CH638236A5 - Disazo pigments and use thereof - Google Patents
Disazo pigments and use thereof Download PDFInfo
- Publication number
- CH638236A5 CH638236A5 CH101181A CH101181A CH638236A5 CH 638236 A5 CH638236 A5 CH 638236A5 CH 101181 A CH101181 A CH 101181A CH 101181 A CH101181 A CH 101181A CH 638236 A5 CH638236 A5 CH 638236A5
- Authority
- CH
- Switzerland
- Prior art keywords
- formula
- hal
- alkyl
- disazo pigments
- parts
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- 239000000049 pigment Substances 0.000 title claims abstract description 35
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 125000005843 halogen group Chemical group 0.000 claims abstract description 10
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
- 238000004043 dyeing Methods 0.000 claims abstract description 3
- 239000002253 acid Substances 0.000 claims description 6
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 230000008878 coupling Effects 0.000 claims description 4
- 238000010168 coupling process Methods 0.000 claims description 4
- 238000005859 coupling reaction Methods 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 3
- 150000004985 diamines Chemical class 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 150000001805 chlorine compounds Chemical class 0.000 claims description 2
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- 150000008049 diazo compounds Chemical class 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 239000011368 organic material Substances 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 239000004753 textile Substances 0.000 claims description 2
- DGQLVPJVXFOQEV-JNVSTXMASA-N carminic acid Chemical compound OC1=C2C(=O)C=3C(C)=C(C(O)=O)C(O)=CC=3C(=O)C2=C(O)C(O)=C1[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O DGQLVPJVXFOQEV-JNVSTXMASA-N 0.000 abstract description 3
- 230000005012 migration Effects 0.000 abstract description 2
- 238000013508 migration Methods 0.000 abstract description 2
- 239000003973 paint Substances 0.000 abstract description 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 229920003023 plastic Polymers 0.000 abstract 1
- 239000004033 plastic Substances 0.000 abstract 1
- 229920002994 synthetic fiber Polymers 0.000 abstract 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 229940044174 4-phenylenediamine Drugs 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 229920000915 polyvinyl chloride Polymers 0.000 description 4
- 239000004800 polyvinyl chloride Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- -1 1-amino-2-methoxybenzene-5-carboxylic acid-y-chloro-n-propyl ester 1-amino-2-methoxybenzene-5-carboxylic acid - chloro-n-butyl ester Chemical compound 0.000 description 3
- FDGAEAYZQQCBRN-UHFFFAOYSA-N 3-amino-4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1N FDGAEAYZQQCBRN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
- 235000012730 carminic acid Nutrition 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 238000000227 grinding Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000004408 titanium dioxide Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 229920000877 Melamine resin Polymers 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000012320 chlorinating reagent Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000001054 red pigment Substances 0.000 description 2
- 239000002966 varnish Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- BWAPJIHJXDYDPW-UHFFFAOYSA-N 2,5-dimethyl-p-phenylenediamine Chemical compound CC1=CC(N)=C(C)C=C1N BWAPJIHJXDYDPW-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- AWFYPPSBLUWMFQ-UHFFFAOYSA-N 2-[5-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,3,4-oxadiazol-2-yl]-1-(1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1=NN=C(O1)CC(=O)N1CC2=C(CC1)NN=C2 AWFYPPSBLUWMFQ-UHFFFAOYSA-N 0.000 description 1
- OBCSAIDCZQSFQH-UHFFFAOYSA-N 2-methyl-1,4-phenylenediamine Chemical compound CC1=CC(N)=CC=C1N OBCSAIDCZQSFQH-UHFFFAOYSA-N 0.000 description 1
- BTXXTMOWISPQSJ-UHFFFAOYSA-N 4,4,4-trifluorobutan-2-one Chemical class CC(=O)CC(F)(F)F BTXXTMOWISPQSJ-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 239000004604 Blowing Agent Substances 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000004640 Melamine resin Substances 0.000 description 1
