CN119490661B - Antibacterial moisture absorbing softener and preparation method thereof - Google Patents

Antibacterial moisture absorbing softener and preparation method thereof Download PDF

Info

Publication number
CN119490661B
CN119490661B CN202411608335.1A CN202411608335A CN119490661B CN 119490661 B CN119490661 B CN 119490661B CN 202411608335 A CN202411608335 A CN 202411608335A CN 119490661 B CN119490661 B CN 119490661B
Authority
CN
China
Prior art keywords
parts
silicone oil
antibacterial
polyoxyethylene ether
preparing
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Active
Application number
CN202411608335.1A
Other languages
Chinese (zh)
Other versions
CN119490661A (en
Inventor
徐炜
杨振
皮碧荣
李冰林
张瑞
穆珊
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Ningbo Runhe High Tech Material Co ltd
Original Assignee
Ningbo Runhe High Tech Material Co ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Ningbo Runhe High Tech Material Co ltd filed Critical Ningbo Runhe High Tech Material Co ltd
Priority to CN202411608335.1A priority Critical patent/CN119490661B/en
Publication of CN119490661A publication Critical patent/CN119490661A/en
Application granted granted Critical
Publication of CN119490661B publication Critical patent/CN119490661B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/42Block-or graft-polymers containing polysiloxane sequences
    • C08G77/46Block-or graft-polymers containing polysiloxane sequences containing polyether sequences
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/643Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
    • D06M15/657Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain containing fluorine
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M16/00Biochemical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. enzymatic
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2101/00Chemical constitution of the fibres, threads, yarns, fabrics or fibrous goods made from such materials, to be treated
    • D06M2101/02Natural fibres, other than mineral fibres
    • D06M2101/04Vegetal fibres
    • D06M2101/06Vegetal fibres cellulosic
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2200/00Functionality of the treatment composition and/or properties imparted to the textile material
    • D06M2200/50Modified hand or grip properties; Softening compositions

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Biochemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Microbiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Abstract

本申请公开了一种抗菌吸湿柔软剂及其制备方法,其中制备方法包括以下制备步骤;S1:将甲苯二异氰酸酯和聚乙二醇在溶剂中反应,生成中间体Ⅰ;S2:中间体Ⅰ在惰性气体氛围中与四甲基二丙烯三胺反应,生成中间体Ⅱ;S3:含氢硅油、烯丙基聚氧乙烯醚、烯丙基环氧封端聚氧乙烯醚在溶剂和催化剂中进行反应,生成改性硅油;S4:将改性硅油、诺氟沙星水溶液在溶剂中进行反应,随后向反应物中加入中间体Ⅱ,反应一段时间除杂后得到抗菌吸湿柔软剂。The present application discloses an antibacterial hygroscopic softener and a preparation method thereof, wherein the preparation method comprises the following preparation steps: S1: reacting toluene diisocyanate and polyethylene glycol in a solvent to generate an intermediate I; S2: reacting the intermediate I with tetramethyldipropylenetriamine in an inert gas atmosphere to generate an intermediate II; S3: reacting hydrogen-containing silicone oil, allyl polyoxyethylene ether, and allyl epoxy-terminated polyoxyethylene ether in a solvent and a catalyst to generate a modified silicone oil; S4: reacting the modified silicone oil and a norfloxacin aqueous solution in a solvent, then adding the intermediate II to the reactant, reacting for a period of time and removing impurities to obtain the antibacterial hygroscopic softener.

