JP2007291287A - Compound for suppressing allergen - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a compound for suppressing allergen to enable to suppress allergen by a small amount of its without spoiling a feeling of living articles and a manufacturing method of it. <P>SOLUTION: The compound for suppressing allergen comprises a lignophenol derivative, namely a compound which phenol or a phenol derivative is added to lignin, therefore by supplying the compound for suppressing allergen to an object for allergen, allergen suppressing effect can be added to the object for allergen without spoiling the feeling under natural humidity in daily life. <P>COPYRIGHT: (C)2008,JPO&INPIT

Description

  The present invention relates to an allergen-inhibiting compound.

  In recent years, many allergic diseases such as atopic dermatitis, bronchial asthma and allergic rhinitis have become a problem. The main causes of this allergic disease are mites living in the house, especially leopard mite allergens (Der1, Der2), which are abundant in indoor dust, and cedar pollen floating in the air mainly in spring. This is because allergens such as allergens (Crij1, Crij2) are increasing in the living space.

  And, even if the leopard mite allergen is exterminated, the dead body of the leopard mite becomes an allergen, so it is not a fundamental solution for allergic diseases. Moreover, Crij1 which is a cedar pollen allergen is a glycoprotein having a molecular weight of about 40 kDa, and Crij2 is a glycoprotein having a molecular weight of about 37 kDa. When the cedar pollen allergen adheres to the nasal mucosa, the cedar pollen allergen is recognized as a foreign substance and causes an inflammatory reaction.

  Therefore, in order to reduce the symptoms of allergic diseases or prevent new allergic symptoms, it is necessary to completely inactivate allergens from the living space or to inactivate allergens.

  Allergens are proteins. Therefore, it is considered that the allergen loses allergenicity when it is denatured with heat, strong acid or strong alkali. However, allergens are very stable and are not easily denatured by oxidizing agents, reducing agents, heat, alkalis, and acids that can be used safely at home (Non-patent Document 1).

  If you try to denature the allergen, the daily necessities that are contaminated with allergens, such as tatami mats, carpets, floors, furniture (sofas, upholstered chairs, tables), bedding (beds, futons, sheets), in-car supplies (sheets, Child seats), kitchen supplies, baby items, curtains, wallpaper, towels, clothes, stuffed animals, other textile products, air purifiers (main body and filter) may be damaged depending on conditions.

  For this reason, a method of chemically modifying the molecular surface of the allergen under relatively mild conditions has been considered. For example, a method for suppressing allergens using tannic acid used for tanning of raw hides and the like (Patent Document 1), a method for suppressing allergens using tea extract or the like (Patent Document 2), hydroxy A method for suppressing allergens using a benzoic acid compound or a salt thereof (Patent Document 3) has been proposed, and an allergen suppressing effect has also been confirmed. However, since it is water-soluble, it is suitable for applications that require washing resistance. There was a problem that there was not.

  Further, Patent Document 4 proposes an allergen reducing agent composed of an aromatic hydroxy compound or the like, but the problem is that when the allergen reducing agent in an amount that exhibits a sufficient allergen suppressing effect is treated on fibers, the texture becomes worse. There was a point.

The Journal of Immunology Vol.144: 1353-1360 JP-A 61-44821 JP-A-6-279273 JP 11-292714 A JP 2003-81727 A

  The present invention provides an allergen-inhibiting compound that can suppress allergens in a small amount without impairing the texture of daily necessities.

  The allergen-inhibiting compound of the present invention is characterized by comprising a lignophenol derivative. This lignophenol derivative refers to a compound in which a phenol derivative is added to lignin. Chemical formula 1 shows a partial structural formula showing an example of a lignophenol derivative.

  As the lignin constituting the lignophenol derivative, lignin existing in any lignocellulosic material can be used. Examples of such lignocellulosic materials include woody parts of plants such as wood and processed products (for example, paper).

  When wood is used as the lignocellulosic material, the type of tree is not particularly limited, and may be a conifer or a broad-leaved tree. In addition, various herbaceous plants such as rice, corn, and sugarcane may be used as lignocellulosic materials. Furthermore, the lignocellulosic material may be a waste material or scrap of lignocellulosic material, or feed or agricultural waste.

