CN104672160B - A kind of compound in triazine class and its application as dye additive - Google Patents
A kind of compound in triazine class and its application as dye additive Download PDFInfo
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- CN104672160B CN104672160B CN201310636548.0A CN201310636548A CN104672160B CN 104672160 B CN104672160 B CN 104672160B CN 201310636548 A CN201310636548 A CN 201310636548A CN 104672160 B CN104672160 B CN 104672160B
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- 239000000654 additive Substances 0.000 title claims abstract description 44
- 230000000996 additive effect Effects 0.000 title claims abstract description 44
- 150000001875 compounds Chemical class 0.000 title claims abstract description 22
- 150000003918 triazines Chemical class 0.000 title claims description 10
- 239000012752 auxiliary agent Substances 0.000 claims description 17
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 13
- 239000010446 mirabilite Substances 0.000 claims description 11
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 9
- 229910052783 alkali metal Inorganic materials 0.000 claims description 6
- 150000001340 alkali metals Chemical class 0.000 claims description 5
- -1 alkyl naphthalene sulfonic acid formaldehyde Chemical compound 0.000 claims description 5
- 239000007859 condensation product Substances 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 4
- 229910006146 SO3M1 Inorganic materials 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
- NMDKWAQVRNUKQH-UHFFFAOYSA-N 2-benzylnaphthalene-1-sulfonic acid formaldehyde Chemical compound C=O.C(C1=CC=CC=C1)C1=C(C2=CC=CC=C2C=C1)S(=O)(=O)O NMDKWAQVRNUKQH-UHFFFAOYSA-N 0.000 claims description 2
- 229920001732 Lignosulfonate Polymers 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- NVVZQXQBYZPMLJ-UHFFFAOYSA-N formaldehyde;naphthalene-1-sulfonic acid Chemical compound O=C.C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 NVVZQXQBYZPMLJ-UHFFFAOYSA-N 0.000 claims 1
- 239000000975 dye Substances 0.000 abstract description 77
- 239000004576 sand Substances 0.000 abstract description 16
- 239000003513 alkali Substances 0.000 abstract description 14
- 238000004043 dyeing Methods 0.000 abstract description 12
- 150000003839 salts Chemical class 0.000 abstract description 12
- 238000003801 milling Methods 0.000 abstract description 10
- 239000000985 reactive dye Substances 0.000 abstract description 10
- 239000000986 disperse dye Substances 0.000 abstract description 6
- 230000009286 beneficial effect Effects 0.000 abstract description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical class C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 abstract 1
- 235000002639 sodium chloride Nutrition 0.000 description 13
- 230000000052 comparative effect Effects 0.000 description 11
- 238000000034 method Methods 0.000 description 11
- 239000002671 adjuvant Substances 0.000 description 9
- 239000002270 dispersing agent Substances 0.000 description 9
- 239000002245 particle Substances 0.000 description 9
- 238000001035 drying Methods 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000012065 filter cake Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000005070 sampling Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 238000006482 condensation reaction Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000009413 insulation Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- MWMJPPMTXZJLIK-UHFFFAOYSA-N 3-[4-[(2,6-dibromo-4-nitrophenyl)diazenyl]-n-ethylanilino]propanenitrile Chemical compound C1=CC(N(CCC#N)CC)=CC=C1N=NC1=C(Br)C=C([N+]([O-])=O)C=C1Br MWMJPPMTXZJLIK-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical compound C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- WFFKSTRPZWRBEW-UHFFFAOYSA-N n-[2-[(2-bromo-4,6-dinitrophenyl)diazenyl]-5-(diethylamino)phenyl]acetamide Chemical compound CC(=O)NC1=CC(N(CC)CC)=CC=C1N=NC1=C(Br)C=C([N+]([O-])=O)C=C1[N+]([O-])=O WFFKSTRPZWRBEW-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- 239000003643 water by type Substances 0.000 description 2
- WODGMMJHSAKKNF-UHFFFAOYSA-N 2-methylnaphthalene-1-sulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(C)=CC=C21 WODGMMJHSAKKNF-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 239000003674 animal food additive Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 150000003841 chloride salts Chemical class 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
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Abstract
The invention provides a kind of compound in triazine class（Ⅰ）, and such compound is used as the purposes of dye additive.The beneficial effects are mainly as follows：Dye additive of the present invention is added during commercialization of dyes, the solubility of reactive dye can be improved, prevent some dyestuffs from dyestuff is separated out from dye liquor because of degree of association increase after running into alkali, salt, success rate is once dyeed in raising；But also the disperse dyes sand milling time can be reduced, and improve and benefit is sanded, improve the level-dyeing property after dyeing.
