CN113355919B - Application of multifunctional cationic modifier in modification of cellulose material - Google Patents

Application of multifunctional cationic modifier in modification of cellulose material Download PDF

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CN113355919B
CN113355919B CN202110785020.4A CN202110785020A CN113355919B CN 113355919 B CN113355919 B CN 113355919B CN 202110785020 A CN202110785020 A CN 202110785020A CN 113355919 B CN113355919 B CN 113355919B
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multifunctional
modifier
reaction kettle
cellulosic
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CN113355919A (en
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毛应明
张开志
俞建敏
张田林
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Jiangsu Ocean University
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    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/61—Polyamines polyimines
    • 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
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2101/00—Chemical constitution of the fibres, threads, yarns, fabrics or fibrous goods made from such materials, to be treated
    • D06M2101/02—Natural fibres, other than mineral fibres
    • D06M2101/04—Vegetal fibres
    • D06M2101/06—Vegetal fibres cellulosic

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Abstract

The invention provides an application of a multifunctional cation modifier in modification of a cellulose material, wherein the multifunctional cation modifier is prepared by taking organic diamine, acrylic ester and epoxy chloropropane as raw materials, and a molecular structure of the multifunctional cation modifier contains a plurality of epoxy groups and a plurality of chloropropyl groups, so that the high cation grafting efficiency of the multifunctional cation modifier on the cellulose material is ensured; the multifunctional cation modifier is an oligomer of quaternary ammonium salt, the carried cation charge is rich, and the surface cation substitution degree of the modified cellulose material prepared from the multifunctional cation modifier is high.

Description

Application of multifunctional cationic modifier in modification of cellulose material
Technical Field
The invention relates to an application of a cation modifier in modification of cellulose materials, in particular to an application of poly (ethylene glycol) chain, hydrophobic alkyl, polyepoxy and poly (3-chloro-2-hydroxypropyl) polyquaternary ammonium salt in modification of cellulose fibers or cellulose fabrics, belonging to the technical field of dyeing and finishing.
Background
Dyeing of cellulosic fibres or fabrics with reactive dyes is a common method for improving the soaping fastness of said fibres or fabrics, but generally the cellulosic fibres or fabrics are negatively charged during the dyeing bath, while most of the reactive dyes used for dyeing cellulosic fibres and fabrics are anionic, and the rate of exhaustion of the reactive dyes on cellulosic fibres and fabrics is not high due to electrostatic repulsion. The method for solving the problem is to use a large amount of salt as an accelerating agent, for example, the mass percentage concentration of sodium sulfate reaches 4-16%; meanwhile, after dyeing, alkali is added for color fixation; after finishing dyeing and finishing, a large amount of water is needed for cleaning. Therefore, the reactive dyeing process of the cellulose fiber and the fabric generates a large amount of wastewater with high salt content, alkali content and high chroma, and the wastewater treatment load is serious.
Cationic modification of cellulose fibers and fabrics is one of ways to improve the dye uptake of reactive dyes and reduce the discharge amount of salt-containing wastewater (Ma Wei et al, dye and dye, 2004,24 (6): 340-345). In the cationization modification of the cellulose fiber fabric, small molecular N- (2,3-epoxy chloropropyl) trimethyl ammonium chloride, N- (2,3-epoxy chloropropyl) triethyl ammonium chloride, N- (2-hydroxy-3-chloropropyl) triethyl ammonium chloride or N- (2-hydroxy-3-chloropropyl) trimethyl ammonium chloride with similar functions and the like are used earlier, but because the active points (epoxy groups or chloropropyl) of the small molecular cation modifier are single and are easily damaged by water and a caustic soda catalyst, the grafting efficiency of the small molecular cation modifier on the cellulose fiber and the fabric is low, and the raw material waste is serious.
