WO2017200220A1 - Microfibre de cellulose modifiée en surface par un copolymère associatif et composition épaississante la comprenant - Google Patents

Microfibre de cellulose modifiée en surface par un copolymère associatif et composition épaississante la comprenant Download PDF

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WO2017200220A1
WO2017200220A1 PCT/KR2017/004425 KR2017004425W WO2017200220A1 WO 2017200220 A1 WO2017200220 A1 WO 2017200220A1 KR 2017004425 W KR2017004425 W KR 2017004425W WO 2017200220 A1 WO2017200220 A1 WO 2017200220A1
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Prior art keywords
cellulose
monomer
hydrophilic
microfiber
microfibers
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PCT/KR2017/004425
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English (en)
Korean (ko)
Inventor
김진웅
이예람
양태승
최상구
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Industry University Cooperation Foundation IUCF HYU
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Industry University Cooperation Foundation IUCF HYU
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Priority to CN201780030848.0A priority Critical patent/CN109153821A/zh
Publication of WO2017200220A1 publication Critical patent/WO2017200220A1/fr
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L1/00—Compositions of cellulose, modified cellulose or cellulose derivatives
    • C08L1/08—Cellulose derivatives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73—Polysaccharides
    • A61K8/731—Cellulose; Quaternized cellulose derivatives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/0241—Containing particulates characterized by their shape and/or structure
    • A61K8/027—Fibers; Fibrils
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
    • C08J7/12—Chemical modification
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/10—General cosmetic use
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/48—Thickener, Thickening system
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2301/00—Characterised by the use of cellulose, modified cellulose or cellulose derivatives
    • C08J2301/08—Cellulose derivatives

Definitions

  • the present invention relates to a cellulose microfiber surface-modified with an associative copolymer copolymerized with a hydrophilic monomer and a hydrophobic monomer, a thickener composition comprising the same, and a method for preparing the same.
  • thickeners are included as additives for controlling workability and rheological properties in systems such as cosmetic compositions.
  • Synthetic polymer thickener is used to enhance the viscosity of the composite fluid by increasing the viscosity of the system, preventing the separation of the water phase and the oil phase.
  • organic compounds synthetic polymers such as acrylic acid polymers and carboxyvinyl polymers are used, and as inorganic compounds, montmorillonite, various clay minerals and silicas are used as thickeners.
  • the use of petroleum-derived PEG-added synthetic surfactants and synthetic polymer thickeners is becoming more stringent, and studies on natural polymers and natural thickeners that can replace them are being actively conducted.
  • Synthetic polymer thickener shows a uniform thickening effect due to the constant molecular weight and twisting of the polymer chain. It maintains a relatively stable aqueous phase even under various external conditions such as temperature changes, salt loading, and pH changes.
  • carbomer is the most widely used, and most synthetic polymer thickeners including carbomer can be used as a thickener by dissolving or dispersing in water.
  • 0.001 to 20 wt% of a thickener is added to the total weight of the cosmetic composition, and may be blended directly with the cosmetic composition or after dilution with water or a solvent to obtain a suitable viscosity.
  • Korean Laid-Open Patent Publication No. 2001-0075666 relates to a mixture of an associative thickener and an aqueous protective coating composition, and discloses a hydrophobically modified cellulose derivative as an associative thickener.
  • the disclosed cellulose derivatives such as hydroxyethyl cellulose, methyl cellulose, carboxymethyl cellulose, ethyl hydroxyethyl cellulose and the like have only a hydrophobic moiety on the surface of the cellulose, and thus do not show a large incremental effect.
  • the present inventors introduced the associative copolymer by applying a polymer grafting technology to the surface of the cellulose to develop a synthesizing cellulose microfiber dispersion by oxidative reaction in order to develop a conventional synthetic thickener and other naturally occurring thickener.
  • a thickener thereof the present invention was completed by confirming a very excellent effect.
  • Patent Document 1 Korean Unexamined Patent Publication No. 2001-0075666
  • Another object of the present invention is to provide a thickener composition comprising the cellulose microfibers.
  • Still another object of the present invention is to provide a cosmetic composition comprising the thickener composition.
  • the present invention provides cellulose microfibers surface-modified with associative copolymers copolymerizing hydrophilic monomers and hydrophobic monomers.
  • the present invention comprises the steps of: 1) grafting the associative copolymer on the surface of the cellulose by living radical copolymerization of a solution containing cellulose, hydrophilic monomers and hydrophobic monomers;
  • the cellulose microfibers according to one embodiment of the present invention are surface-modified with an associative copolymer such that the cellulose microfibers form a gel phase.
