US3250682A - Method of setting hair with epoxy resin compositions - Google Patents

Method of setting hair with epoxy resin compositions Download PDF

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US3250682A
US3250682A US173482A US17348262A US3250682A US 3250682 A US3250682 A US 3250682A US 173482 A US173482 A US 173482A US 17348262 A US17348262 A US 17348262A US 3250682 A US3250682 A US 3250682A
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hair
solution
compound
water
diglycidyl ether
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Wilmsmann Hermann
Ludwig Wolfgang
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Procter and Gamble Deutschland GmbH
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Wella GmbH
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S424/00—Drug, bio-affecting and body treating compositions
    • Y10S424/02—Resin hair settings

Definitions

  • the present invention rela-tes to a method of maintaining hair in set condition, and more particularly to methods of and compositions for the treatment of hair so that the hair which is thus treated will remain in se-t condition over prolonged periods of time, and even under moist atmospheric conditions.
  • Both methods have the disadvantage that the hair deformation which is accomplished by the mentioned agents results in an undesirable alteration when there is a relative humidity in the air of more than about 5060%.
  • the deformed hair depending upon the type of treatment and the hair structure, is drawn together like a corkscrew or becomes strand-like and shapeless (i.e., the hair is either curled or straightened) hair treated with resins or synthetic emulsions or solutions will have only the last mentioned disadvantage.
  • the named hair deformation agents consequently only are useful and hold their stability at relatively low humidity.
  • the relative humidity may in general achieve values between 70 and 90%, ⁇ and particularly in the morning and evening hours, as well as in the kitchen and bathrooms the value may go up to 100%.
  • the filmforming agents it is necessary with the known filmforming agents to provide a layer which is actually several times thicker than the diameter of the hair iibers themselves. This is of course not possible because it would ice change the properties of the hair, particularly the combability and the feel of the hair.
  • hair prior to setting, is moistened with a solution or emulsion which has the property of protecting hair against atmospheric humidity so that when the set hair is dried it will remain in the desired set condition over a long period of time and even under conditions -of high humidity. Furthermore, in accordance with the present invention, the thus treated hair remains soft and natural to the touch.
  • the present invention mainly comprises the application to hair of at least lone compound having at least two epoxy groups per molecule and at least one substance which is adapted to react with and harden the compound, whereby the reaction product of the compound and the substance has the property of maintaining the hair in set condition over a relatively long period of time and even in moist atmospheric conditions.
  • the hair may be treated with a solution of the poly-epoxy compound and with a solution of the hardener, which, for example, may be a polyamine or a polycarboxylic acid, so as to wet the hair, the hair then being set in normal manner in wet condition,'for example by being wound around rollers or curlers or the like, whereupon the hair is then dried.
  • the resulting hair will remain in set condition even under conditions of extremely high relative humidity.
  • the film which is formed by the reaction of the starting compone-nts is a strongly three dimensional cross linked compound which is practically cause a portion of the epoxy groups react with reactable l amino gnoups or hydroxyl groups of the hair kenatin. Consequently, when human hair is treated in accordance with the method of the present invention, the obtained treated hair is remarkably resistant even to relative humidity of 90100%. In addition, certain properties of the hair, in contrast to the action of the previously mentioned deformation agents, are favorably changed by means of the present invention.
  • the so-called nitrogen number (note H. Freytag, Characterization of Sulfur-Containing Proteins, Folia Pharmaceutica (Istanbul), 3, 7:125-141 (1955)) which in the case of cosmetically untreated hair is markedly reduced, is considerably reduced in the case of hair which is permanently waved.
  • This nitrogen number is a measure of the number of free SH-groups in the keratin and thereby ofthe degree of cross linking.
  • the number of free SH-groups of the keratin is a measure of the degree of damage because, despite fixing, only a portion of the disulfide bridges which have been split by the reduction are reformed.
  • the number of SH- groups is, contrary to the other permanent waving methods, not increased, but is actually decreased. It may be considered that the reduction of the nitrogen number is partially due to the coating by means of the epox-ide resin lm.
