WO2019220367A2 - Composés aromatiques substitués par azide ou diazirine et procédés de modification de kératine et de polymères à l'aide de ceux-ci - Google Patents

Composés aromatiques substitués par azide ou diazirine et procédés de modification de kératine et de polymères à l'aide de ceux-ci Download PDF

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WO2019220367A2
WO2019220367A2 PCT/IB2019/054032 IB2019054032W WO2019220367A2 WO 2019220367 A2 WO2019220367 A2 WO 2019220367A2 IB 2019054032 W IB2019054032 W IB 2019054032W WO 2019220367 A2 WO2019220367 A2 WO 2019220367A2
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hair
coating
keratin
haloalkyl
formula
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WO2019220367A3 (fr
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Jonathan WOLFE
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B69/00—Dyes not provided for by a single group of this subclass
    • C09B69/008—Dyes containing a substituent, which contains a silicium atom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B11/00—Diaryl- or thriarylmethane dyes
    • C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
    • C09B11/06—Hydroxy derivatives of triarylmethanes in which at least one OH group is bound to an aryl nucleus and their ethers or esters
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/0003—Monoazo dyes prepared by diazotising and coupling from diazotized anilines
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B57/00—Other synthetic dyes of known constitution
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B57/00—Other synthetic dyes of known constitution
    • C09B57/001—Pyrene dyes

Definitions

  • the present application relates to novel azide- or diazirine-substituted aromatic compounds and methods of modifying keratin and polymers with them.
  • the present application relates to a method for covalent modification of proteins and keratin fibres with said azide- or diazirine-substituted aromatic compounds to alter their surface tension.
  • Keratin fibres are one of the toughest materials existing in nature. They are the key structural material present in outer protective layer of skin, hairs, nails, horns, feathers, claws, hooves, scales etc. They have essentially evolved as a barrier to the surrounding environment protecting inner softer tissues from hostile environment and stress of life. However, being the outermost layer, they also serve an aesthetic purpose. In combination with innumerable pigments and varying texture, they impart incredibly beautiful designs and colour to different species in the forms of distinctive furs and feathers etc.
  • a particular example may be to coat the outer layer of hairs with strongly hydrophobic/omniphobic molecules (figure 1) to give it a non-sticky, smooth, water repellent and desirable texture.
  • Such a technique will potentially have strong commercial implications seeing the ever-growing market of hair care products etc. In fact, equally good commercial applications exist for other similar industries like leather industry etc.
  • seeing at molecular level, applying such permanent coating is challenging due to the structure and chemical composition of keratin fibre which is relatively inert due to abundance of non reactive amino acids like glycine, proline, disulphide bonded cysteine, leucine etc.
  • US 2014/0155522 A1 describes a superhydrophobic coating comprising particles with nanostructured surface topology being covalently bonded to a resin rendering at least one surface of the resin superhydrophobic.
  • US 2012/0107556 A1 describes a superhydrophobic film consisting of a first major surface and a second major surface opposite to the first where narrow nanocavities in the microstructure of its surface are present.
  • U.S. Pat. No. 7,419,615 B2 describes a method of forming a renewable superhydrophobic material comprising of mixing a hydrophobic material with roughness-inducing particles, curing the mixture, etching away the particles to form a superhydrophobic surface.
  • WO 2008/075282 A2 describes cosmetic kit comprising of hydrophobic solid particles, and 2 different compounds which are capable of reacting by hydrosilylation reaction in the presence of catalyst when brought into contact.
  • the hydrophobic materials were typically applied to keratin fibers by means of passive adsorption. This relatively weak interaction between the hydrophobic materials and keratin surface can be a major drawback as it translates to diminished robustness and longevity of the coating, particularly when compared to a covalently-attached hydrophobic film.
  • the present invention relates to a compound of formula (I):
  • Ri, R 2 , R 3 , R 4 and Rs are independently selected from hydrogen, halogen, linear or branched (Ci-C 36 )-alkyl, linear or branched (Ci-C 36 )-haloalkyl, or an organic dye molecule; and
  • X is selected from the following groups:
  • R 3 is a haloalkyl of formula * — (— c ⁇ -CF 3 , wherein n is between 0 and 36.
