CH470521A - Process for the treatment of keratin textile fibers - Google Patents
Process for the treatment of keratin textile fibersInfo
- Publication number
- CH470521A CH470521A CH64066A CH64066A CH470521A CH 470521 A CH470521 A CH 470521A CH 64066 A CH64066 A CH 64066A CH 64066 A CH64066 A CH 64066A CH 470521 A CH470521 A CH 470521A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- polymer
- polysulfhydryl
- radical
- hydrogen atom
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 11
- 239000000835 fiber Substances 0.000 title claims description 9
- 239000004753 textile Substances 0.000 title claims description 6
- 102000011782 Keratins Human genes 0.000 title claims 3
- 108010076876 Keratins Proteins 0.000 title claims 3
- 229920000642 polymer Polymers 0.000 claims description 13
- -1 alkylene radical Chemical class 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 239000012736 aqueous medium Substances 0.000 claims description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 3
- 230000002787 reinforcement Effects 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 2
- ORTFAQDWJHRMNX-UHFFFAOYSA-M oxidooxomethyl Chemical compound [O-][C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-M 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 229920001577 copolymer Polymers 0.000 description 7
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 229960003151 mercaptamine Drugs 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 150000008064 anhydrides Chemical group 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000000985 reactive dye Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- 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
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/356—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of other unsaturated compounds containing nitrogen, sulfur, silicon or phosphorus atoms
- D06M15/3566—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of other unsaturated compounds containing nitrogen, sulfur, silicon or phosphorus atoms containing sulfur
-
- 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
- A61K8/8158—Homopolymers or copolymers of amides or imides, e.g. (meth) acrylamide; Compositions of derivatives of such polymers
-
- 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
- A61Q5/04—Preparations for permanent waving or straightening the hair
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/34—Introducing sulfur atoms or sulfur-containing groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/44—Preparation of metal salts or ammonium salts
-
- 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
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/263—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof
- D06M15/273—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof of unsaturated carboxylic esters having epoxy groups
- D06M15/2735—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof of unsaturated carboxylic esters having epoxy groups of unsaturated carboxylic esters having mercapto groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2800/00—Copolymer characterised by the proportions of the comonomers expressed
- C08F2800/10—Copolymer characterised by the proportions of the comonomers expressed as molar percentages
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2810/00—Chemical modification of a polymer
- C08F2810/50—Chemical modification of a polymer wherein the polymer is a copolymer and the modification is taking place only on one or more of the monomers present in minority
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Textile Engineering (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Cosmetics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Description
Procédé pour le traitement des fibres textiles kératiniques Le brevet principal a pour objet un procédé de trai tement des fibres textiles kératiniques, en vue au moins de leur renforcement mécanique, par application sur les dites fibres d'au moins un polymère polysulfhydrylé en solution dans un milieu aqueux, polymère répondant de préférence à la formule générale
EMI0001.0000
dans laquelle R désigne un radical alcoylène comportant de préfé rence 2 à 4 atomes de carbone, éventuellement substitué par des alcoyles inférieurs pouvant avoir jusqu'à 4 ato mes de carbone, un radical carboxyle ou carbalcoxy ;
R' désigne H ou un radical alcoyle inférieur<B>;</B> R" et R\ désignent H, un radical alcoyle inférieur, un radical phényle ou un radical alcoxy inférieur, R" et R\ pouvant être identiques ou différents, et n est un nombre entier, supérieur à 1 et inférieur à 25. Ce procédé est connu car il est également décrit dans le brevet belge N 629769.
De nouvelles recherches effectuées par la Société titu laire lui ont permis de découvrir de nouveaux polymères @@fhydrylés qui, par rapport aux polymères décrits dans le brevet principal, présentent l'avantage d'une plus grande plasticité.
La présente invention a pour objet un procédé pour le traitement des fibres textiles kératiniques en vue au moins de leur renforcement mécanique, caractérisé par le fait que l'on applique sur lesdites fibres au moins un polymère polysulfhydrylé dans un milieux aqueux, le polymère répondant à la formule suivante
EMI0001.0002
dans laquelle R désigne un radical alcoylène à chaîne droite com portant de préférence de 2 à 4 atomes de carbone, pou vant porter des restes alcoyles latéraux d'au plus 4 ato mes de carbone, ou être substitué par un radical carb oxyle ou par un groupe carbalcoxy ; R' représente un atome d'hydrogène ou un alcoyle inférieur tel que - CH3 ou - C2H5 ;
R" et R"' représentent un atome d'hydrogène, un radical alcoyle inférieur, un radical phényle ou un radi cal alcoxy inférieur, R" et R"' pouvant être identiques ou différents ; n est un nombre entier.
