Classifications

• • 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
• • 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
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
  • A61K8/463—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfuric acid derivatives, e.g. sodium lauryl sulfate
• • 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
  • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
  • A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
  • A61K8/8152—Homopolymers or copolymers of esters, e.g. (meth)acrylic acid esters; Compositions of derivatives of such polymers
• • D—TEXTILES; PAPER
  • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
  • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
  • D06M14/00—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials
  • D06M14/02—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials on to materials of natural origin
  • D06M14/06—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials on to materials of natural origin of animal origin, e.g. wool or silk
• • D—TEXTILES; PAPER
  • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
  • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
  • D06M14/00—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials
  • D06M14/18—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials using wave energy or particle radiation
  • D06M14/20—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials using wave energy or particle radiation on to materials of natural origin
  • D06M14/24—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials using wave energy or particle radiation on to materials of natural origin of animal origin, e.g. wool or silk
• • 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
  • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
  • Y10S8/18—Grafting textile fibers

Definitions

• ABSTRACT A process for the treatment of a keratinous substrate comprising the steps of l reduction of the substrate and (2) contacting same with a solution of vinyl monomer and free radical liberating catalyst, step (2) being effected in the presence of a water-soluble halide.
• the present invention relates in general to the treatment of keratinous substrates and in particular to the provision of a novel process for the modification of the properties of keratinous substances as typified by, for example, hair, wool, etc.
• keratinous materials may be modified in terms of their chemical and/or physical properties by suitable processing, e.g., the treatment of human hair for purposes of permanent waving or other conditioning, the relevant techniques being described in the published literature both patent and otherwise.
• suitable processing e.g., the treatment of human hair for purposes of permanent waving or other conditioning, the relevant techniques being described in the published literature both patent and otherwise.
• conventional processing usually involves an initial hair impregnation treatment with a suitable reducing solution whereby to deposit predetermined quantities of reducing agent on the individual hair fibers. Thereafter, chemical and/or physical modification of the hair is brought about by treating the same with a suitable oxidizing solution in a known manner.
• suitable reducing solution whereby to deposit predetermined quantities of reducing agent on the individual hair fibers.
• chemical and/or physical modification of the hair is brought about by treating the same with a suitable oxidizing solution in a known manner.
• the materials necessary to the implementation of such techniques are well known in the art and are available commercially in a wide variety of forms
• compositions necessary for use in such processing characteristically yield film deposits deficient in the requisite degree of adhesion, the final film deposit exhibiting a highly objectionable tendency to flake off, dry to a hard frangible depost and/or discolor the hair.
• occurrence of one or more of the foregoing shortcomings would suffice to vitiate any possibility of achieving the desired lustrous appearance.
• the ultimate requirements imposed upon a given hair conditioning treatment may vary considerably; thus, the involved treatment may be one primarily adapted to impart curl to the hair or conversely such treatment may be one designed to promote selective improvement in one or more such properties as tensile strength, elasticity, dye receptivity, body, thickness, etc. i
• a multi-step procedure for the treatment of keratinous materials to achieve predetermined modifications in one or more properties of such material is one which involves the sequential steps of (1) reduction, (2) rinsing and (3) oxidation.
• initial reduction of the keratin material is effected by treating same with a reducing solution for a time sufficient to permit substantial reduction of the keratin substrate, the term reduction here connoting the conversion of cystine linkages, i.e., disulfide bonds to mercaptan.
• the degree of reduction conversion can be controlled as desired by suitable choice of, for example, reducing agent, concentration, period of reducing solution-keratin contacting, etc.
• the keratin material is thereafter subjected to a thorough rinsing or equivalent operation for purposes of removing residual reducing agent.
• the utilization of an intermediate rinsing operation comprises a particularly critical phase of the over-all processing scheme since realization of the improvements contemplated depend critically thereupon.
• complete removal of reducing agent militates against any likelihood of monomer polymerization occurring in any appreciable degree within the interstices or free space surrounding the fiber elements, the polymerization step being effectuated following completion of the rinsing operation. It is, of course, imperative to the efiicacy of such processing that the involved chronology of operations be precisely complied with in order to assure the obtention of the manifold advantages made possible thereby.
• Yet another technique for effecting the modification of keratinous substrates is a method residing in the use of a specific catalyst material, namely, persulfuric acid and/or its water soluble salts.
• a specific catalyst material namely, persulfuric acid and/or its water soluble salts.
• the use of this specific catalyst material obviates any necessity for the use of multi-step processing to accomplish the desired keratin modification.
