more preferably still between 0.5 and 25% by weight, and even better from 1 to 25% by weight, relative to the total weight of the composition comprising it / them.
[0153] Preferably, when one or more C2-C6 polyols are present in one of the compositions implemented in step (i) of the process according to the invention, the total content of C2-C6 polyol(s) is between 0.01 and 40% by weight, more preferably between 0.1 and 30% by weight, more preferably still between 0.5 and 25% by weight, and even better from 1 to 25% by weight, relative to the total weight of the composition comprising it / them.
[0154] According to a preferred embodiment of the invention, the composition or compositions implemented in step (i) of the process according to the invention are, independently of each other, anhydrous. For the purposes of this invention, "anhydrous composition" means a composition comprising a water content of less than 2% by weight; more preferably less than 1% by weight; more preferably still less than 0.5% by weight, or even less than 0.3% by weight, relative to the total weight of the composition. In particular, an anhydrous composition according to the invention is free of water. In other words, the composition does not contain water (0%). In particular, the composition does not include, preferably, any water added during its preparation, any residual water present may come from the raw materials used during preparation.
[0155] The composition or compositions implemented in step (i) of the process according to the invention may, independently of each other, further contain one or more additives commonly used in cosmetics, such as surfactants such as those selected from anionic, non-ionic, cationic and / or amphoteric surfactants, fixing polymers different from the polymers previously described, thickeners for example selected from anionic, non-ionic, cationic and / or amphoteric thickening polymers, reducing agents, oxidizing agents, anti-dandruff agents, anti-alopecia actives, preservatives, perfumes.
[0156] These additives may be present in the composition according to the invention in an amount ranging from 0 to 20% by weight relative to the total weight of the composition.
[0157] A person skilled in the art shall take care to choose any such additives and their quantities so that they do not impair the properties of the compositions of the present invention. Light irradiation
[0158] The process according to the invention includes a step (ii) of light irradiation of the keratin fibers consisting of exposing the keratin fibers to light radiation.
[0159] This step (ii) of light irradiation of the keratin fibers is carried out after the application step (i) as described previously.
[0160] For the purposes of the invention, light radiation can be natural or artificial.
[0161] For the purposes of the invention, "natural light radiation" means a luminous radiation of natural daylight (generated by the sun).
[0162] For the purposes of this invention, "artificial light radiation" means light radiation that differs from natural daylight (generated by the sun), i.e., light generated by a device. Artificial light radiation may be continuous or non-continuous.
[0163] Preferably, step (ii) of light irradiation of the keratin fibers consists of exposing the keratin fibers to artificial light radiation.
[0164] More preferably, step (ii) of light irradiation of the keratin fibers consists of exposing the keratin fibers to artificial light radiation having a wavelength between 250 and 750nm, more preferably between 280 and 700nm, better between 300 and 600nm, and even better between 350 and 500nm.
[0165] Preferably, step (ii) of light irradiation of the keratin fibers consists of exposing the keratin fibers to artificial light radiation whose irradiance is in the range of 0.1 to 50 W / cm2 of keratin fibers; more preferably from 0.5 to 30 W / cm2; more preferably still from 1 to 10 W / cm2.
[0166] Preferably, the artificial light radiation is generated by a device selected from arc lamps such as xenon and mercury lamps, fluorescent lamps, incandescent lamps such as halogens, light-emitting diodes (LEDs), organic light-emitting diodes (LEDo) and lasers.
[0167] By way of example, we can cite the goLITE BLU from Philips, the Energylight HF 3319 / 01 lamp from Philips, the Dayvia White and Messa lamps from Solvital, the Lumino Plus lamp from Lanaform, the medibeam lamp from Medibeam, the M-LED 01 lamp from Meimed, the Lifemax light pod lamp from Lifemax, the Lite-Pad lamp from Reicorp, the Omnilux Clear-U and New-U lamps from Omnilux, the 1000W Xenon Arc lamp from Lot-Oriel and the Camag Box 3 (4x8W) lamp from Camag.
[0168] Preferably, the duration of exposure of the keratin fibers to light radiation is greater than or equal to 1 second, more preferably between 1 second and 60 minutes, more preferably between 2 seconds and 55 minutes, even better between 5 seconds and 45 minutes.
[0169] More preferably, the duration of exposure of the keratin fibers to artificial light radiation is greater than or equal to 5 seconds, more preferably between 10 seconds and 60 minutes, more preferably still between 15 seconds and 55 minutes, even better between 20 seconds and 45 minutes.
