CN1861695A - Yellow ozo dye mixture and its use - Google Patents
Yellow ozo dye mixture and its use Download PDFInfo
- Publication number
- CN1861695A CN1861695A CN 200610082904 CN200610082904A CN1861695A CN 1861695 A CN1861695 A CN 1861695A CN 200610082904 CN200610082904 CN 200610082904 CN 200610082904 A CN200610082904 A CN 200610082904A CN 1861695 A CN1861695 A CN 1861695A
- Authority
- CN
- China
- Prior art keywords
- dyestuff
- formula
- parts
- dye mixture
- azo dye
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 34
- 239000000975 dye Substances 0.000 claims abstract description 99
- 239000000987 azo dye Substances 0.000 claims abstract description 12
- 239000000463 material Substances 0.000 claims description 29
- 238000004043 dyeing Methods 0.000 claims description 21
- -1 β-chloroethyl Chemical group 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- 229920002554 vinyl polymer Polymers 0.000 claims description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
- 239000000835 fiber Substances 0.000 claims description 4
- 229910019142 PO4 Inorganic materials 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 239000010452 phosphate Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000002657 fibrous material Substances 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 22
- 150000001875 compounds Chemical class 0.000 description 19
- 239000000243 solution Substances 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 15
- 238000002360 preparation method Methods 0.000 description 15
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 14
- 239000012954 diazonium Substances 0.000 description 13
- 150000001989 diazonium salts Chemical class 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 238000006193 diazotization reaction Methods 0.000 description 12
- 239000004744 fabric Substances 0.000 description 12
- 235000010288 sodium nitrite Nutrition 0.000 description 11
- 238000000034 method Methods 0.000 description 10
- 238000005859 coupling reaction Methods 0.000 description 9
- 238000007639 printing Methods 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 229920000742 Cotton Polymers 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 238000010009 beating Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 238000013019 agitation Methods 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 150000008107 benzenesulfonic acids Chemical class 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 5
- 238000006482 condensation reaction Methods 0.000 description 5
- 238000010792 warming Methods 0.000 description 5
- 101100118680 Caenorhabditis elegans sec-61.G gene Proteins 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000003599 detergent Substances 0.000 description 4
- 235000017550 sodium carbonate Nutrition 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 239000001043 yellow dye Substances 0.000 description 4
- ZNXSFVXZQBETRJ-UHFFFAOYSA-N (3-aminophenyl)urea Chemical compound NC(=O)NC1=CC=CC(N)=C1 ZNXSFVXZQBETRJ-UHFFFAOYSA-N 0.000 description 3
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- 238000001514 detection method Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000000661 sodium alginate Substances 0.000 description 3
- 235000010413 sodium alginate Nutrition 0.000 description 3
- 229940005550 sodium alginate Drugs 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 230000008719 thickening Effects 0.000 description 3
- 238000009941 weaving Methods 0.000 description 3
- 229920003043 Cellulose fiber Polymers 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- QQNXPCCFPQRLMK-UHFFFAOYSA-N S(O)(O)(=O)=O.OCCS(=O)(=O)CCO Chemical compound S(O)(O)(=O)=O.OCCS(=O)(=O)CCO QQNXPCCFPQRLMK-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 238000009980 pad dyeing Methods 0.000 description 2
- 229920006306 polyurethane fiber Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 239000001488 sodium phosphate Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- LIBWRRJGKWQFSD-UHFFFAOYSA-M sodium;2-nitrobenzenesulfonate Chemical compound [Na+].[O-][N+](=O)C1=CC=CC=C1S([O-])(=O)=O LIBWRRJGKWQFSD-UHFFFAOYSA-M 0.000 description 2
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 2
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 1
- ZMCHBSMFKQYNKA-UHFFFAOYSA-N 2-aminobenzenesulfonic acid Chemical compound NC1=CC=CC=C1S(O)(=O)=O ZMCHBSMFKQYNKA-UHFFFAOYSA-N 0.000 description 1
- 244000198134 Agave sisalana Species 0.000 description 1
- 235000011624 Agave sisalana Nutrition 0.000 description 1
- 240000008564 Boehmeria nivea Species 0.000 description 1
- 240000000491 Corchorus aestuans Species 0.000 description 1
- 235000011777 Corchorus aestuans Nutrition 0.000 description 1
- 235000010862 Corchorus capsularis Nutrition 0.000 description 1
- 238000006424 Flood reaction Methods 0.000 description 1
- 241000219146 Gossypium Species 0.000 description 1
- 240000006240 Linum usitatissimum Species 0.000 description 1
- 235000004431 Linum usitatissimum Nutrition 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 239000004902 Softening Agent Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 238000005097 cold rolling Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- WBZKQQHYRPRKNJ-UHFFFAOYSA-L disulfite Chemical compound [O-]S(=O)S([O-])(=O)=O WBZKQQHYRPRKNJ-UHFFFAOYSA-L 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- AJDUTMFFZHIJEM-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000012716 precipitator Substances 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 235000011008 sodium phosphates Nutrition 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 1
- 235000019801 trisodium phosphate Nutrition 0.000 description 1
- ZNRSXPDDVNZGEN-UHFFFAOYSA-K trisodium;chloride;sulfate Chemical compound [Na+].[Na+].[Na+].[Cl-].[O-]S([O-])(=O)=O ZNRSXPDDVNZGEN-UHFFFAOYSA-K 0.000 description 1
- 238000004148 unit process Methods 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
Landscapes
- Coloring (AREA)
Abstract
A yellow azodye mixture includes the dyestuff of the general form (1), (2) and (3) which the weight ratio is 55-40:40-50:5-10. The giving color dose is higher than the coloration of the single dyestuff or the average of the tax stamp after dying the fiber material or the tax stamp; and the effect is better than the traditional active yellow dyestuff.
