CN120157877A - Preparation method and application of micro-crosslinking reactive guanidine durable antibacterial finishing agent - Google Patents
Preparation method and application of micro-crosslinking reactive guanidine durable antibacterial finishing agent Download PDFInfo
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- CN120157877A CN120157877A CN202510629413.4A CN202510629413A CN120157877A CN 120157877 A CN120157877 A CN 120157877A CN 202510629413 A CN202510629413 A CN 202510629413A CN 120157877 A CN120157877 A CN 120157877A
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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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
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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
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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
- D06M16/00—Biochemical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. enzymatic
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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
- 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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- 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
- D06M2101/10—Animal fibres
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Abstract
The invention discloses a preparation method and application of a micro-crosslinking reaction type guanidine durable antibacterial finishing agent, and relates to the field of high polymer material preparation, wherein the preparation method comprises the following steps of S1, adding aliphatic long-chain alkyl diamine, hexamethylenediamine and guanidine hydrochloride into a reaction container, preparing a water-soluble polyguanidine polymer with a linear structure through melt polycondensation by a gradient heating method, and preparing a polymer aqueous solution after dilution by adding water; S2, regulating the pH value of the polymer aqueous solution to 9-10.5, slowly dropwise adding epichlorohydrin at 20-25 ℃, and carrying out a heating reaction after the dropwise adding is completed to obtain the micro-crosslinking reaction type guanidine durable antibacterial finishing agent. The micro-crosslinking reaction type guanidine durable antibacterial finishing agent prepared by the preparation method has excellent antibacterial effect and washability, improves the color fastness of dyed fabrics by half or more while resisting bacteria, is a composite multifunctional antibacterial fixation finishing agent, and has good market application prospect.
Description
Technical Field
The invention relates to the technical field of high polymer material synthesis, in particular to a preparation method and application of a micro-crosslinking reaction type guanidine durable antibacterial finishing agent.
Background
With the development of modern textile technology, textiles are increasingly used in medical, sanitary and public places. The porous structure of the textile is extremely easy to pollute impurities or human body secretions, such as sebum, sweat and the like, in the production or use process, provides very good survival conditions for microorganisms, causes a large number of microorganisms to grow and reproduce, and ensures that the textile contacted with the human body becomes an important medium for breeding and transferring various microorganisms and has adverse effects on the human health. Therefore, development and research of antibacterial textiles have become urgent demands in the fields of medical protection and health.
The organic antibacterial agent for textiles is required to have the following advantages of high antibacterial efficiency, good antibacterial performance at low concentration, wide antibacterial spectrum, antibacterial activity for various microorganisms, antibacterial or bactericidal effect, capability of selecting antibacterial finishing agents with different antibacterial spectrums according to the application occasions of the textiles, good stability, relatively long-term stability of physical and chemical properties, no reaction with common textile auxiliary agents such as dyes in the application process, no influence on the physical properties and appearance of the textiles, high safety, no harm to human bodies due to chemical substances used by the organic antibacterial agent, simple application process and equipment operation, convenient processing, suitability for the requirements of the processing process, good compatibility with the requirements of the textiles, strong binding capacity and the like.
Recent researches have found that halogen-containing amino groups, quaternary ammonium groups, quaternary phosphonium groups, guanidine groups and other non-releasing cationic polymers have good antibacterial properties, are almost nontoxic to normal eukaryotic cells, and are not resistant to bacteria. The cationic antibacterial polymer containing guanidine groups has a structure similar to that of natural antibacterial peptide, has high-efficiency antibacterial property and excellent biocompatibility, and has better designability and regulation compared with the natural antibacterial polymer, compared with a single hydrogen bond formed by a cationic polymer containing halogen amino groups and quaternary ammonium (phosphine) salt groups and a bacterial cell membrane, the cationic polymer containing guanidine groups can form stronger double-tooth hydrogen bonds with carboxylate, phosphonate and sulfate on the bacterial cell membrane more efficiently, so that the cationic antibacterial polymer has higher-efficiency antibacterial property than the cationic polymer containing halogen amino groups, quaternary ammonium (phosphine) salt groups and the like. Furthermore, it has been found that guanidino-containing polymers have lower eukaryotic cytotoxicity than amine-containing polymers. Accordingly, guanidine-containing polymers have been widely used in the fields of wound dressing, textiles, drug delivery, pesticides, water treatment, and the like.