[0170] Preferably, the process according to the invention comprises at least one rinsing step and / or drying of said keratin fibers. More preferably, the process according to the invention includes at least one step of rinsing and / or drying said keratin fibers, carried out after the step(s) (ii) of light irradiation.
[0171] As previously stated, in step (i) of the process according to the invention, the polymeric photoinitiator compound(s) and the crosslinkable non-colorant compound(s) may be included in the same composition (C) or in at least two separate compositions (A) and (B).
[0172] When the polymeric photoinitiator(s) and the crosslinkable non-colorant compound(s) are included in several separate compositions, the compositions including them may be applied simultaneously or sequentially; preferably simultaneously.
[0173] According to a particular embodiment of the invention, the process for treating keratin fibers comprises at least the following steps: (i) application to said keratin fibers, simultaneously or sequentially: - of a composition (A) comprising at least one polymeric photoinitiator compound, and - of a composition (B) comprising at least one crosslinkable non-colorant compound; then (ii) exposure of said keratin fibers to light radiation.
[0174] All the features, additional ingredients and preferences described above apply to this embodiment.
[0175] According to this embodiment of the invention, composition (A) is preferably applied to said keratin fibers before the application of composition (B).
[0176] According to this embodiment, the molar ratio of the quantity in moles of polymeric photoinitiator compound(s), to the quantity in moles of the crosslinkable function(s) of the crosslinkable non-colorant compound(s), is preferably in the range of 0.01 to 1000; more preferably from 0.05 to 500; more preferably still from 0.1 to 300; even better from 0.5 to 200.
[0177] Preferably, the polymeric photoinitiator compound(s) and the crosslinkable non-colorant compound(s) are included in a single composition (C). In other words, the process of treating keratin fibers includes at least the following steps: (i) application to said keratin fibers: - of a composition (C) comprising at least one polymeric photoinitiator compound and at least one crosslinkable non-colorant compound, as described above- previously; then (ii) exposure of said keratin fibers to light radiation.
[0178] All of the additional features and ingredients described above apply to this preference.
[0179] More preferably, composition (C) is anhydrous.
[0180] According to a preferred embodiment of the invention, the process for treating keratin fibers comprises at least the following steps: i. application to said keratin fibers: - of a composition (C) comprising: a. at least one polymeric photoinitiator compound, b. at least one crosslinkable non-colorant compound, c. at least one fatty substance; then i. exposure of said keratin fibers to light radiation.
[0181] All the features, additional ingredients and preferences described above apply to this embodiment.
[0182] More preferably according to this embodiment, composition (C) is anhydrous.
[0183] When the polymeric photoinitiator compound(s) and the crosslinkable non-colorant compound(s) are included in the same composition, the molar ratio of the amount in moles of polymeric photoinitiator compound(s) to the amount in moles of the crosslinkable function(s) of the crosslinkable non-colorant compound(s) is preferably in the range of 0.01 to 1000; more preferably from 0.05 to 500; more preferably still from 0.1 to 300; even better from 0.5 to 200.
[0184] The invention also relates to the composition (C) comprising: - at least one polymeric photo-initiator compound as described above, and - at least one crosslinkable non-color compound as described above.
[0185] All the characteristics, additional ingredients and preferences described above apply to composition (C).
[0186] Preferably, the composition (C) according to the invention further comprises at least one fatty substance as described above.
[0187] More preferably, the composition (C) according to the invention is anhydrous.
[0188] Preferably, the molar ratio of the amount in moles of polymeric photoinitiator compound(s), to the amount in moles of the crosslinkable function(s) of the crosslinkable non-color compound(s), is in the range of 0.01 to 1000; more preferably from 0.05 to 500; more preferably still from 0.1 to 300; even better from 0.5 to 200.
[0189] In particular, composition (C) is intended for the treatment of keratin fibers, more preferably for the care and / or shaping of keratin fibers, by particular human keratin fibers such as hair.
[0190] More preferably, composition (C) is intended for the care / repair of keratin fibers, and more particularly of hair.
[0191] Advantageously, composition (C) according to the invention is a non-coloring composition. In other words, the composition according to the invention does not allow the coloring of said keratin fibers. The composition according to the invention does not comprise a sufficient quantity of dye(s), such as direct dyes, oxidation dyes, and / or pigments, to color said keratin fibers.
[0192] The invention also relates to the use of at least one polymeric photoinitiator and at least one crosslinkable non-color compound for the treatment of keratin fibers, in particular human keratin fibers such as hair, preferably for the care and / or shaping of said keratin fibers, more preferably for the care / repair of said keratin fibers.