In recent years, some design studies have been conducted in order to improve the grafting efficiency of cationic modifiers onto cellulose fibers or fabrics. Representatively, US 20150210627A1 and US9657438B2 disclose bis (2-hydroxy-3-chloropropyl) dication modifiers, WO 2008/022062A1 discloses a monocationic modifier containing a triazine structure with double active or triple active groups, CN 104086511A discloses a monocationic modifier containing double active groups, CN 104086512A discloses a dication modifier containing a triazine structure with double active groups, CN108385415a prepares a tetracycloxy quaternary ammonium cationic modifier by taking ammonia, formaldehyde, dimethylamine and epichlorohydrin as raw materials, CN107574691a takes ethylenediamine as a starting material, a preparation method similar to CN108385415a is adopted to prepare a hexaepoxy group hexa quaternary ammonium cationic modifier, CN110204710a takes polyamine and cyanuric chloride as raw materials to prepare a polycycloxy multi-quaternary ammonium cationic modifier, and the cationic modifiers can be grafted on fabrics to improve the cationic efficiency by 100% and greatly improve the cationic efficiency of the fabrics; meanwhile, the cellulose fabric can be subjected to crosslinking modification, so that the crease-resistance effect of the fabric is realized.
In view of the above, a batch of bis (2-hydroxy-3-chloropropyl) quaternary ammonium salts, bis (2-hydroxy-3-chloropropyl) diquaternary ammonium salts, polyepoxy quaternary ammonium salts, diepoxy polyquaternary ammonium salts or polyepoxy polyquaternary ammonium salts has been disclosed, all of which are highly effective cellulose material cationic modifiers. The grafting efficiency of the cationic modifier to the cellulose material can be improved by increasing the number of epoxy groups or 2-hydroxy-3-chloropropyl groups in the molecular structure of the cationic modifier, the active dyeing effect of the cellulose material is enhanced, the purposes of energy saving and consumption reduction are achieved, the cellulose material can be subjected to crosslinking modification, and the effect of crease-resistant treatment of the fabric is achieved.
Based on the prior art effect and the method experience of the cation modifier and according to the actual functional requirements of people on the cellulose material in life, the inventor thinks that the hydrophobic group is introduced into the molecular structure of poly-epoxy or poly (2-hydroxy-3-chloropropyl) polyquaternary ammonium salt, so that the lasting water-resistant and waterproof performance of the cellulose material can be improved; the polyethylene glycol chain is introduced into the molecular structure of the polyepoxy or poly (3-chloro-2-hydroxypropyl) polyquaternary ammonium salt, so that the lasting softness, skin-friendly property and antistatic function of the cellulose material can be enhanced; based on the design, the invention provides a multifunctional cationic modifier applied to multifunctional modification of cellulose materials.
Disclosure of Invention
The invention provides an application of a multifunctional cationic modifier in modification of cellulose materials, which is realized by the following steps:
respectively weighing a multifunctional cation modifier and sodium hydroxide, putting the multifunctional cation modifier and the sodium hydroxide into ice water at the temperature of-10-25 ℃ to prepare functional bath liquid with the mass percent concentration of the multifunctional cation modifier of 4-8% and the mass percent concentration of the sodium hydroxide of 0.05-0.5%, after uniformly stirring, putting a cellulose material into the functional bath liquid according to the bath ratio of 1; or spraying the functional bath liquid on the surface of the cellulose material; then, the cellulose material evenly loaded with the functional bath lotion is heated and dried for 0.2 to 2 hours at the temperature of between 50 and 100 ℃, and then is washed and dried to prepare the multifunctional cation modified cellulose material;
wherein the multifunctional cationic modifier has a structure represented by a general formula (A) or a general formula (B):
Figure GDA0003831954340000021
Figure GDA0003831954340000031
wherein in the general formula (A) or the general formula (B)
Figure GDA0003831954340000032
Is selected from C 2 ～C 18 Alkylene or
Figure GDA0003831954340000033
R 1 Is selected from H or CH 3 ，R 2 Is selected from
Figure GDA0003831954340000034
n is a natural number of 2 to 200; wherein m is a natural number of 1 to 2000, R 3 Is selected from C 1 ～C 18 A hydrocarbon group of (1).
The cellulosic material refers to one of a cellulosic fiber, a cellulosic fabric, a cellulosic paperboard, or a cellulosic sheet.
