CN113121790B - Wet rubbing fastness improver for acid dye and preparation method thereof - Google Patents
Wet rubbing fastness improver for acid dye and preparation method thereof Download PDFInfo
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- CN113121790B CN113121790B CN202110457182.5A CN202110457182A CN113121790B CN 113121790 B CN113121790 B CN 113121790B CN 202110457182 A CN202110457182 A CN 202110457182A CN 113121790 B CN113121790 B CN 113121790B
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6633—Compounds of group C08G18/42
- C08G18/6637—Compounds of group C08G18/42 with compounds of group C08G18/32 or polyamines of C08G18/38
- C08G18/6648—Compounds of group C08G18/42 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3225 or C08G18/3271 and/or polyamines of C08G18/38
- C08G18/6655—Compounds of group C08G18/42 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3225 or C08G18/3271 and/or polyamines of C08G18/38 with compounds of group C08G18/3271
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/2805—Compounds having only one group containing active hydrogen
- C08G18/285—Nitrogen containing compounds
- C08G18/2855—Lactams
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3271—Hydroxyamines
- C08G18/3275—Hydroxyamines containing two hydroxy groups
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4236—Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic groups
- C08G18/4238—Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic groups derived from dicarboxylic acids and dialcohols
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/39—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using acid dyes
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
- D06P1/52—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing synthetic macromolecular substances
- D06P1/5264—Macromolecular compounds obtained otherwise than by reactions involving only unsaturated carbon-to-carbon bonds
- D06P1/5285—Polyurethanes; Polyurea; Polyguanides
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Abstract
The invention discloses a wet rubbing fastness improver for acid dyes and a preparation method thereof. The wet rubbing fastness improver for the acid dye is obtained by taking serinol, formic acid and formaldehyde as raw materials to synthesize a chain extender, reacting isophorone diisocyanate, polyester diol and the chain extender, blocking by adopting caprolactam, and emulsifying at a high speed. The wet rubbing fastness improver molecule provided by the invention contains a branched chain cationic structure, and can reduce molecule entanglement to improve the stability of the wet rubbing fastness improver; meanwhile, the naked cationic group is favorable for being combined with acid dye anions to form insoluble lake so as to improve wet rubbing fastness; and because the molecules of the wet rubbing fastness improver contain blocked isocyanate groups, after deblocking at a proper temperature, the wet rubbing fastness improver can generate a crosslinking effect with active groups on fibers to form a film, and the film firmly covers the fabric, so that the wet rubbing fastness of the fabric is further improved.
Description
Technical Field
The invention relates to the technical field of synthesis of textile printing and dyeing auxiliaries, and particularly relates to a wet rubbing fastness improver for acid dyes and a preparation method thereof.
Background
The traditional acid dyes generally refer to dyes containing acid groups in the molecular structure, the contained acid groups mostly exist in the forms of sulfonate and carboxylate, and the dyes are often required to be dyed under the acid condition in the early development stage, so the dyes are conventionally called acid dyes. The acid dye has the advantages of various varieties, convenient use, complete chromatogram, bright color and the like, and is commonly used for dyeing the fibers such as chinlon, silk and wool. When the acid dye is used for dyeing fabric, the non-polar part in the dye is combined with fiber by van der Waals force and hydrogen bond, and the anion part is combined with cation group such as amino group on the fabric by ionic bond. Due to the existence of a large amount of water-soluble groups, when fabrics dyed by the acid dye are washed or rubbed in water, the dye is easy to fall off from the fabrics and is dissolved in the water, so that the fabrics fade, and therefore, the wet rubbing fastness of the fabrics dyed by the acid dye is poor, and the color fastness of the fabrics needs to be improved by using a color fixing agent. The earliest acid dye fixing agents used tannic acid. In the color fixing process, tannin and dye anion groups promote dye molecules to diffuse into fibers mainly under the action of electrostatic repulsion, so that ionic bonds between the dye and the fibers are prevented from being damaged, pores dissolved out by the dye are blocked, and the dye is firmly fixed on the fabric. Although tannic acid has a good color fixing effect, the color fixing process is strict, the process is complicated, the fabric feels hard, and even color light changes, a synthetic tannin color fixing agent is gradually developed at home and abroad to replace tannic acid, the common tannin color fixing agent comprises formaldehyde phenol condensation compounds, thiophenol compounds, benzenesulfone compounds and the like, but the tannic acid color fixing agent cannot meet the market requirement gradually due to the complex synthetic process and high cost, and toxic substances such as hydrogen sulfide, formaldehyde and the like possibly exist in the synthetic process.
