CN102585552B - Anthraquinone blue acid dye composition and application thereof in fiber dyeing - Google Patents
Anthraquinone blue acid dye composition and application thereof in fiber dyeing Download PDFInfo
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- CN102585552B CN102585552B CN2012100177318A CN201210017731A CN102585552B CN 102585552 B CN102585552 B CN 102585552B CN 2012100177318 A CN2012100177318 A CN 2012100177318A CN 201210017731 A CN201210017731 A CN 201210017731A CN 102585552 B CN102585552 B CN 102585552B
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- 239000000203 mixture Substances 0.000 title claims abstract description 68
- 239000000835 fiber Substances 0.000 title claims abstract description 13
- 238000004043 dyeing Methods 0.000 title claims description 29
- 239000000980 acid dye Substances 0.000 title abstract 5
- UHOKSCJSTAHBSO-UHFFFAOYSA-N indanthrone blue Chemical compound C1=CC=C2C(=O)C3=CC=C4NC5=C6C(=O)C7=CC=CC=C7C(=O)C6=CC=C5NC4=C3C(=O)C2=C1 UHOKSCJSTAHBSO-UHFFFAOYSA-N 0.000 title abstract 5
- 102000004169 proteins and genes Human genes 0.000 claims abstract description 8
- 108090000623 proteins and genes Proteins 0.000 claims abstract description 8
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 claims description 32
- 150000004056 anthraquinones Chemical class 0.000 claims description 32
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical class C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 30
- -1 alkali metal cation Chemical class 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 239000002131 composite material Substances 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 2
- 230000000996 additive effect Effects 0.000 claims description 2
- 238000009472 formulation Methods 0.000 claims description 2
- 239000004753 textile Substances 0.000 claims description 2
- 239000000975 dye Substances 0.000 abstract description 153
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 14
- 150000001875 compounds Chemical class 0.000 abstract description 6
- 238000005406 washing Methods 0.000 abstract description 2
- 239000004952 Polyamide Substances 0.000 abstract 2
- 229920002647 polyamide Polymers 0.000 abstract 2
- 244000002639 Delonix regia Species 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 40
- 239000000243 solution Substances 0.000 description 16
- 238000012360 testing method Methods 0.000 description 15
- OWYWGLHRNBIFJP-UHFFFAOYSA-N Ipazine Chemical compound CCN(CC)C1=NC(Cl)=NC(NC(C)C)=N1 OWYWGLHRNBIFJP-UHFFFAOYSA-N 0.000 description 11
- 239000002585 base Substances 0.000 description 8
- 229910052708 sodium Inorganic materials 0.000 description 8
- 239000011734 sodium Substances 0.000 description 8
- 159000000000 sodium salts Chemical class 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 238000010792 warming Methods 0.000 description 8
- 239000004677 Nylon Substances 0.000 description 7
- 229920001778 nylon Polymers 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 239000004744 fabric Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- AFPOMDNRTZLRMD-UHFFFAOYSA-N dodecyl carbonochloridate Chemical compound CCCCCCCCCCCCOC(Cl)=O AFPOMDNRTZLRMD-UHFFFAOYSA-N 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 238000002835 absorbance Methods 0.000 description 3
- 230000007547 defect Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- MHHGZCMFNNAVCQ-UHFFFAOYSA-M sodium;1-amino-4-[3-(2-hydroxyethylsulfamoyl)-4,5-dimethylanilino]-9,10-dioxoanthracene-2-sulfonate Chemical compound [Na+].OCCNS(=O)(=O)C1=C(C)C(C)=CC(NC=2C=3C(=O)C4=CC=CC=C4C(=O)C=3C(N)=C(C=2)S([O-])(=O)=O)=C1 MHHGZCMFNNAVCQ-UHFFFAOYSA-M 0.000 description 3
- 238000010189 synthetic method Methods 0.000 description 3
