CN102212276B - Blue reactive dye mixture and preparation and application thereof - Google Patents

Blue reactive dye mixture and preparation and application thereof Download PDF

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Publication number
CN102212276B
CN102212276B CN2011100855788A CN201110085578A CN102212276B CN 102212276 B CN102212276 B CN 102212276B CN 2011100855788 A CN2011100855788 A CN 2011100855788A CN 201110085578 A CN201110085578 A CN 201110085578A CN 102212276 B CN102212276 B CN 102212276B
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parts
dye mixture
dyestuff
minutes
fabric
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CN102212276A (en
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罗润富
罗俊龙
顾培农
邓今强
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HUBEI COLOR ROOT TECHNOLOGY CO., LTD.
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LIYUAN (HUBEI) TECHNOLOGY CO LTD
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Abstract

The invention discloses a blue reactive dye mixture. The blue reactive dye mixture is characterized by comprising a dye shown in a general formula (1) and a dye shown in a general formula (2 in the weight ratio of (68.6-60):(26.3-32). The dye mixture has excellent light color boosting capacity and high color fixing rate when dyeing or printing cellulose, has higher dyeing reproducibility than ordinary commercial dyes, and can effectively solve the problems of dyeing defects and staining; and the formula is low in cost. Moreover, the blue reactive dye mixture has excellent color fastness to sunlight and perspiration-light, and is applicable to various application processes.

Description

A kind of blue active dye mixture and preparation thereof and application
Technical field:
The present invention relates to a kind of blue active dye mixture and preparation thereof and application, belong to technical field of dye.
Background technology:
Along with in people life to the requirement that day by day improves of fabric color, cause the quality of dyeing and updating of dyeing, quality improve and cost aspect obtaining very great achievement.Now, market demand is for example to have enough substantivities, simultaneously can wash out well, easily the reactive dyestuffs of loose dyestuff.In addition, all dyestuffs should have good Dry Sack and high reactivity, and this Dry Sack and high reactivity are specially adapted to have the dyestuff of high fixing property.But in many cases, particularly in very dark dyeing, the dyestuff of prior art still can meet the requirement of above-mentioned aspect of performance, so printing and dyeing enterprise needs good reactive dyestuffs to dye the normal dark fabric of manufacture-illegal.
Summary of the invention:
The purpose of this invention is to provide a kind of blue active dye mixture and provide its preparation method and application method, in order to solve above-mentioned deficiency.This dye mixture is suitable for dyeing or printed cellulosic materials, is particularly suitable for dyeing or prints nitrogenous or the hydroxyl filamentary material, can produce good result.Reactive dye mixture of the present invention not only has good photostabilization, perspiration resistance and sunlight resistance, also have fabulous wet fastness and acidproof hydrolysis and alkali resistance, and have good fastness to chlorine and fastness to ironing, and have fabulous lifting force, level-dyeing property and good solubility and wash-out.Adopt inorganic salt and alkali all than conventional dyestuff, to lack during reactive dyeing of the present invention, belong to environmental protection type dye.
The feature of blue active dye mixture of the present invention is: it comprises the dyestuff of general formula (1) and the dyestuff of general formula (2), and the weight fraction in their mixture dyestuff, than for 63.6-50: 28.7-45, can add auxiliary agent during use on demand.General formula is as follows:
In formula, m is the numeral of 0-3, and n is the numeral of 0-2, and y is the numeral of 0-2,
X 1, X 2For F, CL,
D 1, D 2Be respectively one of following formula:
NH 2C 2H 4SO 2C 2H 4OSO 3H NH 2C 2H 4OC 2H 4SO 2C 2H 4OSO 3H
NH 2C 2H 4SO 2C 2H 4CL NH 2C 2H 4OC 2H 4SO 4C 2H 4CL
Figure BDA0000054312600000021
The present invention relates to the preparation method of formula (1) dyestuff, the method comprises the following compound that uses about 1 molal weight in every kind of situation:
Figure BDA0000054312600000022
The compound of formula (3) is pulled an oar in appropriate frozen water again, add hydrochloric acid, stirred 30 minutes, then in the time of T=5-10 ℃, sodium nitrite solution with 30% adds and carries out diazotization about 1 hour, keep T=5-10 ℃, hydrochloric acid and inferior sodium excessive response 3 hours, can obtain the diazonium salt of the compound of formula (3), then the neutral solution of formula (4) is added drop-wise to diazonium salt about 1 hour.
