Pigment-coloured compositions and mixtures

    公开(公告)号:GB947727A

    公开(公告)日:1964-01-29

    申请号:GB2367961

    申请日:1961-06-30

    Applicant: BASF AG

    Abstract: The invention comprises pigment-coloured compositions or mixtures characterized by a content of a bromine-containing compound of the dibenzanthrone and/or isodibenzanthrone series in the form of a preparation with up to 20%, with reference to the dye of a partly or completely oil-soluble emulsifier or an insoluble solid colloid or other protective colloid. Specified compositions include articles of polyvinyl chloride, polystyrene, polyethylene, polyesters, phenoplasts and aminoplasts. The preferred dye is the compound known as C.I. Vat Violet 9 (i.e. an isodibenzanthrone containing 13-17% bromine and up to 1% chlorine). The compositions may also contain up to 1% by weight of the dye of a water-soluble dispersing agent such as alkyl and aralkyl sulphonates, ethylene oxide condensation products and sodium lignin sulphonates. Specified oil-soluble emulsifying agents are dodecyl, oleyl, stearyl and sperm oil alcohols; dodecylphenol, octylnaphthol; oleylamine, stearylamine, coconut oil amine; stearic, lauric and abietic acids; triethanolamine mono-oleate or -stearate; oleic acid ethanolamide; the addition products of ethylene oxide with oleic acid or sperm oil alcohol; petroleum sulphonates and dialkyl sulphosuccinates. Specified protective colloids include aluminium hydroxide, silica gel, silicones, silicic acid esters, alkyd resins, styrenedivinylbenzene and styrene butadiene copolymers. In an example the p-modification of C.I. Vat Violet 9 admixed with 5-10% of an ethylene-oxide-oleic acid condensate is used to colour a mixture of polyvinyl chloride, di-isooctyl phthalate and titaniumdioxide in a violet shade. Specifications 276,518, 315,276, 325,525, 329,263 and 340,264 are referred to.ALSO:The invention comprises pigment-coloured compositions or mixtures characterized by a content of a bromine-containing compound of the dibenzanthrone and/or isodibenzanthrone series in the form of a preparation with up to 20%, with reference to the dye, of a partly or completely oil-soluble emulsifier or an insoluble solid colloid or other protective colloid. Specified compositions include pigment pastes and powders, printing colours, distempers and lacquers. The preferred dye is the compound known as C.I. Vat Violet 9 (i.e. an isodibenzanthrone containing 13-17% bromine and up to 1% of chlorine) and the preparation of its a - and b -crystal forms is described. The compositions may also contain up to 1% by weight of the dye of a water-soluble dispersing agent such as alkyl and aralkyl sulphonates, ethylene oxide condensation products and sodium ligrin sulphonates. Specified oil-soluble emulsifying agents are dodecyl, oleyl, stearyl and sperm oil alcohols; dodecylphenol, octylnaphthol; oleylamine, stearylamine and coconut oil amine; stearic, lauric and abietic acids; triethanolamine mono-oleate or stearate; oleic acid ethanolamide; the addition products of ethylene oxide with oleic acid or sperm oil alcohol; petroleum sulphonates and dialkyl sulphosuccinates. Specified protective colloids include aluminium hydroxide, silica gel, silicones, silicic acid esters, alkyd resins, styrene-divinyl-benzene and styrene-butadiene copolymers. In examples: (1) the a -form of C.I. Vat Violet 9 is prepared and acid pasted, the water used to precipitate the pigment containing dodecyl alcohol, and the pigment so prepared is ground with aluminium hydroxide and linseed oil varnish and blended with linseed oil and zinc white to give an oil paint; (2) the a -form of the pigment prepared in (1) is pasted with nitrobenzene and the nitrobenzene steam-distilled to give the b -form which is ground into a stoving lacquer comprising coconut oil alkyd resin, urea-formaldehyde resin, xylene and n-butanol; (3) the a -form of C.I. Vat Violet 9 is acid pasted and added with powerful stirring to a mixture of water, white spirit and the condensation product of 4 moles of ethylene oxide with 1 mole of sperm oil alcohol and the precipitated pigment, which is of the b -form, is ground with a solution of nitrocellulose, dibutyl phthalate, butylbenzyl phthalate, a condensation product from cyclohexanone and methy-cyclohexanone, butyl acetate, ethyl acetate and toluene to give a lacquer which may also contain titanium dioxide. Further methods of preparing the preferred pigment in the b -form are described. Specifications 276,518, 315,276, 325,525, 329,263 and 340,264 are referred to.

    Colored crosslinkable and crosslinked polymers and their production

    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

    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.

    Pulverulent pigment preparations
    5.
    发明专利

    公开(公告)号:GB918516A

    公开(公告)日:1963-02-13

    申请号:GB1924061

    申请日:1961-05-29

    Applicant: BASF AG

    Abstract: A pigment composition contains: (a) 30-70% by weight pigment of particle size 50 mm -1 m . (b) oil-soluble dispersing agent having "HLB-value" of 4-12, (c) water-soluble dispersing agent prepared by reacting 1 mole of a sulphonated phenol with 0,4-1,5 moles of urea and 0,6-2,2 moles of formaldehyde and treating product with 0,3-0,7 mole of a phenol and 0,-0,7 mole of formaldehyde. The ratio by weight of (b) to (c) may be 1:19-6:4, preferably 1:4-2:3, and there may also be present 0-5% of a wetting agent and/or protective colloid. Suitable pigments are copper phthalocyanine and chlorinated copper phthalocyanine; water-insoluble azo dyes, e.g. from 2,3-hydroxynaphthoic acid amides and aromatic diazo compounds; vat dyes, e.g. indigo and N,N1-dihydro-1,2, 21,11-anthroquinone-azine; TiO2, iron oxide and carbon black. The compound (b) is readily soluble in organic solvents and the solution is readily dispersed on shaking with water. Suitable compounds are prepared by reacting 1 mole of a long chain alcohol, a phenol, a long-chain amine, a long chain carboxylic acid or a long chain amide with 1-10 mole of ethylene and/or propylene oxide; other suitable compounds are dialkylsulphosuccinates, petroleum sulphonates, palmitic acid esters of sorbitol, and long-chain alcohols or acid amides. Particularly suitable for (c) are the products of Specification 890,150. Suitable wetting agents are: the sodium salt of sperm oil alcohol sulphuric acid ester, of 2-hydroxyoctadecane-1-sulphonic acid, or of dioctyl sulphosuccinate; the reaction product of oleic acid ethanolamide and 9 moles of ethylene oxide. Protective colloids include: maleic acidstyrene or -vinylmethyl ether copolymers; polyacrylic acid; polystyrene sulphonic acid; dextrin; and copolymers of acrylamide and methacrylamide. The compositions may be used in offset printing, for preparing aqueous paints, or for colouring paper, soaps, washing powders, or plastic dispersions. In the examples, such dispersions are used to colour: (1) polyvinyl propionate or polymethacrylic acid, (2) styrene (60 parts)-butadiene (40 parts) copolymer or polyvinyl propionate or poly methyl methacrylate or copolymers thereof, (3) and (5) as (1) and (2), using the dyes: (1) Heliogen blue B, (2) dye from diazotized 2-chloro-4-amino toluene 5-sulphonic acid and beta hydroxynaphthoic acid, (3) Indanthren blue RS, (4) Lithol red 2G (5) as (1). In Example 1, a little sodium polyacrylate is also present.

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