CN105155311A - Polyquaternium cationic formaldehyde-free fixing agent and preparing method thereof - Google Patents
Polyquaternium cationic formaldehyde-free fixing agent and preparing method thereof Download PDFInfo
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Abstract
The invention relates to a fixing agent and a preparing method thereof, in particular to a polyquaternium cationic formaldehyde-free fixing agent used for dyeing superfine fiber synthetic leather and a preparing method thereof. According to the fixing agent, quaternary ammonium branches are grafted on a molecular chain of a polymeric polyamine condensation compound to form a comb-shaped polymer in which quaternary ammonium and tertiary amine cations coexist. The fixing agent can effectively improve wet friction color fastness and dry-rubbing-resisting color fastness of the dyed superfine fiber synthetic leather and has a good fixing effect on the superfine fiber synthetic leather, and the preparation method of the fixing agent is simple and low in cost and has high industrial application value.
Description
Technical field
The present invention relates to a kind of color-fixing agent and preparation method thereof, be specifically related to a kind of aldehyde-free colour stabilizer for superfine fiber chemical leather dyeing and preparation method thereof.
Background technology
Color-fixing agent, as a kind of dyeing assistant, can improve the fastness of textile dyeing, makes more effective set between dyestuff and fiber.Color-fixing agent the earliest adopts the condensation product of dicyandiamide and formaldehyde, but due to free formaldehyde content higher, be prohibited from using.Current aldehyde-free colour stabilizer generally adopts the condensation product of polyamines and epoxychloropropane, by the manufacturing technique of diethylenetriamine and the formulated aldehyde-free colour stabilizer of epoxychloropropane disclosed in CN1534133 patent application, this kind of color-fixing agent colour fixation on flat textile product is better, but there is washing fastness and the lower slightly problem of light fastness, newer application also has employing dimethyl-dipropenyl ammonium chloride polycondensation or the polycationic compounds color-fixing agent with other unsaturated compound copolymerization, a kind of PDDA modification color-fixing agent and preparation method thereof disclosed in CN103015239 patent application, due to containing quaternary ammonium salt group, better effect is had than tertiary amine-type cationic fixing agent.
The dominant mechanism that polyamines class aldehyde-free colour stabilizer carries out fixation is that color-fixing agent can provide CATION, makes the anionic water-soluble dye of textile surface generate slightly soluble or difficulty soluble salt, reduces the solvability of dyestuff, thus improve Washing; Secondly, polyamines class aldehyde-free colour stabilizer contains reactive group, and this group can react with fiber, greatly promotes dyestuff and interfibrous adhesion, fixation ability is significantly improved.Therefore, the cation group of polyamines class aldehyde-free colour stabilizer is more, and reactive group is more, and polymer molecular weight is larger, and its colour fixation is better.
Superfine fiber chemical leather grows up on the basis fully dissecting natural leather, is the most ideal material substituting natural leather at present.The preparation flow of superfine fiber chemical leather is: nylon 6 and polyethylene blend spinning are formed islands-in-sea bicomponent fibre, and (wherein nylon is island phase, polyethylene is marine facies), make impregnating polyurethane resin after nonwoven fabric, form base cloth, then with hot toluene, polyethylene is dissolved, remaining nylon fiber is superfine fiber chemical leather, and the nylon fiber fiber number of superfine fiber chemical leather is the 0.1-0.001 dawn.On the one hand, because the dyeability of nylon own is poor; On the other hand, because obtained fiber is very thin, cause superfine fiber fabric dyeability very poor, COLOR FASTNESS is lower.Conventional polyamines class aldehyde-free colour stabilizer mostly is unbranched linear oligomer, produces little effect for superfine fiber fabric tint retention, adds dyeing cost and wastewater treatment difficulty on the contrary.
Summary of the invention
The object of the invention is for problems of the prior art, provide a kind of polyquarternium-type formaldehyde-free cation fixing agent of pectination, the present invention also provides the preparation method of described color-fixing agent.Described color-fixing agent effectively can improve the wet friction COLOR FASTNESS after superfine fiber chemical leather dyeing and resistance to xerotripsis COLOR FASTNESS, has good colour fixation to superfine fiber chemical leather.
