JP4925791B2 - Fibers or textile products with antiviral properties and methods for producing them - Google Patents
Fibers or textile products with antiviral properties and methods for producing them Download PDFInfo
- Publication number
- JP4925791B2 JP4925791B2 JP2006302013A JP2006302013A JP4925791B2 JP 4925791 B2 JP4925791 B2 JP 4925791B2 JP 2006302013 A JP2006302013 A JP 2006302013A JP 2006302013 A JP2006302013 A JP 2006302013A JP 4925791 B2 JP4925791 B2 JP 4925791B2
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- Prior art keywords
- acid
- virus
- fiber
- cotton fabric
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- 239000000835 fiber Substances 0.000 title claims description 91
- 230000000840 anti-viral effect Effects 0.000 title claims description 32
- 238000000034 method Methods 0.000 title description 12
- 239000004753 textile Substances 0.000 title description 12
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- 239000005977 Ethylene Substances 0.000 claims description 4
- 239000011248 coating agent Substances 0.000 claims description 4
- 238000000576 coating method Methods 0.000 claims description 4
- 125000006353 oxyethylene group Chemical group 0.000 claims description 4
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- 241000700605 Viruses Species 0.000 description 49
- 239000002253 acid Substances 0.000 description 37
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- -1 aldehyde compounds Chemical class 0.000 description 28
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- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
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- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
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- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 3
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- ZHQLTKAVLJKSKR-UHFFFAOYSA-N homophthalic acid Chemical compound OC(=O)CC1=CC=CC=C1C(O)=O ZHQLTKAVLJKSKR-UHFFFAOYSA-N 0.000 description 3
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- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- NQPJDJVGBDHCAD-UHFFFAOYSA-N 1,3-diazinan-2-one Chemical compound OC1=NCCCN1 NQPJDJVGBDHCAD-UHFFFAOYSA-N 0.000 description 2
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- LEJBBGNFPAFPKQ-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethoxy)ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOC(=O)C=C LEJBBGNFPAFPKQ-UHFFFAOYSA-N 0.000 description 2
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 2
- XFCMNSHQOZQILR-UHFFFAOYSA-N 2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOC(=O)C(C)=C XFCMNSHQOZQILR-UHFFFAOYSA-N 0.000 description 2
- AOBIOSPNXBMOAT-UHFFFAOYSA-N 2-[2-(oxiran-2-ylmethoxy)ethoxymethyl]oxirane Chemical compound C1OC1COCCOCC1CO1 AOBIOSPNXBMOAT-UHFFFAOYSA-N 0.000 description 2
- RLHGFJMGWQXPBW-UHFFFAOYSA-N 2-hydroxy-3-(1h-imidazol-5-ylmethyl)benzamide Chemical compound NC(=O)C1=CC=CC(CC=2NC=NC=2)=C1O RLHGFJMGWQXPBW-UHFFFAOYSA-N 0.000 description 2
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- ZEYUSQVGRCPBPG-UHFFFAOYSA-N 4,5-dihydroxy-1,3-bis(hydroxymethyl)imidazolidin-2-one Chemical compound OCN1C(O)C(O)N(CO)C1=O ZEYUSQVGRCPBPG-UHFFFAOYSA-N 0.000 description 2
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- 150000002576 ketones Chemical class 0.000 description 1
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- 238000005259 measurement Methods 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
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- 238000002156 mixing Methods 0.000 description 1
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- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
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- BARWIPMJPCRCTP-CLFAGFIQSA-N oleyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCCOC(=O)CCCCCCC\C=C/CCCCCCCC BARWIPMJPCRCTP-CLFAGFIQSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
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- UFOIOXZLTXNHQH-UHFFFAOYSA-N oxolane-2,3,4,5-tetracarboxylic acid Chemical compound OC(=O)C1OC(C(O)=O)C(C(O)=O)C1C(O)=O UFOIOXZLTXNHQH-UHFFFAOYSA-N 0.000 description 1
- QUBQYFYWUJJAAK-UHFFFAOYSA-N oxymethurea Chemical compound OCNC(=O)NCO QUBQYFYWUJJAAK-UHFFFAOYSA-N 0.000 description 1
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- 229960003330 pentetic acid Drugs 0.000 description 1
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
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- 239000010452 phosphate Substances 0.000 description 1
- PTLWNCBCBZZBJI-UHFFFAOYSA-N piperidine-2,3-dicarboxylic acid Chemical compound OC(=O)C1CCCNC1C(O)=O PTLWNCBCBZZBJI-UHFFFAOYSA-N 0.000 description 1
- UBLWASUIZDSYFN-UHFFFAOYSA-N piperidine-3,4-dicarboxylic acid Chemical compound OC(=O)C1CCNCC1C(O)=O UBLWASUIZDSYFN-UHFFFAOYSA-N 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
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- 229920000223 polyglycerol Polymers 0.000 description 1
- 229920006389 polyphenyl polymer Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- ZUCRGHABDDWQPY-UHFFFAOYSA-N pyrazine-2,3-dicarboxylic acid Chemical compound OC(=O)C1=NC=CN=C1C(O)=O ZUCRGHABDDWQPY-UHFFFAOYSA-N 0.000 description 1
- GJAWHXHKYYXBSV-UHFFFAOYSA-N pyridinedicarboxylic acid Natural products OC(=O)C1=CC=CN=C1C(O)=O GJAWHXHKYYXBSV-UHFFFAOYSA-N 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 1
- 229960001755 resorcinol Drugs 0.000 description 1
- 239000010979 ruby Substances 0.000 description 1
- 229910001750 ruby Inorganic materials 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000015424 sodium Nutrition 0.000 description 1
- 235000019265 sodium DL-malate Nutrition 0.000 description 1
- HELHAJAZNSDZJO-OLXYHTOASA-L sodium L-tartrate Chemical compound [Na+].[Na+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O HELHAJAZNSDZJO-OLXYHTOASA-L 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
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- FQENQNTWSFEDLI-UHFFFAOYSA-J sodium diphosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])([O-])=O FQENQNTWSFEDLI-UHFFFAOYSA-J 0.000 description 1
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 1
- 235000019254 sodium formate Nutrition 0.000 description 1
- 229910001379 sodium hypophosphite Inorganic materials 0.000 description 1
- 239000001540 sodium lactate Substances 0.000 description 1
- 235000011088 sodium lactate Nutrition 0.000 description 1
- 229940005581 sodium lactate Drugs 0.000 description 1
- 239000001394 sodium malate Substances 0.000 description 1
- NVIFVTYDZMXWGX-UHFFFAOYSA-N sodium metaborate Chemical compound [Na+].[O-]B=O NVIFVTYDZMXWGX-UHFFFAOYSA-N 0.000 description 1
- 235000019983 sodium metaphosphate Nutrition 0.000 description 1
- 235000019795 sodium metasilicate Nutrition 0.000 description 1
- 229940045872 sodium percarbonate Drugs 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 235000011008 sodium phosphates Nutrition 0.000 description 1
- 235000019830 sodium polyphosphate Nutrition 0.000 description 1
- 229940048086 sodium pyrophosphate Drugs 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000001433 sodium tartrate Substances 0.000 description 1
- 229960002167 sodium tartrate Drugs 0.000 description 1
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- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 1
- 235000019818 tetrasodium diphosphate Nutrition 0.000 description 1
- 239000001577 tetrasodium phosphonato phosphate Substances 0.000 description 1
- 235000019303 thiodipropionic acid Nutrition 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- DXNCZXXFRKPEPY-UHFFFAOYSA-N tridecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCC(O)=O DXNCZXXFRKPEPY-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- GRPURDFRFHUDSP-UHFFFAOYSA-N tris(prop-2-enyl) benzene-1,2,4-tricarboxylate Chemical compound C=CCOC(=O)C1=CC=C(C(=O)OCC=C)C(C(=O)OCC=C)=C1 GRPURDFRFHUDSP-UHFFFAOYSA-N 0.000 description 1
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- NCPXQVVMIXIKTN-UHFFFAOYSA-N trisodium;phosphite Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])[O-] NCPXQVVMIXIKTN-UHFFFAOYSA-N 0.000 description 1
- 208000007089 vaccinia Diseases 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
- 229940051021 yellow-fever virus Drugs 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Description
本発明は、抗ウイルス性を備えた繊維又は繊維製品及びそれらの製造方法に関する。 The present invention relates to a fiber or fiber product having antiviral properties and a method for producing the same.
