CS243584B1 - Azocondensing pigments and method of their production - Google Patents
Azocondensing pigments and method of their production Download PDFInfo
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- CS243584B1 CS243584B1 CS85482A CS48285A CS243584B1 CS 243584 B1 CS243584 B1 CS 243584B1 CS 85482 A CS85482 A CS 85482A CS 48285 A CS48285 A CS 48285A CS 243584 B1 CS243584 B1 CS 243584B1
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- pigments
- production
- formula
- hydroxy
- azocondensing
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- 239000000049 pigment Substances 0.000 title claims description 10
- 238000000034 method Methods 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- MWUCSURZWUDISB-UHFFFAOYSA-N 2-(4-aminophenyl)isoindole-1,3-dione Chemical compound C1=CC(N)=CC=C1N1C(=O)C2=CC=CC=C2C1=O MWUCSURZWUDISB-UHFFFAOYSA-N 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- -1 chloro, methyl Chemical group 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Chemical group 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 239000003973 paint Substances 0.000 description 3
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 2
- ALKYHXVLJMQRLQ-UHFFFAOYSA-N 3-Hydroxy-2-naphthoate Chemical compound C1=CC=C2C=C(O)C(C(=O)O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 229940117389 dichlorobenzene Drugs 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000001054 red pigment Substances 0.000 description 2
- BDQFCUOTSSWNDP-UHFFFAOYSA-N 4-[(2,5-dichlorophenyl)diazenyl]-3-hydroxynaphthalene-2-carbonyl chloride Chemical compound OC1=C(N=NC2=C(Cl)C=CC(Cl)=C2)C2=C(C=CC=C2)C=C1C(Cl)=O BDQFCUOTSSWNDP-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical class ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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- Indole Compounds (AREA)
- Paints Or Removers (AREA)
Description
(54) Azokondenzační pigmenty a způsob jejich výroby(54) Azocondensation pigments and process for their production
Vynález se týká azokondenzačních pigmentů na bázi kyseliny 3-hydroxy-2-naftoové a způsobu jejich výroby za použití N- (4-aminof enyl) f talimidu.The present invention relates to 3-hydroxy-2-naphthoic acid azocondensation pigments and a process for their preparation using N- (4-aminophenyl) phthalimide.
Při výrobě azokondenzačních pigmentů na bázi kyseliny 3-hydroxy-2-naítoové se obvykle vychází z chloridu kyseliny 4-arylazo-2-hydroxy-2-naftoové, který reaguje s různě substituovanými aromatickými aminy nebo diaminy. Tato kondénzační reakce se provádí v prostředí bezvodých organických inertních rozpouštědel. Rada azokondenzačních pigmentů je popsána např. v patentech NSR pat. č. 2 240 927, 2 204 253, 2 259 340, 2 431 728.The production of 3-hydroxy-2-naphthoic acid azocondensation pigments is usually based on 4-arylazo-2-hydroxy-2-naphthoic acid chloride, which reacts with variously substituted aromatic amines or diamines. This condensation reaction is carried out in an environment of anhydrous organic inert solvents. A number of azo condensation pigments are described, for example, in U.S. Pat. No. 2 240 927, 2 204 253, 2 259 340, 2 431 728.
Nyní bylo zjištěno, že nové pigmenty obecného vzorce IIt has now been found that the novel pigments of formula (I)
kdewhere
Rt a Rž značí vodík, chlor, methyl, trifluormethyl, alkoxyl s 1 až 3 atomy uhlíku, mají velmi dobré aplikační vlastnosti a lze je podle vynálezu vyrábět tak, že halogenid kyseliny 4-arylazo-3-hydroxy-2-naftoové obecného vzorce IIR 1 and R 2 denote hydrogen, chlorine, methyl, trifluoromethyl, C 1 -C 3 alkoxy, have very good application properties and can be prepared according to the invention such that the 4-arylazo-3-hydroxy-2-naphthoic acid halide of the formula II
kdewhere
Ri a Rž mají význam uvedený výše aR 1 and R 2 are as defined above and
X je chlor neba brom, se kondenzuje s N-(4-aminofenyl)ftalimidem v prostředí inertního organického rozpouštědla za teploty 105 až 170 °C.X is chlorine or bromine, condensed with N- (4-aminophenyl) phthalimide in an inert organic solvent at 105-170 ° C.
