WO2006120851A1 - Agent for imparting functions to textile products - Google Patents

Abstract

It is intended to provide an agent for imparting functions by which functions (for example, humidification, retardation of skin aging, improving skin properties, prevention of bedsore, therapeutic effect, prevention and amelioration of atopic dermatitis, antiinflammatory effect, wound-healing, etc.) can be imparted to textile products. Namely, an agent for imparting functions to textile products which contains hydroxyproline, an acylated derivative of hydroxyproline or a salt thereof; and functional textile products with the use of the agent for imparting functions as described above, in particular, architectural and bed-clothing materials and goods, interior materials and goods, automotive interior materials and goods, nursing care materials and goods, clothes, cloth diapers, paper diapers, wet tissues and tissue papers.

Description

 Specification

 Functionality-imparting agent for textile products

 Technical field

 [0001] The present invention relates to a functional imparting agent for a fiber product, a functional fiber product, and a method for producing the functional fiber product, which contains hydroxyproline or an N-acylated derivative of hydroxyproline or a salt thereof.

 Background art

 [0002] Hydroxyproline, an N-acylated derivative of hydroxyproline, or a salt thereof is known as an amino acid exhibiting a moisturizing effect, and has skin-beautifying effects such as skin aging suppression and skin quality improvement as a cosmetic ( For example, patent document 1), prevention of pressure ulcer, and therapeutic effects (for example, patent document 2), prevention and improvement of atopic dermatitis (for example, patent document 3), anti-inflammatory, wound healing effect (For example, Non-Patent Document 1) is known.

 [0003] Further, Patent Document 4 discloses an agent for imparting functionality to a fiber product containing amino acids, and Patent Document 5 discloses a fiber web. As the amino acids, hydroxyproline or hydroxy is disclosed. There is no specific description of N-acyl yl derivatives of proline or salts thereof. Patent Document 1: International Publication No. OOZ51561 Pamphlet

 Patent Document 2: Pamphlet of International Publication No. 2004Z28531

 Patent Document 3: International Publication No. 02Z6225 Pamphlet

 Patent Document 4: Japanese Patent Application Laid-Open No. 2004-324026

 Patent Document 5: International Publication No. 96Z31644 Pamphlet

 Non-Patent Document 1: Eurobian Medical Research 3rd, 182-188, 1998 Invention Disclosure

 Problems to be solved by the invention

[0004] The present invention relates to an excellent function of hydroxyproline or an N-acylated derivative of hydroxyproline or a salt thereof for a fiber base material widely used for clothes, bedding, paper omgu, etc. An attempt was made to impart the excellent properties of the wood while keeping it intact, providing superior functional fiber products without drastically changing the conventional fiber manufacturing process and properties. The task is to do.

 Means for solving the problem

 [0005] The gist of the present invention is as follows.

 [0006] (1) An agent for imparting functionality to a textile product, containing hydroxyproline or an N-acylated derivative of hydroxyproline or a salt thereof.

[0007] (2) The function according to item 1 above, wherein the N-acylated derivative of hydroxyproline is an N-acetylated derivative, an N-propionylated derivative, an N-propylylated derivative or an N-isoptyrylated derivative. Sex imparting agent.

[0008] (3) The functional agent according to the above item 1 or 2, which is microencapsulated, encapsulated with a cyclodextrin, or a vesicle structure.

[0009] (4) The functionality-imparting agent according to any one of Items 1 to 3, which contains a binder.

[0010] (5) A method for producing a functional fiber product, wherein the fiber product is treated with the functionality-imparting agent according to any one of Items 1 to 4.

[6] (6) Construction / bedding materials and products, interior materials and products, automobile interior materials and products, and caring materials and materials to which hydroxyproline or an N-acylated derivative of hydroxyproline or a salt thereof is bound Product.

[0012] (7) N-acylated derivative power of hydroxyproline N-acetylated derivative, N-propionylated derivative, N-propylylated derivative or N-isoptyrylated derivative according to item 6 above · Bedding materials and products, interior materials and products, automotive interior materials and products, and nursing materials and products.

[0013] (8) A garment to which hydroxyproline or an N-acylated derivative of hydroxyproline or a salt thereof is bound.