Dans des mises en oeuvre avantageuses, R" et R\ représentent tous deux un atome d'hydrogène. Exemple On prépare un composé ayant pour formule
EMI0002.0000
en condensant, comme indiqué ci-après 3-mercapto-éthyl- amine sur le copolymère anhydride maléique/acétate de vinyle.
A cet effet on utilise comme produit de départ un copolymère acétate de vinyle/anhydride maléique obtenu de façon connue par copolymérisation dans le toluène de quantités équimoléculaires d'acétate de vinyle et d'anhy dride maléique en présence de peroxyde de benzoyle agissant comme catalyseur.
Le copolymère acétate de vinyle/anhydride maléique utilisé dans le présent exemple en solution à 1% dans le diméthylformamide et à une température de 250 C pré sente une viscosité spécifique de 0,17.
Dans ce copolymère, le rapport molaire acétate de vinyle/anhydride maléique a été déterminé par le dosage de la fonction anhydride comme étant égal à 0,93/1.
Pour effectuer la condensation de la p-mercapto- éthylamine, on place 11,35 g (0,1 mole-gramme) de chlorhydrate de p-mercaptoéthylamine et 120 cm3 d'eau dans un ballon comportant un agitateur, un thermomè tre, un tube adducteur d'azote et une ampoule à brome.
On ajoute ensuite 10 cm3 (0,1 mole-gramme) d'une solution aqueuse de soude à 40 %, de manière à libérer l'amine de son chlorhydrate.
On ajoute ensuite, en agitant et en refroidissant, 8,9 g (0,05 mole-gramme) de copolymère acétate de vinyle/anhydride maléique et 5 cm3 (0,05 mole-gramme) d'une solution aqueuse de soude à 40 %, de manière à libérer l'amine salifiant le carboxyle du copolymère.
On ajoute ensuite simultanément 8,9 g (0,05 mole- gramme) de copolymère acétate de vinyle/anhydride maléique et 5 cm3 (0,05 mole-gramme) d'une solution aqueuse de soude à 40 %.
On attend trois heures, puis on acidifie avec de l'acide chlorhydrique concentré, on lave à l'eau et on sèche le produit précipité, ce qui permet d'obtenir avec un rendement pondéral de 83 %, 21,2 grammes d'une poudre blanche qui est soluble dans l'eau à pH alcalin.
Le produit obtenu a été soumis aux déterminations analytiques suivantes
EMI0002.0009
SH <SEP> % <SEP> calculé <SEP> ........ <SEP> 12,95
<tb> SH <SEP> % <SEP> trouvé <SEP> ........ <SEP> 7,13 On a procédé à un nouveau dosage du SH après avoir réduit sa forme oxydée qui se trouve éventuelle ment présente dans le produit et on a trouvé les résultats suivants
EMI0002.0010
SH <SEP> % <SEP> calculé <SEP> ........ <SEP> 12,95
<tb> SH <SEP> % <SEP> trouvé <SEP> ........ <SEP> 12,17 Pour traiter 10 g de filés de laine, on réalise tout d'abord la solution suivante
EMI0002.0011
Polymère <SEP> polysulfhydrylé, <SEP> préparé <SEP> comme <SEP> indi qué <SEP> ci-dessus <SEP> - <SEP> . <SEP> . <SEP> . <SEP> . <SEP> . <SEP> . <SEP> . <SEP> . <SEP> . <SEP> . <SEP> . <SEP> . <SEP> . <SEP> . <SEP> . <SEP> . <SEP> .
<SEP> . <SEP> . <SEP> . <SEP> . <SEP> . <SEP> . <SEP> 3 <SEP> g
EMI0002.0012
Solution <SEP> de <SEP> NH4OH <SEP> à <SEP> 221, <SEP> Baumé <SEP> . <SEP> . <SEP> . <SEP> . <SEP> . <SEP> . <SEP> . <SEP> . <SEP> . <SEP> . <SEP> 6 <SEP> cc
<tb> Eau <SEP> q. <SEP> s. <SEP> p. <SEP> . <SEP> . <SEP> . <SEP> ....... <SEP> . <SEP> . <SEP> . <SEP> . <SEP> . <SEP> . <SEP> . <SEP> . <SEP> . <SEP> . <SEP> . <SEP> . <SEP> . <SEP> . <SEP> . <SEP> . <SEP> 100 <SEP> cc On immerge ensuite pendant 15 minutes les filés de laine dans cette solution à température ambiante.