Description
Technical field
The present invention relates to a kind of Yellow azo dye mixture and uses thereof, belong to dye field.
Background technology
No matter single dyestuff, or mixture dyestuff is dyeing to filamentary material or during stamp, and dyestuff is for fiber, the most important thing is that good tinctorial yield can be arranged, avidity and good degree of fixation.Usually, when filamentary material being implemented dyeing or stamp with two or more dye mixture, resulting tinctorial yield is adding of single dyestuff tinctorial yield and mean value, and the tinctorial yield that is to say dye mixture will be lower than the tinctorial yield of the sort of single dyestuff of higher one or more of tinctorial yield wherein; In present stage, replace homogencous dyes with raising dyeing affinity and degree of fixation from mixing colouring agent, thereby improve dyeing quality, be one of research direction of dealer.
Summary of the invention
The present invention is a kind of yellow dyes mixture, and after utilizing it to filamentary material dyeing or stamp, its tinctorial yield is adding and mean value behind single dyeing or the stamp in the mixture; Its Color is better than the Color of traditional active yellow dye.
The feature of yellow dyes mixture of the present invention is: it comprises the dyestuff of general formula (1), the dyestuff of general formula (2) and the dyestuff of general formula (3), and their ratios of weight and number in the mixture dyestuff are 55-40: 40-50: 5-10,
Wherein:
R
1Be hydrogen atom, C
1-C
4Alkyl, C
1-C
4Alkoxyl group or-SO
3H;
R
2Be amino or C
1-C
4Alkyl
X is-NHCN ,-OH,
-F ,-Cl or-Br;
M is the 0-5 numeral, and n, w are the numeral of 0-2;
D
1, D
2, D
3, D
4Be formula (4) or formula (5) group;
In the formula:
R
3(0-3) and R
4(0-3) for 0-3 be same to each other or different to each other be selected from hydrogen atom ,-SO
3H ,-OH ,-COOH ,-F ,-Cl ,-Br, C
1-C
4Alkyl or C
1-C
4Alkoxyl group;
P and q are the numeral of 0-2;
Z
1And Z
2Be respectively (6a), (6b), (6c) or (6d) group;
-SO
2-Y (6a) -CONH-(CH
2)r-SO
2-Y (6b)
-NHCOCH(Hal)CH
2Hal (6c) -NHCOCH(Hal)＝CH
2 (6d)
R is the numeral of 0-5;
Hal be halogen as :-F ,-Cl ,-Br, preferred-Br;
Y be vinyl β-chloroethyl, β-bromotrifluoromethane, β-acetoxyl ethyl, β-sulfato ethyl, beta-phenoxy ethyl, β-phosphate ethyl or-CH
2-CH
2-U group, U are leaving groups, be can be separated under alkaline condition group, can be as :-F ,-Cl ,-Br ,-OSO
3H ,-SSO
3H ,-OCO-CH
3,-OPO
3H
2,-OCO-C
6H
5,-OSO
2-C
1-C
4Alkyl or-OSO
2-N-(C
1-C
4Alkyl), preferred U be-Cl ,-OSO
3H ,-OPO
3H
2Or-OCO-C
6H
5, especially preferably-OSO
3H;
Preferred Y is β-sulfato ethyl or vinyl.
Preferred R
1Be hydrogen atom, R
2Be amino.
