JPS5819698B2 - Monoazoganryo no Seihou - Google Patents
Monoazoganryo no SeihouInfo
- Publication number
- JPS5819698B2 JPS5819698B2 JP49038085A JP3808574A JPS5819698B2 JP S5819698 B2 JPS5819698 B2 JP S5819698B2 JP 49038085 A JP49038085 A JP 49038085A JP 3808574 A JP3808574 A JP 3808574A JP S5819698 B2 JPS5819698 B2 JP S5819698B2
- Authority
- JP
- Japan
- Prior art keywords
- pigment
- water
- solution
- nitroaniline
- coupling
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
-
- 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
- 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
- C09B67/0001—Post-treatment of organic pigments or dyes
- C09B67/0014—Influencing the physical properties by treatment with a liquid, e.g. solvents
- C09B67/0015—Influencing the physical properties by treatment with a liquid, e.g. solvents of azoic pigments
-
- 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
- C09B29/32—Monoazo dyes prepared by diazotising and coupling from coupling components containing a reactive methylene group
- C09B29/33—Aceto- or benzoylacetylarylides
- C09B29/335—Aceto- or benzoylacetylarylides free of acid groups
- C09B29/338—Heterocyclic arylides, e.g. acetoacetylaminobenzimidazolone
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Coloring (AREA)
- Paints Or Removers (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Description
【発明の詳細な説明】
本発明の対象は下記式
なるモノアゾ顔料に関するものであり、該顔料はp−ニ
トロアニリンを公知の方法でジアゾ化し、5−アセトア
セチルアミノ−ベンツイミダシロンとカップリングさせ
ることによって製造される。DETAILED DESCRIPTION OF THE INVENTION The object of the present invention is a monoazo pigment of the following formula, which is prepared by diazotizing p-nitroaniline by a known method and coupling it with 5-acetoacetylamino-benzimidacylone. Manufactured by
更に又本発明は上記によって得られた粗顔料を水及び(
又は)有機溶剤の存在下に80〜180℃で熱処理する
ことにより上記の式で示される所望の形態のモノアゾ顔
料を製造する方法に関するものである。Furthermore, the present invention uses the crude pigment obtained above in water and (
or) It relates to a method for producing a monoazo pigment in the desired form represented by the above formula by heat treatment at 80 to 180°C in the presence of an organic solvent.
この顔料の製造はジアゾ化合物の溶液を、弱酸性媒体中
で微分散液の形で存在しているカップリング成分とカッ
プリングさせるか或はカップリング成分のアルカリ性溶
液を、予め用意したナトリウムアセテートを添加するこ
とによってpH−値を5〜6となしたジアゾ成分の溶液
に流入させるようにして実施することができる。The pigment can be produced by coupling a solution of the diazo compound with a coupling component which is present in the form of a fine dispersion in a weakly acidic medium, or by coupling an alkaline solution of the coupling component with a previously prepared solution of sodium acetate. This can be carried out by flowing into a solution of the diazo component which has been added to a pH value of 5 to 6.
カップリングを実施するためのその他の可能性は、ジア
ゾ成分及びカップリング成分の溶液を一緒にナトリウム
アセテート−酢酸−緩衝混合物に流入させることである
。Another possibility for carrying out the coupling is to flow the solutions of the diazo component and the coupling component together into a sodium acetate-acetic acid buffer mixture.
これら全ての操作方法の場合、陽イオン性、陰イオン性
又は非イオン性の表面活性化合物の存在下に操作するこ
とが好ましい。In all these operating methods, it is preferred to operate in the presence of cationic, anionic or nonionic surface-active compounds.
粒子柔軟性、着色力、被覆力及びラッカー及び合成樹脂
における加工性に関して最適な顔料形をつくるためには
、得られた顔料を本発明により、熱的後処理に付さなけ
ればならない。In order to create a pigment form that is optimal with respect to particle flexibility, tinctorial strength, covering power and processability in lacquers and synthetic resins, the pigments obtained must be subjected to a thermal aftertreatment according to the invention.
その際水性顔料懸濁液を水中で80〜150℃の温度で
即ち場合により加圧下で或は有機溶剤、例えばアルコー
ル類、低級カルボン酸類、カルボン酸アルキルエステル
類、芳香族類、塩素化された芳香族炭化水素類、不活性
溶剤、例えばジメチルホルムアミド、ジメチルスルフオ
キシド、ピリジンの存在下で80〜180℃の温度で処
理することができる。The aqueous pigment suspension is prepared in water at a temperature of 80 DEG to 150 DEG C., optionally under pressure, or in organic solvents, such as alcohols, lower carboxylic acids, carboxylic acid alkyl esters, aromatics, chlorinated The treatment can be carried out in the presence of aromatic hydrocarbons, inert solvents such as dimethylformamide, dimethylsulfoxide, pyridine at temperatures from 80 to 180°C.