Therefore, the method is very important to develop a wet rubbing fastness improver which not only improves the color fixing effect, but also is environment-friendly by combining the actual condition that the wet rubbing fastness is poor due to the fact that the acid dye is easy to dissolve out in water and utilizing the excellent flexibility and film-forming property of the polyurethane.
Disclosure of Invention
Aiming at the defects in the prior art, the invention provides the improver which is safe and environment-friendly and can effectively improve the wet rubbing fastness of the fabric dyed with the acid dye and the preparation method thereof.
The technical scheme for realizing the aim of the invention is to provide a preparation method of a wet rubbing fastness improver for acid dyes, which comprises the following steps:
(1) adding 45 parts of serinol, 100-120 parts of formic acid and 80-110 parts of formaldehyde solution into a reaction vessel with a stirrer and a condensation reflux device according to parts by weight, starting the stirring and condensation reflux device, reacting for 1-2 hours at the temperature of 25-30 ℃, heating to 70-90 ℃, and carrying out heat preservation reaction for 8-12 hours; adjusting the temperature to 60-70 ℃, the pressure to-0.08 to-0.1 Mpa, and recovering water and formic acid by reduced pressure distillation; cooling to 20-25 ℃, adding sodium hydroxide to adjust the pH value to 11-12, dissolving with anhydrous methanol, filtering, and distilling the filtrate under reduced pressure at 50-60 ℃ and a pressure of-0.08 to-0.1 MPa to recover methanol to obtain a chain extender of a light yellow oily substance;
(2) mixing 100 parts of polyester diol and 10-20 parts of acetone, adding the mixture into a reaction vessel with a stirrer and a condensation reflux device, starting the condensation reflux device and the stirrer, heating to 60-80 ℃, adding 0.06-0.12 part of dibutyltin dilaurate, dropwise adding 50-75 parts of isophorone diisocyanate, finishing dropwise within 0.5-1 h, and reacting for 2-3 h at the temperature of 60-80 ℃; then adding 5-27 parts of the chain extender prepared in the step (1), adjusting the temperature to 50-60 ℃, and carrying out heat preservation reaction for 1.5-2 hours; heating to 70-80 ℃, adding 10-25 parts of caprolactam, carrying out end-capping reaction for 3-4 h, adding 6-28 parts of glacial acetic acid, carrying out reaction for 10-20 min, adjusting the temperature to 45-55 ℃, carrying out pressure to-0.08-0.1 MPa, carrying out reduced pressure distillation to recover acetone, adding 400-590 parts of deionized water, and carrying out high-speed stirring for 0.5-1 h at a rotating speed of 1500-3000 r/min to obtain the wet friction fastness improver for the acid dye.
The invention provides a preparation method of a wet rubbing fastness improver for an acid dye, which has a preferable scheme that: the polyester polyol in the step (2) is one of polyethylene glycol adipate glycol, polybutylene adipate glycol and polyhexamethylene adipate glycol, and the number average molecular weight of the polyester polyol is 1000 or 2000.
The technical scheme of the invention also comprises the wet rubbing fastness improver for the acid dye, which is obtained by the preparation method.
The technical scheme of the invention prepares the wet rubbing fastness improver for the acid dye according to the following synthetic reaction formula:
1. synthesis of chain extender
2. Synthesis of wet rubbing fastness improver
wherein-R-is:
wherein k is 2, 4 or 6; m is more than or equal to 2 and less than or equal to 5; n is more than or equal to 4 and less than or equal to 10.