鳥インフルエンザは、家禽類のインフルエンザA型ウイルス感染症である。高病原性鳥インフルエンザウイルスは、養鶏業界に多大な経済損失を与えるだけでなく、高病原性鳥インフルエンザウイルスがヒトに対する感染性を有する新種のウイルスに変異することが危惧されている。 Avian influenza is an influenza A virus infection of poultry. The highly pathogenic avian influenza virus not only causes a great economic loss to the poultry industry, but it is feared that the highly pathogenic avian influenza virus will be mutated into a new type of virus that is infectious to humans.
そこで、養鶏業従事者及び医療従事者を感染から守るため、鳥インフルエンザウイルスに対して高い抗ウイルス性を備えた繊維又は繊維製品の開発が要望されている。 Then, in order to protect a poultry worker and a medical worker from infection, development of the fiber or fiber product provided with the high antiviral property with respect to avian influenza virus is desired.
一方、抗菌活性を有する種々の化合物が開発され、これらの化合物で処理した抗菌加工繊維又は繊維製品が提案されている。 On the other hand, various compounds having antibacterial activity have been developed, and antibacterial processed fibers or fiber products treated with these compounds have been proposed.
繊維又は繊維製品に抗菌性を付与するために使用されている抗菌活性化合物としては、例えば、2−ピリジンチオール−ジンク−1−オキシド、酸化亜鉛、イソプロピルメチルフェノール、3−(トリメチルシリル)プロピレンオクタデシルジメチルアンモニウムクロライド、ポリオキシエチレントリメチルアンモニウムクロリド、塩化ベンゼトニウム、塩化セチルピリジウム、アルキルトリメチルアンモニウム塩、p−イソオクチルフェノキシエトキシエチルジメチルベンジルアンモニウムクロリド、臭化フェノドデシウム、セチルジメチルベンジルアンモニウムクロリド、(3,4−ジクロルベンジル)ドデシルジメチルアンモニウムクロリド等が知られている。 Antibacterial active compounds used to impart antibacterial properties to fibers or textile products include, for example, 2-pyridinethiol-zinc-1-oxide, zinc oxide, isopropylmethylphenol, 3- (trimethylsilyl) propylene octadecyldimethyl Ammonium chloride, polyoxyethylenetrimethylammonium chloride, benzethonium chloride, cetylpyridium chloride, alkyltrimethylammonium salt, p-isooctylphenoxyethoxyethyldimethylbenzylammonium chloride, phenododecium bromide, cetyldimethylbenzylammonium chloride, (3,4- Dichlorobenzyl) dodecyldimethylammonium chloride and the like are known.
しかしながら、これらの抗菌活性を有する化合物は、後記試験例に示すように抗ウイルス活性を有していない。 However, these compounds having antibacterial activity do not have antiviral activity as shown in Test Examples described later.
繊維又は繊維製品に高い抗ウイルス性を付与し得る処理剤を提供することを課題とする。 It aims at providing the processing agent which can provide high antiviral property to a fiber or textiles.
繊維又は繊維製品に高い抗ウイルス性を付与し得る処理剤を開発すべく鋭意研究を重ねた結果、ポリ−オキシエチレン(ジメチルイミノ)エチレン(ジメチルイミノ)エチレンジクロライドを含有する組成物が、所望の繊維用抗ウイルス加工剤になり得ることを見い出した。 As a result of intensive research to develop a treatment agent capable of imparting high antiviral properties to fibers or textile products, a composition containing poly-oxyethylene (dimethylimino) ethylene (dimethylimino) ethylene dichloride is desired. It has been found that it can be an antiviral processing agent for textiles.
ポリ−オキシエチレン(ジメチルイミノ)エチレン(ジメチルイミノ)エチレンジクロライド(以下「PMIEC」という)は、抗菌活性を有することが知られており、そのため、PMIECの水溶液は、繊維の抗菌加工剤として使用されている(特開平5−310505号)。しかしながら、PMIECは、他の抗菌活性化合物と同様に、抗ウイルス性を有していることは全く知られていない。事実、PMIECで処理して得られる繊維又は繊維製品は、抗菌性を備えているものの、抗ウイルス性を備えていないことが、本発明者の研究により明らかになった(後記試験例1参照)。 Poly-oxyethylene (dimethylimino) ethylene (dimethylimino) ethylene dichloride (hereinafter referred to as “PMIEC”) is known to have antibacterial activity, and therefore, an aqueous solution of PMIEC is used as an antibacterial finishing agent for fibers. (Japanese Patent Laid-Open No. 5-310505). However, PMIEC, like other antibacterial active compounds, is not known to have antiviral properties at all. In fact, although the fiber or fiber product obtained by treating with PMIEC has antibacterial properties, it has been clarified by the inventor's research (see Test Example 1 below). .
本発明者は、PMIECについて更に研究を重ねるうち、PMIECで処理して得られる繊維又は繊維製品を更にソーピング処理することにより、繊維又は繊維製品に格段に優れた抗ウイルス性を付与し得るという驚くべき事実を見い出した。本発明は、このような知見に基づき完成されたものである。 As the present inventor further researches about PMIEC, it is surprising that the fiber or the fiber product obtained by the treatment with PMIEC can be further soaped to give the fiber or the fiber product a significantly superior antiviral property. I found the fact that should be. The present invention has been completed based on such findings.
本発明は、下記項1〜4に係る繊維用抗ウイルス加工剤、繊維又は繊維製品及びその製造方法を提供する。
項1.PMIECを含有する繊維用抗ウイルス加工剤。
項2.(1)PMIEC及び(2)被膜を形成し得る化合物を含有する繊維用抗ウイルス加工剤。
項3.繊維又は繊維製品を項1又は項2に記載の繊維用抗ウイルス加工剤で処理し、次いでソーピングして得られる、抗ウイルス性を備えた繊維又は繊維製品。
項4.繊維又は繊維製品に(1)PMIEC及び(2)被膜を形成し得る化合物を付着及び/又は含浸させ、次いで熱処理し、ソーピングすることにより、抗ウイルス性を備えた繊維又は繊維製品を製造する方法。
The present invention provides an antiviral processing agent for fibers, a fiber or a fiber product, and a method for producing the same according to items 1 to 4 below.
Item 1. Antiviral processing agent for fibers containing PMIEC.
Item 2. An antiviral processing agent for fibers containing (1) PMIEC and (2) a compound capable of forming a film.
