JPS58203182A - Dyeing and printing method - 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 The present invention relates to a dyeing and printing method using an aqueous dispersion of water-insoluble azo pigment particles with a particle size of 0.05 μm or less, and the purpose of the invention is to dye and print polyester synthetic fibers and other materials. The object of the present invention is to dye or print a mixture of fibers with the same coloring matter vividly and uniformly with excellent fastness.

Conventionally, polyester-based synthesis ￥! For example, in the case of a mixture of polyester and fiber with cotton or viscose rayon, dispersion dyeing is used to dye the polyester fiber side, such as iM spinning, cross-knitting, cross-knitting, etc. of 2-vertebral fibers and natural fibers or other synthetic fibers, etc. The phase is used as a direct dye on textiles such as cotton as a reactive dye.

Vat or naphthol dyes were used. In addition, for a mixture of polyester NH and wool or nylon synthetic fiber, Bunko dye 1 and acid dye or metal-containing complex salt riI! Another was used.

Therefore, dyeing or printing methods were used that were compatible with the nature of the fibers and dyes.

In practical use, there are many melting points when dyeing or printing blended fabrics, mixed fabrics, etc. made of sandalwood fibers using these several types of different dyeing techniques. For example, the unique method of dyeing is complicated, and reproducibility is poor due to decomposition and insufficient placement, and the tube sheet is moldy.J4N! It is difficult to obtain uniform color tone of l1lj dyes, and it is unclear. It is complicated to change the blending ratio of different dyes depending on the mixing ratio. Requires more dye (approximately twice the amount in total), and more! There were drawbacks such as contamination of the II fiber side and the occurrence of inconvenient cracks such as in-white hot water dyeing and deterioration of light resistance.

On the other hand, according to the pigment resin dyeing method, it is possible to dye the same color at the same time using the same dye in a single operation, but the dispersed particle size of the pigment used is limited to 0.5 to 5 μm. ,
It's gross. Therefore, the color is poor, and since it cannot penetrate into the inside of the fine fibers, synthetic JRM resins, especially those that form a relatively flexible film, such as emulsions of polyacrylic esters, are used. This KN 1m fee aI
Used as an agent. However, this method has the effect that the texture of the fibers is not a little affected, and the product value is considerably lowered, and this drawback is particularly noticeable in the case of sea-colored fabrics.

Additionally, a method is known in which cellulose fibers are treated and dyed with water-insoluble organic dyes (including azo and anthraquinone yarns) at high temperatures together with water and a water-soluble organic bath agent. The difficulty of moisture management during the dyeing process, the need to select from only 44 very specific low-molecular wrinkle dyes, and the fact that it is twice as expensive as the dyeing process! A: A water-soluble organic bath agent is always required, which has various drawbacks such as low temperature during sharpening, hot water contamination, low dye yield, dullness in the washing process, and pollution. , industrially it is considered to be the first implementation.

The inventor of the present invention, as a result of extensive studies to solve this problem, found that ultrafine water-insoluble azo organic pigments with particle diameters of 0.01 μm or less are made from cotton.

The organic pigment has a direct effect on cellulose fibers such as rayon, acetate, and similar fibers, easily penetrates into the fibers, and is dyed with good yield. Because of their high melting point, they can be thermally sublimated (even those that do not exhibit disperse dye behavior are compatible with synthetic fibers, polyester fibers, and nylon fibers), and are commonly used as materials when reading temperature. They discovered that it can be dyed.

By the way, conventionally, as a method for producing an aqueous pigment particle dispersion,
The diazo compound and the coupling component were mixed and coupled to precipitate alI, which was then distributed to individual households and then dispersed in water using a mill together with a dispersant. However, even though this method requires a long dispersion process as well as processes such as filtration, washing, and dehydration, the pigment particle size can be reduced to 0.05μ or less, and water-insoluble pigments that cause secondary aggregation can be used.
It is almost impossible to stably subdivide the J material into image densities using a dispersant or a water-soluble organic bath agent in water.