At present, the polyguanidine polymer organic antibacterial agent for textiles on the market mainly has two problems of 1. Poor washability, 2. Complex synthesis process and environmental protection of an improved technical scheme for improving washability, and the need of using an organic solvent, wherein the removal and recycling of the organic solvent are the biggest restriction factors for restricting the industrialized production and the popularization and the application of products.
Disclosure of Invention
The invention aims to provide a preparation method and application of a micro-crosslinking reaction type guanidine durable antibacterial finishing agent, so as to solve the problems in the background technology.
In order to achieve the aim, the technical scheme adopted by the invention is that the preparation method of the micro-crosslinking reaction type guanidine durable antibacterial finishing agent comprises the following steps:
s1, adding aliphatic long-chain alkyl diamine, hexamethylenediamine and guanidine hydrochloride into a reaction container, performing melt polycondensation by a gradient heating method to obtain a water-soluble polyguanidine polymer with a linear structure, and adding water for dilution to obtain a polymer aqueous solution, wherein the ratio of the sum of the molar amounts of the aliphatic long-chain alkyl diamine and the hexamethylenediamine to the molar amount of the guanidine hydrochloride is (1-1.1): 1;
s2, regulating the pH value of the polymer aqueous solution to 9-10.5, slowly dropwise adding epichlorohydrin at 20-25 ℃, and carrying out a heating reaction after the dropwise adding is completed to obtain the micro-crosslinking reaction type guanidine durable antibacterial finishing agent, wherein the mole ratio of the water-soluble poly-monoguanidine polymer to the epichlorohydrin is 1 (0.01-2.5).
In the reaction process, the reaction pH value and the epoxy chloropropane dosage are controlled to prepare a product with the following molecular structural formula:
,
where n is 10 or 12 and m is an integer from 10 to 16, which can form a micro-crosslinking with the fabric due to the formation of epoxy groups at one end of the molecular backbone.
Further, when the amount of epichlorohydrin is continuously increased, if the molar ratio of the water-soluble polyguanidine polymer to the epichlorohydrin is less than 1:2, a product with the following molecular structural formula can be prepared:
,
Wherein n is 10 or 12, m is an integer from 10 to 16, the product is formed by connecting 1 epoxy group to two ends of 1 polyguanidine polymer to form an intermediate, and 2 intermediate are formed by micro-crosslinking between epoxy groups, the product forms a longer carbon chain, the epoxy groups at the end of the product can form micro-crosslinking with the fabric, and the hydroxyl groups at the middle can also form micro-crosslinking with the fabric.
As a further optimization, the molar amount of the aliphatic long-chain alkyl diamine accounts for 10-30% of the sum of the molar amounts of the aliphatic long-chain alkyl diamine and the hexamethylenediamine.
As a further optimization, the aliphatic long-chain alkyl diamine in S1 comprises decanediamine or 1, 12-diaminododecane.
As further optimization, the step of the gradient heating method in the step S1 is that the reaction is carried out for 2-2.5h at 120 ℃, the temperature is raised every 30min with the temperature being 10 ℃ as the heating gradient, the temperature is raised to 160-180 ℃, and the reaction is carried out at 2-4 h.
As a further optimization, the polymerization degree of the water-soluble polyguanidine polymer in S1 is 10-16, preferably 15.
As a further optimization, the method for adjusting the pH value in the step S2 is to add hydrochloric acid for adjustment, and the concentration of the hydrochloric acid is 18%.
As a further optimization, the temperature rise reaction temperature in S2 is 50-70 ℃ and the reaction time is 0.5-2 h.