The principle of the invention is as follows: the chain extender with side chain amino is prepared by taking serinol, formic acid and formaldehyde as reaction raw materials and utilizing an Eschweiler-Clarke methylation reaction mechanism; and reacting isophorone diisocyanate and polyester polyol with a self-made chain extender, then blocking by using caprolactam, and finally carrying out high-speed emulsification under an acidic condition to obtain the wet rubbing fastness improver for the acidic dye. The obtained wet rubbing fastness improver simultaneously has a cationic group and a closed isocyanate group, the cationic group is combined with dye anions to generate insoluble lake in the color fixing process, the unblocked isocyanate group is crosslinked with active groups on fiber molecules, and the formed polyurethane film firmly covers the dye on the fabric, so that the wet rubbing fastness of the dye is further improved.
Due to the application of the technical scheme, the invention has the following advantages:
1. according to the invention, serinol, formic acid and formaldehyde are adopted to prepare the chain extender with the side chain having tertiary amino, on one hand, the tertiary amino has small influence on the electron cloud density of the terminal hydroxyl in the chain extender, and the chain extension reaction rate is relatively low, so that the chain extension reaction can be smoothly carried out, and the generation of violent polymerization is reduced and the yield is improved; on the other hand, the hydrophilic groups are distributed on the polyurethane side chains, so that the entanglement of molecular chains is reduced, and the stability of the polyurethane emulsion is improved. In addition, under an acidic condition, the amido on the side chain in the molecule of the color fixing agent can be combined with hydrogen ions to be cationized, and the cationic group on the side chain is favorable for the color fixing agent to be combined with dye to form color lake, so that the wet rubbing fastness of the dye on the fabric is further improved.
2. According to the invention, caprolactam is adopted to block polyurethane, polyurethane molecules can be deblocked during high-temperature baking, and the unblocked isocyanate groups and active groups in fiber molecules can generate a crosslinking effect, so that the film forming property and the fixing capacity of the polyurethane on fibers are improved, and the polyurethane has a good fixing effect on dyes on the fibers. Because the cationic groups in the wet rubbing fastness improver prepared by the invention are positioned on the side chains, the influence on the polyurethane film-forming performance is small, and actually, the fixation effect of the color lake formed by the action of the cationic groups in polyurethane molecules and the anionic groups in dye molecules is far greater than the influence of the cationic groups on the polyurethane film-forming performance. Therefore, the invention fully utilizes the excellent crosslinking film-forming property of the blocked polyurethane to combine with anions and cations to form a laked effect, and comprehensively improves the wet rubbing fastness of the dye on the fabric.
Drawings
FIG. 1 is an IR spectrum of an acid dye wet rubbing fastness improver provided in example 1 of the present invention;
FIG. 2 is an IR spectrum of an acid dye wet rubbing fastness improver provided in example 2 of the present invention;
fig. 3 is an infrared spectrum of the wet rubbing fastness improver for acid dyes provided in example 3 of the present invention.
Detailed Description
The technical solution of the present invention is further described with reference to the accompanying drawings and the detailed description.
Example 1
(1) Adding 9.1g of serinol, 31.4g of 88% formic acid solution and 18.4g of 37% formaldehyde solution into a reaction vessel with a stirrer and a condensation reflux device, starting the stirring and condensation reflux device, reacting at 25 ℃ for 2h, gradually heating to 80 ℃, and preserving heat at the temperature for 8 h; adjusting the temperature to 70 ℃ and the pressure to-0.1 MPa, and recovering most of water and formic acid by reduced pressure distillation; cooling to 25 ℃, gradually adding sodium hydroxide to adjust the pH value to 12, dissolving with anhydrous methanol, filtering, heating the filtrate to 60 ℃, and carrying out reduced pressure distillation to recover methanol, thus obtaining the chain extender of light yellow oily matter.
(2) Mixing 20g of polyethylene glycol adipate glycol with 4g of acetone, and adding the mixture into a reaction container with a stirrer and a condensation reflux device; starting a reflux device and a stirrer, gradually heating to 70 ℃, adding 0.03g of dibutyltin dilaurate, dropwise adding 8.89g of isophorone diisocyanate, completing dropwise addition within 0.5h, and carrying out heat preservation reaction for 2h at the temperature; adding 1.45g of the chain extender prepared in the step (1), adjusting the temperature to 55 ℃, and reacting for 1.5 hours in a heat preservation manner; heating to 70 ℃, adding 2.15g of caprolactam, carrying out heat preservation reaction for 3h, adding 2.12g of glacial acetic acid, reacting for 20min, adjusting the temperature to 55 ℃, carrying out reduced pressure distillation to recover acetone, adding 75.9g of deionized water, and carrying out high-speed stirring at a rotating speed of 1500 revolutions per minute for 0.5h to obtain the wet rubbing fastness improver for the acid dye.