Description

Antibacterial moisture-absorbing softener and preparation method thereof
Technical Field
The application relates to the field of high polymer materials, in particular to an antibacterial moisture-absorbing softener and a preparation method thereof.
Background
Along with the improvement of living standard, people pay more and more attention to the quality and quality of life, the participation degree to outdoor exercises is also higher and higher, then the diversity and the complexity of outdoor exercises environment also give people comfort and protection when the exercises are presented a difficult problem, the people need to make own protection when guaranteeing the travelling comfort constantly, and the erosion of mosquitoes or bacteria is avoided. Meanwhile, in recent years, every summer, the life comfort of people is seriously affected by continuous high-temperature weather, and if the clothing fabric has excellent moisture absorption and ventilation properties, the comfort of people in summer is greatly improved.
Although there are many products on the market that can achieve the effect of moisture absorption and quick drying, most of the products are polyether modified silicone oil and polyamide compounds, which have no improvement on the softness, smoothness and other performances of the clothing fabric, and almost have no functions of antibiosis, sterilization and the like. The washing resistance of the auxiliary agent is poor, and the moisture absorption and quick drying performance of the auxiliary agent are obviously reduced after the auxiliary agent is washed for several times.
If the outdoor fabric, the home textile fabric and the summer clothing fabric can be simultaneously provided with excellent moisture absorption and ventilation, soft and smooth effects and excellent antibacterial and sterilization effects, the method has wide market prospect. However, no finishing auxiliary agent which has moisture absorption, ventilation, antibiosis and smoothness is found in the market, in order to endow the fabric with a special function, a printing and dyeing mill generally adopts a plurality of finishing auxiliary agents for compounding or adopts multiple working procedures to endow the fabric with the performances step by step, but the compounding of the auxiliary agents needs to consider the compatibility of various auxiliary agents, and the multiple working procedures greatly aggravate the production cost and the production of waste water. Therefore, the product integrating the effects of moisture absorption, ventilation, softness, smoothness and excellent antibacterial and sterilizing effects has good market prospect.
Disclosure of Invention
The application aims to endow fabrics such as towels with antibacterial, hygroscopic and breathable effects through modification of a softening agent.
In order to achieve the aim, the application adopts the technical scheme that the antibacterial moisture absorption softener is provided and is characterized by having the following structural general formula: wherein M 1 is M 2 is
D, c, x, z, m, n are integers, and a is more than or equal to 3 and less than or equal to 5;2, d is more than or equal to 33, 57.ltoreq.c.ltoreq.61, 4.ltoreq.x 9;2-3, m-17 and n-18.
The application provides a preparation method of an antibacterial moisture absorption softener, which is characterized by comprising the following preparation steps of S1, reacting toluene diisocyanate and polyethylene glycol in a solvent to generate an intermediate I, S2, reacting the intermediate I with tetramethyl-propylene triamine in an inert gas atmosphere to generate an intermediate II, S3, reacting hydrogen-containing silicone oil, allyl polyoxyethylene ether and allyl epoxy-terminated polyoxyethylene ether in the solvent and a catalyst to generate modified silicone oil, S4, reacting the modified silicone oil and norfloxacin aqueous solution in the solvent, then adding the intermediate II into a reactant, and removing impurities after reacting for a period of time to obtain the antibacterial moisture absorption softener, wherein the structural general formula of the intermediate I is as follows:
wherein n is an integer and n is more than or equal to 13 and less than or equal to 18, and the structural general formula of the intermediate II is as follows: Wherein n is an integer and n is more than or equal to 13 and less than or equal to 18, and the modified silicone oil has the structural general formula: wherein c, x, y, z and m are integers, c is more than or equal to 57 and less than or equal to 61, x is more than or equal to 5 and less than or equal to 9;5 and y is more than or equal to 8;2 and less than or equal to 3, m is more than or equal to 13 and less than or equal to 17, and the antibacterial moisture absorption softener has the structural general formula: wherein M 1 is M 2 is
A, d, c, x, z, m, n are integers, and a is more than or equal to 3 and less than or equal to 5;2, d is more than or equal to 33, 57.ltoreq.c.ltoreq.61, 4.ltoreq.x 9;2-3, m-17 and n-18.
Preferably, the polyethylene glycol has a number average molecular weight of 600 to 800.
Preferably, the hydrogen content of the hydrogen-containing silicone oil is 0.14% -0.22%.
Preferably, the number average molecular weight of the allyl polyoxyethylene ether is 600 to 800.
Preferably, the number average molecular weight of the allyl epoxy-terminated polyoxyethylene ether is 300-500.
As a preferable mode, the step S1 specifically comprises the steps of adding 500-600 parts of toluene diisocyanate and 1200-1600 parts of polyethylene glycol into a reaction kettle provided with a stirrer, a condensation reflux and a thermometer, adding triethylamine with the total mass fraction of 0.2% -0.4%, fully stirring, heating to 60-80 ℃, and preserving heat for 4-6 hours to obtain the intermediate I.
As one preferable mode, the step S2 specifically comprises the steps of adding 1722-2122 parts of the intermediate I into a reaction kettle provided with a stirrer, a condensation reflux and a thermometer, discharging air in the reaction kettle by using inert gas, slowly dripping 300-400 parts of tetramethyl-propylene triamine into the reaction kettle, maintaining the temperature at 50-60 ℃ for 4-6 hours, adding 2096-2496 parts of isopropanol, and fully stirring to obtain the intermediate II.
As another preferable mode, the step S3 specifically comprises the steps of adding 4500-6000 parts of hydrogen-containing silicone oil, 1200-2400 parts of allyl polyoxyethylene ether and 1500-4000 parts of allyl epoxy-terminated polyoxyethylene ether into a reaction kettle provided with a stirrer, a condensation reflux and a thermometer, simultaneously adding 3300-4885 parts of isopropyl alcohol and 2-5 parts of chloroplatinic acid-isopropyl alcohol solution with the concentration of 2%, heating to 70-80 ℃ under the protection of inert gas, and preserving heat for 6-8 hours to obtain the modified silicone oil.