The invention also provides application of the micro-crosslinking reaction type guanidine durable antibacterial finishing agent, and the prepared micro-crosslinking reaction type guanidine durable antibacterial finishing agent is used for antibacterial fixation finishing of fabrics, and the antibacterial fixation finishing process comprises the steps of padding the fabrics or dipping the fabrics in an aqueous solution of the micro-crosslinking reaction type guanidine durable antibacterial finishing agent and drying, wherein the fabrics comprise cellulose fiber fabrics, protein fiber fabrics or fabrics blended or interwoven with chemical fibers by any one of the cellulose fiber fabrics and the protein fiber fabrics.
As a further optimization, the solid content of the aqueous solution of the micro-crosslinking reaction type guanidine durable antibacterial finishing agent is 20-25%, the concentration is 10-30g/L, and the drying temperature is 120-180 ℃.
Compared with the prior art, the invention has the beneficial effects that:
1. Aliphatic long-chain alkyl diamine is introduced, so that hydrophilic parts (guanidino groups) and hydrophobic parts (long-chain alkyl groups) are alternately arranged on a guanidine polymer main chain framework, and a macromolecular poly-monoguanidine polymer with hydrophilic-hydrophobic alternating amphiphilic characteristics is prepared, so that a directional and compact arrangement structure is formed, and the directional and compact arrangement structure has stronger capability of combining bacteria and better antibacterial effect;
2. The pH value of the polymerization system is controlled to react, epoxy chloropropane is dripped into the aqueous solution of the polyglucoside polymer, reactive epoxy groups are grafted and introduced, the bonding capacity of the epoxy groups with fabrics can be improved, the use level of the epoxy chloropropane is further controlled, hydroxyl groups are formed after micro-crosslinking is carried out between the intermediate products, the existence of the hydroxyl groups is matched with the epoxy groups, the micro-crosslinking bonding of a plurality of positions on a long chain structure with the fabrics can be realized, the bonding capacity is higher, and the washing fastness of the fabrics after finishing the fabrics can be effectively improved;
3. The introduction of the epoxy group enables the poly monoguanidine polymer to carry out micro-crosslinking to a certain extent, improves the film forming performance of the poly monoguanidine polymer, ensures the film forming stability by means of the combination capability of the epoxy group (or hydroxyl group) and the fabric, and can further improve the color fastness of the finished fabric;
4. The synthesis process of the invention is environment-friendly, does not need organic solvent, and has simple and mild process.
Drawings
FIG. 1 is a graph showing the thermogravimetric curve and thermogravimetric differential curve of the micro-crosslinking reaction type guanidine durable antimicrobial finish prepared in example 4 of the present invention.
Detailed Description
The following are specific examples of the present invention, and the technical solutions of the present invention are further described, but the present invention is not limited to these examples.
Example 1S 1, adding 10.02g of 1, 12-diaminododecane, 52.29g of hexamethylenediamine and 47.77g of guanidine hydrochloride into a reaction vessel, heating to 80 ℃, gradually heating to 120 ℃ for reaction for 2 hours after all reactants are molten, heating every 30: 30min with a heating gradient, heating to 160 ℃, preserving heat for reaction for 3 hours to obtain a water-soluble polyguanidine polymer with a linear structure, cooling to 100 ℃ after the reaction is finished, and adding 110.08g of deionized water to obtain a polymer aqueous solution;
S2, regulating the pH value of the polymer aqueous solution to 9, slowly dropwise adding 46.26g of epichlorohydrin at 20-25 ℃, heating to 60 ℃ after the dropwise adding is completed, and reacting for 2 hours to obtain the micro-crosslinking reaction type guanidine durable antibacterial finishing agent.