The polyquarternium-type formaldehyde-free cation fixing agent of a kind of pectination of the present invention, is characterized in that, described color-fixing agent is by grafting quaternary ammonium salt side chain on the strand of aggretion type polyamines condensation product, the comb-shaped polymer that formation quaternary ammonium salt and tertiary amine cation coexist.Described color-fixing agent has such as formula structure shown in I:
Wherein, the quaternary ammonium salt side chain in dashed rectangle can be connected with the secondary nitrogen-atoms of any one on polyamines condensation product
X is the integer of 0-3, and the summation of m and n is the integer of 10-30
R
1, R
2, R
3for-CH
3,-CH
2cH
3,-CH
2cH
2cH
3in one
Formula I
The polyquarternium-type formaldehyde-free cation fixing agent of described pectination is prepared from by following method:
(1) synthetic mesophase product 1
Epoxychloropropane and diethylenetriamine (or ethylenediamine or triethylene tetramine or tetraethylene pentamine, following formula is for diethylenetriamine) in aqueous, at 60 DEG C-80 DEG C, reaction 1-2h, polyamines class condensation product is obtained than for polycondensation reaction occurs 1:1 according to amount of substance, i.e. intermediate product 1, course of reaction and molecular structural formula as follows:
Intermediate product 1
Wherein, n is the integer of 10-30
(2) synthetic mesophase product 2
Epoxychloropropane and tertiary amine, in water and methyl alcohol mixed solution, at 55 DEG C-65 DEG C, are 1:1-1:1.3 according to amount of substance ratio, there is quaterisation and obtain intermediate product 2, reaction 2-3h, the volume ratio of described water and methyl alcohol is 1:2, course of reaction and molecular structural formula as follows:
Intermediate product 2
Wherein, R
1, R
2, R
3for-CH
3,-CH
2cH
3,-CH
2cH
2cH
3in one
(3) graft reaction
Reactant liquor after step (1) and step (2) reaction being terminated merges, wherein, epoxychloropropane for the preparation of intermediate product 1 and the epoxychloropropane for the preparation of intermediate product 2 are 1:1-1:2 reaction according to amount of substance ratio, under agitation, temperature controls at 60 DEG C-80 DEG C, reaction time 2-3h, prepare such as formula the pectination water-soluble polymer shown in I, product is colourless to light yellow transparent solution, pH=9, by the cationic degree regulating the consumption of intermediate product 1 and intermediate product 2 can control described pectination polyquarternium-type formaldehyde-free cation fixing agent.
Polyquarternium-type formaldehyde-free cation fixing agent of the present invention has following beneficial effect: by grafting quaternary ammonium salt side chain on the strand of aggretion type polyamines condensation product, the comb-shaped polymer that formation quaternary ammonium salt and tertiary amine cation coexist, the degree of polymerization of described polymer can reach 18-22, has relatively large molecular weight; By the cationic degree regulating the consumption of intermediate product 1 and intermediate product 2 to control described pectination polyquarternium-type formaldehyde-free cation fixing agent, relatively high cationic degree can be obtained.Therefore, described polymer effectively can improve the wet friction COLOR FASTNESS after superfine fiber chemical leather dyeing and resistance to xerotripsis COLOR FASTNESS, to superfine fiber chemical leather, there is good colour fixation, as described in example 1 above: wet friction COLOR FASTNESS 4 grades, resistance to xerotripsis COLOR FASTNESS 4.5 grades, color fastness to light 4 grades, colour fastness to perspiration 4 grades; And conventional color-fixing agent generally can reach wet friction COLOR FASTNESS 2.5-3 level, resistance to xerotripsis COLOR FASTNESS 4 grades, color fastness to light 3 grades, colour fastness to perspiration 3 grades.Meanwhile, described polyquarternium-type formaldehyde-free cation fixing agent preparation method is simple, with low cost, has higher industrial application value.
Detailed description of the invention
embodiment 1
(1) synthetic mesophase product 1
In reactor 1, add diethylenetriamine (10.3kg) and deionized water (10L), stir, pass into nitrogen, be heated to 60 DEG C, start to drip epoxychloropropane (9.3kg), control temperature of reactor and be no more than 80 DEG C, after epoxychloropropane dropwises, control temperature is 75 DEG C, after reaction 1.5h, reaction stops, product is pale yellow transparent slightly thick liquid, and pH=8-9, solid content is 66.18%.