As a method for improving this, for example, a method is known in which a diazotide and a coupling agent are coupled in the presence of a large excess of a nonionic dispersant (especially a high E.O. adduct). Compared to the conventional grinding method using mechanical means, this method produces fine particles in a much more homogeneous manner. However, using a dispersant alone will only result in a suspended coupling state, and the limit is about 0.5 to 0.1μ, and fundamentally, it is not possible to produce fine pigment particles that approximate a monomolecular shape. I can't do it.

The present inventor has developed the method of the present invention as a result of extensive research in order to obtain a highly concentrated and uniform aqueous dispersion of a water-insoluble organic pigment with a particle size of 0.05 μm or less.

Next, the ji14a of the present invention will be explained.

In the present invention, in a mixed aqueous solution of polyethylene glycol type nonionic foil II, urea and a water-bathable organic solvent,
Microparticle water with a water-unbathable structure having a particle size of 0.05μ or less obtained by coupling a diazo compound of aromatic amines with a coupling component such as a phenol, an amine, or an active methylene compound. Natural fibers using dispersions.

This is a dyeing and printing method characterized by dyeing or printing recycled fibers, semi-synthetic fibers, sweet acid fibers, or mixtures thereof.

The polyethylene glycol type nonionic surfactants used in the present invention include -grade alcohol ethylene oxide adducts, alkylphenol ethylene oxide adducts, fatty acid ethylene oxide adducts, fatty acid amide ethylene oxide adducts, and higher alkylamine ethylene oxide adducts. Examples include adducts, polyvalent T alcohol ethylene oxide adducts, fat and oil ethylene oxide adducts, polypropylene glycol ethylene oxide adducts, etc., and pigment subfine particles or single molecules with a particle size of 0.05μ or less are stable in water. It is an indispensable component for maintaining good dispersion, and also has the effect of blocking the large cohesive force between pigment monomolecules that form coupling 1M. Accordingly, the amount used is appropriately 0.2 to 4'ILL, especially 1 to 11 parts of the produced pigment, depending on the structure of the target pigment.
It is desirable to use a portion of 2MkJi to 2MkJi. That is, in order to economically obtain a pigment fine particle aqueous dispersion with high concentration, generally,
It is desirable that the a content is 8 to 20%, or it can be increased or decreased depending on the pigment concentration, and its relationship with the increase in wearable viscosity (due to a significant increase in surface area) due to the permanent formation of the fine particles. will be considered. In addition, the blending ratio of urea and water bathing organic solvent, which will be described later, is high, and an increase in these ratios can generally reduce the blending amount of the nonionic surfactant. History #4 Structurally, hydrophilic groups, especially acylamido groups and alkoxy groups.

It is desirable to reduce the amount of nonionic surfactants, and on the other hand, those containing nitro groups and halogen groups,
Is there a need to increase this?

However, if the amount of polyethylene glycol nonionic surfactant used is less than 0.2 mft part, the dispersion state becomes unstable and secondary aggregation occurs, and no matter what method is used, secondary particles or single molecules It is extremely jealous to do so.

In addition, when the temperature exceeds 4, the viscosity increases due to hydration of the interfacial viscosity agent, which makes stirring operation difficult, and also tends to impede the M concentration inside the fiber and reduce the dye acceptance rate. shows.

The surfactant preferably has low foaming properties, and the number of moles of ethylene oxide added is 15:'.

The amount is selected from a range of 100 to 100 moles.

Next, urea alleviates the simple viscosity persistence state caused by the vast surface area of pigment particles or single molecules of 0°05μ or less in water, promotes viscosity reduction, and imparts an appropriate hydrotrobi effect. However, the most important action is the presence of polyethylene glycol-based nonionic surfactants or phenols in a strongly alkaline aqueous solution in an unstable suspended state, preventing them from coupling as aggregates. That is, the suspension is dissolved by γH to obtain a uniform solution state. This effect is probably due to the presence of a strong acid or a strong alkali as a buffer, as well as stably retaining the surfactant and the coupling component in water as a bath solution. In addition, urea also has the effect of increasing moisture retention during dyeing of fibers and making color development more vivid.