- 235000006679 Mentha X verticillata Nutrition 0.000 description 1
- 235000002899 Mentha suaveolens Nutrition 0.000 description 1
- 235000001636 Mentha x rotundifolia Nutrition 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 230000000485 pigmenting effect Effects 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical class [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/22—Compounds containing nitrogen bound to another nitrogen atom
- C08K5/23—Azo-compounds
- C08K5/235—Diazo and polyazo compounds
-
- C—CHEMISTRY; METALLURGY
- 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/10—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group
- C09B29/18—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group ortho-Hydroxy carbonamides
- C09B29/20—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group ortho-Hydroxy carbonamides of the naphthalene series
-
- C—CHEMISTRY; METALLURGY
- 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
- C09B33/153—Disazo dyes in which the coupling component is a bis-(aceto-acetyl amide) or a bis-(benzoyl-acetylamide)
-
- C—CHEMISTRY; METALLURGY
- 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
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/32—Preparation of azo dyes from other azo compounds by reacting carboxylic or sulfonic groups, or derivatives thereof, with amines; by reacting keto-groups with amines
- C09B43/38—Preparation of azo dyes from other azo compounds by reacting carboxylic or sulfonic groups, or derivatives thereof, with amines; by reacting keto-groups with amines by reacting two or more ortho-hydroxy naphthoic acid dyes with polyamines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Disazo pigments conform to the formula <IMAGE> where R is alkyl of 2-6 carbon atoms, Hal is a halogen atom, n is 1 or 2, X and Y are each hydrogen or halogen atoms or alkyl or alkoxy groups of 1-4 carbon atoms. Incorporated into plastics, paints and synthetic fibres, they produce carmine-red dyeings of good light, weather and migration fastness.
Description
**WARNUNG** Anfang DESC Feld konnte Ende CLMS uberlappen **.
PATENTANSPRÜCHE 1. Disazopigmente der Formel
EMI1.1
worin R eine Alkylgruppe mit 2-6 C, Hal ein Halogenatom, n = die Zahl 1 oder 2, X und Y H- oder Halogenatome, Alkyloder Alkoxygruppen mit 1-4 C bedeuten.
2. Disazopigmente gemäss Anspruch 1, worin -R-Hal die -Chloräthylgruppe bedeutet.
3. Disazopigmente gemäss Ansprüchen 1 und 2, worin X und Y Chloratome, Methyl- oder Methoxygruppen bedeuten.
4. Disazopigmente gemäss Ansprüchen 1 und 2, worin X und Y Methylgruppen bedeuten.
5. Verfahren zum Färben von hochmolekularem organischem Material ausserhalb der Textilindustrie, gekennzeichnet durch die Verwendung der Pigmente gemäss Anspruch 1.
Die Erfindung betrifft Disazopigmente der Formel
EMI1.2
worin R eine Alkylgruppe mit 2-6 C, Hal ein Halogenatom, n = die Zahl 1 oder 2, X und Y H- oder Halogenatome, Alkyloder Alkoxygruppen mit 14 C bedeuten.
Der Alkylrest R kann beispielsweise eine Äthyl-, Propyl-, Isopropyl-, Butyl- oder Isobutylgruppe und Hal ein Fluor- oder Brom-, vorzugsweise aber ein Chloratom sein. Der Rest-R-Hal ist vorzugsweise eine Ch1oräthylgruppe.
Man erhält die Pigmente der Formel (I) vorzugsweise durch Kondensation eines Säurechlorides der Formel
EMI1.3
mit einem Diamin der Formel
EMI1.4
im Molverhältnis 2:1.
Die Säurechloride der Formel (II) erhält man durch Kuppeln der Diazoverbindung des Amins der Formel
EMI1.5
mit 2,3-Hydroxynaphtoesäure und Behandeln der erhaltenen Azofarbstoffcarbonsäure mit säurechlorierenden Mitteln, wie Phosphortrichlorid, Phosphoroxychlorid oder insbesondere Thionylchlorid.
Als Beispiele von Aminen der Formel (IV) seien genannt: 1 Amino-2-methoxybenzol-5-carbonsäure-(3-chloräthylester, l -Amino-2-methoxybenzol-5-carbonsäure-ss-chlor-n-propyl- ester, 1 -Amino-2-methoxybenzol-5-carbonsäure-y-chlor-n-propyl- ester 1 -Amino-2-methoxybenzol-5-carbonsäure--chlor-n-butyl- ester, l -Amino-2-methoxybenzol-5-carbonsäure-ss-ss-dichloräthyl- ester.