Further preferably, the step S4 specifically comprises the steps of adding 1100-1628 parts of modified silicone oil and 192-319 parts of norfloxacin aqueous solution with the mass ratio of 50% into a reaction kettle provided with a stirrer, a condensation reflux and a thermometer, adding 1136-1756 parts of isopropanol as a solvent, heating to 70-80 ℃, preserving heat for 6-8 hours, adding 838-1498 parts of intermediate II and 36-72 parts of acetic acid into the reaction kettle, preserving heat for 8-10 hours, and separating 1415-2252 parts of isopropanol under the condition that the vacuum negative pressure is minus 0.09 to minus 0.1Mpa to obtain the antibacterial moisture absorbent softener.
Compared with the prior art, the application has the beneficial effects that:
(1) The antibacterial moisture-absorbing softener material disclosed by the application has the advantages that the norfloxacin quinolone structure is introduced into the structure, and the synergistic effect of the norfloxacin quinolone structure, the organosilicon chain segment and the tertiary amino group can be realized, so that not only can the excellent wearing comfort performance be realized, but also the excellent antibacterial performance can be realized, and the generation of wastewater caused by considering the compatibility of various auxiliary agents and multiple processes because the multiple functions of the fabric are required to be realized is avoided;
(2) The coordination effect of the polyurethane structure, the polyamine branching structure and the polyoxyethylene ether chain segment in the product structure can endow the fabric with excellent moisture absorption and air permeability, and improve the wearing comfort of the fabric;
(3) The amino, organosilicon, carbamido and other mechanisms in the product structure and the mutual synergistic effect can give the finished fabric good wearing comfort performance, and the carbamido and carbamate structure of the polyurethane can promote the adsorption and cladding capacity to the fabric, thereby improving the washability of the fabric.
Detailed Description
The present application will be further described with reference to the following specific embodiments, and it should be noted that, on the premise of no conflict, new embodiments may be formed by any combination of the embodiments or technical features described below.
The terms "comprises" and "comprising," along with any variations thereof, in the description and claims, are intended to cover a non-exclusive inclusion, such that a process, method, system, article, or apparatus that comprises a list of steps or elements is not necessarily limited to those steps or elements but may include other steps or elements not expressly listed or inherent to such process, method, article, or apparatus.
The application provides an antibacterial, moisture-absorbing and breathable softener material, which has the following structural general formula:
wherein M 1 is M 2 is
A, d, c, x, z, m, n are integers, and a is more than or equal to 3 and less than or equal to 5;2, d is more than or equal to 33, 57.ltoreq.c.ltoreq.61, 4.ltoreq.x 9;2-3, m-17 and n-18.
The antibacterial moisture-absorbing softener has a norfloxacin quinolone structure, an organosilicon chain segment and a tertiary amine structure, not only can endow fabrics with excellent wearing comfort performance, but also can endow fabrics with excellent antibacterial performance, and also avoids the generation of wastewater caused by considering the compatibility of various auxiliary agents and multiple processes because of the requirement of endowing the fabrics with multiple functions.
The application provides a preparation method of an antibacterial moisture-absorbing softener, which comprises the following steps of:
S1, toluene diisocyanate and polyethylene glycol react in a solvent to generate an intermediate I;
s2, reacting the intermediate I with tetramethyl dipropylene triamine in an inert gas atmosphere to generate an intermediate II;
S3, reacting hydrogen-containing silicone oil, allyl polyoxyethylene ether and allyl epoxy-terminated polyoxyethylene ether in a solvent and a catalyst to generate modified silicone oil;
s4, reacting the modified silicone oil and the norfloxacin aqueous solution in a solvent, then adding an intermediate II into the reactant, and removing impurities after reacting for a period of time to obtain the antibacterial moisture-absorbing softener.
In step S1, toluene diisocyanate and polyethylene glycol are reacted as follows:
Wherein n is an integer, and n is more than or equal to 13 and less than or equal to 18.
In step S2, intermediate I is reacted with tetramethyldipropylene triamine as follows:
Wherein n is an integer, and n is more than or equal to 13 and less than or equal to 18.
In the step S3, the hydrogen-containing silicone oil, the allyl polyoxyethylene ether and the allyl epoxy-terminated polyoxyethylene ether react in a solvent and a catalyst as follows:
wherein b, c, x, y, z, m are integers, b is more than or equal to 7 and less than or equal to 11, and 57 is more than or equal to 57 c is less than or equal to 61, and x is less than or equal to 5 and less than or equal to c is less than or equal to 61, 5 x is less than or equal to.
In step S4, the modified silicone oil, norfloxacin and intermediate II react as follows:
wherein M 1 is
M 2 isA, d, c, x, y, z, m, n are integers, and a is more than or equal to 3 and less than or equal to 5;2, d is more than or equal to 33, 57.ltoreq.c.ltoreq.61, 4.ltoreq.x.ltoreq.3924; 3, 57.ltoreq.c.ltoreq.61, 4 x is more than or equal to 9;5.
The application utilizes the reaction of isocyanate groups and hydroxyl groups to prepare an intermediate I, and then utilizes the reaction of isocyanate groups and amino groups to prepare an intermediate II, and introduces tertiary amine groups capable of reacting with epoxy groups into the polyurethane structure. The structure of hydrogen-containing silicone oil is introduced with allyl polyoxyethylene ether and allyl epoxy polyether by hydrosilylation reaction. And then, introducing various functional groups into the product structure by utilizing the reaction of epoxy groups, norfloxacin, secondary amine and tertiary amine to prepare the antibacterial moisture-absorbing softener.
In some embodiments, the polyethylene glycol in step S1 has a number average molecular weight of 600 to 800.
In some embodiments, the hydrogen-containing silicone oil has a hydrogen content of 0.14% -0.22%.