Preferred X is-F or-Cl.
Preferred m is 3, and n, w are 1.
Work as D
1, D
2, D
3, D
4When being formula (4) group, wherein p is 1,
R
3(0-3) for 0-3 mutually the same or inequality be selected from hydrogen atom ,-SO
3H ,-OH ,-COOH ,-F ,-Cl ,-Br, C
1-C
4Alkyl or C
1-C
4Alkoxyl group.
Z
1Be (6a), (6b), (6c) or (6d) group,
-SO
2-Y (6a) -CONH-(CH
2)r-SO
2-Y (6b)
-NHCOCH(Hal)CH
2Hal (6c) -NHCOCH(Hal)＝CH
2 (6d)
Wherein:
R is the numeral of 0-5, preferred 2;
Hal is a halogen, as :-F ,-Cl ,-Br, preferred-Br;
Y is vinyl, β-chloroethyl, β-bromotrifluoromethane, β-acetoxyl ethyl, β-sulfato ethyl, beta-phenoxy ethyl or β-phosphate ethyl, preferred β-sulfato ethyl or vinyl.
Work as D
1, D
2, D
3, D
4, when being formula (5) group,
Wherein:
R
4(0-3) be hydrogen atom ,-SO
3H, C
1-C
4Alkyl or C
1-C
4Alkoxyl group;
Z
2(q) be (6a) group:
-SO
2-Y (6a)
Y is β-sulfato ethyl;
Q is 1 numeral.
The present invention relates to the preparation method of formula (1) dyestuff, this method comprises the following compound that uses about 1 molar equivalent under every kind of situation:
D
1-NH
2 (10)
The compound of formula (7) was pulled an oar 1 hour in an amount of water, adding hydrochloric acid stirred after 20 minutes, be cooled to 0-10 ℃ with ice, drip 30% sodium nitrite solution then and under agitation carry out diazotization, remain T=0-10 ℃ in the whole diazo process, and keep hydrochloric acid and Sodium Nitrite abundance, can obtain the diazonium salt of formula (7) compound after 2 hours, subsequently formula (7) diazonium salt is joined in formula (8) compound through abundant making beating, and keep PH=3-5, T=10-18 ℃ coupled reaction takes place, up to can not detecting diazonium salt for reacting completely, obtain a kind of conjugates, conjugates is joined formula (9) compound that grinds through abundant ice; Control T=0-15 ℃, PH=2-5 condensation reaction take place, after 4 hours in system adding formula (10) compound; Control T=20-60 ℃, condensation reaction for the second time takes place in PH=2-5, can obtain the dyestuff of general molecular formula (1),
Certainly, change synthetic middle unit process order, can obtain the dyestuff of general molecular formula (1) equally.
The present invention relates to the preparation method of formula (2) dyestuff, this method comprises the following compound that uses about 1 molar equivalent under every kind of situation:
D
2-NH
2 (11) D
3-NH
2 (12)
The compound of formula (11) and formula (12) is done conventional diazotization reaction in the manner described above, then with through the abundant compound generation coupled reaction of the formula (13) of making beating, up to can not detecting diazonium salt, can obtain the dyestuff of general molecular formula (2) for reacting completely:
The preparation method and formula (2) dyestuff of formula of the present invention (3) dyestuff are basic identical, formula (14) compound is done done conventional coupled reaction with formula (15) compound after the conventional diazotization reaction and can obtain.
D
4-NH
2 (14)
The mol ratio of formula (14) compound and formula (15) compound is 1: 1
The preparation of mixture dyestuff of the present invention, be with formula (1) dyestuff, formula (2) dyestuff and formula (3) dyestuff in above-mentioned ratio through mechanically mixing fully.
The compound that the present invention is defined as formula (7) has:
The compound that the present invention is defined as formula (8) has:
The compound that the present invention is defined as formula (9) has:
The compound that the present invention is defined as formula (10), (11), (12) and (14) has:
The compound that the present invention is defined as formula (13) and formula (15) has:
The dyestuff of general molecular formula of the present invention (1), (2), (3) can adopt spray method, the precipitator method and filter press technique and obtains.Mixture dyestuff of the present invention can obtain the dyestuff of formula (1), (2), (3) 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 the auxiliary agent that some are commonly used, as levelling agent, dyeing accelerant, interfacial agent, dispersion agent etc., sometimes for different purposes filamentary material is dyeed or during stamp, can also add some functional aids, as softening agent, dust-proofing agent, fire retardant and static inhibitor.