  In addition, it does not specifically limit as a form of a lignocellulose type material, Although a powder form, a chip | tip form, etc. are mentioned, Since a lignophenol derivative can be extracted efficiently, a powder form is preferable.

  And it does not specifically limit as a phenol derivative added to lignin, For example, a monohydric phenol derivative, a bivalent phenol derivative, a trihydric phenol derivative etc. are mentioned, A phenolic hydroxyl group is concerned in allergen suppression ability. Therefore, divalent phenol derivatives and trivalent phenol derivatives having a large number of phenolic hydroxyl groups are preferable, and catechol, pyrogallol, derivatives containing a catechol structure, and derivatives containing a pyrogallol structure are more preferable.

  A monohydric phenol derivative refers to a compound having one phenolic hydroxyl group, one phenolic hydroxyl group, a compound having another substituent on the benzene ring, and a derivative containing the structure of these compounds. Specifically, Examples include phenol and cresol.

  The dihydric phenol derivative means a compound having two phenolic hydroxyl groups, two phenolic hydroxyl groups, a compound having other substituents on the benzene ring, and a derivative containing the structure of these compounds. Specifically, catechol, resorcinol, hydroquinone and the like can be mentioned.

  The trivalent phenol derivative refers to a compound having three phenolic hydroxyl groups, three phenolic hydroxyl groups, a compound having other substituents on the benzene ring, and a derivative containing the structure of these compounds. Specifically, phloroglucinol, hydroxyhydroquinone, pyrogallol and the like can be mentioned.

  Although it does not specifically limit as a number average molecular weight of a lignophenol derivative, From viewpoints, such as a physical property, 500 or more are preferable and 1000 or more are more preferable. Moreover, since the handleability of a lignophenol derivative may fall when the molecular weight of a lignophenol derivative is too large, 100,000 or less is preferable and 10,000 or less is more preferable.

  Next, a method for producing a lignophenol derivative will be described. As a method for producing a lignophenol derivative, a known production method can be used. For example, as disclosed in International Publication WO99 / 14223, a phenol derivative is added to lignin in a lignocellulosic material in the presence of a concentrated acid. And a reaction and addition method in a room temperature release system.

  As described above, when a phenol derivative is reacted with lignin in a lignocellulosic material in a room temperature release system in the presence of concentrated acid, the lignin in the lignocellulosic material is grafted with the phenol derivative and the basic skeleton of lignin is obtained. It is possible to obtain a lignophenol derivative in which a phenol derivative is introduced exclusively at the side chain α-position (benzyl position) of the phenylpropane unit. An example of a structural change when a phenol derivative is added to lignin is shown in Chemical Formula 2.

However, R _alpha, -OH, = O, or a -OR ^1, is R _beta, an alkyl group, an aryl group, or a -OR ^2. The R _alpha and R _beta, may differ even for the same. R ¹ is an alkyl group or an aryl group, and R ² is an aryl group.

  In general, lignocellulosic materials contain a large amount of components other than lignin typified by carbohydrates, and products obtained by treating lignocellulosic materials with phenol derivatives include products other than lignophenol derivatives. Contains a large amount of compound.

  However, the product obtained by treating lignocellulosic material with a phenol derivative can be easily separated into a hydrophilic phase and a hydrophobic phase due to the difference in specific gravity and the dispersibility in water. It can be obtained in a state containing a small amount of other compounds, and a lignophenol derivative with high purity can be easily obtained by removing impurities.

  Next, a specific method for producing a lignophenol derivative will be described. As a first specific production method, as described in International Publication No. WO99 / 14223, a lignocellulosic material is treated with a phenol derivative, concentrated acid is added to separate the upper and lower layers, and the upper layer (Organic layer) includes a method for obtaining a phenol derivative.

  In such a case, as described in FIG. 4 of International Publication No. WO99 / 14223, an upper layer (organic layer) of two layers obtained by adding concentrated acid is separated as necessary. ) And an excess amount of diethyl ether is added to separate the dissolved and insoluble sections. Lignophenol purified by adding acetone to the insoluble fraction obtained and separating it into a soluble and insoluble fraction, adding an excess amount of diethyl ether to the soluble fraction and separating it into a soluble and insoluble fraction. Derivatives can be obtained.