Item 3. An antiviral fiber or fiber product obtained by treating a fiber or a fiber product with the antiviral processing agent for fiber according to Item 1 or 2, and then soaping the fiber or fiber product.
Item 4. A method for producing a fiber or textile product with antiviral properties by attaching and / or impregnating the fiber or textile product with (1) PMIEC and (2) a compound capable of forming a coating, followed by heat treatment and soaping .
繊維用抗ウイルス加工剤
本発明の繊維用抗ウイルス加工剤は、PMIECを含有する。
Antiviral processing agent for fibers The antiviral processing agent for fibers of the present invention contains PMIEC.
PMIECは、一般式(1) PMIEC has the general formula (1)
で表される繰り返し単位を有するポリカチオン化合物である。PMIECは、公知の化合物であり、低毒性で、皮膚及び眼に対する刺激性が低く、ヒトの肌に直接触れる繊維製品に使用しても安心して使用できる化合物である。PMIECの重量平均分子量は、1000〜10000程度である。 It is a polycation compound which has a repeating unit represented by these. PMIEC is a known compound that has low toxicity, low irritation to the skin and eyes, and can be used with confidence even when used in textile products that directly touch human skin. The weight average molecular weight of PMIEC is about 1000 to 10,000.
PMIECは水溶性であるため、PMIECは、通常、水溶液の形態で用いられる。 Since PMIEC is water-soluble, it is usually used in the form of an aqueous solution.
繊維用抗ウイルス加工剤に含まれるPMIECの量は、通常1〜80重量%程度、好ましくは10〜80重量%程度、より好ましくは30〜70重量%程度である。 The amount of PMIEC contained in the antiviral processing agent for fibers is usually about 1 to 80% by weight, preferably about 10 to 80% by weight, more preferably about 30 to 70% by weight.
繊維用抗ウイルス加工剤には、被膜を形成し得る化合物が含まれていてもよい。 The antiviral processing agent for fibers may contain a compound capable of forming a film.
被膜を形成し得る化合物としては、例えば、ポリカルボン酸、アルデヒド化合物、N−メチロール化合物、分子内にエポキシ基(グリシジル基)を有する化合物、分子内にビニル基を有する化合物、イソシアネート化合物、メラミン化合物等を挙げることができる。これらの中では、メラミン化合物が好適である。 Examples of compounds that can form a film include polycarboxylic acids, aldehyde compounds, N-methylol compounds, compounds having an epoxy group (glycidyl group) in the molecule, compounds having a vinyl group in the molecule, isocyanate compounds, and melamine compounds. Etc. Of these, melamine compounds are preferred.
(a) ポリカルボン酸
ポリカルボン酸としては、例えば分子中に少なくとも2個のカルボキシル基を有するポリカルボン酸を使用することができる。このようなポリカルボン酸としては、少なくとも2個のカルボキシル基を有するポリカルボン酸である限り従来公知のものを広く使用でき、例えば各種の脂肪族ポリカルボン酸、脂環族ポリカルボン酸、芳香族ポリカルボン酸等が挙げられる。これらカルボン酸は、水酸基、ハロゲン基、カルボニル基、炭素−炭素二重結合を有していても差し支えない。
(a) Polycarboxylic acid As the polycarboxylic acid, for example, a polycarboxylic acid having at least two carboxyl groups in the molecule can be used. As such a polycarboxylic acid, as long as it is a polycarboxylic acid having at least two carboxyl groups, conventionally known ones can be widely used. For example, various aliphatic polycarboxylic acids, alicyclic polycarboxylic acids, aromatics Polycarboxylic acid etc. are mentioned. These carboxylic acids may have a hydroxyl group, a halogen group, a carbonyl group, or a carbon-carbon double bond.
分子中に2個のカルボキシル基を有するポリカルボン酸としては、例えば飽和脂肪族ジカルボン酸、不飽和脂肪族ジカルボン酸、芳香族ジカルボン酸、脂環式ジカルボン酸等を挙げることができる。 Examples of the polycarboxylic acid having two carboxyl groups in the molecule include saturated aliphatic dicarboxylic acid, unsaturated aliphatic dicarboxylic acid, aromatic dicarboxylic acid, and alicyclic dicarboxylic acid.
飽和脂肪族ジカルボン酸としては、具体的にはシュウ酸、マロン酸、コハク酸、グルタル酸、アジピン酸、ピメリン酸、スベリン酸、アゼライン酸、セバシン酸、ウンデカン二酸、ドデカン二酸、ブラシル酸、プロピルマロン酸、ブチルマロン酸、ヘプチルマロン酸、ジプロピルマロン酸、リンゴ酸、酒石酸、アスパラギン酸、グルタミン酸、イミノジ酢酸、チオジプロピオン酸、チオマレイン酸等を例示できる。 Specific examples of the saturated aliphatic dicarboxylic acid include oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, undecanedioic acid, dodecanedioic acid, brassylic acid, Examples include propylmalonic acid, butylmalonic acid, heptylmalonic acid, dipropylmalonic acid, malic acid, tartaric acid, aspartic acid, glutamic acid, iminodiacetic acid, thiodipropionic acid, thiomaleic acid and the like.
不飽和脂肪族ジカルボン酸としては、具体的にはマレイン酸、フマル酸、イタコン酸、シトラコン酸、ヘキサジエン二酸(ムコン酸)、ドデカジエン二酸等を例示できる。 Specific examples of the unsaturated aliphatic dicarboxylic acid include maleic acid, fumaric acid, itaconic acid, citraconic acid, hexadiene diacid (muconic acid), dodecadiene diacid and the like.
芳香族ジカルボン酸としては、具体的にはフタル酸、イソフタル酸、テレフタル酸、ホモフタル酸、ヘキサヒドロテレフタル酸、ナフタレンジカルボン酸、ビフェニルジカルボン酸、メチルフタル酸、ヒドロキシイソフタル酸、ヒドリンデンジカルボン酸、ジフェニルエーテルジカルボン酸、ベンゾフェノンジカルボン酸、カルボキシメチル安息香酸、トリフルオロメチルフタル酸、アゾキシベンゼンジカルボン酸、ヒドラゾベンゼンジカルボン酸、スルホイソフタル酸、ジフェニルスルフォンジカルボン酸、ピリジンジカルボン酸、ケリダム酸、ピラジンジカルボン酸等を例示できる。 Specific examples of aromatic dicarboxylic acids include phthalic acid, isophthalic acid, terephthalic acid, homophthalic acid, hexahydroterephthalic acid, naphthalene dicarboxylic acid, biphenyl dicarboxylic acid, methyl phthalic acid, hydroxyisophthalic acid, hydrindene dicarboxylic acid, diphenyl ether dicarboxylic acid. Acid, benzophenone dicarboxylic acid, carboxymethyl benzoic acid, trifluoromethyl phthalic acid, azoxybenzene dicarboxylic acid, hydrazobenzene dicarboxylic acid, sulfoisophthalic acid, diphenylsulfone dicarboxylic acid, pyridinedicarboxylic acid, keridamic acid, pyrazine dicarboxylic acid, etc. It can be illustrated.