Jako organické inertní rozpouštědlo lze použít toluen, xylen, chlorbenzen, chlortolueny, dichlorbenzen, nitrobenzen atd. Kondenzaci je možno provádět za přídavku činidel neutralizujících uvolňovaný chlorovodík, což může být např. octan sodný, případně se reakční směs profukuje inertním plynem, nejčastěji dusíkem, nebo se kondenzace provede za sníženého tlaku.As an organic inert solvent, toluene, xylene, chlorobenzene, chlorotoluenes, dichlorobenzene, nitrobenzene, etc. can be used. condensation is performed under reduced pressure.
Pigmenty, získané postupem podle vynálezu, se vyznačují dobrou vydatností a stálostmi. Lze je a'plikovat především do nátěrových hmot (olejových barev, vypalovacích nátěrů atd.).The pigments obtained according to the invention are characterized by good spreading and stability properties. They can be applied primarily to paints (oil paints, baking paints, etc.).
V příkladech jsou ilustrativně ukázány pigmenty podle vynálezu a způsob jejich přípravy.The pigments according to the invention and the process for their preparation are illustrated by way of example.
Příklad 1Example 1
Do reakčního kotlíku, opatřeného míchadlem, zpětným chladičem, teploměrem a přívodem dusíku, bylo předloženo 510 g 1,2-dichlorbenzenu, 30 g chloridu kyseliny 4- (2,5-dichlorfenylazo )-3-hydroxy-2-naftoové a 17,9 g N-(4-aminofenyljftallmidu. Reakční směs byla za míchání a probublávání dusíkem, zahřívána na 145 °C po dobu 5 hodin. Produkt pak byl za horka zfiltrován, promyt horkým dichlorbenzenem, etanolem a nakonec vodou a usušen při 80 °C. Bylo získáno 37 g červeného pigmentu o tomto elementárním složení:510 g of 1,2-dichlorobenzene, 30 g of 4- (2,5-dichlorophenylazo) -3-hydroxy-2-naphthoic acid chloride and 17.9 g were charged to a reaction vessel equipped with a stirrer, reflux condenser, thermometer and nitrogen inlet. The mixture was stirred and bubbled with nitrogen, heated at 145 ° C for 5 hours, filtered hot, washed with hot dichlorobenzene, ethanol and finally with water and dried at 80 ° C. obtained 37 g of a red pigment with the following elemental composition:
63,77 % C (vypočteno 64,04 %)63.77% C (calculated 64.04%)
3,35 °/o H (vypočteno 3,12 °/o)3.35 ° / o H (calculated 3.12 ° / o)
9,92 % N (vypočteno 9,63 %JN, 9.92
12,87 o/o Cl (vypočteno 12,20 %)12.87 o / o Cl (calculated 12.20%)
Příklad 2Example 2
Obdobným způsobem jako v příkladu 1 byla provedena kondenzace N-(4-aminofenyljftalimidu se 4-fenylazo nebo 4-(2-chlorfenylazo)-, nebo 4-(2-chlor-5-metylfenylazo)-, nebo 4-(3-trifluormetylfenylazo)-, nebo 4-(2,5-dimetylfenylazo)-2-hydroxy-2-naftoylchloridem, přičemž byly získány červené pigmenty.In a similar manner to Example 1, condensation of N- (4-aminophenyl) phthalimide with 4-phenylazo or 4- (2-chlorophenylazo) -, or 4- (2-chloro-5-methylphenylazo) -, or 4- (3-trifluoromethylphenylazo) was carried out. or 4- (2,5-dimethylphenylazo) -2-hydroxy-2-naphthoyl chloride to give red pigments.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS85482A CS243584B1 (en) | 1985-01-24 | 1985-01-24 | Azocondensing pigments and method of their production |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS85482A CS243584B1 (en) | 1985-01-24 | 1985-01-24 | Azocondensing pigments and method of their production |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS48285A1 CS48285A1 (en) | 1985-09-17 |
| CS243584B1 true CS243584B1 (en) | 1986-06-12 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS85482A CS243584B1 (en) | 1985-01-24 | 1985-01-24 | Azocondensing pigments and method of their production |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS243584B1 (en) |
-
1985
- 1985-01-24 CS CS85482A patent/CS243584B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS48285A1 (en) | 1985-09-17 |
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