The compound of formula (6) was pulled an oar 45 minutes in frozen water, then the neutral solution of formula (5) is slowly joined in the compound of formula (6).At pH=5-7, T=5 ℃ was reacted 3 hours, then formula (7) was joined in the primary condensation thing, was warmed up to T=35 ℃, and pH=4-4.5, reacted 6 hours, then cools to 0 ℃, adds quantitative hydrochloric acid and inferior sodium, T=0-5 ℃ of reaction 2 hours.Eliminating excessive nitrous acid, the neutral solution of formula (4) is added to diazonium salt about 1 hour,, at T=5 ℃, during pH=3.0, reacted 8 hours, is reaction end until can't detect diazonium.Then the compound of formula (3) was pulled an oar 1 hour in frozen water, add appropriate hydrochloric acid and inferior sodium, at T=5 ℃, reacted 2 hours, finally this diazonium salt is added to for the first time in condensated liquid, regulates pH=6.5, T=5-8 ℃ of reaction 6 hours, be terminal until can't detect diazonium salt, can obtain meeting the dyestuff of general formula (1).Certainly, change synthetic middle unit process order and can obtain meeting equally the dyestuff of general formula (1).
Figure BDA0000054312600000031
The present invention relates to the preparation method of formula (2) dyestuff, the method comprises the following compound that uses about 1 molal weight in every kind of situation:
Figure BDA0000054312600000032
The compound of (9) in formula was pulled an oar 40 minutes in frozen water, then the neutral solution of formula (8) is joined in the mixture of ice and water of formula (9), at pH=5-6, T=0-5 ℃ was reacted 6 hours, and obtained the primary condensation thing, then with D 2Be added in the primary condensation thing, at pH=6.5, T=35-45 ℃ was reacted 6 hours, can obtain meeting the dyestuff of general formula (2).Certainly change synthetic middle unit process order, can obtain meeting equally the dyestuff of general formula (2),
Figure BDA0000054312600000033
The compound that the present invention is defined as formula (3) has:
Figure BDA0000054312600000034
The compound that the present invention is defined as formula (6) has:
Figure BDA0000054312600000042
The compound that the present invention is defined as formula (7) has:
NH 2C 2H 4SO 2C 2H 4OSO 3H (7-1) NH 2C 2H 4OC 2H 4SO 2C 2H 4OSO 3H (7-2)，
NH 2C 2H 4SO 2C 2H 4CL (7-3) NH 2C 2H 4OC 2H 4SO 2C 2H 4CL (7-4)，
Figure BDA0000054312600000043
The compound that the present invention is defined as formula (8) has:
Figure BDA0000054312600000051
The compound that the present invention is defined as formula (9) has:
Figure BDA0000054312600000061
The compound that the present invention is defined as formula (10) has:
NH 2C 2H 4SO 2C 2H 4OSO 3H (10-1) NH 2C 2H 4OC 2H 4SO 2C 2H 4OSO 3H (10-2)
NH 2C 2H 4SOC 2H 4CL (10-3) NH 2C 2H 4OC 2H 4SO 2C 2H 4CL (10-4)
Figure BDA0000054312600000062
The present invention meets the dyestuff of general formula (1) (2), can adopt spray method, the precipitator method and filter press technique and obtain, mixture dyestuff of the present invention can obtain the dyestuff of formula (1) (2) by a certain percentage through abundant mechanically mixing, the existence form of dyestuff has powder, fine powder, particle, liquid state, this dye mixture can also comprise some usual auxiliaries, as levelling agent, interfacial activity auxiliary agent, as softening agent, dust-proofing agent, fire retardant and static inhibitor.