Diazotierung und Kupplung erfolgen auf übliche Weise in wässrigem Medium. Die Behandlung mit den säurechlorierenden Mitteln wird zweckmässig in indifferenten organischen Lösungsmitteln durchgeführt.
Als Beispiele von Diaminen der Formel (III) seien erwähnt: 1,4-Phenylendiamin 2-Chlor-i ,4-phenylendiamin 2-Methyl-1,4-phenylendiamin 2-Methoxy- 1 ,4-diphenylendiamin 2,5-Dichlor- 1 4-phenylendiamin 2,5-Dimethyl-1 ,4-phenylendiamin 2,5 -Dimethoxy-1 ,4-phenylendiamin 2,5-Diäthoxy-1,4-phenylendiamin 2,5 -Dipropoxy-1 ,4-phenylendiamin 2-Chlor-5-methyl-1 ,4-phenylendiamin 2-Chlor-5-methoxy-1 ,4-phenylendiamin 2-Methyl-5-methoxy- 1 ,4-phenylendiamin.
Die erfindungsgemässen Pigmente können in feinverteilter Form zum Pigmentieren von hochmolekularen Verbindungen verwendet werden.
Beispiel 1
128,6 Teile der Farbstoffcarbonsäure, die man durch Kuppeln von diazotiertem 1-Amino-2-methoxybenzol-5 carbonsäure-ss-chloräthylester mit 2,3-Hydroxynaphtoesäure erhält, werden in 100 Teilen o-Dichlorbenzol aufgeschlämmt.
Dann werden 12 Teile Thionylchlorid und 0,5 Teile Dimethylformamid zugegeben und das Gemisch 2 Stunden auf 110 "C erhitzt. Die Suspension wird abgekühlt und das ausgefallene reine Säurechlorid abfiltriert, mit Petroläther gewaschen und getrocknet.
89,5 Teile des so hergestellten Azocarbonsäurechlorids und 13,6 Teile 2,5-Dimethyl- 1,4-phenylendiamin werden in 600 Teilen o-Dichlorbenzol eingerührt und auf 140-145 erhitzt.
Bei dieser Temperatur wird die Reaktionsmasse während 16 Stunden gerührt. Dann wird die Suspension heiss abfiltriert und das erhaltene Produkt nacheinander mit warmem o-Dichlorbenzol, Methanol und Wasser gewaschen und getrocknet. Man erhält 89,5 Teile des roten, feinkristallinen Pigmentes der Formel I, das sich gut dispergieren lässt.
Beispiel 2
68 g Polyvinylchlorid-Pulver (Suspensionspolymerisat), 33 g Dioctylphthalat, 2 g Dibutylzinnlaurat, 0,3 g eines Stabilisators auf Phosphatbasis und 0,7 g des nach Beispiel 1 hergestellten Pigmentes werden vermischt und auf dem 1600 heissen Mischwalzwerk während 15 Minuten verarbeitet. Anschliessend wird auf dem Kalander eine Folie von 0,4 mm Dicke hergestellt.
Sie ist in einem reinen carminroten Farbton gefärbt. Die Färbung ist hitzebeständig, licht- und migrationsecht.
Beispiel 3
0,2 g des nach Beispiel 1 hergestellten Pigments, 1 g Titandioxyd (Rutil) und 100 g LD-Polyäthylengranulat werden in einer Trommel gemischt und das Gemisch anschliessend auf dem Mischwalzwerk bei 1300 verarbeitet. Die Masse wird heiss zu Platten verpresst oder in der Strangpresse verformt. Die Platten zeigen einen schönen braunen Farbton von guter Lichtechtheit.
Beispiel 4
0,1 g des nach Beispiel 1 hergestellten Pigmentes, 0,5 g Titandioxyd (Rutil) und 100 g Polypropylengranulat werden in einer Trommel gemischt und das Gemisch anschliessend auf dem Mischwalzwerk bei 1900 verarbeitet, bis eine homogen gefärbte Mischung vorliegt. Die Masse wird heiss zu Platten von 1 mm verpresst. Die Platten zeigen einen reinen carminroten Farbton von guter Lichtechtheit.
