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  • C25D—PROCESSES FOR THE ELECTROLYTIC OR ELECTROPHORETIC PRODUCTION OF COATINGS; ELECTROFORMING; APPARATUS THEREFOR
  • C25D11/00—Electrolytic coating by surface reaction, i.e. forming conversion layers
  • C25D11/02—Anodisation
  • C25D11/04—Anodisation of aluminium or alloys based thereon
  • C25D11/18—After-treatment, e.g. pore-sealing
  • C25D11/24—Chemical after-treatment
  • C25D11/243—Chemical after-treatment using organic dyestuffs
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  • C07F9/02—Phosphorus compounds
  • C07F9/28—Phosphorus compounds with one or more P—C bonds
  • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
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  • C07F9/28—Phosphorus compounds with one or more P—C bonds
  • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
  • C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
  • C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl
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  • C07F9/28—Phosphorus compounds with one or more P—C bonds
  • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
  • C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
  • C07F9/3834—Aromatic acids (P-C aromatic linkage)
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  • C07F9/74—Aromatic compounds
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  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
  • C09B1/16—Amino-anthraquinones
  • C09B1/20—Preparation from starting materials already containing the anthracene nucleus
  • C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
  • C09B1/28—Dyes with amino groups substituted by hydrocarbon radicals substituted by alkyl, aralkyl or cyclo alkyl groups
  • C09B1/30—Dyes with amino groups substituted by hydrocarbon radicals substituted by alkyl, aralkyl or cyclo alkyl groups sulfonated
  • C09B1/303—Dyes with amino groups substituted by hydrocarbon radicals substituted by alkyl, aralkyl or cyclo alkyl groups sulfonated only sulfonated in the anthracene nucleus
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  • C09B11/00—Diaryl- or thriarylmethane dyes
  • C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
  • C09B11/10—Amino derivatives of triarylmethanes
  • C09B11/24—Phthaleins containing amino groups ; Phthalanes; Fluoranes; Phthalides; Rhodamine dyes; Phthaleins having heterocyclic aryl rings; Lactone or lactame forms of triarylmethane dyes
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  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
  • C09B31/02—Disazo dyes
  • C09B31/08—Disazo dyes from a coupling component "C" containing directive hydroxyl and amino groups
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  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B33/00—Disazo and polyazo dyes of the types A->K<-B, A->B->K<-C, or the like, prepared by diazotising and coupling
  • C09B33/02—Disazo dyes
  • C09B33/08—Disazo dyes in which the coupling component is a hydroxy-amino compound
  • C09B33/10—Disazo dyes in which the coupling component is a hydroxy-amino compound in which the coupling component is an amino naphthol
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  • C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
  • C09B35/02—Disazo dyes
  • C09B35/021—Disazo dyes characterised by two coupling components of the same type
  • C09B35/023—Disazo dyes characterised by two coupling components of the same type in which the coupling component is a hydroxy or polyhydroxy compound
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  • C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
  • C09B35/38—Trisazo dyes ot the type
  • C09B35/44—Trisazo dyes ot the type the component K being a hydroxy amine
  • C09B35/46—Trisazo dyes ot the type the component K being a hydroxy amine the component K being an amino naphthol
  • C09B35/461—D being derived from diaminobenzene
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  • C09B43/00—Preparation of azo dyes from other azo compounds
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  • C09B43/00—Preparation of azo dyes from other azo compounds
  • C09B43/11—Preparation of azo dyes from other azo compounds by introducing hydrocarbon radicals or substituted hydrocarbon radicals on primary or secondary amino groups
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  • C09B47/00—Porphines; Azaporphines
  • C09B47/04—Phthalocyanines abbreviation: Pc
  • C09B47/08—Preparation from other phthalocyanine compounds, e.g. cobaltphthalocyanineamine complex
  • C09B47/24—Obtaining compounds having —COOH or —SO3H radicals, or derivatives thereof, directly bound to the phthalocyanine radical
  • C09B47/26—Amide radicals
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  • C09B56/12—Anthraquinone-azo dyes
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  • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
  • C09B67/0032—Treatment of phthalocyanine pigments
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  • C09B69/00—Dyes not provided for by a single group of this subclass
  • C09B69/007—Dyestuffs containing phosphonic or phosphinic acid groups and derivatives

Definitions

• oxide layers produced on aluminium can be dyed, for example with inorganic pigment dyestufis.