Description
（One）Technical field
The present invention relates to a kind of compound in triazine class, and its as the application of dye additive.
（Two）Background technology
Although reactive dye are water-soluble dyes, but not exist with unimolecule state in aqueous medium.Once there is research
Show, be also with 6 molecular association bodies in pure water at room temperature even if the small molecule dyes as C.I. active blue 19s
What form was present, degree of association is bigger in the presence of having electrolytic salt (such as glauber salt).The dyeing of reactive dye need to be in alkaline medium
Carried out with glauber salt rush dye, and common reactive dye are not alkaline-resisting, when dyestuff and alkaline agent are present in the aqueous solution simultaneously,
Dyestuff can be hydrolyzed, and caused the degree of fixation of dyestuff and reduced.Vinyl sulfone(RemzaolHuo Xingranliaohuoxingjituan) class reactive dye are in dyeing course due to the effect of alkali
Slough water-soluble ester group and change into vinyl sulfone(RemzaolHuo Xingranliaohuoxingjituan), tendency of associating abruptly increase, solubility reduction makes dyestuff be separated out from dye liquor, Jin Er
Color dot dyeing defect problem is formed on fabric.Especially for the less dyestuff self-association degree of water soluble group in dye molecule just more
Greatly, uneven dyeing and the reduction of tinctorial yield are caused.When cold-pad-batch process is dyeed, dyeing temperature is low, medium is alkaline strong, dye molecule
Association be particularly acute.To solve this problem, DYE PRODUCTION business adds appropriate auxiliary agent in commercialization of dyes, such as open special
Sharp CN1621453A, CN102250493A, CN102260418A etc..These auxiliary agents improve alkali resistance to a certain extent, but molten
Xie Du is still undesirable.
The granular size of disperse dyes directly influences the cost of dyestuff and the quality of dyeing.Reduce the particle of disperse dyes
Size, can reduce dye dosage and simplified dyeing in dyeing course, can significantly improve the class and profit of dye product
With rate.So typically to add some auxiliary agents to carry out sand milling corpusculed, but prior art sand during disperse dyes commercial treatment
Time consuming is long, causes dye temperature too high, and some dyestuffs are easily decomposed.
（Three）The content of the invention
To solve the above problems, it is an object of the invention to provide a kind of compound in triazine class, such compound is used as dyestuff
Additive, can not only improve the solubility of reactive dye, prevent some dyestuffs from making dye because of degree of association increase after running into alkali, salt
Material is separated out from dye liquor；But also the disperse dyes sand milling time can be shortened, and improve and benefit is sanded, improve even after dyeing
Metachromia.
The technical solution adopted by the present invention is：
A kind of compound in triazine class, its structure such as formula（Ⅰ）It is shown：
Formula（Ⅰ）In：
R1~R4Each stand alone as H, C1~C4Alkyl, C1~C4Alkoxy or SO3M1；
R5It is H or SO2Y2；
Y1、Y2Each stand alone as-CH=CH2、-C2H4OSO3M2；
M1、M2Each stand alone as H or alkali metal, preferably H or Na；
X is halogen, preferably chlorine.
Additive of the present invention, can be with free acid（M1~M2It is hydrogen）Or salt（M1~M2It is alkali metal）Form deposit
, preferably existing in a salt form, described salt can be alkali metal salt（M1~M2It is alkali metal）, particularly preferably sodium salt（M1~
M2It is sodium）.