The dyestuff of formula of the present invention (1), (2), (3) contains an anion-radicals at least, as sulfonic group, for convenience of explanation, form with free acid in specification sheets is represented, but all to be form with soluble salt in the finished product dyestuff exist for they, as lithium salts, potassium or sodium salt, especially the existence form with sodium salt is the best.
Dye mixture of the present invention is applicable to dyeing or the various filamentary materials of stamp, as contain hydroxyl or contain amino filamentary material, the filamentary material that contains hydroxyl has cotton, jute, flax, ramie, sisal hemp and regenerated cellulose fibre, containing amino filamentary material has: silk, wool, leather, tynex and polyurethane fiber, the blended fabric of all right printing cellulose fibres and tynex or polyurethane fiber.
Above-mentioned filamentary material existence form can be: fiber, yarn, woven fabrics or knitted fabrics.
The normal dyeing method that dye mixture of the present invention is suitable for has: dip-dye, dye gigging, pad dyeing, cold rolling heap.The preferred dip-dye and pad dyeing, suitable conventional printing method has: rotary printing, PLATE SCREAM PRINTING, ROTARY SCREAM PRINTING, preferred rotary printing.Usually dyestuff is made into the aqueous solution with salt (sodium-chlor, sodium sulfate), add under the condition of alkali (sodium hydroxide, yellow soda ash, sodium bicarbonate, sodium phosphate), heating (T≤60 ℃) and dye, dyestuff and thickening material (sodium alginate, ether of cellulose), solubility promoter (urea), reserve salt (-nitrobenzene sodium sulfonate) etc. are made into printing paste carry out stamp, remove loose colour with conventional dyeing and finishing aftertreatment then.
In sum, dye mixture of the present invention is dyeing to filamentary material or during stamp, dyestuff has very high tinctorial yield, can react well with filamentary material, formed dyestuff-fiber key has very high acid-fast alkali-proof stability, thereby staining power is also very high, and dyeing quality improves, than using single dyestuff to be significantly improved on using.
Embodiment
In the following example, part is meant weight part, and temperature is with a degree centigrade expression, relation between weight part and the parts by volume and gram with cubic centimetre between relation identical.
Embodiment 1, the dyestuff preparation:
38.3 parts of 2-naphthylamines-3.6.8-trisulfonic acids are added hydrochloric acid and are cooled to 6 ℃ with ice after pulling an oar 1 hour, drip 30% sodium nitrite solution then and under constantly stirring, diazotization reaction is taking place, add 18.75 parts of warps 3-amino-phenylurea of fully pulling an oar after 2 hours, keep T=14 ℃, pH=4.5 carries out coupled reaction, up to can not detecting diazonium salt for reacting completely, obtain a kind of conjugates, subsequently conjugates being joined 13.6 parts of warps in 30 minutes fully ices in the cyanogen urea acyl fluorides of mill condensation reaction takes place, keep T=11.5 ℃, pH=3.5 reaction 4 hours, in system, add 28.13 parts of right-(beta-hydroxyethyl sulfone sulfate) aniline at last, keep T=45 ℃, pH=3.5 reaction 4 hours, can obtain the dyestuff (1-1) of general molecular formula (1), this dyestuff can be printed and dyed into filamentary material qualified yellow.
Embodiment 2, the dyestuff preparation:
38.3 parts of 2-naphthylamines-3.6.8-trisulfonic acids are added hydrochloric acid and are cooled to 6 ℃ with ice after pulling an oar 1 hour, drip 30% sodium nitrite solution then and under constantly stirring, diazotization reaction is taking place, add 18.75 parts of warps 3-amino-phenylurea of fully pulling an oar after 2 hours, keep T=14 ℃, pH=4.5 carries out coupled reaction, up to can not detecting diazonium salt for reacting completely, obtain a kind of conjugates, subsequently conjugates being joined 18.45 parts of warps in 30 minutes fully ices in the cyanuric chloride of mill condensation reaction takes place, keep T=11.5 ℃, pH=3.5 reaction 4 hours, in system, add 28.13 parts of right-(beta-hydroxyethyl sulfone sulfate) aniline at last, keep T=45 ℃, pH=3.5 reaction 4 hours, can obtain the dyestuff (1-2) of general molecular formula (1), this dyestuff can be printed and dyed into filamentary material qualified yellow.