• Organic dyestuffs are preferably used to dye aluminum oxide layers, which are simpler to apply than inorganic pigment dyestulfs and further permit the production of numerous shades.
• a Wide variety of organic dyestuffs have already been proposed for the dyeing of aluminium oxide layers, varying namely both with respect to their dyeing properties and their chemical constitution.
• the acid, water-soluble, organic dyestuffs are primarily of practical importance.
• organic dyestuffs containing at least one acid group of a pentavalent element of Group V of the Periodic System with an ordinal index between 14 and 52 are particularly suitable for dyeing aluminium oxide layers.
• aluminium oxide layers such as come in question for the purposes of the invention, such oxide layers are to be understood which are able to take up (adsorb) organic dyestuffs as a result of their adsorption capacity and their large inner surface.
• Such oxide layers can be produced both by chemical methods, e.g. by oxidation with chromates, and primarily by anodic-electrolytic methods. Suitable anodic processes are, for example, the chromium, oxalic and, primarily, the sulphuric acid process.
• aluminium not only pure aluminium, is to be understood, but also alloys thereof with various elements, such for example, as with Cu, Mg, Mr, Si, Ni, Zn, Pb, Cd, Ti, which act in a similar manner as aluminium with respect to oxidation.
• aluminium oxide By aluminium oxide, the above described oxide layers on aluminium and alloys thereof are to be understood hereinafter.
• the dyeing of aluminium oxide layers may be effected by impregnation, for example by painting, printing or spraying, or dyeing in a dye bath.
• the dyestufi is advantageously employed in a partially or completely dissolved form.
• organic solvents such, for example, as ethyl alcohol, acetone or dimethylformamide
• inorganic solvents such, for example, as water
• dyeing in an aqueous dye bath is primarily desirable.
• Dyestuffs containing at least one of the claimed acid groups excel, as tests have shown, in their particularly high afiinity to aluminium oxide layers. Such dyestuffs have hitherto not been used for dyeing aluminium oxide layers.
• This dyeing process causes an increase of foreign ions which cannot be avoided in practice, for example by salts which are always present in the commercial dyestuifs, by salts resulting from the oxidation process and adhering to the aluminium articles, or by compounds used to adjust the pH value of the dye bath.
• Salts which are always present in the commercial dyestuifs
• salts resulting from the oxidation process and adhering to the aluminium articles or by compounds used to adjust the pH value of the dye bath.
• Practice has shown that the presence of such salts can impede the drawing capacity (affinity) of dyestuffs so greatly that a complete renewal of the dye bath becomes necessary even if the original dyestutf concentration is still present.
• dyestuffs containing at least one acid group of a pentavalent element of Group V of the Periodic System with an ordinal index between 14 and 52 do not have this considerable, uneconomical disadvantage, but can be used dissolved in both hard water and water enriched with th usual salts. It was even noticed that the drawing capacity (affinity) of dyestuff solutions can, in certain cases, even be increased in the presence or upon the addition of certain salts.
• Aluminium articles provided with an aluminium oxide layer which have been dyed according to the process claimed, do not bleed when kept in water and upon sealing of the oxide layer. The bleeding was hitherto often not avoidable, even when taking all precautionary measures, whereby the production of uniform dyeings was rendered diiiicult.
• the drawing capacity (allinity) of dyestuffs containing at least one of the above defined acid groups on aluminiurn oxide is further, contrary to most of the hitherto used dyestuffs, barely influenced by a pH value of the dyebath in the conventional range of 43. The often complicated adjustment and maintenace of a constant pH value of the dye bath is thus no longer necessary.
• Aluminium oxide layers are usually dyed at temperatures between 55 and 65 C. since, when dyeing at room temperature, dyeings are generally obtained which are weaker or which bleed more strongly in water; Dyestuifs containing at least one of the above defined acid groups may, however, also be applied without disadvantage at room temperature.