The amount of urea to be used is preferably from 02 to 4 volumes per 1 part of the produced pigment, but in general, the more it is used within that range, the more effective it is.

In the present invention, polyethylene glycol has non-ionic properties = water bathing properties used with injections and urea.
Examples of solvents include alcohols such as ethyl alcohol and isopropyl alcohol, glycols such as ethylene glycol, diethylene glycol, and polyethylene glycol, polyhydric alcohols such as glycerin and pentaerythritol, methyl cellosolve, amino T alcohol, thiodiethylene glycol, dimethyl formamide,
Demethyl sulfoxide, 4-methylpyrrolidone, etc. are mentioned, and these are used to stabilize diazotized products, dissolve coupling agents, and directly use the D material obtained by coupling The pigment particles are made into fine particles or dissolved, and the pigment particles are stably dispersed.
It has the effect of acting as a leveling agent or dye accelerating agent for certain formations.

Therefore, it is appropriate to use 02 to 4 parts of the water-soluble 44 maple agent per 1 bundle of produced pigment, and in general, from the viewpoint of the pigment structure, it is particularly suitable for those having an acetoacetyl group. In general, a range of 0.5 to 100 parts based on the pigment produced is most appropriate.

The above polyethylene glycol type partially ionic surfactants,
The urea and water-soluble organic solvent used in the present invention have a particle size of 0.
It is not necessarily clear whether they are essential for the production of aqueous dispersions of fine pigment particles of 0.05 μm or less, or why such ultra-fine pigment particles or single molecules can be obtained.
Probably, the diazo component and the coupling component of the stable system, which are completely slow, combine extremely rapidly in the coupling reaction system, suppressing the growth and aggregation, and causing a capsule membrane-like structure over many regions. This is thought to be because it exhibits a covering effect and separates each single molecule. In particular, the nonionic surfactant Rindoku generates heat in the ultrafine system immediately after coupling.
It is interpreted that urea and water-soluble organic solvents in particular prevent the inevitable destruction of dispersion ability and therefore the aggregation of pigment single molecules.

The pigment microparticle water drink of the present invention 6ζ for mosquitoes can be obtained only by the concerted action of the above six components.

Next, the aromatic amines used here are preferably those that do not contain water-soluble groups such as sulfonic acid groups and carboxyl groups, such as halogen-substituted anilines, nitro-substituted toluidine, carbamide aninodine@ , TLT conversion bentidine pigeons, etc., specifically,
DG water-based azo intermediates such as varanitro-orthotoluidine, 2.5-dichloroaniline, dianisidine, dichlorbenzidine, aminoanthratenone, naphthylamine-bentacarbamide orthoanisidine, etc. are used;
It is selected by considering hue, fastness, Song 1 rate, h←lightness, and whale.

The diazotization reaction of aromatic amines is carried out by a conventional method, but it may also be carried out in the presence of a polyethylene glycol type nonionic activator and a water-soluble organic solvent. The case is interesting because it is superior in the mm state. However, when blending urea, it is necessary to convert it into cya-1zo. Furthermore, as diazotides of aromatic amines, diazotides in the form of double salts of diazotides and zinc chloride, silicon fluoride, etc. may also be used. For example, diazotides of aminodiphenylamines, black Salt etc. are used.

In addition, the components coupled to the diazo compound are:
Selected from phenol, naphthol, derivatives thereof, amines, amine derivatives, phenylpyrasolone M, imidazoles, triazoles, etc., such as salicylic acid anilide, β-naphthol, β-hydroxynaphthoic acid anilide. and β-hydroxynaphthoic acidamide, metaacetylaminoaniline, resorcinol ethylene glycol ether, 4-methoxy-1-naphthol, acetoacedoanilide, phenylmethylpyrazolone, benzimidazole, and 4-hydrobordibenztriazole.

By combining these coupling components with the diazo component described in @, an aqueous dispersion having most of the hue ranging from yellow to orange to red to purple to navy blue to black to green can be obtained.