  • Ri, R 2 , R 4 and R 5 are hydrogens and R3 is a haloalkyl of formula ⁇ Cp3 wherein n is between 0 and 36.
  • Ri, R 2 , R and R 5 are hydrogens
  • R 3 is a haloalkyl of formula *— c— c -(-CHF 2 — ⁇ -CF 3 , wherein n is between 0 and 36.
  • R 3 is an organic dye molecule.
  • Said organic dye molecule can be selected from the following compounds:
  • Ri, R 2 , R 3 , R 4 and R 5 are independently selected from hydrogen, halogen, linear or branched (Ci-C 36 )-alkyl, linear or branched (Ci-C 36 )-haloalkyl, or an organic dye molecule; and
  • Y is absent or selected from the following groups:
  • Z is a polymer or keratin; said method comprises:
  • Z is keratin.
  • Z is a polymer.
  • said polymer is polydimethylsiloxane (PDMS).
  • said mixture in step (b) is either irradiated with UV light having a wavelength between 240 nm and 450 nm, heated above 90°C, or electrical current is applied to said mixture in step (b) with voltage above 2V.
  • the term “about” is understood as within a range of normal tolerance in the art, for example within two standard deviations of the mean. In one embodiment, the term “about” means within 10% of the reported numerical value of the number with which it is being used, preferably within 5% of the reported numerical value. For example, the term “about” can be immediately understood as within 10%, 9%, 8%, 7%, 6%, 5%, 4%, 3%, 2%, 1%, 0.5%, 0.1%, 0.05%, or 0.01% of the stated value. In other embodiments, the term “about” can mean a higher tolerance of variation depending on for instance the experimental technique used.
  • alkyl refers to a saturated monovalent hydrocarbon radical.
  • exemplary alkyl groups include methyl, ethyl and propyl.
  • (Ci-C36)-alkyl refers to an alkyl containing from one to three carbon atoms.
  • haloalkyl this is intended to refer to an alkyl having bonded thereto one, two or three of the other, specifically-named groups, such as halogen, at any point of attachment on either the straight or branched chain of the alkyl.
  • aryl refers to a monovalent unsaturated aromatic hydrocarbon radical of six to eighteen ring atoms having a single ring or multiple condensed rings.
  • exemplary aryl groups are phenyl, biphenyl, benzyl, naphthyl, anthryl, pyrenyl and the like.
  • substituted is used with such groups, as in “optionally substituted with one to three substituents independently selected from”, it should be understood that the aryl moiety may be optionally substituted with the same or different groups independently selected from those recited above and hereinafter as appropriate.
  • cycloalkyl refers to a fully saturated and partially unsaturated cyclic monovalent hydrocarbon radical having three to six carbon atoms in a ring.
  • exemplary cycloalkyl groups are cyclopropyl, cyclobutyl, cyclopentyl and cyclohexanyl.
  • heterocyclic and “heterocyclyl” refer to fully saturated or partially unsaturated non-aromatic cyclic radicals of three to eight ring atoms in each cycle (in each monocyclic group, six to twelve atoms in a bicyclic group, and ten to eighteen atoms in a tricyclic group), which have at least one heteroatom (nitrogen, oxygen or sulphur) and at least one carbon atom in a ring.
  • Each ring of the heterocyclic group containing a heteroatom may have from one to three heteroatoms, where the nitrogen and/or sulphur heteroatoms may optionally be oxidised and the nitrogen heteroatoms may optionally be quaternised.
  • a heterocyclyl group may have a carbon ring atom replaced with a carbonyl group.
  • the heterocyclyl group may be attached to the remainder of the molecule at any nitrogen atom or carbon atom of the ring or ring system.
  • the heterocyclo group may have a second or third ring attached thereto in a spiro or fused fashion, provided the point of attachment is to the heterocyclyl group.