Referring to FIG. 1, it is an IR spectrum of the wet crockfastness improver for acid dyes used in this example. 2949 cm in the curve-1、1460 cm-1is-CH2and-CH3Peak of stretching vibration of 3333cm-1Is N-H stretching vibration peak, 1035 cm-1Is the stretching vibration peak of aliphatic amine C-N, 1149 cm-1Is the stretching vibration peak of C-O, 1724cm-1Is a C = O stretching vibration peak in carbamate, polyester polyol and cyclic amide; 1526 cm-1Is the combined action peak of amide C-N stretching vibration and N-H bending vibration, 1234 cm-1In-plane deformation vibration of the compound in the positions of amides C-N and N-H, at 2272 cm-1No-NCO absorption peak appears nearby, which indicates that-NCO is blocked by caprolactam, and the target product is synthesized.
Example 2
(1) Adding 9.1g of serinol, 31.4g of 88% formic acid solution and 18.4g of 37% formaldehyde solution into a reaction vessel with a stirrer and a condensation reflux device, starting the stirring and condensation reflux device, reacting at 25 ℃ for 2h, gradually heating to 80 ℃, and preserving heat at the temperature for 8 h; adjusting the temperature to 70 ℃ and the pressure to-0.1 MPa, and recovering most of water and formic acid by reduced pressure distillation; cooling to 25 ℃, gradually adding sodium hydroxide to adjust the pH value to 12, dissolving with anhydrous methanol, filtering, heating the filtrate to 60 ℃, and carrying out reduced pressure distillation to recover methanol, thus obtaining the chain extender of light yellow oily matter.
(2) Mixing 20g of polyethylene glycol adipate glycol with 4g of acetone, and adding the mixture into a reaction container with a stirrer and a condensation reflux device; starting a reflux device and a stirrer, gradually heating to 70 ℃, adding 0.06g of dibutyltin dilaurate, dropwise adding 11.11g of isophorone diisocyanate, completing dropwise addition within 0.5h, and carrying out heat preservation reaction for 2h at the temperature; adding 1.55g of the chain extender prepared in the step (1), adjusting the temperature to 55 ℃, and reacting for 1.5 hours in a heat preservation manner; heating to 70 ℃, adding 4.88g of caprolactam, carrying out heat preservation reaction for 3h, adding 4.74g of glacial acetic acid, reacting for 20min, adjusting the temperature to 55 ℃, carrying out reduced pressure distillation to recover acetone, adding 8.76g of deionized water, and carrying out high-speed stirring at a rotating speed of 1500 revolutions per minute for 0.5h to obtain the wet rubbing fastness improver for the acid dye.
Referring to FIG. 2, it is an IR spectrum of the wet crockfastness improver for acid dyes of this example. 2925 cm in the curve-1、1450 cm-1is-CH2and-CH33307cm-1Is N-H stretching vibration peak, 1035 cm-1Is the stretching vibration peak of aliphatic amine C-N, 1150 cm-1Is the stretching vibration peak of C-O, 1702cm-1Is a C = O stretching vibration peak in carbamate, polyester polyol and cyclic amide; 1655 cm-1Is the combined action peak of amide C-N stretching vibration and N-H bending vibration, 1235 cm-1In-plane deformation vibration of the compound in the positions of amides C-N and N-H, at 2272 cm-1No-NCO absorption peak appears nearby, which indicates that-NCO is blocked by caprolactam, and the target product is synthesized.
Example 3
(1) Adding 9.1g of serinol, 31.4g of 88% formic acid solution and 18.4g of 37% formaldehyde solution into a reaction vessel with a stirrer and a condensation reflux device, starting the stirring and condensation reflux device, reacting at 25 ℃ for 2h, gradually heating to 80 ℃, and preserving heat at the temperature for 8 h; adjusting the temperature to 70 ℃ and the pressure to-0.1 MPa, and recovering most of water and formic acid by reduced pressure distillation; cooling to 25 ℃, gradually adding sodium hydroxide to adjust the pH value to 12, dissolving with anhydrous methanol, filtering, heating the filtrate to 60 ℃, and carrying out reduced pressure distillation to recover methanol, thus obtaining the chain extender of light yellow oily matter.
