WO2007135245A1 - Matériau polymère antimicrobien et son utilisation - Google Patents

Matériau polymère antimicrobien et son utilisation Download PDF

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Publication number
WO2007135245A1
WO2007135245A1 PCT/FI2007/050296 FI2007050296W WO2007135245A1 WO 2007135245 A1 WO2007135245 A1 WO 2007135245A1 FI 2007050296 W FI2007050296 W FI 2007050296W WO 2007135245 A1 WO2007135245 A1 WO 2007135245A1
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WO
WIPO (PCT)
Prior art keywords
polysaccharide
cellulose
carbamate
fiber
wood
Prior art date
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.)
Ceased
Application number
PCT/FI2007/050296
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English (en)
Inventor
Torolf LAXÉN
Heikki Hassi
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SCITECH-SERVICE Ltd Oy
Original Assignee
SCITECH-SERVICE Ltd Oy
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Filing date
Publication date
Application filed by SCITECH-SERVICE Ltd Oy filed Critical SCITECH-SERVICE Ltd Oy
Publication of WO2007135245A1 publication Critical patent/WO2007135245A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/18—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic ring
    • 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
    • D21H11/00—Pulp or paper, comprising cellulose or lignocellulose fibres of natural origin only
    • D21H11/16—Pulp or paper, comprising cellulose or lignocellulose fibres of natural origin only modified by a particular after-treatment
    • D21H11/20—Chemically or biochemically modified fibres
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B15/00—Preparation of other cellulose derivatives or modified cellulose, e.g. complexes
    • C08B15/05—Derivatives containing elements other than carbon, hydrogen, oxygen, halogens or sulfur
    • C08B15/06—Derivatives containing elements other than carbon, hydrogen, oxygen, halogens or sulfur containing nitrogen, e.g. carbamates
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B31/00—Preparation of derivatives of starch
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
    • C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
    • C08B37/0045—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid alpha-D-Galacturonans, e.g. methyl ester of (alpha-1,4)-linked D-galacturonic acid units, i.e. pectin, or hydrolysis product of methyl ester of alpha-1,4-linked D-galacturonic acid units, i.e. pectinic acid; Derivatives thereof
    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F2/00—Monocomponent artificial filaments or the like of cellulose or cellulose derivatives; Manufacture thereof
    • D01F2/24—Monocomponent artificial filaments or the like of cellulose or cellulose derivatives; Manufacture thereof from cellulose derivatives
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/402—Amides imides, sulfamic acids
    • D06M13/425—Carbamic or thiocarbamic acids or derivatives thereof, e.g. urethanes
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/402—Amides imides, sulfamic acids
    • D06M13/432—Urea, thiourea or derivatives thereof, e.g. biurets; Urea-inclusion compounds; Dicyanamides; Carbodiimides; Guanidines, e.g. dicyandiamides
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M16/00—Biochemical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. enzymatic
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21C—PRODUCTION OF CELLULOSE BY REMOVING NON-CELLULOSE SUBSTANCES FROM CELLULOSE-CONTAINING MATERIALS; REGENERATION OF PULPING LIQUORS; APPARATUS THEREFOR
    • D21C9/00—After-treatment of cellulose pulp, e.g. of wood pulp, or cotton linters ; Treatment of dilute or dewatered pulp or process improvement taking place after obtaining the raw cellulosic material and not provided for elsewhere
    • D21C9/001—Modification of pulp properties
    • D21C9/002—Modification of pulp properties by chemical means; preparation of dewatered pulp, e.g. in sheet or bulk form, containing special additives
    • D21C9/005—Modification of pulp properties by chemical means; preparation of dewatered pulp, e.g. in sheet or bulk form, containing special additives organic compounds
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2101/00—Chemical constitution of the fibres, threads, yarns, fabrics or fibrous goods made from such materials, to be treated
    • D06M2101/02—Natural fibres, other than mineral fibres
    • D06M2101/04—Vegetal fibres
    • D06M2101/06—Vegetal fibres cellulosic
    • 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