Après essorage et un éventuel rinçage à l'aide d'une solution acide telle qu'une solution d'acide acétique ou d'acide sulfurique N/10, les filés de laine sont aptes à être teints dans de bonnes conditions à l'aide de colo rants réactifs tels que, par exemple, les colorants vendus sous la marque (c Cibachrone par la Société Ciba de Bâle. ,
Process for the treatment of keratinous textile fibers The main patent relates to a process for treating keratinous textile fibers, with a view at least to their mechanical reinforcement, by application to said fibers of at least one polysulfhydryl polymer in solution in a aqueous medium, polymer preferably corresponding to the general formula
EMI0001.0000
in which R denotes an alkylene radical preferably comprising 2 to 4 carbon atoms, optionally substituted by lower alkyls possibly having up to 4 carbon atoms, a carboxyl or carbalkoxy radical;
R 'denotes H or a lower alkyl radical <B>; </B> R "and R \ denote H, a lower alkyl radical, a phenyl radical or a lower alkoxy radical, R" and R \ possibly being identical or different, and n is an integer, greater than 1 and less than 25. This process is known because it is also described in Belgian patent N 629769.
New research carried out by the Company has enabled it to discover new polymers @@ fhydrylés which, compared to the polymers described in the main patent, have the advantage of greater plasticity.
The present invention relates to a process for the treatment of keratinous textile fibers with a view at least to their mechanical reinforcement, characterized in that at least one polysulfhydryl polymer is applied to said fibers in an aqueous medium, the polymer corresponding to the following formula
EMI0001.0002
in which R denotes a straight chain alkylene radical comprising preferably from 2 to 4 carbon atoms, able to bear side alkyl residues of at most 4 carbon atoms, or be substituted by a carboxyl radical or by a carbalkoxy group; R 'represents a hydrogen atom or a lower alkyl such as - CH3 or - C2H5;
R "and R" 'represent a hydrogen atom, a lower alkyl radical, a phenyl radical or a lower alkoxy radi cal, R "and R"' possibly being identical or different; n is an integer.
In advantageous embodiments, R "and R \ both represent a hydrogen atom. Example A compound is prepared having the formula
EMI0002.0000
by condensing, as indicated below 3-mercapto-ethyl-amine on the maleic anhydride / vinyl acetate copolymer.
For this purpose, a vinyl acetate / maleic anhydride copolymer obtained in known manner by copolymerization in toluene of equimolecular quantities of vinyl acetate and maleic anhydride in the presence of benzoyl peroxide acting as a catalyst is used as starting product.
The vinyl acetate / maleic anhydride copolymer used in the present example in a 1% solution in dimethylformamide and at a temperature of 250 ° C. has a specific viscosity of 0.17.
In this copolymer, the vinyl acetate / maleic anhydride molar ratio was determined by assaying the anhydride function as being equal to 0.93 / 1.
To carry out the condensation of p-mercaptoethylamine, 11.35 g (0.1 mole-gram) of p-mercaptoethylamine hydrochloride and 120 cm3 of water are placed in a flask comprising a stirrer, a thermometer, a nitrogen adductor tube and a bromine bulb.
Then 10 cm3 (0.1 mole-gram) of a 40% aqueous sodium hydroxide solution is added, so as to free the amine from its hydrochloride.
Then added, with stirring and cooling, 8.9 g (0.05 mole-gram) of vinyl acetate / maleic anhydride copolymer and 5 cm3 (0.05 mole-gram) of an aqueous solution of sodium hydroxide at 40 %, so as to release the amine salifying the carboxyl of the copolymer.
Then 8.9 g (0.05 mol-gram) of vinyl acetate / maleic anhydride copolymer and 5 cm3 (0.05 mol-gram) of a 40% aqueous sodium hydroxide solution are added simultaneously.
Wait three hours, then acidify with concentrated hydrochloric acid, wash with water and dry the precipitated product, which allows to obtain with a weight yield of 83%, 21.2 grams of a white powder which is soluble in water at alkaline pH.
The product obtained was subjected to the following analytical determinations
EMI0002.0009
SH <SEP>% <SEP> calculated <SEP> ........ <SEP> 12.95
<tb> SH <SEP>% <SEP> found <SEP> ........ <SEP> 7.13 A new determination of the SH was carried out after reducing its oxidized form which is possibly present in the product and the following results were found
EMI0002.0010
SH <SEP>% <SEP> calculated <SEP> ........ <SEP> 12.95
<tb> SH <SEP>% <SEP> found <SEP> ........ <SEP> 12,17 To treat 10 g of woolen yarn, we first perform the following solution
EMI0002.0011
Polysulfhydryl polymer <SEP>, <SEP> prepared <SEP> as <SEP> indicated <SEP> above <SEP> - <SEP>. <SEP>. <SEP>. <SEP>. <SEP>. <SEP>. <SEP>. <SEP>. <SEP>. <SEP>. <SEP>. <SEP>. <SEP>. <SEP>. <SEP>. <SEP>. <SEP>.