The dyestuff of formula of the present invention (1), (2) contains an anion-radicals at least, as sulfonic group, for convenience of explanation, form with free acid in specification sheets represents, but to be all form with soluble salt in the finished product dyestuff exist for they, as lithium salts, potassium or sodium salt, especially take sodium-salt form as best.
Dye mixture of the present invention is applicable to dyeing or the various filamentary materials of stamp, as hydroxyl or contain amino filamentary material, the filamentary material that contains hydroxyl has cotton, jute, flax, sisal hemp, ramie and regenerated cellulose fibre, containing amino filamentary material has silk, wool, tynex and polyurethane fiber, can also print cellulosic fibre and spin intertexture with mixing of tynex or polyurethane fiber.
Above-mentioned filamentary material existence form can be: fiber, yarn, woven fabrics or knitted fabrics.
The applicable normal dyeing method of dye mixture of the present invention has: dip-dye, dye gigging, tie dyeing, cold flocking together, and preferred tie dyeing and cold flocking together, applicable conventional printing method has: rotary printing, PLATE SCREAM PRINTING, preferred rotary printing.
Usually dyestuff is made into the aqueous solution, salt adding (sodium-chlor, sodium sulfate) again, add alkali (sodium hydroxide, sodium carbonate, sodium bicarbonate, sodium phosphate), then impregnate fabric, two soak two bundles, the fabric that dyed gas in the saturated steam of 100-102 ℃ steams 3 minutes post rinsings, stamp is dyestuff and thickening material (sodium alginate, ether of cellulose), solubility promoter (urea), reserve salt (m-nitrobenzene sodium sulfonate) etc. to be made into printing paste carry out stamp, then with conventional dyeing and finishing aftertreatment, removes loose colour.
In sum, dye mixture of the present invention is dyeing to Mierocrystalline cellulose or is having splendid light lifting force during stamp, high colour-fast rate, and low-cost formula, have better reproducibility than general goods dyestuff, can effectively solve look flower and staining problem.And sun-proof and sweat proof light fastness are good, are applicable to multiple application art.
Embodiment:
In the following example, part refers to weight part, temperature with a degree centigrade expression, and the relation between weight part and parts by volume and gram are identical with the relation between cubic centimetre.
Embodiment 1, preparation of dyestuff
The cyanuric chloride of 18.5 parts is pulled an oar in frozen water, then the neutral solution of 21 part of 2.4 diamino benzene sulfonic acid was added at 1-1.5 hour, pH=6-7 reaction 3 hours, then 28.1 parts of 3-(β-ethyl sulfuryl sulfuric ester) aniline is added, be warmed up to 35-45 ℃, pH=4.5-5.5 reaction 6 hours.then this solution is cooled to 0 ℃, add quantitative hydrochloric acid and Sodium Nitrite to carry out diazotization, then the neutral solution of 1 amino 3.6 disulfonic acid of naphthols 8 is added in diazonium salt, at T=5 ℃, pH=3 reaction 8 hours, obtain the primary condensation product, then aniline 2.5 disulfonic acids were pulled an oar 1 hour in frozen water, add quantitative hydrochloric acid and Sodium Nitrite, T=5 ℃ of reaction 1 hour, this diazonium thing is added to for the first time in condensated liquid, at T=5 ℃, pH=6-6.5 reaction 6 hours, then remove insolubles with closed filter, remove large section inorganic salt and by product with nanofiltration membrane again, can obtain meeting the dyestuff (1-1) of general formula (1), this dyestuff can be dyed blueness with fiber.