Definitions

  • the present invention relates to the field of polysaccharides, especially to providing mi- crobistatic, i.e. bacterio- and fungistatic properties to said polysaccharides so that microbial growth in said polysaccharide and the microbial degradation of the polysaccharide is prevented or blocked.
  • the polysaccharide is blocked from microbial degradation, i.e. splitting of the saccharide chain, by introducing therein a blocking group, namely a carbamate group.
  • a blocking group namely a carbamate group.
  • the invention can also be used for imparting degradation preventing properties to polysaccharides, for example to cellulose based products, such as wood, or wood and paper and viscose fibers, by subjecting said products to a treatment imparting the desired blocking properties to the prod- uct by introducing a blocking group in a saccharide unit.
  • Cellulose has been converted to cellulose carbamate by means of urea and an alkaline agent in order to render the cellulose soluble.
  • the cellulose is then regenerated from the cellulose carbamate for the formation into various final cellulose products in the form of, for example, fibers, films or membranes.
  • cellulose carbamate is a chemically stable cellulose derivative, which also can be used as such, for the formation of various products.
  • hexachlorophene as a bacteriostatic agent, which is complexed with a zirconium salt and a finish of the cross-linking wash-wear type.
  • the cross-linking agent can be e.g. dimethylol methyl carbamate. ).
  • a cellulose carbamate sponge impregnated with silver nitrate and possessing antibacterial properties is disclosed.
  • the present invention relates to a method of imparting microbistatic properties to a polysaccharide, or to a polysaccharide containing product, for example a natural or man-made composite structure, like, e.g., wood, wood pulp, non-wood pulp, fiber webs, fabrics, or regenerated cellulose or products made thereof, by introducing covalently bound carbamate groups in the polysaccharide chain.
  • the microbistatic properties are thus a result of modifying the polysaccharide to comprise carbamate groups.
  • the invention is also directed to the use of a polysaccharide carrying carbamate groups covalently bound to the polysaccharide chain as a microbistatic material, and in the manufacture of a product or material having microbistatic properties due to carbamate groups covalently bound to a polysaccharide chain.
  • the invention is also related to a method of preparing various microbistatic products from cellulose carbamate by spinning, extruding, casting etc. the dissolved cellulose carbamate, i.e. without regenerating the cellulose component.
  • the carbamate groups in polysaccharide will thus provide the desired antimicrobial property to the product made.
  • the polysaccharide backbone that can be used according to the invention is derived from at least one natural polysaccharide selected from the group consisting of cellulose, hemi- cellulose, starch, pectine, amylopectine, and amylose.
  • a preferred polysaccharide is cel- lulose.
  • the cellulose can be in the form of cellulose fiber pulp, such as paper fiber or viscose (dissolving) fiber. It may appear, for example, as sulfate pulp, sulfite pulp, return fiber, CTMP pulp, TMP pulp, mechanical pulp or refiner pulp.
  • the polysaccharide material can also originate from natural fiber sources like cotton or linen (flax).
  • the polysaccharide to be treated in order to introduce the carbamate group can be in any form. Possibilities range from the case of a free polymer molecule to a polysaccharide in a piece of wood or timber. In the latter case, the polysaccharide is thus treated when present in the wood fiber, especially at a surface area of said wood or timber.
  • wood products or pieces of wood or timber to be treated are typically wood to be used for con- struction purposes, such as veneer or boards, such as particle board, planks, beams, battens, pillars and posts.
  • Such fiber polysaccharides can be made microbistatic by treating the said fibers in order to incorporate into a monosaccharide unit a carbamate group in order to provide such wood with anti-rot properties and/or to make them decay resistant.
  • the invention also contemplates carbamation of pure regenerated cellulose, for example in the form of a membrane, fabric, textile fiber or filament, as a way of providing microbial protection to the said regenerated cellulose.
  • Microcrystalline cellulose used in various applications e.g. in the pharmaceutical indus- try, may be carbamated to obtain microbistatic properties, and used according to the present invention.
  • Carbamates are chemically defined as esters of carbamic acid or its N-substituted derivatives.
  • the position of substitution of the carbamate group is preferably at a primary hydroxyl group.
  • the polysaccharide is cellulose in which case the carbamate group is preferably substituted to the hydroxyl group in the position 6 of the anhydroglucose unit of cellulose, while a carbamate group also can be formed to hydroxyl groups in carbon atoms number 2 and 3.
  • the degree of substitution (DS), i.e. the number of carbamate groups per one monosaccharide (or one anhydroglucose) unit can vary, the maximum degree of substitution being the number of hydroxyl groups in the respective monosaccharide unit.
  • the maximum degree of substitution is 3; however for the purposes of the present invention, a suitable and sufficient degree of substitution varies depending on the type of the polysaccharide substrate and the chemical accessibility of the hydroxyl groups for the substitution reaction.
  • a degree of substitution (DS) of 0.3 thus means that there is on an average 3 carbamate groups for every 10 monosaccharide units.