- 0 C*(c1cc(Nc(c(C(c2c3cccc2)=O)c2C3=O)cc(*)c2N)ccc1S(O)(=O)=O)=*=*=C Chemical compound C*(c1cc(Nc(c(C(c2c3cccc2)=O)c2C3=O)cc(*)c2N)ccc1S(O)(=O)=O)=*=*=C 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 238000000967 suction filtration Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- QZZSAWGVHXXMID-UHFFFAOYSA-N 1-amino-4-bromo-9,10-dioxoanthracene-2-sulfonic acid Chemical compound C1=CC=C2C(=O)C3=C(Br)C=C(S(O)(=O)=O)C(N)=C3C(=O)C2=C1 QZZSAWGVHXXMID-UHFFFAOYSA-N 0.000 description 1
- VTSSJXFQOQRLHW-UHFFFAOYSA-N Cc(c(N)c1)ccc1Nc(c(C(c1ccccc11)=O)c2C1=O)cc(S(O)(=O)=O)c2N Chemical compound Cc(c(N)c1)ccc1Nc(c(C(c1ccccc11)=O)c2C1=O)cc(S(O)(=O)=O)c2N VTSSJXFQOQRLHW-UHFFFAOYSA-N 0.000 description 1
- ZOHPJXCEVYGLJT-UHFFFAOYSA-N Nc1cc(Nc(c(C(c2ccccc22)=O)c3C2=O)cc(S(O)(=O)=O)c3N)ccc1S(O)(=O)=O Chemical compound Nc1cc(Nc(c(C(c2ccccc22)=O)c3C2=O)cc(S(O)(=O)=O)c3N)ccc1S(O)(=O)=O ZOHPJXCEVYGLJT-UHFFFAOYSA-N 0.000 description 1
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 229910000397 disodium phosphate Inorganic materials 0.000 description 1
- 235000019800 disodium phosphate Nutrition 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- HOQUWXSARQBQCW-UHFFFAOYSA-N hexadecyl carbonochloridate Chemical compound CCCCCCCCCCCCCCCCOC(Cl)=O HOQUWXSARQBQCW-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 229940045641 monobasic sodium phosphate Drugs 0.000 description 1
- 239000003002 pH adjusting agent Substances 0.000 description 1
- 238000009980 pad dyeing Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
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Abstract
The invention provides an anthraquinone blue acid dye composition which comprises one or more dye compounds selected from the dye compounds represented by general formula (1) and one or more dye compounds selected from the dye compounds represented by general formula (2). The anthraquinone blue acid dye composition provided by the invention has flamboyant color light, and excellent fastness. Compared with the dyes represented by general formula (1), the water washing fastness of the anthraquinone blue acid dye composition is greatly improved. The anthraquinone blue acid dye composition provided by the invention is successfully applied in dying practices of protein fibers, polyamide fibers and blended products of protein fibers and polyamide fibers. The general formula (1) and the general formula (2) are shown.
Description
Technical field
The present invention relates to a kind of anthraquinone type Vickery blue composition and the tint applications on filamentary material thereof.Particularly, the present invention relates to a kind of anthraquinone type Vickery blue composition and the tint applications on protein fibre and tynex thereof.
Background technology
The present invention is intended to develop a kind of coloured light is gorgeous, dyeing behavior is excellent, dyefastness is good protein fibre and the anthraquinone type Vickery blue composition of tynex dyeing use.The dyeing property that has above-mentioned excellence concurrently is actually rare for Vickery blue or its composition of protein fibre and tynex.
Current anthraquinone type Vickery blue is starting raw material mainly with bromamine acid.Wherein enjoy great prestige quality for a long time, when pushing away C.I.Acid Blue 277.This kind was developed as far back as the seventies in last century.This kind is synthetic convenient, has certain dyeing behavior characteristics, deeply is subject to the favor of dyeing, and is widely used.
The representative structure of C.I.Acid Blue 277 is as follows:
At first Ciba-Geigy company announces its structure and synthetic method, and its patent has:
US 3778453(1973)
US 3842102(1974)
US 3859283(1975)
Long-term practice shows, there is certain dyeing behavior defect in this dye species, causes each major company of the world to adopt the mode of composition to improve these defects.
