JPS5823857A - Improvement of disazo pigment useful technical properties - Google Patents

Abstract

(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

[Detailed description of the invention] Disazo pigment CI Pidamento-85 (V
-@I No. 211o8) has become popular as one of the most important organic yellow products in the field of paint and plastics.

However, the technical requirements for the utilization of a very high VH in the field of paints and plastics are also at hand, as compared to chemically pure disazotized materials. Due to lack of income, the health problems worsen and people are forced to go to work.

Obis-diazotization to acetoacetylainobenzene 44
'-Diainodiphere 1 Lure 4 Trouts O Disazo Pigment O Situated by O Cag Ring Also in Daio Prefecture - Law OS Society Formation III, Issimitsu Kame Disazo Pigment O Scene III Shikoku Solitary Friendship Agent - 1 Topcoat - and Transfer Triis
In the case of blood stains, the usual tortoise coupling method is blocked at the point where the reaction is ensured by collapsing and the bisdiazonium compound O coulometric reaction. As soon as possible, Koharu Sashi, who is afraid of coupling, will be killed. ζO
In the case of cuckoo, I got 4IL noodles by coupling 1 minute to the water value 1 and then boiling it again and then sinking it again to 141. as filtered. In order to improve the pigment quality and the pigment form with soft particles and good coloring power.
Coupling followed by pigment suspension tt1. wsb is performed. These quality changes JI & bisdiazonium m
- The wave and the coupling component of the aloda gas are put into the reactor at once, and the 4L company is tied when the 11mm is charged by the field meeting.

Motohata Akinen believes that even if he is a carpenter and manufactures Pigment Yellow 85 and chain-rimmed O disazo quince, this b is perfect for wealth.
We have found a simple method that allows a high preservative and a transfer agent to have a high purity and purity of 11% with high toughness and smearing properties.

The present invention has many advantages of disazo pigments! ＠Technology A method for improving the quality of the coupling: Adding ions to the resulting uniform to neutral aqueous pigment suspension, and heating it under a cloud. The present invention relates to the above method.

Honko Meikansha, below is a technique for using disazo pigments - a method for improving ag. The same or different positions consisting of yang@*rusen, X is water volume or salt 1/A porridge, and 1 member and n sister independently of each other means O or an integer from 1 to 6.K3111m Disazo structure @t)
mfll 懺乌时中性水性悬悬中中闭子lll! Heat the bat ion II and ML to low heat. We have discovered the above method which uses - as a metaphor.

For a minute and a half, I will be responsible for O and Fifty Seki, respectively.
jLsJ and island are in the 2-14-also 5-position with methyl, meth, or chlorine! Preferably h means a bulky atom of water, two chlorine atoms are present in the 2- and 5-positions, 2 chlorine atoms are present in the 1- and 4-positions, and (Pigment Yellow 85).

The sulfur Ilt double ion can be added in gaseous form as sulfur dioxide or in aqueous I6 liquid, or as the sulfur Ilt salt, the sulfur salt, or the disulfite salt. , blood sulfuric acid record sodium or -potassium,
Sodium sulfate or a-potassium is dried or stored and added in the II-form. The OWr requirement was determined by preliminary experiments and was approximately α5 to 10tI for the generated St family.
Preferably, the weight is 2 x 5 x.

The pigment suspension is prepared using a conventional method, for example, for several minutes to 50 to 1 hour.
00U01! Preferably fishing time to 2 hours 80
It takes a while to heat up to 100 CK. This heating can be done at a temperature of 1IR4ctooC or higher.
If necessary, it is possible to add a terminating agent, for example an organic agent, but in this case it is advantageous to increase the temperature only gradually.

Peng Post-Il German License Application Publication No. 2502509IK
If N is carried out, d1 is first mixed with water and water, then stirred in the presence of alkali 90, and then washed until neutral K. For Fim@, heat the mixture to a temperature of 100p or more from the admixture Lm%I%4i@ latent agent. This Arca 946 is the German l1lIWII＾ Application Notice No. 25.
It is also described in No. G2517.

The organic agent Oi is extracted from the aqueous suspension using the II method.
#- After washing, drying and grinding until the body is soft.

Particularly, the carpenter's roof patch Km and the method by Tomiaki Hon.
The product is 116% due to the quality and perfect 0'' Ik lacquer tone - 1 upper brittle - 1 transition - and the Niji Yoho Gyokurei.

Next, at 0 Km, the budding member - 1 part and the percentage O will be added to the weight.

even 1 4 s'-jitaru 44'-sia (fudiphenyl 51
6 parts by volume are stirred with 400 parts by volume and 25 G parts by volume of 51 salt, cooled with ice to about OC and bisdiazotized with 515 parts of 40 gji nitrate-sodium Asaba at 0 to 5C.