脂環式ジカルボン酸としては、具体的にはヘット酸、4−シクロヘキセン−1,2−ジカルボン酸、シクロプロパンジカルボン酸、シクロブタンジカルボン酸、シクロペンタンジカルボン酸、シクロヘキサンジカルボン酸、ピペリジン−2,3−ジカルボン酸(ヘキサヒドロキノリン酸)、ピペリジン−2,6−ジカルボン酸(ヘキサヒドロジピコリン酸)、ピペリジン−3,4−ジカルボン酸(ヘキサヒドロシンコメロン酸)等を例示できる。 Specific examples of the alicyclic dicarboxylic acid include het acid, 4-cyclohexene-1,2-dicarboxylic acid, cyclopropanedicarboxylic acid, cyclobutanedicarboxylic acid, cyclopentanedicarboxylic acid, cyclohexanedicarboxylic acid, piperidine-2,3- Examples include dicarboxylic acid (hexahydroquinolinic acid), piperidine-2,6-dicarboxylic acid (hexahydrodipicolinic acid), piperidine-3,4-dicarboxylic acid (hexahydrocincomeronic acid), and the like.
本発明において、ポリカルボン酸として、分子中に少なくとも3個のカルボキシル基を有するポリカルボン酸を使用するのが好ましい。このようなポリカルボン酸としては、少なくとも3個のカルボキシル基を有するポリカルボン酸である限り従来公知のものを広く使用でき、例えば各種の脂肪族ポリカルボン酸、脂環族ポリカルボン酸、芳香族ポリカルボン酸等が挙げられる。これらカルボン酸は、水酸基、ハロゲン基、カルボニル基、炭素−炭素二重結合を有していても差し支えない。 In the present invention, it is preferable to use a polycarboxylic acid having at least three carboxyl groups in the molecule as the polycarboxylic acid. As such a polycarboxylic acid, as long as it is a polycarboxylic acid having at least three carboxyl groups, conventionally known ones can be widely used. For example, various aliphatic polycarboxylic acids, alicyclic polycarboxylic acids, aromatics Polycarboxylic acid etc. are mentioned. These carboxylic acids may have a hydroxyl group, a halogen group, a carbonyl group, or a carbon-carbon double bond.
少なくとも3個のカルボキシル基を有するポリカルボン酸としては、脂肪族トリカルボン酸、脂肪族テトラカルボン酸、脂肪族ペンタカルボン酸、脂肪族ヘキサカルボン酸、芳香族ポリカルボン酸、カルボン酸ポリマー等を例示できる。 Examples of the polycarboxylic acid having at least three carboxyl groups include aliphatic tricarboxylic acid, aliphatic tetracarboxylic acid, aliphatic pentacarboxylic acid, aliphatic hexacarboxylic acid, aromatic polycarboxylic acid, and carboxylic acid polymer. .
脂肪族トリカルボン酸としては、具体的には、トリカルバリル酸、アコニチン酸、メチルシクロヘキセントリカルボン酸、クエン酸、1,2,3−ブタントリカルボン酸等を例示できる。 Specific examples of the aliphatic tricarboxylic acid include tricarballylic acid, aconitic acid, methylcyclohexeric acid, citric acid, 1,2,3-butanetricarboxylic acid, and the like.
脂肪族テトラカルボン酸としては、具体的には、ブタンテトラカルボン酸、シクロペンタンテトラカルボン酸、テトラヒドロフランテトラカルボン酸、メチルテトラヒドロフタル酸とマレイン酸のエン付加物、エチレンジアミン四酢酸、トランス−1,2−ジアミノシクロヘキサン四酢酸、グリコールエーテルジアミン四酢酸、ジフタル酸、エポキシ化コハク酸二量化物等を例示できる。 Specific examples of the aliphatic tetracarboxylic acid include butanetetracarboxylic acid, cyclopentanetetracarboxylic acid, tetrahydrofurantetracarboxylic acid, ene adducts of methyltetrahydrophthalic acid and maleic acid, ethylenediaminetetraacetic acid, trans-1,2 Examples include diaminocyclohexane tetraacetic acid, glycol ether diamine tetraacetic acid, diphthalic acid, and epoxidized succinic acid dimer.
脂肪族ペンタカルボン酸としては、具体的には、ジエチレントリアミン五酢酸等を例示できる。 Specific examples of the aliphatic pentacarboxylic acid include diethylenetriaminepentaacetic acid.
脂肪族ヘキサカルボン酸としては、具体的には、トリエチレンテトラミン六酢酸等を例示できる。 Specific examples of the aliphatic hexacarboxylic acid include triethylenetetramine hexaacetic acid.
芳香族ポリカルボン酸としては、具体的には、トリメリット酸、ピロメリット酸、ビフェニルテトラカルボン酸、ベンゾフェノンテトラカルボン酸、ジフェニルスルホンテトラカルボン酸等を例示できる。 Specific examples of the aromatic polycarboxylic acid include trimellitic acid, pyromellitic acid, biphenyltetracarboxylic acid, benzophenonetetracarboxylic acid, and diphenylsulfonetetracarboxylic acid.
カルボン酸ポリマーとしては、具体的には、アクリル酸重合物、クロトン酸重合物、マレイン酸重合物、イタコン酸(又は無水イタコン酸)重合物、アクリル酸・メタアクリル酸共重合物、アクリル酸・(無水)マレイン酸共重合物、メタアクリル酸・(無水)マレイン酸共重合物、アクリル酸・イタコン酸共重合物、アクリル酸・3−ブテン−1,2,3−トリカルボン酸共重合物、(無水)マレイン酸・α−メチルスチレン共重合物、(無水)マレイン酸・スチレン共重合物(スチレンと無水マレイン酸よりディールス・アルダー反応とエン反応によって生じたテトラカルボン酸を含む)、(無水)マレイン酸・アクリル酸アルキル共重合物、アクリル酸・3−ブテン−1,2,3−トリカルボン酸・アクリル酸アルキル共重合物、メタアクリル酸・(無水)マレイン酸・メタアクリル酸アルキル共重合物、(無水)マレイン酸・アクリル酸アルキル・メタアクリル酸アルキル共重合物、(無水)マレイン酸・アクリル酸アルキル・スチレン共重合物、アクリル酸・(無水)マレイン酸・アクリル酸アルキル・スチレン共重合物、メタアクリル酸・(無水)マレイン酸・アクリル酸2−エチルヘキシル・メタアクリル酸メチル・メタアクリル酸2−ヒドロキシエチル・スチレン共重合物等を例示できる。 Specific examples of the carboxylic acid polymer include acrylic acid polymer, crotonic acid polymer, maleic acid polymer, itaconic acid (or itaconic anhydride) polymer, acrylic acid / methacrylic acid copolymer, acrylic acid / (Anhydrous) maleic acid copolymer, methacrylic acid / (anhydrous) maleic acid copolymer, acrylic acid / itaconic acid copolymer, acrylic acid / 3-butene-1,2,3-tricarboxylic acid copolymer, (Anhydrous) maleic acid / α-methylstyrene copolymer, (anhydrous) maleic acid / styrene copolymer (including tetracarboxylic acid produced by Diels-Alder reaction and ene reaction from styrene and maleic anhydride), (anhydrous ) Maleic acid / alkyl acrylate copolymer, acrylic acid / 3-butene-1,2,3-tricarboxylic acid / alkyl acrylate copolymer, meta Kuryl acid / (anhydrous) maleic acid / alkyl methacrylate copolymer, (anhydrous) maleic acid / alkyl acrylate / alkyl methacrylate copolymer, (anhydrous) maleic acid / alkyl acrylate / styrene copolymer, Acrylic acid, (anhydrous) maleic acid, alkyl acrylate, styrene copolymer, methacrylic acid, (anhydrous) maleic acid, 2-ethylhexyl acrylate, methyl methacrylate, 2-hydroxyethyl methacrylate, styrene copolymer Examples can be given.