In some embodiments, the allyl polyoxyethylene ether has a number average molecular weight of 600 to 800.
In some embodiments, the allyl epoxy-terminated polyoxyethylene ether has a number average molecular weight of 300 to 500.
In some embodiments, the step S1 specifically comprises the steps of adding 500-600 parts of toluene diisocyanate and 1200-1600 parts of polyethylene glycol into a reaction kettle provided with a stirrer, a condensation reflux and a thermometer, adding triethylamine accounting for 0.2% -0.4% of the total mass, fully stirring, heating to 60-80 ℃, and preserving heat for 4-6 hours to obtain an intermediate I.
In some embodiments, step S2 comprises adding 1722-2122 parts of intermediate I into a reaction kettle equipped with a stirrer, a condensation reflux and a thermometer, discharging air in the reaction kettle by using inert gas, slowly dripping 300-400 parts of tetramethyldiethylenetriamine into the reaction kettle, maintaining the temperature at 50-60 ℃ for 4-6 hours, adding 2096-2496 parts of isopropanol, and fully stirring to obtain intermediate II.
In some embodiments, the step S3 specifically comprises the steps of adding 4500-6000 parts of hydrogen-containing silicone oil, 1200-2400 parts of allyl polyoxyethylene ether and 1500-4000 parts of allyl epoxy-terminated polyoxyethylene ether into a reaction kettle provided with a stirrer, a condensation reflux and a thermometer, simultaneously adding 3300-4885 parts of isopropyl alcohol and 2-5 parts of chloroplatinic acid-isopropyl alcohol solution with the concentration of 2%, heating to 70-80 ℃ under the protection of inert gas, and preserving heat for 6-8 hours to obtain modified silicone oil.
According to the antibacterial moisture-absorbing softener structure, the polyurethane structure, the polyamine branching structure and the polyoxyethylene ether chain segment are introduced to have synergistic effect, so that excellent moisture-absorbing and air-permeable properties can be provided for the fabric, and the wearing comfort of the fabric is improved.
In some embodiments, the step S4 specifically comprises the steps of adding 1100-1628 parts of modified silicone oil and 192-319 parts of norfloxacin aqueous solution with the mass ratio of 50% into a reaction kettle provided with a stirrer, a condensation reflux and a thermometer, adding 1136-1756 parts of isopropanol as a solvent, heating to 70-80 ℃, preserving heat for 6-8 hours, adding 838-1498 parts of intermediate II and 36-72 parts of acetic acid into the reaction kettle provided with the stirrer, the condensation reflux and the thermometer, preserving heat for 8-10 hours, and separating 1415-2252 parts of isopropanol under the condition that the vacuum negative pressure is minus 0.09-0.1 Mpa to obtain the antibacterial moisture absorption softener.
The norfloxacin quinolone structure is introduced into the product structure, and the synergistic effect of the norfloxacin quinolone structure, the organosilicon chain segment and the tertiary amino group can endow the fabric with excellent wearing comfort performance, excellent antibacterial performance and the wastewater amount caused by considering the compatibility of various auxiliary agents and multiple processes because of the requirement of endowing the fabric with multiple functions.
The amino, organosilicon, carbamide and other structures in the product structure are synergistic mutually, so that the finished fabric can be endowed with good wearing comfort, and the carbamide and carbamate structure of the polyurethane can improve the adsorption and cladding capacity to the fabric, thereby improving the washability of the fabric.
Example 1
The preparation method of the antibacterial moisture-absorbing softener comprises the following steps of:
S1, adding 522 parts of toluene diisocyanate and 1200 parts of polyethylene glycol with the average molecular weight of 600 into a drying reaction kettle provided with a stirrer, a condensation reflux and a thermometer, adding triethylamine with the total mass fraction of 0.3%, fully stirring, heating to 70 ℃, and preserving heat for 5 hours to prepare an intermediate I;
S2, adding 1722 parts of polyurethane intermediate I into a reaction kettle provided with a stirrer, a condensation reflux and a thermometer, discharging air in the reaction kettle by utilizing nitrogen, slowly dripping 374 parts of tetramethyl-propylene triamine into the reaction kettle, maintaining the temperature at 50 ℃ for 6 hours, adding 2096 parts of isopropanol, and fully stirring to obtain an intermediate II;
S3, adding 5000 parts of hydrogen-containing silicone oil with hydrogen content of 0.14%, 1200 parts of allyl polyoxyethylene ether with average molecular weight of 600 and 1500 parts of allyl epoxy-terminated polyoxyethylene ether with average molecular weight of 300 into a reaction kettle provided with a stirrer, a condensation reflux and a thermometer, simultaneously adding 3300 parts of isopropyl alcohol and 5 parts of chloroplatinic acid-isopropyl alcohol solution with concentration of 2%, heating to 80 ℃ under the protection of nitrogen, and preserving heat for 6 hours to obtain modified silicone oil;
And S4, adding 1100 parts of modified silicone oil and 192 parts of norfloxacin aqueous solution with the mass ratio of 50% into a reaction kettle provided with a stirrer, a condensation reflux and a thermometer, adding 1136 parts of isopropanol as a solvent, heating to 80 ℃, preserving heat for 8 hours, adding 838 parts of intermediate II and 36 parts of acetic acid into the reaction kettle provided with the stirrer, the condensation reflux and the thermometer, preserving heat for 8 hours, and separating 1415 parts of isopropanol under the condition of vacuum negative pressure of-0.095 Mpa to obtain the antibacterial moisture absorption softener.
Example 2
Adjusting the polyethylene glycol in the step S1 to 1600 parts of polyethylene glycol with average molecular weight of 800;
Adjusting the adding amount of the intermediate I in the step S2 to 2122 parts, and adjusting the adding amount of isopropanol to 2496 parts;
The amount of isopropyl alcohol added in step S4 was adjusted to 1176 parts, the amount of intermediate II was adjusted to 998 parts, and finally 1500 parts of isopropyl alcohol was separated by removing impurities, and the other preparation methods were the same as those in example 1.
Example 3
Adjusting the addition amount of the allyl polyoxyethylene ether in the step S3 to 1600 parts, the number average molecular weight to 800, and the added amount of the isopropanol to 3471 parts;