• the desired objectives can be achieved by the use of a single processing solution containing as essential ingredients the monomer material and persulfuric catalyst.
• processes of the aforedescribed type may be synergistically modified to advantage by conducting the polymerization phase, i.e., monomer or oxidizing solution treatment in the presence of a promoter selected from a highly delimited class of materials such promoter serving to augment or otherwise enhance the polymer grafiing rate.
• a promoter selected from a highly delimited class of materials such promoter serving to augment or otherwise enhance the polymer grafiing rate.
• the primary object of the present invention resides in the provision of an improved process for the treatment of keratinous substances, said process providing highly effective means to achieve particular and selected variations in one or more properties characterizing said keratinous substance.
• Another object of the present invention resides in the provision of an improved process for the treatment of keratinous substrates, said process being beneficially and advantageously adapted for implementation in connection with the setting, waving, or other conditioning of human hair to provide a hair product having excellent properties with respect to of form retention stability, thickness, body, lustre and the like.
• a further object of the present invention resides in the provision of a process for the treatment of keratinous substrates to enhance or otherwise augment the affinity of same for various types of dyestuffs.
• a still further object of the present invention resides in the provision of a process for the modification of keratinous materials and having exceptional utility as regards the treatment of fibrous materials constituted wholly or partly of wool to render the same more resistant to adverse environmental effects, e.g., moisture, heat, etc.
• Still another object of the present invention resides in the provision of a process for the modification of keratinous materials, said process being characterized by making possible the realization of substantial improvement in catalyst efficiency.
• said monomer being capable of undergoing free radical-induced polymerization
• said treatment being effected in the presence of a water-soluble halide salt, i.e., a salt of bromine, chlorine etc. with a water solubilizing cation such as alkali metal, e.g., lithium, sodium, potassium, etc.; ammonium; substituted ammonium, i.e., wherein one or more of the hydrogen atoms is replaced by alkyl, hydroxyalkyl and the like.
• a water-soluble halide salt i.e., a salt of bromine, chlorine etc.
• a water solubilizing cation such as alkali metal, e.g., lithium, sodium, potassium, etc.
• ammonium substituted ammonium, i.e., wherein one or more of the hydrogen atoms is replaced by alkyl, hydroxyalkyl and the like.
• the present invention is particularly and advantageously adapted for use in connection with a wide variety of keratin modification techniques, the sole requirement being that such technique involve as an essential manipulative step the employment of a monomer solution treatment in the presence of a free radical liberating catalyst for purposes of effecting modifications in the keratin substrate.
• the process described herein may be employed to significant advantage in conjunction with a process which is uniquely atypical, in that it necessarily involves the use of the keratin substrate per se as the reducing agent, which forms an effective redox couple in combination with the peroxide compound in the monomer treatment phase to yield polymerization-initiating free radical species.
• the initial reduction reaction is designed to bring about substantial reduction of the keratin substrate with the conversion of disulfide to mercapto.
• substantially complete removal of reducing agent per se e.g., bisulfite, thioglycolate or the like is virtually assured.
• reducing agent per se e.g., bisulfite, thioglycolate or the like.
• initiation of the polymer-forming reaction is confined practically exclusively to the keratinous mass, the latter serving as the locus of the free-radical liberating reaction.
• This particular mode of proceeding provides the significant advantage that any possibility of solution" polymerization is minimized, if not completely avoided, the quoted terminology connoting that condition which arises by virtue of polymer formation occurring within the free space area or interstices of the keratinous substrate.
• the process described herein may, also be utilized to pronounced advantage in keratin modification treatments wherein the reducing agent component is present as such during the monomer treating phase.
• the keratin material is present in non-reduced form, i.e., with disulfide linkages intact, during the monomer treatment phase and, as such, serves solely as a carrier for the reducing agent, i.e., the initial step according to processing of this type is solely for purposes of depositing reducing agent upon the individual fibers constituting the keratin mass.
• the mercapto groups thus provided, exhibit a pronounced capability of reducing peroxide catalyst materials with the attendant, in-situ generation of free radical species the latter providing effective means for initiating vinyl monomer polymerization.
• the predominant portion of vinyl monomer polymerization initiation as well as propagation is necessarily confined to the keratin particles per se when proceeding according to the preceding technique.
• the oxidizing solutions of the present invention comprise as essential ingredients (1) at least one vinyl type monomer, 2) a free radical liberating peroxide catalyst and (3) a water-soluble halide salt.