The patent that forms composition by the blending mode by above-mentioned dyestuff is numerous, for example:
US 4396393(1983)(Ciba Geigy)
US 4402704(1983)(Ciba Geigy)
US 4408995(1983)(Ciba Geigy)
US 4445905(1984)(Ciba Geigy)
US 4537598(1985)(Ciba Geigy)
US 4954563(1990)(Ciba Geigy)
US 5131919(1992)(Ciba Geigy)
US 5196520(1992)(Ciba Geigy)
US 5234467(1993)(Ciba Geigy)
US 5630851(1997)(Ciba Geigy)
US 5092905(1992)(Sandoz)
The inventor is on the basis of lot of experiments research, find pleasantly surprisedly, with C, general formula of the present invention (1) dyestuff that I.Acid Blue 277 Representative Cultivars or its homologue mean, the dye composite that the dyestuff meaned with general formula of the present invention (2) forms, have good dyeing behavior.Anthraquinone type Vickery blue composition of the present invention, coloured light is gorgeous, not only has good dyeing behavior, and has excellent dyefastness concurrently.
The dyestuff that general formula (2) means is the dye species that Shanghai Argus Textile Chemical Co., Ltd. developed and applied for simultaneously patent of invention recently.Its synthetic method and dyeing behavior thereof are shown in the patent of invention of this kind.
General formula (2)
Research practice shows, anthraquinone type Vickery blue composition of the present invention is successfully used to the tint applications of protein fibre, tynex and BLENDED FABRIC thereof.
Summary of the invention
The inventor is on the basis of a large amount of research trials, find pleasantly surprisedly, the dye composite that one or more blue anthraquinone type matching stains that one or more blue anthraquinone type matching stains that general formula (1) means and general formula (2) mean form, have excellent dyeing behavior and every fastness.
It should be noted that Vickery blue composition of the present invention, compare with the dyestuff that its component dyestuff general formula (1) means, its every fastness all is improved.
Anthraquinone type Vickery blue composition provided by the invention comprise that certain proportion mixes one or more be selected from below shown in the dye composition that means of general formula (1) and one or more be selected from below shown in the dye composition that means of general formula (2).
General formula (1)
In formula:
R
1For H or CH
3
R
2For H, CH
3, CH
2CH
2OH, CH
2CH
2CH
2OH, CH
2CH
2OR
5And CH
2CH
2CH
2OR
6
R
3For CH
2CH
2OH, CH
2CH
2CH
2OH, CH
2CH
2OR
5And CH
2CH
2CH
2OR
6
R wherein
5And R
6Be CH independently respectively
3, C
2H
5And CH
2CH
2OH;
M is H or alkali metal cation.
General formula (2)
In formula:
N is 0,1,2 or 3;
M is 0 or 1;
M is H or alkali metal cation;
R
4For-COOR
7Or-COR
8Group;
R wherein
7For C
9～C
16The alkyl of straight or branched;
R
8For C
9～C
16The alkyl of straight or branched.
The present invention also provides the tint applications of above-mentioned anthraquinone type Vickery blue composition on protein fibre, tynex and BLENDED FABRIC thereof.
Embodiment
Dye composite of the present invention comprises the dye composition of one or more general formulas (1) expression and the dye composition that one or more general formulas (2) mean.
In dye composite of the present invention, the dyestuff that general formula (1) means (being called for short dyestuff I) is 90-10: 10-90, preferably 70-30: 30-70 with the weight ratio of the dyestuff (being called for short dyestuff II) that general formula (2) means.
One preferred embodiment in, the R of general formula (1)
1Group, be selected from H or CH
3R
2Be selected from H, CH
3, CH
2CH
2OH, CH
2CH
2CH
2OH, CH
2CH
2OR
5And CH
2CH
2CH
2OR
6R
3Be selected from CH
2CH
2OH, CH
2CH
2CH
2OH, CH
2CH
2OR
5And CH
2CH
2CH
2OR
6R in above formula
5And R
6Be CH independently respectively
3, C
2H
5And CH
2CH
2OH.
Another preferred embodiment in, in general formula (2) (CH
3)
nGroup, work as n=3 ,-CH
3Ortho position and the contraposition of lay respectively on benzene nucleus-NH-group of group; Work as n=2 ,-CH
3Contraposition, a position or the ortho position of lay respectively on benzene nucleus-NH-group of group; Work as n=1 ,-CH
3Ortho position, a position or the contraposition of be positioned on benzene nucleus-NH-group of group.