The amount of the modified silicone oil added in the step S4 was adjusted to 1157 parts by mass, the amount of isopropyl alcohol as a solvent was added to 1180 parts, and 1459 parts of isopropyl alcohol was separated by removing impurities, and the other preparation methods were the same as those in the preparation method of example 1.
Example 4
Adjusting the addition amount of the allyl epoxy-terminated polyoxyethylene ether in the step S3 to 2500 parts, the number average molecular weight to 500, and the amount of added isopropanol to 3729 parts;
The amount of the modified silicone oil added in the step S4 was adjusted to 1243 parts by mass, the amount of isopropyl alcohol added as a solvent was 1244 parts, and 1523 parts of isopropyl alcohol was separated out by removing impurities, and the other preparation methods were the same as those in the preparation method of example 1.
Example 5
Adjusting the hydrogen content of the hydrogen-containing silicone oil in the step S3 to 0.22%, adjusting the addition amount of the allyl polyoxyethylene ether to 1800 parts, adjusting the addition amount of the allyl epoxy-terminated polyoxyethylene ether to 2400 parts, and adjusting the added amount of the isopropanol to 3943 parts;
The amount of modified silicone oil added in step S4 was adjusted to 1314 parts, the amount of 50% norfloxacin aqueous solution was adjusted to 319 parts, the amount of intermediate II was adjusted to 1257 parts, the amount of acetic acid was adjusted to 54 parts, and 1888 parts of isopropyl alcohol was finally separated by removing impurities, and the other preparation methods were consistent with the preparation method in example 1.
Example 6
Adjusting the addition amount of the allyl polyoxyethylene ether in the step S3 to 2400 parts, the number average molecular weight to 800, and the addition amount of the isopropyl alcohol to 4200 parts;
The amount of modified silicone oil added in the step S4 was adjusted to 1400 parts, the amount of isopropyl alcohol solvent was adjusted to 1526 parts, and 1952 parts of isopropyl alcohol was separated by removing impurities, and the other preparation methods were the same as those in the preparation method of example 5.
Example 7
Adjusting the addition amount of the allyl epoxy-terminated polyoxyethylene ether in the step S3 to 4000 parts, the number average molecular weight to 500, and the amount of added isopropanol to 5629 parts;
The addition amount of the modified silicone oil in the step S4 was adjusted to 1643 parts, the addition amount of the isopropyl alcohol solvent was adjusted to 1708 parts, and 2135 parts of isopropyl alcohol was finally separated by removing impurities, and the other preparation methods were the same as those in the preparation method of example 5.
Example 8
The amount of 50% norfloxacin aqueous solution added in step S4 was adjusted to 255 parts, the amount of isopropyl alcohol solvent added was adjusted to 1580 parts, the amount of intermediate II added was adjusted to 1677 parts, the amount of acetic acid added was adjusted to 72 parts, and 2100 parts of isopropyl alcohol was separated by removing impurities, and the other preparation methods were the same as those in example 5.
Example 9
The heat-preservation time after adding the isopropanol solvent in the step S4 was adjusted to 10 hours, and other preparation methods were consistent with the preparation method in example 5.
Example 10
The mode time after the addition of intermediate II in step S4 was adjusted to 10 hours, and the other preparation modes were consistent with the preparation method in example 5.
Comparative example 1
The other preparation was identical to the preparation in example 5, except that tetramethylhexamethylenediamine was used in step S4 instead of 50% aqueous norfloxacin.
Comparative example 2
Instead of preparing intermediate II, the reaction of step S3 and step S4 was performed using tetramethyldiethylenetriamine instead of intermediate II, and the other preparation method was consistent with the preparation method in example 5.
Comparative example 3
The polyethylene glycol in step S1 was replaced by polypropylene glycol, and the other preparation methods were the same as those in example 5.
Comparative example 4
The tetramethyldipropylene triamine in the step S2 was replaced with dimethylpropylene diamine, and the other preparation method was the same as in example 5.
Comparative example 5
Commercially available silicone oil 1 for cotton was purchased.
Comparative example 6
Commercially available silicone oil 2 for cotton was purchased.
Performance detection
And finishing process, namely padding the cotton knitted fabric with 60g/L of the softening agent prepared in each example and each comparative example, wherein the padding rate is 80%, then pre-baking the cotton knitted fabric at 170 ℃ for 45-60 s, and performing performance test evaluation on the fabric.
1. Softness test according to GB/T18318 "determination of textile and Fabric bending Length", an elongated sample is taken and placed on a platform, a ruler is pressed against the sample, and the long axis of the sample is parallel to the length direction of the ruler. The ruler and the long axis direction of the sample move on the platform at the same time, so that the part of the sample extending out of the platform is suspended and bent under the dead weight. When the downward bent tip of the specimen touches a slope at 41.5 ℃ from the horizontal, 1/2 of the specimen's extension length is the bent length. The flexural rigidity of the test specimen was calculated from the bending length and the mass per unit area.
The samples are respectively 6 warp and weft knitted with 25mm x 25mm, each sample is measured for 4 times, and an average value is obtained;
flexural rigidity calculation:
G=mC310-2
Wherein G is the bending rigidity of unit width, mN cm, m is the mass of unit area of the sample, G/m 2, and C is the average bending length of the sample, cm.
2. Moisture permeability evaluation is carried out according to GB/T12704.1-2009 "moisture permeability test method of textile fabrics first part: moisture absorption method". The moisture permeability WVT value is characterized, and the larger the value is, the better the moisture permeability of the fabric is.
3. Air permeability evaluation according to GB/T5453-1997 determination of air permeability of textile fabrics, the larger the value, the better the air permeability of the fabric.
4. And (3) evaluating the hydrophilicity, namely dripping one drop of water from a height of 2cm from the cloth cover by using a standard dropper (25 drops/mL), testing the time for finishing water absorption of the fabric under static conditions, dripping more than 3 times at different positions, and taking an average value.