(2) synthetic mesophase product 2
In reactor 2, add deionized water (10L), methyl alcohol (20L), epoxychloropropane (9.3kg), stir, add triethylamine (12.2kg) in batches, be heated to 55 DEG C, control reaction temperature and be no more than 60 DEG C, stop after reaction 2h, product is water white solution, pH=9-10, and product solid content is 45.4%.
(3) graft reaction
Reactant liquor after step (1) and step (2) reaction being terminated merges, and under agitation, temperature controls at 80 DEG C, reaction time 2.5h, and prepare such as formula the pectination water-soluble polymer shown in I, wherein x=1, products therefrom is colourless transparent solution, pH=9.
The polyquarternium-type formaldehyde-free cation fixing agent prepared is carried out the test to superfine fiber chemical leather colour fixation, and test result is: moisture-proof colorfastness to rubbing 4 grades, resistance to xerotripsis COLOR FASTNESS 4.5 grades, color fastness to light 4 grades, colour fastness to perspiration 4 grades.
embodiment 2
(1) synthetic mesophase product 1
In reactor 1, add ethylenediamine (3.0kg) and deionized water (5L), stir, pass into nitrogen, be heated to 65 DEG C, start to drip epoxychloropropane (4.6kg), control temperature of reactor and be no more than 80 DEG C, after epoxychloropropane dropwises, control temperature is 75 DEG C, after reaction 2h, reaction stops, product is pale yellow transparent slightly thick liquid, and pH=8, solid content is 68.38%.
(2) synthetic mesophase product 2
In reactor 2, add trimethylamine aqueous solution (23.3kg, trimethylamine mass fraction is 33%), methyl alcohol (30L), epoxychloropropane (9.3kg), stir, be heated to 55 DEG C, control reaction temperature and be no more than 60 DEG C, stop after reaction 2.5h, product is water white solution, pH=9, and product solid content is 46.8%.
(3) graft reaction
Reactant liquor after step (1) and step (2) reaction being terminated merges, and under agitation, temperature controls at 70 DEG C, reaction time 3h, and prepare such as formula the pectination water-soluble polymer shown in I, wherein x=0, products therefrom is colourless transparent solution, pH=9.
The polyquarternium-type formaldehyde-free cation fixing agent prepared is carried out the test to superfine fiber chemical leather colour fixation, and test result is: moisture-proof colorfastness to rubbing 4 grades, resistance to xerotripsis COLOR FASTNESS 4 grades, color fastness to light 4 grades, colour fastness to perspiration 4 grades.
embodiment 3
(1) synthetic mesophase product 1
In reactor 1, add triethylene tetramine (14.6kg) and deionized water (10L), stir, pass into nitrogen, be heated to 60 DEG C, start to drip epoxychloropropane (9.3kg), control temperature of reactor and be no more than 80 DEG C, after epoxychloropropane dropwises, control temperature is 75 DEG C, after reaction 1h, reaction stops, product is pale yellow transparent slightly thick liquid, and pH=9, solid content is 65.16%.
(2) synthetic mesophase product 2
In reactor 2, add deionized water (10L), methyl alcohol (20L), epoxychloropropane (9.3kg), stir, add triethylamine (12.2kg) in batches, be heated to 55 DEG C, control reaction temperature and be no more than 60 DEG C, stop after reaction 2h, product is water white solution, pH=9-10, and product solid content is 45.4%.
(3) graft reaction
Reactant liquor after step (1) and step (2) reaction being terminated merges, and under agitation, temperature controls at 80 DEG C, reaction time 2.5h, prepares such as formula the pectination water-soluble polymer shown in I, wherein x=2, products therefrom is light yellow transparent solution, pH=9.