Thoroughly stir the clear IEKL & bisdiazonium salt 11 solution, and at 20 to 25C, precipitate the acetoacetate arylide from the alkaline wave to form the 1-acybenzene in 1-7-acetyl acetyl-2-methane 87@ The suspension value of the suspension wave is maintained at 4.5 to 5.

After the reaction of the bisdiazonium salt was completed, 5 parts of Natricium was added to the suspension wave, and 0 water vapor was introduced.
1 (Heat, keep at this temperature for 1 hour, then cool to 70℃, wash until salt free and dry.) sex 1
*Sweet.

Example 2 Example IKm"C arrangement is carried out, however, after completing the cup!
Add water and precipitate again to pH value [4-5]
IIi′:! I can do it. Similarly, a yellow pigment having good non-electrostatic properties of heavy phase and blur phase is obtained.

Example S (Comparative Example) The procedure was carried out as described in Example IK*, except that 9 um of sodium sulfite was added and one difference was made. The resulting pigment has a significantly reduced tenacity and smudging properties, especially in the case of the Carpenter's Convention batch.

Example 4 4s'-dichloro-44'-cya inodiphenyl 2S
, SgkA I XJIII Oll amount 11 AK
Stir, cool with ice O, and add 40a
mai 1 ml nato sori mu wave 2 melon 3 volume art to bisdiazotize 0 pieces 40011 volume art, slightly far *tmi
i*Haji ion is decomposed with 7 midosurunene and mRl
As m, o'*rt strangely soil distribution 0* sublayer filtration. The bisdiazonium salt obtained in 0.011 was thoroughly stirred for 1 hour at 10° C., and 1-Arethyl acetyl acetate 2.4-Dimethylbenzene was dispersed in Water-5.
0 to 1 alkaline solution containing 445 parts of coupling component in OO @ quantity room and ssg @ *soda fatigue 20 pieces
It was prepared by precipitation with 14 parts of glacial acetic acid at 0C and mixed with #1 and 21 parts. pH of suspended waves during coupling
- Values range from &5 to 450 by adding 0 drops of 6Xlf
Keep @-, 401g in pigment suspension wave after coupling
Add a portion of IL@@Hondakunato ν-fitO@, then heat to 98 CKJl, keep at room temperature for 50 minutes, cool the suspension to 70°C, and filter.

The reddish-yellow pigments applied after washing, tflk and grinding have a satisfactory O content in lacquers, even in the case of the carpentry process.

Example 5 2.2! '52.2'-trichlor-4,4'-cyaζnobiphenyl 52.2% salt was added to 80% salt, and the resulting salt-yield paste was stirred overnight in a bowl over ice.
After adding sO, the mixture is gradually bis-diazotized with 4.*iia* sodium 111 waves 2 6- while stirring at O to 5C. Commercialization of the threatened bisdiazoequum aS#1 as an MII agent
So, the soil should be added to the water after 500 liters of water.11
dilute to

44g of 1-acetoacetylamino-4-methane, pen, 400$ and rissx blue soda *
201Fj1ml K#, filtered using activated carbon and diluted with water to 500% weight. The prayed two-1 [at once #offering while stirring? 5-IIK period-buffer 1 wave-this company 54% may-/liquid 50 stmz ice Adding a wave to the 1K, the IL response is detected and flows into the 4* channel. Coupling layered pigment set I
Add dish sulfur nut 4s@ to II wave 31L, 98C
Heat to IM, stir at this temperature for 1 hour, and then
Single L Omushi Imono using the usual method.

Takukashi 1 Yellow is also missing the A family, and has a soft-770 #C song, OII, perfect O, and a transitional state rate.

II 4 (Ratio soft example) Example 5 ICm''C start 〇- (Implemented, but without adding sodium sulfate, I4 becomes. Threatened - oblique soft - PVOK birth olIvts-b-h'taam In order to write about the characteristics of writing, the ink is noticeably different from the book.

Example 7 2.2: Milk 5''-Tetrachloro4.4'-Cyanobia
- Chlorobenzene 5till Kyoto 400 @ part weight 56
% diluted sodium hydroxide, and then dissolved in stearyl alcohol #14 and 26% in ethylene oxide.
4 Ruyo Tadenru & I Ousei Imono 0101 Aqueous lll1 Housing 2o
Precipitate with 94 Nlll pH 14 parts by volume under good quantity 0 concentration test! The bisdiazonium was destroyed for 1 hour under stirring using 0*M dispersion mfR waves, during which 4N acetate and iron drops were added to the reaction mixture. Approximately 4 to 45 hours depending on the work.

After the coupling is completed, introduce Niho Sutai $1 rim 7s to the disazo 1w5oss box, and introduce Honganki □ Gai vbc#c
mlllAL and re6mJlflll1M.

A greenish-yellow material with far back buds is obtained, which is washed until pale, dried at 60C and ground to a maximum of 11 mm. The pale yellow pigment exhibits a transition state to soft-rvc K@NiQII Arashiko 1.