One preferred embodiment in, (the SO in general formula (2)
3M) m group, ortho position, a position or the contraposition of when m=1, be positioned on benzene nucleus-NH-group.
Another preferred embodiment in, in general formula (2)-the NHR group, ortho position, a position or the contraposition of be positioned on benzene nucleus-NH-group, be selected from-COOR of R group wherein
7Or-OCR
8Group, R
7And R
8Group is respectively independently selected from C
9～C
16The alkyl of straight or branched;
In the present invention, the dye composition that general formula (1) means for example comprises following example:
Dyestuff I-1
Dyestuff I-2
Dyestuff I-3
Dyestuff I-4
Dyestuff I-5 or
Dyestuff I-6;
In the present invention, the dye composition that general formula (2) means for example comprises following example:
Dyestuff II-1
Dyestuff II-2
Dyestuff II-3
Dyestuff II-4
Dyestuff II-5
Dyestuff II-6
Dyestuff II-7
Dyestuff II-8
Dyestuff II-9 or
Dyestuff II-10.
The represented dye composition of general formula (1) is known dye.
The synthetic method of the dye composition that general formula (1) means is shown in U.S. Pat 1927125 (1993) (GeneralAniline Works).
The dye composition that general formula (2) means can make by following preparation of dyestuff embodiment.
Anthraquinone type Vickery blue composition of the present invention also can contain the dye additive of various conventional uses in dyeing and dye formulations, and its consumption can be selected according to actual needs, and there is no particular limitation, generally is no more than 20 % by weight.For example, electrolyte salt, as sodium sulfate or Repone K, content 0～10 % by weight, preferably 2～6 % by weight; PH adjusting agent, as SODIUM PHOSPHATE, MONOBASIC or Sodium phosphate dibasic, content 0～5 % by weight, preferred 0.5～2.5 % by weight, dust-proofing agent 0～10 % by weight, preferred 0.1～2 % by weight; Solubility promoter 1～15 % by weight, preferred 0.1～3 % by weight.The present composition also can be basically by general formula (1) dyestuff of above-mentioned weight ratio with general formula (2) dyestuff forms or be comprised of general formula (1) dyestuff and general formula (2) dyestuff of above-mentioned weight ratio.
The preparation method of anthraquinone type Vickery blue composition of the present invention comprises above-mentioned general formula (1) dyestuff and general formula (2) dyestuff weight ratio is in accordance with regulations mixed.Mix available various ordinary method, as the mechanically mixing method.During mixing, general formula (1) dyestuff and general formula (2) dyestuff can powder types, or with particle form, or exist with aqueous solution form.For example, mixing step can suitable shredder as ball mill or needle mill in and in kneader or mixing machine, carry out.
Anthraquinone type Vickery blue composition of the present invention is suitable for dyeing and various materials widely thereof.
Anthraquinone type Vickery blue composition of the present invention can be applied to filamentary material and be fixed on fiber by several different methods as known in the art, for example can be dyeed by dip-dye method or pad dyeing method.
One, preparation of dyestuff embodiment
The present embodiment comprises synthetic example and the tint applications example thereof of general formula of the present invention (2) dyestuff.
1, general formula of the present invention (2) dyestuff is synthetic
1) synthesis step of the precursor compound of general formula of the present invention (2) dyestuff, can be with reference to following patent:
CN 101585974 (2009) (the Tianjin moral is triumphant)
US 3519656(1970)(Geigy)
DE 709689(1941)(Sandoz)
US 3813402(1974)(Crompton&Knowles Corp.)