  • the preferred polyepoxy starting compounds of the present invention are preferably those compounds having at least two epoxy groups per molecule which are soluble in Water or in mixtures of Water and Water-miscible solvents or in water-miscible solvents, such as:
  • Butadiene di-epoxide Triglycidyl-ether of the reaction product of glycerine and four moles ethylene oxide.
  • the hardeners which are used i.e., the substances which react with and harden the polyepoxy compound, such as polyamines and polycarboxylic acids, are preferably also those which are soluble in water, or in mixtures of Water and water-miscible solvents, or in the Water-miscible solvents themselves.
  • Suitable soluble primary or secondary diamines or polyamines are: ethylene diamine, diethylenetriamine, dipropylenetriamine, the above being unsubstituted polyamines, and also suitable are suhstituted aliphatic or aromatic diamino compounds which contain mainly carboxyl or hydroxyl groups, such as 3,4-
  • diaminobenzoic acid lysine, ornithine, arginine, cystine, N,N'-bis-oxyethyl-ethylenediamine, and the like.
  • particularly suitable hardeners are those hydroxylgroup-containing diamines which are obtained by the reaction of a compound containing at least two epoxy groups, suchas those mentioned above, with ammonia. The compound resulting from such reaction is a particularly suitable hardener for the purposesof the present invention.
  • bifunctional compounds such as polycarboxylic acid, e.g., maleic acid', which is preferably used in the form of its anhydride, adipic acid and the like, as well as other bifunctional compounds such as compounds which contain both an amino group and a mercapto group, e.g., cysteamine (HS-CH2-CH2NH2) or cysteine.
  • the hair is treated with a solution, which is preferably formed shortly before use, containing both at least one -compound having at least two epoxy groups per molecule and at least one hardener therefor.
  • the ratio of the epoxy compound to the hardener may be varied within extremely wide limits, but is most preferably chosen so that for each epoxy group there is present about one reactable hydrogen atom of the hardener.
  • the thus formed solution can be applied to the hair in usual manner. For example a relatively dilute solution of the so-called setting lotion or finger wave lotion can be applied and without removal of the excess can be permitted to react under the drier.
  • rst permit a concentrated solution to work in for several minutes, the excess to then be removed by rubbing or rinsing, and then setting the hair and permitting it to dry under the dryer. Itis also possible to operate according to a two stage method wherein the epoxy ycomponent is first permitted to work in for several minutes, the excess removed and then the hardener applied to the hair which is then set and dried. Likewise, it is of course possible to work in the reverse manner, i.e., to iirst apply the hardener, then to apply the epoxy, then to set the hair and dry it.
  • an accelerator and/ or other agents which can vary the properties of the obtained resin so as to improve the same.
  • Particularly suitable for this purpose may be mentioned resorcinol, catalytic amounts of heavy metal salts, particularly copper salts, thiosemicarbazides, and cationic active wetting agents such as cetyl pyridinium chloride.
  • EXAMPLE 1 Solution A 17.4 g. of ethylene glycol diglycidyl ether are dissolved in water and the amount of the solution adjusted to a total of 100 cc.
  • the ethylene glycol diglycidyl ether can be produced, for example, in accordance with the following method:
  • Solution B 13.1g. of dipropylenetriamine are dissolved in water and the solution brought ⁇ to a volume of cc.
  • Solution B 13.1 g. of dipropylenetriamine are dissolved in water, the solution diluted to 100 cc. and 3 g. of resorcinol are added thereto.
  • Example 1 To the solution B o-f either Example 1 or Example 2 is added 0.5 g. of cetylpyridinium chloride. The use of this solution is facilitated because of the increased wetting power thereof, and the hardening is surprisingly consider-ably accelerated.
  • Solution B 10.3 g. of diethylenetriamine are dissolvedrin Water and the solution diluted to a Volume of 100 cc. The further treatment proceeds as described in Example 1.
  • a solution B is prepared in accordance with Example 2, solution A is mixed with solution B and the further treatment is as described in Example 1.