  More specifically, after the liquid phenol derivative is infiltrated into the lignocellulosic material such as wood flour, the lignin contained in the lignocellulosic material is solvated with the phenol derivative, and then the lignocellulosic material is used. For example, a concentrated acid such as 72% by weight sulfuric acid is added and mixed to dissolve the cellulose component.

  According to this method, a phenol derivative obtained by solvating lignin and a concentrated acid dissolving a cellulose component form a two-phase separation system. The lignin solvated by the phenol derivative is in contact with the acid only at the interface where the phenol derivative phase is in contact with the concentrated acid phase, and the side chain α-position, which is a highly reactive site of the basic lignin unit formed by contact with the acid. The cation at the (benzylic position) will be attacked simultaneously by the phenol derivative. As a result, the phenol derivative is introduced into the α-position by a C—C bond, and the benzyl aryl ether bond is cleaved to lower the molecular weight, so that the lignin is reduced in molecular weight and the basic structural unit of the lignin. A lignophenol derivative having a phenol derivative introduced at the benzyl position is produced in the phenol derivative phase. And a lignophenol derivative can be extracted from this phenol derivative phase. This lignophenol derivative is obtained as a part of an assembly of low molecular weight forms of lignin in which the benzyl aryl ether bond in lignin is cleaved to reduce the molecular weight. In addition, although the abundance ratio of the phenol derivative introduced into the benzyl position is low, it is known that some are introduced via the phenolic hydroxyl group.

  Extraction of the lignophenol derivative from the phenol derivative phase can be performed, for example, by the following method. That is, the precipitate section obtained by adding the phenol derivative phase to a large excess of diethyl ether is collected and dissolved in acetone, the acetone-insoluble section is removed by centrifugation, and the acetone-soluble section is concentrated. This acetone soluble section is dropped into a large excess of diethyl ether to collect the precipitated section. After removing the solvent from this precipitation section, the lignophenol derivative can be obtained by drying under reduced pressure in a desiccator containing diphosphorus pentoxide. The crude lignophenol derivative can also be obtained by simply removing the phenol derivative phase by vacuum distillation. In addition, acetone soluble classification can also be used for a secondary derivatization process as a lignophenol derivative solution as it is.

  Furthermore, as a second specific manufacturing method, as shown in FIG. 5 of International Publication WO99 / 14223, a solution obtained by dissolving a phenol derivative in a lignocellulosic material in a solvent such as ethanol or acetone. Then, the solvent is removed (phenol derivative sorption step).

  Next, a concentrated acid is added to the lignocellulosic material to dissolve the cellulose component. As a result, as in the first method, the lignin in the state solvated with the phenol derivative is attacked by the phenol derivative at the high reaction site (side chain α-position) of the lignin generated by contact with concentrated acid. Thus, a phenol derivative is introduced into lignin. In addition, the benzyl aryl ether bond is cleaved to reduce the lignin molecular weight. The characteristics of the obtained lignophenol derivative are the same as those obtained by the first method. Then, the lignophenol derivative is extracted with a liquid phenol derivative. Extraction of the lignophenol derivative from the liquid phenol derivative phase can also be performed in the same manner as in the first method. Alternatively, the entire reaction solution after the concentrated acid treatment is poured into an excessive amount of water, and the insoluble fraction is collected by centrifugation, dialyzed and dried. The lignophenol derivative can be extracted by adding acetone or alcohol to the dried product. Furthermore, the soluble segment may be dropped into excess diethyl ether or the like in the same manner as in the first method to obtain a lignophenol derivative as an insoluble segment. In this method, similarly, the acetone-soluble segment can be used as a lignophenol derivative solution for the secondary derivatization treatment.

  Of these two methods, the second method is preferred, and the latter, ie, the method of extracting and separating the lignophenol derivative with acetone or alcohol is economical because the amount of the phenol derivative used is small. And more preferable. And since this method can process a large amount of lignocellulosic materials with a small amount of phenol derivatives, it is suitable for large-scale synthesis of lignophenol derivatives.

  Further, as described in JP-A No. 2003-268116, a third specific production method may be performed by adding a phenol derivative to lignin and then adding an acid, and then adding excess water. This is a method in which a lignophenol derivative is obtained by separating into a soluble section and an insoluble section, drying the insoluble section, adding an antioxidant and an aqueous alkali solution, and then performing solid-liquid separation (for example, centrifugation).