Beispiel 5
100 g stabilisiertes Polyvinylchlorid werden mit 1 g eines durch Salzknetung von 0,5 g Pigment mit 0,5 g eines Kopolymerisates aus 85 % Polyvinylchlorid und 15 % Polyvinylacetat erhaltenen Präparates gemischt und 6 Minuten bei 1900 gewalzt.
Das Walzgut wird manuell bewegt, bis eine gute Pigmentverteilung erzielt wird. Die Masse wird nun unter Druck bei 190-200 in der Form wieder abgekühlt. Die auf diese Weise in einem reinen carminroten Farbton eingefärbten Platten zeichnen sich durch eine hohe Wetterechtheit aus.
In der gleichen Weise können aufgehellte wetterechte rote Färbungen von Hart-PVC erzeugt werden, wenn der Ansatz bei gleichem oder reduziertem Buntpigmentanteil zusätzlich Titandioxyd zugefügt wird.
Beispiel 6
10 g Titandioxyd und 2 g des nach Beispiel 1 hergestellten Pigments werden mit 88 g einer Mischung von 26,4 g Kokosal kydharz, 24,0 g Melamin-Formaldehydharz (50% Festkörper gehalt), 8,8 g Äthylenglykolmonomethyläther und 28,8 g Xylol während 48 Stunden in einer Kugelmühle vermahlen.
Wird dieser Lack auf eine Aluminiumfolie gespritzt, 30 Minuten bei Raumtemperatur vorgetrocknet und dann während 30 Minuten bei 120 C eingebrannt, dann erhält man eine Carminlackierung, die sich bei guter Farbstärke durch eine sehr gute tSberlackier-, Licht- und Wetterechtheit auszeichnet.
Beispiel 7
4 Teile des fein verteilten Pigments gemäss Beispiel 1 werden in 20 Teilen Lösungsmittel der folgenden Zusammensetzung eingerührt: 50 Teile Solvesso (Gemisch aromatischer Koh lenstoffe), 15 Teile Butylacetat, 5 Teile Exkin II (Verlaufmittel auf Ketoximbasis), 25 Teile Methyl-Isobutylketon, 5 Teile Sili konöl (1% Solvesso 150).
Nachdem die vollständige Feinverteilung erreicht ist (je nach Art des Rührens in ca. 15-60 Minuten), werden die Bindemittel zugesetzt, nämlich 48,3 Teile Baycryl L 530 (Acrylharz) (51% in Xylol/Butanol 3:1) und 23,7 Teile MaprenalTTX (Melaminharz) (55 % in Butanol).
Nach kurzem Homogenisieren wird der Lack nach üblichen Methoden wie Spritzen und Tauchen oder speziell zur kontinuierlichen Beschichtung von Metallblechen im Coil-Coating Verfahren appliziert und eingebrannt (Einbrennen 30 Minuten, 130 0). Die erhaltenen carminroten Lackierungen zeichnen sich durch sehr guten Verlauf, hohen Glanz und ausgezeichnete Feinverteilung des Pigmentes, sowie durch ausgezeichnete Wetterechtheiten.
Beispiel 8
200 Teile des nach Beispiel 1 hergestellten Pigmentes werden in 1500 Teilen Wasser suspendiert. Diese Suspension wird mehrmals mittels einer Pumpe, die eine Förderleistung von 400 Teilen Pigmentsuspension pro Minute besitzt, durch eine schnelllaufende horizontale Rührwerkstengelmühle des Typs DYNO-Mill (Hersteller: W. Bachofen AG, Basel, Schweiz) gedrückt, deren Mahlbehälter ein Leervolumen von 600 Vol.-Teilen besitzt und dessen Rührwelle mit einer Umdrehungsge schwindigkeit von 3000 Minze l dreht. Dies entspricht einer Um- fangsgeschwindigkeit von 10 m/sec. an den Rührscheiben.