5. Wash fastness evaluation washing was performed according to GB/T8629-2017 household washing and drying procedure for textile test, and the hydrophilicity and hand feel of the washed fabrics were tested.
6. And (3) evaluating the hand feeling, namely evaluating the comprehensive hand feeling by a touch method, adopting a 1-5-score evaluation method, evaluating the worst 1-score, the best 5-score and simultaneously evaluating 10 persons, and taking an average value.
7. Antibacterial Effect evaluation antibacterial Performance evaluation test was performed by referring to the test method for antibacterial Property of fabrics (FZ/T01021-1992), and was evaluated by percentage reduction of bacteria.
The results of the above 1 to 6 performance evaluation tests are recorded in table 1 below, and the antibacterial effect evaluation is recorded in table 2 below.
Table 1 results of performance testing of examples and comparative examples
According to the antibacterial moisture absorption softener, the softness, the air permeability and the moisture absorption of cotton knitted fabrics can be better improved by analyzing the performance test results of the examples 1-10, the handfeel comfort of cloth is effectively improved, and good hydrophilic performance and handfeel can be maintained after washing for a plurality of times.
The performance test results of examples 1 to 4 are analyzed, the number average molecular weight of polyethylene glycol, allyl polyoxyethylene ether and allyl epoxy-terminated polyoxyethylene ether are respectively adjusted in the preparation process, and the product finally endows the fabric with increased air permeability and moisture permeability, but the hand feeling is reduced to a certain extent.
Compared with the performance test results of the example 1 and the example 5, the example 5 adjusts the hydrogen content of the hydrogen-containing silicone oil, is beneficial to the introduction of polyether chain segments and amino groups, can remarkably improve the softness, air permeability and moisture permeability of fabrics, and improves the hand feeling.
Analytical examples 5 to 7, the number average molecular weights of the allyl polyoxyethylene ether and the allyl epoxy-terminated polyoxyethylene ether were adjusted, respectively, and although the hydrophilic performance of the fabric was slightly improved, the softness performance of the fabric was correspondingly reduced.
Analysis of examples 5 and 8, the mass ratio of norfloxacin to intermediate II was adjusted to obtain a cloth having better softness, and the air permeability, moisture permeability and hydrophilicity of the cloth were also excellent.
Analysis example 5 and example 9~1 example 10, the change in reaction time had some effect on the product properties, but the effect was still within acceptable limits and the significance of adjusting the reaction conditions was insignificant.
According to the antibacterial moisture absorption softener disclosed by the application, a tetramethyl-dipropylene triamine structure, a polyurethane structure and a polyoxyethylene structure are introduced into the antibacterial moisture absorption softener structure, and the antibacterial moisture absorption softener structure, the performance test results of the example 5 and the comparative examples 3-4 are analyzed, and the antibacterial moisture absorption softener is mutually influenced, so that excellent washing resistance, air permeability and moisture permeability can be provided for products.
Table 2 resistance properties of each example and each comparative example
As can be seen from the antibacterial results of the raw cloth, examples 1-10 and comparative examples 5-6, the raw cloth does not have antibacterial rate, and the bacteria are not beneficial to human health after long-term use. Two types of clothes treating agents sold on the market have certain antibacterial property in an initial state, but after clothes are washed for 10 times, the antibacterial property is reduced to 0.
The antibacterial moisture-absorbing softener can effectively inhibit the reproduction of escherichia coli and staphylococcus aureus, has a good antibacterial effect after being washed for a plurality of times, is suitable for being applied to clothes such as human body wearing, has comfort and simultaneously inhibits the reproduction of bacteria.
In comparison of the antibacterial effects of examples 1 to 10, the clothes treated in example 5 obtained the best bacterial inhibition rate, the inhibition rate of which to E.coli was 92.54%, the inhibition rate of which to E.coli was 86.54% after 10 times of washing, the inhibition rate of which to Staphylococcus aureus was 94.33%, and the inhibition rate of E.coli of 84.31 after 10 times of washing.
The antibacterial test results of example 5 and comparative example 1 were analyzed, and although the comparative example 1 and example 1 showed less difference in softness, breathability, hydrophilicity, hand and the like among the results presented in table 1, the antibacterial performance test results of table 2 indicate that the antibacterial performance of the treated laundry was poor by using another structure instead of the norfloxacin structure in comparative example 1.
As can be seen from the antibacterial test results of the analysis examples 5 and the comparison examples 2 to 4, the synergistic effect of the quaternary ammonium salt group of norfloxacin and tetramethyl-bisacryltriamine is introduced into the product structure, so that the excellent antibacterial effect can be given to the fabric. Meanwhile, the synergistic effect of polyurethane, ureido structure and amino group introduced in the structure can improve the washing durability of the product.
The antibacterial moisture-absorbing softener can be applied to clothes treatment to improve the softness, air permeability and moisture permeability, hydrophilic performance and hand feeling of the clothes, endow the fabrics with excellent bacteria inhibition performance and washing durability, and can not generate a large amount of waste water which is difficult to treat in the production process, so that the antibacterial moisture-absorbing softener has certain economic adaptability.
The foregoing has outlined the basic principles, features, and advantages of the present application. It will be understood by those skilled in the art that the present application is not limited to the embodiments described above, and that the above embodiments and descriptions are merely illustrative of the principles of the present application, and various changes and modifications may be made therein without departing from the spirit and scope of the application, which is defined by the appended claims. The scope of the application is defined by the appended claims and equivalents thereof.