  In the present invention, lignophenol derivatives obtained using any of the production methods described above can also be suitably used.

  Furthermore, it is preferable to add a hydrophilic polymer to the allergen-inhibiting compound. As such a hydrophilic polymer, those capable of forming a reaction field capable of causing interaction with the allergen-inhibiting compound by collecting water molecules in the air are preferable.

Then, by adding a hydrophilic polymer to the allergen-inhibiting compound, the allergen-inhibiting compound can more effectively suppress allergens under normal humidity conditions, for example, in an atmosphere having an absolute humidity of 50 g / m ³ or less. Can do.

  The “reaction field that can interact with allergen-inhibiting compounds by collecting water molecules in the air” refers to any chemical in order to suppress the antigenicity of the part (epitope) where the allergen exhibits antigenicity. It is a reaction field for interacting, for example, by stabilizing the electrochemical transition state such as the ionized state and lowering the barrier energy of the transition state of the chemical reaction, the natural chemical reaction proceeds. This is a reaction field.

  In general, liquid state water is required to lower the transition state energy barrier that must be exceeded in order to cause a chemical reaction, but the allergen-inhibiting compound of the present invention is designed to increase humidity. The above-mentioned reaction field can be formed by collecting moisture in the air without any operation, and moreover, the above-mentioned reaction field can be made more reliable by adding a hydrophilic polymer as described above. Can be formed.

  The hydrophilic polymer is not particularly limited, for example, a polymer having an ether bond and / or an amide bond in the main chain, a polymer having a polar group in the side chain, an ether bond and / or in the main chain. Examples thereof include a polymer having an amide bond and a polar group in the side chain. Examples of the polar group include primary amines such as primary amines, secondary amines, and tertiary amines, cationic groups such as ammonium bases; hydrocarbon oxycarbonyl groups such as sulfuric acid esters and phosphoric acid esters, and carboxyl groups. And anionic groups such as sulfone groups and nonionic groups such as hydroxy groups and amide groups.

  Specific examples of the hydrophilic polymer include starch, cellulose, tannin, ignin, natural compounds such as polysaccharides such as alginic acid and gum arabic, polyalcohols such as polyvinyl alcohol and butyral, polyoxymethylene, and polyoxyethylene. , Polyethers such as polyoxypropylene, polymer acids such as polyacrylic acid, polymer salts such as sodium polyacrylate, polyamines such as polyallylamine, synthetic compounds such as polyacrylamide, polyvinylpyrrolidone, polyurethane, and acrylic resins Synthetic polymers are preferred in that they do not show deliquescence under normal indoor conditions, and are not only hygroscopic but also highly water-retaining, so polyvinyl alcohol, polyoxyethylene, polyacrylic acid, sodium polyacrylate , Polyacrylamide, polyvinyl pyrrolidone are preferred. In addition, although a hydrophilic polymer may be individual or may use 2 or more types together, it is preferable to combine 2 or more types of hydrophilic polymers which have a different molecular structure.

  As a combination of two or more kinds of hydrophilic polymers having different molecular structures, a combination of a polyether and a polymer salt, a combination of a polyether and a polyalcohol is preferable, a combination of polyoxyethylene and sodium polyacrylate, A combination of polyoxyethylene and polyvinyl alcohol is more preferred.

  If the melting point of the hydrophilic polymer is low, it may become liquid in the use atmosphere of the allergen-inhibiting compound, and there is a risk that the daily goods treated with the allergen-inhibiting compound may become sticky, etc. 40 degreeC or more is preferable, and when an allergen suppression compound is used in the atmosphere with many opportunities to contact with water, in order to maintain the inhibitory effect of allergen, 50 degreeC or more is more preferable.

  If the content of the hydrophilic polymer is small, water molecules in the air cannot be collected sufficiently, so that a reaction field sufficient to cause interaction with the allergen cannot be formed. While the inhibitory compound may not be able to exert a sufficient allergen inhibitory effect, if it is large, the amount of the allergen inhibitory compound will be relatively small, and the allergen inhibitory effect of the allergen inhibitory compound may be reduced. Therefore, 40 to 1000 parts by weight is preferable and 50 to 1000 parts by weight is more preferable with respect to 100 parts by weight of the allergen-inhibiting compound.

