WO2007135273A2 - Materials based on a woven or non-woven textile substrate coated with a matrix, containing at least one antimicrobial agent and method for making same - Google Patents

Materials based on a woven or non-woven textile substrate coated with a matrix, containing at least one antimicrobial agent and method for making same Download PDF

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Publication number
WO2007135273A2
WO2007135273A2 PCT/FR2007/000815 FR2007000815W WO2007135273A2 WO 2007135273 A2 WO2007135273 A2 WO 2007135273A2 FR 2007000815 W FR2007000815 W FR 2007000815W WO 2007135273 A2 WO2007135273 A2 WO 2007135273A2
Authority
WO
WIPO (PCT)
Prior art keywords
characterized
antimicrobial agent
materials according
woven
polymer
Prior art date
Application number
PCT/FR2007/000815
Other languages
French (fr)
Other versions
WO2007135273A3 (en
Inventor
Afef Ben Arfa
Pascale Chalier
Nathalie Gontard
Laurence Preziosi-Belloy
Original Assignee
Universite Montpellier Ii
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority to FR06/04271 priority Critical
Priority to FR0604271A priority patent/FR2900940B1/en
Application filed by Universite Montpellier Ii filed Critical Universite Montpellier Ii
Publication of WO2007135273A2 publication Critical patent/WO2007135273A2/en
Publication of WO2007135273A3 publication Critical patent/WO2007135273A3/en

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Classifications

    • DTEXTILES; PAPER
    • D21PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21HPULP 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
    • D21H21/00Non-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
    • D21H21/14Non-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
    • D21H21/36Biocidal agents, e.g. fungicidal, bactericidal, insecticidal agents
    • DTEXTILES; PAPER
    • D21PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21HPULP 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
    • D21H19/00Coated paper; Coating material
    • D21H19/36Coatings with pigments
    • D21H19/44Coatings with pigments characterised by the other ingredients, e.g. the binder or dispersing agent
    • D21H19/50Proteins
    • DTEXTILES; PAPER
    • D21PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21HPULP 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
    • D21H19/00Coated paper; Coating material
    • D21H19/36Coatings with pigments
    • D21H19/44Coatings with pigments characterised by the other ingredients, e.g. the binder or dispersing agent
    • D21H19/54Starch
    • DTEXTILES; PAPER
    • D21PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21HPULP 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
    • D21H27/00Special paper not otherwise provided for, e.g. made by multi-step processes
    • D21H27/10Packing paper

Abstract

The invention concerns materials based on a woven or non-woven textile substrates coated with a matrix, characterized in that the matrix comprises one or more biodegradable polymers for controlled emission of one or more volatile antimicrobial agents incorporated in said polymers. The invention is useful in particular tor protecting products against the activity or development of microorganisms.

Description

Materials based on a fibrous support, woven or nonwoven coating of a matrix containing at least one antimicrobial agent and method of manufacturing

The invention relates to materials composed of a support based on fibers, woven or non-woven coated with a matrix containing at least one antimicrobial agent. It also concerns a process for the manufacture of these matrices and materials and materials applications coatings obtained.

The presence of microorganisms in the environment (air, water, soil) causes many alterations reducing the storage time and affects the quality of products. These deleterious effects can be dangerous in terms of security in the case of products to consume.

Antimicrobial agents are a means widely used to protect products, in particular to stabilize consumer products, especially food. They make it possible to inhibit, or at least reduce, the activity and the growth of microorganisms.

The addition of the antimicrobial agent can be directly incorporated into the product, or spray, but it may be advantageous to bring it through the packaging to limit its presence in the product. The pre-integration of the antimicrobial agent in a substrate or support, however, involves having an appropriate mode of incorporation to maintain the activity of the antimicrobial agent and his release under conditions ensuring the achievement of the effect longed for.

Direct contact of the antimicrobial agent with the product to preserve is not always possible, depending on the state of the surfaces to be treated, or even advisable in the case of fragile products. The inventors in this field have focused on the use of antimicrobial agents in volatile form and led to the development of new coating matrices and materials comprising these matrices, particularly suited for the incorporation of these agents.

The invention thus provides, with matrices and these materials, means for an effective time-release of the antimicrobial agent without the direct contact with the product being necessary.

The invention also aims to provide new matrices combining volatile antimicrobial agent a biopolymer capable of establishing specific interactions with the antimicrobial agent to limit the losses in the process and to ensure a controlled release of the compounds volatile antimicrobial activity.

It further provides a method for producing these coating dies and the easy implementation of materials and therefore usable on an industrial scale. With leveraging the properties of these active matrices, the invention also aims to provide product protection measures in sectors such as food, horticulture, cosmetics, pharmaceuticals, and generally for 'packaging.

The invention therefore relates to coating supports based on fibers, woven or nonwoven, with a polymer base matrix in which are incorporated one or more volatile antimicrobial agents whose emission is controlled by the polymer matrix .

"Antimicrobial agent" as used in the specification and claims, designates both a single compound formed a combination of, or containing several compounds.

According to the invention, the polymer matrix is ​​associated with the support and interacts with the antimicrobial agent, so as to allow the release of a controlled amount of the agent during a significant period. This matrix makes it possible to reversibly trapping the antimicrobial agent on the support, to reduce losses during the manufacturing process and to release, for example under the effect of humidity or temperature in contact with surrounding environment to protect the product. For environmental protection reasons, the polymeric material is selected among biodegradable polymers preferably of agricultural origin such as proteins or polysaccharides, which may be used alone or in mixtures.

Particularly suitable matrices include polymers having film-forming properties selected from proteins or isolates containing them. Preferred vegetable proteins include soy proteins or isolates, the wheat gluten protein. Animal proteins such as casein.

Alternatively, there may be used polysaccharides such as chitosan, acacia gum or native starches, hydrolyzed or modified, for example those of potato, wheat or corn. Modified starches are specifically chemically modified, for example by grafting hydrophobic chemical groups to impart emulsifying properties.

The antimicrobial agent of volatile nature is especially chosen from essential oils and their main components. These components include several classes of chemical molecules, such as phenols, alcohols, aldehydes, sulfur compounds, terpenes, lactones, pyrazines, ketones, ethers, esters and others.

As an antimicrobial agent of interest which may be mentioned carvacrol (from wild thyme and oregano), cinnamaldehyde (from cinnamon), allyl isothicyanate (AITC) (from mustard), trans- 2-hexenal (from tea), eugenol (from clove) and menthol

(From mint). These agents are used alone or in combination as shown in the tables given in the examples below.

Some microbial agents possess antioxidant activities, which will also ensure product protection against oxidation. They include carvacrol, cinnamaldehyde and eugenol, for example.

In an alternative embodiment of the invention, the antimicrobial agent is previously included in a capsule. Examples of materials constituting the capsules which may be mentioned cyclodextrins, or synthetic polymers such as polyurethanes or polyacrylic resins. The volatile compound is released by breakdown of the capsules (cyclodextrins), or by passive diffusion through the capsule synthetic polymers.

Polymeric matrices are in the form of one or more thin layers of about 10 to 100 microns, disposed (s) on the support and / or impregnating it.

The fibrous substrate used for the coating is a hydrophilic nature of media such as paper, cardboard, woven or nonwoven. It comprises for example organic fibers such as cellulosic fibers.

The invention also provides the method of manufacturing the fiber-based carrier material as defined above, coated with a matrix comprising the mixture of biodegradable polymers and antimicrobial agents as defined above. The material obtaining method then comprises

- a) applying one or more coatings on the fibrous support with the said mixture, and b) drying the coated support.

The mixture used in step a) is obtained by adding, at a temperature of 25 ° C, the volatile antimicrobial agent to an aqueous solution of the polymer which has undergone a preliminary heat treatment of 40 to 90 ° C (preferably 5O 0 C).

In another embodiment, the mixture further comprises a filler, such as talc. According to a variant of the invention mentioned above, the antimicrobial agent is encapsulated. The microencapsulation is carried out before the mixture of (s) the agent (s) and (des) polymer (s). The encapsulated agent is then in the form of powder or liquid.

The antimicrobial agent is introduced into the polymer solution at 5 to 50% by weight of dry matter of the polymer, especially from 10 to 35%.

For the purposes of application to the substrate, the formed mixture is preferably homogenized and spread on the support, for example by coating or coating, to form a desired layer thickness, generally from 5 to 50 g / m 2, in particular of about 10 g / m 2. The coating is advantageously carried out by a conventional device known as "Coater". Other examples of application methods include impregnation with a size press or Press Movie technique.

As illustrated by the following examples, the resulting materials have high antimicrobial activity, creating the environment of products to protect an atmosphere enriched with antimicrobial components. Releasing the antimicrobial agent for a reasonable length of time, these materials can limit or prevent the activity and the development of at least one kind of microorganisms, their spectrum of activity being conferred by the one or more antimicrobial agents that they understand. Targets are also many pathogenic microorganisms that microorganisms belonging to bacteria type of spoilage flora, yeasts or molds. By the presence of antimicrobial agents having, as mentioned above, anti-oxidant properties, the materials of the invention allow further protect the products against oxidation.

In particular, these interactive materials with the environment can be used with advantage in the food industry for preserving food by complying with all standards in horticulture where they effectively help to fight against the growth of microorganisms in systems filtration of gases, for example air.

Other features and advantages of the invention are given in the following examples which have no limiting character. In these examples, reference is made to the single figure which represents the effect of moisture on the release of carvacrol.

Example 1 Preparation of a paper support coated with a based on soy protein isolate matrix (IPS) containing carvacrol

A solution of IPS to 10% w / v is carried out in distilled water at 50 ° C under magnetic stirring for 30 min. The heat treatment of the IPS solution promotes homogeneity by reducing the particle size. After cooling to a temperature of 25 ° C, carvacrol is added at 32.6% w / w of IPS.

The solution is homogenized for 10 min at 8000 revolutions / min with a Ultraturrax or 10 min with a light. Coating the solution is carried out on a raw paper or has already undergone a surface treatment.

The coating is carried out using the means, techniques and tools, usual for coating paper. The solution is spread manually, but it can be done on industrial pilot using a grooved bar chosen based on the weight of the desired final layer, approximately 10 g / m 2 or using a micrometer applicator. Drying is carried out in the open air at 25 ° C, but it may advantageously be carried out without loss of compound at elevated temperatures of 250 ° C more commonly used in papermaking.

EXAMPLE 2 Preparation of paper support coated with a based on soy protein isolate matrix (IPS) containing carvacrol encapsulated in synthetic resins Capsules composed of synthetic resin, such as aminoplasts, and containing about 39% w / v of carvacrol are added at 30% w / w of dry matter to a cooled solution of IPS as obtained in example 1. the solution was homogenized using a pale or an Ultraturrax for 30 min at room temperature.

EXAMPLE 3 Preparation of paper support coated with a modified starch-based matrix containing carvacrol.

Starch solutions graft-modified with octenyl succinate to 20% w / v are formed by dissolving in distilled water at 50 ° C for 30 min with magnetic stirring. After cooling to a temperature of 25 ° C, carvacrol is added at 32.7% w / w of dry matter. The solution is homogenized with a pale or Ultraturrax for 30 min at room temperature.

Example 4 Preparation of a paper support coated with a matrix based on modified soy protein isolate containing cinnamaldehyde.

Of soy protein isolate solutions are prepared by dissolving in distilled water at 50 ° C for 30 min with magnetic stirring. After cooling to a temperature of 25 ° C, cinnamaldehyde is added at 32.7% w / w of dry matter. The solution is homogenized with a pale or Ultraturrax for 30 min at room temperature. Retention of the antimicrobial agent in the coated substrates

The following reports the results obtained with the coated substrates of Examples 1 to 4.

The residual amount of volatile antimicrobial agent in the coated papers was estimated a) after the coating step and drying

The results are given in Table 1 below.

Table 1

Nature of the matrix Percentage of Percentage added antimicrobial agent coating agent (w / w residual antimicrobial dry matter)

IPS 32.7 75

IPS + Capsules 30.7 AM 84 30 82

Examination of these results shows that the percentage loss in carvacrol after the coating and drying process is on average 20%. b) at different times of storage under accelerated conditions of issue (30 ° C, 60% RH)

The results for carvacrol are given in Table 2 below.

Table 2

Nature of the residual matrix Carvacrol residual Carvacrol residual coating Carvacrol extracted TLO (%) T25 extracted (%) extracted with T50 (%)

IPS 57.5 ± 2 5 44.6 ± 1.65 30 ± 2, 5

IPS + Capsules 84 ± 8 54.5 ± 5.7 25 ± 2 2

AM 84 ± 6 30 ± 6 23 ± 2, 1

It is found that the percentage of residual carvacrol, 50j after storage under accelerated conditions of issue, is on average 25%, which corresponds to a loss of the compound varying between 70 and 77%, depending on the nature of the matrix coating deposited on the paper. - release kinetics of the antimicrobial agent

Figure 1 shows the carvacrol release kinetics depending on the relative humidity at 30 ° C from a paper coated with soy protein isolate and comprising said carvacrol. The release is favored by the increase in relative humidity as well as that of the temperature. The release is indeed slower at 4 ° C or 20 0 C.

- Antimicrobial Activity of coated papers

For example the antimicrobial activity of coated papers was measured in particular on two different sensitivity of E. coli strains (IP54127) and L. plantarum (LP.1406). Antimicrobial activity is measured by the microatmosphere method. It consists of placing the coated paper to be tested in an environment close to a previously contaminated agar medium from a defined microbial suspension.

The results are given in Table 3 below.

Table 3

Nature of the IPS + IPS IPS + + + IPS matrix capsules carvacol Carvacrol Carvacrol of coating Carvacrol

Amount 1.07 1.35 3.76 1.99 ± 0.24 0.06 ± carvacrol ± 0.3 ± 0.06 (g / m 2)

E. coli

L plantarum +

The sign (-) indicates a lack of growth and the (+) growth of observation. Testing conducted by microatmosphere. IPS: Soy protein isolate; The initial load is 1 & -10 6 cells / ml

These results show that the different papers tested IPS + carvacrol at different concentrations, IPS + capsules carvacrol, exhibit antimicrobial activity effective vis-à-vis E. coli and L. plantarum provided that the amounts of antimicrobial agent in the paper are sufficient. Additional tests have shown the antimicrobial efficacy of modified starch-based paper and the effectiveness of these different papers on Botrytis cinerea. The antimicrobial activity is dependent on the amount of carvacrol and sensitivity of the microorganism, as well as the release rate of the antimicrobial agent. As shown in Figure 1, in which indicates the percent release versus time for the moisture content of 60, 80 and 100%, the release rate is more rapid than the humidity is high . This feature keeps the antimicrobial activity of paper during storage which must be done with low humidity and temperature and then release the agent in the product packaging.

The relative humidity and temperature contribute to his release. It should be noted that the anti-microbial development is favored at elevated HR hence the value of the materials used in controlled release point moisture.

Claims

1 / materials based on fibrous materials, woven or non-woven, coated with a matrix wherein the matrix comprises one or more biodegradable polymers allowing for the controlled emission of one or more volatile antimicrobial agents incorporated into said polymers.
2 / materials according to claim 1, characterized in that the polymer or polymers are chosen from biodegradable polymers from agricultural sources, such as proteins or polysaccharides.
3 / materials according to claim 2, characterized in that the polymer or polymers are chosen from vegetable and animal proteins or isolates containing them.
4 / materials according to claim 3, characterized in that the vegetable proteins include soy protein isolates or their, or proteins of wheat gluten and animal proteins include caseins.
5 / materials according to claim 2, characterized in that the polymer or polymers are polysaccharides selected from chitosan, acacia gum or hydrolysed or modified native starches, such as those of potato, wheat or corn. 6 / Materials according to any one of claims 1 to 5, characterized in that the antimicrobial agent of volatile nature is an antimicrobial agent selected from essential oils and their main components.
It materials according to claim 6, characterized in that the antimicrobial agent is selected from the group consisting of carvacrol, cinnamaldehyde, allyl isothiocyanate, trans-2-hexenal, eugenol and menthol, which compounds are used alone or in combination. 8 / materials according to claim 6 or 7, characterized in that the antimicrobial agent is included in a capsule.
9 / materials according to claim 6,7,8, characterized in that the antimicrobial agent used has further antioxidant activities. 10 / Materials according to any one of claims 1 to 8, characterized in that the matrices are in the form of one or more layers of about 10 to 100 microns, disposed (s) on the supports or impregnating them.
11 / materials according to claim 9, characterized in that the supports are fibrous, hydrophilic in nature such as paper, cardboard, woven or nonwoven. 12 / A method of manufacturing material according to any one of claims 1 to 10, characterized in that it comprises a) applying a coating on fibrous substrates with the polymer blend (s) biodegradable (s) and agent (s) antimicrobial (s) as defined in claims 1 to 8, and b) drying the coated support.
13 / A method according to claim 11, characterized in that the mixture used in step a) is obtained by adding, at a temperature of 25 ° C, the antimicrobial agent to an aqueous solution of the polymer having undergone treatment prior heat of about 5O 0 C.
14 / A method according to claim 11 or 12, characterized in that the antimicrobial agent is introduced into the polymer solution at 5 to 50% by weight of dry matter of the polymer, especially from 10 to 35%.
15 / A method according to any one of claims 12 to 14, characterized in that the mixture formed in step a), where appropriate supplemented with fillers is homogenized is spread on the support, for example by coating, to form a layer of desired thickness, generally 5 to 15g / m 2, preferably of the order of 10 g / m 2.
16 / The use of the materials according to any one of claims 1 to 10 for protecting products against the activity and the growth of microorganisms. 17 / The use of claim 16 for the protection of products against further oxidation.
18 / The use according to claim 15 for packaging in the food industry, to preserve foods, horticulture, in cosmetics and in the pharmaceutical field.
PCT/FR2007/000815 2006-05-12 2007-05-14 Materials based on a woven or non-woven textile substrate coated with a matrix, containing at least one antimicrobial agent and method for making same WO2007135273A2 (en)

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FR0604271A FR2900940B1 (en) 2006-05-12 2006-05-12 "Materials based on a fibrous support, woven or nonwoven coating of a matrix containing at least one antimicrobial agent and method of manufacture"

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WO2010069152A1 (en) * 2008-12-18 2010-06-24 香港科技大学 A multi-effect antimicrobial surface coating forming material and its preparation
CN102493208A (en) * 2011-12-06 2012-06-13 东华大学 Preparation method of polynosic fabric with skin caring and calming functions
CN102493182A (en) * 2011-12-06 2012-06-13 东华大学 Preparation method of Lyocell fabric with fatigue removing function
US8445032B2 (en) 2010-12-07 2013-05-21 Kimberly-Clark Worldwide, Inc. Melt-blended protein composition
CN103147310A (en) * 2013-03-27 2013-06-12 南通苏州大学纺织研究院 Method for finishing cotton fabrics through spraying plant essential oil
WO2013093659A1 (en) * 2011-12-19 2013-06-27 Kimberly-Clark Worldwide, Inc. Natural, multiple release and re-use compositions
US8524264B2 (en) 2010-12-07 2013-09-03 Kimberly-Clark Worldwide, Inc. Protein stabilized antimicrobial composition formed by melt processing
US20140154426A1 (en) * 2010-12-03 2014-06-05 Universidad De Santiago De Chile Process for Obtaining a Film Comprised of the Incorporation of Naturally-Sourced Antimicrobial Agents in a Polymeric Structure to Develop Packages for Increasing the Shelf Life of Refrigerated Meat, Preferentially Refrigerated Fresh Salmon
CN103966847A (en) * 2014-04-16 2014-08-06 南通大学 Method for finishing fabric through plant essential oil thermosensitive liposomes
US9149045B2 (en) 2010-12-07 2015-10-06 Kimberly-Clark Worldwide, Inc. Wipe coated with a botanical emulsion having antimicrobial properties
US9648874B2 (en) 2010-12-07 2017-05-16 Kimberly-Clark Worldwide, Inc. Natural, multiple use and re-use, user saturated wipes
WO2017175225A1 (en) * 2016-04-06 2017-10-12 Botanocap Ltd. Spoilage retardant multilayer materials containing food safe adhesives
US9832993B2 (en) 2010-12-07 2017-12-05 Kimberly-Clark Worldwide, Inc. Melt processed antimicrobial composition

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KR101308261B1 (en) * 2008-12-18 2013-09-13 더 홍콩 유니버시티 오브 사이언스 앤드 테크놀러지 A multi-effect antimicrobial surface coating forming material and its preparation
CN102149278A (en) * 2008-12-18 2011-08-10 香港科技大学 A multi-effect antimicrobial surface coating forming material and its preparation
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CN102149278B (en) 2008-12-18 2014-05-28 香港科技大学 A multi-effect antimicrobial surface coating forming material and its preparation
WO2010069152A1 (en) * 2008-12-18 2010-06-24 香港科技大学 A multi-effect antimicrobial surface coating forming material and its preparation
US20140154426A1 (en) * 2010-12-03 2014-06-05 Universidad De Santiago De Chile Process for Obtaining a Film Comprised of the Incorporation of Naturally-Sourced Antimicrobial Agents in a Polymeric Structure to Develop Packages for Increasing the Shelf Life of Refrigerated Meat, Preferentially Refrigerated Fresh Salmon
US9149045B2 (en) 2010-12-07 2015-10-06 Kimberly-Clark Worldwide, Inc. Wipe coated with a botanical emulsion having antimicrobial properties
US9648874B2 (en) 2010-12-07 2017-05-16 Kimberly-Clark Worldwide, Inc. Natural, multiple use and re-use, user saturated wipes
US9271487B2 (en) 2010-12-07 2016-03-01 Kimberly-Clark Worldwide, Inc. Protein stabilized antimicrobial composition formed by melt processing
US9205152B2 (en) 2010-12-07 2015-12-08 Kimberly-Clark Worldwide, Inc. Melt-blended protein composition
US8445032B2 (en) 2010-12-07 2013-05-21 Kimberly-Clark Worldwide, Inc. Melt-blended protein composition
US8524264B2 (en) 2010-12-07 2013-09-03 Kimberly-Clark Worldwide, Inc. Protein stabilized antimicrobial composition formed by melt processing
US9832993B2 (en) 2010-12-07 2017-12-05 Kimberly-Clark Worldwide, Inc. Melt processed antimicrobial composition
CN102493208A (en) * 2011-12-06 2012-06-13 东华大学 Preparation method of polynosic fabric with skin caring and calming functions
CN102493182A (en) * 2011-12-06 2012-06-13 东华大学 Preparation method of Lyocell fabric with fatigue removing function
US8574628B2 (en) 2011-12-19 2013-11-05 Kimberly-Clark Worldwide, Inc. Natural, multiple release and re-use compositions
WO2013093659A1 (en) * 2011-12-19 2013-06-27 Kimberly-Clark Worldwide, Inc. Natural, multiple release and re-use compositions
CN103147310A (en) * 2013-03-27 2013-06-12 南通苏州大学纺织研究院 Method for finishing cotton fabrics through spraying plant essential oil
CN103966847A (en) * 2014-04-16 2014-08-06 南通大学 Method for finishing fabric through plant essential oil thermosensitive liposomes
WO2017175225A1 (en) * 2016-04-06 2017-10-12 Botanocap Ltd. Spoilage retardant multilayer materials containing food safe adhesives

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Publication number Publication date
WO2007135273A3 (en) 2008-01-24
FR2900940B1 (en) 2008-07-18
FR2900940A1 (en) 2007-11-16

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