CN101643590A - Blue active dye composition and application thereof - Google Patents

Blue active dye composition and application thereof Download PDF

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Publication number
CN101643590A
CN101643590A CN200810041514A CN200810041514A CN101643590A CN 101643590 A CN101643590 A CN 101643590A CN 200810041514 A CN200810041514 A CN 200810041514A CN 200810041514 A CN200810041514 A CN 200810041514A CN 101643590 A CN101643590 A CN 101643590A
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Prior art keywords
dyestuff
group
general formula
dye composition
blue active
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顾喆栋
曾建平
谢兵
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SHANGHAI ARGUS TEXTILE CHEMICALS CO Ltd
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SHANGHAI ARGUS TEXTILE CHEMICALS CO Ltd
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Abstract

The invention provides a blue active dye composition and application thereof. The dye composition is formed by mixing one or more dyes selected and expressed from a general formula (I) and one or moredyes selected and expressed from a general formula (II) according to a certain proportion. Compared with the dyes expressed by the general formula (I), the blue active dye composition obviously improves upgrading rates, levelling properties, solubility and compatibility. The blue active dye composition has the pleasant surprise that the composition keeps excellent dye fastness (such as light fastness, perspiration-light resistant color fastness and the like) of the dyes expressed by the general formula (I), and particularly has high color stability and acid spotting resistant color fastness.