 [9] The garment according to [8], wherein the N-acylated derivative of hydroxyproline is an N-acetylated derivative, an N-propionylated derivative, an N-propylylated derivative or an N-isoptyrylated derivative. .

 [0015] (10) Cloth, paper, wet tissue and tissue paper to which hydroxyproline or an N-acylated derivative of hydroxyproline or a salt thereof is bound.

[11] (11) N-acylated derivative power of hydroxyproline N-acetylated derivative, N-pro 11. The cloth, paper, wet tissue and tissue paper according to item 10 above, which is a pionilouich derivative, an N-butyrrhich derivative or an N-isobutyrych derivative. The invention's effect

 [0017] According to the present invention, the fiber product has functions such as moisture retention, skin aging prevention, skin quality improvement and other skin beautifying effects, pressure ulcer prevention, anti-atopic, anti-inflammatory and wound healing effects. It can be granted.

 BEST MODE FOR CARRYING OUT THE INVENTION

[0018] The hydroxyproline used in the present invention may be any stereoisomer of hydroxyproline. In other words, proline of hydroxyproline has 8 physical isomers depending on whether it is D-strength L-strength or hydroxyl-position 3 or 4-position, and its stereoisomer is cis-force trans. And deviations of mixtures thereof can also be used in the present invention.

 [0019] Specific examples of hydroxyproline include cis-4-hydroxy-1-L-proline, cis-1-hydroxy-D-proline, cis-3-hydroxy-L-proline, cis-3-hydroxy-D-proline, trans-4-hydroxy-L-- Examples include proline, trans-4-hydroxy-D-proline, trans-1-hydroxy-L-proline, and trans-3-hydroxy-D phosphorus.

 [0020] Hydroxyproline is a kind of amino acid that exists widely in nature as a major constituent amino acid component in collagen and as a constituent amino acid of elastin. For example, hydroxyproline acid-hydrolyzes collagen derived from animals such as butterfly. It can be produced by purification by a conventional method.

 [0021] Trans-4-hydroxy L-proline is a proline 4-hydroxylase isolated from microorganisms of the genus Amvcolatopsis or Dactvlosporangium (JP-A-7-313179). Can be used. In addition, cis-3 hydroxyl L proline can be produced using porphyrin 3-position hydroxylase (Japanese Patent Laid-Open No. 7-322885) isolated from Streptomyces genus cattle. Yes, Bioindustry 1, 14 卷, 31 (1997).

[0022] Hydroxyproline produced using the above-mentioned microorganism-derived enzyme has excellent quality. It is more preferable as hydroxyproline used in the present invention.

 [0023] Examples of the N-acyl yl derivatives of hydroxyproline used in the present invention include the above-mentioned N-acyl yl derivatives of the various hydroxyproline stereoisomers. Examples of the acyl group of the N-acyl derivative include preferably an acyl group having 1 to 24 carbon atoms, more preferably 1 to 12 carbon atoms, and particularly preferably 1 to 6 carbon atoms. Honoleminole, acetinole, propionyl, butyrinole, isobutyryl, norellinore, pivalol, hexanol, heptanol, otatanyl, nonanoyl, decanol, undecanol, dodecanol, etc.

 [0024] Examples of the salt of hydroxyproline or N-acylated derivative of hydroxyproline include alkali metal salts such as sodium, potassium and lithium, alkaline earth metal salts such as calcium and magnesium, ammonium salts, Examples thereof include addition salts of amines such as monoethanolamine, diethanolamine, triethanolamine and triisopropanolamine, and addition salts of basic amino acids such as arginine and lysine.

 [0025] The N-acyl derivative of hydroxyproline can be prepared by a known method. For example, N-acyl derivatives of hydroxyproline are linear or branched saturated fatty acids having 1 to 24 carbon atoms, such as chlorides and bromides using halogenating agents such as salt and phosgene. The product can be produced by conversion to a halogenated product such as the above, followed by condensation with hydroxyproline as described above, or conversion of a fatty acid to an acid anhydride followed by reaction with hydroxyproline.