Die Mühle ist mit 500 Vol.-Teilen spezieller Mahlkörper beschickt, nämlich mit Styrocell F 454 . Dabei handelt es sich um 0,95-1,15 mm grosse, schäumbare Polystyrolkugeln (Hersteller: Shell Chemie, Carrington, England), die durch Suspensionspolymerisation hergestellt wurden und die in ihrem Innern als Treibmittel n-Pentan enthalten.
Nach Erreichen der gewünschten Kornfeinheit wird das Pigment auf übliche Weise durch Filtration, Waschen, Trocknen im Vakuumschrank bei 80 "C und Pulverisieren aufgearbeitet. Man erhält 195 Teile des feinkristallinen roten Pigmentes, das gegen über dem Ausgangspigment an Farbstärke, Transparenz und Reinheit zugenommen hat.
Beispiel9
In eine Lösung von 64 Teilen Dercinate 70/D (70%ges Na Salz einer hydrierten Abietinsäure, Hersteller: DRT, Dax, France) in 1500 Teilen Wasser werden 200 Teile des nach Beispiel 1 hergestellten Pigmentes unter Rühren eingetragen.
Durch Zugabe von verd. Salzsäure wird der pH-Wert auf 6 gesenkt.
Diese geflockte Pigmentsuspension wird mit Hilfe der in Beispiel 2 beschriebenen Mahlapparatur bis zur gewünschten Pigmentfeinheit gemahlen und anschliessend auf die ebenfalls beschriebene Weise isoliert.
Man erhält 235 Teile einer feinkristallinen roten Pigmentaufbereitung, die gegenüber dem Ausgangspigment deutlich an Farbstärke, Transparenz und Reinheit zugenommen hat und sich durch eine hervorragende Dispergierbarkeit auszeichnet.
** WARNING ** beginning of DESC field could overlap end of CLMS **.
PATENT CLAIMS 1. Disazo pigments of the formula
EMI1.1
wherein R is an alkyl group with 2-6 C, Hal is a halogen atom, n = the number 1 or 2, X and Y are H or halogen atoms, alkyl or alkoxy groups with 1-4 C.
2. disazo pigments according to claim 1, wherein -R-Hal is the -Chloräthylgruppe.
3. disazo pigments according to claims 1 and 2, wherein X and Y are chlorine atoms, methyl or methoxy groups.
4. disazo pigments according to claims 1 and 2, wherein X and Y are methyl groups.
5. A method for dyeing high molecular weight organic material outside the textile industry, characterized by the use of the pigments according to claim 1.
The invention relates to disazo pigments of the formula
EMI1.2
wherein R is an alkyl group with 2-6 C, Hal is a halogen atom, n = the number 1 or 2, X and Y are H or halogen atoms, alkyl or alkoxy groups with 14 C.
The alkyl radical R can be, for example, an ethyl, propyl, isopropyl, butyl or isobutyl group and Hal can be a fluorine or bromine atom, but preferably a chlorine atom. The radical R-Hal is preferably a chloroethyl group.
The pigments of the formula (I) are preferably obtained by condensation of an acid chloride of the formula
EMI1.3
with a diamine of the formula
EMI1.4
in a molar ratio of 2: 1.
The acid chlorides of the formula (II) are obtained by coupling the diazo compound of the amine of the formula
EMI1.5
with 2,3-hydroxynaphtoic acid and treating the azo dye carboxylic acid obtained with acid chlorinating agents such as phosphorus trichloride, phosphorus oxychloride or, in particular, thionyl chloride.
Examples of amines of the formula (IV) are: 1-amino-2-methoxybenzene-5-carboxylic acid (3-chloroethyl ester, 1-amino-2-methoxybenzene-5-carboxylic acid-ss-chloro-n-propyl ester), 1-amino-2-methoxybenzene-5-carboxylic acid-y-chloro-n-propyl ester 1-amino-2-methoxybenzene-5-carboxylic acid - chloro-n-butyl ester, l -amino-2-methoxybenzene- 5-carboxylic acid-SS-SS-dichloroethyl ester.
Diazotization and coupling take place in the usual way in an aqueous medium. The treatment with the acid chlorinating agents is expediently carried out in inert organic solvents.