  • An attached spiro ring may be a carbocyclic or heterocyclic ring and the second and/or third fused ring may be a cycloalkyl, aryl or heteroaryl ring.
  • Exemplary monocyclic heterocyclic groups include azetidinyl, oxiranyl, pyrrolidinyl, pyrazolinyl, imidazolidinyl, dioxanyl, dioxolanyl, oxazolidinyl, piperidinyl, piperazinyl, morpholinyl, tetrahyrdofuryl, tetrahydropyranyl, thiamorpholinyl, and the like.
  • bicyclic heterocyclic groups include indolinyl, isoindolinyl, quinuclidinyl, benzopyrrolidinyl, benzopyrazolinyl, benzoimidazolidinyl, benzopiperidinyl, tetrahydroisoquinolinyl, tetrahydroquinolinyl, dihydroisoindolyl and the like.
  • heteroaryl refers to aromatic monocyclic, bicyclic or tricyclic radicals of three to eight ring atoms in each cycle (for example, three to eight atoms in a monocyclic group, six to twelve atoms in a bicyclic group, and to to eigtheen atoms in a tricyclic group), which have at least one heteroatom (nitrogen, oxygen or sulphur) and at least one carbon atom in a ring.
  • Each ring of the heteroaryl group may have one to four heteroatoms, wherein nitrogen and/or sulphur may optionally be oxidised, and the nitrogen heteroatoms may optionally be quaternised.
  • the heteroaryl group may be attached to the remainder of the molecule at any nitrogen atom or carbon atom of the ring or ring system. Additionally, the heteroaryl group may have a second or third carbocyclic (cycloalkyl or aryl) or heterocyclic ring fused thereto provided the point of attachment is to the heteroaryl group.
  • heteroaryl groups are pyrrolyl, thienyl, thiazolyl, imidazolyl, furanyl, indolyl, isoindolyl, oxazolyl, isoxazolyl, benzothiazolyl, benzoxazolyl, quinolinyl, isoquinolinyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazolyl, tetrazolyl and so on.
  • Exemplary bicyclic heteroaryl groups include benzothiazolyl, benzoxazolyl, quinolinyl, benzoxadiazolyl, benzothienyl, chromenyl, indolyl, indazolyl, isoquinolinyl, benzimidazolyl, benzopyranyl, benzofuryl, benzofurazanyl, benzopyranyl, cinnolinyl, quinoxalinyl, pyrrolopyridyl, furopyridinyl (such as furo[2,3-c]pyridinyl, furo[3,2-b]pyridinyl] or furo[2,3-b] pyridinyl), triazinylazepinyl, and the like.
  • the heterocyclyl ring may optionally be fused to a (one) aryl or heteroaryl ring as defined herein provided the aryl and heteroaryl rings are monocyclic. Additionally, one or two ring carbon atoms in the heterocyclyl ring can optionally be replaced with a carbonyl group. When the heterocyclyl ring is partially saturated it can contain one to three ring double bonds provided that the ring is not aromatic.
  • alkoxy refers to the groups of the structure -OR and wherein the group R is independently selected from the alkyl or cycloalkyl groups defined and recited above and hereinafter as appropriate.
  • alkylamino or "dialkylamino” refers to an amino group wherein one or both of the hydrogen atoms are replaced with a group selected from the alkyl or cycloalkyl groups defined and recited above and hereinafter as appropriate.
  • halo and halogen refers to fluoro/fluorine, chloro/chlorine, bromo/bromine, or iod/iodine radicals/atoms, relatively.
  • haloalkyl refers to alkyl and cycloalkyl radicals as defined above, substituted with one or more halogen atoms, including those substituted with different halogens. Exemplary groups are chloromethyl, trifluoromethyl, perfluoropropyl, trichloroethylenyl, chloroacetylenyl, and the like.
  • Nitrenes and carbenes particularly are high energy, extremely reactive species known to give indiscriminate reaction with most organic surfaces.
  • C-H insertion reactions of nitrenes and carbenes (apart from their reactions with nucleophiles like OH and NH 2 and with double bonds) which make them a suitable candidate for modifying the keratin fibres with a dense layer of molecules.