 [0026] Examples of fatty acids include formic acid, acetic acid, propionic acid, butyric acid, isobutyric acid, valeric acid, isovaleric acid, pivalic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, and undehydroacid. A fatty acid such as dodecanoic acid is used alone or in combination.

 [0027] A method for producing an N-acylated derivative of hydroxyproline via an acid halide is exemplified below.

[0028] The fatty acid is dispersed in a solvent such as methylene chloride, chloroform, carbon tetrachloride, benzene, toluene, xylene, n-hexane, etc., and 1 to 5 times equivalent of a halogenating agent is added thereto to react. To obtain a fatty acid noride. Next, hydroxyproline is dissolved or dispersed in a solvent, While maintaining the obtained solution at 5 to 70 ° C., 0.3 to 3.0 times equivalent of the above fatty acid halide to hydroxyproline was added, and an acylation reaction was carried out, whereby an N-acylyde derivative of hydroxyproline. Can be manufactured.

 [0029] Examples of the solvent used in the acyl chloride reaction include water, methanol, ethanol, isopropanol, isobutanol, acetone, toluene, tetrahydrofuran, ethyl acetate, N, N dimethylformamide, dimethyl sulfoxide, and the like. May be used alone or in combination. When hydroxyproline is dissolved or dispersed in a solvent, 0.8 to 2.0 times equivalent of alkaline substance such as sodium hydroxide and potassium hydroxide is dissolved in the solvent as necessary. Alternatively, it may be dispersed.

 [0030] When it is desired to obtain a salt of an N-acylated derivative of hydroxyproline, if the N-acylated derivative of hydroxyproline is obtained in the form of a salt, it can be purified as it is and obtained in a free form. May be dissolved or suspended in a suitable solvent and a base may be added to form a salt.

 [0031] For purification, for example, usual methods such as crystallizing and chromatography are used.

[0032] Specific N-acylated derivatives of hydroxyproline include, for example, N-acetyl-cis-4-hydroxy-1-L-proline, N-acetylenolysis-1-4-hydroxy-1-D-proline, N- 1-hydroxyl L-proline, N-acetylenic 1-hydroxy D-proline, N-acetylenic trans 4-4-hydroxy L-proline, N-acetylin trans 4-hydroxy D-proline, N-acetylinole trans 3-hydroxyl-proline, N-acetylinole -Trans 3-hydroxy D proline, N-propionyl-cis 4-hydroxy-L-proline, N-propionyl-cis-4-hydroxy-D-proline, N-propionyl-cis 3-hydroxy L proline, N propionyl cis 3 —Hydroxy D—proline, N propionyl trans 4-hydroxy L— Proline, N-propioninoletrans 4-hydroxy D pulin, N-propioninole trans 3-hydroxy L-proline, N-propioninole trans 3-hydroxy D-proline, N butyrinolesis 4-hydroxy L proline, N butyryl cis-4-hydroxy-D-proline, N butyryl lucose 3-hydroxy L-proline, N butyryl cis 3-hydroxy D-proline, N— Butyrinore trans 4 Hydroxy L—proline, N Butyrinore trans 4—Hydroxy D—Proline, N Butyryl ro trans 3—Hydroxy L—Proline, N Butylyl 1 trans 1—Hydroxy 1 D Proline, N—Isobutyryl 1 cis 1 4 —Hydroxy L-proline, N-isobutyryl cis-4-hydroxy D-proline, N-isobutyryl cis 1 3-hydroxy L proline, N isobutyryl cis 1 3-hydroxy —D-proline, N-isobutyrino Rhettrans-4-hydroxy L-proline, N-isobutyryl 1-trans 4-hydroxy D proline, N-isobutyryl 1-trans 1-hydroxy 1-L proline, N-isobutyryl 1-trans 1 3-hydroxy 1-D proline, etc. be able to.

 [0033] The function-imparting agent of the present invention preferably contains 0.01 to 30% by weight of hydroxyproline, a hydroxyproline N-acylated derivative or a salt thereof.