Examples of diamines of the formula (III): 1,4-phenylenediamine 2-chloro-i, 4-phenylenediamine 2-methyl-1,4-phenylenediamine 2-methoxy-1,4-diphenylenediamine 2,5-dichloro- 1 4-phenylenediamine 2,5-dimethyl-1,4-phenylenediamine 2,5-dimethoxy-1,4-phenylenediamine 2,5-diethoxy-1,4-phenylenediamine 2,5-dipropoxy-1,4-phenylenediamine 2- Chloro-5-methyl-1,4-phenylene diamine 2-chloro-5-methoxy-1,4-phenylene diamine 2-methyl-5-methoxy-1,4-phenylene diamine.
The pigments according to the invention can be used in finely divided form for pigmenting high molecular weight compounds.
example 1
128.6 parts of the dye carboxylic acid obtained by coupling diazotized 1-amino-2-methoxybenzene-5-carboxylic acid ss-chloroethyl ester with 2,3-hydroxynaphtoic acid are slurried in 100 parts of o-dichlorobenzene.
Then 12 parts of thionyl chloride and 0.5 part of dimethylformamide are added and the mixture is heated for 2 hours to 110 ° C. The suspension is cooled and the pure acid chloride which has precipitated is filtered off, washed with petroleum ether and dried.
89.5 parts of the azocarboxylic acid chloride thus prepared and 13.6 parts of 2,5-dimethyl-1,4-phenylenediamine are stirred into 600 parts of o-dichlorobenzene and heated to 140-145.
At this temperature, the reaction mass is stirred for 16 hours. The suspension is then filtered off hot and the product obtained is washed in succession with warm o-dichlorobenzene, methanol and water and dried. This gives 89.5 parts of the red, finely crystalline pigment of the formula I, which is easy to disperse.
Example 2
68 g of polyvinyl chloride powder (suspension polymer), 33 g of dioctyl phthalate, 2 g of dibutyltin laurate, 0.3 g of a phosphate-based stabilizer and 0.7 g of the pigment prepared according to Example 1 are mixed and processed on the 1600 hot mixing mill for 15 minutes. A film with a thickness of 0.4 mm is then produced on the calender.
It is colored in a pure carmine color. The coloring is heat-resistant, light and migration-resistant.
Example 3
0.2 g of the pigment produced according to Example 1, 1 g of titanium dioxide (rutile) and 100 g of LD-polyethylene granulate are mixed in a drum and the mixture is then processed at 1300 on the mixing roller mill. The mass is hot pressed into sheets or shaped in the extrusion press. The plates show a beautiful brown color with good lightfastness.
Example 4
0.1 g of the pigment produced according to Example 1, 0.5 g of titanium dioxide (rutile) and 100 g of polypropylene granules are mixed in a drum and the mixture is then processed on the mixing roller mill at 1900 until a homogeneously colored mixture is obtained. The mass is hot pressed into sheets of 1 mm. The plates show a pure carmine color with good lightfastness.
Example 5
100 g of stabilized polyvinyl chloride are mixed with 1 g of a preparation obtained by salt-kneading 0.5 g of pigment with 0.5 g of a copolymer of 85% polyvinyl chloride and 15% polyvinyl acetate and rolled at 1900 for 6 minutes.
The rolling stock is moved manually until a good pigment distribution is achieved. The mass is then cooled again under pressure at 190-200 in the mold. The panels colored in this way in a pure carmine-red color are characterized by high weather fastness.
In the same way, lightened weather-resistant red colorations of rigid PVC can be produced if the mixture is additionally added with the same or reduced amount of colored pigment.
Example 6
10 g of titanium dioxide and 2 g of the pigment prepared according to Example 1 are mixed with 88 g of a mixture of 26.4 g of cocosal resin, 24.0 g of melamine-formaldehyde resin (50% solids content), 8.8 g of ethylene glycol monomethyl ether and 28.8 g Grind xylene in a ball mill for 48 hours.
If this varnish is sprayed onto an aluminum foil, pre-dried for 30 minutes at room temperature and then baked at 120 C for 30 minutes, a carmine varnish is obtained which, with good color strength, is characterized by very good fastness to paint, light and weather.