  In addition, by increasing the molecular weight of the allergen-inhibiting compound using an epoxy resin or the like, the solubility of the allergen-inhibiting compound in a solvent such as water is reduced to improve the solvent resistance, and the allergen-inhibiting compound has an allergen-inhibiting effect. It can be sustained for a long time. For example, even when water is applied or washed on daily goods treated with an allergen-inhibiting compound, the allergen-inhibiting compound can be prevented from dissolving and disappearing in water, and the allergen-inhibiting compound can suppress allergens. Can be maintained for a long period of time.

  The allergen-inhibiting compound of the present invention may contain formulation adjuvants such as a dispersant, an emulsifier, an antioxidant, and an ultraviolet absorber as long as the effectiveness of the allergen-inhibiting effect is not impaired. Mites, bactericides, fungicides, deodorants and the like may be contained.

  Next, how to use the allergen-inhibiting compound will be described. For the allergen-inhibiting compound, general-purpose usage methods such as a spray type, an aerosol type, a smoke type, and a heat transpiration type can be used. The allergen-inhibiting compound is dissolved or dispersed in a solvent to form an allergen-inhibiting compound solution, and the allergen-inhibiting compound solution is mixed with an aqueous solvent, oil agent, emulsion, suspension, etc., thereby making the allergen-inhibiting compound a spray type. Can do. In addition, a spray type means the usage method which applies a pressure to the allergen suppression compound solution under normal pressure, and sprays the allergen suppression compound in the shape of a mist.

  Examples of the solvent include water (preferably ion-exchanged water), alcohols (methyl alcohol, ethyl alcohol, propyl alcohol, etc.), hydrocarbons (toluene, xylene, methylnaphthalene, kerosene, cyclohexane, etc.), Ethers (diethyl ether, tetrahydrofuran, dioxane etc.), ketones (acetone, methyl ethyl ketone etc.), amides (N, N-dimethylformamide etc.) are mentioned.

  Then, by adding a solid carrier (talc, bentonite, clay, kaolin, diatomaceous earth, silica, vermulite, perlite, etc.) to the spray-type allergen-inhibiting compound, the allergen-inhibiting compound can be made into an aerosol type. .

  Here, the aerosol type means that the allergen-inhibiting compound solution is sealed in a container in a state where the propellant is compressed together with the propellant, and the allergen-inhibiting compound is sprayed in a mist state by the pressure of the propellant. Say. Examples of the propellant include nitrogen, carbon dioxide, dimethyl ether, and LPG.

  The spray-type allergen-inhibiting compound is added to an oxygen supply agent (potassium perchlorate, potassium nitrate, potassium chlorate, etc.), a combustion agent (sugar, starch, etc.), and a heat generation regulator (guanidine nitrate, nitroguanidine, guanyl phosphate). The allergen-inhibiting compound can be made into a smoke type by adding an auxiliary agent for decomposing oxygen supply agent (potassium chloride, copper oxide, chromium oxide, iron oxide, activated carbon, etc.). The smoke type refers to a method of use in which an allergen-inhibiting compound is finely divided into smoke and dispersed.

  Then, the allergen-inhibiting compound is sprayed on an object in which allergen is present, such as a daily necessities, that is, an object for which allergen is to be suppressed (hereinafter referred to as “allergen object”), according to various methods of use. Allergens can be suppressed by dispersing, applying or fixing and supplying. In addition, the said allergen suppression compound may be used independently, or 2 or more types may be used together.

  In addition, “suppressing allergens” means allergens of leopard mite (Der1, Der2), cedar pollen allergens floating in the air (Crij1, Crij2), allergens caused by dogs and cats (Can f1, Fel d1), etc. This refers to denaturing or adsorbing allergens and suppressing the reactivity of allergens to specific antibodies.

  In addition, examples of the allergen object include daily items that serve as a hotbed for allergens in a living space. Examples of the daily necessities include tatami mats, carpets, floors, furniture (sofas, upholstered chairs, tables), bedding (beds, futons, sheets), in-car items (seats, child seats), kitchen items, baby items, curtains, Examples include wallpaper, towels, clothes, plush toys, textiles, and air purifiers (main body and filters). Furthermore, in addition to the above, the allergen-inhibiting compound can also exert an allergen-inhibiting effect by being added to a detergent, a softening finish or the like.