[0193] The following examples serve to illustrate the invention without, however, being intended to be limiting. Examples
[0194] In the following examples, all quantities are given as a percentage by weight of active material (AM) relative to the total weight of the composition.
[0195] Example: Composition A according to the invention (with a polymeric photoinitiator) and comparative composition B (without photoinitiator) were prepared from the ingredients whose contents are indicated in the table below:
[0196] [Tables 1] Ingredients Composition A (invention) Composition B (comparative) Polyquatemium-114 20.80 20.80 1.3 - di( {- [ 1 -chloro-9-oxo-9h-thioxanth en-4-yl)oxy ] acetylpoly [oxy ( 1 -methyl ethylene)]]oxy)-2,2-bis({a-[l-chloro-9-oxo-9h-thioxanthen-4-yl)oxy]acetyl poly[oxy(l -methy lethy lene) ]} oxy met hyl) propane (SpeedCure 7010 from Arkema) 1 Pentylene glycol 20 20 Water Qsp 100 Qsp 100
[0197] Strands of 2.7g of natural hair containing 90% white hair (SA20) have pre- were lightly washed with a standard shampoo (DOP®) then rinsed with water.
[0198] Next, each of compositions A and B was applied to 3 separate strands at a rate of 0.15g of composition per gram of hair, then the strands were left to rest for 5 minutes and finally dried. In other words, 3 strands were treated with composition A according to the invention and 3 other strands were treated with the comparative composition B.
[0199] The strands are then irradiated on each side of the strand by light radiation with a wavelength of 405nm and an irradiance of 2.5 W / cm2 of hair, at a speed of 1 cm of hair / second, for a total energy of 10 J / cm2. The irradiation was carried out using a FireEdge LED UV lamp from Phoseon Technology.
[0200] It has been observed that the strands treated according to the process of the invention have better hair coating, the hair seems thicker to the touch, and this in a lasting way, compared to the strands treated according to the comparative process.
[0201] A test called "RED 80" is then performed on the 6 previously treated strands:
[0202] The treated hair strands are soaked for 1 minute in the "RED 80" coloring composition obtained from a solution comprising: - 0.4668 g of RED 80 dye (Sirius Rot F3B - bayer), - 0.125 ml of pure acetic acid, and - qsp 100ml of water.
[0203] This solution is diluted 5 times to obtain said colour composition “RED 80” (0.093% by weight of colour).
[0204] Then the strands are rinsed with water to remove excess dye, and left to air dry.
[0205] Next, for each of compositions A and B, one of the treated strands undergoes no further treatment and another is washed 5 times according to the following washing cycle: - washing the strand with a standard shampoo (DOP®), then - rinse the wick with water, then - air drying of the wick.
[0206] The colour variation of the 6 previously treated strands is then evaluated using a Spectra Flash sf600x spectrophotometer from Datacolor.
[0207] The dye "RED 80" which has an affinity with the crosslinkable non-color compound b) (Polyquaternium-114) makes it possible to evaluate the amount of crosslinkable non-color compound b) remaining after several shampoos.
[0208] The greater the quantity of crosslinkable non-coloring compound(s) b) deposited on the hair, the higher the intensity of the red color.
[0209] The color of the highlights was evaluated in the L* a* b* system. In this L* system a* b*, the three parameters respectively denote the intensity (L*), a* indicates the green / red color axis and b* the blue / yellow color axis.
[0210] The variation in the colour of the strand after 5 wash cycles (AE5) is measured according to the following equation: â E n® + (â4' i (b* - b, y
[0211] In this equation, L*, a* and b* represent the values measured for the wick that has undergone 5 washing cycles, and Lo*, a0* and b0* represent the values measured for the wick that has not undergone a washing cycle.
[0212] The higher the value of AE, the greater the difference in color of the wick before and after washing, and in this case, the less the persistence of the deposit of crosslinkable non-color compound(s) b) is.
[0213] The results are reported in the table below:
[0214] [Tables2] ae5 Composition A (invention) 9.4 Composition B (comparative) 11.4
[0215] It is observed that the strands treated according to the process of the invention, comprising the application on the hair of at least one polymeric photoinitiator a), exhibits better wash retention, compared to the strands treated according to the comparative process, not comprising the application on the hair of at least one polymeric photoinitiator.