  • carbene precursors diazirines
  • their equivalents form highly reactive intermediates which are able to covalently bind to a large variety of compounds ( Figure 100). Therefore, they are highly suitable for coating and labelling applications, especially in biological settings as their high reactivity enable more comprehensive and uniform coating of anisotropic surfaces, while having low risk of an activated molecule being able to survive long enough so to enter the body and cause physiological damage.
  • these species that are usually activated by UV light, can also be activated using heat, and/or voltage stimulus making them more suitable for application on hair.
  • Binder examples general structures:
  • nitrenes and carbenes can be readily generated from precursor molecules, for example, from the easily obtained azides and diazo compounds respectively by treating them with heat or UV light.
  • Other activation methods can also be employed to generate these reactive species from their precursors which include treatment with acids, bases or other catalysts including metals, or by applying voltage, etc.
  • these reactive species work as handles or point of attachment between the surface and the molecule of interest.
  • an alkyl or aryl azide may be used to install an alkyl or aryl group along with X on an organic surface by activation of the azide to generate nitrene (reactive species) followed by treatment of the surface with the reactive species.
  • activation of the precursor is done on the surface (in situ) as the reactive species generated from such activation have generally very short lives.
  • R/R1/R2 may be alkyl or aryl groups, perfluorocarbons, fluorinated hydrocarbons, silicone base chains like polyhexafluorodimethylsiloxane, polydimethylsiloxane, Perfluoropolyethers, and any other species that will render the surface with a desired trait such as superhydropibocity which requires installation of species having low surface tension.
  • X may be varied according to the desired type of modification, for example it may be H, F, CH 3 , CF 3 or other alkyl or aryl groups if a hydrophobic surface is desired.
  • R/R ⁇ F ⁇ may be:
  • the superhydrophobic layer attached will only partially bond to the activated surface as the availability of reactive sites is limited.
  • silane with a carbene, nitrene or other radical precursors that can be inserted into C-H bonds
  • the molecules form a tightly covalent bonded layer with the surface.
  • the reaction is fast and does not produce toxic elements during its process. Furthermore, there is no need to conduct complicated preparation steps to activate the surface prior to the reaction.
  • the precursor molecule may be an alkyl or aryl azide including acyl azide, carboalkoxy azide, sulfonyl azide or phosphoryl azide etc. along with isocyanates, sulfanone, oxaziridine, ylides, azaheterocycles, amines with or without good leaving groups, nitro or nitroso compounds etc.
  • the precursor molecule may be a diazo compound, diazirine, hydrazone, ketene, ylide, strained ring, strained alkene, heterocyclic ring and compounds with good leaving groups etc.
  • a typical example may be:
  • activation methods are also possible to generate active species from precursor molecules. Choice of a method or a combination of methods may depend on its effectiveness, practical applicability and cost etc. The most common methods that are used to generate above mentioned active species from precursor molecules include, irradiation with light, exposure to heat, application of voltage, use of acids, bases, a specific chemical or catalysts including metals etc.
  • R groups may be chosen depending on their physical and chemical properties. For example, a simple perfluorocarbon chain is preferred for a low-friction, superhydrophobic/omniphobic coating forming a monolayer. A branched chain may increase the density and surface coverage enhancing the properties further, as well as introducing additional superhydrophobic effects ( Figure 102), but with reduced tribological improvements and weaker mechanical stability.
  • the last, repeating the reaction process for serval time, is also very important for formation of a monolayer.
  • a uniform monolayer, without exposed regions having high surface tension, is crucial for achieving a consistent superhydrophobic surface.
  • cleaning and coating the surface for several time can help to ensure that it is fully covered.
  • Hydrocarbon chains may also give a superhydrophobic surface with a possibility of forming multilayer through intermolecular C-H insertion reactions among reactive species. It may give a roughly systematic or totally random multilayer (Figure 103)
  • hydrophilic surface utilising an R chain which is polar or is capable of forming hydrogen bonds with water molecules.