Example 7
4 parts of the finely divided pigment according to Example 1 are stirred into 20 parts of solvent of the following composition: 50 parts of Solvesso (mixture of aromatic carbons), 15 parts of butyl acetate, 5 parts of Exkin II (leveling agent based on ketoxime), 25 parts of methyl isobutyl ketone, 5 Parts of silicone oil (1% Solvesso 150).
After the complete fine distribution is reached (depending on the type of stirring in about 15-60 minutes), the binders are added, namely 48.3 parts Baycryl L 530 (acrylic resin) (51% in xylene / butanol 3: 1) and 23 , 7 parts MaprenalTTX (melamine resin) (55% in butanol).
After a brief homogenization, the lacquer is applied and baked using conventional methods such as spraying and dipping or especially for the continuous coating of metal sheets in the coil coating process (baking in 30 minutes, 130 °). The carmine red coatings obtained are characterized by a very good flow, high gloss and excellent fine distribution of the pigment, as well as excellent weather fastness.
Example 8
200 parts of the pigment prepared according to Example 1 are suspended in 1500 parts of water. This suspension is pressed several times by means of a pump, which has a delivery rate of 400 parts of pigment suspension per minute, through a high-speed horizontal agitator stalk mill of the DYNO-Mill type (manufacturer: W. Bachofen AG, Basel, Switzerland), the grinding container of which has an empty volume of 600 vol . Parts and the agitator shaft rotates at a speed of 3000 mint l. This corresponds to a peripheral speed of 10 m / sec. on the stirring discs.
The mill is loaded with 500 parts by volume of special grinding media, namely Styrocell F 454. These are 0.95-1.15 mm, foamable polystyrene balls (manufacturer: Shell Chemie, Carrington, England), which were produced by suspension polymerization and which contain n-pentane as a blowing agent inside.
After the desired particle size has been reached, the pigment is worked up in the customary manner by filtration, washing, drying in a vacuum cabinet at 80 ° C. and pulverizing. 195 parts of the finely crystalline red pigment are obtained, which have increased in strength, transparency and purity compared to the starting pigment.
Example 9
200 parts of the pigment prepared according to Example 1 are introduced into a solution of 64 parts of Dercinate 70 / D (70% saturated Na salt of a hydrogenated abietic acid, manufacturer: DRT, Dax, France) in 1500 parts of water with stirring.
The pH value is reduced to 6 by adding dilute hydrochloric acid.
This flocculated pigment suspension is ground to the desired pigment fineness using the grinding apparatus described in Example 2 and then isolated in the manner also described.
This gives 235 parts of a finely crystalline red pigment preparation, which has increased significantly in color strength, transparency and purity compared to the starting pigment and is distinguished by excellent dispersibility.
Claims (5)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH101181A CH638236A5 (en) | 1981-02-16 | 1981-02-16 | Disazo pigments and use thereof |
| IT19665/82A IT1157303B (en) | 1981-02-16 | 1982-02-15 | DISAZOIC PIGMENTS, PROCEDURE FOR THEIR PREPARATION AND USE |
| JP57023491A JPS57155257A (en) | 1981-02-16 | 1982-02-16 | Disazo pigment, manufacture and use |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH101181A CH638236A5 (en) | 1981-02-16 | 1981-02-16 | Disazo pigments and use thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH638236A5 true CH638236A5 (en) | 1983-09-15 |
Family
ID=4200359
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH101181A CH638236A5 (en) | 1981-02-16 | 1981-02-16 | Disazo pigments and use thereof |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JPS57155257A (en) |
| CH (1) | CH638236A5 (en) |
| IT (1) | IT1157303B (en) |
-
1981
- 1981-02-16 CH CH101181A patent/CH638236A5/en not_active IP Right Cessation
-
1982
- 1982-02-15 IT IT19665/82A patent/IT1157303B/en active
- 1982-02-16 JP JP57023491A patent/JPS57155257A/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| IT1157303B (en) | 1987-02-11 |
| JPS57155257A (en) | 1982-09-25 |
| IT8219665A0 (en) | 1982-02-15 |
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| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |