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    Simultaneously dyeing and resin finishing textiles
    4.
    发明专利
    Simultaneously dyeing and resin finishing textiles 未知

    公开(公告)号：GB948694A

    公开(公告)日：1964-02-05

    申请号：GB707162

    申请日：1962-02-23

    Applicant: BASF AG

    Inventor： WILHELM HANS ,  LOUIS GERD ,  MAHLING DIETER ,  LANGE GUENTER ,  WEIDINGER HANS ,  CRAEMER KARL ,  SCHWINDT WOLFGANG ,  KREHBIEL GUENTER

    IPC: C08F16/12 ,  C08F20/62 ,  C08F28/00 ,  C09B69/10 ,  D06L3/12 ,  D06M20060101 ,  D06P20060101 ,  D06P1/00

    Abstract: Reaction products of polymers containing reactive groups with dyes also containing reactive groups are applied to textile materials and cross-linked with or without a cross-linking agent, by way of the remaining reactive groups of the polymer. The dyestuffs may contain a large number of specified reactive groups including acid amide, ureido, carboxylic acid, and suplhonic acid and their ester groups, aldehyde, epoxy, N-methylol and N-methylol ether groups. The polymers may be homo- or copolymers made up of monomers bearing suitable reactive groups as well as inert monomers or the reactive groups may be introduced after polymerization. The specified reactive groups are: amino, hydroxyl, aldehyde, carboxylic acid and ester groups, lactone, carbonamide carbonimide, carbamido, melamine, dicyandiamide, carbamate, epoxy, N-methylol, N-methylol ether, chlorhydrin, isocyanate, active methylene, acid chloride and anyhdride groups, reactive halogen atom, C=C bonds capable of addition and not taking part in the polymerization thiourea the thioisocyanate groups. The polymers may be prepared by solution, emulsion, bulk or precipitation polymerization. In the examples the following copolymers are reacted with monoazo dyes containing N-methylol groups and are prepared from: (3) butyl acrylate and N-methylolacrylamide in aqueous emulsion (7) acrylamide, butyl acrylate, vinyl propionate, acrylonitrile and vinyl acetate in toluene-butanol (1:1) solution, (8) acrylamide N-methylolmethacrylamide and ethyl acrylate by precipitation from butanol, (9) to (13) as in (3), (14) isobutyl acrylate, acrylonitrile, vinyl chloride and N-methylolmethacrylamide in aqueous dispersion (15) butyl acrylate, acrylonitrile and N-methylolmethacrylamide from aqueous dispersion, (16) butyl acrylate, styrene and N-methylolmethacrylamide from aqueous dispersion, (17) butyl acrylate, vinyl chloride, methyl acrylate and acrylamide from aqueous disperson and (18) as in (15). The following cross-linking agents are employed: the tetrabutyl ether of tetramethylolglyoxaldiureine, butanediol-1, 4-bis-(N-methylolurethane) and a urea-formaldehyde precondensate partly etherified with methanol. Specifications 744,877, 799,781, 842,802, 850,977, 900,764 and 946,471 are referred to.ALSO:Dyeing and/or printing textiles and simultaneously resin finishing them in a process wherein a polymer containing reactive groups is reacted by way of part of said reactive groups with a dye also containing reactive groups, the macromolecular coloured compound thus obtained is applied to the textiles and cross-linked by way of the remaining reactive groups, or the polymer containing reactive groups, the reactive dye and, if necessary, a cross linking agent are applied to the textiles and the reactions are effected in a simple operation on the fibre. The textiles may be of cotton, spun rayon, cellulose acetate and triacetate, synthetic polyamides, acrylonitrile polymers and copolymers and especially polypropylene. The polymers may be homopolymers or copolymers and may be prepared from a large number of specified monomers by aqueous or organic solution polymerization, aqueous emulsion, bulk or precipitation polymerization. Alternatively polymers may be employed in which the reactive groups are introduced after polymerization. The dyestuffs may contain any of a large number of specified reactive groups including N-methylol acid amide, acid imide, ureido, carboxylic acid sulphonic acid ester aldehyde, N-methylol and N-methylol ether groups. The polymers, dyestuff and, if required cross-linking agents may be applied all together, separately or in any desired combination. A dyeing step at 60-110 DEG C. is advantageous before the final curing at temperatures up to 200 DEG C. The polymer solutions or dispersions may further contain other textile finishing resins, including urea-and melamine-formaldehyde condensates as well as many natural, synthetic and semi-synthetic known substances. The composition may be applied by padding or printing. The polymers of the present process may also be used for bonding non-woven fabrics, as a resin over a naphthol bottoming or under amiline black and, when a suitable discharging agent (e.g. sodium hydroxymethane sulphonate) is included for discharging direct dyes. Examples of dyeing and finishing are given. Specifications 744,877, 799,781, 842,802, 850,977, 900,764 and 946,471 are referred to.

    Colored crosslinkable and crosslinked polymers and their production
    5.
    发明专利
    Colored crosslinkable and crosslinked polymers and their production 未知

    公开(公告)号：GB946472A

    公开(公告)日：1964-01-15

    申请号：GB707062

    申请日：1962-02-23

    Applicant: BASF AG

    Inventor： LANGE GUENTER ,  WEIDINGER HANS ,  SETZER LUDWIG ,  LOUIS GERD ,  MAHLING DIETER ,  WILHELM HANS

    IPC: C08F8/00 ,  C08F8/30 ,  C09B62/00 ,  C09B69/10 ,  D04H1/587 ,  D04H1/645

    Abstract: Polymeric compounds united by chemical combination with dyes are made by reacting a homopolymer or copolymer containing groups that enable to be reacted with other compounds by condensation or addition reactions with a dye also containing reactive groups, and cross-linking the polymer by way of the reactive groups of the polymer which are still available, either simultaneously or subsequently. Monomers containing reactive groups from which such polymers may be prepared are acrolein, acrylamide, N-methylolacrylamide, crotonamide, ethacrylamide, chloroacrylamide, phenylacrylamide, maleic, fumaric, citraconic and itaconic diamides, N-acryloyl and N-methacryloyl ureas and dicyanodiamides amino-allyloxytriazines, glyoxalmonocureine allyl ether, glycidyl acrylate and butanediol monoacrylate. Such monomers may be copolymerized with monomers such as styrene, butadiene, isoprene, nitriles, amides, esters, anhydrides and salts of acrylic, methacrylic, crotonic, maleic, fumaric, itaconic and citraconic acids, vinyl acetate, propionate or butyrate, vinyl chloride and bromide, allyl esters, vinyl carbazole pyridine, imidazole and quinoline and vinyl pyrrolidone and caprolactam. Alternatively, reactive groups may be introduced into polymers by after-treatment, e.g. by hydrolysis, reduction or halogenation. Dyes containing reactive groups are specified in Specifications 744,877, 779,781, 842,802, 850,977, 900,764 and 946,471. The polymers may contain self cross-linking groups, in which case the action of heat or change in pH value may effect cross-linking, or an external cross-linking agent may be employed. The examples describe the following processes: (1) a copolymer of butyl acrylate, styrene, and N-methylolmethacrylamide in aqueous dispersion is mixed with an aqueous solution of the coupling product of diazotized N-(p-aminophenyl)-glyoxal-diureine and gamma - acetylaminonaphthol-(1)-3,6-di-sulphonic acid and ammonium nitrate, and from the resulting dispersion a violet-red film is produced which cross-links on heating at 140 DEG C.; (2) a non-woven fabric is impregnated with a mixture of an aqueous dispersion of a copolymer of butylacrylate and acrylamide, an aqueous solution of a coupling product of diazotized N-(p-aminophenyl)-glyoxaldiureine with 1-(p-sulphophenyl) -3- methylpyrazolone-(5) which has been reacted with formaldehyde, dimethylol urea and ammonium nitrate, and the impregnated fabric is dried and heated at 150 DEG C.; (3) a mixture of a copolymer of acrolein, butyl acrylate and styrene, 4-azophenylacetoacetic acid and piperazine dissolved in a toluene-butanol solvent is applied to a substrate and heated at 120 DEG C.; (4) an aqueous solution containing a copolymer of acrylamide, tert.-butyl acrylate and ethyl acrylate is mixed with the dye of (2), dimethylolurea and ammonium nitrate, applied to paper and heated at 150 DEG C.; (5) a mixture of a copolymer of acrylamide, N-methylolacrylamide and ethyl acrylate, the dye of (1), the di-N-methylolurethane of 1,4-butanediol and ammonium nitrate is dissolved in water, applied to wood pulp and dried at 150 DEG C.; (6) the dye obtained by coupling diazotized p-aminophenylglyoxaldiureine with 1-naphthol-4-sulphonic acid and reaction with formaldehyde, the dimethylolurethane of 1,4-butanediol and ammonium nitrate are added to an aqueous solution of a copolymer of acrylamide, methacrylamide, and methyl acrylate, the resulting composition is applied to paper and heated at 160-170 DEG C.; and (7) the coupling product of diazotized p-aminophenylurea and 4-tert.-butylphenol and reacted with formaldehyde, and hexamethylene diisocyanate are added to an ethanol solution of a copolymer of butylacrylate, butanediol monoacrylate and acrylamide, and the resulting solution is applied to glass fabric and heated at 160-170 DEG C. Specification 877,102 also is referred to. The Specification describes also the preparation of the copolymers of the above Examples by the following processes: (1) and (2) aqueous emulsion polymerization in the presence of potassium persulphate and the sulphation product of an oxyethylated fatty alcohol; (3) solution polymerization in a toluene-butanol mixture in the presence of benzoyl peroxide; (4) solution polymerization in butanol in the presence of azodiisobutyronitrile; (5) precipitation polymerization in butanol in the presence of benzoyl peroxide and sodium hydroxymethanesulphinate; (6) aqueous solution polymerization in the presence of potassium persulphate and sodium hydroxymethane-sulphinate; and (7) solution polymerization in ethanol in the presence of azodiisobutyronitrile.ALSO:Paper and wood are coated with a toluenebutanol solution of a copolymer of acrolein, butyl acrylate and styrene, 4-azophenylacetoacetic acid anilide as a dyestuff reactive with the copolymer, and piperazine as a cross-linking agent for the copolymer, and then heated at 120 DEG C. to produce transparent yellow coatings. Specifications 744,877, 779,781, 842,802, 850,977, 877,102, 900,764 and 946,471 are referred to.ALSO:Fabrics are coloured by impregnating them with a mixture comprising a polymer and a dyestuff reactive therewith, and, if the polymer is not self-cross-linking, a cross-linking agent therefor. Examples describe processes in which: (2) a non-woven fabric is impregnated with an aqueous composition comprising the coupling product of diazotized N-(p-aminophenyl)-glyoxaldiureine with 1-(p-sulphophenyl)-3-methylpyrazolone-(5) which has been reacted with formaldehyde, dimethylol urea and a dispersion of a copolymer of butyl acrylate and methacrylamide, followed by drying and heating the fabric at 150 DEG C.; and (7) glass fabric is impregnated with an ethanol solution of a copolymer of butyl acrylate, butanediol monoacrylate and acrylamide containing hexameltrylene diisocyanate and the coupling product of diazotized p-aminophenylurea and 4-tertbutylphenol reacted with formaldehyde, and the dried fabric is heated at 160-170 DEG C. Specifications 744, 877, 779, 781, 842, 802, 850, 977, 877, 102, 900, 764 and 946, 471 are referred to.

    Process for the simultaneous dyeing and resin finishing of textiles
    7.
    发明专利
    Process for the simultaneous dyeing and resin finishing of textiles 未知

    公开(公告)号：GB914354A

    公开(公告)日：1963-01-02

    申请号：GB2443161

    申请日：1961-07-06

    Applicant: BASF AG

    Inventor： WILHELM HANS ,  LOUIS GERD ,  LANGE GUENTER ,  PENNING ERNST ,  WEIDINGER HANS

    IPC: C08F2/22 ,  C08F2/44 ,  C08F16/12 ,  C08F20/62 ,  C08F28/00 ,  C09B69/10 ,  D06L3/12 ,  D06M15/39 ,  D06P1/00

    Abstract: Emulsion copolymers obtainable by copolymerization in the emulsion of (a) a dye which contains a polymerizable olefinic double bond, (b) one or more non-coloured compounds which contain polymerizable olefinic double bonds and groups accessible to cross-linking by addition or condensation and, optionally, (c) one or more polymerizable non-coloured compounds (inert to cross-linking) used for the production of plastics are employed for simultaneously dyeing and finishing textiles and are subsequently cross-linked either alone or with the aid of (d) suitable bi- or polyfunctional compounds, either by condensation or addition. The chromophoric monomers (a) may be based on dyes of the azo, anthraquinone, triarylmethane, phthalocyanine, phenazine and oxazine series (see Group IV(c)). While many components (b) and (c) are specified those mentioned in the examples are (b) N-methylolmethacrylamide, N-methylol-acryloylurea, N-methylol-N-acryloylmaleic acid imide, butanediol monoacrylate, methacrylamide, acrylic acid and 2:4-diamino-6-acryloylaminoethylene-1:3:5-triazine and (c) ethyl acrylate, butyl acrylate, methyl methacrylate, acrylonitrile, styrene, vinyl propionate and vinyl chloride. The copolymers, whose solid content is preferably 25-50%, may be prepared in the presence of polymerization initiators such as hydrogen peroxide and potassium persulphate. Cross-linking may be effected by heating or changing the pH with or without the aid of many specified components (d) and other catalysts. The components (d) mentioned in the examples are the bisulphite compounds of hexamethylene di-isocyanate and toluylene di-isocyanate, N,N1-dimethylolurea and its methyl ethers, the N,N1-dimethylolated diurethane of butane-diol-(1,4), the reaction product of pentaerythritol and epichlorhydrin and an etherified urea-formaldehyde resin precondensate. Examples are given of the preparation of copolymers and their employment in dyeing and printing fabrics.ALSO:Textiles are simultaneously dyed and finished by treating with emulsion copolymers obtainable by copolymerization in the emulsion of (a) a dye which contains a polymerizable olefinic double bond, (b) one or more non-coloured compounds which contain polymerizable olefinic double bonds and groups accessible to cross-linking by addition or condensation and, optionally, (c) one or more polymerizable non-coloured compounds (inert to cross-linking) used for the production of plastics, and subsequently crosslinking the copolymer either alone or with the aid of (d) suitable bi- or polyfunctional compounds, either by condensation or addition. The chromophoric monomers (a) may be based on dyes of the azo, anthraquinone, triarylmethane, phthalocyanine, phenazine and oxazine series; suitable dyes are described in Specifications 830,876, 858,183, 875,946, 877,402 and 879,071, German Specification 1,010,063 and French Specification 1,118,705. Many components (b) are specified, among which are N-methylolmethacrylamide, N-methylol-N-acryloylmaleic acid imide, butanediol monoacrylate, methacrylamide and acrylic acid; many components (c) are also specified, those mentioned in the examples being ethyl acrylate, butyl acrylate, methyl methacrylate, acrylonitrile, styrene, vinyl propionate and vinyl chloride. The copolymer emulsions, whose solid content is preferably 25-50%, may also contain the usual emulsifiers and protective colloids, as well as a thickener, when the copolymer is used as a printing paste. Cross-linking may be effected by heating or changing the pH with or without the aid of many specified components (d) and other catalysts. Examples are given of the preparation of copolymers and the dyeing and printing of fabrics of cotton (woven and non-woven), rayon staple, calico and regenerated cellulose. Other specified materials are of wool, silk, polyamide, cellulose acetate, polyvinyl alcohol and polymers and copolymers of acrylonitrile.