  • a suitable degree of substitution is in the range 0.05 to 1, preferably 0.25 to 0.4, more preferably 0.2 - 0.3.
  • a membrane made of regenerated cellulose can be made microbistatic by adding less that 1 carbamate group on an average of 10 monosaccharidic units.
  • a textile f ⁇ er made of regenerated cellulose requires a somewhat higher degree of substitution, since it has higher amount of specific surface, which is accessible for microbes.
  • Wood pulp or paper made of such wood pulp typically requires a DS of 0.2 to 1.0, depending of the amount specific accessible surface of the wood pulp and the desired level of mi- crobistaticity. Wood has even less polysaccharide molecules which are accessible to microbes, and, accordingly, a lower DS is needed for blocking these polysaccharide molecules against microbial degradation.
  • the accessibility of the hydroxyl groups for the carbamation reagent is enhanced by adding alkali to the water based suspension of wood pulp, thus allowing a higher de- gree of substitution to be achieved.
  • a degree of substitution in the range 0.25 - 0.4 makes the wood pulp alkali soluble.
  • An alkaline solution of cellulose carbamate can then be processed to form fibers, films, membranes, etc. Microbistatic property can be achieved by a lower degree of substitution.
  • the DS may typically remain below 0.1, e.g 0.05.
  • the carbamate group can be introduced in the polysaccharide by known methods.
  • the polysaccharide such as cellulose
  • the polysaccharide is treated with urea in an alkaline solution and then heated, whereby urea is converted to isocyanic acid, which easily reacts with a hydroxyl group in the polysaccharide to form the carbamate group.
  • the product obtained can be further treated for example washed and dried, in a known manner, to yield the desired polysaccharide carbamate.
  • the solution obtained can be spun to form a textile fiber, or extruded to a film or membrane, by precipitating the polysaccharide carbamate as a stable product in an acid or salt solution.
  • the invention also concerns a method of imparting microbistatic properties to a product or a material comprising manufacturing said product or material from, or incor- porating into said product or material a microbistatically effective amount of a polysaccharide carrying covalently bound carbamate groups.
  • the carbamate substituted polysaccharide or a polysaccharide based structure such as wood, wood fiber, other plant fibers, can be used as a timber, fiber pulp, fiber web or tissue, filament, fiber wool, for example for insulation purposes, as a film, as a non-woven, a textile, a fabric, in paper and paper products, and paper board, having microbistatic properties.
  • a typical use of a microbistatic polysaccharide according to the invention, or a product or material comprising the same, is in hygiene and healthcare.
  • Such uses include the use in textiles and nonwovens for example for hospital gowns, sterilization bags, sheets and linens, dressings, and other wound care materials, and wipes, including wet wipes, in baby napkins and similar sanitary products in which a microbistatic and antimicrobial effect is desirable.
  • Other uses include the use of the polysaccharide carbamates as degradation resistant insulation materials, such as in sheet form, or as insulation wools, made from the said polysaccharide, such as cellulose carbamate fibers.
  • Another conceivable use is as filters, for example in vehicle and aircraft cabin air filters, and in cleaning and household wipes.
  • Figure 1 shows alternative routes to products having properties according to the inven- tion.
  • Viscose pulp (dissolving pulp) prepared according to the state of the art may be treated to yield cellulose carbamate, which may be directly converted into end-use products.
  • the cellulose carbamate may also be dissolved as described above, and fibers, film or other solid forms may be prepared by mild acid treatment. These solids forms may be used to prepare end products. Acid treatment in stronger conditions splits off the car- bamate groups to yield regenerated cellulose. Various degrees of incomplete regeneration can be employed to control the degree of substitution.
  • the regenerated cellulose is of high purity and may be used as such, but may also be recarbamated to produce further grades of cellulose carbamate to be converted into end products.
  • a further aspect of the invention contemplates the treatment of polysaccharides in the form of fibers in a wood product or in timber, in order to introduce into the polysaccha- ride covalently bound carbamate groups as defined above.
  • wood and especially wood surfaces such as veneers and boards
  • an antimicrobial finish in relation to the case of dissolving pulp, the degree of substi- tution thereby remains lower, and a lower temperature and less severe chemical conditions may be used for treating surface regions that are subject to microbial attack.
  • the treatment may, if desired, be limited to the surface layers or a single surface layer.
  • Dissolving pulp was disintegrated in water and treated with a solution containing 37 % w/w of urea and 4,5 % w/w sodium hydroxide in water for twenty minutes. The sample was there after drained and pressed to a consistency of 25-30%. Next stage was fluffing and then drying of the sample in two stages at 70 0 C and 130 0 C. The dry sample was then heated to 165°C for 30 minutes. The resulting cellulose carbamate disintegrated in water at 5% suspension washed with water and dried.
  • the sample was examined for microbial activity according to the TAPPI method T 449 om-90. The result of the examination was:

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Biochemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Textile Engineering (AREA)
  • Materials Engineering (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • General Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Dentistry (AREA)
  • Microbiology (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Molecular Biology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)
  • Materials For Medical Uses (AREA)
  • Treatments Of Macromolecular Shaped Articles (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

La présente invention concerne un procédé pour conférer des propriétés microbiostatiques à un polysaccharide ou à un produit contenant un polysaccharide, par introduction dans la chaîne polysaccharide de groupes carbamates liés par covalence. Le polysaccharide peut être sous forme isolée ou inclus dans une structure complexe. Plus particulièrement, l'invention concerne l'utilisation de carbamate de cellulose pour la production d'un matériau microbiostatique. Un tel matériau peut se présenter sous forme de fibres ou de films ou sous forme de produits en bois traité de façon à les rendre imputrescibles.
PCT/FI2007/050296 2006-05-24 2007-05-24 Matériau polymère antimicrobien et son utilisation Ceased WO2007135245A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FI20065350A FI20065350A7 (fi) 2006-05-24 2006-05-24 Antimikrobinen polymeerimateriaali ja sen käyttö
FI20065350 2006-05-24

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WO2007135245A1 true WO2007135245A1 (fr) 2007-11-29

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PCT/FI2007/050296 Ceased WO2007135245A1 (fr) 2006-05-24 2007-05-24 Matériau polymère antimicrobien et son utilisation

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WO (1) WO2007135245A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101871167A (zh) * 2010-06-29 2010-10-27 常州大学 一种抗菌纤维素织物的制备方法
WO2011116403A3 (fr) * 2010-03-23 2011-11-24 Universität Innsbruck Procédé de préparation d'un polysaccharide contenant de l'azote
WO2013132061A1 (fr) 2012-03-09 2013-09-12 Friedrich-Schiller-Universität Jena Dérivés d'oligosaccharide et de polysaccharide modifiés par une amine de manière bifonctionnelle et multifonctionnelle en tant que substances anti-infectieuses et utilisation desdits dérivés

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002024420A1 (fr) * 2000-09-21 2002-03-28 Atelier Regional De Conservation Arc-Nucleart Procede de traitement chimique d'un substrat.
WO2003099873A1 (fr) * 2002-05-24 2003-12-04 Zimmer Aktiengesellschaft Procede de production de carbamate de cellulose
WO2004022846A2 (fr) * 2002-09-04 2004-03-18 Lonza Inc. Lubrifiant antimicrobien pour composites plastiques contenant des fibres
US20040091977A1 (en) * 2001-10-16 2004-05-13 Teeri Tuula Tellervo Mehtod for the modification of polymeric carbohydrate materials

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002024420A1 (fr) * 2000-09-21 2002-03-28 Atelier Regional De Conservation Arc-Nucleart Procede de traitement chimique d'un substrat.
US20040091977A1 (en) * 2001-10-16 2004-05-13 Teeri Tuula Tellervo Mehtod for the modification of polymeric carbohydrate materials
WO2003099873A1 (fr) * 2002-05-24 2003-12-04 Zimmer Aktiengesellschaft Procede de production de carbamate de cellulose
WO2004022846A2 (fr) * 2002-09-04 2004-03-18 Lonza Inc. Lubrifiant antimicrobien pour composites plastiques contenant des fibres

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
RATAJSKA M. ET AL.: "Physical and chemical aspects of biodegradation of natural polymers", REACTIVE & FUNCTIONAL POLYMERS, vol. 38, 1998, pages 35 - 49, XP004147134 *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011116403A3 (fr) * 2010-03-23 2011-11-24 Universität Innsbruck Procédé de préparation d'un polysaccharide contenant de l'azote
CN101871167A (zh) * 2010-06-29 2010-10-27 常州大学 一种抗菌纤维素织物的制备方法
WO2013132061A1 (fr) 2012-03-09 2013-09-12 Friedrich-Schiller-Universität Jena Dérivés d'oligosaccharide et de polysaccharide modifiés par une amine de manière bifonctionnelle et multifonctionnelle en tant que substances anti-infectieuses et utilisation desdits dérivés

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FI20065350A0 (fi) 2006-05-24
FI20065350L (fi) 2007-11-25
FI20065350A7 (fi) 2007-11-25

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