Description

Blue active dye composition and application thereof
Technical field
The present invention relates to a kind of blue active dye composition and the tint applications on cellulose fiber peacekeeping wool fiber thereof.
Background technology
One of composition dyestuff of the blue active dye composition that the present invention relates to is the blue anthraquinone based dye.The representative structure formula of this class dyestuff is well-known C.I. Reactive Blue 19 100 #
Figure G2008100415146D00011
This class dyestuff color and luster is vivid, has good sun-resistant fastness and the photochromic fastness of sweat proof.These characteristics are actually rare in other blue active dye kinds.But long-term practice shows that the level-dyeing property of this class dyestuff, solubleness and consistency all remain further to be improved, thereby also influence its widespread use.
The method that adopts compound synergic is to improve one of the effective way of some application performance of above-mentioned dyestuff.
Many companies in the world and enterprise are disclosed in the following patent this effort of doing in recent years:
1.JP 2099564 (1990) (Mitsubishi changes into)
2.JP 6192589 (1994) (Sumitomos)
3.JP 7207180 (1995) (Mitsubishi changes into)
5,456,726 (1995) 4.US (Sumitomo)
5,536,277 (1996) 5.US (Sumitomo)
5,720,779 (1998) 6.US (Sumitomo)
7.EP?0905201(1999)(Bezema?AG)
8.CN 1580132 (2005) (Hua Bachang is dyed in Shanghai)
9.CN 1626582 (2005) (Everlight USA, Inc.)
10.JP 64043568 (1989) (Sumitomos)
11.JP 1103668 (1989) (Mitsubishi changes into)
4,888,028 (1989) 12.US (Mitsubishi changes into)
The composite dyestuff that above-mentioned patent adopts is azo dyes, triphen Er oxazole class dyestuff, phthalocyanines dye, first
Figure G2008100415146D00021
(Formazan) anthraquinone based dye of class dyestuff and analog structure etc.
The inventor finds that pleasantly surprisedly the general formula that employing is represented below (II) dyestuff and above-mentioned dyestuff are composite, not only significantly improves its application performance, and still keeps the dyefastness of above-mentioned dyestuff excellence.
Figure G2008100415146D00022
General formula (II)
The base this, the present invention is intended to improve the C.I. Reactive Blue 19 100 #Some application performance of series dyes and the purpose of dyefastness reach.
Summary of the invention
The inventor is by a large amount of tests, the dye composite that one or more blue active dyes of general formula (I) expression of finding to explain below and one or more blue active dyes of general formula (II) expression are formed pleasantly surprisedly has tint applications performance and every good dye fastness and dye of excellence.
Amazing is that the tint applications performance of blue active dye composition of the present invention and every dyefastness are taken in the length that it forms dye characteristic concurrently.Blue active dye composition of the present invention not only embodies the compound synergic effect aspect the improving of application performance, and still keeps the excellent dyefastness of general formula (I) dyestuff, for example sun-resistant fastness and the photochromic fastness of sweat proof.Blue active dye composition of the present invention has good level-dyeing property, enhancing rate and consistency, can be effectively applied to three primary color dyeing.Particularly, blue active dye composition of the present invention has very high color stability and acidproof spot colour fastness.
The dyestuff of general formula (II) expression shown in below the dyestuff of general formula (I) expression of blue active dye composition provided by the invention shown in below one or more are selected from by the certain proportion blended and one or more are selected from is formed.
Figure G2008100415146D00031
General formula (I)
In the formula: Y 1Be selected from-CH 2CH 2OSO 3M ,-CH=CH 2Or-CH 2CH 2Cl;
R 1Be selected from-H ,-C 1-4Alkoxyl group ,-C 1-4Alkyl or-COOM;
M is selected from-H or alkali metal cation;
General formula (II)
In the formula: X be selected from Cl, F or
Figure G2008100415146D00033
Y 2Be selected from-CH 2CH 2OSO 3M or-CH=CH 2
R 2Be selected from-C 1-4Alkyl ,-Cl or-C 1-4Alkoxyl group;
R 3Be selected from-H ,-C 1-4Alkyl ,-Cl ,-C 1-4Alkoxyl group or-SO 3M;
M is selected from-H or alkali metal cation;
N is selected from 1 or 2;
Q 1And Q 2In one be-NH 2Group, then another is-the OH group.
The invention provides the tint applications of above-mentioned blue active dye composition on cellulose fiber peacekeeping wool fiber.
Embodiment
Blue active dye composition of the present invention comprises the dyestuff of one or more general formulas (I) expression and the dyestuff of one or more general formulas (II) expression.
In dye composite of the present invention, one or more dyestuffs of general formula (I) expression with the weight ratio of one or more dyestuffs that general formula (II) is represented are: general formula (I) dyestuff: general formula (II) dyestuff=90～10: 10～90, preferably 80～20: 20～80.
One preferred embodiment in, in the general formula (I)-SO 3Y 1Group is positioned on the benzene nucleus-the NH-group between position or contraposition.Another preferred embodiment in, in the general formula (II) right side-SO 2Y 2Group is positioned on the benzene nucleus-the NH-group between position or contraposition; R 1Group is positioned on the benzene nucleus-ortho position or the contraposition of NH-group.
One preferred embodiment in, in the general formula (II) by Q 1One side place-SO 3The M group is positioned on the benzene nucleus-ortho position, contraposition or a position of N=N-group; By Q 2A SO at one side place 3The M group is positioned on the benzene nucleus-ortho position or the contraposition of N=N-group; By Q 2One side place is if any two-SO 3The M group, then they are positioned on the benzene nucleus-ortho position and the contraposition of N=N-group.Its-the NH group is positioned on the benzene nucleus-contraposition or a position of N=N-group.