これらポリカルボン酸は夫々単独で又は2種以上を混合して使用される。 These polycarboxylic acids are used alone or in admixture of two or more.
これらのポリカルボン酸のうち、トリカルバリル酸、アコニチン酸、クエン酸、1,2,3,4−ブタンテトラカルボン酸等の水溶性のポリカルボン酸は作業性が良好であることから好ましく、特に水溶性で四塩基酸の1,2,3,4−ブタンテトラカルボン酸が最も効果が優れており好ましい。 Among these polycarboxylic acids, water-soluble polycarboxylic acids such as tricarballylic acid, aconitic acid, citric acid, 1,2,3,4-butanetetracarboxylic acid are preferred because of their good workability, and in particular Water-soluble tetrabasic acid 1,2,3,4-butanetetracarboxylic acid is most effective and is preferred.
これらのポリカルボン酸を使用する場合、ポリオールを併用するのが好ましい。 When these polycarboxylic acids are used, it is preferable to use a polyol in combination.
ポリオールとしては、オキシエチレン基と少なくとも2個のアルコール性水酸基とを有するものである限り、従来公知のものを広く使用でき、具体的にはポリエチレンオキシド又はアミン類、フェノール類、アルコール類等の2個以上の活性水素を有する化合物のエチレンオキシド付加物が挙げられる。これらポリオールは夫々単独で又は2種以上を混合して使用される。 As the polyol, as long as it has an oxyethylene group and at least two alcoholic hydroxyl groups, conventionally known ones can be widely used. Specifically, polyethylene oxide or amines, phenols, alcohols, etc. And an ethylene oxide adduct of a compound having one or more active hydrogens. These polyols are used alone or in admixture of two or more.
2個以上の活性水素を有する化合物としては、ネオペンチルグリコール、メチルペンタンジオール、トリメチルペンタンジオール等の炭素数5〜12のジオール及びそれらの分岐アルコール;ポリプロピレングリコール、1,2−ブチレンオキシドの重合物、ポリ(1,4−ブチレングリコール)等のポリエーテルアルコール類;グリセリン、ジグリセリン、トリグリセリン、ポリグリセリン、トリメチロールエタン、トリメチロールプロパン、ペンタエリスリトール、ジペンタエリスリトール等の3個以上の水酸基を有するアルコール類;シクロヘキサンジオール、シクロヘキサンジメタノール、水添ビスフェノールA、スピログリコール及びそれらの幾何異性体等の脂環アルコール類;キシリトール、ソルビトール、マンニトール、エリスリトール等の還元糖;キシロース、ソルボース、アラビノース、リボース、エリスロース、ガラクトース、ソルビタン等の単糖類;ラクトース、ショ糖、マルトース等の二糖類;ハイドロキノン、レゾルシン、カテコール、ビスフェノールA、ビスフェノールS、フェノールノボラック、クレゾールノボラック等のフェノール類;アンモニア、炭素数1〜22のモノアルキルアミン、アルキレンジアミン、アルキレントリアミン、アニリン、o−、m−、p−フェニレンジアミン、キシリレンジアミン、ジアミノジフェニルメタン、ジアミノジフェニルスルホン、ジアミノジフェニルエーテル、ジアミノジフェニルケトン、アニリンとホルマリンの重縮合物等のアミン類を挙げることができる。
(b) アルデヒド化合物
アルデヒド化合物としては、例えばホルムアルデヒド、ジアルデヒド(グリオキザール)等が挙げられる。
(c) N−メチロール化合物
N−メチロール化合物としては、例えばジメチロール尿素及びそのメチル化物、ジメチロールエチレン尿素及びそのメチル化物、ジメチロールウロン及びそのメチル化物、ジメチロールトリアゾン及びそのメチル化物、ジメチロールプロピレン尿素及びそのメチル化物、ジメチロールジヒドロキシエチレン尿素、メチル化ジメチロールジメトキシエチレン尿素、1,3−ジメチル−4,5−ジヒドロキシエチレン尿素及びそのメチル化物、ジメチロール−4−メトキシ−5,5−ジメチルプロピレン尿素及びそのメチル化物、ジメチロールアルキルカーバメイト及びそのメチル化物、テトラメチロールグリオキザールモノウレイン及びそのメチル化物等が挙げられる。
Examples of the compound having two or more active hydrogens include diols having 5 to 12 carbon atoms such as neopentyl glycol, methylpentanediol, and trimethylpentanediol, and branched alcohols thereof; polypropylene glycol, polymer of 1,2-butylene oxide Polyether alcohols such as poly (1,4-butylene glycol); three or more hydroxyl groups such as glycerin, diglycerin, triglycerin, polyglycerin, trimethylolethane, trimethylolpropane, pentaerythritol, dipentaerythritol Alcohols having: cycloaliphatic alcohols such as cyclohexanediol, cyclohexanedimethanol, hydrogenated bisphenol A, spiroglycol and their geometric isomers; xylitol, sorbitol, mannitol, erythritol Reducing sugars such as lithol; monosaccharides such as xylose, sorbose, arabinose, ribose, erythrose, galactose, sorbitan; disaccharides such as lactose, sucrose, maltose; hydroquinone, resorcin, catechol, bisphenol A, bisphenol S, phenol novolac Phenols such as cresol novolac; ammonia, C1-C22 monoalkylamine, alkylenediamine, alkylenetriamine, aniline, o-, m-, p-phenylenediamine, xylylenediamine, diaminodiphenylmethane, diaminodiphenylsulfone, Examples include amines such as diaminodiphenyl ether, diaminodiphenyl ketone, and polycondensates of aniline and formalin.
(b) Aldehyde compound Examples of the aldehyde compound include formaldehyde and dialdehyde (glyoxal).
(c) N-methylol compound Examples of the N-methylol compound include dimethylol urea and its methylated product, dimethylolethyleneurea and its methylated product, dimethyloluron and its methylated product, dimethyloltriazone and its methylated product, and dimethylol. Propylene urea and its methylated product, dimethylol dihydroxyethylene urea, methylated dimethylol dimethoxyethylene urea, 1,3-dimethyl-4,5-dihydroxyethylene urea and its methylated product, dimethylol-4-methoxy-5,5-dimethyl Examples include propylene urea and its methylated product, dimethylol alkyl carbamate and its methylated product, tetramethylol glyoxal monourene and its methylated product, and the like.
これらの中でも、ジメチロールジヒドロキシエチレン尿素が好ましい。 Among these, dimethylol dihydroxyethylene urea is preferable.
市販品としては、住友化学工業社製のスミテックスレジンシリーズ、三木理研社製のリケンレジンシリーズ等が挙げられる。
(d) 分子内にエポキシ基(グリシジル基)を有する化合物
分子内にエポキシ基(グリシジル基)を有する化合物としては、例えば脂肪族エポキシ化合物、ジグリシジル化合物、トリグリシジル化合物、ポリグリシジル化合物、脂環式エポキシ化合物、異節環状型エポキシ化合物、活性ビニル化合物の他、ビスフェノールA−エピクロルヒドリン化合物、ビスフェノールA−ジグリシジルエーテル化合物及びそのエチレンオキシド付加物又はプロピレンオキシド付加物、ビスフェノールF−ジグリシジルエーテル化合物、水素化ビスフェノールA−ジグリシジルエーテル化合物、水素化ビスフェノールF−ジグリシジルエーテル化合物等が挙げられる。
Examples of commercially available products include Sumitex Chemical Series manufactured by Sumitomo Chemical Co., Ltd. and Riken Resin Series manufactured by Miki Riken.
(d) Compound having an epoxy group (glycidyl group) in the molecule Examples of the compound having an epoxy group (glycidyl group) in the molecule include aliphatic epoxy compounds, diglycidyl compounds, triglycidyl compounds, polyglycidyl compounds, and alicyclic compounds. In addition to epoxy compounds, heterocyclic epoxy compounds, active vinyl compounds, bisphenol A-epichlorohydrin compounds, bisphenol A-diglycidyl ether compounds and their ethylene oxide or propylene oxide adducts, bisphenol F-diglycidyl ether compounds, hydrogenation Examples thereof include bisphenol A-diglycidyl ether compounds and hydrogenated bisphenol F-diglycidyl ether compounds.
脂肪族エポキシ化合物としては、例えばエポキシ化大豆油、エポキシ化オレイルオレート等が挙げられる。 Examples of the aliphatic epoxy compound include epoxidized soybean oil and epoxidized oleyl oleate.
ジグリシジル化合物としては、一般式(2) As the diglycidyl compound, the general formula (2)
[式中、Rは−O−R1−O−又は−O(R2O)n−を示す。ここでR1は炭素数2〜12の直鎖又は分枝鎖状アルキレン基を示す。R2は−CH2CH2−、−CH2−CH(CH3)−又は−(CH2)4−を示し、nは4〜50の整数を示す。]
で表されるジグリシジルエーテルを挙げることができ、具体的にはエチレングリコールジグリシジルエーテル、ジエチレングリコールジグリシジルエーテル、トリエチレングリコールジグリシジルエーテル、ポリエチレングリコールジグリシジルエーテル(n=4〜50)、プロピレングリコールジグリシジルエーテル、ジプロピレングリコールジグリシジルエーテル、トリプロピレングリコールジグリシジルエーテル、ポリプロピレングリコールジグリシジルエーテル(n=4〜50)、ネオペンチルグリコールジグリシジルエーテル、1,6−ヘキサンジオールジグリシジルエーテル、グリセロールジグリシジルエーテル、ジグリシジルポリシロキサン等が挙げられる。
[Wherein, R represents —O—R 1 —O— or —O (R 2 O) n —. Here, R 1 represents a linear or branched alkylene group having 2 to 12 carbon atoms. R 2 represents —CH 2 CH 2 —, —CH 2 —CH (CH 3 ) — or — (CH 2 ) 4 —, and n represents an integer of 4 to 50. ]
In particular, ethylene glycol diglycidyl ether, diethylene glycol diglycidyl ether, triethylene glycol diglycidyl ether, polyethylene glycol diglycidyl ether (n = 4 to 50), propylene glycol Diglycidyl ether, dipropylene glycol diglycidyl ether, tripropylene glycol diglycidyl ether, polypropylene glycol diglycidyl ether (n = 4 to 50), neopentyl glycol diglycidyl ether, 1,6-hexanediol diglycidyl ether, glycerol di Examples thereof include glycidyl ether and diglycidyl polysiloxane.
トリグリシジル化合物としては、例えばグリセロールトリグリシジルエーテル、トリメチロールプロパントリグリシジルエーテル等が挙げられる。 Examples of the triglycidyl compound include glycerol triglycidyl ether and trimethylolpropane triglycidyl ether.
ポリトリグリシジル化合物としては、例えばポリグリセロールポリグリシジルエーテル、ソルビトールポリグリシジルエーテル、ポリグリシジルポリシロキサン等が挙げられる。 Examples of the polytriglycidyl compound include polyglycerol polyglycidyl ether, sorbitol polyglycidyl ether, polyglycidyl polysiloxane, and the like.
脂環式エポキシ化合物としては、例えば3,4−エポキシシクロヘキシルメチル−3’,4’−エポキシシクロヘキサンカルボキシレート等が挙げられる。 Examples of the alicyclic epoxy compound include 3,4-epoxycyclohexylmethyl-3 ', 4'-epoxycyclohexanecarboxylate.
異節環状型エポキシ化合物としては、例えばトリグリシジルイソシアヌレート等が挙げられる。 Examples of the heterocyclic epoxy compound include triglycidyl isocyanurate.
上記一般式(2)で表されるジグリシジルエーテルの中でも、R1がエチレングリコール系、ポリエチレングリコール系、グリセリン系であるものが好ましい。 Among the diglycidyl ethers represented by the general formula (2), those in which R 1 is an ethylene glycol type, a polyethylene glycol type, or a glycerin type are preferable.
市販品としては、ナガセ化成工業社製のデナコールEXシリーズ等が挙げられる。
(e) 分子内にビニル基を有する化合物
分子内にビニル基を有する化合物としては、例えば分子内にジアクリロイル基を有する化合物、分子内にジメタクリロイル基を有する化合物、分子内にトリアリル基を有する化合物、分子内にテトラアリル基を有する化合物、分子内にペンタアリル基を有する化合物等を挙げることができる。
As a commercial item, Nagase Kasei Kogyo Co., Ltd. Denacol EX series etc. are mentioned.
(e) Compound having a vinyl group in the molecule Examples of the compound having a vinyl group in the molecule include a compound having a diacryloyl group in the molecule, a compound having a dimethacryloyl group in the molecule, and a triallyl group in the molecule. Examples thereof include compounds, compounds having a tetraallyl group in the molecule, compounds having a pentaallyl group in the molecule, and the like.
分子内にジアクリロイル基を有する化合物としては、具体的にはエチレングリコールジアクリレート、ジエチレングリコールジアクリレート、ポリエチレングリコールジアクリレート(n=3〜50)、1,4−ブタンジオールジアクリレート、1,6−ヘキサンジオールジアクリレート、1,9−ノナンジオールジアクリレート、ネオペンチルグリコールジアクリレート、ジメチロールトリシクロデカンジアクリレート、トリプロピレングリコールジアクリレート、ビスフェノールAのエチレンオキシド付加物ジアクリレート、ビスフェノールAのプロピレンオキシド付加物ジアクリレート、ヒドロキシピバリン酸ネオペンチルグリコールジアクリレート等を例示できる。 Specific examples of the compound having a diacryloyl group in the molecule include ethylene glycol diacrylate, diethylene glycol diacrylate, polyethylene glycol diacrylate (n = 3 to 50), 1,4-butanediol diacrylate, 1,6- Hexanediol diacrylate, 1,9-nonanediol diacrylate, neopentyl glycol diacrylate, dimethylol tricyclodecane diacrylate, tripropylene glycol diacrylate, ethylene oxide adduct diacrylate of bisphenol A, propylene oxide adduct of bisphenol A Examples include diacrylate and neopentyl glycol diacrylate hydroxypivalate.
分子内にジメタクリロイル基を有する化合物としては、具体的にはエチレングリコールジメタクリレート、ジエチレングリコールジメタクリレート、ポリエチレングリコールジメタクリレート(n=3〜50)、1,3−ブタンジオールジメタクリレート、1,4−ブタンジオールジメタクリレート、1,6−ヘキサンジオールジメタクリレート、1,9−ノナンジオールジメタクリレート、1,10−デカンジオールジメタクリレート、グリセリンジメタクリレート、ネオペンチルグリコールジメタクリレート、ジメチロールトリシクロデカンジメタクリレート、トリプロピレングリコールジメタクリレート、ビスフェノールAのエチレンオキシド付加物ジメタクリレート、ビスフェノールAのプロピレンオキシド付加物ジメタクリレート、ヒドロキシピバリン酸ネオペンチルグリコールジメタクリレート、ヘキサヒドロフタル酸ジアリル、ジアリルオルソフタレート、ジアリルイソフタレート、ジアリルテレフタレート、ジビニルベンゼン、1,1’−ビフェニル−2,2’−ジカルボン酸ジアリル、ジアリルクロレンデート、N,N−メチレンビスアクリルアミド等を例示できる。 Specific examples of the compound having a dimethacryloyl group in the molecule include ethylene glycol dimethacrylate, diethylene glycol dimethacrylate, polyethylene glycol dimethacrylate (n = 3 to 50), 1,3-butanediol dimethacrylate, 1,4- Butanediol dimethacrylate, 1,6-hexanediol dimethacrylate, 1,9-nonanediol dimethacrylate, 1,10-decanediol dimethacrylate, glycerin dimethacrylate, neopentyl glycol dimethacrylate, dimethylol tricyclodecane dimethacrylate, Tripropylene glycol dimethacrylate, ethylene oxide adduct dimethacrylate of bisphenol A, propylene oxide adduct dimethacrylate of bisphenol A, Droxypivalate neopentyl glycol dimethacrylate, diallyl hexahydrophthalate, diallyl orthophthalate, diallyl isophthalate, diallyl terephthalate, divinylbenzene, diallyl 1,1′-biphenyl-2,2′-dicarboxylate, diallyl chlorendate, N , N-methylenebisacrylamide and the like.
分子内にトリアリル基を有する化合物としては、具体的にはトリメチロールプロパントリアリルエーテル、トリメチロールプロパントリアクリレートとそのエチレンオキシド変性物、トリメチロールプロパントリメタクリレート、ペンタエリスリトールトリアリルエーテル、ペンタエリスリトールトリアクリレート、ペンタエリスリトールトリメタクリレート、トリアリルトリメリテート、トリアリルイソシアヌレート、トリアリルシアヌレート、トリアクリルホルマール、トリメタアリルイソシアヌレート等を例示できる。 As the compound having a triallyl group in the molecule, specifically, trimethylolpropane triallyl ether, trimethylolpropane triacrylate and its ethylene oxide modified product, trimethylolpropane trimethacrylate, pentaerythritol triallyl ether, pentaerythritol triacrylate, Examples include pentaerythritol trimethacrylate, triallyl trimellitate, triallyl isocyanurate, triallyl cyanurate, triacryl formal, and trimethallyl isocyanurate.
分子内にテトラアリル基を有する化合物としては、具体的にはジトリメチロールプロパンテトラアクリレート、ペンタエリスリトールテトラアクリレート等を例示できる。 Specific examples of the compound having a tetraallyl group in the molecule include ditrimethylolpropane tetraacrylate and pentaerythritol tetraacrylate.
分子内にペンタアリル基を有する化合物としては、具体的にはジペンタエリスリトールヘキサアクリレート等を例示できる。 Specific examples of the compound having a pentaallyl group in the molecule include dipentaerythritol hexaacrylate.
分子内にビニル基を有する化合物としては、分子内にジアクリロイル基を有する化合物や分子内にジメタクリロイル基を有する化合物が好ましく、特にポリエチレングリコールジアクリレート(n=3〜50)やポリエチレングリコールジメタクリレート(n=3〜50)が好ましい。
(f) イソシアネート化合物
イソシアネート化合物としては、例えばジイソシアネート化合物、トリイソシアネート化合物、ポリイソシアネート化合物等の他、m−イソプロペニル−α,α−ジメチルベンジルイソシアネート等を挙げることができる。
As the compound having a vinyl group in the molecule, a compound having a diacryloyl group in the molecule or a compound having a dimethacryloyl group in the molecule is preferable, and particularly polyethylene glycol diacrylate (n = 3 to 50) or polyethylene glycol dimethacrylate. (n = 3-50) is preferable.
(f) Isocyanate compound Examples of the isocyanate compound include diisocyanate compounds, triisocyanate compounds, polyisocyanate compounds, and m-isopropenyl-α, α-dimethylbenzyl isocyanate.
ジイソシアネート化合物としては、具体的にはトリレンジイソシアネート、4,4−ジフェニルメタンジイソシアネート、キシリレンジイソシアネート、1,3−ビス(イソシアナトメチル)シクロヘキサン、ヘキサメチレンジイソシアネート、ドデカメチレンジイソシアネート、テトラメチルキシリレンジイソシアネート、イソホロンジイソシアネート、1,5−ナフタレンジイソシアネート、o−トリジンジイソシアネート、ジシクロヘキシルメタンジイソシアネート等を例示できる。 Specific examples of the diisocyanate compound include tolylene diisocyanate, 4,4-diphenylmethane diisocyanate, xylylene diisocyanate, 1,3-bis (isocyanatomethyl) cyclohexane, hexamethylene diisocyanate, dodecamethylene diisocyanate, tetramethylxylylene diisocyanate, Examples include isophorone diisocyanate, 1,5-naphthalene diisocyanate, o-tolidine diisocyanate, and dicyclohexylmethane diisocyanate.
トリイソシアネート化合物としては、具体的にはトリフェニルメタントリイソシアネート等を例示できる。 Specific examples of the triisocyanate compound include triphenylmethane triisocyanate.
ポリイソシアネート化合物としては、具体的にはポリメチレンポリフェニルポリイソシアネート等を例示できる。 Specific examples of the polyisocyanate compound include polymethylene polyphenyl polyisocyanate.
本発明では、上記ジイソシアネート化合物、トリイソシアネート化合物、m−イソプロペニル−α,α−ジメチルベンジルイソシアネート等は、活性イソシアネート基がブロック剤によりブロックされたものであってもよい。ブロック剤としては、例えばオキシム(アセトオキシム、シクロヘキサノンオキシム)、ラクタム(ε−カプロラクタム)、ジエチルマロネート、アセト酢酸エチル、アセチルアセトン、重亜硫酸塩等を挙げることができる。 In the present invention, the diisocyanate compound, triisocyanate compound, m-isopropenyl-α, α-dimethylbenzyl isocyanate and the like may be those in which an active isocyanate group is blocked with a blocking agent. Examples of the blocking agent include oxime (acetoxime, cyclohexanone oxime), lactam (ε-caprolactam), diethyl malonate, ethyl acetoacetate, acetylacetone, bisulfite and the like.
これらの中でも、ジイソシアネート化合物が好ましく、ヘキサメチレンジイソシアネートが特に好ましい。 Among these, a diisocyanate compound is preferable and hexamethylene diisocyanate is particularly preferable.
市販品としては、第一工業製薬社製のエラストロンシリーズ等が挙げられる。
(g) メラミン化合物
メラミン化合物としては、例えば、メラミン、トリメチロールメラミン、ヘキサメチロールメラミン及びこれらのメチル化物等が挙げられる。
Examples of commercially available products include Elastron series manufactured by Daiichi Kogyo Seiyaku Co., Ltd.
(g) Melamine Compound Examples of the melamine compound include melamine, trimethylol melamine, hexamethylol melamine, and methylated products thereof.