  • Solution B 17.4 g. of ethylene glycol diglycidyl ether are mixed with 75 cc. of 25% aqueous ammonia solution and with water the volume is brought to a total of 100 cc. After a short time the solution becomes considerably warmed, and then the reaction mixture is maintained at a temperature of about 45-55 C. for 1 hour. The excess ammonia is then distilled off by steam and the remaining solution, after cooling with water, is diluted to a volume of 100 cc.
  • Solution A is mixed with 30 cc. of solution B and then the further procedure is as described in Example 1.
  • the setting obtained with this composition is still more stable against humidity than in the case of the setting obtained according to Example 1.
  • EXAMPLE 7 The same conditions as in Example 6 are used for making the hair treating composition, except that the final composition is prepared from 20 cc. of solution A, 20 cc. of solution B and 2O cc. of Water.
  • EXAMPLE 8 20 cc. of solution B of Example 2 are -iirst applied to the hair, and after about minutes the hair is wiped fairly dry. The hair is then treated in the same manner with 20 cc. of solution A of Example 2 and the hair thus treated is Vthen dried for 30 minutes under a drier at a temperature of about 40-50" C. After combing out the set-ting which is obtained is quite analogous with respect to its resistance against moisture to that obtained according to Example 2.
  • EXAMPLE 9 Solution A 13.9 g. of l-epoxyethyl3,4-epoxycyclohexane are dissolved in 50 cc. of isopropyl alcohol and the solution is diluted to a volume of 100 cc. with water. l
  • a solution B is prepared as in Example 1 and the lfurther working up proceeds as in Example 1.
  • EXAMPLE 10 Solution A 20.4 g. of glycerine diglycidyl ether are dissolved in Water and the volume of the solution brought to 100 cc.
  • a solution B is prepared as in Example 2 and the further treatment proceeds as in Example 1.
  • Solution B is prepared as in Example 2, and further procedure is as described in Example 1.
  • Solution B 13.1 g. of dlpropylenetriamine are dissolved in Water, l() cc. of concentrated ammonia are added thereto and also added is 0.001 g. of C-uSO-5H2O and then the solution is diluted to a-volume of 100 cc. with Water. The further procedure is as described in Example l.
  • Solution B 13.1 g. of dipropylenetriamine are dissolved in water, the solution is brought t-o a volume of 100 cc, and 3 g. of thiosemicarbazide are added thereto.
  • the further procedure is as described in Example 1.
  • Solution B 15.2. g. of 3,4-diam-inobenzoic acid are dissolved in S0 cc. of isopropyl alcohol, 10 cc. of concentrated ammonia are added thereto and the solution is diluted to 100 cc. with Water. The further procedure is as described in Example 1.
  • Solution B 24 g. of cystine and 8 g. of sodium'hydroxide are diluted in water and the volume brought to 10() cc.
  • the solutions A and B are mixed in a ratio of 1:1.
  • Solution B 9.8 g. of maleic acid anhydride are dissolved in Water and the solution brought to a volume of 100 cc.
  • EXAMPLE 18 A solution A is prepared according to Example l.
  • Solution B 7.8 g. of ethylenediamine-monohydrate are dissolved in Water and the solution brought to a volume of 100 cc. with water.
  • the solutions A and B are mixed in proportions of 1:1.
  • Solution B 14.6 g. of adipic acid are dissolved in 60 cc. of isopropyl alcohol and the volume of the solution is brought to 100 cc. with water.
  • the solutions A and B are mixed in proportions of 1:1.
  • the further procedure is as described in Example l.
  • Solution B is prepared as in Example 1.
  • EXAMPLE 21 X grams of one of the following epoxides and Y grams of dipropylenetriamine are dissolved in Water up to a total of 100 c-c. and applied to the hair according to Example 1:
  • Dipropylene- Epoxide X g.: triamine Y, g. 21.1 Di-glycol-di-glycidyl ether, or 7.15 19.6 Tri-glycol-di-glycidyl-ether, or 20.8 Tetra-glycol-di-glycidyl-ether, or
  • the hair After combing out, the hair has obtained a stable setting which is practically completely insensitive to high humidity.