US 3842102(1974)(Ciba-Geigy)
US 3859283(1975)(Ciba-Geigy)
US 4077987(1978)(Bayer)
These precursor compounds are:
Dyestuff II-1a
Dyestuff II-2a
Dyestuff II-4a
Dyestuff II-6a
Dyestuff II-7a
2) synthesis step of general formula of the present invention (2) dyestuff:
(1) prepare dyestuff II-1 by dyestuff II-1a
Take dye composition II-1a sodium salt 73.8 grams (content 78%), be dissolved in the water of 500 grams.At room temperature in 30 minutes, drip 100% chloroformic acid dodecyl ester (ClCOOC
12H
25) 26.1 grams, be warming up to 80-85 ℃, stir 1-2 hour.20% Na is often added in reaction
2CO
3Solution, the PH that maintains reaction solution of take is 6.5-7.5.It is terminal that reaction take that blue base disappears.
Reaction is saltoutd, is filtered after finishing, and makes approximately 102.8 gram wet cakes (solid content 80%) of dyestuff II-1, yield 95.8%.
Synthetic reaction formula is
(2) prepare dyestuff I-2 by dyestuff II-2a
Take dye composition II-1a sodium salt 65.8 grams (content 74%), be dissolved in the water of 500 grams.At room temperature in 30 minutes, drip 100% chloroformic acid dodecyl ester (ClCOOC
12H
25) 26.1 grams, be warming up to 80-85 ℃, stir 1-2 hour.20% Na is often added in reaction
2CO
3Solution, the PH that maintains reaction solution of take is 6.5-7.5.It is terminal that reaction take that blue base disappears.
Reaction is saltoutd, is filtered after finishing, and makes approximately 91.4 gram wet cakes (solid content 78%) of dyestuff II-2, yield 96.2%.Synthetic reaction formula is
(3) prepare dyestuff II-3 by dyestuff II-1a
Take dye composition II-1a sodium salt 77.8 grams (content 72%), be dissolved in the water of 500 grams.At room temperature in 30 minutes, drip 100% alkyl chloroformate (ClCOOC9H19) 21.7 grams, be warming up to 80-85 ℃, maintain this temperature 1-2 hour.20% Na is often added in reaction
2CO
3Solution, the PH that maintains reaction solution of take is 6.5-7.5.It is terminal that reaction take that blue base disappears.
Reaction is saltoutd, is filtered after finishing, and makes approximately 97.2 gram wet cakes (solid content 79%) of dyestuff II-3, yield 97.2%.
Synthetic reaction formula is
(4) prepare dyestuff II-4 by dyestuff II-4a
Take dye composition II-4a sodium salt 78.2 grams (content 70%), be dissolved in the water of 500 grams.At room temperature in 30 minutes, drip 100% chloroformic acid dodecyl ester (ClCOOC
12H
25) 26.1 grams, be warming up to 80-85 ℃, stir 1-2 hour.20% Na is often added in reaction
2CO
3Solution, the PH that maintains reaction solution of take is 6.5-7.5.It is terminal that reaction take that blue base disappears.
Reaction is saltoutd, is filtered after finishing, and makes approximately 98.3 gram wet cakes (solid content 82%) of dyestuff II-4, yield 94.3%.
Synthetic reaction formula is
(5) prepare dyestuff II-5 by dyestuff II-2a
Take dye composition II-2a sodium salt 65.8 grams (content 72%), be dissolved in the water of 500 grams.At room temperature in 30 minutes, drip 100% alkyl chloroformate (ClCOOC
9H
19) 21.7 grams, be warming up to 80-85 ℃, stir 1-2 hour.20% Na is often added in reaction
2CO
3Solution, the PH that maintains reaction solution of take is 6.5-7.5.It is terminal that reaction take that blue base disappears.
Reaction is saltoutd, is filtered after finishing, and makes approximately 83.2 gram wet cakes (solid content 81%) of dyestuff II-5, yield 95.6%.
Synthetic reaction formula is
(6) prepare dyestuff II-6 by dyestuff II-6a
Take dye composition II-6a sodium salt 57.1 grams (content 78.1%), be dissolved in the water of 500 grams.At room temperature in 30 minutes, drip 100% chloroformic acid dodecyl ester (ClCOOC
12H
25) 26.1 grams, be warming up to 80-85 ℃, keep this temperature 2-2.5 hour.20% Na is often added in reaction
2CO
3Solution, the PH that maintains reaction solution of take is 6.5-7.5.It is terminal that reaction take that blue base disappears.