  • R chains having hydroxyl groups or polyethylene glycol (PEG) chains which will tend to attract water giving a moist surface.
  • An R group may also be chosen in a way so that it can undergo co-polymerisation reaction with another suitable molecule to give a higher extent of modification/ surface coverage.
  • Group W in A is capable of cross reacting with Z in B where Z can undergo self-polymerisation.
  • An example of this kind of molecules may be as shown in Figure 104 where thiol (W) can react with vinyl group (Z) in the presence of a radical initiator and vinyl group can undergo polymerization at the same time.
  • Silanes, and the like may also be used as R groups where, after initial attachment to the surface, they may undergo copolymerization reaction with other silane to increase surface coverage/density.
  • Such dye can be used as a long-lasting makeup, a hair coating, nail coating, pets, leathers, or to coat fabrics and textiles such as linens and garments.
  • a cleavable chain that is degraded over time by exposure to oxygen, water vapor, visible light, UV, or other active compounds. This can enable slow and tailored release or active components such are antibacterial agents, fragrance, etc.
  • the present invention relates to a compound of formula (I):
  • Ri, R 2 , R 3 , R 4 and Rs are independently selected from hydrogen, halogen, linear or branched (Ci-C 36 )-alkyl, linear or branched (Ci-C 36 )-haloalkyl, or an organic dye molecule; and
  • X is selected from the following groups:
  • Ri, R 2 , R 4 and Rs are hydrogens and
  • R 3 is a haloalkyl of formula * — (— C ⁇ -CF 3 , wherein n is between 0 and 36.
  • Ri, R 2 , R 4 and Rs are hydrogens and R 3 is a haloalkyl of formula ft ft- ⁇ ⁇ CHF2 ) n CF3 , wherein n is between 0 and 36.
  • Ri, R 2 , R 4 and R 5 are hydrogens and R 3 is a haloalkyl of formula *— c— C 2 -(-CHF 2 — ⁇ -CF 3 , wherein n is between 0 and 36.
  • R3 is an organic dye molecule.
  • Said organic dye molecule can be selected from the following compounds:
  • Ri, R 2 , R 3 , R 4 and R 5 are independently selected from hydrogen, halogen, linear or branched (Ci-C36)-alkyl, linear or branched (Ci-C36)-haloalkyl, or an organic dye molecule; and
  • Y is absent or selected from the following groups:
  • Z is a polymer or keratin
  • said method comprises:
  • Z is keratin.
  • Z is a polymer.
  • said polymer is polydimethylsiloxane (PDMS).
  • said mixture in step (b) is either irradiated with UV light having a wavelength between 240 nm and 450 nm, heated above 90°C, or electrical current is applied to said mixture in step (b) with voltage above 2V.
  • the present invention further relates to a new method of modifying surfaces, especially organic surfaces such as keratin fibres in hairs, furs, skin, nails etc. with the intention of altering their surface properties, specifically making them hydrophobic. Modification takes place by forming a covalent bond between the surface and extremely reactive chemical species nitrene, silylene, and carbene precursors which are generated in situ by activation of a precursor molecule. Extensive modification is expected since nitrenes and carbenes are known to react with various nucleophiles like OH and NH 2 etc. along with highly desirable C- H insertion reactions in saturated alkyl chains. In case of hairs, it is not only the keratin in cortex but also the cuticle which can react with these highly reactive species.
  • Desired surface properties can be achieved by designing suitable precursor molecule.
  • Superhydrophobic modification of hairs can be taken as an example here and as a product that can render hair smoother to the touch and easier to dry as well as have lower tendency to accumulate dirt, oils, dust and mud, which may be desirable for some people and for some pets.
  • the invention generates a self-cleaning surface on hair so that cleaning can be done less often.
  • the coating can be tailored to maintain the natural oil layer that is usually removed during shower or, alternatively, it can be used to reduce that layer by preventing its attachment and accumulation on the hair.