Embodiment 3, the dyestuff preparation:
38.3 parts of 2-naphthylamines-3.6.8-trisulfonic acids are added hydrochloric acid and are cooled to 6 ℃ with ice after pulling an oar 1 hour, drip 30% sodium nitrite solution then and under constantly stirring, diazotization reaction is taking place, add 18.75 parts of warps 3-amino-phenylurea of fully pulling an oar after 2 hours, keep T=14 ℃, pH=4.5 carries out coupled reaction, up to can not detecting diazonium salt for reacting completely, obtain a kind of conjugates, subsequently conjugates being joined 13.6 parts of warps in 30 minutes fully ices in the cyanogen urea acyl fluorides of mill condensation reaction takes place, keep T=11.5 ℃, pH=3.5 reaction 4 hours, in system, add 29.73 parts of right-(beta-hydroxyethyl sulfone sulfate) ortho-aminophenols at last, keep T=45 ℃, pH=3.5 reaction 4 hours, can obtain the dyestuff (1-3) of general molecular formula (1), this dyestuff can be printed and dyed into filamentary material qualified yellow.
Embodiment 4-10, the dyestuff preparation:
Press the synthetic method of embodiment 1-3, choose the intermediate that is defined as formula (7), (8), (9), (10) by the present invention, can obtain the dyestuff of following general molecular formula (1) equally, they can both print and dye into filamentary material qualified yellow.
Embodiment 11, the dyestuff preparation:
56.2 parts of right-(beta-hydroxyethyl sulfone sulfate) aniline making beating are added hydrochloric acid and cool to 5 ℃ with ice after 1 hour, the sodium nitrite solution of adding 30% is under agitation made diazotization reaction and is added 18.8 parts of 2.4-diamino benzene sulfonic acids after 2 hours, keep T=7.5 ℃, the pH=3 reaction is after 2 hours, the pH value is transferred to pH=6.5 with 30% sodium hydroxide, being reacted to detection, not go out diazonium salt be reaction end, can obtain the dyestuff (2-1) of general molecular formula (2), this dyestuff can be printed and dyed into filamentary material qualified yellow.
Embodiment 12, the dyestuff preparation:
56.2 parts of right-(beta-hydroxyethyl sulfone sulfate) aniline making beating are added hydrochloric acid and cool to 5 ℃ with ice after 1 hour, the sodium nitrite solution of adding 30% is under agitation made diazotization reaction and is added 1 8.8 parts of 3.5-diamino benzene sulfonic acids after 2 hours, keep T=7.5 ℃, the pH=3 reaction is after 2 hours, the pH value is transferred to pH=6.5 with 30% sodium hydroxide, being reacted to detection, not go out diazonium salt be reaction end, can obtain the dyestuff (2-2) of general molecular formula (2), this dyestuff can be printed and dyed into filamentary material qualified yellow.
Embodiment 13, the dyestuff preparation:
With between 56.2 parts-making beating of (beta-hydroxyethyl sulfone sulfate) aniline adds hydrochloric acid and cools to 50-10 ℃ with icing after 1 hour, the sodium nitrite solution of adding 30% is under agitation made diazotization reaction and is added 18.8 parts of 3.5-diamino benzene sulfonic acids after 2 hours, keep T=12 ℃, the pH=.3 reaction is after 2 hours, the pH value is transferred to pH=6.5 with 30% sodium hydroxide, being reacted to detection, not go out diazonium salt be reaction end, can obtain the dyestuff (2-3) of general molecular formula (2), this dyestuff can be printed and dyed into filamentary material qualified yellow.
Embodiment 14-20, the dyestuff preparation:
According to the mode of embodiment 11-13, select the compound that is defined as formula (11), (12), (13) by the present invention for use, also can obtain the dyestuff of following general molecular formula (2), they can both print and dye into filamentary material qualified yellow.
Embodiment 21, the dyestuff preparation:
28.1 parts of right-(beta-hydroxyethyl sulfone sulfate) aniline making beating are added hydrochloric acid and cool to 5 ℃ with ice after 1 hour, the sodium nitrite solution of adding 30%, under agitation make diazotization reaction and add 18.8 parts of 2.4-diamino benzene sulfonic acids after 2 hours, keep T=12.5 ℃, pH=3.5 carries out coupled reaction, up to can not detecting diazonium salt is reaction end, can obtain the dyestuff (3-1) of general molecular formula (3), and this dyestuff can be printed and dyed into filamentary material qualified yellow.
Embodiment 22, the dyestuff preparation:
With between 28.1 parts-making beating of (beta-hydroxyethyl sulfone sulfate) aniline adds hydrochloric acid and cools to 5 ℃ with icing after 1 hour, the sodium nitrite solution of adding 30%, under agitation make diazotization reaction and add 18.8 parts of 2.4-diamino benzene sulfonic acids after 2 hours, keep T=12.5 ℃, pH=3.5 carries out coupled reaction, up to can not detecting diazonium salt is reaction end, can obtain the dyestuff (3-2) of general molecular formula (3), and this dyestuff can be printed and dyed into filamentary material qualified yellow.