 [0034] The functionality-imparting agent of the present invention includes, for example, a stabilizer such as hydroxyproline or a N-calyzed derivative of hydroxyproline or a salt thereof of 0.01 to 30 parts by weight, necessary sorbitol or sorbitol. 0.1 to 10 parts by weight, for example, antiseptic of isothiazoline-based antibacterial agents such as 5-clonal 2-methyl-4-isothiazolin-1-one and 2-methyl-4-isothiazolin-1-one compound (trade name: caisson) Preparation is made with 0.05 to 0. 3 parts by weight of the agent, 0.5 to 25 parts by weight of the binder, and 100 parts by weight of water.

 [0035] The functionality-imparting agent of the present invention further includes peptides, hydroxyproline or amino acid derivatives other than salts of hydroxyproline or its salts, vitamins, ceramides, glycyrrhizic acids of licorice extract, and raspberries. Extract, lavender extract, jasmine extract, peno mint extract, rosemary extract, roman force fir mono extract, eucalyptus extract, hinokitiol, bamboo extract, aloe extract, catechin, grape funoles extract, lemon extract, jojoba oil, olive oil Citrus oil, seaweed extract, squalene, collagen, and at least one selected from the group power that also has glucose strength may be combined.

[0036] Examples of the peptide include silk protein, hive mouth-in, and the like, and examples of the amino acids include glutamic acid, aspartic acid, glycine, cystine, serine, histidine, lysine, arginine, leucine and the like. It is not limited to. As the vitamins, vitamin A, vitamin C, vitamin E, etc. can be used effectively. Examples of the glycyrrhizic acid of Kiss include glycyrrhizic acid, glycyrrhetinic acid, sodium glycyrrhizinate, potassium glycyrrhizinate, and ammonium glycyrrhizinate. Furthermore, examples of the raspberries include raspberries and raspberry ketones, examples of the squalans include squalans and squalene, and examples of the glucose include glucose, xylitol, and erythritol. Furthermore, antibacterial agents such as chitin and chitosan may be combined. Among them, the combination strength S with silk protein, hive mouth-in, screen lantern, and the like, clothing, etc. is particularly preferable because a very characteristic soft and volumey texture can be obtained.

[0037] In the functionality-imparting agent of the present invention, components such as hydroxyproline or a hydroxyproline N-acyl yl derivative or a salt thereof may be used in a normal state. It may be used as a clathrate or vesicle structure with dextrin. In this case, not only oiliness but also hydrophilic compounds should be applied to fibers, nonwoven fabrics and fiber webs with good washing durability. In particular, the durability of washing can be improved by using a binder. The vesicle structure utilizes a surfactant that forms a polymer at a specific concentration. The surfactant molecule aggregate, that is, the vesicle bag-like bilayer membrane, has an aqueous phase inside. And has an oil phase. In the oil phase, an oily compound or the like is dissolved in a solvent such as benzyl benzoate and held in the oil phase portion of the vesicle structure.

 [0038] When the functionality-imparting agent of the present invention contains a binder, it can be fixed to a fiber product as it is, and when it does not contain a binder, it can be fixed using a separate binder. Can do. Examples of the binder include acrylic ester-based, for example, Pararesin GH-S manufactured by Ohara Paradum Chemical Co., Ltd., urethane-based binders, for example, Parasol PN-20 manufactured by Ohara Paradum Chemical Co., Ltd., silicone binders such as Toray Silicone Co., Ltd. It is preferable to use Toray Silicone BY22-826 made by the company and other polymers such as fluorine and epoxy. The amount of the binder used is preferably 0.5 to 25 parts by weight relative to 0.01 to 30 parts by weight of hydroxyproline or an N-acylated derivative of hydroxyproline or a salt thereof.

[0039] It should be noted that in the present invention, such a functionality-imparting agent is fixed to a fiber product, and the fiber product is retained. Functionality such as moisture, skin aging control and skin improvement, anti-atopy, anti-inflammatory, wound healing effect, pressure ulcer prevention, etc. can be added. Use a treatment solution containing a binder, attach it to textiles using a known method such as dubbing, padding, coating, spraying, etc., and fix it dry!

 [0040] The fiber product to be treated is not particularly limited in terms of the type of fiber, such as yarn, woven fabric, knitted fabric, non-woven fabric, and fiber web, which may be misaligned. The adhesion amount of the function-imparting agent to the fiber product is not particularly limited, but is usually about 0.05 to 5% by weight, preferably 1 to 3% by weight in terms of solid content.