    9.
    发明专利
    未知

    公开(公告)号：DE1115926B

    公开(公告)日：1961-10-26

    申请号：DEB0057934

    申请日：1960-05-20

    Applicant: BASF AG

    Inventor： WILHELM HANS ,  PENNING ERNST ,  LOUIS GERD ,  LANGE GUENTER ,  WEIDINGER HANS

    IPC: C08F2/04 ,  C08F2/22 ,  C08F2/44 ,  C08F16/12 ,  C08F20/62 ,  C08F28/00 ,  C09B69/10 ,  D06L3/12 ,  D06L4/60 ,  D06M15/39 ,  D06P1/00

    Abstract: Coloured cross-linked or cross-linkable copolymers are obtained by copolymerizing at least one olefinic monomer dyestuff, containing, in addition to the unsaturated at least one olefinic monomer polymerizable group, a group capable of condensation or addition, and, if desired, at least one further copolymerizable monomer, and then, if desired, cross-linking the resulting copolymers by way of the groups capable of condensation or addition. The dyestuff monomers may be of the azo, anthraquinone, phthalocyanine, triarylmethane, phenazine, or oxazine type, such dyestuffs being described in Specifications 779,781, 830,876, 858,183, 875,946 and 879,071. The examples describe the following processes: (1) emulsion copolymerizing butyl acrylate, N-methylol methacrylamide and an unsaturated azo dyestuff to yield a copolymer which cross-links on drying; (2) emulsion copolymerizing acrylonitrile, butyl acrylate, N-methyldimethacrylamide and an unsaturated azo dyestuff; (3) as in (2) but using an unsaturated anthraquinone dyestuff; (4) emulsion copolymerizing styrene, methylolacrylamide, butyl acrylate, N-methylolacryloylurea and acryloylaminobenzene, and cross-linking the resulting polymer by heating in the presence of ammonium nitrate; (5) emulsion polymerizing ethyl acrylate, vinyl propionate, N-methylolmethacrylamide, N-methylol maleimide and an unsaturated azo dyestuff and cross-linking the resulting copolymer by heating; (6) emulsion copolymerizing butyl acrylate, acrylonitrile, butane-diol monoacrylate and an unsaturated azo dyestuff, and cross-linking the resulting copolymer with hexamethylene diisocyanate; (7) emulsion copolymerizing butyl acrylate, methacrylamide and an unsaturated azo dyestuff and cross-linking the product by heating with dimethylol urea; (8) cross-linking the copolymer of (7) by heating with N,N1-dimethylolbutane-(1,4)-diurethane; (9) emulsion copolymerizing butyl acrylate, acrylonitrile, acrylic acid and an unsaturated azo dyestuff, neutralising the carboxyl groups in the product with ammonia, and heating it with a polyepoxide derived from pentaerythritol and epichlorohydrin; (10) emulsion copolymerizing butyl acrylate, N-methylolacrylamide and an unsaturated azo dyestuff, mixing the resulting dispersion with an acrylamide/methacrylamide copolymer, sawdust and a mixture of N,-N1 dimethylolurea monomethyl and dimethyl ethers, drying the composition and moulding at 150 DEG C.; (11) emulsion copolymerizing butyl and ethyl acrylates, methyl methacrylate methacrylamide and an azo dyestuff containing vinyl ether groups, adding a mixture of N,N1-dimethylol urea monomethyl and dimethyl ethers and heating in the presence of ammonium nitrate; (12) emulsion copolymerizing butyl acrylate, N-methylol methacrylamide, a triazine derivative of acrylamide and an unsaturated azo dyestuff, mixing the dispersion with