  • the coating can be tailored to make it easier to remove the oil layer and dirt layer deposited on hair quicker by shampooing, watering or even just be combing to dwindle the amount of oil-hair or by soaking the oil with a towel.
  • An Oleophobic/oleophilic comb or just a normal comb can be used to remove dirt, oil, dust, bacteria etc. From the hair. This can also be achieved by simply wetting the hair. As water does not stick to the hair but sticks to the dirt, it will efficiently clean the hair without the need of shampooing.
  • This coating can be purposely made to be shiny or contain a certain color to dye the hair as well as making it superhydrophobic.
  • the coating can be applied in tandem to a hair rebounding treatment, where the hairs disulfide bonds are reestablished to render a certain structure to the hair.
  • the incorporation of the coating proposed herein can improve this process be providing further protection.
  • a trifunctional linker that is inserted into the process can be used to install a group into the hair disulfide bonds as these are closed at the end of the treatment via that linker.
  • the coating can also be made to contain antibacterial agents that can be permanently attached or engineered to be release slowly overtime. This can also include fragrance and/or taste molecules to maintain good smell for hair, pets and fabrics.
  • the coating can also contain a UV blocking agent that is used to protect the coating and the hair from UV radiation (see figures 100 for dyes and uv blocker examples).
  • Coating with linkers that are UV degradable can be used to slowly release fragrance, antibacterial agents, etc. UV mediated release can alert the user that it is exposed to UV, prompting the user to move to a safer environment.
  • a hydrophilic, or Superhydrophilic coating (as seen in figure examples above) can be used to render hair that has wet effects for long periods of time, even forming something of a hydrogel effect on hair.
  • the coating can be used to render hair with different surface properties, it can be harnessed for the application of unique hair moisturizers and fragrance and taste elements that are dissolved in an oil, or other substances like silicone oils or perfluorocarbons or fluorinated liquids which have high affinity to the new hair surface, this affinity can be harnessed to extend the retention of the moisturizers, foams or gets that are applied. This can give a wet feeling to the air as well for a prolonged time with or without oily feel effects.
  • molecules that stimulate she skin such as peppermint can be added to give a freshness feeling to the hair as a result of the addition of the coating or the moisturizers.
  • Fluorinated solvents and the like can also be used to wash the hair without the use of water and soap.
  • additional coating methods can include a UV, light activated coating that is placed on the hair at home and gradually buildup during the day as the user is exposed to light or sun.
  • the coating can be activated by first coating the hair with a foam containing the coating and then spraying an initiator to begin the reaction.
  • a heating element such as ironing comb can be used to activate the coating as well as a plasma machine as in the Figure 107 that generates plasma between two plates 7A and 7B to activate the hair surface for reaction of silanes if these are needed.
  • MEMS micro electrical devices

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Hydrogenated Pyridines (AREA)
  • Cosmetics (AREA)

Abstract

L'invention concerne un procédé de modification covalente de fibres kératiniques pour modifier leur tension de surface, comprenant deux étapes simples : a) l'application du matériau sur les surfaces kératiniques; b) l'activation à l'aide de chaleur, de lumière ou d'électricité. Les structures moléculaires de l'invention sont utiles pour la modification de nombreuses autres surfaces de matériaux.
PCT/IB2019/054032 2018-05-16 2019-05-15 Composés aromatiques substitués par azide ou diazirine et procédés de modification de kératine et de polymères à l'aide de ceux-ci Ceased WO2019220367A2 (fr)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4569855A (en) * 1985-04-11 1986-02-11 Canon Kabushiki Kaisha Method of forming deposition film
AU2005227320B2 (en) * 2004-03-22 2010-06-24 Government Of The United States Of America, As Represented By The Secretary Of The Department Of Health And Human Services, National Insitutes Of Health Cellular and viral inactivation
CA2707942C (fr) * 2007-12-20 2016-01-05 Avon Products, Inc. Compositions cosmetiques pour conferer des films superhydrophobes
CN102065823B (zh) * 2008-05-16 2015-11-25 雅芳产品公司 用于提供超疏水性的组合物

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