In the coupling reaction in the present invention, the formation of similar particles and the dispersion of the obtained fine particles or monomolecular dye are carried out simultaneously with or immediately after the coupling of the diazotide and the coupling component, so that the coupling reaction is rapid. Along with heat generation and increased viscosity, if the pigment is not straight, local heat generation often occurs, and the desired particle size may not be obtained. Therefore, in order to carry out the coupling reaction of the present invention smoothly, it is necessary to pay special attention to reaction conditions such as temperature during the reaction, PR, S degree of each component, mixing method, and stirring method.

In this case, especially regarding the content of 1r#, 8
Preferably, it is between 20% and 20%. If the number of cases is 8% or more, it is less economical, and it also promotes conspicuous movement between pigment particles, which tends to cause agglomeration and requires a large amount of surfactant, etc., while if it is 20% or more, The viscosity is lower than expected, and stirring becomes impossible, leading to coagulation of the gold thread (unsuitable).

Using this superior moisture covering of azo fine grain-like particles with a particle size of 0.05μ or less, Eiseki-san or Naki-Q@+'k
t'μI do.

In addition, the dyeing solution or printing paste may contain pH
Auxiliary agents, leveling agents, accelerators, thickeners, metal ion sealants, etc. can be added and used together, and the constituent comb latex,
Polyacrylic acid ester emulsion, methylolated melamine, methylolated urea, formalin, etc. can be added and used in combination.

The moisture content of the pigment fine particles in the present invention can be reduced by long-term storage at low temperatures of -15 to -20°C, but at 7M, at temperatures above 60 to 80°C, fine particles tend to form, and secondary agglomeration may occur. Care must be taken as there is a risk of increasing adhesion. Furthermore, since it becomes extremely stable about 25 hours after coupling, the dispersion should not be diluted with water until about 24 hours have passed immediately after coupling.

Next, in the present invention, a dyeing solution or a printing paste is prepared using the dispersion cup, and the dye is processed into fibers by a known dyeing method or printing method. Then, if necessary, washing and soaping are performed.

The fibers targeted by the present invention include natural fibers such as cotton, linen, silk, and wool, recycled or semi-combined B2M fibers such as rayon, cupro, polynosic, acetate, etc., synthetic fibers such as polyester, nylon, polyacrylic, and polyvinyl. The objects of processing are 1wL products, loops, blended yarns, blended fabrics, mixed woven fabrics, etc. made of these fibers, especially cotton and polyester fibers and their fabrics. It is extremely self-effective against hanging, and blends or cross-woven fabrics, as well as fibers with different chemical and chemical properties, can be simultaneously treated with the same coloring agent by one coloring operation. A special effect of the present invention is that the same color can be uniformly and clearly colored. Therefore, organic pigment fine particles with a particle size approximating that of a -order particle or monomolecular state are released from the strong cohesive force and easily and efficiently penetrate into the fiber microstructure. and spread as well.

This is thought to be due to secondary aggregation within the reheating chamber.

Next, the effects of the present invention will be listed.

(1) According to the present invention, natural fibers, regenerated fibers, semi-synthetic fibers, and synthetic fibers can be dyed or printed using known dyeing methods or printing methods.

(2) According to the present invention, fiber mixtures such as blended yarns, blended fabrics, and mixed-woven fabrics can be uniformly and vividly dyed or printed in the same color at the same time by a single coloring operation using the same dye.

(3) According to the present invention, the processes such as filtration, dispersion, and wastewater treatment that are required in the conventional production of azo dyes and pigments are no longer necessary, and the production time is conveniently shortened, resulting in production efficiency. ka1b゛]i.

(4) The pigment fine particle aqueous dispersion of the present invention can be applied to the pigment resin dyeing method and the Shimari resin printing method, and the use of a concomitant inoculant is easier than when conventional pigments are used. can be significantly reduced. Also, the clarity and color power are 10.”
In addition, the texture of the workpiece becomes noticeably better.

(5) The water-dispersed face-imitating particles of the present invention are extremely cheap, do not cause sedimentation or coagulation during storage like conventional pigments, and are free from water-soluble organic solvents and urea. It exhibits level dyeing and accelerating dyeing effects when fine particles are used to dye fibers.