<SEP>. <SEP>. <SEP>. <SEP>. <SEP>. <SEP>. <SEP> 3 <SEP> g
EMI0002.0012
Solution <SEP> from <SEP> NH4OH <SEP> to <SEP> 221, <SEP> Baumé <SEP>. <SEP>. <SEP>. <SEP>. <SEP>. <SEP>. <SEP>. <SEP>. <SEP>. <SEP>. <SEP> 6 <SEP> cc
<tb> Water <SEP> q. <SEP> s. <SEP> p. <SEP>. <SEP>. <SEP>. <SEP> ....... <SEP>. <SEP>. <SEP>. <SEP>. <SEP>. <SEP>. <SEP>. <SEP>. <SEP>. <SEP>. <SEP>. <SEP>. <SEP>. <SEP>. <SEP>. <SEP>. <SEP> 100 <SEP> cc The woolen yarns are then immersed for 15 minutes in this solution at room temperature.
After wringing and possibly rinsing with an acid solution such as a solution of acetic acid or N / 10 sulfuric acid, the woolen yarns are suitable for being dyed under good conditions using reactive dyes such as, for example, dyes sold under the brand (c Cibachrone by the Ciba Company of Basel.,
Claims (1)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1053068A CH473939A (en) | 1962-03-28 | 1966-01-18 | Process for the treatment of keratin textile fibers |
| CH1053168A CH473940A (en) | 1962-03-28 | 1966-01-18 | Process for the treatment of keratin textile fibers |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR892586A FR1349140A (en) | 1962-03-28 | 1962-03-28 | New compositions for the treatment of keratin fibers |
| CH398363A CH400087A (en) | 1962-03-28 | 1963-03-28 | Process for the treatment of textile keratin fibers |
| FR2337A FR87223E (en) | 1962-03-28 | 1965-01-18 | New compositions for the treatment of keratin fibers |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CH64066A4 CH64066A4 (en) | 1968-12-13 |
| CH470521A true CH470521A (en) | 1969-05-14 |
Family
ID=26235571
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH155064A CH410291A (en) | 1962-03-28 | 1963-03-28 | Composition for the treatment of non-textile keratin fibers and use of this composition for the treatment of the hair |
| CH1053068A CH473939A (en) | 1962-03-28 | 1966-01-18 | Process for the treatment of keratin textile fibers |
| CH1053168A CH473940A (en) | 1962-03-28 | 1966-01-18 | Process for the treatment of keratin textile fibers |
| CH64066A CH470521A (en) | 1962-03-28 | 1966-01-18 | Process for the treatment of keratin textile fibers |
Family Applications Before (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH155064A CH410291A (en) | 1962-03-28 | 1963-03-28 | Composition for the treatment of non-textile keratin fibers and use of this composition for the treatment of the hair |
| CH1053068A CH473939A (en) | 1962-03-28 | 1966-01-18 | Process for the treatment of keratin textile fibers |
| CH1053168A CH473940A (en) | 1962-03-28 | 1966-01-18 | Process for the treatment of keratin textile fibers |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE675224R (en) |
| CH (4) | CH410291A (en) |
| DE (1) | DE1619129A1 (en) |
| FR (2) | FR1349140A (en) |
| GB (1) | GB1132822A (en) |
| NL (1) | NL6600658A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL290721A (en) * | 1962-03-28 | 1900-01-01 | Oreal | |
| AT257843B (en) * | 1963-04-18 | 1967-10-25 | Oreal | Process for the permanent deformation of hair and means for carrying out the process |
-
1962
- 1962-03-28 FR FR892586A patent/FR1349140A/en not_active Expired
-
1963
- 1963-03-28 CH CH155064A patent/CH410291A/en unknown
-
1965
- 1965-01-18 FR FR2337A patent/FR87223E/en not_active Expired
-
1966
- 1966-01-17 BE BE675224A patent/BE675224R/en active
- 1966-01-18 CH CH1053068A patent/CH473939A/en unknown
- 1966-01-18 CH CH1053168A patent/CH473940A/en unknown
- 1966-01-18 GB GB2375/66A patent/GB1132822A/en not_active Expired
- 1966-01-18 NL NL6600658A patent/NL6600658A/xx unknown
- 1966-01-18 CH CH64066A patent/CH470521A/en unknown
- 1966-01-18 DE DE19661619129 patent/DE1619129A1/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| GB1132822A (en) | 1968-11-06 |
| DE1619129A1 (en) | 1971-04-01 |
| NL6600658A (en) | 1966-07-19 |
| CH410291A (en) | 1966-03-31 |
| CH1053068A4 (en) | 1969-02-28 |
| CH473940A (en) | 1969-07-31 |
| CH64066A4 (en) | 1968-12-13 |
| FR87223E (en) | 1966-07-01 |
| FR1349140A (en) | 1964-01-17 |
| CH473939A (en) | 1969-07-31 |
| CH1053168A4 (en) | 1969-02-28 |
| BE675224R (en) | 1966-07-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PLZ | Patent of addition ceased |