Claims (10)

1.一种抗菌吸湿柔软剂,其特征在于,其结构通式为:1. An antibacterial hygroscopic softener, characterized in that its general structural formula is: 其中M1 Where M1 is M2d,c,x,z,m,n均为整数,且3≤a≤5;2≤d≤3;57≤c≤61;4≤x≤9;2≤z≤3;13≤m≤17;13≤n≤18。 M2 is d, c, x, z, m, n are all integers, and 3≤a≤5; 2≤d≤3; 57≤c≤61; 4≤x≤9; 2≤z≤3; 13≤m≤17; 13≤n≤18. 2.一种抗菌吸湿柔软剂的制备方法,其特征在于,包括以下制备步骤:2. A method for preparing an antibacterial hygroscopic softener, characterized in that it comprises the following preparation steps: S1:将甲苯二异氰酸酯和聚乙二醇在溶剂中反应,生成中间体Ⅰ;S1: reacting toluene diisocyanate and polyethylene glycol in a solvent to generate intermediate Ⅰ; S2:所述中间体Ⅰ在惰性气体氛围中与四甲基二丙烯三胺反应,生成中间体Ⅱ;S2: the intermediate I reacts with tetramethyldipropylenetriamine in an inert gas atmosphere to generate intermediate II; S3:含氢硅油、烯丙基聚氧乙烯醚、烯丙基环氧封端聚氧乙烯醚在溶剂和催化剂中进行反应,生成改性硅油;S3: hydrogen-containing silicone oil, allyl polyoxyethylene ether, and allyl epoxy-terminated polyoxyethylene ether react in a solvent and a catalyst to generate modified silicone oil; S4:将所述改性硅油、诺氟沙星水溶液在溶剂中进行反应,随后向反应物中加入所述中间体Ⅱ,反应一段时间除杂后得到所述抗菌吸湿柔软剂;S4: reacting the modified silicone oil and the norfloxacin aqueous solution in a solvent, then adding the intermediate II to the reactant, reacting for a period of time and removing impurities to obtain the antibacterial hygroscopic softener; 所述中间体Ⅰ的结构通式为:其中n为整数,且13≤n≤18;The general structural formula of the intermediate I is: Where n is an integer and 13≤n≤18; 所述中间体Ⅱ的结构通式为:The general structural formula of the intermediate II is: 其中n为整数,且13≤n≤18; Where n is an integer and 13≤n≤18; 所述改性硅油的结构通式为:其中c,x,y,z,m均为整数,且57≤c≤61;5≤x≤9;5≤y≤8;2≤z≤3;13≤m≤17;The general structural formula of the modified silicone oil is: Where c, x, y, z, m are all integers, and 57≤c≤61; 5≤x≤9; 5≤y≤8; 2≤z≤3; 13≤m≤17; 所述抗菌吸湿柔软剂的结构通式为:The general structural formula of the antibacterial hygroscopic softener is: 其中M1M2Where M1 is M2 is a,d,c,x,z,m,n均为整数,且3≤a≤5;2≤d≤3;57≤c≤61;4≤x≤9;2≤z≤3;13≤m≤17;13≤n≤18。 a, d, c, x, z, m, n are all integers, and 3≤a≤5; 2≤d≤3; 57≤c≤61; 4≤x≤9; 2≤z≤3; 13≤m≤17; 13≤n≤18. 3.如权利要求2所述的抗菌吸湿柔软剂的制备方法,其特征在于,所述聚乙二醇的数均分子量为600~800。3. The method for preparing an antibacterial hygroscopic softener according to claim 2, wherein the number average molecular weight of the polyethylene glycol is 600-800. 4.如权利要求2所述的抗菌吸湿柔软剂的制备方法,其特征在于,所述含氢硅油的含氢量为0.14%~0.22%。4. The method for preparing an antibacterial hygroscopic softener according to claim 2, wherein the hydrogen content of the hydrogen-containing silicone oil is 0.14% to 0.22%. 5.如权利要求2所述的抗菌吸湿柔软剂的制备方法,其特征在于,所述烯丙基聚氧乙烯醚数均分子量为600~800。5. The method for preparing an antibacterial hygroscopic softener according to claim 2, wherein the number average molecular weight of the allyl polyoxyethylene ether is 600-800. 6.如权利要求2所述的抗菌吸湿柔软剂的制备方法,其特征在于,所述烯丙基环氧封端聚氧乙烯醚数均分子量为300~500。6. The method for preparing an antibacterial hygroscopic softener according to claim 2, wherein the number average molecular weight of the allyl epoxy-terminated polyoxyethylene ether is 300 to 500. 7.如权利要求2所述的抗菌吸湿柔软剂的制备方法,其特征在于,按质量份计,所述S1步骤具体为:将500~600份所述甲苯二异氰酸酯和1200~1600份所述聚乙二醇加入到装有搅拌器、冷凝回流和温度计的反应釜中,并加入总质量分数0.2%~0.4%的三乙胺,充分搅拌,升温至60~80℃,保温4~6小时,制得所述中间体Ⅰ。7. The method for preparing an antibacterial hygroscopic softener according to claim 2, characterized in that, in parts by mass, the step S1 is specifically as follows: 500-600 parts of the toluene diisocyanate and 1200-1600 parts of the polyethylene glycol are added to a reaction kettle equipped with a stirrer, condensation reflux and a thermometer, and 0.2%-0.4% of triethylamine is added in a total mass fraction, stirred sufficiently, heated to 60-80°C, and kept warm for 4-6 hours to obtain the intermediate I. 8.如权利要求2所述的抗菌吸湿柔软剂的制备方法,其特征在于,按质量份计,所述S2步骤具体为:将1722~2122份所述中间体Ⅰ加入到装有搅拌器、冷凝回流和温度计的反应釜中,利用惰性气体将反应釜中的空气排出后,将300~400份所述四甲基二丙烯三胺缓慢滴加到反应釜中,维持温度在50~60℃保温4~6小时后,加入2096~2496份异丙醇,充分搅拌,得到所述中间体Ⅱ。8. The method for preparing an antibacterial hygroscopic softener according to claim 2, characterized in that, by weight, the step S2 is specifically as follows: 1722 to 2122 parts of the intermediate I are added to a reaction kettle equipped with a stirrer, a condenser reflux and a thermometer, and after the air in the reaction kettle is discharged by an inert gas, 300 to 400 parts of the tetramethyldipropylenetriamine are slowly added dropwise to the reaction kettle, and after maintaining the temperature at 50 to 60° C. for 4 to 6 hours, 2096 to 2496 parts of isopropanol are added and stirred sufficiently to obtain the intermediate II. 9.如权利要求2所述的抗菌吸湿柔软剂的制备方法,其特征在于,按质量份计,所述S3步骤具体为:将4500~6000份所述含氢硅油、1200~2400份所述烯丙基聚氧乙烯醚、1500~4000份所述烯丙基环氧封端聚氧乙烯醚加入到装有搅拌器、冷凝回流和温度计的反应釜中,同时加入3300~4885份异丙醇和2~5份的浓度为2%的氯铂酸-异丙醇溶液,在惰性气体的保护下,升温70~80℃,保温6~8小时,得到所述改性硅油。9. The method for preparing an antibacterial hygroscopic softener according to claim 2, characterized in that, in parts by mass, the step S3 is specifically as follows: 4500-6000 parts of the hydrogen-containing silicone oil, 1200-2400 parts of the allyl polyoxyethylene ether, and 1500-4000 parts of the allyl epoxy-terminated polyoxyethylene ether are added to a reaction kettle equipped with a stirrer, condensation reflux and a thermometer, and 3300-4885 parts of isopropanol and 2-5 parts of a 2% chloroplatinic acid-isopropanol solution are added at the same time, and under the protection of an inert gas, the temperature is raised to 70-80° C. and kept warm for 6-8 hours to obtain the modified silicone oil. 10.如权利要求2所述的抗菌吸湿柔软剂的制备方法,其特征在于,按质量份计,所述S4步骤具体为:将1100~1628份所述改性硅油和192~319份质量占比为50%的所述诺氟沙星水溶液加入到装有搅拌器、冷凝回流和温度计的反应釜中,加入1136~1756份异丙醇作为溶剂,升温至70~80℃,保温6~8小时,然后将838~1498份所述中间体Ⅱ和36~72份乙酸加入到装有所述反应釜中,保温8~10小时后,在真空负压为-0.09~-0.1Mpa条件下,分离出1415~2252份所述异丙醇,得到所述抗菌吸湿柔软剂。10. The method for preparing an antibacterial hygroscopic softener according to claim 2, characterized in that, in parts by mass, the step S4 is specifically as follows: adding 1100-1628 parts of the modified silicone oil and 192-319 parts of the norfloxacin aqueous solution (50% by mass) into a reaction kettle equipped with a stirrer, condensation reflux and a thermometer, adding 1136-1756 parts of isopropanol as a solvent, heating to 70-80°C, keeping the temperature for 6-8 hours, then adding 838-1498 parts of the intermediate II and 36-72 parts of acetic acid into the reaction kettle, keeping the temperature for 8-10 hours, and separating 1415-2252 parts of the isopropanol under a vacuum negative pressure of -0.09 to -0.1 MPa to obtain the antibacterial hygroscopic softener.
CN202411608335.1A 2024-11-12 2024-11-12 Antibacterial moisture absorbing softener and preparation method thereof Active CN119490661B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN202411608335.1A CN119490661B (en) 2024-11-12 2024-11-12 Antibacterial moisture absorbing softener and preparation method thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN202411608335.1A CN119490661B (en) 2024-11-12 2024-11-12 Antibacterial moisture absorbing softener and preparation method thereof

