Antibacterial spinning oil

Abstract

The invention relates to a preparation method of antibacterial spinning oil containing water-soluble oregano essential oil. The water-soluble oregano essential oil is obtained by catalyzing a ring-opening polymerization reaction of hydroxyl in oregano essential oil and ethylene oxide through boron trifluoride diethyl etherate. The antibacterial spinning oil is mainly used for preparing antibacterial polyester staple fibers, antibacterial PE / PP composite staple fibers and antibacterial PE / PET composite staple fibers.

Description

Technical Field

[0001] The invention relates to a preparation method of an antibacterial spinning oil and application thereof. Background Art

[0002] Antimicrobial spinning oils are primarily used to produce chemical staple fibers for the sanitary products industry, such as polyester staple fibers, PE / PP composite staple fibers, and PE / PET composite staple fibers. These staple fibers are primarily used to produce various non-woven fabrics, including spunlace and thermal bond, for use in wet wipes, sanitary napkins, diapers, and nursing pads.

[0003] The antimicrobial agents used in these antimicrobial spinning oils are typically water-soluble quaternary ammonium salts, such as alkyl dimethyl ammonium bromide and cetylpyridinium chloride. While these fungicides offer excellent antimicrobial efficacy, their cationic nature poses a potential safety risk to consumers with sensitive skin, such as infants, causing skin irritation and allergies. Furthermore, cationic compounds are prone to corroding metal components in spinning equipment (such as guide rollers, stretching rollers, crimping rollers, and cutting knives).

[0004] In view of the above-mentioned defects of quaternary ammonium salt fungicides, the application research of non-cationic natural plant essential oils with antibacterial function has attracted much attention in recent years.

[0005] Oregano oil is a light yellow, natural essential oil extracted through steam distillation from the stems and leaves of oregano (a perennial herb of the genus Origanum in the family Lamiaceae). It has a refreshing, herbal aroma. Oregano essential oil has a wide range of medicinal uses and a long history of use. It is widely used in traditional medicine and health maintenance. Its powerful antiseptic properties have earned it the reputation of a "natural antibiotic." After dilution with an organic solvent, it can be used directly to treat various bacterial infections, including onychomycosis.

[0006] Oregano essential oil is insoluble in water, significantly limiting its antimicrobial applications because fungi primarily reside in the aqueous phase. While surfactant solubilization, a well-known technique for making oregano essential oil soluble in water, works by encapsulating the oil in the surfactant in the form of micelles, preventing the oil from coming into direct contact with the aqueous phase and, therefore, preventing it from exerting its antimicrobial effects. Summary of the Invention

[0007] To address the problems in the prior art, the present invention first provides a method for preparing ethylene oxide-chemically modified oregano essential oil and the resulting water-soluble oregano essential oil. The present invention also provides a method for preparing an antibacterial spinning oil containing the water-soluble oregano essential oil and its application process.

[0008] According to public data, the composition of oregano essential oil is complex and diverse. Its main chemical components are carvacrol and thymol, of which the content of carvacrol is about 60% and the content of thymol is about 8%. In addition to phenolic compounds, oregano essential oil also contains a certain proportion of alcohol compounds, such as linalool, linalool, and menthol. The above phenolic compounds and alcohol compounds contain one or more hydroxyl groups in their structures, so they have high chemical modifiability. The hydroxyl groups and ethylene oxide in the compounds undergo ring-opening polymerization in the presence of a catalyst to form ethylene glycol chains. Ethylene glycol chains can easily form hydrogen bonds in water, and therefore have good water solubility.

[0009] The present invention uses oregano essential oil and ethylene oxide as main raw materials. Ethylene oxide-modified water-soluble oregano essential oil is synthesized through a ring-opening polymerization reaction between hydroxyl groups in oregano essential oil molecules and ethylene oxide in the presence of a catalyst, boron trifluoride etherate. The oregano essential oil is a mixture of oregano essential oil polyoxyethylene ethers, all of which are produced by the same reaction.