 [0041] The building materials of the present invention 'bedding materials and products, interior materials and products, automotive interior materials and products, care materials and products are hydroxyproline, N-acylated derivatives of hydroxyproline or salts thereof Indicates fabric, blanket, sheets, chair fabric, carpet, car seat fabric, seat cover, etc., which are bonded to fibers such as cotton ιοο%, cotton Z polyester blend, hemp Z polyester blend, etc. Any of the hydroxyproline, the N-acylated derivative of hydroxyproline or a salt thereof may be used in the article. It is preferable to use hydroxyproline, acetyl hydroxyproline and the like.

 [0042] The garment of the present invention is hydroxyproline or a hydroxyproline N-acylation derivative or a salt thereof made of 100% cotton, 100% polyester, cotton Z polyester blend, 100% nylon, cotton Z nylon blend. This refers to clothing such as underwear, pantyhose, tights, shirts, blouses, casual wear, jeans, pants, etc. bonded to textiles, etc., and hydroxyproline or N-acyl 匕 derivative of hydroxyproline used in the clothing or its salt is Any of them may be used, but it is preferable to use hydroxyproline, acetyl hydroxyproline, or the like.

[0043] The cloth ommu, paper ommu, wet tissue, and tissue paper of the present invention use hydroxyproline or an N-acylated derivative of hydroxyproline or a salt thereof, and cotton woven paper and paper ommu are usually used for the cloth ommu. The water-absorbent fats and oils (see Japanese Patent Application Laid-Open No. 9-157543) and the wet tissue are those produced by bonding to paper. It may also be used in combination with antibacterial agents and deodorizers that are highly safe and natural products, antibacterial agents such as silver colloids, and deodorants. Cloth, paper, wet tissue, tissue paper Any hydroxyproline or hydroxyproline N-acylated derivative or salt thereof may be used for par, but hydroxyproline, acetyl hydroxyproline, etc. are preferably used.

[0044] This specification includes the contents described in the specification of Japanese Patent Application No. 2005-134124, which is the basis of the priority of the present application.

 Example

 [0045] Next, examples of the present invention will be described. In the examples, the term "parts" is used unless otherwise specified.

Indicates parts by weight.

[Example 1]

 N-acetyl-trans-4-hydroxy-L-proline 20 parts, ammonium glycyrrhizinate 20 parts, ethanol 5 parts, lauryl alcohol ethylene oxide 10 parts calories 10 parts, silicone resin as binder ( Toray Silicone Co., Ltd. manufactured by Toray Silicone BY22-826; the same shall apply hereinafter) was made into 20 parts, and the remainder was made up to 100 parts in total with water to give a functional additive for fiber fabrics.

[0047] Next, a cotton plain fabric with a basis weight of 300 gZm ² was dipped in a solution obtained by diluting the above-mentioned functionality-imparting agent with water so as to be lOOgZL, and then squeezed with a mandala so as to obtain a pickup rate of 100%. And pre-dried. Next, it was heat treated at 170 ° C. for 3 minutes to obtain a nursing sheet. This product has a pressure ulcer prevention effect and is very useful as a nursing sheet.

 [Example 2]

 20 parts of trans 4 hydroxy L proline, 20 parts of ammonium glycyrrhizinate, 5 parts of ethanol, 10 parts of 10 mol of tridecyl alcohol ethylene oxide, 20 parts of silicone resin as a noder, and the remaining water The total amount was 100 parts, and it was used as a functional additive for fiber fabrics.

[0049] Next, a cotton denim woven fabric with a basis weight of 300 gZm ² was immersed in a solution obtained by diluting the above-described function-imparting agent with water so as to be lOOgZL, and then squeezed with a mandala to obtain a pickup rate of 100%. Pre-dried with C. Next, it was heat treated at 170 ° C. for 3 minutes and sewed onto jeans. This product has a moisturizing and skin-beautifying effect and is very useful as a functional clothing.