The polyquarternium-type formaldehyde-free cation fixing agent prepared is carried out the test to superfine fiber chemical leather colour fixation, and test result is: moisture-proof colorfastness to rubbing 4.5 grades, resistance to xerotripsis COLOR FASTNESS 4 grades, color fastness to light 4 grades, colour fastness to perspiration 4 grades.
embodiment 4
(1) synthetic mesophase product 1
In reactor 1, add tetraethylene pentamine (18.3kg) and deionized water (10L), stir, pass into nitrogen, be heated to 60 DEG C, start to drip epoxychloropropane (9.3kg), control temperature of reactor and be no more than 80 DEG C, after epoxychloropropane dropwises, control temperature is 75 DEG C, after reaction 1.5h, reaction stops, product is pale yellow transparent slightly thick liquid, and pH=8-9, solid content is 64.24%.
(2) synthetic mesophase product 2
In reactor 2, add deionized water (15L), methyl alcohol (30L), epoxychloropropane (9.3kg), stir, add triethylamine (12.2kg) in batches, be heated to 55 DEG C, control reaction temperature and be no more than 60 DEG C, stop after reaction 2h, product is water white solution, pH=9-10, and product solid content is 45.4%.
(3) graft reaction
Reactant liquor after step (1) and step (2) reaction being terminated merges, and under agitation, temperature controls at 80 DEG C, reaction time 2.5h, and prepare such as formula the pectination water-soluble polymer shown in I, wherein x=3, products therefrom is colourless transparent solution, pH=9.
The polyquarternium-type formaldehyde-free cation fixing agent prepared is carried out the test to superfine fiber chemical leather colour fixation, and test result is: moisture-proof colorfastness to rubbing 4 grades, resistance to xerotripsis COLOR FASTNESS 4.5 grades, color fastness to light 4 grades, colour fastness to perspiration 4 grades.
Claims (5)
1. a polyquarternium-type formaldehyde-free cation fixing agent, it is characterized in that, described color-fixing agent is by grafting quaternary ammonium salt side chain on the strand of aggretion type polyamines condensation product, the comb-shaped polymer that formation quaternary ammonium salt and tertiary amine cation coexist, and described color-fixing agent has such as formula structure shown in I:
Wherein, the quaternary ammonium salt side chain in dashed rectangle can be connected with the secondary nitrogen-atoms of any one on polyamines condensation product
X is the integer of 0-3, and the summation of m and n is the integer of 10-30
R
1, R
2, R
3for-CH
3,-CH
2cH
3,-CH
2cH
2cH
3in one
Formula I.
2. a kind of polyquarternium-type formaldehyde-free cation fixing agent as claimed in claim 1, is characterized in that, described color-fixing agent has such as formula structure shown in II:
Wherein, the quaternary ammonium salt side chain in dashed rectangle can be connected with the secondary nitrogen-atoms of any one on polyamines condensation product
The summation of m and n is 20
Formula II.
3. the preparation method of a kind of polyquarternium-type formaldehyde-free cation fixing agent as claimed in claim 1, is characterized in that, comprise the steps:
(1) synthetic mesophase product 1
Epoxychloropropane and diethylenetriamine or ethylenediamine or triethylene tetramine or tetraethylene pentamine are in aqueous, at 60 DEG C-80 DEG C, reaction 1-2h, polyamines class condensation product is obtained than for polycondensation reaction occurs 1:1 according to amount of substance, i.e. intermediate product 1, for diethylenetriamine, course of reaction and molecular structural formula as follows:
Intermediate product 1
Wherein, n is the integer of 10-30
(2) synthetic mesophase product 2
Epoxychloropropane and tertiary amine, in water and methyl alcohol mixed solution, at 55 DEG C-65 DEG C, are 1:1-1:1.3 according to amount of substance ratio, there is quaterisation and obtain intermediate product 2, reaction 2-3h, the volume ratio of described water and methyl alcohol is 1:2, course of reaction and molecular structural formula as follows:
Intermediate product 2
Wherein, R
1, R
2, R
3for-CH
3,-CH
2cH
3,-CH
2cH
2cH
3in one
(3) graft reaction
Reactant liquor after step (1) and step (2) reaction being terminated merges, wherein, epoxychloropropane for the preparation of intermediate product 1 and the epoxychloropropane for the preparation of intermediate product 2 are 1:1-1:2 reaction according to amount of substance ratio, under agitation, temperature controls at 60 DEG C-80 DEG C, reaction time 2-3h, prepares such as formula the pectination water-soluble polymer shown in I, product is colourless to light yellow transparent solution, pH=9.
