WO2002102156A1 - Composition de protection, et kit et procede permettant sa production et son utilisation - Google Patents

Composition de protection, et kit et procede permettant sa production et son utilisation Download PDF

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Publication number
WO2002102156A1
WO2002102156A1 PCT/NO2002/000185 NO0200185W WO02102156A1 WO 2002102156 A1 WO2002102156 A1 WO 2002102156A1 NO 0200185 W NO0200185 W NO 0200185W WO 02102156 A1 WO02102156 A1 WO 02102156A1
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WO
WIPO (PCT)
Prior art keywords
chitosan
composition
anion
substrate
preservative
Prior art date
Application number
PCT/NO2002/000185
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English (en)
Inventor
Mikal Mikalsen
Arne Ragnar ÖRSTAVIK
Rune Andre Falck
Eivind STEINSTÖ
Original Assignee
Multimar As
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Filing date
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Publication of WO2002102156A1 publication Critical patent/WO2002102156A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/14—Paints containing biocides, e.g. fungicides, insecticides or pesticides
    • 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
    • A01N43/16—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with oxygen as the ring hetero atom

Definitions

  • the present invention relates to a chitosan-containing preservative composition and a method for its production as defined by the preamble of claim 1 and claim 5 respectively.
  • the invention further relates to a preservative composition kit and different methods of preservative treatment, as well as different uses of the chitosan preservative composition and the preservative composition kit respectively.
  • the invention relates to different products having been treated with the chitosan-containing preservative composition.
  • preservative an impregnation agent which is environmentally friendly and not contains toxic compounds.
  • This relates to preservatives for marine uses as well as land-based uses.
  • Liquid preservatives used today e.g. for fish farming nets contains toxic copper compounds and other toxicants, while preservatives for land based wood contains arsenic oxide, toxic phenols and other toxic compounds. These toxicants are not desirable in preservatives, but are used in lack of alternatives of more environmentally friendly agents.
  • the existing fire retardants comprise e.g. ammonium borate and other types of ammonium compounds that are more or less toxic.
  • ammonium compounds are easily washed out of materials and the aging process is rapid and lifetime correspondingly short.
  • Acetic anhydride is also used for pressure impregnated wood to obtain a fire retardant effect. None of these substances give an adequate fire retarding effect, and many of them cannot be used indoors, as they may release toxic gases under influence of strong heat.
  • Chitosan is a modified form of chitin and the modification can take place by different deacetylation processes. Deacetylation takes place by separating the acetyl group from the (rest of the) chitin molecule.
  • Chitin is found in shellfish, insects, octopus etc. and in some plants, but are mainly extracted from shellfish like shrimps, crab etc. It is assumed that these animals have had the same structure of the chitin for protection against e.g. parasites for more than 600 million years, and chitin is one of the oldest polymers on earth together with cellulose. It can thus be said that nature itself has these two types of saccharides are ideal and therefore the two organic materials produced most widely in the nature.
  • the natural production of chitin from living organisms is estimated to 100-200 x 10 9 tons per year. The utilization of this worldwide is less than 1%, where the chitin mainly is regarded as a waste problem. The availability of chitin as a raw material is thus very good.
  • Chitosan and other types of polysaccharides and polymers have been tried in several ways as a preservative against fungus and rot in wood. Chitosan alone has shown a good protective effect, but with the present technology a high concentration of chitosan in required. In addition it is easily washed out, so its use as a commercial preservative is therefore limited.
  • US patent No. 5,549,739 describes a wood modifier composition comprising chitosan.
  • the composition described concerns chitosan in a form soluble in water and with a molecular weight between 320 and 48,000, which composition also includes colloidal silica. According to the patent the chitosan can be enzymatically depolymerized. Industrial scale treatment with the modifier according to this patent will be expensive and complex.
  • a common feature for all these agents and especially the fire retardants is that the aging process is rapid so they lose their ability to protect the wood. This is due to the fact that a lot of the compounds are washed out or disappear in other ways. The aging process, which mainly takes place due to external influences, may lead to a complete loss of the protective effect after some time.
  • fire retardants do not provide a deep penetration of the wood.
  • the fire retarding effect is thus limited to the outer part of the wood and the protective effect may be lost completely if the wood is subjected to a further preparation.