The multifunctional cationic modifier is prepared by the following steps: weighing organic diamine and organic solvent in a reaction kettle, controlling the temperature of materials in the reaction kettle to be 10-90 ℃, adding acrylic ester and N into the reaction kettle under stirring 2 The protection reaction is carried out for 2 to 72 hours; controlling the temperature of the materials in the reaction kettle to be-15-65 ℃, continuously adding chloromethyl oxirane into the reaction kettle within 2-20 hours, raising the temperature of the materials in the reaction kettle to 65-95 ℃ after the chloromethyl oxirane is added, continuously reacting for 2-20 hours, and distilling to remove the organic solvent in the reaction kettle; adding a solvent into a reaction kettle to dissolve residues in the reaction kettle to prepare a saturated solution, controlling the temperature of materials in the reaction kettle to 0-25 ℃ under stirring, adding epoxy chloropropane with the mass 0.2-2 times of that of the residues, reacting for 6-60 hours, and then removing the solvent and excessive epoxy chloropropane by rotary evaporation to prepare the multifunctional cation modifier with the structure shown in the general formula (A) or the general formula (B);
wherein the organic diamine has a structure represented by the general formula (C):
Figure GDA0003831954340000035
wherein in the general formula (C)
Figure GDA0003831954340000036
Is selected from C 2 ～C 18 Alkylene or
Figure GDA0003831954340000037
Wherein m is a natural number of 1 to 2000.
The organic solvent is selected from one or more than two of chloroform, tetrahydrofuran, 1,4-dioxane, methanol, ethanol, propanol, N-butanol, isobutanol, tert-butanol, N-methylpyrrolidone, dimethyl sulfoxide, N-dimethylformamide or N, N-dimethylacetamide, and the dosage of the organic solvent is 1-10 times of the total mass of the dosages of organic diamine, acrylic ester and epichlorohydrin.
The acrylate has a structure represented by the general formula (D):
Figure GDA0003831954340000041
wherein R in the general formula (D) 1 Is selected from H or CH 3 ，R 2 Is selected from
Figure GDA0003831954340000042
Wherein m is a natural number of 1 to 2000, R 3 Is selected from C 1 ～C 18 A hydrocarbon group of (1).
The molar ratio of the organic diamine to the acrylic ester to the chloromethyl oxirane to the epichlorohydrin is 1.8-2.2, and the molar ratio of the organic diamine to the acrylic ester to the chloromethyl oxirane to the epichlorohydrin is 2.0-2.5.
The solvent is selected from one or more than two of water, epoxy chloropropane, chloroform, tetrahydrofuran, 1,4-dioxane, methanol, ethanol, propanol, N-methylpyrrolidone, dimethyl sulfoxide, N-dimethylformamide or N, N-dimethylacetamide, and the dosage of the solvent is 1-4 times of the total mass of the dosages of organic diamine, acrylic ester, chloromethyl oxirane and epoxy chloropropane.
The skilled person is familiar with: in the application of the multifunctional cationic modifier in modification of cellulose materials, the molecular structure of the multifunctional cationic modifier contains a plurality of epoxy groups and a plurality of chloropropyl groups, which is the key for ensuring high efficiency of cationic modification grafting on the cellulose materials and the key for implementing crosslinking modification on the cellulose materials to realize crease resistance of the modified cellulose materials. The multifunctional cationic modifier is a quaternary ammonium salt polymer, has rich cationic charges, and the cellulose material modified by the multifunctional cationic modifier has high cationic degree, which is the key for ensuring high dye-uptake of the modified cellulose material; according to the actual needs of people in life and production, a hydrophobic group is selectively introduced into the molecular structure of the multifunctional cationic modifier, so that the durable water-resistant and waterproof functions of the modified cellulose material can be improved; meanwhile, a polyethylene glycol chain is selectively introduced into the molecular structure of the multifunctional cationic modifier, so that the lasting softness, skin-friendly property and antistatic property of the modified cellulose material can be improved.
Detailed Description
The application of the multifunctional cationic modifier provided by the invention in the modification of cellulose materials is illustrated in detail by the following specific examples.