• Vinyl monomers suitable for use in the practice of the present invention encompass a relatively wide variety of materials and in general comprise any of those which are capable of undergoing free radical-induced polymerization.
• Monomer materials falling within the ambit of the foregoing definition may be defined as those compounds containing at least one grouping of the fonnula:
• R represents hydrogen, lower alkyl of one to four carbon atoms, e.g., methyl, ethyl, propyl, butyl, isobutyl, etc.
• R represents (a) carbalkoxy, i.e., COOR
• R represents hydrogen, alkyl containing from one to 20 carbon atoms, e.g., methyl, ethyl, n-pentyl, octyl, lauryl, stearyl and the like; alkenyl, containing from three to 10 carbon atoms, e.g., ally], 1,2-butenyl, 2,3-butenyl, 1,2-hexenyl, 2,3-hexenyl, etc.; hydroxyalkyl containing from two to 10 carbon atoms, e.g., 2-hydroxypropyl, 3-hydroxypropyl, Z-hydroxybutyl, 2,4,dihydroxybutyl, 4,6-dihydroxy hexyl, etc
• each of said alkyl preferably containing from one to four carbon atoms e.g., 2-N,N-diethylaminoethyl, 2-N- t-butylaminoethyl, 2-N,N-dimethylaminoethyl, 3-N,N- diisobutylaminopropyl; haloalkyl containing from one to 10 carbon atoms, e.g., hexafiuoro-isopropyl, perfluoroethyl, perfluoropropyl, 2-difluoro, 3-trifiuoropropyl, 2-chloroethyl, 2- chloropropyl, l,1 ,9-trihydroperfluorononyl methacrylate etc., vicinal epoxyalkyl containing from three to six carbon atoms, e.g., glycidyl, 3,4-epoxybutyl
• R and R represent hydrogen alkyl and preferably lower alkyl or alternatively may represent the atoms necessary to complete a polyunsaturated molecule such as:
• R represents an alkylene bridge containing preferably from one to four carbon atoms such as methylene
• halogen such as chlorine, bromine, etc.
• alkoxy e.g., methoxy, ethoxy, cyclohexoxy
• cyano i.e., the grouping C N
• alkenyl aryl e.g., o, m and p
• the aforementioned monomer materials may also be provided in the form of their salified derivatives, e.g., salts with water solubilizing cations.
• the monomer material prior to use may be converted to a suitable salified form such as typified by calcium acrylate, i.e., (Cl-l Cl-l-COO) Ca, sodium acrylate, potassium acrylate, calcium methylacrylate, and the like.
• a suitable salified form such as typified by calcium acrylate, i.e., (Cl-l Cl-l-COO) Ca, sodium acrylate, potassium acrylate, calcium methylacrylate, and the like.
• catalyst materials prescribed for use in accordance with the present invention likewise encompass a relatively wide variety of substances well known in the art for such purposes.
• catalyst compounds capable of liberating free radicals in the presence of reduced disulfide, i.e., mercaptan are eminently suitable for use herein.
• catalyst materials there may be mentioned without necessary limitation, inorganic and organic peroxides, hydroperoxides, peracids as well as their watersoluble salts with suitable representatives including, cumene hydroperoxide, tertiary-butyl peroxide, benzoyl peroxide, peracetic acid, perbenzoic acid, tertiary-butyl hydroperoxide, sodium peracetate, potassium peracetate, sodium perbenzoate, etc., potassium persulfate, sodium persulfate, persulfuric acid, and the like.
• concentration of catalyst material employed is not particularly critical beyond the obvious requirement that such material be present in catalytic quantities, i.e., small but efiective amounts sufficient to initiate polymerization.
• the concentration employed may vary over a relatively wide range.
• optimum realization of the improvements described herein can be assured by the employment of the catalyst material in concentrations ranging from about 0.001 to 1 to about 5:1 moles/mole of monomer with a range of 1:8 to 1:2 being particularly preferred.
• optimum catalyst concentration will depend upon a number of factors including, for example, monomer reactivity, the temperature employed during the treatment, the nature of the keratinous material, etc.
• departures from the ranges stated may be advisable in particular instances due to unusual or peculiar requirements.
• the third critical component of the oxidizing solutions contemplated for use herein comprises the water-soluble halide.
• the nature of the water solubilizing cation is not particularly critical, the salient requirement with respect thereto being that such cation be devoid of any tendency to deleteriously affect the keratin substrate or its immediate environs.
• water-soluble halide found to be eminently suitable for use herein there may be mentioned, for example, lithium bromide, lithium chloride, sodium bromide, sodium chloride, potassium bromide, potassium chloride, ammonium bromide, and ammonium chloride etc.