上述の有機溶剤は純粋な形でも又は相互の混合物として
も乾燥した未処理の顔料に作用させることができる。The above-mentioned organic solvents can be applied to the dry, untreated pigment in pure form or as a mixture with one another.
本発明によるアゾ顔料は溶融範囲323乃至328℃を
有しそして橙色の粉末であり、これは普通の溶剤には全
く不溶である。The azo pigment according to the invention has a melting range of 323 DEG to 328 DEG C. and is an orange powder, which is completely insoluble in common solvents.
該顔料は着色力、輝しい色調、憂れた被覆力、並びに特
に良好な耐光性及び耐候性で優れている。The pigments are distinguished by their tinting strength, brilliant shade, good covering power and particularly good light and weather resistance.
この場合該顔料は、同じカップリング成分を用いて製造
されているが、ジアゾ成分としてはp−ニトロアニリン
に最モ近似している化合物を含んでいる最も比較しうる
アゾ顔料よりすぐれている。In this case, the pigment is superior to most comparable azo pigments, which are prepared using the same coupling component, but which, as a diazo component, contain a compound that most closely resembles p-nitroaniline.
このように本発明による顔料は3−ニトロアニリン、2
,4−ジニトロアニリン、4−クロルアニリン、4−メ
チルアニリン又は4−メトキシアニリンをジアゾ成分と
して含む対応する顔料よりも耐光性及び耐候性の点で優
れている。The pigment according to the invention thus contains 3-nitroaniline, 2
, 4-dinitroaniline, 4-chloroaniline, 4-methylaniline or 4-methoxyaniline as a diazo component in terms of light resistance and weather resistance.
又本発明による顔料は耐光性及び耐候性の点で2−クロ
ルアニリン、2−メチルアニリン又は2−メトキシアニ
リンをジアゾ成分として含むドイツ特許第122758
5号明細書に記載されているアゾ顔料より憂れており、
又被覆力及び色調の光沢の点では2−ニトロアニリンを
ジアゾ成分として含むアブ顔料より優れている。Further, the pigment according to the present invention contains 2-chloroaniline, 2-methylaniline or 2-methoxyaniline as a diazo component in terms of light resistance and weather resistance, as described in German Patent No. 122758.
This is more worrying than the azo pigment described in Specification No. 5,
In terms of covering power and color gloss, it is superior to an ab pigment containing 2-nitroaniline as a diazo component.
本発明による新規アゾ顔料は極めて種々の顔料用途に使
用できる。The novel azo pigments according to the invention can be used in a very wide variety of pigment applications.
例えば印刷インキの製造のために又はラッカー塗料及び
分散塗料を調製するために、又はゴム、人造物質、天然
及び合成の樹脂を着色するために使用することができる
。They can be used, for example, for the production of printing inks or for preparing lacquers and dispersion paints, or for coloring rubber, man-made substances, natural and synthetic resins.
該顔料は更に基体、特に織物繊維上に、並びにその他の
平面状成形物、例えば紙上に顔料捺染するのに好適であ
る。The pigments are furthermore suitable for pigment printing onto substrates, in particular textile fibers, and also onto other planar shapes, such as paper.
該顔料はその他の使用目的、例えばビスコースレーヨン
、又はセルロース−エーテル又は−エステル、ポリオレ
フィン類、ポリアミド類、ポリウレタン類、ポリグリコ
ールテレフタレート又はポリアクリルニトリルを紡止溶
液の状態で染色するために或は紙を着色するためにも使
用することができる。The pigments may be used for other purposes, for example for dyeing viscose rayon, or cellulose-ethers or -esters, polyolefins, polyamides, polyurethanes, polyglycol terephthalates or polyacrylonitrile in the spinning solution; It can also be used to color paper.
例1
p−ニトロアニリン13.8 g(0,1モル)を5N
塩酸80m1中で攪拌する。Example 1 13.8 g (0.1 mol) of p-nitroaniline was added to 5N
Stir in 80 ml of hydrochloric acid.
これを氷を用いて0〜5℃に冷やし、ついで5N亜硝酸
すl−IJウム20rI′Llを表面下に流すことによ
ってジアゾ化する。This is cooled to 0-5 DEG C. using ice and then diazotized by flowing 20 rI'Ll of 5N sodium nitrite under the surface.