Example 1 preparation of multifunctional cationically modified Cotton fiber (1)
Weighing 12 g of ethylenediamine and 300 g of chloroform, mixing in a reaction kettle, controlling the temperature of a feed liquid in the reaction kettle to be 45-65 ℃, slowly adding 40 g of methyl methacrylate, and continuously stirring and reacting for 6 hours after the feeding is finished; then reducing the temperature of the feed liquid in the reaction kettle to 0-10 ℃, dripping 40 g of epoxy chloropropane, raising the temperature in the reaction kettle to 25 ℃ after the feeding is finished, and continuously stirring for reaction for 2 hours; then raising the temperature in the reaction kettle to 70-90 ℃ for reaction for 3 hours, then lowering the temperature of the materials in the reaction kettle to 5-10 ℃, adding 120 g of epichlorohydrin, keeping the temperature, stirring and reacting for 12 hours, and then carrying out rotary evaporation to remove chloroform and redundant epichlorohydrin so as to prepare 128 g of light brown pasty multifunctional cation modifier (1).
Weighing 128 g of multifunctional cationic modifier (1) and dissolving the multifunctional cationic modifier (1) in 2500 g of ice water, adding 45 g of sodium hydroxide aqueous solution with the mass percentage concentration of 30% to prepare modifier bath liquid (1), uniformly mixing, feeding the mixture into a bath dye vat, adding 60 cotton fibers into the modifier (1) bath liquid according to the bath ratio of 1And (2) carrying out medium rolling, wherein the liquid carrying rate after rolling is 80%, then baking the cotton fiber at the temperature of 60-70 ℃ for 1 hour, and then washing and airing to obtain the multifunctional cation modified cotton fiber (1). Cotton fiber modified by multifunctional cations according to Kjeldahl method (1) The nitrogen content is analyzed, and the result shows that the nitrogen content is 0.07362% by mass and the grafting efficiency is 97.3%.
Example 2 preparation of multifunctional cationic modified Cotton cloth (1)
Following the procedure and procedure of example 1, a multifunctional cationic modified cotton cloth (1) was prepared by replacing ethylenediamine with 1,6-hexanediamine, methyl methacrylate with methoxypolyethylene glycol-400 methacrylate and 60 cotton fibers with cotton, and the grafting efficiency was calculated to be 95.7%.
Example 3 preparation of multifunctional cationic modified Cotton cloth (2)
According to the preparation method and the operation steps of example 1, the multifunctional cationic modified cotton cloth (2) is prepared by changing ethylenediamine to 1,6-hexanediamine, methyl methacrylate to lauryl methacrylate and 60 cotton fibers to cotton cloth, and the grafting efficiency is calculated to be 92.5%.
EXAMPLE 4 preparation of multifunctional cationically modified white cardboard (1)
According to the preparation method and the operation steps of the example 1, the multifunctional cation modified white cardboard (1) is prepared by changing the ethylenediamine into alpha, omega-double-terminal amino polyether-400, the methyl methacrylate into methoxy polyethylene glycol-400 methacrylate and 60 cotton fibers into white cardboard, and the grafting efficiency is calculated to be 85.7%.
EXAMPLE 5 preparation of multifunctional cationic modified medical Cotton gauze (1)
According to the preparation method and the operation steps of the example 1, the multifunctional cationic modified medical cotton gauze (1) is prepared by changing the ethylenediamine into alpha, omega-double-terminal amino polyether-400, the methyl methacrylate into methoxy polyethylene glycol-400 methacrylate and 60 cotton fibers into medical cotton gauze, and the calculated grafting efficiency is 94.9%.
The above description is the preferred embodiment of the present invention, and it is within the scope of the appended claims to cover all modifications of the invention which may occur to those skilled in the art without departing from the spirit and scope of the invention.