• the aforementioned bromides and chlorides are uniquely characterized in their exceptional capacity to augment to a considerable extent the graft copolymerization rate obtainable.
• the use of the halide salt in relatively minor amounts nevertheless permits the attainment of manifold increases in the polymerization reaction rate, thereby enabling the grafting of increased quantities of polymer for a given period of treatment.
• concentration of halide employed may likewise vary within relatively wide limits. In any event, it will usually be found that beyond certain concentration values incremental increases in the amount of halide employed fail to give rise to corresponding increases in graft polymerization rate, i.e., the quantum efficiency of the halide compound tends to diminish with the use of increased concentrations thereof.
• halide salt in concentrations ranging from about 0.025 to about 40 moles/mole of monomer with a range of 4 to 10 found to be particularly beneficial.
• the halide ion contributes effectively to the reaction mechanism giving rise to the formation and proliferation of free radicals.
• the halide salt e. g., lithium bromide
• the peroxide catalyst material e. g., potassium persulfate
• the respective monomer, catalyst and halide salt ingredients are preferably provided in the form of a homogenously dispersed medium employing one or more solvent materials of an inert nature.
• solvent materials of an inert nature.
• such ingredients may be formulated utilizing simple aqueous solutions or altematively solvent or mixed solvent systems, the nature and proportions of solvent employed depending, inter alia, upon the solubility characteristics of the monomer component.
• co-solvent mixtures consisting of from about 10 to about 90 percent by weight water, the remainder comprising one or more water miscible organic solvents, such as lower alkanol, e.g., ethanol, n-propanol, isopropanol, etc.; ketone, e.g., acetone; glycols, e.g., ethylene glycol, propylene glycol, etc.; ethers; ether glycols, e.g., ethylene glycol monomethyl ether, etc.
• water miscible organic solvents such as lower alkanol, e.g., ethanol, n-propanol, isopropanol, etc.
• ketone e.g., acetone
• glycols e.g., ethylene glycol, propylene glycol, etc.
• ethers ether glycols, e.g., ethylene glycol monomethyl ether, etc.
• the efficiency of the subject process depends to a great extent upon the temperature employed during the monomer solution treatment.
• the use of elevated temperatures is mandatory in order to obtain polymer grafting rate consonant with efficacious commercial practice.
• optimum results are obtainable with the use of temperatures falling within the range of from about 90 to about 200F. with a range of 100 to 140F. being especially preferred.
• departures from the aforestated ranges may be dictated in a particular circumstance depending to a great extent upon the nature of the keratin substrate being subjected to treatment.
• the treatment of wool as to be distinguished from, for example, on-scalp hair treatments correspondingly permits considerably more latitude as regards the selection of temperature.
• optimum temperature values for the problem at hand having reference to the volatility of the solution medium, decomposition points of the various reagants and reactants, etc. can be readily determined by those having reasonable skill in the art.
• the keratin sample selected for treatment comprises human hair, each sample weighing 1 i 0.003 gm.
• the hair sample is subjected to a reduction treatment for a period of 15 minutes utilizing an aqueous solution of ammonium thioglycolate (6 percent) having a pH of 9.
• the hair sample is rinsed thoroughly so as to remove residual reducing agent.
• the reduced hair sample is treated with a monomer solution of specified composition for a period of one hour at a temperature of 105F. Approximately 27 ml of monomer solution is employed per gram of hair treated. The amount of grafted polymer is calculated as the percent dry weight increase after drying for 12 hours over calcium chloride in a dry box. The results obtained are summarized in Table 1.
• the concentration of the internal solution will, of course, depend critically upon the population density of available mercapto; thus, greater amounts of mercapto lead to accelerated monomer and catalyst consumption rates, this condition tending to maintain a greater A C value.
• the monomer component(s) may be employed in a relatively wide range of concentrations subject, of course, to certain implicit limitations; thus, the concentration selected should be conducive to the obtention of efficient monomer-catalyst-keratin contacting and accordingly, the upper limiting value on concentration values should be selected having reference thereto.
• organic solvent materials having poor precipitant properties have somewhat of a retardant effect upon the polymer grafting rate. This is illustrated in the following examples wherein the procedure observed is that described in the foregoing examples.