  • the object of the present invention is therefore to provide a preservative that is environmentally friendly, i.e. which is not toxic, and which can cover substantially all application areas of the traditional, toxic preservatives.
  • the invention relates to a preservative composition as defined by the characterizing part of claim 1 and claim 25. Preferred embodiments of the preservative composition are disclosed by the claims 2-20. The invention also relates to a composition kit as defined by claim 21, preferred embodiments of which are disclosed by claims 22-24. The invention further relates to a method for the manufacture of the preservative as defined by the characterizing part of claim 26. Preferred embodiments of the method are disclosed by claims 27-30.
  • the invention still further relates to methods for treatment of substrates with said method as defined by claims 31-42.
  • the invention still further relates to different uses of the preservative as defined by the claims 43-47.
  • the invention relates to different products as treated with preservative as defined by claims 48-51.
  • the modified chitosan is immobilized in the substrate at low concentrations in a way that it will not be washed out, dissolve or disappear in any other way, while providing a protective effect.
  • the chitosan is first dissolved in an acid, like formic acid or another organic acid or a combination of such acids. Mineral acids can also be used with the exception of sulphuric acid, which is not able to dissolve the chitosan.
  • the chitosan is if necessary depolymerized, e.g. to a viscosity of 10 cP or lower, by means of an oxidizing agent like hydrogen peroxide, sodium hypochlorite or the like.
  • the depolymerization step has the function of reducing the viscosity of the preservative. For use as an impregnation fluid for wood, the depolymerization is typically carried out until the viscosity is less than 10 cP.
  • an anion able to form a relatively water- insoluble complex with chitosan is added.
  • the normal way to add the anion will be as a salt where the counter ion is an environmentally friendly or acceptable cation.
  • the addition of the anion may some times be referred to as the addition of the salt. Due to the increased stability that the anion provides to the chitosan, the anion (and/ or the salt) according to the invention is sometimes referred to as a stabilizer in the following text.
  • the salt including the anion of the invention is added to the water together with non-dissolved chitosan, whereafter the acid is added, causing the chitosan to dissolve in the solution.
  • the salt is preferably chosen from a group including sulphites, phosphites, benzoates, phenolates, anhydrides and sulphamines.
  • the salt is preferably added in a concentration low enough to avoid precipitation of chitosan, typically in the range 0.1 - 10% by weigth.
  • the chitosan solution is then applied to a material (substrate) e.g. by mechanical applicators or by means of pressure, alternatively a combination of vacuum and pressure. For pressure impregnation, equipment conventional therefor may be utilized.
  • the chitosan By dissolving the chitosan in acid, the chitosan will react will the acid.
  • the pH should not, however, be reduced to a value lower than 4. If the pH accidentally is reduced too much, adding carbonates, e.g. ammonium hydrogen carbonate to the desired level prior to adding the salt, may raise it.
  • sulphite as an example of the preferred salt.
  • the oxygen in the air will oxidize the sulphite to sulphate.
  • the inventors have discovered that while the chitosan complexes according to the invention have a limited water-solubility in the free, powder form, and they become practically water-insoluble when impregnated into a substrate and thereby immobilized within the internal structure of the substrate.
  • the impregnated material will comprise chitosan, sulphite/ sulphate and salts of the organic acid utilized, e.g. chitosan formmate.
  • Ammonium is known to have a fire retardant effect.
  • ammonium sulphite could be used as a stabilizer in the chitosan solution.
  • a binding between the chitosan and the ammonium will be formed during drying with the formation of ammonium sulphamine glucose (ammonium chitosan sulphite), ammonium sulphamine, chitosan sulphate and e.g. ammonium forminate or other ammonium salts of the acid used to dissolve the chitosan.
  • Ammonium may also be used as the counterion in other salts within the frame of the invention, like phosphite, benzoate, anhydride, sulphamine and the like.
  • ammonium sulphite forms chitosan sulphate and ammonium sulphamine glucose (ammonium chitosan sulphite) with the chitosan.
  • Ammonium sulphamine also known as AMS, is used as a weed-killer and a fire retardant. These substances alone can not be used in a marine environment as they very easily dissolve in water and rapidly will be washed out. When the ammonium compound is bound to chitosan, however, neither the chitosan nor the ammonium compound will be easily dissolved, and they will therefore keep and enhance their protective effect for a substantial period of time.