4. the preparation method of a kind of polyquarternium-type formaldehyde-free cation fixing agent as claimed in claim 3, it is characterized in that, described intermediate product 1 is by epoxychloropropane and diethylenetriamine in aqueous, at 60 DEG C-80 DEG C, reaction 1-2h, obtains polyamines class condensation product according to amount of substance than for polycondensation reaction occurs 1:1.
5. the preparation method of a kind of polyquarternium-type formaldehyde-free cation fixing agent as described in claim 3 or 4, it is characterized in that, in described step (3) graft reaction, for the preparation of intermediate product 1 epoxychloropropane and for the preparation of intermediate product 2 epoxychloropropane according to amount of substance than for 1:1 react.
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105672006A (en) * | 2016-04-01 | 2016-06-15 | 吴江市泽旺纺织有限公司 | Quick drying type color fixing agent and preparation method thereof |
| CN109056383A (en) * | 2018-08-01 | 2018-12-21 | 湖南七纬科技有限公司 | A kind of printing and dyeing assistant and preparation method thereof |
| CN109503801A (en) * | 2018-11-30 | 2019-03-22 | 西安工程大学 | Dacron Non-water washing continuous exhaust dyeing waterborne polyurethane resin synthetic method |
| CN109667176A (en) * | 2019-01-07 | 2019-04-23 | 梅丽玲 | The preparation method of modified fibroin albumen color fixing agent and its application in silk fixation |
| CN110331605A (en) * | 2019-07-19 | 2019-10-15 | 绍兴中纺化工有限公司 | A kind of natural dye color fixing agent and preparation method thereof |
| CN111138662A (en) * | 2020-01-08 | 2020-05-12 | 广东德美精细化工集团股份有限公司 | Preparation method and application of active hydrophilic formaldehyde-free color fixing agent |
| US20210180246A1 (en) * | 2018-08-21 | 2021-06-17 | Dow Global Technologies Llc | Process for Forming Synthetic Leather |
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Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105672006A (en) * | 2016-04-01 | 2016-06-15 | 吴江市泽旺纺织有限公司 | Quick drying type color fixing agent and preparation method thereof |
| CN109056383A (en) * | 2018-08-01 | 2018-12-21 | 湖南七纬科技有限公司 | A kind of printing and dyeing assistant and preparation method thereof |
| US20210180246A1 (en) * | 2018-08-21 | 2021-06-17 | Dow Global Technologies Llc | Process for Forming Synthetic Leather |
| US11834780B2 (en) * | 2018-08-21 | 2023-12-05 | Dow Global Technologies Llc | Process for forming synthetic leather |
| CN109503801A (en) * | 2018-11-30 | 2019-03-22 | 西安工程大学 | Dacron Non-water washing continuous exhaust dyeing waterborne polyurethane resin synthetic method |
| CN109667176A (en) * | 2019-01-07 | 2019-04-23 | 梅丽玲 | The preparation method of modified fibroin albumen color fixing agent and its application in silk fixation |
| CN109667176B (en) * | 2019-01-07 | 2021-08-24 | 章华海 | Preparation method of modified silk fibroin color fixing agent and application of modified silk fibroin color fixing agent in silk color fixing |
| CN110331605A (en) * | 2019-07-19 | 2019-10-15 | 绍兴中纺化工有限公司 | A kind of natural dye color fixing agent and preparation method thereof |
| CN110331605B (en) * | 2019-07-19 | 2021-10-08 | 绍兴中纺化工有限公司 | Natural dye color fixing agent and preparation method thereof |
| CN111138662A (en) * | 2020-01-08 | 2020-05-12 | 广东德美精细化工集团股份有限公司 | Preparation method and application of active hydrophilic formaldehyde-free color fixing agent |
| CN111138662B (en) * | 2020-01-08 | 2022-04-29 | 广东德美精细化工集团股份有限公司 | Preparation method and application of active hydrophilic formaldehyde-free color fixing agent |
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