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Synthesis and Application of 3 - Chloro - 2 - hydroxypropylmethyldiallylammonium Chloride

Cotton dyed dyes are reactive dyes, direct dyes, etc., which reactive dyes and cotton fibers due to the formation of covalent bonds, with other dyes can not match the color fastness. However, reactive dyes are easily hydrolyzed, and reactive groups are limited in the fiber. Therefore, the covalent bonding between dyes and cotton fibers is not sufficient, and the fixation rate of reactive dyes on fibers is not high, Fixing agent to improve color fastness. Polydimethyldiallylammonium chloride fixing agent is a kind of polyquaternium cationic dye-fixing agent, which is an ideal dye-fixing agent for cotton fabric reactive dyes. The fixing mechanism is through the cation in the structure Dye anions in the form of ionic bond insoluble lakes, but also in the fiber surface film, reducing the loss of dyes, so as to achieve a good fixing effect. In this paper, PDMDAAC was synthesized by graft copolymerization of dimethyl diallylammonium chloride (DMDAAC) and 3-chloro-2-hydroxypropylmethyldiallylammonium chloride (CHMDAAC) to introduce reactive groups , And the dye and the hydroxyl group on the fiber cross-linking, PDMDAAC membrane and fiber to enhance the binding force, to a certain extent, further improve the fixative fixation performance. At present, there are few literatures on the synthesis of 3-chloro-2-hydroxypropylmethyldiallylammonium chloride. Therefore, the synthesis of 3-chloro-2-hydroxypropylmethyldiallylammonium chloride was studied, and it was applied to the modification of polydimethyldiallylammonium chloride.

1 test

1.1 Materials and instruments

Reagents: N-methyldiallylamine, DMDAAC (industrial products, Zouping Mingxing Chemical Co., Ltd.), epichlorohydrin (analytical grade, Tianjin Yongda Chemical Ltd.), acetic acid (analytical reagent, Sinopharm Group Chemical Reagent Co., Ltd.), hydrochloric acid (analytical grade, Zhejiang Eagle Chemical Reagent Co., Ltd.), tetraphenylbenzene Sodium borate [analytical grade, Aladdin reagent (Shanghai) Co., Ltd.], Reactive Red EX-D, Reactive Green B133, Reactive Black W-NN (Industrial Products, Zhejiang Jintong New Material Co., Ltd.).

Fabric: 15tex × 15tex, 528 / 10cm × 283 / 10cm cotton combed fabric (Guangdong Esquel Textile Co., Ltd.).

(Shanghai Yakang Science and Education Equipment Co., Ltd.), DF-101S collector type thermostatic heating magnetic stirrer (Henan Province, Henan Province, Henan Province, China), a rotary evaporator RE52CS a rotary evaporator (Shanghai Yarong Biochemical Instrument Factory), DF-101S circulating water type multi-purpose vacuum pump (China) Co., Ltd.), Nicolet5700 Fourier Infrared Spectrometer (Thermo), IR-12 Infrared Dyeing Machine (Hangzhou Sanjin Technology Co., Ltd.), Y571L Friction Color Fastness Tester (Changzhou No.2 Textile Instrument Factory Co., Ltd.) SW-12A washing fastness testing machine (Wenzhou International High Detection Instrument Co., Ltd.), M-6 continuous stereotypes drying machine, P-AO / A1 rolling car (Hangzhou Kam Technology Co., Ltd.).

1.2 Synthesis of fixing agent

Synthesis of CHMDAAC

N-methyldiallylamine was weighed into a four-necked flask equipped with a stirrer, and an appropriate amount of deionized water was added, and hydrochloric acid was added dropwise to adjust pH = 7-8. Chloropropane, dropping speed and reaction temperature control reaction for a certain time. After completion of the reaction, the product was neutralized with alkali, and the product was allowed to stand for a while, and a CHMDAAC aqueous solution was separated.

1.2.2 Synthesis of PDMDAAC

The DMDAAC solution was placed in a 250 mL four-necked flask equipped with a thermometer, a stirrer and a nitrogen bubbler. A certain amount of deionized water was added while nitrogen was added to remove oxygen. The temperature was raised to 60 ° C, (Monomer weight) initiator ammonium persulfate solution, dropping time 1h, reaction 6h, cooling, get solid content of about 45% of the polymer PDMDAAC.


(DMDAAC): n (cHMDAAc) = 10: 3 was placed in a 250 mL four-necked flask equipped with a thermometer, stirrer and nitrogen purifier. Deionized water was added to remove oxygen by nitrogen bubbling, Start dropping O. (DMDAAC-CHMDAAC) with the same amount of about 45% was obtained after the reaction was carried out for 6 h at a dropping time of 1 h, and the temperature of the reaction mixture was lowered by 4% (monomer weight) initiator ammonium persulfate solution.

1.3 Application process

1.3.1 cotton fabric reactive dyeing process

The dosage of the dye is 5% (omf), the dosage of the saponin is 40g / L, the dosage of the soda is 10g / L, the liquor ratio is 1:30. The dyeing was carried out using an infrared dyeing machine.