Claims (6)

1. The application of a multifunctional cationic modifier in the modification of cellulosic materials is characterized by being realized by the following steps:
respectively weighing a multifunctional cation modifier and sodium hydroxide, putting the multifunctional cation modifier and the sodium hydroxide into ice water at the temperature of-10-25 ℃ to prepare functional bath liquid with the mass percent concentration of the multifunctional cation modifier of 4-8% and the mass percent concentration of the sodium hydroxide of 0.05-0.5%, after uniformly stirring, putting a cellulose material into the functional bath liquid according to the bath ratio of 1; or spraying the functional bath liquid on the surface of the cellulose material; then, the cellulose material evenly loaded with the functional bath lotion is heated and dried for 0.2 to 2 hours at the temperature of between 50 and 100 ℃, and then is washed and dried to prepare the multifunctional cation modified cellulose fiber material;
wherein the multifunctional cationic modifier has a structure represented by general formula (A) or general formula (B):
Figure FDA0003831954330000011
wherein in the general formula (A) or the general formula (B)
Figure FDA0003831954330000012
Is selected from C 2 ～C 18 Alkylene or
Figure FDA0003831954330000013
R 1 Is selected from H or CH 3 ，R 2 Is selected from
Figure FDA0003831954330000014
n is a natural number of 2 to 200; wherein m is a natural number of 1 to 2000, R 3 Is selected from C 1 ～C 18 A hydrocarbon group of (a);
the cellulosic material refers to one of a cellulosic fiber, a cellulosic fabric, a cellulosic paperboard, or a cellulosic sheet.
2. Use of a multifunctional cationic modifier according to claim 1 for the modification of cellulosic materials, characterized in that the multifunctional cationic modifier is prepared by: weighing organic diamine and organic solvent in a reaction kettle, controlling the temperature of materials in the reaction kettle to be 10-90 ℃, adding acrylic ester and N into the reaction kettle under stirring 2 The protection reaction is carried out for 2 to 72 hours; then controlling the temperature of the materials in the reaction kettle to be-15-65 ℃, continuously adding chloromethyl oxirane into the reaction kettle within 2-20 hours, raising the temperature of the materials in the reaction kettle to 65-95 ℃ after the chloromethyl oxirane is added, and continuously reacting for 2-20 hours, and distilling to remove the organic solvent in the reaction kettle; adding a solvent into a reaction kettle to dissolve residues in the reaction kettle to prepare a saturated solution, controlling the temperature of materials in the reaction kettle to 0-25 ℃ under stirring, adding epoxy chloropropane with the mass 0.2-2 times of that of the residues, reacting for 6-60 hours, and then removing the solvent and excessive epoxy chloropropane by rotary evaporation to prepare the multifunctional cation modifier with the structure shown in the general formula (A) or the general formula (B);
wherein the molar ratio of the organic diamine to the acrylic ester to the chloromethyl oxirane to the epichlorohydrin is 1.8-2.2, and is (by weight ratio) between 5 and 6;
the dosage of the organic solvent is 1 to 10 times of the total mass of the dosages of the organic diamine, the acrylic ester, the chloromethyl oxirane and the epichlorohydrin;
the dosage of the solvent is 1 to 4 times of the total mass of the dosages of the organic diamine, the acrylic ester, the chloromethyl oxirane and the epichlorohydrin.
3. Use of a multifunctional cationic modifier in the modification of cellulosic materials according to claim 2, characterized in that the organic diamine has the structure of formula (C):
Figure FDA0003831954330000021
wherein in the general formula (C)
Figure FDA0003831954330000022
Is selected from C 2 ～C 18 Alkylene or
Figure FDA0003831954330000023
Wherein m is a natural number selected from 1 to 2000.
4. Use of a multifunctional cationic modifier in the modification of cellulosic material according to claim 2, characterized in that said acrylate has the structure of formula (D):
Figure FDA0003831954330000024
wherein R in the general formula (D) 1 Is selected from H or CH 3 ，R 2 Is selected from
Figure FDA0003831954330000025
Wherein m is a natural number of 1 to 2000, R 3 Is selected from C 1 ～C 18 A hydrocarbon group of (1).
5. The use of a multifunctional cationic modifier in the modification of cellulosic materials according to claim 2, wherein the organic solvent is selected from one or more of chloroform, tetrahydrofuran, 1,4-dioxane, methanol, ethanol, propanol, N-butanol, isobutanol, t-butanol, N-methylpyrrolidone, dimethyl sulfoxide, N-dimethylformamide or N, N-dimethylacetamide.
6. The use of a multifunctional cationic modifier in the modification of cellulosic materials according to claim 2, wherein the solvent is selected from one or more of water, epichlorohydrin, chloroform, tetrahydrofuran, 1,4-dioxane, methanol, ethanol, propanol, N-methylpyrrolidone, dimethylsulfoxide, N-dimethylformamide or N, N-dimethylacetamide.
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