  • This three-dimensional microfiber gel phase not only exerts an excellent incremental effect due to strong hydration behavior, but also exhibits differentiated rheological behavior by physical interaction between the microfibers.
  • the cellulose microfibers of the present invention are structurally stable and exhibit chemical resistance, flame resistance, and pH resistance, and provide differentiated usability, skin safety, and cosmetic formulation stability. Therefore, the thickener composition using the cellulose microfibers can be widely applied to the cosmetics market, such as cosmetic compositions, external application composition for the skin, and is expected to be highly utilized in various industries based on the composite fluid.
  • FIG. 1 is a view showing a manufacturing process of the surface-modified cellulose microfibers with an associative copolymer according to an embodiment of the present invention.
  • Figure 2 shows the results of morphology confirmation of cellulose microfibers via TEM: (left) surface unmodified cellulose microfibers, (right) cellulose microfibers with poly (MPC-co-SMA) introduced.
  • FIG. 3 shows the results of the synthesis efficiency analysis of 2-methacryloyloxyethyl phosphorylcholine (MPC) and stearyl methacrylate (SMA) using 1 H-NMR.
  • MPC 2-methacryloyloxyethyl phosphorylcholine
  • SMA stearyl methacrylate
  • FIG. 6 shows the results of rheological properties of cellulose microfiber dispersions surface-modified with associative copolymers: (A) elastic modulus, (B) viscous modulus, (C) shear stress, (D) yield by SMA content Stress.
  • FIG. 7 shows the results of flame resistance and pH resistance measurement of cellulose microfiber dispersions surface-modified with associative copolymers:
  • A Unmodified microfiber dispersions (Neat CNFs) and surface modified microfiber dispersions (ACNFs). After the addition of 0, 1 or 1.5 M NaCl, the viscosity was measured to confirm the flame resistance.
  • B Surface modified microfiber dispersions (Neat CNFs) and surface modified microfiber dispersions (ACNFs) were prepared at pH 2, 7 or 11 After adjusting the viscosity, the viscosity was measured to confirm the pH resistance.
  • One embodiment of the present invention provides a cellulose microfiber surface-modified with an associative copolymer copolymerized with a hydrophilic monomer and a hydrophobic monomer.
  • sociative means that two or more molecules of the same species have a property to combine (associate) with a loose regularity by combining by two or more intermolecular forces.
  • copolymerization refers to a reaction of synthesizing a copolymer by mixing and polymerizing two or more monomers.
  • a random copolymer is generally formed in which A and B are mixed irregularly, but a block copolymer having a structure in which A and B are regularly arranged according to the polymerization method ( A block copolymer or a grafted copolymer having a branch of B in a polymer of A may be generated.
  • the "copolymer” may be a random copolymer, a block copolymer or a graft copolymer, for example, but may be a random copolymer, but is not necessarily limited thereto.
  • hydrophilic monomer refers to a monomer containing a hydrophilic functional group, and specifically, may be a zwitterionic monomer, anionic monomer, cationic monomer or nonionic monomer.
  • the hydrophilic monomer may be any one of hydrophilic ethylenically unsaturated monomer, 2-methacryloyloxyethyl phosphorylcholine and betaine, or a mixture of two or more thereof. It is not limited.
  • the hydrophilic ethylenically unsaturated monomer may include acrylamide, methacrylamide, N-alkylacrylamide, vinyl sulfonic acid, styrene sulfonic acid, and the like, but is not limited thereto.
  • the "2-methacryloyloxyethyl phosphorylcholine (MPC)" is a biomimetic monomer having an amphoteric ion (zwitterion), and has excellent biocompatibility. Therefore, when the MPC is used as the hydrophilic monomer, it has excellent biocompatibility and can be safely used on the human body such as skin.
  • betaine refers to a molecule having an anion of quaternary ammonium and an acid (especially carboxylic acid) as a cation in one molecule, and has excellent biocompatibility.
  • the hydrophobic monomer may be C6 ⁇ C22 alkyl ester of acrylate or C6 ⁇ C22 alkyl ester of methacrylate, for example, C18 alkyl ester of methacrylate, that is, stearyl methacrylate. This is not restrictive.
  • the associative copolymer may have a content ratio of hydrophilic monomer and hydrophobic monomer of 1: 0.0001 to 1, specifically 1: 0.0001 to 0.1, more specifically 1: 0.0001 to 0.01, and more specifically 1: 0.001 to 0.01, more specifically 1: 0.005 to 0.01, and more specifically 1: 0.007 to 0.008, for example 1: 0.0075, but is not necessarily limited thereto. no.