Preferably, the compound is one of following formula：
Compound of the present invention easily can be synthesized by mode well known to those skilled in the art, as according to conventional
Prepared by one contracting reaction and two contracting reaction methods, or prepared using following methods：
By formula（Ⅲ）Shown compound is beaten at being blended in 0 DEG C with frozen water, is subsequently adding formula（Ⅱ）Shown compound
Condensation reaction is carried out at 0~5 DEG C, reaction adds formula after terminating（Ⅳ）Shown compound, 40~45 DEG C, pH5.5~6
Under carry out consecutive condensation, finally filter be obtained formula（Ⅰ）Shown compound.
The invention further relates to described compound in triazine class as dye additive application.Concrete application method is as follows：
Dye composition add conven-tional adjuvants commercialization before or after, add the additive of ratio of the present invention carry out it is rear whole
Reason, or, by formula of the invention（Ⅰ-1）~（Ⅰ-15）One or more shown additive is matched somebody with somebody with conven-tional adjuvants with arbitrary proportion
The commercialization Final finishing processing of dyestuff is carried out after conjunction again, is contaminated again after preferably additive of the invention is coordinated with conven-tional adjuvants
The commercialization Final finishing processing of material.
The dye additive can be used to prepare commercial dye, the dye additive quality added in dye composition
Consumption is the 0.5~40% of dye composition quality.
The dye additive can also be used for mixing with auxiliary agent and prepare commercial dye, the dye added in dye composition
Feed additives are 0.5~50 with the mass ratio of auxiliary agent：50~99.5, dye additive and auxiliary agent quality sum and dyestuff chemical combination
The mass ratio of thing is 10~90：10~90；Described auxiliary agent is selected from mixture more than one of following or two of which：Naphthalene sulphur
Sour formaldehyde condensation products（Such as dispersing agent NNO）, alkyl naphthalene sulfonic acid formaldehyde condensation products（Such as Dispersant MF, methyl naphthalene sulfonic acid and formaldehyde condensation
Thing）, benzyl naphthalene sulfonic acid-formaldehyde condensation product（Such as dispersing agent CNF）, lignosulfonates such as sodium lignin sulfonate（Such as commercial dispersants
Reax83A、Reax85A）, glauber salt etc..
The dye additive is preferably 5~20 with the mass ratio of auxiliary agent：80~95.
The dye additive is preferably formula（Ⅰ-1）~（Ⅰ-15）One of or two of which more than mixture.
During the commercialization Final finishing of dyestuff, in addition to above-mentioned additive and conven-tional adjuvants are added, according to known in industry, also
PH buffer, dust-proofing agent, thickener, stabilizer, mould inhibitor etc. can be further added, if reactive dye can also add electricity
Solution matter salt, such as sodium chloride, potassium chloride and sodium sulphate, those of ordinary skill in the art can as needed carry out selection addition.
The beneficial effects are mainly as follows：Dye additive of the present invention is added during commercialization of dyes, can
To improve the solubility of reactive dye, prevent some dyestuffs from dyestuff is analysed from dye liquor because of degree of association increase after running into alkali, salt
Go out, success rate is once dyeed in raising；But also the disperse dyes sand milling time can be reduced, and improve and benefit is sanded, improve dyes
Level-dyeing property after color.
（Four）Brief description of the drawings
Fig. 1 is the compound mass spectrogram of the embodiment of the present invention 1.
（Five）Specific embodiment
With reference to specific embodiment, the present invention is described further, but protection scope of the present invention is not limited in
This：
Embodiment 1：
In there-necked flask, 20g Cyanuric Chlorides are added（Component A）After being beaten 30 minutes with frozen water at 0 DEG C, add
28.1g4（Beta-sulfuric ester ethyl sulfonyl）Aniline sodium salt（Component B）Condensation reaction is carried out at 0~5 DEG C, reaction is added after terminating
28.1g4（Beta-sulfuric ester ethyl sulfonyl）Aniline sodium salt（Component C）Consecutive condensation is carried out under 40~45 DEG C, pH5.5~6, instead
Suction filtration is obtained formula after should terminating（Ⅰ-1）Shown compound, its mass spectrogram is as shown in Figure 1.