Embodiment 23, the dyestuff preparation:
36.1 parts of right-(beta-hydroxyethyl sulfone sulfate) aniline ortho-sulfonic acid making beating are added hydrochloric acid and cool to 5 ℃ with ice after 1 hour, the sodium nitrite solution of adding 30%, under agitation make diazotization reaction and add 18.8 parts of 2.4-diamino benzene sulfonic acids after 2 hours, keep T=12.5 ℃, pH=3.5 carries out coupled reaction, up to can not detecting diazonium salt is reaction end, can obtain the dyestuff (3-3) of general molecular formula (3), and this dyestuff can be printed and dyed into filamentary material qualified yellow.
According to the foregoing description mode, choose the dyestuff that the compound that is defined as formula (11), (12), (13), (14), (15) by the present invention can obtain following general molecular formula (3), they can both print and dye into filamentary material qualified yellow.
Embodiment 24, dyeing:
2.2 parts of dyestuffs (1-1), 1.6 parts of dyestuffs (2-1), 0.2 part of dyestuff (3-1) are dissolved in 800 parts of water, after fully stirring, the sodium chloride solution that in this mixture dye liquor, adds 1000 parts of 200g/l, 200 parts of cotton fabrics are put into dye bath, be warming up to 60 ℃ with 1 ℃ of/minute intensification speed after, add the sodium carbonate solution of 200 parts of 20g/l, and under this temperature, dyeed 1 hour, then the dyeing and weaving thing is carried out rinsing, under boiling, soaped 15 minutes the post rinse drying with non-ionic detergent.
Embodiment 25, dyeing:
With 2.2 parts of dyestuffs (1-2), 1.6 part dyestuff (2-2), 0.2 a part dyestuff (3-2) is dissolved in 800 parts of water after abundant stirring, in this mixture dye liquor, add sodium chloride solution with 200 parts of 200g/l, 200 parts of cotton fabrics are put in the dye bath, when being warming up to 35 ℃ with 1 ℃/minute heat-up rate, add the sodium carbonate solution of 200 parts of 20g/l, and under this temperature, kept 10 minutes, in 25 minutes, be warming up to 60 ℃ then, and under this temperature, kept 30 minutes, then the dyeing and weaving thing is carried out rinsing, under boiling, soaped 15 minutes the post rinse drying with non-ionic detergent.
Embodiment 26, dyeing:
4.4 parts of dyestuffs (1-3), 3.2 parts of dyestuffs (2-3), 0.4 part of dyestuff (3-3) are dissolved in 800 parts of water after fully stirring, the metabisulfite solution that in this mixture dye liquor, adds 1500 parts of 150g/l, 200 parts of cotton fabrics are put in the dye bath, when being warming up to 25 ℃ with 1 ℃/minute heat-up rate, add the trisodium phosphate solution of 100 parts of 150g/l, be warming up to 60 ℃ then, and under this temperature, kept 1 hour, then the dyeing and weaving thing is carried out rinsing, under boiling, soaped 15 minutes the post rinse drying with non-ionic detergent.
Embodiment 27, dyeing:
2.2 parts of dyestuffs (1-1), 1.6 parts of dyestuffs (2-2), 0.2 part of dyestuff (3-3) are dissolved in 50 parts of water after fully stirring, with this solution impregnation cotton fabric, the pick-up that makes cotton fabric is 80% oven dry then, then in room temperature with containing the sodium carbonate solution of 20g/l and the sodium chloride solution of 200g/l floods this fabric, making the pick-up of fabric with roll roll compacting then is 80%, the fabric that dyed is 30 seconds post rinsings of decatize in 100-102 ℃ saturation water steaming, soaped 15 minutes with non-ionic detergent under boiling, post rinse is also dry.
Embodiment 28, stamp:
By quick stirring, with 2.2 parts of dyestuffs (1-1), 1.6 parts of dyestuffs (2-1), 0.2 part of dyestuff (3-1) be sprinkled into 100 parts contain 50 part 5% sodium alginate thickening material, 27.8 parts of water, 20 parts of urea, between 1 part-magma of nitrobenzene sodium sulfonate and 1.2 parts of sodium bicarbonates in, with the printing paste that according to said method makes cotton fabric is carried out stamp, use 100-102 ℃ saturated vapor decatize 2-3 minute then, rinsing then, can under boiling, soap if desired, once more rinsing and dry.