  • the "surface modification” may mean that the associative copolymer is bonded to the surface of the cellulose microfibers, for example, may mean that the associative copolymer is grafted to the cellulose microfibers.
  • the cellulose microfiber may have a length of 10 to 5000 nm, but is not limited thereto.
  • the cellulose microfiber may have a thickness of 0.001 to 1000 nm, but is not limited thereto.
  • Another embodiment of the present invention provides a thickener composition comprising the cellulose microfibers.
  • thickener refers to a substance that increases the viscosity of the solution.
  • the thickener composition may be a dispersion in which cellulose microfibers are dispersed in a solvent, but is not necessarily limited thereto, and the thickener composition may be prepared using a suitable method known in the art.
  • the thickener composition may have a viscosity of 1 to 1000000 Pa ⁇ s, and specifically, may have a viscosity of 1 to 100,000 Pa ⁇ s, but is not limited thereto.
  • the associative copolymer present on the surface of the cellulose microfibers may form a cellulose gel network by hydrophobic interaction with each other in the aqueous phase.
  • This cellulose microfiber gel phase exhibits performance similar to that of conventional thickeners, as well as shear thinning under relatively low shear forces. When the shear force is removed, the initial viscosity is reversibly recovered, thereby giving a differentiated feeling.
  • the thickener composition according to the embodiment is composed of a network of nm unit can be contained and permeable to the effective ingredients on the skin, but can protect the skin by preventing the transmission of harmful substances such as bacteria and dust outside the skin.
  • Another embodiment of the present invention provides a cosmetic composition comprising the thickener composition.
  • the thickener composition may include 0.001 to 50 parts by weight based on 100 parts by weight of the cosmetic composition, but is not necessarily limited thereto, and an appropriate amount may be selected according to the formulation, use, etc. of the cosmetic composition.
  • the cosmetic composition may have a moisturizing, atopic improvement effect by including the thickener composition.
  • the cosmetic composition according to the above embodiment is a fatty substance, an organic solvent, a dissolving agent, a gelling agent, a softening agent, an antioxidant, a suspending agent, a stabilizer, a foaming agent, a fragrance, a surfactant, water, an ionic or nonionic emulsifier.
  • Cosmetics such as fillers, metal ion sequestrants, chelating agents, preservatives, vitamins, blockers, wetting agents, essential oils, dyes, pigments, hydrophilic or lipophilic actives, lipid vesicles or any other ingredients commonly used in cosmetics or It may contain adjuvants commonly used in the field of dermatology. Such adjuvants are introduced in amounts generally used in the cosmetic or dermatological arts.
  • the appearance of the cosmetic composition according to the above embodiment contains a cosmetically or dermatologically acceptable medium or base.
  • a cosmetically or dermatologically acceptable medium or base for example, emulsions, suspensions, microemulsions, microcapsules, microgranules or ionic (liposomes) obtained by dispersing the oil phase in solutions, gels, solids, pasty anhydrous products, aqueous phases, and It may be provided in the form of a nonionic vesicle dispersant and these compositions may be prepared according to conventional methods in the art.
  • Cosmetics according to an embodiment of the present invention skin lotion, skin softener, skin toner, astringent, lotion, milk lotion, moisturizing lotion, nutrition lotion, massage cream, nutrition cream, moisturizing cream, hand cream, foundation, essence, nutrition essence , Pack, soap, cleansing foam, cleansing lotion, cleansing cream, body lotion, body cleanser, face wash, treatment, essence, beauty pack, ointment, gel, linen, liquid, patch and spray It is a formulation, but is not limited to a specific formulation, and may have a formulation of a conventional cosmetic composition.
  • Another embodiment of the present invention provides a method for producing cellulose microfibers surface-modified with an associative copolymer, the method comprising
  • the "cellulose” is a very abundant natural resource, can be supplied in large quantities, and the price is excellent.
  • the cellulose molecule is structurally stable and can exhibit chemical resistance, flame resistance, and pH resistance.
  • the cellulose of step 1) may be obtained from wood, Korean paper, paper, cotton, hemp, plants, marine plants, etc., but is not necessarily limited thereto, and may be prepared using a conventional method for obtaining cellulose.
  • the cellulose of step 1) may be cellulose having a start site of a living radical polymerization reaction introduced on a surface thereof.
  • the cellulose of step 1) can be prepared by a method comprising the following steps:
  • the trichloroacetyl group introduced in step b) may be an initiation site of living radical polymerization.