Figure BDA0000054312600000071
Embodiment 2, the preparation of dyestuff
The cyanuric chloride of 18.5g was pulled an oar 45 minutes in frozen water, then with the neutral solution of 21 part of 2.4 diamino benzene sulfonic acid in 1-1.5 hour joins the cyanuric chloride of having pulled an oar, at T=5 ℃, pH=6-7 reaction 3 hours, then 3-(β-ethyl sulfuryl sulfuric ester) aniline is added, be warmed up to 35-45 ℃, pH=4.5-5.5 reaction 6 hours.Then this condenses is cooled to 0 ℃, add quantitative hydrochloric acid and sodium nitrite solution, then with the solution of 8 naphthols-1 amino-3.6 disulfonic acid of neutrality at T=5 ℃, pH=2-3 reaction 8 hours, then with aniline 2,5 disulfonic acids are diazonium method diazotization routinely, be added to for the first time in condenses, at pH=6.5, T=5 ℃ of reaction 6 hours, can obtain meeting the dyestuff (1-2) of general formula (1)
Figure BDA0000054312600000072
Embodiment 3-10
Synthetic method according to embodiment 1-2, choose the intermediate that is defined as (3) (4) (5) (6) (7) by the present invention, can obtain equally meeting the following dyestuff of general formula (1), they can be dyeing into filamentary material qualified blueness.
Figure BDA0000054312600000073
Figure BDA0000054312600000081
Embodiment 13, the preparation of dyestuff
The cyanuric chloride of 18.5g was pulled an oar 1 hour in frozen water, then with 5 amino of 59.6 parts-3-[3 phenyl-5 (2-hydroxyl-3.5 disulfonic acid)-1-methyl]-4 copper complex formazan neutral solutions of hydroxy benzenesulfonic acid add, at T=0 ℃, pH=5-7 reaction 3 hours, then 3-(β-2 ethyl sulfuryl sulfuric ester) aniline of 28.1 parts is added, at T=35-45 ℃, pH=4-5 reaction 6 hours, can obtain meeting the dyestuff (2-1) of general formula (2)
Figure BDA0000054312600000092
Embodiment 14, the preparation of dyestuff
The cyanuric fluorides of 13.5 parts were pulled an oar 40 minutes in frozen water, then with 5 amino of 59.6 parts-3-[3 phenyl-5 (2-hydroxyl-3.5 disulfonic acid)-1-methyl]-4 copper complex formazan neutral solutions of hydroxy benzenesulfonic acid add, at T=0 ℃, pH=5-7 reaction 3 hours, then 3-(β-2 ethyl sulfuryl sulfuric ester) aniline that adds 28.1 parts, at T=35-45 ℃, pH=4-5 reaction 6 hours, can obtain meeting the dyestuff (2-2) of general formula (2)
Figure BDA0000054312600000093
Embodiment 15-24, the preparation of dyestuff
According to the synthetic method of embodiment 13-14, choose the intermediate that is defined as (8) (9) (10) by invention, can obtain equally meeting the following dyestuff of general formula (2),
Figure BDA0000054312600000111
Figure BDA0000054312600000121
Embodiment 25, dyeing
With 2.7 parts of dyestuffs (1-1), after 1.3 a part dyestuff (2-1) is dissolved in 50 parts of water and fully stirs, with this solution impregnation cotton fabric, the pick-up that makes cotton fabric is 80%, then oven dry, then in room temperature with containing the sodium carbonate solution of 50g/l and the sodium chloride solution of 200g/l floods this fabric, then making the pick-up of fabric with bundle roller pressure is 80%, the fabric that dyed gas in the saturation steam of 100=102 ℃ steams 3 minutes post rinsings, soaped 15 minutes with non-ionic detergent under boiling, post rinse is also dry.
Embodiment 26, dyeing
With 2.53 parts of dyestuffs (1-2), 1.47 a part dyestuff (2-3) is dissolved in 150 parts of water,, with this solution impregnation cotton fabric, the pick-up that makes cotton fabric is 80%, two soak two bundles, and room temperature is chilled to 45 ℃, dry by the fire 45 minutes, pass through again hot water wash, cold wash, soaped 15 minutes with non-ionic detergent under boiling, in rinsing and dry.
Embodiment 27, stamp
By rapid stirring, with 2.62 parts of dyestuffs (2-1), 1.38 a part dyestuff (2-2) is sprinkled into 100 parts of sodium alginate thickening materials that contain 50 part 5%, 27.8 part water, 20 parts of urea, in 1 part of m-nitrobenzene sulfonic acid and 1.2 parts of sodium bicarbonate magma, use the printing paste that makes by this method to carry out stamp to cotton fabric, then steam 2-3 minute, then rinsing with the saturated steam gas of 100-102 ℃.If need and can soap under boiling, again rinsing and dry.