[0216] Example 2: Composition C according to the invention (with a polymeric photoinitiator) and comparative composition D (with a non-polymeric photoinitiator) were prepared from the ingredients whose contents are indicated in the table below:
[0217] [Tables3] Ingredients Composition C (invention) Composition D (comparative) Modified silicone acrylate with 5% functional acrylate group (X-22-2457 from Shin Etsu) 3 3 Organopolysiloxane with thiol groups and side chains (KF-2001 from Shin-Etsu) 2.25 2.25 Bis-cetearyl-amodimethicone 1.75 1.75 1,3-Di({-[1-chloro-9-oxo-9h-thioxanthen-4-yl)oxy]acetylpoly[oxy(1-methyl-1-ethylene)]]oxy)-2,2-bis({a-[l-chloro-9-oxo-9h-thioxanthen-4-yl)oxy]acetyl poly[oxy(l-methyl-ethylene)]} oxy methoxy) propane (SpeedCure 7010 from Arkema) 1 Ethyl trimethylbenzoyl-phenylphosphinate - 1 Isononyl isononanoate Qsp 100 Qsp 100
[0218] Strands of bleached hair of 2.7g (SA20) were previously washed with a standard shampoo (DOP®) and then rinsed with water.
[0219] Next, each of compositions C and D was applied to separate strands at a rate of 0.15g of composition / gram of hair, then the strands were left to rest for 5 minutes and finally dried.
[0220] The strands are then irradiated on each side of the strand by light radiation with a wavelength of 365nm and an irradiance of 1 W / cm2 of hair, for a total energy of 100 J / cm2. The irradiation can be carried out using a GC-113A LED UV lamp from Hamamatsu.
[0221] The treated strands irradiated in this way correspond to the so-called To strands.
[0222] After irradiation, the treated wicks are washed 7 times according to the washing cycle of example 1. The treated wicks thus irradiated and washed 7 times correspond to the so-called T7 wicks.
[0223] The deposits of compositions C and D on the hair were then evaluated in producing an infrared spectrum for each of the treated hair strands, at T0 (i.e. just after the irradiation step) and at T7 (i.e. just after the 7 washing cycles).
[0224] Infrared spectra were obtained using a Fourier transform infrared spectrometer from Mettler Toledo.
[0225] Each of the infrared spectra obtained was then analyzed.
[0226] In infrared spectra, the region around 800 cm⁻¹ corresponds to the region of one of the peaks of the modified silicone acrylate (i.e., the non-color crosslinkable compound b). Thus, the larger the peak in the region around 800 cm⁻¹, the greater the deposition of modified silicone acrylate on the hair.
[0227] The results are reported in the table below:
[0228] [Tables4] Composition A (invention): The peak at 800 cm⁻¹ is visible and of high intensity. The peak at 800 cm⁻¹ is visible and of low intensity. Composition B (comparative): The peak at 800 cm⁻¹ is visible and of high intensity. The peak at 800 cm⁻¹ is invisible.
[0229] It is thus observed that the strands treated according to the process of the invention, comprising the application on the hair of at least one polymeric photoinitiator a), exhibits better wash-resistance of the deposits, compared to the strands treated according to the comparative process, comprising the application on the hair of at least one non-polymeric photoinitiator.
Claims
Demands
1. A process for treating keratin fibers comprising at least the following steps: i. application to said keratin fibers, simultaneously or sequentially: a. of at least one polymeric photoinitiator compound, and b. of at least one crosslinkable non-colorant compound; then ii. the exposure of said keratin fibers to light radiation.
2.
3. A process according to the preceding claim, characterized in that the polymeric photo-initiator compound(s) comprise a main chain formed of units of formula -O-CnH2n+i-, with n an integer between 1 and 5, and one or more photoreactive groups selected from acetophenone groups, benzylketal groups, benzoin groups, phosphinic oxide type groups, benzophenone groups, thioxanthone groups, and mixtures thereof; more preferably from thioxanthone groups. A process according to the preceding claim, characterized in that the polymeric photoinitiator compound(s) are selected from 1,3-di({α-2-(phenylcarbonyl)benzoylpoly[oxy(l-methylethylene)]}oxy)-2,2-bis({α-2-(phenylcarbonyl)benzoylpoly[oxy(l-methylethylene)]}oxymethyl)propane, {α-2-(phenylcarbonyl)benzoylpoly(oxyethylene)-poly[oxy(l-methylethylene)]-poly(oxyethylene)} 2-(phenylcarbonyl)benzoate, 1,3-di( {- [ 1 -chloro-9-oxo-9h-thioxanthen-4-yl)oxy ] acetylpoly [oxy ( 1 -met hyl ethylene)]}oxy)-2,2-bis({a-[l-chloro-9-oxo-9h-thioxanthen-4-yl)oxy]ac etyl poly[oxy(l-methylethylene)]}oxymethyl) propane, le polybutylene glycol bis(4-benzoylphenoxy)acetate, le bis(benzophenone-2-carboxylic acid) polyethylene glycol ester, le polybutyleneglycol bis(9-oxo-9H-thioxanthenyloxy)acetate, le poly(ethyleneglycol) bis(p-dimethylamino benzoate), le polyethylene glycol di(P-4[4-(2-dimethylamino-2 -benzyl), le polymère 1,3-propanediol, 2-éthyl-2-(hydroxyméthyl)- avec oxirane,4-(diméthylamino)benzoate, et leurs mélanges.