Publications (2)

Publication Number Publication Date
CN119490661A CN119490661A (en) 2025-02-21
CN119490661B true CN119490661B (en) 2025-05-16

Family

ID=94620906

Family Applications (1)

Application Number Title Priority Date Filing Date
CN202411608335.1A Active CN119490661B (en) 2024-11-12 2024-11-12 Antibacterial moisture absorbing softener and preparation method thereof

Country Status (1)

Country Link
CN (1) CN119490661B (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN120192534B (en) * 2025-03-21 2025-09-12 宁波润禾高新材料科技股份有限公司 Anti-mosquito fabric finishing agent, preparation method and application thereof
CN120383735B (en) * 2025-05-12 2026-01-30 宁波润禾高新材料科技股份有限公司 Softener used in same bath with waterproof agent, preparation method and application thereof

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2001278995A (en) * 2000-03-31 2001-10-10 Osaka Gas Co Ltd Antibacterial linear material
CN104892893A (en) * 2015-06-29 2015-09-09 鹤山市鹤威科技发展有限公司 Polyurethane cushion material with anti-bacterial function and preparation method and application thereof

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2637173C (en) * 2006-01-31 2015-12-01 Tyco Healthcare Group Lp Super soft foams
WO2013103537A1 (en) * 2012-01-04 2013-07-11 Momentive Performance Materials Inc. Silicone adhesive compositions
CN109923151B (en) * 2016-11-03 2021-08-20 3M创新有限公司 Silicone copolymer, preparation method and article

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2001278995A (en) * 2000-03-31 2001-10-10 Osaka Gas Co Ltd Antibacterial linear material
CN104892893A (en) * 2015-06-29 2015-09-09 鹤山市鹤威科技发展有限公司 Polyurethane cushion material with anti-bacterial function and preparation method and application thereof

Also Published As

Publication number Publication date
CN119490661A (en) 2025-02-21

Similar Documents

Publication Publication Date Title
CN119490661B (en) Antibacterial moisture absorbing softener and preparation method thereof
CN105542153B (en) A kind of preparation method of polyamide polyether organosilicon ternary polymerization type hydrophilic finishing agent
KR101578569B1 (en) Deodorizing material
CN107237143B (en) A kind of anti-ultraviolet softening agent for textiles, preparation method and application thereof
CN105755837B (en) A kind of preparation method of quaternised modified amino-silicone oil softener and application
CN116410471B (en) Washable hydrophilic polysiloxane material, preparation method and application thereof
CN112709073A (en) Graphene modified non-woven fabric and preparation method thereof
CN108330694A (en) A kind of antibacterial for cotton fabric and hydrophilic soft finishing agent and preparation method thereof
CN118685993B (en) Antibacterial breathable fabric and preparation process thereof
CN111155317B (en) Chlorine-resistant hydrophilic softener and preparation method and application thereof
CN117265737B (en) Breathable antibacterial fabric
CN119711159A (en) Antibacterial crease-resistant clothing fabric and preparation process thereof
CN117166113A (en) Antibacterial skin-friendly fabric
CN110904687B (en) Pure cotton satin fabric imitated silk finishing agent and preparation method thereof
CN108530635B (en) Method for preparing quaternary ammonium salt end-capped hydrophilic block silicone oil
Shih et al. Synthesis of a polyurethane–chitosan blended polymer and a compound process for shrink‐proof and antimicrobial woolen fabrics
CN115787307A (en) Organic silicon finishing agent based on hydrophilic group modification and preparation method thereof
CN118835471B (en) A kind of formaldehyde-removing composite functional fiber cotton and its preparation method and application
EP3253915B1 (en) Alkoxylated polyethyleneimine hydrophilically-modified fibers
Zhu et al. Shape memory fiber spun with segmented polyurethane ionomer
CN116657409B (en) Preparation process and application of dry and comfortable pure cotton non-woven fabric
CN116478359B (en) Polysiloxane material for preventing jean fabric from losing elasticity, preparation method and application
CN107475861A (en) A kind of preparation method of the stretch-proof fabric containing chitosan
CN118667112A (en) Preparation method of polyurea modified organosilicon emulsion
CN116043544B (en) Dip dyeing agent for improving cold feel and anti-ultraviolet function of fabric as well as preparation method and application thereof

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
GR01 Patent grant
GR01 Patent grant