次いでケイソウ土を加え、10分攪拌し次いで涙過する
。Then add diatomaceous earth, stir for 10 minutes and strain.
他方5−アセトアセチルアミノベンツイミダシロン(3
5%)70.9を水200’ ml、及び33係苛性ソ
一ダ溶液25m、l中に22℃で溶解し、次いで骨炭を
用いて澄明にする。On the other hand, 5-acetoacetylaminobenzimidacylone (3
5%) 70.9 is dissolved in 200 ml of water and 25 ml of 33% caustic soda solution at 22°C and then clarified using bone char.
水500rrLl、リン酸25g、33%苛性ソーダ溶
液30rul及びステアリルアルコールオキシエチレー
ト(20単位のエチレンオキシドを含む)の10係水性
溶液10wLlから成る混合物を緩衝液として先づ仕込
む。A mixture consisting of 500 rrLl of water, 25g of phosphoric acid, 30rl of 33% caustic soda solution and 10wLl of a 10% aqueous solution of stearyl alcohol oxyethylate (containing 20 units of ethylene oxide) is initially charged as a buffer.
ついで22℃でジアゾ溶液及びカップリング成分の溶液
を同時に緩衝液に流入する。The diazo solution and the coupling component solution are then simultaneously introduced into the buffer at 22°C.
これを95℃に加熱し、1時間この温度で攪拌を続け、
次いで吸引瀘過し、洗浄する。Heat this to 95°C and continue stirring at this temperature for 1 hour.
Then, it is suction filtered and washed.
湿った圧搾ケーキ150gをインブタノール140g及
び水200m1と攪拌し、そして密閉溶器中で1/2〜
1時間125℃で保持する。150 g of moist pressed cake is stirred with 140 g of inbutanol and 200 ml of water and 1/2 to
Hold at 125°C for 1 hour.
水蒸気でインブタノールを除去し、残留物を涙取すると
、乾燥後、憂れた耐光性及び耐候性、高い被覆力、並び
に焼付はラッカーにおける良好な流展性及び高い光沢を
有する橙赤色の顔料が得られる。Removing the inbutanol with water vapor and wiping off the residue produces an orange-red pigment with poor light and weather resistance, high covering power, and baking properties, good flowability and high gloss in lacquers. is obtained.
例2
p−ニトロアニリン27.6g(0,2モル)を例1の
記載に従ってジアゾ化する。Example 2 27.6 g (0.2 mol) of p-nitroaniline are diazotized as described in Example 1.
ジアゾ溶液及びアゾ成分を同時に下記の組成のNa−ア
セテート/氷酢酸−緩衝液に流入する。The diazo solution and the azo component are simultaneously introduced into a Na-acetate/glacial acetic acid buffer with the following composition.
この組成とは水10100O、ナトリウムアセテート8
2.9、氷酢酸20m1及び20単位のエチレンオキシ
ドを含むステアリルアルコールオキシエチレートの10
係水性溶液10m1から成る。This composition is 10,100 O of water, 8 O of sodium acetate.
2.9, 10 of stearyl alcohol oxyethylate containing 20 ml of glacial acetic acid and 20 units of ethylene oxide
Consisting of 10 ml of hydrophobic solution.
この混合物を95℃に加熱し、そして1時間この温度で
保持し、次いで吸引p過し、そして水洗する。The mixture is heated to 95° C. and kept at this temperature for 1 hour, then filtered with suction and washed with water.
約25係の顔料を含有する湿った圧搾ケーキを例1の記
載に従ってインブタノールを用いて仕上げる。A wet press cake containing approximately 25 parts of pigment is worked up using imbutanol as described in Example 1.
この混合物を水蒸気蒸留に付し、そして乾燥した後側1
に記載されている特性を有する橙赤色の顔料が得られる
。This mixture was subjected to steam distillation and the dried backside 1
An orange-red pigment is obtained having the properties described in .
例3
p−ニトロアニリン13.8gをジアゾ化し、そして水
200TLl中の5−アセトアセチルアミノベンツイミ
ダシロン24g及び33係の苛性ソーダ溶液24m1か
ら成る溶液とカップリングする。Example 3 13.8 g of p-nitroaniline are diazotized and coupled with a solution consisting of 24 g of 5-acetoacetylaminobenzimidacylon and 24 ml of 33% caustic soda solution in 200 TL of water.