Embodiment 2~15：
According to the method described in above-described embodiment 1, unlike, using raw material components A, B, C of equimolar amounts in table 1 below
Condensation reaction is carried out instead of component A, B in embodiment 1, C respectively, additive of the present invention can be obtained：
Table 1
Embodiment 16~38（The compounding of additive and conven-tional adjuvants）：
By additive of the present invention, after coordinating according to the ratio of table 2 below, collective effect is processed in the Final finishing of dyestuff
Process.
Table 2
Application Example 39：
Respectively by additive obtained in 20 grams of embodiments 1~15（The amount of giving money as a gift）, 100 grams of C.I. active blue 19s（The amount of giving money as a gift）Fill
Divide after being uniformly mixed, drying can obtain alkali resistant C.I. active blue 19 commercial dyes.
Application Example 40:
Respectively by additive obtained in 15 grams of embodiments 1~15（The amount of giving money as a gift）, 15 grams of glauber salt, 100 grams of C.I. reactive blues
19（The amount of giving money as a gift）After being thoroughly mixed uniformly, drying can obtain alkali resistant C.I. active blue 19 commercial dyes.
Application Example 41：
Respectively by additive obtained in 15 grams of embodiments 1~15（The amount of giving money as a gift）, 10 grams of glauber salt, 20 grams of Dispersant MFs, 100
Gram C.I. active blue 19s（The amount of giving money as a gift）After being thoroughly mixed uniformly, drying can obtain alkali resistant C.I. active blue 19s commodity dye
Material.
Application Example 42：
The complex of obtained additive and auxiliary agent in 100g above-described embodiments 16~38 is taken respectively（The amount of giving money as a gift）, with 250g
（The amount of giving money as a gift）C.I. after active blue 19 is sufficiently mixed uniformly, prepared alkali resistant C.I. active blue 19 commercial dyes are dried.
Comparative example 1：
Take 100g conven-tional adjuvants（Glauber salt）With 250g（The amount of giving money as a gift）C.I. spray drying is prepared general after active blue 19 mixing
Logical C.I. active blue 19 commercial dyes.
Application Example 43：
Respectively by additive obtained in 20 grams of embodiments 1~15（The amount of giving money as a gift）, 100 grams of C.I. Reactive Red 35s（The amount of giving money as a gift）Fill
Divide after being uniformly mixed, drying can obtain C.I. Reactive Red 35 commercial dyes.
Application Example 44:
Respectively by additive obtained in 15 grams of embodiments 1~15（The amount of giving money as a gift）, 15 grams of glauber salt, 100 grams of C.I. active reds
35（The amount of giving money as a gift）After being thoroughly mixed uniformly, drying can obtain C.I. Reactive Red 35 commercial dyes.
Application Example 45：
Respectively by additive obtained in 15 grams of embodiments 1~15（The amount of giving money as a gift）, 10 grams of glauber salt, 20 grams of Dispersant MFs, 100
Gram C.I. Reactive Red 35s（The amount of giving money as a gift）After being thoroughly mixed uniformly, drying can obtain C.I. Reactive Red 35 commercial dyes.
Application Example 46:
The complex of obtained additive and auxiliary agent in 100g above-described embodiments 16~38 is taken respectively（The amount of giving money as a gift）, with 200g
（The amount of giving money as a gift）C.I. prepared C.I. Reactive Red 35 commercial dyes are dried after Reactive Red 35 mixing.
Comparative example 2：
100g conven-tional adjuvants are taken respectively（Dispersant MF 30g, glauber salt 70g）With 200g（The amount of giving money as a gift）C.I. Reactive Red 35 is mixed
Dried after conjunction and common C.I. Reactive Red 35s commercial dye is obtained.
Solubility test：
The commercial dye that above-mentioned Application Example 39~46, comparative example 1~2 are obtained is by GB/T21879-2008
Described method tests its solubility, as a result see the table below 3.