Embodiment 22, stamp
By rapid stirring, with 5.43 parts of dyestuffs (1-3), 2.57 a part dyestuff (2-4) is sprinkled into the sodium alginate thickening material of 150 part 5%, 109.5 part water, 30 parts of urea, in 3 parts of m-nitrobenzene sulfonic acids and 7.5 parts of sodium bicarbonate magma, use the printing paste that makes by this method to carry out stamp to cotton fabric, then steamed 5 minutes then rinsing with the saturated steam gas of 100-102 ℃.If need and can soap under boiling, again rinsing and dry.
The performance index that dyeing reactive dye mixture of the present invention is implemented dyeing or stamp to filamentary material are as follows:
Figure BDA0000054312600000131

Claims (4)

1. a blue active dye mixture is used for the method that dyes, and it is characterized in that:
With 2.7 parts of dyestuffs (1-1)
Figure FDA00003538140900011
1.3 part dyestuff (2-1)
After being dissolved in 50 parts of water and fully stirring, with this solution impregnation cotton fabric, the pick-up that makes cotton fabric is 80%, then oven dry, then in room temperature with containing the sodium carbonate solution of 50g/l and the sodium chloride solution of 200g/l floods this fabric, then to make the pick-up of fabric be 80% with pricking the roller pressure, the fabric that dyed is 3 minutes post rinsings of gas steaming in the saturation steam of 100-102 ℃, soaped 15 minutes with non-ionic detergent under boiling, post rinse is also dry.
2. a blue active dye mixture is used for the method that dyes, and it is characterized in that:
With 2.53 parts of dyestuffs (1-2)
Figure FDA00003538140900013
1.47 part dyestuff (2-3)
Be dissolved in 150 parts of water, with this solution impregnation cotton fabric, the pick-up that makes cotton fabric is 80%, two to soak two bundles, and room temperature is chilled to 45 ℃, dries by the fire 45 minutes, then passes through hot water wash, and cold wash, soaped 15 minutes with non-ionic detergent under boiling, and post rinse is also dry.
3. a blue active dye mixture is used for the method for stamp, it is characterized in that:
By rapid stirring, with 2.62 parts of dyestuffs (2-1)
Figure FDA00003538140900022
1.38 part dyestuff (2-2)
Figure FDA00003538140900023
Be sprinkled into 100 parts of sodium alginate thickening materials that contain 50 part 5%, 27.8 parts of water, 20 parts of urea, in 1 part of m-nitrobenzene sulfonic acid and 1.2 parts of sodium bicarbonate magma, with the printing paste that makes by this method, cotton fabric is carried out stamp, then with the saturated steam gas of 100-102 ℃, steam 2-3 minute, then rinsing; If need and can soap under boiling, again rinsing and dry.
4. a blue active dye mixture is used for the method for stamp, it is characterized in that:
By rapid stirring, with 5.43 parts of dyestuffs (1-3)
Figure FDA00003538140900031
2.57 part dyestuff (2-4)
Figure FDA00003538140900032
Be sprinkled into the sodium alginate thickening material of 150 part 5%, 109.5 parts of water, 30 parts of urea, in 3 parts of m-nitrobenzene sulfonic acids and 7.5 parts of sodium bicarbonate magma, with the printing paste that makes by this method, cotton fabric is carried out stamp, then with the saturated steam gas of 100-102 ℃, steamed 5 minutes then rinsing; If need and can soap under boiling, again rinsing and dry.
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CN103044969B (en) * 2013-01-22 2014-12-17 上海雅运纺织化工股份有限公司 Dye composition for one-bath and one-type based dyeing and dyeing method of dye composition
CN106544907B (en) * 2016-09-28 2019-07-02 杭州万事利丝绸科技有限公司 A kind of real silk fabric digital printing method for exempting from slurry processing
CN107020780B (en) * 2017-04-06 2019-10-18 南雄阳普医疗科技有限公司 A kind of composite fluorescent film and its preparation method and application

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