Example 1 4-pendelsulfonyl orthoanisidine 160 electron 1
1 or less, J11 parts are abbreviated as parts), hydrochloric acid 15F1. Liponox LOR (commercial city name) 180 cities and enalene glycol 70 &! Thoroughly knead the mixture, dilute it with 400°C of water, add 120 parts of a 40% sodium nitrite aqueous solution over 60 minutes while stirring at a temperature of 10°C or less, and add 120 parts of a 40% sodium nitrite aqueous solution over 60 minutes. After finishing the reaction, 50 parts of urea was added and the mixture was stored at 0°C. Separately, beta hydroxynaphthoene para-anisidide 1
80m, 20% caustic soda 144ml, urea 80%
1 part, 210 parts of Liponox LOR, 100 parts of ethylene glycol, and 150 parts of water were uniformly and transparently mixed, and while keeping the temperature at 0°C, added the diazotized viscous liquid to make the coupling. Red Mll fine particles (particle size 0.0
08-0.05μ) aqueous dispersion was obtained (viscosity s, o o
oc, p-8).

10 parts of an aqueous dispersion of fine red pigment particles.

Mix 2 parts of Demol) JtM product name, anionic dispersant), 1 part of alginic soda, and 87 ml of water, pad with cotton broadcloth, squeeze with a mangle, and dry.
A heat treatment was carried out at 0° C. for 2 minutes, followed by soaping, washing with water, and drying to obtain a plain dyed cotton broadcloth in bright vermilion. The washing fastness of this dyed product was 5th grade, the rubbing fastness was 5th grade, and the light fastness was also 5th to 6th grade.

On the other hand, for comparison, when similar coupling was carried out using Example 1 except for urea, the coupling component was in an oily state that could be separated into two layers, and the total (coupling suitability) was Because of the lack of water, we performed 8 couplings using a dilute solution of 2 times the total amount of water, but the obtained particle size was coarse, 6 to 0.5μ, and this was also When the cotton broadcloth is dyed, it becomes a pastel makoto color, and most of the color is bleached with a pin finish, making it completely (
I didn't dye it.

For historical comparison, when carrying out the coupling in the above-mentioned Example 1 except for urea and ethylene glycol, it was necessary to add 2.5 times as much water as the coupling component, and it was extremely Stirring was difficult due to its viscosity (unmeasurable when the viscosity exceeded 200°(]OO).The particle size of the resulting pigment was approximately 0.5 to 1.0μ, and DiJ
Even though it was subjected to the dyeing treatment as described above, it was almost non-dying. In history, similar heat-treated salt was applied to dyed adult cattle using ethylene glycol and water, but it was not effective at all (the line color improved considerably when the treatment temperature was set to 260°C). or1
．． The cotton broadcloth turned brown noticeably and its strength decreased.

Example 2 70 parts of dianisidine 9 salt H155m, glycerin 1
00 parts, Neugen ET-17Of brand name) 4069 and 5'60 parts of water (mixed, diazotized by adding 200 parts of 40% sodium nitrite bath at -5°C,
By adding 40% of urea and sulfamine, a diazotized brown transparent liquid was obtained. Separately, 162 parts of acetoacetoluidide, 145 parts of aqueous caustic soda solution, 50 parts of glycerin, 50 parts of 'I'-170 in Neugen, 82 parts of urea and 600 parts of water were mixed to form a colorless transparent liquid.
At -2°C, mix and couple the above diazotized solution to produce orange pigment fine particles (particle size 0.01μ or less).
An aqueous dispersion was obtained (viscosity 2,000 C. P-FA).

The obtained orange water tb @ 211 was dyed into water 98 to create a beautiful color.Using this dyeing material, acetate shantung cloth was dredged at 50-80°C for 40 minutes, and then soaped. After washing with water and drying, a plain dyed acetate shantung cloth was obtained in a clear orange-yellow color.