4. A process according to any one of the preceding claims, characterized in that the content of polymeric photoinitiator(s) compound(s) a) in the composition containing it / them is in the range of 0.001 to 10% by weight, preferably 0.01 to 8% by weight, more preferably 0.1 to 5% by weight, and more preferably 0.2 to 2% by weight, relative to the total weight of the composition containing it / them.
5. A method according to any one of the preceding claims, characterized in that the crosslinkable non-color compound(s) b) are selected from polymeric crosslinkable non-color compounds, non-polymeric crosslinkable non-color compounds, and mixtures thereof; preferably from polymeric crosslinkable non-color compounds.
6. A method according to any one of the preceding claims, characterized in that the crosslinkable non-color compound(s) b) comprise at least one crosslinkable function selected from the (meth)acrylate, vinyl and / or thiol functions.
7. A process according to any one of claims 5 or 6, characterized in that the non-color crosslinkable polymeric compounds are selected from (mercaptopropyl)methylsiloxane / dimethylsiloxane copolymers, (mercaptopropyl)methylsiloxane homopolymers, organopolysiloxanes with side chains comprising at least one mercapto group, polysiloxanes with (meth)acrylic groups, (acryloxypropyl)methylsiloxane / dimethylsiloxane copolymers, polyquaternium-114, and mixtures thereof; preferably polyquaternium-114.
8. A process according to any one of the preceding claims, characterized in that the content of crosslinkable non-color compound(s) b) in the composition containing it / them is in the range of 0.01 to 40% by weight, preferably 0.1 to 30% by weight, more preferably 0.5 to 25% by weight, and more preferably 1 to 25% by weight, relative to the total weight of the composition containing it / them.
9. A method according to any one of the preceding claims, characterized in that the polymeric photoinitiator compound(s) a) and the crosslinkable non-colorant compound(s) b) are, in step (i), applied simultaneously to said keratin fibers, preferably by means of a composition (C) containing them.
10. A process according to any one of the preceding claims, characterized in that the composition or compositions implemented in step (i) further comprise, independently of each other, at least one fat; preferably selected from C6-C60 hydrocarbons, silicone oils, C8-C40 fatty alcohols, C8-C40 fatty esters, C8-C40 fatty ethers, and mixtures thereof.
11. A process according to any one of the preceding claims, characterized in that the composition or compositions carried out in step (i) further comprise, independently of each other, at least one organic solvent; preferably selected from C1-C6 monoalcohols, C2-C6 polyols, C2-C6 polyol ethers; more preferably selected from ethanol, isopropanol, propylene glycol, butylene glycol, pentylene glycol, hexylene glycol, dipropylene glycol, diethylene glycol, glycerin, 2-butoxyethanol, propylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monomethyl ether, and mixtures thereof.
12. A method according to any one of the preceding claims, characterized in that the light radiation is artificial light radiation; preferably having a wavelength between 250nm and 750nm, more preferably between 280nm and 700nm, more preferably still between 300nm and 600nm, and even better between 350nm and 500nm.
13. A method according to any one of the preceding claims, characterized in that the light radiation is artificial light radiation whose irradiance is in the range of 0.1 to 50 W / cm2 of keratin fibers; preferably from 0.5 to 30 W / cm2; and more preferably from 1 to 10 W / cm2.
14. A method according to any one of claims 12 or 13, characterized in that the artificial light radiation generated by a device selected from arc lamps such as xenon and mercury lamps, fluorescent lamps, incandescent lamps such as halogens, light-emitting diodes (LEDs), organic light-emitting diodes (OLEDs) and lasers.
15. Composition, preferably anhydrous, comprising: a. at least one polymeric photoinitiator compound as defined in any one of claims 1 to 3, and b. at least one crosslinkable non-colorant compound as defined in any one of claims 1, 5 to 7.