  • the cellulose of step 1) may be included in an amount of 1 to 15% by weight, specifically, 1 to 10% by weight, for example, 3 to 5% by weight, based on the total weight of the solution, but is not limited thereto. Do not.
  • the hydrophilic monomer of step 1) may be a zwitterionic monomer, an anionic monomer, a cationic monomer or a nonionic monomer.
  • the hydrophilic monomer more specifically, the hydrophilic monomer is any one or a hydrophilic ethylenically unsaturated monomer, 2-methacryloyloxyethyl phosphorylcholine (beta) and betaine (betaine) thereof It may be a mixture of two or more, but is not limited thereto.
  • the hydrophilic ethylenically unsaturated monomer may include acrylamide, methacrylamide, N-alkylacrylamide, vinyl sulfonic acid, styrene sulfonic acid, and the like, but is not limited thereto.
  • the hydrophobic monomer of step 1) may be a cellulose microfiber which is a C6 to C22 alkyl ester of acrylate or a C6 to C22 alkyl ester of methacrylate, for example a C18 alkyl ester of methacrylate, namely stearyl methacryl Stearyl methacrylate, but is not limited thereto.
  • the solution of step 1) may further include a catalyst that can be used for living radical polymerization, and may further include, for example, molybdenum carbonyl (Mo (CO) 6 ), but is not limited thereto.
  • a catalyst that can be used for living radical polymerization
  • Mo (CO) 6 molybdenum carbonyl
  • the associative copolymer of step 1) may have a content ratio of the hydrophilic monomer and the hydrophobic monomer of 1: 0.0001 to 1, specifically 1: 0.0001 to 0.1, more specifically 1: 0.0001 to 0.01, It may be more specifically 1: 0.001 ⁇ 0.01, even more specifically 1: 0.005 ⁇ 0.01, even more specifically 1: 0.007 ⁇ 0.008, for example 1: 0.0075, but not necessarily It is not limited to this.
  • Cellulose is composed of fiber bundles, if not treated otherwise.
  • step 2) is carried out to convert the cellulose fiber bundles into microfibers having a thickness of several nanometers and a long axis of several microns, a clear gel phase is formed in the aqueous phase.
  • a clear gel phase is formed in the aqueous phase.
  • the cellulose microfibers thus prepared exhibit an excellent incremental effect due to strong hydration behavior and may exhibit differentiated rheological behavior by physical interactions between the fibers.
  • Cellulose with various fiber lengths and thicknesses was dispersed by fixation in toluene at 3 wt%. Then, to introduce an amine group, 150% of 3-aminopropyltriethoxy silane relative to the weight of cellulose was added and reacted with the hydroxyl group (-OH) on the surface of cellulose for 8 hours at 110 ° C. The cellulose into which the amine group (-NH 2 ) was introduced was washed and recovered through repeated centrifugation.
  • a condensation reaction of an amine group and trichloroacetyl isocyanate introduced on the surface of the cellulose particles was performed.
  • the cellulose powder containing the amine group prepared in Example 1-1 was redispersed by irradiating toluene with ultrasonic waves at 35 ° C. for 10 minutes. At this time, the concentration of cellulose was fixed at 3 wt%.
  • Trichloroacetyl isocyanate (50% of the weight of dispersed cellulose) is stirred with tributyltin dilaurate catalyst at 8O < 0 > C in an argon atmosphere for 8 hours to give trichloroacetyl to the surface
  • transduced) group was synthesize
  • Cellulose powder having a polymerization initiator on the surface prepared in Example 1-2 was redispersed by irradiating ethanol at 35 ° C. for 10 minutes with ultrasonic waves. At this time, the concentration of cellulose was fixed at 3 wt%. Subsequently, 2-methacryloyloxyethyl phosphorylcholine (MPC), a biomimetic monomer, and stearyl methacrylate (SMA) having a C18 hydrophobic chain were added to the dispersion. Molybdenum carbonyl (Mo (CO) 6 ) was used as a catalyst and 0.05 wt% of the total weight was added.
  • MPC 2-methacryloyloxyethyl phosphorylcholine
  • SMA stearyl methacrylate
  • Molybdenum carbonyl (Mo (CO) 6 ) was used as a catalyst and 0.05 wt% of the total weight was added.
  • polymer polymerization living radical polymerization
  • polymer polymerization was carried out at 70 ° C. for 12 hours to finally synthesize zwitterionic polymer and cellulose in which hydrophobic chains were introduced to the surface. It was.