• butyl methacrylate lauryl methacrylate allyl methacrylate 4,5-pentenyl methacrylate glycidyl methacrylate 3,4-epoxybutyl methacrylate Z-hydroxypropyl methacrylate ethylene glycol monomethacrylate methacrylic acid dimethylaminoethyl methacrylate N,N-diethyl methacrylamide methacrylamide N,N-methylene-bis-acrylamide N-tertiary-butyl methacrylamide calcium acrylate methyl acrylate butyl acrylate hexafluoroisopropyl acrylate perfluoroisobutyl acrylate calcium acrylate acrylonitrile divinyl benzene
• highly efficacious polymer and bromide components in the lower concentration ranges are attained with the use of sodium bromide,
• bromide salts appear to be somewhat more effective in that moderately higher polymerization rates are obtainable therewith.
• persulfate catalyst is replaced by equivalent amounts of, for example, cumene peroxide, cumene hydroperoxide, benzoyl peroxide, sodium perbenzoate, peracetic acid, tertiary-butyl hydroperoxide and tertiary-butyl peroxide.
• cumene peroxide cumene hydroperoxide
• benzoyl peroxide sodium perbenzoate
• peracetic acid tertiary-butyl hydroperoxide
• tertiary-butyl hydroperoxide tertiary-butyl peroxide
• the efiect of incorporating the indicated quantities of polymethyl methacrylate is the substantial reduction in the equilibrium moisture content of the treated hair samples.
• the tendency of hair to absorb significant quantities of water is an undesirable attribute since the retained moisture functions to dissipate or otherwise destroy the curl or wave retention capacity of the hair.
• the ability of fibrous keratinous materials to withstand the deleterious effects of humid environments may be significantly enhanced with the concomitant advantage that the effective life of a permanent wave set is correspondingly prolonged.
• keratinous materials which have been exposed to environments which tend to be damaging toward same exhibit a greater tendency to undergo more favorable polymerization reactions, i.e., more accelerated grafting rates.
• This situation can probably be explained by reference to the fact that the damaged keratin fiber for example is of more porous structure the latter condition being more conducive to penetration of reagents into the fiber mass.
• the term damaged within the context of the present invention would connote, for example, bleached hair, permanently waved hair, etc.
• the adaptability of a given hair sample to the process of the present invention can be enhanced, for example, by subjecting the sample to one or more preliminary bleaching treatments with plural treatments usually leading to more favorable results.
• a process for the modification of keratinous materials which comprises treating at a temperature of from to 200F. a keratinous substrate which has previously been treated with reducing agent and thoroughly rinsed to remove residual reducing agent, with an effective amount of a solution consisting essentially of 1. as the sole catalyst component, a free radical liberating peroxide catalyst material capable of initiating the polymerization of ethylenically unsaturated vinyl monomer compounds; 2. a vinyl monomer, containing at least one grouping of the formula:
• CH C said monomer undergoing polymerization in the presence of said peroxide catalyst, said process being effected in the presence of from 0.025 to 40 moles per mole of monomer of a water-soluble halide of an alkali metal or ammonium, the concentration of said monomer being from 1 to 30 percent by weight of the total solution, the molar ratio of said peroxide catalyst to monomer being 0.001 :1 to 5:1; and
• a process according to claim 1 wherein said peroxide catalyst material is potassium persulfate.
• said monomer is a compound of the following structural formula wherein R is selected from the group consisting of hydrogen and lower alkyl and R is selected from the group consisting of a. carbalkoxy of the formula -COOR wherein R is selected from the group consisting of hydrogen, alkyl containing from one to 20 carbon atoms, alkenyl containing from three to 10 carbon atoms, hydroxyalkyl containing from two to 10 carbon atoms, vicinal epoxyalkyl containing from one to carbon atoms and mono and dialkylaminoalkyl each of said alkyl containing from one to four carbon atoms and b. amido of the following structural formula wherein R and R are independently selected from the group consisting of hydrogen, lower alkyl or together represent the atoms necessary to complete a grouping of the formula

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• 1969
  • 1969-05-29 US US829096A patent/US3676550A/en not_active Expired - Lifetime
  • 1969-05-29 US US829097A patent/US3633591A/en not_active Expired - Lifetime
• 1970
  • 1970-05-25 DE DE2025454A patent/DE2025454C2/de not_active Expired
  • 1970-05-25 FR FR7018913A patent/FR2043768B1/fr not_active Expired
  • 1970-05-26 GB GB2520570A patent/GB1311902A/en not_active Expired
  • 1970-05-26 GB GB5902772A patent/GB1318170A/en not_active Expired
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  • 1970-05-28 NO NO2039/70A patent/NO132920C/no unknown
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  • 1970-05-29 JP JP45045770A patent/JPS4925334B1/ja active Pending

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