  • hair subjected to permanent waving in the usual manner with ammoniacal thioglycolate solution and subsequently xed resulted in the hair having a nitrogen number of 18.7.
  • This hair when treated with the composition of Example 2 resulted in the nitrogen number thereof being reduced to 12.9.
  • the curls I, II, III and IV designate hair treated with the composition indicated below, in all cases the hair being wetted with the composition, wound on curlers, and dried under' a drier at a temperature of about 50 C. for 30 minutes.
  • Curves I and II indicate the stability against moisture of hair curled in accordance with the present invention, while curves III and IV in-dic-ate the stability for hair curled -in accordance with the prior art.
  • the points given in the graphs which are used for the curves are average values, each taken for 5 separate measurements. From the curves it is apparent that all known coating agents lack resistance in similar manner, that a considerable improvement is obtained by treatment of the hair with permanent waving compositions based on the use of mercaptans, while in all cases hair treated in accordance with the present linvention is considerably more resistant to the action of humidity.
  • Method of maintaining hair in set condition which comprises wetting hair with a solution containing at least one compound compatible with hair and having lbetween two and four terminal epoxy groups per molecule wherein the epoxy group is of the structure and at least one substance adapted to react with and harden said compound, dissolved in a solvent therefor selected from the group consistingof water, water miscible solvents and mixtures thereof; setting the thus wetted hair; and drying the thus set hair, thereby causing reaction between said compound and said substance,- whereby the hair will remain in set condition over a relatively long period of time and even under moist atmospheric conditions.
  • Method of maintaining hair in set condition which comprises wetting hair with la solution of at least one compound compatible with hair and having between two and four terminal epoxy groups per molecule wherein the epoxy group is of the structure and at least one substance selected from the group consisting of primary and secondary diamines and triamines adapted to react with and harden said compound, dissolved in a solvent therefor selected from the group consisting of water, water miscible solvents and mixtures thereof; setting the thus wetted hair; and drying the thus set hair, thereby causing reaction between said compound and said substance, whereby the hair will remain in set condition over a relatively long period of time and even under moist atmospheric conditions.
  • Method of maintaining hair in set condition whichcomprises wetting hair with an aqueous solution containing at least one compound compatible with hair and having between two and four terminal epoxy groups per molecule wherein the epoxy group is of the structure I C*C ⁇ O/ and at least one substance adapted lt-o react with and harden said compound; setting the thus wetted hair; and drying the thus set hair, thereby causing reaction between said compound and said subst-ance, whereby the l l hair will remain in set condition over a relatively long period of time and even under moist atmospheric conditions,
  • Method of maintaining hair in set condition which comprises wetting hair with a solution of at least one compound being selected from the group consisting of ethylene glycol diglycidyl ether, 1,3-butanedio1 diglycidyl ether, 1,4-butanediol diglycidyl ether, glycerine diglycidyl ether, 1-epoxyethyl-3,4-epoxycyclohexane, 3,4-epoxy-6- methyl cyclohexylmethyl 3,4epoxy6'methylcyclohexane carboxylate, dicyclopentadienediepoxide, butadienediepoxide, diglycidyl ether, polyglycohdiglycidylether, triglycidyl-ether of the reaction product of glycerine and four moles ethylene oxide, tetraglycidylether of the reaction product of pentaerythritol and four moles ethylene oxide, and triglycid
  • Method of maintaining hair in set condition which comprises wetting hair with a solution of at least one compound being selected Vfrom the group consisting of ethylene glycol diglycidyl ether, l,3-butanediol diglycidyl ether, 1,4-butanediol diglycidyl ether, glycerine diglycidyl ether, 1-epoxyethyl3,l-epoxycyclohexane, 3,4-epoxy-6 methyl cyclohexylmethyl 3,4epoxy-6'methylcyclo hex-ane carboxylate, -dicyclopentadienediepoxide, butadienediepoxide, diglycidyl ether, polyglycol-diglycidylether, triglycidyl-ether of the reaction product of glycerine and four moles ethylene oxide, tetraglycidyl-ether of the reaction product of pentaerythritol and tour moles ethylene oxide
  • Method of maintaining hair in set condition which comprises wetting hair with a solution of at least one compound compatible with hair and having between two and four terminal epoxy groups per molecule wherein the epoxy group is of the structure and at least lone reaction product of said compound with ammonia, said reaction product being adapted to react with and harden said compound, dissolved in a solvent therefor selected from the group consisting of water, water misci-ble solvents and mixtures thereof; setting the thus wetted hair; and drying the thus set hair, thereby causing reaction between said compound and said sub-- stance, whereby the hair will remain in set condition over a relatively long period of time and even under moist atmospheric conditions ⁇ '7.