Alkali resistance is tested：
In 100ml deionized waters, it is separately added into the above-mentioned Application Examples 39~46 of 10g, comparative example 1~2 and obtains
Commercial dye, adds 3g glauber salt, is warming up to 60 DEG C, and insulation 10min is allowed to dissolve.It is cooled to 25 DEG C, sampling.Use spotting method
Confirm on filter paper its it is complete it is molten after, stirring is lower, and to add 3ml mass fractions be 30% sodium hydroxide solution.Stirring is maintained, every 5min
Sampling, its precipitation situation is observed with spotting method, is had on filter paper to dyestuff substantially separating out, and calculates the alkaline-resisting time, is as a result seen
Table 3 below.
Salt And Alkali Tolerance is tested：
In 100ml deionized waters, be separately added into the above-mentioned Application Examples 39~46 of 2g, the dye that comparative example 1~2 obtains
Material product, is warming up to 60 DEG C, and insulation 20min is allowed to dissolve.Insulation sampling, stirring is lower to add 100ml saline solutions（Saline solution
In contain 20g/L sodium carbonate and 50g/L sodium sulphate）.At 60 DEG C, every 5min samplings, its dissolving situation is observed with spotting method,
Having obvious haloing on filter paper to dyestuff, the Salt And Alkali Tolerance time is calculated, as a result see the table below 3.
Table 3
| Sequence number | Commercial dye | Solubility（g/L） | The alkaline-resisting time（min） | The Salt And Alkali Tolerance time（min） |
| 1 | Application Example 39 | ＞ 340 | ＞ 80 | ＞ 60 |
| 2 | Application Example 40 | ＞ 345 | ＞ 75 | ＞ 50 |
| 3 | Application Example 41 | ＞ 350 | ＞ 80 | ＞ 60 |
| 4 | Application Example 42 | ＞ 350 | ＞ 80 | ＞ 60 |
| 5 | Comparative example 1 | ＜ 300 | ＜ 50 | ＜ 20 |
| 6 | Application Example 43 | ＞ 130 | ＞ 80 | ＞ 60 |
| 7 | Application Example 44 | ＞ 135 | ＞ 75 | ＞ 55 |
| 8 | Application Example 45 | ＞ 140 | ＞ 80 | ＞ 60 |
| 9 | Application Example 46 | ＞ 140 | ＞ 80 | ＞ 60 |
| 10 | Comparative example 2 | ＜ 60 | ＜ 40 | ＜ 30 |
Drawn by upper table 3, color additive can not only improve the solubility of reactive dye as obtained in the method for the invention,
But also can extend that reactive dye are alkaline-resisting, the Salt And Alkali Tolerance time.
Application Example 47:
The complex of obtained dye additive and auxiliary agent in 160g above-described embodiments 16~38 is taken respectively（The amount of giving money as a gift）, with
100g（The amount of giving money as a gift）C.I. the filter cake of disperse orange 61 is sanded in sand mill, and its dye particle is surveyed every 10min, to dye particle
1 μm of ＜, calculates its sand milling time, the results are shown in Table 4.
Comparative example 3:
Take 150g conven-tional adjuvants（Dispersant Reax85A）With 100g（The amount of giving money as a gift）C.I. the filter cake of disperse orange 61 enters in sand mill
Row is sanded, and its dye particle is surveyed every 10min, to 1 μm of dye particle ＜, calculates its sand milling time, the results are shown in Table 4.
Application Example 48:
The complex of obtained dye additive and auxiliary agent in 165g above-described embodiments 2~20 is taken respectively（The amount of giving money as a gift）, with
100g（The amount of giving money as a gift）C.I. the filter cake of disperse violet 93 is sanded in sand mill, and its dye particle is surveyed every 10min, to dye particle
1 μm of ＜, calculates its sand milling time, the results are shown in Table 4.
Comparative example 4:
Take 150g conven-tional adjuvants（Dispersant NNO）With 100g（Percentage amount）C.I. the filter cake of disperse violet 93 carries out sand in sand mill
Mill, its dye particle is surveyed every 10min, to 1 μm of dye particle ＜, calculates its sand milling time, the results are shown in Table 4.
| Sequence number | Dyestuff | The sand milling time（min） |
| 1 | Embodiment 47 | ＜ 90min |
| 2 | Comparative example 3 | ＞ 120min |
| 3 | Embodiment 48 | ＜ 60min |
| 4 | Comparative example 4 | ＞ 90min |
Drawn by upper table 3, the color additive as obtained in the method for the invention can reduce the sand milling time, improve and effect is sanded
Benefit, energy-saving benefit is notable.