In another optimal way, the Q in the general formula (II) 1And Q 2One in the group is-NH 2Group, another is-the OH group.
In a preferred implementation, the M in general formula (I) and the general formula (II) +Be selected from-H +, Na +Or K +
Another preferred embodiment in, n is preferably 1 in the general formula (II).
Among the present invention, the dyestuff of general formula (I) expression for example includes but not limited to following example:
Figure G2008100415146D00041
Dyestuff I-1
Figure G2008100415146D00042
Dyestuff I-2
Figure G2008100415146D00051
Dyestuff I-3
Dyestuff I-4
Figure G2008100415146D00053
Dyestuff I-5
Among the present invention, the dyestuff of general formula (II) expression for example includes but not limited to following example:
Figure G2008100415146D00054
Dyestuff II-1
Figure G2008100415146D00055
Dyestuff II-2
Figure G2008100415146D00061
Dyestuff II-3
Figure G2008100415146D00062
Dyestuff II-4
Figure G2008100415146D00063
Dyestuff II-5
Figure G2008100415146D00064
Dyestuff II-6
The dyestuff of general formula (I) expression is a known dye.US 3,372, and 170 (1968), JP 2002012786 (2002) announced the structure and the synthetic method thereof of the dyestuff of general formula (I) expression.
And the dyestuff of general formula (II) expression also is a known dye.US 4,548,612 (1985) (Sumitomos), US 4,412, and 948 (1983) (Sumitomos) disclose the structure and the synthetic method thereof of above-mentioned dyestuff.
The full content of above-mentioned document is referred among the present invention.
Blue active dye 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 by actual needs, and there is no particular limitation, generally is no more than 20 weight %.For example, electrolyte salt, as sodium sulfate or Repone K, content 0～10 weight %, preferred 2～6 weight %; The pH regulator agent, as SODIUM PHOSPHATE, MONOBASIC or Sodium phosphate dibasic, content 0～5%, preferred 0.5～2.5 weight %, dust-proofing agent 0～10 weight %, preferred 0.1～2 weight %; Solubility promoter 1～15 weight %, preferred 0.1～3 weight %.The present composition also can be basically be made up of the dyestuff I and the dyestuff II of above-mentioned weight ratio.
The preparation method of blue active dye composition of the present invention comprises above-mentioned dyestuff I and dyestuff II weight ratio is in accordance with regulations mixed.Mix available various ordinary method, as the mechanically mixing method.During mixing, dyestuff I and dyestuff II can powder types, or with particle form, or exist with aqueous solution form.For example, mixing step can carry out in suitable shredder such as ball mill or needle mill and in kneader or mixing machine.
Blue active dye composition of the present invention is suitable for the tint applications of cotton fibre.
Blue active dye composition of the present invention can be applied to filamentary material and is fixed on the fiber with several different methods as known in the art, for example can dye with dip-dye method or pad dyeing method.
Embodiment
The following test determines of various performances of various dye composites among the embodiment.
1, enhancing rate test: fabric is pressed 60 ℃ of constant temperature technology dyeing of reactive dyestuffs, and dyeing concentration is 0.5%, 1%, 2%, 4%, 6%o.w.f. (dyestuff is heavy to fabric).Dyeing back fabric is tested its Apparent Depth K/S value and record with Datacolor 650TM color measurement instrument after fixed temperature and humidity is handled.
2, degree of fixation F value: the absorbancy of the washing raffinate of test dyeing back fabric, and according to formula calculating F value.
Formula: absorbance * 100% of dye liquor before the absorbance ÷ dyeing of degree of fixation F value=E value-dyeing back dye liquor
3, just dye rate S value: the absorbance of dye liquor when adding before the alkali in the test dye dyeing course, calculate the S value according to formula.
Formula: just dye rate S value=(1-adds the absorbance of the preceding dye liquor of absorbance ÷ dyeing of the preceding dye liquor of alkali) * 100%
4, degree of exhaustion E value: the absorbance of dye liquor before and after the test dyeing, calculate the E value according to formula.
Formula: degree of exhaustion E value=(absorbance of dye liquor before the absorbance ÷ dyeing of 1-dyeing back dye liquor) * 100%
5, salt alkali solubility: testing standard is with reference to ISO 105-Z08:1995
6, sun-resistant fastness: testing standard is with reference to AATCC 16E
7, the photochromic fastness of sweat proof: testing standard is with reference to JIS L 0888
8, colour fastness to perspiration: testing standard is with reference to ISO 105-E04
9, fastness to soaping: testing standard is with reference to ISO 105-C10
10, colour fastness to rubbing: testing standard is with reference to ISO 105-X12
11, color stable property testing: with the color stability of Datacolor 650TM color measurement instrument test dyeing cloth specimen under Different Light, and the DE value under the record Different Light.
12, acidproof spot colour fastness: testing standard is with reference to ISO 105-E05
Press dye type shown in the table 1 and consumption thereof with various dye components by ordinary method uniform mixing in this area, the various red reactive dye compositions of the preparation embodiment of the invention and with reference to the various red reactive dyes of ratio.
" % " in the table 1 all represents weight %, is benchmark with the gross weight of orchil composition.
Table 1
Figure G2008100415146D00081
* dyestuff 100%I-1, * dyestuff 100%II-1, * dyestuff 100%II-2 all are commercial dye.
The dye composite that * CN 1580132 (2005) patents are announced.
Actual measurement example 1