• Dyestuffs containing at least one of the above defined acid groups when added in small concentrations to the sealing bath, further prevent the formation of oxide layers which can be rubbed off [Process according to F. Modic, Aluminium 35, 382 (1959) and 36, 457 (1960)].
• Acid groups of a pentavalent element of Group V of the Periodic System with an ordinal index between 14 and 52 are, e.g., the primary and secondary phosphonic, arsonic, stibonic, thiophosphonic, thioarsonic acids and monoesters thereof;
• primary groups of the formula AO(OH) and by secondary groups of the formula AO(OH) are to be understood, whereby A means P, As or Sb.
• R means an aliphatic or aromatic radical, preferably a hydroxy, alkyl, O-alkyl-, aryl or O-aryl radical
• thio compounds are such compounds to be understood, the O atoms of which are partially or entirely replaced by S atoms.
• the primary arsonic and stibonic acid groups are particularly suitable, and more particularly the primary phosphonic acid group. These groups may be linked, for example by an S, O or N atom to the dyestutf molecule. The link to a C atom is, however, particularly suitable.
• Various ones of the above mentioned acid groups may also be linked to the same dyestulf molecule,
• dyestulf classes are therefore suitable such, for example, as nitro, triarylmethane, xanthene, acridine,
• Dyestuffs are further suitable which contain a complex-forming group, for-example an o oxyc'arboxyphenyl or an ozo-dioxyazo group, or a complexbound heavy metal.
• dyeing in aqueous solution is of technical'impor tance
• those dyestuffs are primarily of interestwhich con tain inaddition to the above-defined acid groups,'other water-solubilizing groups, in particular'sulphonic acid groups, to increase the water-solubility.
• Dyestuffs which are suitable for the pr'ocess claimed are 7 only known from literature in a small number. They may beprepared, however, bymethods known per se. They may be constructed, for instance,.by starting from intermediate products contining one of the above defined acid groups. The above defined'acid groups can, however, also be introduced into the dyestufi molecule. A particularly of aluminium is completely decoloured in the sealing bath as a result of bleeding.
• the dyestulf used in this example may be prepared as follows: 17.3 parts of 3-.aminobenzene-l-phosphonic acid are dissolved neutral in 200 parts of Water with sodium hydroxide solution. 25 parts by volume of hydrochloric acid (33% )are added and the solution is'diazotized after having been cooled to 5.l by the dropwise addition of an aqueous solution of 7.0parts of sodium'nitrite.
• diazo solution is allowed to flow at 38 into a solution of 22.4 parts ,of 2-naphthol-6-sulphonic acid and 30 parts of sodium carbonate in; 350 parts of water. Upon completion, the solution is heated until the dyestuff dissolves,
• the precipisuitable process for producing the dyestufis used in accordance with the invention consists in reacting intermediate products or dyestufis containing a reactivehalo gen atom with aliphaticor aromaticiamino'or hydroxy compounds "containing one of the above defined necessary acid groups.
• compounds having a reactive halogen atom in addition to one of the above defined acid groups may also be reacted with intermediate products or dyestuffs containing amino and hydroxy 7 groups.”
• Azo dyestuffs maybe obtained, for instance, by
• azo components may be prepared, for example, in the benzene, naphthaline, vacylacetylamine, pyrazolonei and ;quinoline seriesgSo' far as the azo; dyestuff formed contains one or mQre omp e o up ey'm y' v by a known methods ,intothe heavy metal compounds.
• a degreased piece of aluminium is anodicallyoxidized in 20% sulphuric. acid at a current density of 1.5 amp/ dm. some minutes at 18-20 to form an oxide layer having a thickness of 10 microns, isrinsed in running Water for 15 minutes. and then dyed in a dyebath which dissolving .1 partofthe dyestufi of the tormulaf in 1000 parts of non-softened waten'at a pH"o f'7,.0 land at roomtemperature for 30 minutes..-;A' vivid golden yellow dyeing is obtained which does not.