Embodiment 29, stamp:
By quick stirring, with 4.4 parts of dyestuffs (1-2), 3.2 parts of dyestuffs (2-2), 0.4 part of dyestuff (3-2), be sprinkled into 300 parts contain 150 part 5% sodium alginate thickening material, 109.5 parts of water, 30 parts of urea, between 3 parts-magma of nitrobenzene sodium sulfonate and 7.5 parts of sodium bicarbonates in, with the printing paste that according to said method makes cotton fabric is carried out stamp, use 102 ℃ saturated vapor decatize 5 minutes then, rinsing then, can soap under boiling if desired, post rinse is also dry.
The performance index that yellow dyes mixture of the present invention and traditional reactive yellow 4RN implement dyeing or stamp to filamentary material detect contrast table:
Claims (9)
1. Yellow azo dye mixture, it is characterized in that: it comprises the dyestuff of general formula (1), the dyestuff of general formula (2) and the dyestuff of general formula (3), and their ratio of weight and number is 55-40: 40-50: 5-10,
In the formula:
R
1Be hydrogen atom, C
1-C
4Alkyl, C
1-C
4Alkoxyl group or-SO
3H;
R
2Be amino or C
1-C
4Alkyl;
X is-NHCN ,-OH,
-F ,-Cl or-Br;
M is the 0-5 numeral, and n, w are the numeral of 0-2;
D
1, D
2, D
3, D
4Be formula (4) or formula (5) group;
Wherein:
R
3(0-3) and R
4(0-3) for 0-3 be same to each other or different to each other be selected from hydrogen atom ,-SO
3H ,-OH ,-COOH ,-F ,-Cl ,-Br, C
1-C
4Alkyl or C
1-C
4Alkoxyl group;
P and q are the numeral of 0-2;
Z
1And Z
2Be respectively (6a), (6b), (6c) or (6d) group;
-SO
2-Y (6a) -CONH-(CH
2)
r-SO
2-Y (6b)
-NHCOCH(Hal)CH
2Hal (6c) -NHCOCH(Hal)＝CH
2 (6d)
R is the numeral of 0-5;
Hal be halogen as :-F ,-Cl or-Br, preferred-Br;
Y be vinyl, β-chloroethyl, β-bromotrifluoromethane, β-acetoxyl ethyl, β-sulfato ethyl, beta-phenoxy ethyl, β-phosphate ethyl or-CH
2-CH
2-U group, U are leaving groups, be can be separated under alkaline condition group, be :-F ,-Cl ,-Br ,-OSO
3H ,-SSO
3H ,-OCO-CH
3,-OPO
3H
2,-OCO-C
6H
5,-OSO
2-C
1-C
4Alkyl or-OSO
2-N-(C
1-C
4Alkyl), preferred U be-Cl ,-OSO
3H ,-OPO
3H
2Or-OCO-C
6H
5, especially preferably-OSO
3H;
Preferred Y is β-sulfato ethyl or vinyl.
2. Yellow azo dye mixture according to claim 1 is characterized in that: described R
1Be hydrogen atom, R
2Be amino.
3. Yellow azo dye mixture according to claim 1 is characterized in that: described X for-F or-Cl.
4. Yellow azo dye mixture according to claim 1 is characterized in that: described m is 3, and n, w are 1.
5. according to the described Yellow azo dye mixture of claim 1, it is characterized in that: described D
1, D
2, D
3, D
4, be formula (5) group
Wherein:
R
4(O-3) be hydrogen atom ,-SO
3H, C
1-C
4Alkyl or C
1-C
4Alkoxyl group;
Z
2(q) be (6a) group:
-SO
2-Y (6a)
Y is β-sulfato ethyl;
Q is 1 numeral.
6. Yellow azo dye mixture according to claim 1 is characterized in that: it is the mixture of following formula (1-2), (2-1), (3-1) dyestuff,
7. Yellow azo dye mixture according to claim 1 is characterized in that: it is the mixture of following formula (1-1), (2-2), (3-2) dyestuff,
8. Yellow azo dye mixture according to claim 1 is characterized in that: it is the mixture of following formula (1-3), (2-3), (3-3) dyestuff,
9. according to the purposes of the described Yellow azo dye mixture of claim 1-8, it is characterized in that: described mixture is applicable to the dyeing or the stamp of the filamentary material that contains cellulosic fibre material, hydroxyl and amino.