  • MPC and SMA are randomly polymerized and introduced into the cellulose surface, MPC and SMA are randomly arranged in the main chain after synthesis.
  • Cellulose polymerized on the surface prepared in Example 1-3 was redispersed in water through stirring at room temperature. At this time, the concentration of cellulose was fixed at 1 wt%. 10-30% NaBr by weight of the dispersed cellulose was added to the dispersion with a TEMPO (2,2,6,6-tetramethylpiperydine-1-oxylradical) catalyst and stirred for 10 minutes at room temperature. Subsequently, 1-15 mmol of NaClO was added, the pH of the reaction solution was titrated to 10 using 0.5 M NaOH, and stirred at 600 rpm for 4 hours at room temperature. Through this oxidation reaction, the remaining hydroxyl groups on the surface of cellulose were oxidized to carboxylic acid via aldehyde, and the cellulose fiber bundles were unwound in microfibrils to obtain cellulose microfibers.
  • TEMPO 2,2,6,6-tetramethylpiperydine-1-oxylradical
  • cellulose was dispersed in water to prepare a cellulose microfiber dispersion having no surface modification.
  • Morphology of fibers chemically synthesized with poly (MPC-co-SMA) associative polymer on the surface of cellulose microfibers was confirmed by transmission electron microscopy (TEM) analysis (FIG. 2).
  • Example 2 the conversion rate of the monomer present in the solvent during the surface polymerization was analyzed. As a result, the synthesis efficiency of surface-modified cellulose microfibers using MPC and SMA was 70% (FIG. 3).
  • the weight ratio of cellulose microfibers was 4 wt%, and all proceeded the same except for the variable values for each experiment.
  • Preparation of cellulose microfibers surface-modified with an associative copolymer was carried out in the same manner as in Example 1 except for varying the ratio of MPC and SMA in the steps of Examples 1-3.
  • ⁇ SMA means the relative content ratio of SMA to MPC.
  • Viscosity was measured by converting the shear stress according to the shear rate into viscosity using a rheometer (model name: DHR1) of TA. The experimental results for this are summarized in FIG. 5.
  • the cellulose microfiber weight ratio was 4 wt%, and all proceeded the same except for the variable values for each experiment.
  • Surface unmodified cellulose microfibers (Neat CNFs) prepared according to Comparative Example 1 were used as controls.
  • the elastic modulus (storage modulus) was measured by converting the shear stress according to the strain (%) to the elastic modulus.
  • the viscous modulus (loss modulus) was measured by converting the shear stress according to the strain (%) into viscous modulus. Shear stress was measured according to shear rate and shear strain.
  • Yield stress was measured using the method of converting elastic modulus and viscous modulus.
  • the measured elastic modulus is shown in FIG. 6A, the viscous modulus in FIG. 6B, the shear stress in FIG. 6C, and the yield stress in FIG. 6D.
  • the cellulose microfibers of the present invention exhibited excellent flame resistance and pH resistance (FIG. 7).
  • the cellulose microfiber gel phase associated by hydrophobic interaction can be interpreted as being able to maintain its own gel phase without being affected by the change in ion concentration.
  • the thickener composition using the cellulose microfibers according to the present invention may be widely applied to the cosmetic market such as a cosmetic composition and a topical skin composition, and is expected to be highly applicable to various industries based on the complex fluid.

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  • Chemical & Material Sciences (AREA)
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Abstract

La présente invention concerne une microfibre de cellulose modifiée en surface par un copolymère associatif présentant un monomère hydrophile et un monomère hydrophobe copolymérisés, un procédé pour sa production et une composition épaississante la comprenant. La microfibre de cellulose modifiée en surface par un copolymère associatif, selon la présente invention, présente d'excellentes capacités d'épaississement grâce à l'utilisation mixte de groupes hydrophobes et hydrophiles, et présente un effet épaississant stable, indépendamment de la salinité élevée et d'un changement de pH.
PCT/KR2017/004425 2016-05-18 2017-04-26 Microfibre de cellulose modifiée en surface par un copolymère associatif et composition épaississante la comprenant Ceased WO2017200220A1 (fr)

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KR1020160060763A KR101818105B1 (ko) 2016-05-18 2016-05-18 회합성 공중합체로 표면 개질된 셀룰로오즈 미세섬유 및 이를 포함하는 점증제 조성물
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CN113563519A (zh) * 2021-07-23 2021-10-29 长江大学 一种接枝乳液稠化剂及其制备方法
CN113563519B (zh) * 2021-07-23 2024-02-02 长江大学 一种接枝乳液稠化剂及其制备方法

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