[0010] The preparation method of the water-soluble oregano essential oil of the present invention: At room temperature, add oregano essential oil and boron trifluoride etherate in a 50:1 mass ratio to a reactor. Seal the reactor and heat to 60°C while stirring at 100 rpm. Evacuate the reactor and purge with nitrogen five times to maintain an inert atmosphere. Add ethylene oxide in an amount equal to three times the mass of the oregano essential oil. After the addition of ethylene oxide, maintain the original temperature and stirring rate until the reactor pressure drops to near zero and remains essentially constant. Cool the reactor with condensed water until the temperature drops to room temperature before discharging the product.

[0011] The final product is the water-soluble oregano essential oil of the present invention, which is a light yellow transparent viscous liquid with a viscosity of 35 Pa·s (25° C.) and a pH value of 6.8. Its maximum solubility in water at 25° C. is 8 g / 100 ml.

[0012] The antibacterial experiment of the water-soluble oregano essential oil of the present invention is as follows: Water-soluble oregano essential oil was prepared with sterile distilled water at a series of concentration gradients (mass percentage: 0.04%, 0.06%, 0.08%, 0.10%, and 0.12%). Its 20-minute antibacterial properties against Staphylococcus aureus (a representative species of pyogenic cocci), Escherichia coli (a representative species of enteric infections), and Candida albicans (a representative fungal species) were tested. The results are shown in the table.

[0013] Antibacterial performance test results of water-soluble oregano essential oil solutions at different concentrations The data in the table show that when the mass percentage of the essential oil was 0.10%, the inhibition rate against all three representative bacterial species was >90%, demonstrating a strong antibacterial effect. When the mass percentage of the antibacterial agent was 0.12%, the inhibition rate against all three representative bacterial species reached 100%. At the same dose, the essential oil exhibited varying antibacterial effects against the three bacterial species, with the greatest effect against Staphylococcus aureus, followed by Escherichia coli, and a relatively weaker effect against Candida albicans.

[0014] The antibacterial mechanism of the water-soluble oregano essential oil of the present invention is mainly to inhibit the reaction of certain enzymes in fungi or microorganisms or to inhibit the synthesis of enzymes in biological cells.

[0015] The preparation method of the water-soluble oregano essential oil of the invention has a simple synthesis route, low reaction temperature, short reaction time and low energy consumption during industrial production.

[0016] The water-soluble oregano essential oil of the present invention has the advantages of having good water solubility through simple chemical modification and maintaining the good antibacterial properties of the oregano essential oil itself, thereby overcoming the disadvantage that the oregano essential oil cannot be used for aqueous antibacterial purposes.

[0017] Preparation method of the antibacterial spinning oil containing the water-soluble oregano essential oil of the present invention: At room temperature, the following components were added to a stirred tank in order by mass: 50% of potassium phosphate of dodecyl fatty alcohol ether (3) (solid content 40%), 4.9% of octadecyl fatty alcohol polyoxyethylene ether (10), 15% of water-soluble oregano essential oil, and 0.1% of an organosilicon defoamer. Deionized water was added to 100%, and stirring was started at a speed of 30 rpm. Stirring was continued for 30 minutes, and the mixture was discharged to obtain an antibacterial spinning oil containing the water-soluble oregano essential oil of the present invention.

[0018] In the above-mentioned antibacterial spinning oil formulation, potassium salt of lauryl fatty alcohol ether (3) phosphate ester is an antistatic agent, octadecyl fatty alcohol polyoxyethylene ether (10) is a softening agent and penetrant, and water-soluble oregano essential oil is an antibacterial agent and has both softening and penetrating functions.

[0019] The antibacterial spinning oil of the present invention is a transparent, light yellow viscous liquid with a solid content of 40±1%, a viscosity of 30±2 Pa·s (25°C), a pH value of 5.5±0.2, a very slight characteristic odor, and is easily soluble in water. A 0.1% aqueous solution thereof has a 20-minute antibacterial rate of >99% against Staphylococcus aureus, Escherichia coli, and Candida albicans, is non-irritating to the skin, and will not cause skin allergic reactions.