Claims (5)
1. a kind of compound in triazine class as dye additive application, shown in the structure such as formula (I) of the compound in triazine class：
In formula (I)：
R1~R4Each stand alone as H, C1~C4Alkyl, C1~C4Alkoxy or SO3M1；
R5It is H or SO2Y2；
Y1、Y2Each stand alone as-CH=CH2、-C2H4OSO3M2；
M1、M2Each stand alone as H or alkali metal；
X is halogen；
The dye additive is used to prepare commercial dye added in dye composition, and the dye additive quality consumption is
The 0.5~40% of dye composition quality.
2. application as claimed in claim 1, it is characterised in that the dye additive is more than one of following or two of which
Mixture：
3. a kind of compound in triazine class as dye additive application, shown in the structure such as formula (I) of the compound in triazine class：
In formula (I)：
R1~R4Each stand alone as H, C1~C4Alkyl, C1~C4Alkoxy or SO3M1；
R5It is H or SO2Y2；
Y1、Y2Each stand alone as-CH=CH2、-C2H4OSO3M2；
M1、M2Each stand alone as H or alkali metal；
X is halogen；
The dye additive prepares commercial dye, the dye additive for mixing with auxiliary agent added in dye composition
It is 0.5~50 with the mass ratio of auxiliary agent：50~99.5, the quality of dye additive and auxiliary agent quality sum and dye composition
The ratio between be 10~90：10~90；Described auxiliary agent is selected from mixture more than one of following or two of which：Naphthalenesulfonateformaldehyde formaldehyde contracts
Compound, alkyl naphthalene sulfonic acid formaldehyde condensation products, benzyl naphthalene sulfonic acid-formaldehyde condensation product, lignosulfonates, glauber salt.
4. application as claimed in claim 3, it is characterised in that the dye additive is 5~20 with the mass ratio of auxiliary agent：
80~95.
5. the application as described in claim 3 or 4, it is characterised in that the dye additive for one of following or two of which with
On mixture：
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| CN104358119B (en) * | 2014-10-23 | 2016-09-21 | 广东溢达纺织有限公司 | A kind of anion-modified dose of response type and preparation method thereof |
| CN109266051B (en) * | 2018-08-21 | 2021-01-05 | 上海贝通色彩科技有限公司 | Water-based pigment self-dispersing system and preparation method thereof |
| KR20230132482A (en) * | 2020-12-23 | 2023-09-15 | 훈츠만 텍스타일 이펙츠 (스위처랜드) 게엠베하 | Use of reactive cross-linking agents for protein-containing matrices and improved processes for tanning and dyeing leather |
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| EP0118983A2 (en) * | 1983-02-11 | 1984-09-19 | Wool Development International Limited | Textile treatment |
| EP0175225A2 (en) * | 1984-09-15 | 1986-03-26 | Hoechst Aktiengesellschaft | Fibre-reactive triazine compounds, process for their preparation and their use |
| CN1210918A (en) * | 1997-06-04 | 1999-03-17 | 希巴特殊化学控股公司 | Crosslinking of cellulosic fibre materials |
| CN101824761A (en) * | 2010-03-29 | 2010-09-08 | 河南工程学院 | Dyeing method |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63207864A (en) * | 1987-02-24 | 1988-08-29 | Sumitomo Chem Co Ltd | Phthalocyanine compound and dyeing or printing with said compound |
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| EP0118983A2 (en) * | 1983-02-11 | 1984-09-19 | Wool Development International Limited | Textile treatment |
| EP0175225A2 (en) * | 1984-09-15 | 1986-03-26 | Hoechst Aktiengesellschaft | Fibre-reactive triazine compounds, process for their preparation and their use |
| CN1210918A (en) * | 1997-06-04 | 1999-03-17 | 希巴特殊化学控股公司 | Crosslinking of cellulosic fibre materials |
| CN101824761A (en) * | 2010-03-29 | 2010-09-08 | 河南工程学院 | Dyeing method |
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