  • the preservative according to the invention may also be used in liquid or dehydrated form as a soil improver and herbicide. Used in the form of a dry powder not impregnated into a substrate, the solubility is higher than for the corresponding complex in a substrate. It may also be applied as a soil improver in the form of wood chips from sawing and working of impregnated wood, in which case it will remain in the soil for a longer period of time, as it will not easily decompose. Wood chips of this kind may also be used in fire retardant chipboards or the like.
  • the chitosan solution may further be used in painting and cement or as a primer for plastic materials like polyester or the like.
  • the preservative according to the invention also relates to pressure impregnation of timber logs of freshly cut spruce, which is known not to receive impregnation any deeper than 3 mm into the wood, due to the fact that the cell structure will close during the process.
  • Impregnated wood is preferably ground to chips for use in chipboards or the like, but not for soil improvement if it is not known in what kind of environment it has been used.
  • the step of depolymerizing the chitosan has the function of reducing its viscosity, which may be required for some areas of application, like impregnation of wood. For other application areas, like impregnation of textiles or fish farming nets, this step may be omitted or carried out to a lesser degree.
  • the inventors have found that impregnating ropes, fish farming nets etc. with the preservative according to the invention, as a secondary effect, enhances the strength of the substrate and delays its aging. These effects also vary with the degree of depolymerization of the chitosan. Generally it can be said that the optimal viscosity and hence the required degree of depolymerization could be developed by trial and error for each relevant use.
  • Chitosan with varying chain lengths belonging to poly-, oligo- and monosaccharides respectively, may also be used in combination. While the combination of sulphite and chitosan is slowly oxidized under formation of the desired insoluble complex, the formation of complexes may occur much more rapid for other combinations according the invention. When the formation of complexes is quite rapid, the preservative may not be kept as a stable solution in the presence of air. In such cases it is preferred that the different components of the preservative are added separately to the substrate to be impregnated. The process may then be conducted as a two or three step reaction. The first step typically involves applying a chitosan solution alone, preferably followed by a drying period. Thereafter a solution of the salt is applied, leading to in situ formation of the insoluble preservative (complex) within the substrate.
  • Soil improvement Chitosan in solid form for example impregnated into chips of wood may be used directly or be ground to a fine powder that is worked into the soil, or spread on top of it. It can also be applied in the form of pellets or the like. It will work as a fertilizer for the plants and at the same time as a herbicide.
  • the decay (release) process starts due to the enzyme in the plant roots, the chitosan will enhance the plant's ability to resist attack from fungus and bacteria, while the ammonium sulphate will contribute as a nitrogen source.
  • This decay process is slower than for traditional nitrogen-containing fertilizers and will therefore hold up for a longer time in the soil and not represent the same danger for contamination as traditional fertilizers, where the nitrogen is washed out more rapidly.
  • the solution should have a pH of 5 - 6 when applied to the soil.
  • a chitosan solution with a pH in the range 5.5 - 6.5 is sprayed on utility plants to avoid attack from fungus, rot and insects.
  • the chitosan will lie as a breathing film over the plants and protect them against attack, while the plants simultaneously exploit the chitosan, this way improving the resistance against disease attacks.
  • the plants need repetitive treatments of the chitosan solution as they consume it over time.
  • the chitosan solution may also be spread on the ground as a dry powder, not immobilized within a substrate, and will also in this condition prevent growth of fungus and weed. Additive to paints/ primers etc.
  • a chitosan solution may be worked into the paint base or used alone.
  • the chitosan When the chitosan is added to the paint, it could first be neutralized and/ or have sulphate/ sulphite added prior to its addition to the paint.
  • the chitosan will this way receive increased ability to bind to the paint, while it simultaneously prohibits attack from fungus and rot to the surface treated.
  • the chitosan is used alone, it is firstly applied as a solution with low viscosity that is allowed to absorb into the wood as a primer and subsequently a high viscosity solution is applied as an outer coating.
  • Chitosan with high viscosity is dissolved in acid to which ammonium sulphite is added. Thereafter the solution is neutralized and the "jelly" dried. The resulting powder is mixed with the cement in an amount of 2.5 vol-%.
  • the chitosan fibers act as an extra bonding agent for the cement, while simultaneously protecting against fungus and algae.
  • the chitosan present also acts as a buffer against acidic influence on the concrete, thereby reducing the corrosive effect of acidic rain.