• the dyestutf used in this example may be prepared as follows? 30 'parts of 1-amino-4-bromo-anthraquinone-2e sulphonic acid, 26 parts of 3-aminobenzene-l-phosphonic' acid, 47parts of sodiumcarbonate and 3 parts of copper (I)-chloride are heated-in 800 parts of water for 20 hours 7 By the addition of. hydrochloric acid until an acid reaction to Congo red is'obtained, the dyestulfis precipitatedand obtained pure by dissolving the sodium s'alt in 'water 'and'then precipitating the same. Dyestuff sof the following composition .0. I NH;
• EXAMPLE 3 A piece of aluminium anodically oxidized according to Example 1 is dyed for 30 minutes at 60 and a pH of 7.0 in a bath containing 2 parts of the dyestuif of the formula .1 wherein CPC means a copper phthalocyanine molecule substituted in 3:3:3":3"-position, 100 parts of sodium chloride and 1 part of nitrilo-triacetic acid in 1000 parts of non-softened water. A vivid, turquoise blue dyeing is obtained. If the piece of aluminum is placed in nonsoftened Water Without sealing, no bleeding can be noted even after three days.
• the dyeing is performed under the same conditions but in a bath containing 2 parts of copper phthalocyanine- 3:3:3":3-tetra-sulphonic acid, aluminium is not coloured.
• the dyeing is eilected under conditions suitable for dyestuffs exempt of phosphonic acid groups (i.e. at a pH of 5 and in the presence of softened water), a turquoise blue dyeing is also obtained. After being placed in non-softened Water, the piece of aluminium dyed in this manner is after one day partially and after three days completely decoloured.
• the dyestuif used in this example can be prepared as follows: 29 parts of copper phthalocyanine are introduced into 220 parts of chlorosulphonic acid at 35 and stirred for 1 hour at 35 and for 4 hours at 135. After having cooled to room temperature, one pours onto ice, the precipitated copper phthalocyanine-3:3:3":3"-tetrasulphonic chloride is filtered off, slurried in ice Water and neutralized with sodium carbonate. An aqueous solution of 11.5 parts of aminornethane phosphonic acid and 35 parts of sodium carbonate are added and the mixture is stirred until the reaction is completed. The dyestuff is precipitated by the addition of hydrochloric acid and is recrystallized from water.
• the dyestuff used in this example may be prepared as follows:
• the solution is neutralized With 80% acetic acid, 25 parts of crystallized copper sulphate are added, the whole is refluxed for 1 hour and the copper compound of the monoazo dyestuif is separated oh by filtration after the addition of sodium chloride.
• the paste is printed on anodically oxidized aluminium by the film screen printing process and dried in the air.
• the print is completed by sealing in boiling Water and purifying with benzene. An orange coloured print is obtained.
• the dyestuif used in this example is obtained by coupling diazotized 4-aminobenzene arsonic acid and Z-naphthol.
• the dyestuffs used in this example may also be dyed cold on aluminium from a 1% solution in dimethylforrnamide.
• the dyestufl. used in this example can l e prepared as follows 25.6 parts of 3-nitro-4-chlorobenzene-l sulphonic chloride are introduced at 3040 in portions into a solu tion of 12.5 'parts of 2-aminoethane phosphonic acid in 100 parts of water; A pH value of 7-8 is maintained duringthe' said introduction by the dropwise addition of 2N sodium carbonate solution. After the reaction is completed, the solution is rendered markedly acid to Congo red with hydrochloric acid, the precipitated product is filtered off and recrystallized from alcohol. 7
• the cooled solution of phenylhydrazine-El-phosphonic acid is rendered slightly alkaline by the dropwise addition of concentrated caustic soda lye, 13.8 parts of acetoacetic acid ethyl ester are, added at 60, the pH is adjusted to .12'with concentrated caustic soda lye after 1' hour and the solution isheated to -95-100 for 2 hours.
• phonic acid -1-arsonic acid or -1-stibonic acid maybe used with thesame success.