In addition, the obtained orange aqueous dispersion, Yodozol mR-
96 (a Product name, polyacrylic acid ester emulsion,
4 parts fat content 38%) 5 parts mineral subiritsu 40m, water 40!1 and emulsifier 5 parts mixed, press 100 million times, oil-in-water solid emulsification pigment ultra-fat printing! 4! ! Samurai glue, using this,
A polyester, cotton/M, Th broad cloth was screen printed and heat treated at 200°C for 2 minutes to obtain a print exhibiting a clear deep orange pattern.

For acetate cloth and polyester/cotton blend fabric, the next-order fastness was 4th to 5th grade, the dry cleaning fastness was 5th grade, and the light fastness was 4th grade, and the prints had a good texture.

For comparison, Matsumin Neo Color Orange MG, which is a dispersed pigment produced by the conventional coupling method on polyester/cotton broadcloth, is the same as #4.
DI Fi! When 566 people used 9 particles with a particle size of 2 to 0°8μ), the resin was 4 times that of the resin used in Example 21ζ,
The washing fastness was grade 6 to 4, and the texture was not comfortable to wear, and although it was pastel and bright, the luster of the fibers had disappeared.

However, the light resistance was the same as in the example.

Implementation Sailing 3 Orthorectal Tropara Chloraniline 90, Salt ill 1
551Z, llt acid 101%, polyenalene glycol #200 + product name) 20, Emulgen 985 (
Product name) Mix 60 items and water 650 i, s>, 0~
Diazotize with 40% sodium nitrite aqueous solution 95% at 5°C to obtain a light brown transparent liquid, separately add acetoacetate + 1 liter 001 m, 20% W soda 1 liquid 120 ml
, polyethylene chloride 3Q bl, dimethylformamide NIDD, 60 parts of urea and 790 parts of water were mixed, the colorless and transparent coupling solution was kept at 0°C, and the above diazo chemical reaction was carried out with stirring. Coupled with MH and added with sodium phosphate and sodium bicarbonate.
It is neutralized by adding yellowish brown pigment particles (particle size 0.01 μm).
(d) An aqueous dispersion was obtained (viscosity 2.000 e-p-81
゜The obtained 5 yellow-brown water dispersions and 95 etherified locust bean gum 7 aqueous solutions were mixed and a printing paste was applied.
A pattern is printed on a polyester knit cloth using Nikleen printing, followed by high-pressure steaming at 160°C for 60 minutes, followed by soaping.

After washing and drying, a multicolored polyester knit cloth with a pattern of bright green and yellow was created.

The light resistance of the printed material is 5 to 6, and the washing fastness is 5, w
: Abrasion resistance was grade 5. In addition, I- in the 11th century example
p: Coupled products containing 11 particles of plain and polyethylene glycol have a particle size of 2 to 1μ, and are considerably stained in the same dyeing process, but as a result of reflectance measurement, only 68 beaks were dyed and the dyeing time was It was about 42%, or twice as much.

However, the fastness of the embroidery on the vermillion color is almost the same as that of the actual embroidery, which is good.

' = Example 4 Alpha Amino Anthra 17th Diazo! 'Fast Redn Rutom L (product name) whose nose is made with a salt made from salt.
666 capitals, glacial acetic acid 66 capitals, ribo z”z7xhG'I'(
d product name) 240gts, 150 parts of urine, 67 parts of water (pour J-to, freeze and humidify to make a uniformly transparent brown color, add 54 to potash, 108 to glacial acetic acid, 108 to glacial acetic acid, Ribonosoxum O'I'60 1 part, polyethylene glycol 400 (6 to 1 part), Lihonox LOR (trade name 140
Miyako.

and 646 parts of water to make a transparent brown powder, stir well and add the above diazotized solution at 0 to -2°C for coupling, to form yellow-orange pigment fine particles (particle size r 1.05 μm or less). ) A moisture rug was added (viscosity 10,500C-P-8).