1.3.2 fixing process

(90 ℃, 3min) and a baking (130 ℃, 3min) were prepared by a padding finishing liquid (40g / L, pH = 8 ~ 9).

1.4 Testing

CHMDAAC yield: Under normal circumstances, quaternary ammonium salt and sodium tetraphenylborate insoluble in water to generate precipitation:

1.0 mL of CHMDAAC solution was placed in an Erlenmeyer flask and diluted with water to 25 mL. The pH was adjusted to 4.5 with 1% acetic acid solution. Control the water bath temperature is 60-70 ° C, slowly dropping excess 0.1mol / L sodium tetraphenyl borate solution, and constantly shake the conical flask to make precipitation reaction. Overnight at room temperature, filtered, and vacuum dried to constant weight.

Infrared spectrum of CHMDAAC: Fourier infrared spectrometer test, the number of scans 32, resolution 4cm.

Intrinsic viscosity: The outflow time of NaC1 aqueous solution and product solution was measured with a Brookfield viscometer at (30.0 ± 0.1) ° C using 1 mol / L NaCl as a solvent, and the intrinsic viscosity (η) of the product was calculated by a one-point method.

Color fastness to rubbing: According to GB / T3920-2008 "color fastness test of textile color fastness" determination, refer to GB / T251-2008 "Textiles color fastness test to assess the use of gray-like card," the fabric Color fastness to rubbing.

Washing fastness: according to GB / T3921-2008 ((textile color fastness to wash color fastness 0 set, according to GB / T250-2oo8 << textiles color fastness test to assess the use of gray-like color card >> and GB / T251-2008 "Textiles color fastness test for the assessment of gray with the kind of card", the color fastness to washing the fabric visual rating.

2 Results and discussion

2.1CHMDAAC synthesis process optimization

2.1.1n (N-methyldiallylamine): n (epichlorohydrin)

The yield of CHMDAAC increased with the increase of N-methyldiallylamine. The yield of CHMDAAC reached the maximum at 1.05: 1, and the amount of N-methyldiallylamine was increased. The yield was not increased. Since the increase in N-methyldiallylamine favors a sufficient reaction with epichlorohydrin, thereby increasing the yield of CHMDAAC. So choose n (N - methyl diallylamine): n (epichlorohydrin) is 1.05: 1.

2.1.2 Reaction temperature

When the reaction temperature is low, the activity of N-methyldiallylamine and epichlorohydrin is low, the nucleophilic substitution reaction can not occur effectively, and the reaction is not complete within a certain time, so the yield of CHMDAAC is low; The yield of CHMDAAC increased to 86.2% at 40 ℃, and the yield of CHMDAAC decreased with the increase of temperature and the formation of by-products. When the reaction temperature is 60 ℃, the CHMDAAC is yellowish, which indicates that there are more by-products in the product. Therefore, the synthesis of CHMDAAC reaction temperature of 40 ℃ is appropriate.

2.1.3 Reaction time

The yield of CHMDAAC increased with the reaction time prolonged in 6 hours before reaction. When the reaction time was more than 6 hours, the reaction time had little effect on CHMDAAC yield. Because the reaction time is too short, N-methyldiallylamine and epichlorohydrin nucleophilic substitution reaction is not sufficient, the yield is not high; reaction reaches a certain time, the nucleophilic substitution reaction has been basically completed, the basic rate of yield constant. Therefore, the appropriate reaction time is 6h.

2.2P (DMDAAC-CHMDAAC) application performance

2.2.1 fixing performance comparison

P (DMDAAC-CHMDAAC) has a higher intrinsic viscosity η relative to PDMDAAC, indicating that the molecular weight of P (DMDAAC-CHMDAAC) has been improved. Meanwhile, P (DMDAAC-CHMDAAC) is used for color fastness to rubbing of reactive dyes The color fastness of soap was also improved to some extent because of the introduction of reactive groups on P (DMDAAC-CHMDAAC), which reacted with the hydroxyl groups on the dyestuff and the fiber, and increased the molecular weight of the polymer. The film surface of the fabric, thus to a certain extent, improve the fixing agent of the same color properties.

2.2.2 shade after the change of fabric color

The effect of DMDAAC-CHMDAAC on the shade of dyed cotton fabric was studied. The change of shade after dyeing with DMDAAC-CHMDAAC1 was tested in three reactive dyed cotton fabrics.

After dyeing and finishing by P (DMDAAC-CHMDAAC), the color of the three kinds of reactive dyed cotton fabrics changed slightly, but the change was not significant.

3 Conclusion

(1) The optimal synthesis conditions of CHMDAAC were n (N-methyldiallylamine): n (epichlorohydrin) = 1.05: 1, the reaction temperature was 40 ℃, reaction time was 6h, The yield was up to 86.2%.

(2) The free radical copolymerization of CHMDAAC and DMDAAC can effectively enhance the fixing performance of PDMDAAC, and its effect on the dyeing of reactive dyed cotton fabric will not be much affected.

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