• the dyestuif used in this example may be prepared as follows: 15.5 parts 'of 4-aminonaphthalic acid 6-si1lphonic acid, 8.6 parts of 3 aminobe'nzene phosphonic acid and 30 parts of sodium bisulphite (anhydrous) are refluxed for 12'hou'rs in 200' parts of 'water. The dyestuff is isolated as usual. 7 r
• V EXAMPLE H I -Adegreased piece of aluminium isianodically oxidized in an oxalic acid solution consisting of 30 parts of oxalic acid, 20 parts of potassium oxalate and .1000 parts of water at a current densityof; 1.5 'amps./dm. 'and a temperature of 60 for 30 minutes to form an oxide lay'erf having a thickness of approximately :12 microns,
• the dyestufi used in this' examplel maybe prepared 'are' dissolved in 400 arser water at 60.
• a sheet of aluminium is anodically oxidized for 60 minutes ina solution consisting of 5 parts of chromic acid, 0.5 part of oxalic acid and 0.3 part of boric acid at 40 and with a current density of 1 amp/din. and a voltage of 25-40 volts, rinsed for 10 minutes in running water and thendyed at 60 'in a dyebath produced by dissolv ing 1 part of dyestufi of the formula in 1000 parts of water.”
• a matfred dyeing isobtained which, compared to the'dyeingproduced byz the come parable'dyestuff exempt of phosphonic acid groups, excels in its markedly improved water-fastness and its deeper shade.
• Theidyestufi used in this'example may be prepared as follows; 20.4; parts of the mono'jazo dyestuii prepared according to Example l'from diazot'ized' 3 -aminobenzene l-phosphonic acid and "2-naphthol-6-sulphonic acid i 13.8 parts of crystallizedcopper sulphate .and 15 parts of crystallized sodium acetate are then added. 14.1 parts of hy- 'drogen' peroxide (30%) dissolved in- 50 parts of water as follows: 17.3 parts of 3-aminobenzene-l-phosphonic :acid and 7' parts of sodium nitrite are dissolved neutral in 100 parts of water by the addition of sodium carbonate.
• This solution is added dropwise to a mixture of parts of ice and 12.5 parts of, concentrated sulphuric acid, and diazotized at 0-5
• the resulting .diazo solution is added at 10 to 80 parts by volume of sodium biare added dropwise within 30 minutes, the temperature is maintained at '60" for 2 hours, the solution is thenf tion of 1.3 parts of nitrilo-triacetic acid.
• a rc presents'a member selected from the group consisting of P, As and Sb. 7 i
• a process for'the dyeing of aluminum oxide layers on a metallic base material selected from the group consisting of aluminum and aluminum containing alloys which comprises contacting the said oxide layer with an, organic dyestufi which contains at least one'substltuent 7 group of the formula Table Continued Example Constitution of the dyestuff V Shade produced NH, II I 85 8031-1 7 Green.
• D represents the monovalent radical of an organic dyestufi selected from the group consisting of nitro, triarylmethane, xanthene, acridine, aminoketone, quinoline, anthraquinone, phthalocyanine, monoazo, disazo, polyazo, and azomethine dyestufis.
• organic dyestufi selected from the group consisting of nitro, triarylmethane, xanthene, acridine, aminoketone, quinoline, anthraquinone, phthalocyanine, monoazo, disazo, polyazo, and azomethine dyestufis.
• a metallic base material selected from the group consisting of aluminum and aluminum containing alloys having an aluminum oxide surface dyed with an organic dyestuff which contains at least one substituent group of the formula wherein A represents a member selected from the group consisting of P, As and Sb.
• a metallic base material selected from the group consisting of aluminum and aluminum containing alloys having an aluminum oxide surface dyed with an organic dyestutl which contains at lea-st one substituent group of the formula /OH DA O wherein A represents a member selected from the group consisting of P, As, and Sb, and D represents the monovalent radical of an organic dyestuif selected from the group consisting of nitro, triarylmethane, xanthene, acridine, aminoketone, quinoline, anthraquinone, phthalocyanine, monoazo, disazo, polyazo, and azomethine dyestuffs. 12.

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