この場合両者の溶液を約20℃で水500m1、ナトリ
ウムアセテート40g、氷酢酸10TLl、及びステア
リルアルコールから出発してこれをエチレンオキシド2
0モルと反応させることによって得られた乳化剤の10
%水性溶液10TfLlから成る緩衝液中に流入せしめ
る。In this case, both solutions are prepared at about 20° C. starting from 500 ml of water, 40 g of sodium acetate, 10 TL of glacial acetic acid, and stearyl alcohol, and mixed with 2 ml of ethylene oxide.
10 of the emulsifier obtained by reacting with 0 mol
% aqueous solution in a buffer consisting of 10 TfLl.
1時間攪拌を続け、95℃に加熱し、この温度で1時間
保持し、ついで吸引涙過する。Stirring is continued for 1 hour, heated to 95°C, held at this temperature for 1 hour, and then filtered with suction.
湿った圧搾ケーキ125gを水200wLlを添加しな
がら加圧下で1//2〜1時間125℃に加熱し、吸引
濾過し、水洗する。125 g of moist pressed cake are heated under pressure to 125 DEG C. for 1/2 to 1 hour while adding 200 wLl of water, filtered with suction and washed with water.
乾燥後非常に良好な堅牢特性を有する橙赤色の顔料が得
られる。After drying, an orange-red pigment with very good fastness properties is obtained.
例4
例3に記載の如くして得られた圧搾ケーキ(約20係)
125.!i1’をO−ジクロルペンゾール96g及び
水100m1と攪拌し、そして125℃で密閉容器中で
1時間加熱する。Example 4 Pressed cake obtained as described in Example 3 (approximately 20 cakes)
125. ! i1' is stirred with 96 g of O-dichloropenzole and 100 ml of water and heated at 125 DEG C. in a closed container for 1 hour.
次いで水蒸気を吹き込むことによって顔料エマルジョン
かう0−シ/70ルベンゾールを除く。The 0-C/70 rubenzole is then removed from the pigment emulsion by blowing in steam.
ついで濾過し、洗浄しそして乾燥した後側1に記載され
ているのと同様の特性を有する橙赤色の顔料が得られる
。After subsequent filtration, washing and drying, an orange-red pigment having properties similar to those described under 1 is obtained.
図面は、本発明により得られる顔料の赤外スペクトルを
示したものである。The drawing shows the infrared spectrum of the pigment obtained according to the invention.
Claims (1)
セチルアミノベンツイミダシロンとカップリングさせる
ことを特徴とする、次式 で示されるモノアル顔料の製法。 2 ジアゾ化されたp−ニトロアニリンを5−アセトア
セチルアミノベンツイミダシロンとカップリングさせ、
ついでカップリング生成物を水及び(又は)有機溶剤の
存在下に80〜180℃で熱的後処理に付することを特
徴とする特許請求の範囲第1項に記載の式で示されるモ
ノアゾ顔料の製法。[Scope of Claims] 1. A method for producing a monoal pigment represented by the following formula, which comprises coupling diazotized P-nitroaniline with 5-acetoacetylaminobenzimidacylon. 2. Coupling diazotized p-nitroaniline with 5-acetoacetylaminobenzimidacylone,
A monoazo pigment of the formula according to claim 1, characterized in that the coupling product is then subjected to a thermal after-treatment at 80 to 180°C in the presence of water and/or an organic solvent. manufacturing method.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE2317532A DE2317532C2 (en) | 1973-04-07 | 1973-04-07 | Monoazoplgment, process for its manufacture and its use |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS49130923A JPS49130923A (en) | 1974-12-16 |
JPS5819698B2 true JPS5819698B2 (en) | 1983-04-19 |
Family
ID=5877326
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP49038085A Expired JPS5819698B2 (en) | 1973-04-07 | 1974-04-05 | Monoazoganryo no Seihou |
Country Status (13)
Country | Link |
---|---|
JP (1) | JPS5819698B2 (en) |
BE (1) | BE813431A (en) |
BR (1) | BR7402714D0 (en) |
CA (1) | CA1027939A (en) |
CH (1) | CH590321A5 (en) |
DE (1) | DE2317532C2 (en) |
DK (1) | DK134116C (en) |
ES (1) | ES424847A1 (en) |
FR (1) | FR2224524B1 (en) |
GB (1) | GB1456540A (en) |
IN (1) | IN140449B (en) |
IT (1) | IT1010908B (en) |
NL (1) | NL172964C (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS6391400U (en) * | 1986-12-03 | 1988-06-13 |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3412731A1 (en) * | 1984-04-05 | 1985-10-17 | Hoechst Ag, 6230 Frankfurt | AMINOAZO COMPOUNDS, METHOD FOR THEIR PRODUCTION AND THEIR USE |
-
1973