  • Method of maintaining hair in set condition which comprises wetting hair with a solution of at least one compound compatible with hair and having between two and four terminal epoxy groups per molecule wherein the epoxy group is of the structure and at least one substance selected from the group consisting of cysteamine and cysteine and being adapted to react with and harden said compound, dissolved in a solvent therefor selected from the group consisting of water, water miscible solvents and mixtures thereof; setting the thus wetted hair; and drying the thus set hair, thereby causing reaction between said compound and Said substance, whereby the hair will remain in set condition over a relatively long period of time and even under moist atmospheric conditions.
  • Method of maintaining hair in set condition which comprises wetting hair with a solution of at least one compound having between two and four epoxy groups per molecule and ⁇ being selected from the group consisting of ethylene glycol diglycidyl ether, 1,3-butanediol diglycidyl ether, 1,4-butanediol diglycidyl ether, glycerine diglycidyl ether, l-epoxyethyl-3,ll-epoxycyclohexane, 3,4- epoxy -methylcyclohexylmethyl-3,4'epoxy6methyl cyclohexane carboxylate, dicyclopentadienediepoxide, butadienediepoxide, diglycidyl ether, polyglycol-diglycidylether, -triglycidyl-ether of the reaction product of glycer'me and four moles ethylene oxide, tetraglycidylether of the reaction product of pentaerythrito
  • cystine N,N'-bis-oxyethyl-ethylene-diarnine, N-aminoethyl-N-hydroxyethyl-amine, N hydroxyethyl 1,3 propanediamine, N 2 hydroxypropyl-ethylenediamine, N,Ndi2hydroxypropy1ethylenediamine, N,N di-hydroxyethyl-ethylenediamine, cystehmine, cysteine,- maleic acid, adipic acid and the reaction product of said compound with ammonia, yand also containing in solution thiosemicarbazide as a material adapted to accelerate the reaction lbetween said compound and said substance, dissolved in a solvent therefor selected from the group consisting of water, water miscible solvents and mixtures thereof; setting the thus wetted hair; and drying the thus set hair, thereby causing reaction between said compound and said substance, whereby the hair will remain in set condition over a relatively long period of time and even under moist atmospheric conditions.
  • Method of maintaining hair in set condition which comprises wetting hair with a solution of at least one compound compatible with hair and having between two and four terminal epoxy groups per molecule wherein the epoxy group is of the structure and at least one substance adapted to react with and harden said compound and also containing resorcinol, dissolved in a solvent therefor selected from the group consisting of water, water miscible solvents and mixtures thereof; setting the thus wetted hair; and drying the thus set hair, thereby causing reaction between said compound and said substance, whereby the hair will remain in set condition over a relatively long period of time and even under moist atmospheric conditions.
  • Method of maintaining hair in set condition which comprises wetting hair with a solution of at least one compound having between 2 and 4 epoxy groups per molecule and being selected from the group consisting of ethylene glycol, diglycidyl ether, 1,3-butanediol diglycidyl ether, 1,4-butanediol diglycidyl ether, glycerine diglycidyl lepoxyethyl,ll-epoxycyciohexane, r:lA-epoxy- 6 methyl-cyclohexylmethyl-3,4-epoxy-6'-methyl-cyclohexane carboxylate, dicyclopentadienediepoxide, butadienediepoxide, diglycidyl ether, polyglycol-diglycidylether, t-riglycidyl-ether of the reaction product of glycerine and four moles ethylene oxide, tetraglycidyl-ether of the reaction product of pentaery
  • Method of maintaining hair in set condition which comprises wetting hair with a solution of at least one compound having between 2 and 4 epoxy groups per molecule and being selected from the group consisting of ethylene glycol, diglycidyl ether, 1,3-'butanediol diglycidyl ether, 1,4-butane-diol diglycidyl ether, glycerine diglycidyl ether, l-epoxyethyl-3,4-epoxycyclohexane, 3,4- epoxy 6-methyl-cyclohexylmethyl-3,4'epoxy6methylcyclohexane carboxylate, dicyclopentadienediepoxide, butadienediepoxide, diglycidyl ether, polyglycol-diglycidyl ether, triglycidyl-ether of the reaction product of glycerine and four moles ethylene oxide, tetraglycidylether of the reaction product of pentaerythritol
  • Method of maintaining hair in set condition which comprises wetting hair with a solution of at least one compound having between 2 and 4 epoxy groups per molecule and being selected from ⁇ the group consisting of ethylene glycol, diglycidyl ether, 1,3-butanediol diglycidyl ether, 1,4Jbutanediol diglycidyl ether, glycerine diglycidyl ether, 1-epoxyethyl-3,4-epoxycyclohexane, 3,4- epoxy -methyl-cyclohexylmethyl-3,4epoxy6methylcyclohexane carboxylate, dicyclopentadienediepoxide, butadienediepoxide, diglycidyl ether, polyglylcol-diglycidyl-ether, triglycidyl-ether of the reaction product of glycerine and four moles ethylene oxide and triglycidyl cyanurate, and at least one substance adapted to react with and hard

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US3917817A (en) * 1971-11-29 1975-11-04 Oreal Hair treating cosmetic compositions containing piperazine based cationic polymer
US4013787A (en) * 1971-11-29 1977-03-22 Societe Anonyme Dite: L'oreal Piperazine based polymer and hair treating composition containing the same
US4635654A (en) * 1985-11-04 1987-01-13 Redken Laboratories, Inc. Method for evaluating efficacy of a hair styling product
US20030119089A1 (en) * 2001-09-25 2003-06-26 Dyke Mark Van Methods for controlling peptide solubility, chemically modified peptides, and stable solvent systems for producing same
WO2003087156A2 (en) * 2002-04-10 2003-10-23 Keraplast Technologies, Ltd. Heterogeneous crosslinked protein networks and methods for producing them
US20030204037A1 (en) * 2002-04-10 2003-10-30 Van Dyke Mark E. Methods for producing, films comprising, and methods for using heterogeneous crosslinked protein networks
US20030219486A1 (en) * 2002-04-10 2003-11-27 Van Dyke Mark E. Methods for producing, films comprising, and methods for using heterogenous crosslinked protein networks
US20030224052A1 (en) * 2002-04-22 2003-12-04 Van Dyke Mark E. Hydrogel with controllable merchanical, chemical, and biological properties and method for making same
US20040062793A1 (en) * 2002-07-05 2004-04-01 Dyke Mark Van Tissue defect dressings comprising proteinaceous networks
US20040120910A1 (en) * 2002-04-10 2004-06-24 Dyke Mark Van Methods for producing, films comprising, and methods for using heterogeneous crosslinked protein networks
US20050058686A1 (en) * 2002-07-25 2005-03-17 Mark Van Dyke Bioactive coating for medical devices
EP3040451A3 (en) * 2014-12-30 2016-10-12 Rohm and Haas Electronic Materials LLC Reaction products of amino acids and epoxies
WO2021224786A1 (en) * 2020-05-04 2021-11-11 Landa Labs (2012) Ltd. Compositions, kits and methods for styling hair fibers