The coloured light of blue active dye composition of the present invention
The dyestuff color and luster of general formula (I) expression is bright-coloured sapphirine.The dyestuff color and luster of general formula (II) expression is hides cyan deeply.
The coloured light of blue active dye composition of the present invention, can be as required by a certain percentage the dyestuff of general formula (I) expression adjust with the dyestuff that general formula (II) is represented, thereby can constitute the three primary colors combination with other yellow, orchil effectively, improve its actual application value.
Actual measurement example 2
Enhancing rate is measured (the maximum absorption wavelength 610mm K/S of place value)
Measure the enhancing rate of following dyestuff or dye composite as stated above.Outcome record is in table 2-4.
Pure cotton fabric table 2
Figure G2008100415146D00091
Table 3
Figure G2008100415146D00092
Figure G2008100415146D00101
By table 2, table 3 as seen,
1) in the dyeing of pure cotton fabric, blue active dye composition of the present invention is compared with the dyestuff of general formula (I) expression, and its enhancing rate is significantly increased;
2) in the dyeing of pure cotton fabric, the enhancing rate measured value of blue active dye composition of the present invention all is higher than its weighted mean of forming dyestuff, embodies the effect of compound synergic;
3) dyestuff 100%II-1 compares with dyestuff 100%II-2, and because of textural difference, its corresponding enhancing rate is successively decreased to some extent.
Wool fabric table 4
Figure G2008100415146D00102
By table 4 as seen
1) blue active dye composition of the present invention is at wool fabric dyeing, and its enhancing rate is better than dyeing at pure cotton fabric greatly;
2) blue active dye composition of the present invention is at wool fabric dyeing, and its enhancing rate measured value is higher than its weighted mean.
Actual measurement example 3
Just dying rate and degree of exhaustion measures
Measure the first rate and the degree of exhaustion of dying of following dyestuff or dye composite as stated above.Outcome record is in table 5-6.
Table 5
Figure G2008100415146D00111
Table 6
By table 5, table 6 as seen
1) dyestuff of blue active dye composition of the present invention and general formula (I) expression is compared, its just the rate of dying be significantly increased, show its with red, yellow dyes commonly used with the excellent compatibility of dying;
2) blue active dye composition of the present invention still keeps the good degree of exhaustion level with the dyestuff of general formula (I) expression.
3) the first rate and the degree of exhaustion of dying of blue active dye composition of the present invention, its measured value all is higher than its weighted mean, embodies its compound synergic ground effect.
Actual measurement example 4
The mensuration of salt alkali solubility
Measure the salt alkali solubility of following dyestuff or dye composite as stated above.Outcome record is in table 7-8.
Table 7
Figure G2008100415146D00121
Table 8
Figure G2008100415146D00122
By table 7, table 8 as seen
1) adding of the dyestuff of blue active dye composition formula of of the present invention (II) expression has improved the bad major defect of salt alkali solubility of the dyestuff of general formula (I) expression significantly, thereby has improved its application performance;
2) blue active dye composition of the present invention has higher salt alkali solubility, and the dyestuff that has improved general formula (I) expression effectively easily produces the defective of color dot look flower in dyeing course, improved level-dyeing property.
Actual measurement example 5
The mensuration of sun-resistant fastness and the photochromic fastness of sweat proof
Measure the sun-resistant fastness and the photochromic fastness of sweat proof of following dyestuff or dye composite as stated above.Outcome record is in table 9.
Table 9
Figure G2008100415146D00131
By table 9 as seen, blue active dye composition of the present invention still can keep the sun-resistant fastness of dyestuff of general formula (I) expression and the higher level of the photochromic fastness of sweat proof.
Actual measurement example 6
The mensuration of colour fastness to rubbing, fastness to soaping, colour fastness to perspiration and degree of fixation
Measure colour fastness to rubbing, fastness to soaping, colour fastness to perspiration and the degree of fixation of following dyestuff or dye composite as stated above.Outcome record is in table 10-12.
Table 10
Figure G2008100415146D00132
Table 11
Figure G2008100415146D00141
By table 10, table 11 as seen, blue active dye composition of the present invention keeps colour fastness to rubbing, fastness to soaping and colour fastness to perspiration preferably.
Table 12
By table 12 as seen, blue active dye composition of the present invention is compared with the dyestuff of general formula (I) expression, still keeps good degree of fixation.
Actual measurement example 7
The color stable property testing
Measure the color stability of following dyestuff or dye composite as stated above, outcome record is in table 13
Table 13
By table 13 as seen, the dye composite that blue active dye composition of the present invention is announced than CN 1580132 (2005) patents, color stability is good.The DE value is a relative value, and numerical value is more little, and the expression color stability is good more.
Actual measurement example 8
Acidproof spot colour fastness test
Measure the acidproof spot colour fastness of following dyestuff or dye composite as stated above, outcome record is in table 14
Table 14
Figure G2008100415146D00152
By table 14 as seen, the dye composite that blue active dye composition of the present invention is announced than CN 1580132 (2005) patents has excellent acid spot colour fastness.