(2) Mixing 20g of polyethylene glycol adipate glycol with 4g of acetone, and adding the mixture into a reaction container with a stirrer and a condensation reflux device; starting a reflux device and a stirrer, gradually heating to 70 ℃, adding 0.03g of dibutyltin dilaurate, dropwise adding 11.11g of isophorone diisocyanate, completing dropwise addition within 0.5h, and carrying out heat preservation reaction for 2h at the temperature; adding 2.17g of the chain extender prepared in the step (1), adjusting the temperature to 55 ℃, and reacting for 1.5 hours in a heat preservation manner; heating to 70 ℃, adding 3.43g of caprolactam, carrying out heat preservation reaction for 3h, adding 2.12g of glacial acetic acid, reacting for 20min, adjusting the temperature to 55 ℃, carrying out reduced pressure distillation to recover acetone, adding 85.9g of deionized water, and carrying out high-speed stirring at a rotating speed of 1500 revolutions per minute for 0.5h to obtain the wet rubbing fastness improver for the acid dye.
Referring to FIG. 3, it is an IR spectrum of the wet crockfastness improver for acid dyes of this example. 2949 cm in the curve-1、1460 cm-1is-CH2and-CH3Peak of stretching vibration of 3362cm-1Is N-H stretching vibration peak, 1035 cm-1Is the stretching vibration peak of aliphatic amine C-N, 1150 cm-1Is the stretching vibration peak of C-O, 1725cm-1Is a C = O stretching vibration peak in carbamate, polyester polyol and cyclic amide; 1529 cm-1Is the combined action peak of amide C-N stretching vibration and N-H bending vibration, 1234 cm-1In-plane deformation vibration of the compound in the positions of amides C-N and N-H, at 2272 cm-1No-NCO absorption peak appears nearby, which indicates that-NCO is blocked by caprolactam, and the target product is synthesized.
Example 4
In this embodiment, a nylon fabric is used as a sample to be treated, and the wet rubbing fastness improver for acid dyes provided in embodiments 1, 2 and 3 of the present invention is used as a color fixing finishing liquid to treat the sample.
1. Finishing process
The fabric used was: the nylon fabric dyed by the acid dye of the Kapparen B red;
the color fixing process comprises the following steps: soaking and finishing liquid (10 g/L) for 1min → double soaking and double rolling (the rolling retention rate is 80-90%) → pre-baking (90 ℃ multiplied by 1 min) → baking (160 ℃ multiplied by 2 min).
2. Test methods and standards
The method for testing the color fastness to rubbing is determined according to the method GB/T3920-.
The soaping-resistant color fastness test method is determined according to the method GB/T3921-2008 'soaping-resistant color fastness of textile color fastness test'.
The water-resistant color fastness test method is determined according to the method GB/T5713 and 2013 ' color fastness to Water and color fastness to Water ' of textiles '.
The method for testing the residual amount of formaldehyde is determined according to methods of GB/T2912.1-2009 ' determination of textiles, formaldehyde ', part 1, free and hydrolyzed formaldehyde (water extraction method) '.
The rating is respectively determined by a color-changing gray sample card and a staining gray sample card specified in GB/T250-2008.
And (3) evaluating hand feeling: and 6 professionals are taken as a group, the touch scoring is carried out on the finished fabric, the highest hand feeling evaluation is 5 points, the lowest hand feeling evaluation is 1 point, the average value of 5 scores is taken, and the higher the numerical value is, the better the softness is.
The results of the application performance test comparison of the wet rubbing fastness improver for acid dyes prepared in examples 1, 2 and 3 of the present invention before and after the treatment of the nylon fabric are shown in table 1.