  The amount of the allergen-inhibiting compound of the present invention to be used for the allergen target is small, the allergen-inhibiting effect of the allergen-inhibiting compound may not be manifested. The amount is preferably 0.1 to 300 parts by weight, more preferably 0.2 to 100 parts by weight, and particularly preferably 0.5 to 50 parts by weight with respect to 100 parts by weight.

  Examples of allergens targeted by the allergen-inhibiting compound of the present invention include animal allergens and plant allergens such as pollen. Particularly effective animal allergens include mite allergens (mites, arthropod ginsengs-mite organisms, which are mainly divided into seven subtypes. , Anterospira represented by ticks, mite, posterior genus represented by spider mite, middle antrum represented by house dust mite, spider mite, anterior genus represented by staghorn tick, nymph mite, leopard mites such as mite It can be a target for any type of anatomical gates such as Kenagakonadani, Jesa Saladani, and Hidden Gates represented by Kasari Mite, but it is often found in indoor dust, especially bedding, and causes allergic diseases. Is particularly effective.

  According to the use point of the above-mentioned allergen suppression compound, the reactivity with respect to the specific antibody of the allergen which exists in an allergen target object was suppressed by supplying an allergen suppression compound to an allergen target object as needed.

  The allergen-inhibiting compound may be contained in a fiber to form an allergen-inhibiting fiber, and the allergen-inhibiting effect may be imparted to the fiber itself. By producing the above-mentioned daily necessities using this allergen-suppressing fiber, the allergen-inhibiting effect can be imparted to the daily necessities in advance.

  Examples of the method for containing the allergen-inhibiting compound in the fiber include a method in which the allergen-inhibiting compound is physically fixed to the fiber. The fiber is not particularly limited as long as it can contain an allergen-inhibiting compound. For example, a synthetic fiber such as a polyester fiber, a nylon fiber, an acrylic fiber, or a polyolefin fiber, or a half of an acetate fiber or the like. Examples thereof include synthetic fibers, recycled fibers such as cupra and rayon, natural fibers such as cotton, hemp, wool, and silk, or composite fibers and mixed cottons of these various fibers.

  A method for physically fixing the allergen-inhibiting compound to the fiber will be described. Examples of the method for physically fixing the allergen-inhibiting compound to the fiber include, for example, (1) dissolving or dispersing the allergen-inhibiting compound in a solvent, impregnating the fiber in this allergen-inhibiting compound solution, A method of impregnating the solution, (2) a method of applying the allergen-inhibiting compound solution to the fiber surface, and (3) immersing the allergen-inhibiting compound in a binder obtained by dissolving or dispersing the allergen-inhibiting compound, (4) A method in which a binder obtained by dissolving or dispersing the allergen-inhibiting compound is applied to the fiber surface, and the allergen-inhibiting compound is adhered to the fiber with the binder. In the above methods (1) and (2), the allergen-inhibiting compound solution may contain the following binder.

  The solvent is not particularly limited. For example, water; alcohols such as methyl alcohol, ethyl alcohol, and propyl alcohol; hydrocarbons such as toluene, xylene, methylnaphthalene, kerosene, and cyclohexane; diethyl ether, tetrahydrofuran, dioxane, and the like Ethers; ketones such as acetone and methyl ethyl ketone; amides such as N, N-dimethylformamide and the like.

  The binder is not particularly limited as long as it can fix the allergen-inhibiting compound to the fiber surface. For example, the binder made of a synthetic resin may be a urethane resin such as a one-component urethane resin or a two-component urethane resin. Acrylic resin, urethane acrylate resin, polyester resin, unsaturated polyester resin, alkyd resin, vinyl acetate resin, vinyl chloride resin, epoxy resin, epoxy acrylate resin, and the like, and urethane resin is preferable.

  Since the allergen-inhibiting compound of the present invention has the above-mentioned configuration, supplying the allergen-inhibiting compound to the allergen object damages the texture of the allergen object under normal humidity in daily life. And allergen-suppressing effect can be imparted.

  The number average molecular weight (Mn) of the allergen-inhibiting compound was calculated as a polystyrene equivalent value by gel permeation chromatography. Note that an N, N-dimethylformamide solvent containing 0.4% by weight of lithium chloride was used as an eluent (developing solution).