[Example 3] N-acetyl-trans-1, 4-hydroxy-1, L-proline, 10 parts of squalane silica microcapsule, 15 parts of ethanol, 10 parts of ethylene oxide of lauryl alcohol, 10 parts of an adduct, 20 parts of silicone resin as a binder, The remainder was made up to 100 parts with water to make a functionality imparting agent for fiber webs.

[0051] Next, after a solution obtained by diluting the functionality-imparting agent to 30 gZL with water is attached to a wet tissue paper (cellulose fiber web) having a basis weight of 25 gZm ^{2 with} a kiss roll so that the pickup becomes 50%, Molded into a wet tissue product.

 [Comparative Example 1]

 Instead of N-acetylenotrans 4-hydroxy-L proline in Example 3, the amount of water used was increased to make a total of 100 parts.

[0053] The wet tissue obtained in Example 3 and Comparative Example 1 was applied to the elbow part, covered with a nylon film, and stopped with an adhesive tape for upper skin, allowed to stand for 4 hours, and then the skin was removed with a microscope. When the state was magnified, the product of Example 3 showed a skin beautifying effect such as improvement in skin quality, while the product of Comparative Example 1 was powerful without showing a skin beautifying effect.

[Example 4]

 20 parts of trans 4-hydroxy L-proline, 20 parts of the skeleton structure of squalane and raspberry extract, 5 parts of ethanol, 10 parts of 10 mol of ethylene oxide of lauryl alcohol, 20 parts of silicone-based resin as a binder, The remainder was made up to 100 parts with water to give a functionality-imparting agent for fiber fabrics.

[0055] Next, after immersing a fiber knit having a basis weight of 200 gZm ² (knit made of 20% nylon, 50% acrylic, 30% wool) in a solution diluted with water so that the above-mentioned functionality-imparting agent becomes 150 gZL. Then, it was squeezed with a mandal so that the pickup rate was 100%, and pre-dried at 100 ° C for 5 minutes. Next, it was heat-treated at 170 ° C. for 1 minute to obtain a limb protection cover for esthetics.

 [0056] At bedtime, one limb was covered with such a protective cover, and the other limb was without a protective cover, and after one week, the state of the limb was compared with a microscope photograph. As a result, the limbs with protective covers were moisturized and wrinkles were removed compared to limbs with strong protective covers.

[0057] All publications, patents and patent applications cited in this specification are used as is for reference. It shall be incorporated in the description.

Industrial applicability

 The present invention is used in the field of functional fiber products.

Claims

The scope of the claims  [I] An agent for imparting functionality to a textile product, comprising hydroxyproline or an N-acylated derivative of hydroxyproline or a salt thereof.  [2] The N-acylating derivative power of hydroxyproline. The functional agent according to claim 1, which is an N-acetylated derivative, an N-propionylated derivative, an N-propylylated derivative or an N-isoptyrylated derivative.  [3] Microencapsulation, inclusion with cyclodextrin, or vesicle structure The function-imparting agent according to claim 1, which is TV. [4] The functional agent according to claim 1, which contains a binder.  [5] A method for producing a functional fiber product, wherein the fiber product is treated with the functionality-imparting agent according to any one of claims 1 to 4. [6] Hydroxyproline or N-acylated derivative of hydroxyproline or a salt thereof combined with bedding materials and products, interior materials and products, automotive interior materials and products, and nursing materials and products . [7] N-acylated derivative power of hydroxyproline N-acetylated derivative, N-propionylated derivative, N-petitylated derivative or N-isoptyrylated derivative according to claim 6, Products, interior materials and products, automotive interior materials and products, as well as nursing materials and products. [8] Clothing to which hydroxyproline or N-acylated derivative of hydroxyproline or a salt thereof is bound.  [9] The garment according to claim 8, which is an N-acylated derivative of hydroxyproline, which is an N-acetylated derivative, an N-propionylated derivative, an N-petitylated derivative or an N-isoptyrylated derivative.  [10] Cloth, paper, wet tissue and tissue paper to which hydroxyproline or an N-acylated derivative of hydroxyproline or a salt thereof is bound.  [II] N-acylated derivative power of hydroxyproline N-acetylated derivative, N-propionylated derivative, N-propylylated derivative or N-isoptyrylated derivative Wet tissue and tissue paper.