Example 2S 1, adding 18.09g of decanediamine, 48.81g of hexamethylenediamine and 47.77g of guanidine hydrochloride into a reaction vessel, heating to 80 ℃, gradually heating to 120 ℃ for reaction for 2 hours after all reactants are molten, heating every 30: 30min with a heating gradient, heating to 160 ℃, keeping the temperature for reaction for 4 hours to obtain a water-soluble polyguanidine polymer with a linear structure, cooling to 100 ℃ after the reaction is finished, and adding 114.67g of deionized water to obtain a polymer aqueous solution;
s2, regulating the pH value of the polymer aqueous solution to 9.5, slowly dropwise adding 69.39g of epichlorohydrin at 20-25 ℃, heating to 55 ℃ after the dropwise adding is completed, and reacting for 2 hours to obtain the micro-crosslinking reaction type guanidine durable antibacterial finishing agent.
Example 3S 1, adding 25.85 g of 1, 12-diaminododecane, 40.67g of hexamethylenediamine and 47.77g of guanidine hydrochloride into a reaction vessel, heating to 80 ℃, gradually heating to 120 ℃ for reaction for 2 hours after all reactants are molten, heating every 30min ℃ with a heating gradient, heating to 160 ℃ until the temperature is raised, preserving heat for reaction for 3 hours to obtain a water-soluble polyguanidine polymer with a linear structure, cooling to 100 ℃ after the reaction is finished, and adding 114.29 g deionized water to obtain a polymer aqueous solution;
S2, regulating the pH value of the polymer aqueous solution to 10, slowly dropwise adding 23.13g of epichlorohydrin at 20-25 ℃, heating to 65 ℃ after the dropwise adding is completed, and reacting for 2 hours to obtain the micro-crosslinking reaction type guanidine durable antibacterial finishing agent.
Example 4S 1, adding 20.04g of 1, 12-diaminododecane, 46.48g of hexamethylenediamine and 47.77g of guanidine hydrochloride into a reaction vessel, heating to 80 ℃, gradually heating to 120 ℃ for reaction for 2 hours after all reactants are molten, heating every 30: 30min with a heating gradient, heating to 160 ℃, preserving heat for reaction for 4 hours to obtain a water-soluble polyguanidine polymer with a linear structure, cooling to 100 ℃ after the reaction is finished, and adding 114.29g of deionized water to obtain a polymer aqueous solution;
s2, regulating the pH value of the polymer aqueous solution to 9, slowly dropwise adding 97.15g of epichlorohydrin at 20-25 ℃, heating to 65 ℃ after the dropwise adding is completed, and reacting for 2 hours to obtain the micro-crosslinking reaction type guanidine durable antibacterial finishing agent.
Comparative example 1:
S1, adding 61.01g of hexamethylenediamine and 47.77g of guanidine hydrochloride into a reaction container, heating to 80 ℃, gradually heating to 120 ℃ for reaction for 2 hours after all reactants are molten, heating every 30min to 160 ℃ by taking 10 ℃ as a heating gradient, carrying out heat preservation for reaction for 4 hours to obtain a water-soluble polyguanidine polymer with a linear structure, cooling to 100 ℃ after the reaction is finished, and adding 108.78g of deionized water to obtain a polymer aqueous solution;
s2, regulating the pH value of the polymer aqueous solution to 10, slowly dropwise adding 46.26g of epichlorohydrin at 20-25 ℃, heating to 65 ℃ after the dropwise adding is completed, and reacting for 2 hours to obtain the guanidine antibacterial finishing agent.
Application examples the micro-crosslinking reactive guanidine durable antimicrobial finish prepared in examples 1 to 4, the guanidine antimicrobial finish prepared in comparative example 1, and commercially available guanidine antimicrobial PHMG-PTG were used for the antimicrobial fixation finishing of cellulosic fiber fabrics, protein fiber fabrics, or blends or interweaves of either or both with chemical fibers, and the application examples selected the use of a reddish colored cotton fabric as an example.
An antibacterial fixation finishing aqueous solution is prepared, and the solid content is uniformly converted according to 25 percent as a standard and then is applied. The antibacterial fixation finishing process of the reddish dyed cotton fabric comprises the steps of preparing an antibacterial fixation finishing aqueous solution into working solution with the concentration of 30g/L, and drying at 120-180 ℃ in a one-dipping-one-rolling mode.