Claims (10)

1. blue active dye composition, this dye composite comprise one or more be selected from below shown in the dyestuff of general formula (I) expression and one or more be selected from below shown in the dyestuff of general formula (II) expression:
Figure A2008100415140002C1
General formula (I)
In the formula: Y 1Be selected from-CH 2CH 2OSO 3M ,-CH=CH 2Or-CH 2CH 2Cl;
R 1Be selected from-H ,-C 1-4Alkoxyl group ,-C 1-4Alkyl or-COOM;
M is selected from-H or alkali metal cation;
Figure A2008100415140002C2
General formula (II)
In the formula: X be selected from Cl, F or
Figure A2008100415140002C3
Y 2Be selected from-CH 2CH 2OSO 3M or-CH=CH 2
R 2Be selected from-C 1-4Alkyl ,-Cl or-C 1-4Alkoxyl group;
R 3Be selected from-H ,-C 1-4Alkyl ,-Cl ,-C 1-4Alkoxyl group or-SO 3M;
M is selected from-H or alkali metal cation;
N is selected from 1 or 2;
Q 1And Q 2In one be-NH 2Group, then another is-the OH group.
2. the described blue active dye composition of claim 1, its characteristic are that the dyestuff of general formula (I) expression is 90～10: 10～90 with the weight ratio of the dyestuff that general formula (II) is represented, preferably 80～20: 20～80.
3. the described blue active dye composition of claim 1, its characteristic be, in the general formula (I)-SO 3Y 1Group is positioned on the benzene nucleus-the NH-group between position or contraposition; R 1Group is positioned on the benzene nucleus-ortho position or the contraposition of NH-group.
4. the described blue active dye composition of claim 1, its characteristic be, in the general formula (II) by Q 1One side place-SO 3The M group is positioned on the benzene nucleus-ortho position, contraposition or a position of N=N-group; By Q 2A SO at one side place 3The M group is positioned on the benzene nucleus-ortho position or the contraposition of N=N-group; By Q 2One side place is if any two-SO 3The M group, then they are positioned on the benzene nucleus-ortho position and the contraposition of N=N-group.Its-the NH group is positioned on the benzene nucleus-contraposition or a position of N=N-group.
5. the described blue active dye composition of claim 1, its characteristic be, in the general formula (II) right side-SO 2Y 2Group is positioned on the benzene nucleus-contraposition or a position of NH-group; Its R 3Group is positioned on the benzene nucleus-ortho position or the contraposition of NH-group.
6. the described blue active dye composition of claim 1, its characteristic is that the M in general formula (I) and the general formula (II) is selected from-H +, Na +Or K +N is 1 or 2.
7. the described blue active dye composition of claim 1, its characteristic is, the Q in the general formula (II) 1And Q 2One is-NH in the group 2Group, another is-the OH group.
8. the described blue active dye composition of claim 1, its characteristic are that the compound of general formula (I) is selected from as next group compound:
Figure A2008100415140003C1
Dyestuff I-1
Dyestuff I-2
Figure A2008100415140004C1
Dyestuff I-3
Figure A2008100415140004C2
Dyestuff I-4
Figure A2008100415140004C3
Dyestuff I-5
9. the described blue active dye composition of claim 1, its characteristic are that the compound of general formula (II) is selected from as next group compound:
Figure A2008100415140004C4
Dyestuff II-1
Dyestuff II-2
Figure A2008100415140005C2
Dyestuff II-3
Figure A2008100415140005C3
Dyestuff II-4
Figure A2008100415140005C4
Dyestuff II-5
Figure A2008100415140005C5
Dyestuff II-6
In the claim 1～9 each described blue active dye composition in the tint applications of cellulose fiber peacekeeping wool fabric.
CN200810041514A 2008-08-08 2008-08-08 Blue active dye composition and application thereof Pending CN101643590A (en)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102295840A (en) * 2010-06-25 2011-12-28 上海雅运纺织化工有限公司 Navy blue reactive dye composition and dyeing application thereof to fibers
CN102850823A (en) * 2012-09-28 2013-01-02 浙江亿得化工有限公司 Composite anthraquinone-type cobalt blue reactive dye
CN106833017A (en) * 2016-11-28 2017-06-13 浙江瑞华化工有限公司 A kind of blue active dye composition and its production and use

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102295840A (en) * 2010-06-25 2011-12-28 上海雅运纺织化工有限公司 Navy blue reactive dye composition and dyeing application thereof to fibers
CN102295840B (en) * 2010-06-25 2013-12-11 上海雅运纺织化工股份有限公司 Navy blue reactive dye composition and dyeing application thereof to fibers
CN102850823A (en) * 2012-09-28 2013-01-02 浙江亿得化工有限公司 Composite anthraquinone-type cobalt blue reactive dye
CN106833017A (en) * 2016-11-28 2017-06-13 浙江瑞华化工有限公司 A kind of blue active dye composition and its production and use

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Application publication date: 20100210