Reaction is saltoutd, is filtered after finishing, and makes approximately 87.8 gram wet cakes (solid content 78%) of dyestuff II-6, yield 97.2%.
Synthetic reaction formula is
(7) prepare dyestuff II-7 by dyestuff II-7a
Take dye composition II-7a sodium salt 68.2 grams (content 78.3%), be dissolved in the water of 500 grams.At room temperature in 30 minutes, drip 100% chloroformic acid dodecyl ester (ClCOOC
12H
25) 26.1 grams, be warming up to 80-85 ℃, stir 1.5-2 hour.20% Na is often added in reaction
2CO
3Solution, the PH that maintains reaction solution of take is 6.5-7.5.It is terminal that reaction take that blue base disappears.
Reaction is saltoutd, is filtered after finishing, and makes approximately 99.6 gram wet cakes (solid content 78.6%) of dyestuff II-2, yield 95.3%.
Synthetic reaction formula is
(8) prepare dyestuff II-8 by dyestuff II-1a
Take dye composition II-1a sodium salt 73.8 grams (content 78%), be dissolved in the water of 500 grams.At room temperature in 30 minutes, drip 100% chloroformic acid cetyl ester (ClCOOC
16H
33) 32.1 grams, be warming up to 80-85 ℃, stir 1.5-2 hour.20% Na is often added in reaction
2CO
3Solution, the PH that maintains reaction solution of take is 6.5-7.5.It is terminal that reaction take that blue base disappears.
Reaction is saltoutd, is filtered after finishing, and makes approximately 112.0 gram wet cakes (solid content 80%) of dyestuff II-8, yield 94.2%.
Synthetic reaction formula is
2, the ultimate analysis of anthraquinone type Vickery blue of the present invention
By the dyestuff of the synthetic II-1 made～dyestuff II-8, through refining, the liquid phase separation laggard row element analysis of purifying, results of elemental analyses is listed in table 1
Table 1
From table 1, the structure of dyestuff II-1～dyestuff II-8 is as follows
Dyestuff II-1
Dyestuff II-2
Dyestuff II-3
Dyestuff II-4
Dyestuff II-5
Dyestuff II-6
Dyestuff II-7 and
Dyestuff II-8.
3, the Application Example of general formula of the present invention (2) dyestuff
Fastness to soaping test: by the dyeing nylon fabric, measure by international standard ISO 105-C10.
Embodiment 1
Fastness to soaping
Be determined as follows as stated above the fastness to soaping of dyestuff, test result is recorded in table 2
Table 2
From table 2:
General formula of the present invention (2) dye composition, have more excellent washing fastness.
Two, application performance embodiment
Every testing method of embodiment
The properties of the present embodiment is tested by following every testing method
1, solubleness: take a certain amount of dyestuff in the beaker of 250ml, add the hot water of 80 ℃ of 100ml, with the mechanical stirrer stirring, after 5 minutes, carry out suction filtration (during suction filtration, pressure 0.075Mpa, 5A qualitative filter paper), observe the filter paper residual condition.Reduce dye strength (G/L), until residual without dyestuff on filter paper, dye strength now (G/L) is the solubleness of dyestuff.
2, dyeing nylon exhaustion rate test: the dye liquor preparation, press the acid dyeing dyeing of nylon.After dyeing finishes, test respectively the absorbancy of dyeing residual liquid and the absorbance of the front dye liquor of dyeing.
Exhaustion rate=(absorbance of the absorbance of dye liquor after 1-dyeing/front dye liquor of dyeing) * 100%
3, colour fastness to chlorinated water test: by the dyeing nylon fabric, measure by international standard ISO 105E03.
4, colour fastness to perspiration test: by the dyeing nylon fabric, measure by international standard ISO 105-E04.
5, fastness to soaping test: by the dyeing nylon fabric, measure by international standard ISO 105-C10.
Dye type shown according to the form below 3 and consumption thereof evenly mix various dye components by ordinary method in this area, the various anthraquinone type Vickery blue compositions of the preparation embodiment of the present invention.
" % " in table 3 all means % by weight, and the gross weight of dye composite of take is benchmark.