- 1973-04-07 DE DE2317532A patent/DE2317532C2/en not_active Expired
-
1974
- 1974-03-27 IN IN681/CAL/1974A patent/IN140449B/en unknown
- 1974-04-02 NL NLAANVRAGE7404470,A patent/NL172964C/en not_active IP Right Cessation
- 1974-04-02 ES ES424847A patent/ES424847A1/en not_active Expired
- 1974-04-03 IT IT42642/74A patent/IT1010908B/en active
- 1974-04-03 CH CH463674A patent/CH590321A5/xx not_active IP Right Cessation
- 1974-04-05 JP JP49038085A patent/JPS5819698B2/en not_active Expired
- 1974-04-05 BR BR2714/74A patent/BR7402714D0/en unknown
- 1974-04-05 DK DK190374A patent/DK134116C/en not_active IP Right Cessation
- 1974-04-05 CA CA196,902A patent/CA1027939A/en not_active Expired
- 1974-04-05 GB GB1524974A patent/GB1456540A/en not_active Expired
- 1974-04-08 FR FR7412276A patent/FR2224524B1/fr not_active Expired
- 1974-04-08 BE BE142955A patent/BE813431A/en not_active IP Right Cessation
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS6391400U (en) * | 1986-12-03 | 1988-06-13 |
Also Published As
Publication number | Publication date |
---|---|
AU6756874A (en) | 1975-10-09 |
DK134116B (en) | 1976-09-13 |
BE813431A (en) | 1974-10-08 |
NL172964C (en) | 1983-11-16 |
NL7404470A (en) | 1974-10-09 |
CH590321A5 (en) | 1977-08-15 |
BR7402714D0 (en) | 1974-11-05 |
FR2224524B1 (en) | 1977-10-21 |
IT1010908B (en) | 1977-01-20 |
FR2224524A1 (en) | 1974-10-31 |
JPS49130923A (en) | 1974-12-16 |
ES424847A1 (en) | 1976-11-16 |
NL172964B (en) | 1983-06-16 |
DK134116C (en) | 1977-04-12 |
DE2317532C2 (en) | 1975-01-30 |
IN140449B (en) | 1976-11-13 |
GB1456540A (en) | 1976-11-24 |
CA1027939A (en) | 1978-03-14 |
DE2317532A1 (en) | 1974-06-06 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
TWI444436B (en) | Azo dyes for dyeing and printing hydrophobic materials | |
US4906735A (en) | Process for the manufacture of a monoazo acetoacetylaminobenzimidazolone | |
US4370269A (en) | Monoazo pigment derived from acetoacetylamino benzimidazolone | |
US4195020A (en) | Dichloro-phenyl-azo-acetoacetylamino-benzimidazolone pigments | |
EP0021332B1 (en) | Azo compounds process for their preparation, and use | |
US4504416A (en) | Azo compounds deriving from amino benzoic acid anilides and acetoacetylamino-benzimidazolone | |
JPS5819698B2 (en) | Monoazoganryo no Seihou | |
EP0025164B1 (en) | Disazo compounds, process for their preparation and use | |
US3118870A (en) | Water-insoluble monoazo-dyestuffs | |
CN102796399A (en) | Preparation method of high-color strength C. I. pigment yellow 154 | |
USRE25857E (en) | Water-insoluble benzeneazo-s-aceto- acetylaminobenzimidazolone dye- stuffs | |
JPS6120590B2 (en) | ||
US4287122A (en) | Monoazo compounds from 1-aminobenzene-2-carboxylic acid derivatives and their use as colorants | |
US4368155A (en) | Monoazo compounds derived from meta-amino-benzoic acid anilides and acetoacetylamino-benzimidazolone | |
US2069836A (en) | Monoazo dyestuffs and their production | |
CN114929809B (en) | Disperse azo dyes, process for their preparation and their use | |
US4005068A (en) | Disazo compounds from diphenylene sulfones and acetoacetylbenzimidazolones | |
JPH021862B2 (en) | ||
CA1143724A (en) | Azo compounds, their preparation and use | |
JPS5853024B2 (en) | Shinkimono Azoganriyouno Seihou | |
JPS6363593B2 (en) | ||
US2118088A (en) | Monoazo dyestuffs and their production | |
JPS6043383B2 (en) | Azo compounds and their production and usage | |
DE2328678C3 (en) | New disazo pigments, processes for their production and their uses | |
JPS597737B2 (en) | Production method of new disazo pigment |