TABLE 1 comparison of performance tests before and after fixation treatment of polyamide fabric
Claims (3)
1. A preparation method of a wet rubbing fastness improver for acid dyes is characterized by comprising the following steps:
(1) adding 45 parts of serinol, 100-120 parts of formic acid and 80-110 parts of formaldehyde solution into a reaction vessel with a stirrer and a condensation reflux device according to parts by weight, starting the stirring and condensation reflux device, reacting for 1-2 hours at the temperature of 25-30 ℃, heating to 70-90 ℃, and carrying out heat preservation reaction for 8-12 hours; adjusting the temperature to 60-70 ℃, the pressure to-0.08 to-0.1 Mpa, and recovering water and formic acid by reduced pressure distillation; cooling to 20-25 ℃, adding sodium hydroxide to adjust the pH value to 11-12, dissolving with anhydrous methanol, filtering, and distilling the filtrate under reduced pressure at 50-60 ℃ and a pressure of-0.08 to-0.1 MPa to recover methanol to obtain a chain extender of a light yellow oily substance;
(2) mixing 100 parts of polyester diol and 10-20 parts of acetone, adding the mixture into a reaction vessel with a stirrer and a condensation reflux device, starting the condensation reflux device and the stirrer, heating to 60-80 ℃, adding 0.06-0.12 part of dibutyltin dilaurate, dropwise adding 50-75 parts of isophorone diisocyanate, finishing dropwise within 0.5-1 h, and reacting for 2-3 h at the temperature of 60-80 ℃; then adding 5-27 parts of the chain extender prepared in the step (1), adjusting the temperature to 50-60 ℃, and carrying out heat preservation reaction for 1.5-2 hours; heating to 70-80 ℃, adding 10-25 parts of caprolactam, carrying out end-capping reaction for 3-4 h, adding 6-28 parts of glacial acetic acid, carrying out reaction for 10-20 min, adjusting the temperature to 45-55 ℃, carrying out pressure to-0.08-0.1 MPa, carrying out reduced pressure distillation to recover acetone, adding 400-590 parts of deionized water, and carrying out high-speed stirring for 0.5-1 h at a rotating speed of 1500-3000 r/min to obtain the wet friction fastness improver for the acid dye.
2. The process according to claim 1 for preparing wet crockfastness improver for acid dyes, characterized in that: the polyester diol in the step (2) is one of polyethylene glycol adipate diol, polybutylene adipate diol and polyhexamethylene adipate diol, and the number average molecular weight of the polyester diol is 1000 or 2000.
3. A wet crockfastness improver for acid dyes, obtainable by the process of claim 1.
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102432801A (en) * | 2011-09-15 | 2012-05-02 | 广东德美精细化工股份有限公司 | Lasting wet friction firmness increasing agent and preparation method thereof |
| EP2980110A1 (en) * | 2014-07-31 | 2016-02-03 | ALLNEX AUSTRIA GmbH | Aqueous polyurethane-vinyl polymer hybrid dispersions |
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| CN105732953A (en) * | 2016-04-26 | 2016-07-06 | 四川大学 | Zwitter-ion waterborne polyurethane resisting protein and microorganism adsorption |
| CN109467547A (en) * | 2018-10-29 | 2019-03-15 | 广东省微生物研究所（广东省微生物分析检测中心） | 5- dimethylamino -1,3- dioxanes -2- ketone and its preparation method and application |
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2021
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| CN102432801A (en) * | 2011-09-15 | 2012-05-02 | 广东德美精细化工股份有限公司 | Lasting wet friction firmness increasing agent and preparation method thereof |
| EP2980110A1 (en) * | 2014-07-31 | 2016-02-03 | ALLNEX AUSTRIA GmbH | Aqueous polyurethane-vinyl polymer hybrid dispersions |
| CN106661186A (en) * | 2014-07-31 | 2017-05-10 | 湛新奥地利有限公司 | Aqueous polyurethane - vinyl polymer hybrid dispersions |
| CN105418887A (en) * | 2015-12-14 | 2016-03-23 | 厦门大邦瑞达印染材料有限公司 | Anionic polyurethane color fixing agent for acid dyes as well as preparation method and application of color fixing agent |
| CN105732953A (en) * | 2016-04-26 | 2016-07-06 | 四川大学 | Zwitter-ion waterborne polyurethane resisting protein and microorganism adsorption |
| CN109467547A (en) * | 2018-10-29 | 2019-03-15 | 广东省微生物研究所（广东省微生物分析检测中心） | 5- dimethylamino -1,3- dioxanes -2- ketone and its preparation method and application |
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