Table 3
| Numbering | The dyestuff title | Form |
| 1 | A | 70% dyestuff I-1+30% dyestuff II-1 |
| 2 | B | 50% dyestuff I-1+50% dyestuff II-1 |
| 3 | C | 30% dyestuff I-1+70% dyestuff II-1 |
| 4 | D | 70% dyestuff I-2+30% dyestuff II-3 |
| 5 | E | 50% dyestuff I-2+50% dyestuff II-3 |
| 6 | F | 30% dyestuff I-2+70% dyestuff II-3 |
| 7 | G | 50% dyestuff I-3+50% dyestuff II-4 |
| 8 | Reference X | 100% dyestuff I-1 |
| 9 | Reference Y | 100% dyestuff II-1 |
| 10 | Reference W | 100% dyestuff I-2 |
| 11 | Reference U | 100% dyestuff II-3 |
Embodiment 1
The solubleness test
Be determined as follows as stated above the solubleness of dyestuff, test result is recorded in table 4
Table 4
From table 4:
Anthraquinone type Vickery blue composition of the present invention, have solubleness preferably, and level-dyeing property is better.
Embodiment 3
Dyeing nylon exhaustion rate is measured
Be determined as follows as stated above the exhaustion rate of dyestuff, test result is recorded in table 5
Table 5
From table 5:
Anthraquinone type Vickery blue composition of the present invention there is splendid dyeing exhaustion rate.
Embodiment 4
The chlorinated water resist fastness
Be determined as follows as stated above the colour fastness to chlorinated water of dyestuff, test result is recorded in table 6
Table 6
From table 6:
Anthraquinone type Vickery blue composition of the present invention still has excellent chlorinated water resist fastness.
Embodiment 5
Colour fastness to perspiration
Be determined as follows as stated above the colour fastness to perspiration of dyestuff, test result is recorded in table 7
Table 7
From table 7:
Anthraquinone type Vickery blue composition of the present invention has good fastness to perspiration.
Embodiment 6
Fastness to soaping
Be determined as follows as stated above the fastness to soaping of dyestuff, test result is recorded in table 8
Table 8
From table 8:
Anthraquinone type Vickery blue composition of the present invention has effectively improved dyestuff that general formula (I) the means look of soaping and has become large defect.
Claims (10)
1. an anthraquinone type Vickery blue composition, the dye composition that the general formula (2) shown in below the dye composition that the general formula (1) of this dye composite shown in below one or more are selected from means and one or more are selected from means and the optional conventional dye additive used in dyeing and dye formulations form:
In formula:
R
1For H or CH
3
R
2For H, CH
3, CH
2CH
2OH or CH
2CH
2CH
2OH;
R
3For CH
2CH
2OH or CH
2CH
2CH
2OH;
M is H or alkali metal cation;
In formula:
N is 0,1,2 or 3;
M is 0 or 1;
M is H or alkali metal cation;
R
4For-COOR
7Or-COR
8Group;
R wherein
7For C
9～C
16The alkyl of straight or branched;
R
8For C
9～C
16The alkyl of straight or branched;
The weight ratio of the dye composition that the dye composition that general formula (1) means and general formula (2) mean is 90～10:10～90.
2. anthraquinone type Vickery blue composition claimed in claim 1, its characteristic is, the dye composition that general formula (1) means is 70～30:30～70 with the weight ratio of the dye composition of general formula (2) expression.
3. anthraquinone type Vickery blue composition claimed in claim 1, is characterized in that, the R of general formula (1)
1Group, be selected from CH
3R
2Be selected from H; R
3Be selected from CH
2CH
2OH or CH
2CH
2CH
2OH.
4. anthraquinone type Vickery blue composition claimed in claim 1, is characterized in that, in general formula (2)-(CH
3)
nGroup, work as n=3 ,-CH
3Ortho position and the contraposition of lay respectively on benzene nucleus-NH-group of group; Work as n=2 ,-CH
3Contraposition, a position or the ortho position of lay respectively on benzene nucleus-NH-group of group; Work as n=1 ,-CH
3Ortho position, a position or the contraposition of be positioned on benzene nucleus-NH-group of group.