A printing paste was obtained by mixing 5 parts of the obtained yellow-orange aqueous dispersion, 94 parts of a 7% aqueous solution of etherified locust bean gum, and 1 part of metanitrobenzene sulfonate soda. ? a (65: 55
Mixing rate) Screen printing method on float cloth - (4 fathers are printed, subjected to high temperature steaming at 180℃ for 10 minutes, soaped, washed, and dried to create a bright yellow-orange pattern in 4 colors.A polyester/cotton blend. A printed broadcloth was obtained.

This printed product had a washing fastness of class 5, a washing fastness of class 5, and a light fastness of class 5, and the polyester side and the cotton side were uniformly dyed in the same hue.

In addition, the pigment particles containing urea and water-based organic solvents in the examples are extremely coarse, and even when pulverized in a three-roll mill, the particle size remains about 2 μm or less, similar to the dyeing process used in dyeing. Even after treatment, the cotton side was not dyed at all and remained white, resulting in a buffed print.

Example 5 140 parts of 4-amino 1-benzoylamino 6.6-di-engineered toxybenzene, 110 parts of hydrochloric acid and 400 m of water were mixed, and 1
At 5℃, add 40% sodium nitrite and 11U'C of sodium nitrite! j
ll L is a greenish yellowish brown transparent diazo-chemical trout, and it is
Cool to -5°C, add 120 g of beta-hydroxynaphtho, orthotoluicide, 1 g of diluted sodium chloride solution.
60 copies.

Emulgent #49 (M product name) 50% aqueous solution 200ml
, 11 times 60 parts, triethylene glycol 60 parts, and 400 parts of water were mixed and dissolved to obtain a coupling liquid.
℃, add and couple the diadiazol compound described in the mij.
．． 01μ) Aqueous dispersion is samurai. Obtained 2' water dispersion @lO
Miyako, urea 2 mark.

A padding solution was made with 2 parts of ethylene glycol and 86 parts of water, and a nylon taffeta cloth was dipped in the mixture.After drying,
The fabric was steamed at a high temperature of 180° C. for 12 minutes, soaped, and dried to obtain a nylon taffeta fabric dyed with a bright reddish-blue solid color.

The washing fastness of the dyed product was 4th grade, and the light fastness was 5th grade. On the other hand, in this example, experiments were conducted on samples in which the water-soluble organic solvent and urea were removed, and those in which both were removed, and their performances are shown in Table 1.

Table 1: Dyeing properties are ranked ◎, △, and × in descending order of the print quality.
is displayed.

From Table 1 above, it is clear that this example is superior.

On the other hand, the non-ionic surfactant in the coating 1 was only partially observed as spots, or it was only a faint 4-color because it came off when soaping.

The grades in the above examples are in accordance with the JIS standard,
Light resistance was expressed based on L-08[11.

Toku E-de Hosota Matsui Shiki Kagaku Kogyo Co., Ltd. Agent
Person Patent Attorney Takashi Ihizu Tomi 1 Procedural Amendment (Method) % Formula % 1. Display of the Case 1988 Patent Application No. 1427 2. Salt of the Invention 1.

Dyeing and collar dyeing method 3, relationship with the case of the person making the amendment Patent applicant address: 29 Nishino Rifu-cho, Yamashina-ku, Kyoto City Meine Co., Ltd.
〼4, Agent 〒540 Address: Tenzuwa Chiyoda Building, 1-15 Tanimachi, Higashi-ku, Osaka, Italy - Patent Office 5: Date of amendment order: May 11, 1988 (Shipping date: 58.5.31 > 7
Yours\6, correction vs. specifier 7,? As per the attached sheet, we will also submit a detailed statement clearly marked with type stamps (black).

8. 1. 1. 8. (1) Specification: 1 copy that's all

Claims (1)

[Claims] 1. Polyethylene glycol type nonionic surfactant,
Particles with a diameter of 0.5 mm obtained by coupling a diazotized aromatic amine with a coupling component such as a phenol, an amine, or an active methylene compound in a mixed aqueous solution of urea and a water-soluble organic solvent. Natural fibers, recycled fibers, semi-synthetic fibers 1 are produced using a water dispersion of fine pigment particles of 0.05 μm or less.
A dyeing and printing method characterized by dyeing or printing synthetic fibers or a mixture thereof.