Even 8 (relative example) Example 7 KkIllO is carried out, however, there is one difference between the two sales force 9 and the 11 JIL electric power. The resulting pigment is soft!
It has a black %/'h transition state rate method after entering the ma OK song.

9ts'-dilvx#-44'-cyanobiphenyl 5 (L611) is bisdiazotized by the method described above in Example IK. 511K and 4-acetoacetyla (no 2
．． 4-Dimethylben~455atKyoro00@ji@f
c5sN bend ml-1140 capacity goam
Make the alkaline liquid clear at low temperatures, and add 1 liter of hot water for coupling with 1 liter of stearyl alcohol and ethyl alcohol. ONmast 5ml Quantity 114Dlilljil
Refrigerate to 96% 11 volumes 28 volumes under stirring. After adding 10G of sodium chloride to the resulting suspension, add 100ml of bisdiazonium solution to the resulting suspension. Immediately after the coupling layer was added, potassium sulfite 811 was added, and water vapor was introduced at a pigment layer temperature of 1N for 11 hours. YaSc5
Heat to cm. 60CfC Cooling 1 & Filtering with hot water until it becomes free of filtration. −, smear and grind. ζ01mKII good yellow color - OTV% Ascitic acid resistance.

1G (relative soft example) Perform as described in 9, but remember to add 2 sulfur-*l? A1
1111JIIL&? A#^Nal, BTT, and IS pigments have greater resistance to #ls than pigments like IM9 and B.

Example 11 s, s'-Siroru 44a-Sia (Nojifuel 5α
61K to book 600@fi department and 5 summer salted salmon 260 judgment at
Stir together, cool to oC with ice, and use 401g of 525 g of 0PIji! ! The bisdiazonium salt solution is converted into bisdiazotized by IC at 20 to 25C with sufficient stirring. Aceto 1m112 Ali-Sodo Alka 11 is filled with t, m from the #casing to obtain a friend-IIc, and the 70S-S tubing suspension 110wH-value is maintained at 45 to 5, the bis Diazonium salt O reaction layer weight a suspension 1!
Addition of Kli sulfur compound 5- and introduction of Minase O) to-? 61:'KJII heat, keep at MζO temperature for 1 hour, then cool to 70C, filter, IIAjliKk
Wash and dry until h.

The resulting pigment has completely satisfactory Kame-Kami-Kojiichi and Kyo-Koji properties.

★Laglinda can be made with resin base 01F, alkaline sulfur salt, water bulk subsulfite, -BIII
Il sulfur ois or divalent sulfur ois, iii without so0*
At a point of 0, according to the Hiroma-○IK theory, the color decreases considerably due to the carpenter's chestnut patch Km, and a pigment having a topcoat and smudging ratio method is obtained.

Even 12 In a modification of the method according to Example 11, Example 110 was prepared as follows.
Part I flows all at once into reaction vessel 10, in which acetic acid and Table II activator have already been charged. LAXO nitrous oxide in the pigment yield in the suspension wave turbidity cup
Foundation 85-9 with water bulk force 99A and jacket heating
0CK11A and kept at this temperature for 5 hours.

Next, apply KtkI&Ni to Example 11, and the resulting pigment will be completely perfect.
do.

EXAMPLE 15 Example ttK is repeated, except that it is made alkaline with 70CK cylindrical soda solution and then carried out according to German Patent Application No. 2502509 O Example 1]. The pigments obtained in this process have high hiding power, high gloss and high gloss. Furthermore, even in a carpenter's Qin batch O Yang Kai, a homogeneous crystalline substance with satisfactory oth- er and smudge properties can be obtained.

Claims (1)

[Claims] t. Improvement of technical properties of the following 2-suazol family! Experimenting with the JF method, Otsuzuring □III is obtained, -Yari formula (where m, 1 and 4 are methyl-, methoxy-, ethyl-, s*, 6s can also be the same- or ^1) 1% O The above-mentioned method of adding sulfur salt ions from 1 to 3 to 100 ml and adding sulfur salt ions and adding n+m to the chloride value. 2 In the general formula, R1 and 4 at the 2-14- or &iS- positions represent methyl-, metho-, or chlorine, and X means 8 liters of water. O method. Gourd Jisuazo drama is a sea fist a;re pigment knee-
86, Ai Cao Xu Kirigu Omaro - 1st stroke or 2nd a starting O method. tun Sulfite ions are converted into divalent sulfur or Machinohomu sulfur salt,
Adding bisulfite or bisulfite, II request 0
1111 years old method described in any of paragraphs 1 through 6. Add 50 to 10 oct of the concentrated liquid for half an hour to two hours.
cJiis Sokoi Request O Soul - Section 1 no m24aOhzure ThKEI1m07ms