5. anthraquinone type Vickery blue composition claimed in claim 1, its characteristic is, (the SO in general formula (2)
3M)
mGroup, ortho position, a position or the contraposition of when m=1, be positioned on benzene nucleus-NH-group.
6. anthraquinone type Vickery blue composition claimed in claim 1, its characteristic is, in general formula (2)-NHR
4Group, ortho position, a position or the contraposition of be positioned on benzene nucleus-NH-group.
7. anthraquinone type Vickery blue composition claimed in claim 1, its characteristic is, the R in general formula (2)
4Be selected from-COOR of group
7Group, R
7Group is independently selected from C
9～C
16The alkyl of straight or branched;
8. anthraquinone type Vickery blue composition claimed in claim 1, its characteristic is, the dye composition that general formula (1) means is:
9. anthraquinone type Vickery blue composition claimed in claim 1, its characteristic is, the dye composition that general formula (2) means is:
In claim 1～9 the described anthraquinone type Vickery blue of any one composition in the tint applications of protein fibre, tynex and its blended textile.
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| CN2012100177318A CN102585552B (en) | 2012-01-19 | 2012-01-19 | Anthraquinone blue acid dye composition and application thereof in fiber dyeing |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2012100177318A CN102585552B (en) | 2012-01-19 | 2012-01-19 | Anthraquinone blue acid dye composition and application thereof in fiber dyeing |
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| CN102585552B true CN102585552B (en) | 2013-12-04 |
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| CN102766355B (en) * | 2012-08-07 | 2013-12-25 | 上海雅运纺织化工股份有限公司 | Anthraquinone blue dye composition and dyeing applications of same to fibers |
| CN105385189A (en) * | 2015-11-30 | 2016-03-09 | 无锡新德印染制品有限公司 | Blue reactive dye composition |
| CN113881243B (en) * | 2021-11-08 | 2023-11-10 | 上海雅运新材料有限公司 | Dark red dye compound, preparation method and dyeing application thereof |
Citations (6)
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|---|---|---|---|---|
| CN1109533A (en) * | 1993-12-16 | 1995-10-04 | 希巴-盖吉股份公司 | Method of three color dyeing or printing |
| EP0823505A1 (en) * | 1996-07-12 | 1998-02-11 | Ciba SC Holding AG | Process for trichromic dyeing or printing |
| US6030420A (en) * | 1997-12-10 | 2000-02-29 | Ciba Specialty Chemicals Corporation | Dye mixtures and the use thereof |
| US6033445A (en) * | 1997-02-10 | 2000-03-07 | Ciba Specialty Chemicals Corporation | Dye mixtures and their use |
| US6090165A (en) * | 1997-02-10 | 2000-07-18 | Ciba Specialty Chemicals Corporation | Dye mixtures and their use |
| CN101177546A (en) * | 2007-11-30 | 2008-05-14 | 上虞新晟化工工业有限公司 | Acid blue dye composition |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE602006013644D1 (en) * | 2005-07-20 | 2010-05-27 | Clariant Finance Bvi Ltd | ACID COLOR COMPOSITION OF ANTHRAQUINONE DYES |
-
2012
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Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1109533A (en) * | 1993-12-16 | 1995-10-04 | 希巴-盖吉股份公司 | Method of three color dyeing or printing |
| EP0823505A1 (en) * | 1996-07-12 | 1998-02-11 | Ciba SC Holding AG | Process for trichromic dyeing or printing |
| US6033445A (en) * | 1997-02-10 | 2000-03-07 | Ciba Specialty Chemicals Corporation | Dye mixtures and their use |
| US6090165A (en) * | 1997-02-10 | 2000-07-18 | Ciba Specialty Chemicals Corporation | Dye mixtures and their use |
| US6030420A (en) * | 1997-12-10 | 2000-02-29 | Ciba Specialty Chemicals Corporation | Dye mixtures and the use thereof |
| CN101177546A (en) * | 2007-11-30 | 2008-05-14 | 上虞新晟化工工业有限公司 | Acid blue dye composition |
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| CN102585552A (en) | 2012-07-18 |
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