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|---|---|---|---|
| CNB2006100829049A CN100412140C (en) | 2006-06-19 | 2006-06-19 | Yellow ozo dye mixture and its use |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2006100829049A CN100412140C (en) | 2006-06-19 | 2006-06-19 | Yellow ozo dye mixture and its use |
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| CN100412140C CN100412140C (en) | 2008-08-20 |
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ID=37389230
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|---|---|---|---|
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Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008095802A3 (en) * | 2007-02-06 | 2009-03-19 | Dystar Textilfarben Gmbh & Co | Mixtures of fibre-reactive azo dyes |
| CN101307190B (en) * | 2007-05-18 | 2011-05-25 | 明德国际仓储贸易(上海)有限公司 | Yellow chemically-reactive dye combinations |
| CN102311663A (en) * | 2011-07-07 | 2012-01-11 | 天津德凯化工股份有限公司 | Nylon yellow reactive dye and preparation method thereof |
| CN102311661A (en) * | 2011-07-07 | 2012-01-11 | 天津德凯化工股份有限公司 | Yellow reactive dye and preparation method thereof |
| CN102311662A (en) * | 2011-07-07 | 2012-01-11 | 天津德凯化工股份有限公司 | Yellow reactive dye for nylon and preparation method thereof |
| CN102391672A (en) * | 2011-07-07 | 2012-03-28 | 天津德凯化工股份有限公司 | Yellow active dye |
| CN102453348A (en) * | 2010-10-28 | 2012-05-16 | 上海雅运纺织化工股份有限公司 | Reactive yellow compound and application thereof |
| CN102924348A (en) * | 2012-09-25 | 2013-02-13 | 天津德凯化工股份有限公司 | Reactive dye and intermediate thereof |
| CN104350107A (en) * | 2012-06-15 | 2015-02-11 | 亨斯迈先进材料（瑞士）有限公司 | Fibre-reactive dyes, their preparation and their use |
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Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2001289722A1 (en) * | 2000-07-25 | 2002-02-05 | Dystar Textilfarben Gmbh And Co. Deutschland Kg | Dye mixtures of fiber reactive azo dyes and use therof for dyeing material containing hydroxy- and/or carboxamido groups |
-
2006
- 2006-06-19 CN CNB2006100829049A patent/CN100412140C/en not_active Expired - Fee Related
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008095802A3 (en) * | 2007-02-06 | 2009-03-19 | Dystar Textilfarben Gmbh & Co | Mixtures of fibre-reactive azo dyes |
| CN101307190B (en) * | 2007-05-18 | 2011-05-25 | 明德国际仓储贸易(上海)有限公司 | Yellow chemically-reactive dye combinations |
| DE102008024210B4 (en) * | 2007-05-18 | 2017-01-26 | Everlight Usa, Inc. | Yellow reactive dye composition |
| CN102453348A (en) * | 2010-10-28 | 2012-05-16 | 上海雅运纺织化工股份有限公司 | Reactive yellow compound and application thereof |
| CN102453348B (en) * | 2010-10-28 | 2013-12-04 | 上海雅运纺织化工股份有限公司 | Reactive yellow compound and application thereof |
| CN102311661A (en) * | 2011-07-07 | 2012-01-11 | 天津德凯化工股份有限公司 | Yellow reactive dye and preparation method thereof |
| CN102391672A (en) * | 2011-07-07 | 2012-03-28 | 天津德凯化工股份有限公司 | Yellow active dye |
| CN102311662A (en) * | 2011-07-07 | 2012-01-11 | 天津德凯化工股份有限公司 | Yellow reactive dye for nylon and preparation method thereof |
| CN102311663A (en) * | 2011-07-07 | 2012-01-11 | 天津德凯化工股份有限公司 | Nylon yellow reactive dye and preparation method thereof |
| CN104350107A (en) * | 2012-06-15 | 2015-02-11 | 亨斯迈先进材料（瑞士）有限公司 | Fibre-reactive dyes, their preparation and their use |
| KR20150033650A (en) * | 2012-06-15 | 2015-04-01 | 훈츠만 어드밴스트 머티리얼스(스위처랜드) 게엠베하 | Fibre-reactive dyes, their preparat1on and their use |
| CN104350107B (en) * | 2012-06-15 | 2018-01-05 | 亨斯迈先进材料（瑞士）有限公司 | Fibre-reactive dyes, their preparation and use |
| KR102046778B1 (en) | 2012-06-15 | 2019-11-20 | 훈츠만 어드밴스트 머티리얼스(스위처랜드) 게엠베하 | Fibre-reactive dyes, their preparat1on and their use |
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