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US10711360B2 (en) * 2017-07-14 2020-07-14 Rohm And Haas Electronic Materials Llc Nickel electroplating compositions with copolymers of arginine and bisepoxides and methods of electroplating nickel
EP4000599A1 (en) * 2020-11-17 2022-05-25 Beiersdorf AG Novel skin moisturizer
EP4000693A1 (en) * 2020-11-17 2022-05-25 Beiersdorf AG Two component moisturizer
EP4000692A1 (en) * 2020-11-17 2022-05-25 Beiersdorf AG Two component sunscreen

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US2510885A (en) * 1946-03-08 1950-06-06 Devoe & Raynolds Co Amine-epoxy-phenol compositions
US3052650A (en) * 1953-03-27 1962-09-04 Minnesota Mining & Mfg Heat-curing epoxy resin compositions

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US3917817A (en) * 1971-11-29 1975-11-04 Oreal Hair treating cosmetic compositions containing piperazine based cationic polymer
US4013787A (en) * 1971-11-29 1977-03-22 Societe Anonyme Dite: L'oreal Piperazine based polymer and hair treating composition containing the same
US4635654A (en) * 1985-11-04 1987-01-13 Redken Laboratories, Inc. Method for evaluating efficacy of a hair styling product
AU590808B2 (en) * 1985-11-04 1989-11-16 Redken Laboratories, Inc. Method for evaluating efficacy of a hair styling product
EP0269771B1 (en) * 1985-11-04 1992-02-26 Redken Laboratories Inc. Method for evaluating efficacy of a hair styling product
US20030119089A1 (en) * 2001-09-25 2003-06-26 Dyke Mark Van Methods for controlling peptide solubility, chemically modified peptides, and stable solvent systems for producing same
US7001988B2 (en) 2001-09-25 2006-02-21 Keraplast Technologies, Ltd. Methods for controlling peptide solubility, chemically modified peptides, and stable solvent systems for producing same
US6989437B2 (en) 2002-04-10 2006-01-24 Keraplast Technologies, Ltd. Methods for producing, films comprising, and methods for using heterogeneous crosslinked protein networks
US6914126B2 (en) 2002-04-10 2005-07-05 Keraplast Technologies, Ltd. Methods for producing, films comprising, and methods for using heterogenous crosslinked protein networks
WO2003087156A2 (en) * 2002-04-10 2003-10-23 Keraplast Technologies, Ltd. Heterogeneous crosslinked protein networks and methods for producing them
US20030204037A1 (en) * 2002-04-10 2003-10-30 Van Dyke Mark E. Methods for producing, films comprising, and methods for using heterogeneous crosslinked protein networks
US20040120910A1 (en) * 2002-04-10 2004-06-24 Dyke Mark Van Methods for producing, films comprising, and methods for using heterogeneous crosslinked protein networks
WO2003087156A3 (en) * 2002-04-10 2004-09-02 Keraplast Tech Ltd Heterogeneous crosslinked protein networks and methods for producing them
US20030219486A1 (en) * 2002-04-10 2003-11-27 Van Dyke Mark E. Methods for producing, films comprising, and methods for using heterogenous crosslinked protein networks
US7001987B2 (en) 2002-04-22 2006-02-21 Keraplast Technologies, Ltd. Hydrogel with controllable mechanical, chemical, and biological properties and method for making same
US20030224052A1 (en) * 2002-04-22 2003-12-04 Van Dyke Mark E. Hydrogel with controllable merchanical, chemical, and biological properties and method for making same
US20040062793A1 (en) * 2002-07-05 2004-04-01 Dyke Mark Van Tissue defect dressings comprising proteinaceous networks
US20050058686A1 (en) * 2002-07-25 2005-03-17 Mark Van Dyke Bioactive coating for medical devices
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EP3040451A3 (en) * 2014-12-30 2016-10-12 Rohm and Haas Electronic Materials LLC Reaction products of amino acids and epoxies
US9783905B2 (en) 2014-12-30 2017-10-10 Rohm and Haas Electronic Mateirals LLC Reaction products of amino acids and epoxies
US10041182B2 (en) 2014-12-30 2018-08-07 Rohm And Haas Electronic Materials Llc Reaction products of amino acids and epoxies
WO2021224786A1 (en) * 2020-05-04 2021-11-11 Landa Labs (2012) Ltd. Compositions, kits and methods for styling hair fibers

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