  • Materials like finished woodwork, textiles and marine constructions of tree as well as seine may be impregnated with a pure chitosan liquid or chitosan liquid with sulphites and thereafter given a secondary treatment with acetic anhydride (C 2 H 3 OO) 2 O, which leads to a conversion of the chitosan to the insoluble chitin.
  • the impregnated material is allowed to lay in acetic anhydride for three hours in a closed tank, and is thereafter washed clean of acetic anhydride. Examples
  • the examples comprises tests of some general properties of the preservative and some properties that are related to the interaction between the preservative and the substrate material that it is intended to protect. Solubility tests
  • Solubility tests were performed on chitosan dissolved in formic acid with ammonium sulphite as a stabilizer, on chitosan dissolved in formic acid with ammonium phosphite as stabilizer, chitosan dissolved in formic acid without stabilizer and chitosan dissolved in acetic acid without stabilizer.
  • a) Formic acid with stabilizer 10 1 water was added to 500g chitosan and stirred to form a suspension before the formic acid was added. The formic acid was added to an extent where all the chitosan was dissolved, and the resulting pH was 5.
  • Tests were also conducted on samples of the solution immobilized within porous materials (white cotton sheets ) with and without stabilizer.
  • the cotton sheets were immersed in the respective solution and dried.
  • the sheets were cut into pieces of approximately 10.0 g or
  • each sheet was exposed to one of the four solutions, 50 ml liquid for 1 day.
  • the sheets were wrung out but not rinsed after exposure.
  • Untreated seine is impregnated with a chitosan solution of a 100 cP viscosity.
  • 5% chitosan was first dissolved in formic acid and 0,5% ammonium sulphite was added as the salt. This yielded a solution with a pH of 5. Then the chitosan was impregnated into the substrate for
  • the substrate was allowed to dry until the chitosan solution had been fixed in the fibres.
  • the substrate was treated with a 12% ammonium sulphate solution to accelerate the process of curing the chitosan.
  • the chitosan solution was insolubly immobilized in the fibres.
  • Secondary treatment (impregnation) of the net may be performed by immersing / washing in chitosan solutions at certain intervals and according to the observed need for the relevant application/ use.
  • UV tests were performed in order to investigate whether chitosan treatment deteriorates or improves the seines' ability to resist aging inflicted by sunlight.
  • the samples was exposed for UV light in a weatherometer, using the following equipment and conditions:
  • Air temperature 40 +/- 5
  • C Air humidity (50 +/- 5)
  • % RH Radiation level 0.5 W/m 2 (between 290 and 800 nm)
  • Average radiation intensisty 550 W/m 2 (between 290 and 800nm)
  • Tests of accelerated growth were conducted with respect to weight increase of the seines. These tests were performed under controlled conditions where water movement, oxygen content and pH are not related to real-life situations. The tests still conveniently serve the purpose of direct comparison.
  • Pieces of seines of 100 cm 2 were weighed dry and suspended in a 1 1 beaker filled with contaminated seawater. One beaker was used for each piece of seine. The beakers were placed at room temperature with night and day light for 5 weeks without change of water, assumed to correspond to 4 months in the sea.. At the end of the test the pieces were weighed and photographed. The pieces were allowed to dry over night and were weighed again.
  • the test result shows that leakage is at an acceptably low level.
  • a chitosan solution in acetic acid and with ionic stabilizer was prepared the same way as with formic acid.
  • Wood bricks (surface pieces of pine) with dimensions 50x25x15 mm were climatized for four weeks. The bricks were weighed, the dimensions were measured and the year rings counted. They were dried in an oven for 18 hours at 103 +/- 2 °C, cooled in a desiccator and weighed. 16 bricks were impregnated in each batch with three different chitosan solutions (A, B and C). The bricks were put in a beaker and glass spheres were put on top to prevent the bricks from floating. The beaker was placed in a pressure tank and exposed to vacuum for 30 minutes. The preservative liquid solution was added and the tank pressurized for two hours. The bricks were wiped off and weighed again.
  • the wood material may be dried at once, or it may - in wet or dry condition - receive an additional treatment with a sulphite/ sulphate-only solution or with another stabilizer according to the invention.
  • a weak hydroxide solution may also be used in order to fix the chitosan rapidly to the wood structure.
  • an hydroxide solution is preferred for environmental reasons.
  • the wood may thereafter be treated in ordinary ways, e.g. with paint.
  • Wood material that is pressure impregnated with a chitosan solution according to the invention may also be covered with plastic substances like polyester or the like.
  • the chitosan will improve the binding between the polyester and the wood, which in turn makes it possible to use impregnated panel as panel for bathrooms or the like.
  • Example 3
  • the treatment may be done in one or in two steps, as the second treatment step may be one with a sulphite-only or a sulphate-only solution.

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  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical & Material Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Plant Pathology (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

La présente invention concerne une composition de protection contenant du chitosane ainsi qu'un premier anion pouvant être oxydé par l'air pour former un second anion, le complexe que ce dernier forme avec le chitosane étant moins soluble dans l'eau que le complexe formé par ledit premier anion et ledit chitosane. L'invention a également pour objet une composition de protection contenant du chitosane et ledit second anion, et un kit de composition de protection contenant ledit chitosane et ledit premier anion. Cette invention concerne également un procédé permettant la production de ladite composition de protection, ledit procédé comprenant les étapes suivantes: dissolution du chitosane dans un acide; éventuellement dépolymérisation du chitosane avec un agent oxydant; et mise en contact du chitosane avec ledit premier anion. L'invention a également pour objet différents procédés destinés au traitement de substrats avec la composition de protection, différentes utilisations de la composition de protection, et différents produits traités avec ladite composition de protection. Lesdits matériaux comprennent le bois, les toiles, par ex. les filets de pisciculture, des compositions de peinture et de ciment.
PCT/NO2002/000185 2001-06-18 2002-05-27 Composition de protection, et kit et procede permettant sa production et son utilisation WO2002102156A1 (fr)

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NO20013007 2001-06-18
NO20013007A NO20013007D0 (no) 2001-06-18 2001-06-18 Impregneringsmiddel og sett og fremgangsmåte for dets fremstilling og anvendelse

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020234643A1 (fr) * 2019-05-17 2020-11-26 Bona AB Système de revêtement à base de chitosane

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS61170376A (ja) * 1985-01-24 1986-08-01 Kazuji Fukunaga 食品の保存剤
JPH02258740A (ja) * 1989-03-31 1990-10-19 Taiyo Kagaku Kogyo Kk キトサンに安息香酸を吸着させる方法
JPH07227808A (ja) * 1994-02-22 1995-08-29 Toyo Mokuzai Boufu Kk 木材保存剤
JPH10165327A (ja) * 1996-12-12 1998-06-23 Toyo Kogyo Kk ウエットティッシュ
WO1999037584A1 (fr) * 1998-01-23 1999-07-29 Zodiac Pool Care, Inc. Compositions biocides pour le traitement de l'eau
JP2000053964A (ja) * 1998-08-05 2000-02-22 Tokyo Material Kk 植物用施用材
WO2001055220A1 (fr) * 2000-01-27 2001-08-02 Btg International Limited Produits chitosane de condensation, leur preparation et leurs utilisations

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JPS61170376A (ja) * 1985-01-24 1986-08-01 Kazuji Fukunaga 食品の保存剤
JPH02258740A (ja) * 1989-03-31 1990-10-19 Taiyo Kagaku Kogyo Kk キトサンに安息香酸を吸着させる方法
JPH07227808A (ja) * 1994-02-22 1995-08-29 Toyo Mokuzai Boufu Kk 木材保存剤
JPH10165327A (ja) * 1996-12-12 1998-06-23 Toyo Kogyo Kk ウエットティッシュ
WO1999037584A1 (fr) * 1998-01-23 1999-07-29 Zodiac Pool Care, Inc. Compositions biocides pour le traitement de l'eau
JP2000053964A (ja) * 1998-08-05 2000-02-22 Tokyo Material Kk 植物用施用材
WO2001055220A1 (fr) * 2000-01-27 2001-08-02 Btg International Limited Produits chitosane de condensation, leur preparation et leurs utilisations

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CHEN MAU-CHANG ET AL.: "Antimicrobial and physicochemical properties of methylcellulose and chitosan films containing a preservative", JOURNAL OF FOOD PROCESSING AND PRESERVATION, vol. 20, 1996, pages 379 - 390, XP002954689 *
DATABASE CAPLUS [online] FURUNO TAKESHI ET AL.: "Wood-mineral composites using colloidal silica solution system and their properties", XP002954692, accession no. STN Database accession no. 1997:287967 *
DATABASE WPI Week 198637, Derwent World Patents Index; Class D13, AN 1986-241855, XP002954691 *
DATABASE WPI Week 199835, Derwent World Patents Index; Class A96, AN 1998-406238, XP002954690 *
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PATENT ABSTRACTS OF JAPAN vol. 199, no. 511 26 December 1995 (1995-12-26) *
ZAIRYO, vol. 46, no. 4, 1997, pages 401 - 407 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020234643A1 (fr) * 2019-05-17 2020-11-26 Bona AB Système de revêtement à base de chitosane
CN114080430A (zh) * 2019-05-17 2022-02-22 博纳公司 基于壳聚糖的涂料体系

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