[0020] The application fields of the antibacterial spinning oil of the present invention include the preparation of antibacterial polyester staple fibers, antibacterial PE / PP composite staple fibers, and antibacterial PE / PET composite staple fibers.

[0021] The application process of the antibacterial spinning oil of the present invention can be carried out according to the conventional application process of known spinning oils, including the addition amount of spinning oil in pre-spinning and post-spinning, spinning solution temperature, oil application rate, etc.

[0022] Experiments have shown that the chemical staple fibers prepared using the antibacterial spinning oil of the present invention have good dispersibility, combing properties, permeability, and softness. The 20-minute antibacterial rates of the chemical staple fibers against Staphylococcus aureus, Escherichia coli, and Candida albicans are all greater than 90%, and the fibers are non-irritating to the skin and will not cause skin allergies. DETAILED DESCRIPTION

[0023] The present invention will be further described by way of examples, the purpose of which is only to provide a better understanding of the content of the present invention. Therefore, the examples given do not limit the scope of protection of the present invention. Example

[0024] Step 1: Preparation of water-soluble oregano essential oil: 1. Check the vacuum degree of the reactor to ensure that there is no leakage in the pipeline and the nitrogen is flowing smoothly.

[0025] 2. At room temperature, add 500 g of commercially available oregano essential oil and 10 g of boron trifluoride etherate as a catalyst into a reaction kettle, seal it, heat it to 60°C, and stir it (100 r / min).

[0026] 3. Evacuate the reactor and pass nitrogen gas, repeat 5 times to keep the reactor in an inert gas environment.

[0027] 4. Add 1500 g of ethylene oxide and continue the reaction at the original temperature and stirring speed. The reaction is completed when the pressure in the reactor drops to a value close to zero and remains substantially unchanged.

[0028] 5. Connect condensing water for cooling, wait until the temperature drops to room temperature, and then discharge the material. The light yellow transparent viscous liquid obtained is water-soluble oregano essential oil.

[0029] Step 2: Preparation of antibacterial spinning oil: At room temperature, the following components were added to the stirred tank in order by mass: 50% of potassium phosphate of dodecyl fatty alcohol ether (3) (solid content 40%), 4.9% of octadecyl fatty alcohol polyoxyethylene ether (10), 15% of water-soluble oregano essential oil, and 0.1% of silicone defoamer. Deionized water was added to 100%, and stirring was started at a speed of 30 rpm. Stirring was continued for 30 minutes, and the material was discharged.

Claims

1. Preparation of Water-Soluble Oregano Essential Oil: At room temperature, add oregano essential oil and boron trifluoride etherate in a 50:1 mass ratio to a reactor. Seal the reactor and heat to 60°C while stirring at 100 rpm. Evacuate the reactor and purge with nitrogen five times to maintain an inert atmosphere. Add ethylene oxide in an amount equal to three times the mass of the oregano essential oil. After the addition of ethylene oxide, maintain the original temperature and stirring rate until the reactor pressure drops to near zero and remains essentially constant. Cool the reactor with condensing water until the temperature drops to room temperature before discharging the product.

2. A method for preparing an antibacterial spinning oil containing the water-soluble oregano essential oil according to claim 1: at room temperature, add the following components in order by mass into a stirred tank: 50% of lauryl fatty alcohol ether (3) potassium phosphate (solid content 40%), 4.9% of octadecyl fatty alcohol polyoxyethylene ether (10), 15% of water-soluble oregano essential oil, and 0.1% of an organosilicon defoamer; add deionized water to 100%, start stirring, set the stirring speed at 30 rpm, continue stirring for 30 minutes, and then discharge the material.

3. Application fields of the antibacterial spinning oil according to claims 1-2: preparation of antibacterial polyester staple fibers, antibacterial PE / PP composite staple fibers, and antibacterial PE / PET composite staple fibers.

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