The antibacterial performance and the color fixing performance of the reddish dyed cotton fabric after antibacterial color fixing finishing are tested, wherein the antibacterial performance is evaluated according to GB/T20944.3-2008 textile antibacterial performance evaluation part 3, namely, the vibration method and 50 times of washing by a household double-drum washing machine in the standard, and the color fixing performance is evaluated according to GB/T3920-2008 textile color fastness test rubbing color fastness and GB/T3921-2008 textile color fastness to soaping color fastness. The antibacterial performance and fixation performance of the reddish dyed cotton fabric after antibacterial fixation finishing are shown in tables 1 and 2 below, respectively.
Table 1 comparison of antibacterial properties after antibacterial fixation finishing
,
Table 2 comparison of color fixing Properties after antibacterial color fixing finishing
。
As can be seen from tables 1 and 2, the micro-crosslinking reaction type guanidine durable antibacterial finishing agent prepared by the invention is used for antibacterial fixation finishing of cellulose fiber fabrics, the finished fabrics have excellent antibacterial performance, the antibacterial rate is more than or equal to 99%, the antibacterial rate after 50 times of standard washing is more than or equal to 95%, the durability is excellent, and the color fastness performance of dyed fabrics is improved by half or more while antibacterial, so that the micro-crosslinking reaction type guanidine durable antibacterial finishing agent is a composite multifunctional antibacterial fixation finishing agent and has good market application prospect.
In combination with the illustration of fig. 1, the micro-crosslinking reaction type guanidine durable antibacterial finishing agent prepared in example 4 is characterized in that the micro-crosslinking reaction type guanidine durable antibacterial finishing agent can form a longer long-chain structure and has a larger molecular weight through the long-chain structure, the long-chain structure and the larger molecular weight can better realize the color fixing performance, and in addition, the micro-crosslinking reaction type guanidine durable antibacterial finishing agent can be applied to antibacterial and color fixing finishing in a post-finishing process and can be added into spinning solution as an auxiliary agent in a spinning stage, and has a higher decomposition temperature, so that the micro-crosslinking reaction type guanidine durable antibacterial finishing agent cannot be decomposed at a higher temperature in the spinning stage, and further has a better antibacterial effect after raw material spinning.
The specific embodiments described herein are offered by way of example only to illustrate the spirit of the invention. Those skilled in the art may make various modifications or additions to the described embodiments or substitutions thereof without departing from the spirit of the invention or exceeding the scope of the invention as defined in the accompanying claims.
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| CN102388905A (en) * | 2011-10-17 | 2012-03-28 | 华南理工大学 | Quaternary ammonium salt grafted guanidine salt bactericide and preparation method thereof |
| CN108330694A (en) * | 2018-01-19 | 2018-07-27 | 苏州依司特新材料科技有限公司 | A kind of antibacterial for cotton fabric and hydrophilic soft finishing agent and preparation method thereof |
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- 2025-05-16 CN CN202510629413.4A patent/CN120157877A/en active Pending
Patent Citations (4)
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|---|---|---|---|---|
| WO2004052961A1 (en) * | 2002-10-18 | 2004-06-24 | Progetto Idea S.P.A. | Sterilizing polymers and preparation and use thereof |
| CN101250263A (en) * | 2007-11-28 | 2008-08-27 | 广州科仁机电有限公司 | Polyamine and guanidine salt prepolymer, polymer as well as preparation method and uses thereof |
| CN102388905A (en) * | 2011-10-17 | 2012-03-28 | 华南理工大学 | Quaternary ammonium salt grafted guanidine salt bactericide and preparation method thereof |
| CN108330694A (en) * | 2018-01-19 | 2018-07-27 | 苏州依司特新材料科技有限公司 | A kind of antibacterial for cotton fabric and hydrophilic soft finishing agent and preparation method thereof |
Non-Patent Citations (1)
| Title |
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| 叶迎;董超;李翠玉;肖惠宁;何北海;钱丽颖;: "一种新型胍盐抗菌剂的制备及其性能研究", 高分子通报, no. 11, 15 November 2014 (2014-11-15), pages 101 - 108 * |
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