EP4253651A1 - Méthode de revêtement d'une matière cellulosique - Google Patents

Méthode de revêtement d'une matière cellulosique Download PDF

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Publication number
EP4253651A1
EP4253651A1 EP23020166.7A EP23020166A EP4253651A1 EP 4253651 A1 EP4253651 A1 EP 4253651A1 EP 23020166 A EP23020166 A EP 23020166A EP 4253651 A1 EP4253651 A1 EP 4253651A1
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EP
European Patent Office
Prior art keywords
cyclodextrin
resulting
starch
coating
solid
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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.)
Pending
Application number
EP23020166.7A
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German (de)
English (en)
Inventor
Ana Filipa MARTINS LOURENÇO
Artur José MONTEIRO VALENTE
Roberto Juan AGUADO GARCIA
Ana Cláudia Dos Santos Ferreira
Dina Maria BAIRRADA MURTINHO
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Raiz Instituto De Investigacao Da Floresta E Papel
Universidade de Coimbra
Original Assignee
Raiz Instituto De Investigacao Da Floresta E Papel
Universidade de Coimbra
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Publication of EP4253651A1 publication Critical patent/EP4253651A1/fr
Pending legal-status Critical Current

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Classifications

    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H19/00—Coated paper; Coating material
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H19/00—Coated paper; Coating material
    • D21H19/36—Coatings with pigments
    • D21H19/44—Coatings with pigments characterised by the other ingredients, e.g. the binder or dispersing agent
    • D21H19/54—Starch
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
    • D21H17/20—Macromolecular organic compounds
    • D21H17/21—Macromolecular organic compounds of natural origin; Derivatives thereof
    • D21H17/24—Polysaccharides
    • D21H17/28—Starch
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H19/00—Coated paper; Coating material
    • D21H19/10—Coatings without pigments
    • D21H19/14—Coatings without pigments applied in a form other than the aqueous solution defined in group D21H19/12
    • D21H19/20—Coatings without pigments applied in a form other than the aqueous solution defined in group D21H19/12 comprising macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H21/00—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties
    • D21H21/14—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties characterised by function or properties in or on the paper
    • D21H21/36—Biocidal agents, e.g. fungicidal, bactericidal, insecticidal agents
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H27/00—Special paper not otherwise provided for, e.g. made by multi-step processes
    • D21H27/10—Packing paper

Definitions

  • the present invention relates to the area of consumer goods industries and specifically refers to a method for coating cellulosic material with essential oils for their application as antimicrobial and antioxidant materials.
  • Active compounds in essential oils range from small molecules, such as monoterpenes and low molecular weight (MW) aldehydes [7], to non-volatile entities, including triterpenes, sterols, and polyphenols [8].
  • eucalyptus essential oils are characterized by having terpenes and terpenoids in abundance. Of these, high MW compounds prevail in wood [9], while leaves mainly host low MW ( ⁇ 180 g/mol) compounds [7].
  • a major disadvantage of adding monoterpene compounds to paper by simple addition, either during sheet formation or as a coating component, is their tendency to evaporate along with water.
  • the patent application EP0690170A1 [13] describes a process for coating paper, in which the aqueous coating consists of a starch modified through its reaction with an enzyme from the group of cyclodextrin glycosyl transferases, and which aims to make the surface of a paper sufficiently smooth and resistant.
  • Patent application CN111691224A [14] also describes this type of enzymes for the modification of starch and their application in paper production to increase the retention of starch and thus, consequently, the strength of the paper incorporating it.
  • the present invention relates to a method for coating cellulosic material comprising the following steps:
  • step a) comprises the following steps:
  • step a) comprises the following steps:
  • the polycarboxylic acid is a 1,2,3,4-Butanetetracarboxylic acid.
  • the cyclodextrin is selected from the group consisting of alpha-cyclodextrin, beta-cyclodextrin, gamma-cyclodextrin, hydroxypropyl-alpha-cyclodextrin, hydroxypropyl-beta-cyclodextrin, hydroxypropyl-gamma-cyclodextrin, methyl-alpha-cyclodextrin, methyl-beta-cyclodextrin, methyl-gamma-cyclodextrin, acetyl-alpha-cyclodextrin, acetyl-beta-cyclodextrin, acetyl-gamma-cyclodextrin, succinyl-alpha-cyclodextrin, succinyl-beta-cyclodextrin, succinyl-gamma-cyclodextrin and 7-beta-cyclodextrin
  • step a) comprises the following steps:
  • the polycarboxylic acid is 1,2,3,4- acid tetracarboxylic butane.
  • the coating formulation of step d) has 0,01 to 0,50 mmol of a cyclodextrin per gram of starch.
  • the cellulosic material is a paper product.
  • the cellulosic material is a textile material.
  • the essential oil is selected from the group consisting of essential oils of wood, leaves, and fruits of plants.
  • the coating medium consists of a roller coating.
  • the mean for coating a surface of a cellulosic material consists of dipping the cellulosic material in an aqueous dispersion of the coating formulation.
  • the approach of the present invention involves the use of cyclodextrins to prolong the ability of cellulosic material to emit volatile active compounds in time.
  • a cyclodextrin is any cyclic oligosaccharide, composed of anhydroglucose units joined by ⁇ -1,4-type bonds, and with their functional groups oriented such that it has a hydrophobic cavity and a hydrophilic exterior.
  • alpha-cyclodextrin with 6 anhydroglucose units
  • beta-cyclodextrin with 7 units
  • the gamma-cyclodextrin with 8 units
  • the respective cyclodextrins functionalized with the hydroxypropyl group, that is, hydroxypropyl-alpha-cyclodextrin, hydroxypropyl-beta-cyclodextrin, hydroxypropyl-gamma-cyclodextrin, functionalized with the methyl group, that is, methyl-beta-cyclodextrin, methyl-gamma-cyclodextrin, functionalized with the acetyl group, i.e.
  • acetyl-alpha-cyclodextrin acetyl-beta-cyclodextrin, acetyl-gamma-cyclodextrin, and functionalized with the succinyl group, i.e. succinyl-alpha-cyclodextrin, succinyl-beta-cyclodextrin, succinyl-gamma-cyclodextrin.
  • native cyclodextrin refers to a cyclodextrin that has not been subjected to chemical modification.
  • chemical modification refers to the process by which the molecular structure of a starch is modified through a reaction, incorporating cyclodextrins by covalent bonds.
  • Covalent bond is a region of high electron density between two atomic nuclei, wherein the electron clouds of the interacting atoms overlap.
  • the covalent bonds generated involve, at least, one oxygen atom of a polycarboxylic acid and one carbon atom of a carbohydrate, namely cyclodextrin and/or starch.
  • polycarboxylic acid is an organic compound with more than one carboxyl group, -COOH, such as citric acid, 1,2,3,4-butanetetracarboxylic acid, maleic acid or fumaric acid.
  • starch consists of a polysaccharide of glucose units having alpha-1,4 and alpha-1,6 linkages.
  • Modified starch in this invention refers to any starch derivative which contains, by means of covalent linkages, alpha-, beta- or gamma-cyclodextrin structures, such that at least one anhydroglucose unit of the starch is linked to a cross-linking agent which, in turn, is linked to an anhydroglucose unit of the cyclodextrin.
  • Native starch in turn, refers to starch that has not undergone any chemical modification.
  • volatile active compound means any organic compound having, at 25 °C, a vapor pressure equal to or greater than 0.01 kPa, and which is commercially appreciated for having antioxidant, antimicrobial, anti-inflammatory, cytotoxic, or other types of activity of health interest, for the preservation of food, or for the preservation of the material itself.
  • macroscopic homogeneity refers to the observation of a single phase with the naked eye, without using any diffractometers, microscopes, spectrophotometers, or other instruments to differentiate between a continuous phase and a dispersed phase, either because dissolution is complete or because the dispersed particles are not appreciable to the naked eye.
  • cellulosic material includes paper material and textile material.
  • paper material relates to, for example and not limited to, tissue paper, packaging paper, printing and writing paper or any paper that may have a starch coating.
  • textile material includes textile-based materials that may include a starch treatment, such as, for example and not limited to, cotton or rayon.
  • essential oils are liquids, consisting of natural active or aromatic compounds, which are extracted from plant material such as, but not limited to, woods, leaves, and fruits.
  • the essential oils considered in the present invention have at least one volatile active compound.
  • Means for coating a surface of a cellulosic material in the context of the present invention, relates to means for applying and evenly distributing coatings to a substrate, whether by bonding press, curtain coating, roller and/or scraper coating, printing, or dipping.
  • Roller coating considers the application of a coating to a substrate by means of one or more rollers of, for example, but not limited to, rubber or steel.
  • retarding the evaporation of essential oils on the surface of cellulosic materials means preserving, for 7 days or more, volatile active compounds which, without modifications to conventional coating processes, would completely evaporate together with water during drying or during the first 7 days.
  • moisture content refers to the amount of water in a solid material, which can be determined gravimetrically, either by means of a thermobalance or by drying in an oven until constant weighting.
  • the present invention thus relates to a method for coating a cellulosic material comprising the steps of chemically modifying a starch with cyclodextrins, obtaining a modified starch, followed by the step of redispersing this modified starch in water and using the aqueous dispersion in any of the steps of coating a cellulosic material.
  • the method allows protection of volatile active compounds that would otherwise evaporate together with water during drying and by exposure to air of the final product.
  • the described method allows the retardation of the evaporation of essential oils on the surface of cellulosic materials.
  • the modified starch was synthesized by cross-linking, via ester linkages, in one or two steps.
  • a starch was mixed with beta-cyclodextrin, 1,2,3,4-butanetetracarboxylic acid and in contact with the sodium hyposulfite catalyst in an aqueous medium at 25-70 °C. After observation of macroscopic homogeneity, most of the water was evaporated until the mixture showed a moisture content ⁇ 10%, either by being dried at room temperature for more than 18 h or by being heated. The solid was then placed in an oven at 100 - 180 °C for 2-20 min. Washes were carried out with a mixture of water and alcohol until it was possible to isolate the modified starch. This form of surface modification of the starch is called one-step cross-linking.
  • cyclodextrin ester was previously obtained.
  • cyclodextrin was mixed with 1,2,3,4-butanetetracarboxylic acid (BTCA) and in contact with the catalyst sodium hypophosphite in an aqueous medium at 25-70 °C.
  • BTCA 1,2,3,4-butanetetracarboxylic acid
  • sodium hypophosphite sodium hypophosphite in an aqueous medium at 25-70 °C.
  • most of the water was evaporated until the mixture had a moisture content of less than 10%, either by being dried at room temperature for more than 18 h or by being heated.
  • the solid was then placed in an oven at temperatures between 80 and 180 °C for 1 to 10 min.
  • cyclodextrin ester The product, named cyclodextrin ester, was isolated by dissolving it in water, by rejecting the insoluble part, and by subsequent precipitation with an alcohol.
  • a starch was mixed with the cyclodextrin ester and in contact with the sodium hyposulphite catalyst in aqueous medium at temperatures from 25 to 70 °C. After observation of macroscopic homogeneity, most of the water was evaporated. The solid was then placed in an oven at 140-180 °C for 2-20 min. Washes with a water-alcohol mixture succeeded in isolating the modified starch obtained by two-step cross-linking.
  • the substitution of the main starch derivatives with cyclodextrin is shown quantified in Table 1.
  • the gravimetric method is based on the difference in weight of the native starch and the modified starch.
  • the spectrophotometric method is based on the absorption of phenolphthalein, which forms a 1:1 complex with beta-cyclodextrin.
  • Proton nuclear magnetic resonance spectra are shown in Figure 1 for beta-cyclodextrin, polycarboxylic acid and for the cyclodextrin ester. They allow to calculate the average degree of substitution of the cyclodextrin ester, which, in the case of having carried out the first esterification at 140 °C for 10 min and the second esterification at 160 °C for 5 min, is 2,410,1.
  • Attenuated total reflectance Fourier transform infrared spectroscopy are shown in Figure 2 for native and modified starch.
  • the most relevant absorption bands due to the elongation of a carbon-oxygen double bond that is not in the native starch, are marked.
  • This figure also shows the condensed structures of the substituted starch monomer.
  • An example of an ester bond, with an absorption band at 1718 cm -1 is marked with a star.
  • An example of a free carboxyl group, with an absorption band at 1560 cm -1 is marked with a ring.
  • Table 1 Quantification of beta-cyclodextrin content in modified starch.
  • the first number is provided by spectrophotometric determination; the second number corresponds to gravimetric estimation.
  • Type of cross-linking Cross-linking time Amount of beta-cyclodextrin/ (mmol/g) One-step 10 min 0.20-0.24 Two-steps 5 min 0.11-0.11 10 min 0.14-0.16
  • the modified starch has a higher molecular weight than the starting starch, in one embodiment of the invention, this was compensated for by prior hydrolysis.
  • the molecular weight of the polymer to be modified should be lower than the molecular weight of the polymer commonly used for paper coating.
  • the modified starch was redispersed in water under strong stirring and was heated to 65-110 °C. After 5-30 min, and upon observation of macroscopic homogeneity, it was allowed to cool to 25-60 °C without stopping the stirring. 0,01-2,00 g of an essential oil was added, and the suspension continued under stirring until macroscopic homogeneity was again observed.
  • the modified starch together with the essential oil, thus constituting the coating formulation was placed on the paper by coating with one or two rolls.
  • the modified starch and essential oil were placed on the paper by dipping it in an aqueous dispersion of modified starch and essential oil.
  • Table 2 shows the surface and optical properties of the paper coated by this method, with and without essential oil, compared with uncoated paper and the paper coated with unmodified starch.
  • the modified starch did not produce any reduction in whiteness and even good printing properties were maintained.
  • the reduction in air permeability or Gurley porosity as well as the reduction in roughness from the base paper were slightly less than using native starch.
  • the differences between starch and modified starch are minor in the case of permeability or not significant in the case of roughness.
  • GCMS mass spectrometry detector
  • An essential oil from eucalyptus wood was used because it contained not only volatile active compounds, but also compounds with a vapor pressure lower than 0.01 kPa at 25 °C. More specifically, this essential oil contained, as determined using the mentioned equipment: ⁇ -pinene: 55 mg/g; monoterpenes other than ⁇ -pinene: 3 mg/g; monoterpenoids (1,8-cineol, ⁇ -terpineol and ⁇ -terpinyl acetate): 202 mg/g; sesquiterpenes (aromadendrene and others): 125 mg/g; epiglobulol 95 mg/g; globulol: 295 mg/g; ⁇ -eudesmol: 35 mg/g; other sesquiterpenoids: 118 mg/g; esters: 40 mg/g; alkanes: 13 mg/g; aromatic hydrocarbons: 8 mg/g.
  • Headspace Solid Phase Microextraction consists of exposing a SPME fiber consisting of polydimethylsiloane, divinylbenzene and Carboxen ® to the vapors released from a sample of paper coated according to Example 1 and with native starch.
  • the fibre was inserted in the gas chromatograph, using the same column and configuration used for the determination of the oil composition, as mentioned above.
  • Table 3 shows the composition obtained after an extraction with ethanol, containing fluorobenzene at a concentration of 1 mg/mL.
  • high amounts of lower vapor pressure compounds namely epiglobulol, globulol and aromadendrene, were still present after the week of exposure.
  • no low molar mass compounds were detected by GCMS, except ⁇ -terpinyl acetate, which was found in very similar proportion in both cases.
  • Figure 5 refers to the evaluation of the antioxidant capacity, understood in terms of inhibition of the 2,2-diphenyl-1-picrylhydrazyl radical (DPPH).
  • DPPH 2,2-diphenyl-1-picrylhydrazyl radical
  • a 0,5 mM solution of DPPH was prepared in the above-mentioned mixture, MeOH/DCM. 2,5 mL of this solution was mixed with 0,5-2,5 mL of the extracts in MeOH/DCM. More MeOH/DCM was added until the volume was adjusted to 5 mL and the flask was kept out of light. After 1 h, the absorbance at 520 nm was calculated using a Shimadzu spectrophotometer, UV-2450.
  • the negative control assay was performed by an identical extraction with MeOH/DCM of the papers coated with native starch and modified starch, but without active compounds. Similarly, hydroxytyrosol itself was evaluated, directly using this compound extracted from the olive (fruit and leaves) instead of the paper extracts.
  • Figure 5A revealed a low IC50 value for the extract used, confirming its strong antioxidant capacity.
  • Figure 5B showed that after 4 days of exposure to air, papers containing modified starch retained higher antioxidant power than those coated with native starch.
  • the molecular weight of the starch normally used in surface treatments was reduced by hydrolysis with alpha-amylase: 0,45 ⁇ L of standard enzyme solution per gram of starch, 80 °C, 10 min, denaturation with zinc sulphate.
  • This modified starch was obtained in two-steps and was washed with a mixture of water and ethanol, 50% v/v.
  • This modified starch contained 0,11 mmol of cyclodextrin per gram of polymer.
  • a modified starch suspension was prepared as in the previous example. Instead of essential eucalyptus oil, 0,25 g of hydroxytyrosol, a compound with higher antioxidant activity, was added. An uncoated sheet of paper was impregnated in the modified starch and hydroxytyrosol suspension by means of the "KSV Nima Dip Coater" equipment for 20 s. This sheet had a mass gain of 7-9 g/m 2 compared to the uncoated sheet.
  • the long reaction at high temperature and low pH produced significant hydrolysis of cyclodextrin and starch, resulting in the presence of non-cyclic oligosaccharides, unreacted acid, and a lower viscosity than expected for its consistency.
  • the modified starch was isolated by precipitation, adding 100 mL of ethanol at room temperature (20 °C to 23 °C), and keeping the suspension, without stirring, at room temperature (20 °C to 23 °C) for at least 60 min. The ethanol/water soluble phase was discarded.
  • the collected solid was then redispersed, preparing a solution consonant with the previous examples.
  • 0,25 g of essential oil of eucalyptus leaves was added.
  • the mixture was then used to coat a sheet of paper by means of the coater mentioned above, at 6 m/min and under infrared radiation.
  • the coated sheet was dried on a metal plate by means of a thermoventilator at 50-60 °C for 20 min.
  • the resulting paper sheet had a mass gain of 1,5-2 g/m 2 compared to the uncoated sheet.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
EP23020166.7A 2022-03-31 2023-03-31 Méthode de revêtement d'une matière cellulosique Pending EP4253651A1 (fr)

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PT117894A PT117894A (pt) 2022-03-31 2022-03-31 Método de revestimento de material celulósico com óleos essenciais

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EP4253651A1 true EP4253651A1 (fr) 2023-10-04

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Citations (10)

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Publication number Priority date Publication date Assignee Title
EP0690170A1 (fr) 1994-06-29 1996-01-03 Coöperatieve Verkoop- en Productievereniging van Aardappelmeel en Derivaten 'AVEBE' B.A. Procédé pour encoller en surface et revêtir du papier
WO2001048025A1 (fr) * 1999-12-28 2001-07-05 Kimberly-Clark Worldwide, Inc. Cyclodextrines liees de maniere covalente a des polysaccharides
TW201102271A (en) 2009-07-03 2011-01-16 Chung Rhy Special Paper Mfg Co Ltd Oil-absorbing facial tissue containing natural plant dried matter and essential oil
CN102644217A (zh) 2011-02-17 2012-08-22 福建恒安集团有限公司 一种天然植物精油抗菌原纸
WO2013173434A1 (fr) * 2012-05-15 2013-11-21 Mantrose-Haeuser Co., Inc. Revêtement d'emballage alimentaire à base d'algues
CN109293789A (zh) * 2018-10-15 2019-02-01 天津工业大学 一种α-环糊精改性淀粉浆料及其制备方法
CN109403142A (zh) 2018-11-19 2019-03-01 贵州午留文化旅游特色商品开发有限公司 一种用于鞋内除臭灭菌的香薰纸及其制备方法
CN110055820A (zh) * 2019-03-06 2019-07-26 浙江工业大学 一种复合加强缓释的功能性保鲜纸基材料的制备方法
CN111691224A (zh) 2019-03-12 2020-09-22 瑞辰星生物技术（广州）有限公司 改性淀粉及其制备方法和应用
WO2021090190A1 (fr) * 2019-11-04 2021-05-14 Stora Enso Oyj Film cellulosique revêtu en surface

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EP0690170A1 (fr) 1994-06-29 1996-01-03 Coöperatieve Verkoop- en Productievereniging van Aardappelmeel en Derivaten 'AVEBE' B.A. Procédé pour encoller en surface et revêtir du papier
WO2001048025A1 (fr) * 1999-12-28 2001-07-05 Kimberly-Clark Worldwide, Inc. Cyclodextrines liees de maniere covalente a des polysaccharides
TW201102271A (en) 2009-07-03 2011-01-16 Chung Rhy Special Paper Mfg Co Ltd Oil-absorbing facial tissue containing natural plant dried matter and essential oil
CN102644217A (zh) 2011-02-17 2012-08-22 福建恒安集团有限公司 一种天然植物精油抗菌原纸
WO2013173434A1 (fr) * 2012-05-15 2013-11-21 Mantrose-Haeuser Co., Inc. Revêtement d'emballage alimentaire à base d'algues
CN109293789A (zh) * 2018-10-15 2019-02-01 天津工业大学 一种α-环糊精改性淀粉浆料及其制备方法
CN109403142A (zh) 2018-11-19 2019-03-01 贵州午留文化旅游特色商品开发有限公司 一种用于鞋内除臭灭菌的香薰纸及其制备方法
CN110055820A (zh) * 2019-03-06 2019-07-26 浙江工业大学 一种复合加强缓释的功能性保鲜纸基材料的制备方法
CN111691224A (zh) 2019-03-12 2020-09-22 瑞辰星生物技术（广州）有限公司 改性淀粉及其制备方法和应用
WO2021090190A1 (fr) * 2019-11-04 2021-05-14 Stora Enso Oyj Film cellulosique revêtu en surface

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