N,N1-dimethylolbutane-(1, 4)-diurethane and ammonium nitrate and subjecting the mixture to heat; (13) emulsion copolymerizing butyl acrylate, acrylamide, vinyl chloride and an unsaturated azo dyestuff, mixing the dispersion with N,N1-dimethylol urea and cross-linking at 130 DEG C.; (14) solution copolymerizing butyl acrylate, acrylamide, methyl methacrylate, butanediol monoacrylate and an azo dyestuff containing vinyl ether groups and cross-linking the product with hexamethylene diisocyanate; (15) solution copolymerizing methyl methacrylate butyl acrylate, acrolein and an unsaturated azo dyestuff, and cross-linking the product with the glycol ester of bisacetoacetic acid; (16) solution copolymerizing butyl acrylate, vinyl propionate, methacrylamide, N-methylol methacrylamide and an unsaturated anthraquinone dyestuff, and heating the product after the addition thereto of phosphoric acid; (17) as in (3) but with the use of tetramethylolacetylene diurea tetrabutyl ether at the cross-linking stage and with the addition of wood pulp to the curable mixture; (18) bulk copolymerizing methyl methacrylate, butanediol monoacrylate and an unsaturated azo dyestuff in the presence of dibutylphthalate until the product is syrupy, discontinuing polymerization and then heating the product with hexamethylene diisocyanate; (19) solution copolymerizing vinyl pyrrolidone, methyl methacrylate, butyl acrylate, N-methylol methacrylamide and a copper phthalocyanine dyestuff containing sulphonic groups which have been reacted with N-acryloyl - p - phenylene diamene, and heating the product with tetramethylolacetylenediure tetrabutyl ether; and (20) solution copolymerizing acrylamide ethyl acrylate, N-methylol methacrylamide and an unsaturated azo dyestuff, and heating the product with tetramethylolacetylene diurea.ALSO:Surfaces of paper, wood and metal are coated with coloured copolymers obtained from olefinic monomer dyestuffs, monomers containing cross-linkable groups, and, if desired, other copolymerizable monomers. In examples: (2) wood and paper are coated with an aqueous dispersion of a copolymer of butyl acrylate, N-methylol methacrylamide and an unsaturated azo dyestuff, and the coating is dried at 180 DEG C.; (13) paper and a metal plate are coated with an aqueous dispersion containing a copolymer of butyl acrylate, vinyl chloride, acrylamide and an unsaturated azo dyestuff, N,N1-dimethylolurea and ammonium nitrate, the coating is dried at room temperature and cross-linked at 130 DEG C.; (15) a toluene-ethanol solution containing a copolymer of methyl methacrylate, acrolein and an unsaturated azo dyestuff, the glycol ester of bisacetoacetic acid, phosphoric acid and piperidine is brushed or sprayed on to bleached wood, and the coating is dried at 80-90 DEG C.; and (19) a tolueneethanol solution containing a copolymer of vinyl pyrrolidone, methyl methacrylate, butyl acrylate, N-methylol methacrylamide and a copper phthalocyanine dyestuff containing sulphonic groups which have been reacted with N-acryloyl-p-phenylene diamine, tetramethylolacetylenediurea tetrabutyl ether and glacial acetic acid is brushed on to wood or paper and dried at 140 DEG C. Specifications 779,781, 830,876, 858,183, 875,946 and 879,071 are referred to.