Example 1
Preparation of lignocresol 1 g of softwood (cypress, scientific name: Chamaecyparis Obtusa) is infiltrated with 5 g of heated p-cresol and infiltrated. After the addition, the mixture was stirred at room temperature and then separated into two upper and lower layers by centrifugation. Excess diethyl ether was added to the upper layer (cresol layer) to separate into dissolved and insoluble sections. The insoluble fraction was supplied to 100 ml of acetone, and the extract was concentrated and then dropped again in an excess amount of diethyl ether to obtain 0.2 g of lignocresol as an allergen-inhibiting compound.

(Example 2)
Preparation of lignocatechol 3 mol of catechol was dissolved in 1 liter of acetone per basic unit of lignin (phenylpropane unit, C ₉ ) contained in 500 g of cypress (Chamaecyparis Obtusa) defatted wood flour. After dipping cypress defatted wood flour in this acetone solution for 24 hours, acetone was completely air-dried and removed to sorb catechol onto wood flour to obtain 650 g of sorbed wood flour.

  Phosphoric acid with a concentration of 95% by weight (20 ml / g sorption wood flour) was added to the sorption wood flour, and the phosphoric acid was stirred at 50 ° C. for 1 hour. In addition, it adjusted so that phosphoric acid might be 20 ml per 1g of sorption wood flour.

  Thereafter, the phosphoric acid was supplied and dispersed in an excessive amount of water with vigorous stirring. The insoluble fraction was precipitated and the supernatant was exchanged to remove the acid, then the precipitate was dried and extracted with 7 liters of acetone. The obtained acetone solution was concentrated, and this acetone solution was put into a mixed solution obtained by mixing benzene and hexane so that the volume ratio (benzene / hexane) was 2, thereby obtaining an insoluble section. The above insoluble fraction was washed several times until no lignocatechol soluble in the organic phase and unreacted catechol were extracted with the above mixed solution, and finally washed with diethyl ether to give 100 g of lignocatechol as a precipitate. Obtained as an inhibitory compound.

(Example 3)
Preparation of lignopyrogallol Lignopyrogallol was obtained as an allergen-inhibiting compound by performing the same operation as in Example 2 except that pyrogallol was used instead of catechol.

(Comparative Example 1)
Poly 4-vinylphenol (Aldrich weight average molecular weight: 8000) was used as the allergen-inhibiting compound.

  The allergen inhibitory ability of the obtained allergen inhibitory compound was measured in the following manner, and the number average molecular weight (Mn) of the allergen inhibitory compound was measured in the above manner. The results are shown in Table 1.

(Allergen suppression ability)
An allergen solution was prepared by dissolving a cold-dried powder of allergen (trade name “Mite Extract-Df” manufactured by Cosmo Bio) in a phosphate buffer (pH 7.6) so that the amount of protein was 10 ng / ml.

  Next, the allergen inhibitor compound was dissolved in dimethylformamide to prepare an allergen inhibitor compound solution in which the concentration of the allergen inhibitor compound was 1% by weight, 0.1% by weight, or 0.01% by weight.

  Then, 1 ml of the allergen solution is supplied into the test tube, and while stirring the test tube using a test tube mixer, 100 microliters of the allergen-inhibiting compound solution is added to the allergen solution in the test tube. Shake for 2 hours at 37 ° C.

  Subsequently, 100 microliters of the processing solution in the test tube was collected, and the allergenicity of this processing solution was measured using an allergen measuring tool (trade name “Mighty Checker” manufactured by Shinto Fine Co., Ltd.) and evaluated based on the following criteria. . Note that the darker the color, the more allergen is present in the treatment solution, and the allergen-inhibiting compound does not exhibit the allergen-inhibiting effect.

4 ... Dark, thick, clear lines observed (no allergen suppression effect)
3 clearly shows that it is a line (there is a slight allergen suppression effect)
2 ... It can be seen that the color is faintly colored (with allergen suppression effect)
1 ... no color development (allergen suppressive effect is sufficient)

Claims (3)

An allergen-inhibiting compound comprising a lignophenol derivative. The allergen-inhibiting compound according to claim 1, wherein the lignophenol derivative is a compound obtained by adding a phenol derivative to lignin. The allergen-inhibiting compound according to claim 2, wherein the phenol derivative is catechol or pyrogallol.