    Macromolecular polyformaldehyde stabilised against oxygen and heat
    10.
    发明专利
    Macromolecular polyformaldehyde stabilised against oxygen and heat 未知

    公开(公告)号：GB854278A

    公开(公告)日：1960-11-16

    申请号：GB2941259

    申请日：1959-08-28

    Applicant: BASF AG

    Inventor： LOUIS GERD ,  PENNING ERNST ,  POHLEMANN HEINZ ,  WILHELM HANS

    IPC: C08K5/46

    Abstract: Macromolecular polyformaldehyde is stabilized by mixing with it 0,01 to 10% by weight of a 2, 5-dimercapto-1, 3, 4-thiadiazole or a 2, 5-dimercapto-1, 3, 4-thiadiazole derivative of formula: wherein R1, R2, R3 and R5 represent hydrogen or alkyl, alkenyl, alkinyl, aralkyl, aryl, alkaryl or cycloalkyl radicals which may be substituted by hydroxyl, sulphydryl, carbonyl, carboxyl, amino, substituted amino, sulphonic acid or sulphonic acid ester groups, X and Y represent sulphur, sulphoxy or sulphonic groups, and R4 represents an alkylene, alkenylene, alkinylene, arylene or cycloalkylene radical, and R4 may be absent when the thiadiazole radicals are joined by a disulphide bridge. In examples acetylated macromolecular polyformaldehyde and a polyoxymethylene dimethyl ether are mixed with 2-dodecylmercapto-5 mercapto-1,3,4-thiadiazole, 2,5-bis-(3,6-dihydroxyphenyl-1)-mercapto-1,3,4-thiadiazole, 2-diethylaminoethylmercapto-5-mercapto- 1,3,4-thiadiazole and 2, 21-bis-(5, 51 dibenzylmercapto-1,3,4-thiadiazolyl)-disulphide. A list of suitable thiadiazoles is given.

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