被膜を形成し得る化合物としては、上記に例示した化合物を1種単独で使用してもよいし、2種以上混合して使用してもよい。これらの化合物がそれ自身で被膜を形成し得ない場合には、硬化触媒等の公知の添加剤が繊維用抗ウイルス加工剤に配合されるのがよく、その配合量は被膜の形成に必要な量でよい。 As the compound capable of forming a film, the compounds exemplified above may be used singly or in combination of two or more. When these compounds cannot form a film by themselves, a known additive such as a curing catalyst may be blended with the antiviral processing agent for fibers, and the blending amount is necessary for the formation of the film. The amount is sufficient.
繊維用抗ウイルス加工剤に含まれる上記化合物(被膜を形成し得る化合物)の量は、通常PMIEC100重量部に対して2〜5000重量部程度、好ましくは5〜2000重量部程度、より好ましくは10〜1000重量部程度である。硬化触媒等の公知の添加剤の配合量は被膜の形成に必要な量でよい。 The amount of the above-mentioned compound (compound capable of forming a coating) contained in the antiviral processing agent for fibers is usually about 2 to 5000 parts by weight, preferably about 5 to 2000 parts by weight, more preferably 10 to 100 parts by weight of PMIEC. About 1000 parts by weight. The amount of a known additive such as a curing catalyst may be an amount necessary for forming a film.
繊維又は繊維製品
本発明における繊維は、合成繊維、再生繊維及び天然繊維のいずれでもよい。
Fiber or fiber product The fiber in the present invention may be any of synthetic fiber, regenerated fiber and natural fiber.
合成繊維としては、公知のものを広く使用でき、例えばポリエステル、ナイロン、アクリル、アセテート、ビニロン、ポリエチレン、ポリプロピレン、ポリウレタン等が挙げられる。 As the synthetic fiber, known fibers can be widely used, and examples thereof include polyester, nylon, acrylic, acetate, vinylon, polyethylene, polypropylene, and polyurethane.
再生繊維としては、公知のものを広く使用でき、例えばビスコースレーヨン、銅アンモニアレーヨン、ポリノジック等が挙げられる。 Known fibers can be widely used as the recycled fiber, and examples thereof include viscose rayon, copper ammonia rayon, and polynosic.
天然繊維としては、公知のものを広く使用でき、例えば木綿、麻(亜麻、大麻、ラミー、マニラ麻、サイザル麻等)、ウール、カシミヤ、アルパカ、モヘヤ、絹、カポック、ケナフ、ハイビスカス繊維、サトウキビ繊維、バナナ繊維、竹繊維等が挙げられる。木綿や麻には、原綿そのものの他、苛性マーセル化した木綿や麻、液体アンモニアで処理した木綿や麻等が包含される。 Known natural fibers can be widely used, such as cotton, hemp (flax, cannabis, ramie, manila hemp, sisal hemp, etc.), wool, cashmere, alpaca, mohair, silk, kapok, kenaf, hibiscus fiber, sugarcane fiber. , Banana fiber, bamboo fiber and the like. Cotton and hemp include not only raw cotton itself but also caustic mercerized cotton and hemp, and cotton and hemp treated with liquid ammonia.
本発明の繊維は、上記各種繊維の混紡であってもよい。 The fiber of the present invention may be a blend of the above-mentioned various fibers.
また、本発明の繊維には、上記繊維の一次加工品、例えば糸、紐、ロープ、織物、編物、不織布、紙等が包含される。 The fibers of the present invention include primary processed products of the above fibers, such as yarns, strings, ropes, woven fabrics, knitted fabrics, non-woven fabrics, and papers.
本発明において、繊維製品とは、上記繊維を更に加工したもの、例えば外衣、中衣、内衣等の衣料、寝装品、インテリア等の製品を意味する。本発明の繊維製品としては、具体的にはコート、ジャケット、ズボン、スカート、ワイシャツ、ニットシャツ、ブラウス、セーター、カーディガン、ナイトウエア、肌着、サポーター、靴下、タイツ、帽子、スカーフ、マフラー、襟巻き、手袋、服の裏地、服の芯地、服の中綿、作業着、ユニフォーム、学童用制服等の衣料、カーテン、布団地、布団綿、枕カバー、シーツ、マット、カーペット、タオル、ハンカチ、マスク、フィルター等の製品を例示できる。また、本発明の繊維製品には、例えば壁布、壁紙、フロア外張り等の産業資材分野で使用される繊維製品の形態のものも包含される。 In the present invention, the textile product means a product obtained by further processing the above-described fiber, for example, a clothing such as an outer garment, a middle garment, an inner garment, a bedding product, or an interior. Specifically, the textile products of the present invention include coats, jackets, trousers, skirts, shirts, knitted shirts, blouses, sweaters, cardigans, nightwear, underwear, supporters, socks, tights, hats, scarves, mufflers, and collar wraps. , Gloves, clothing lining, clothing interlining, clothing padding, work clothes, uniforms, school uniforms, curtains, mattresses, duvet cotton, pillowcases, sheets, mats, carpets, towels, handkerchiefs, masks And a product such as a filter. The textile product of the present invention includes a textile product used in the field of industrial materials such as wall cloth, wallpaper, and floor covering.
抗ウイルス性を備えた繊維又は繊維製品の製造方法
抗ウイルス性を備えた繊維又は繊維製品は、処理されるべき繊維又は繊維製品に、本発明の繊維用抗ウイルス加工剤を付着及び/又は含浸させ、次いで熱処理し、ソーピングすることにより製造される。
Method for producing fiber or fiber product with antiviral property The fiber or fiber product with antiviral property adheres and / or impregnates the fiber or fiber product to be treated with the antiviral processing agent for fibers of the present invention. And then heat treated and soaped.
処理されるべき繊維又は繊維製品に、繊維用抗ウイルス加工剤を付着及び/又は含浸させるに当たっては、浸漬法、スプレー法、コーティング法等の公知の方法を広く適用することができる。 In adhering and / or impregnating the fiber or fiber product to be treated with the antiviral processing agent for fibers, known methods such as dipping, spraying, and coating can be widely applied.
本発明では、PMIEC及び被膜を形成し得る化合物を含有する処理液中に処理すべき繊維又は繊維製品を浸漬する、いわゆる、浸漬法を採用するのが好ましい。 In the present invention, it is preferable to employ a so-called dipping method in which fibers or fiber products to be treated are dipped in a treatment solution containing a PMIEC and a compound capable of forming a film.
以下、浸漬法につき詳述する。 Hereinafter, the immersion method will be described in detail.
処理液中のPMIEC濃度及び被膜を形成し得る化合物の濃度は、処理液の絞り率と必要とする担持量より算出した濃度に設定すればよい。 The concentration of the PMEC in the treatment liquid and the concentration of the compound capable of forming a film may be set to a concentration calculated from the squeezing rate of the treatment liquid and the required loading amount.
本発明では、一つの処理液中に所定濃度のPMIEC及び被膜を形成し得る化合物が全て含有されていてもよいし、これらPMIEC及び被膜を形成し得る化合物が別個の処理液中に含有されていてもよい。 In the present invention, all of the compounds capable of forming a predetermined concentration of PMIEC and a film may be contained in one treatment liquid, or these PMIEC and a compound capable of forming a film may be contained in separate treatment liquids. May be.
上記処理液のpHは1〜9、好ましくは2〜7に調整されていることが好ましい。処理液のpHがこの範囲であれば、本発明で所望する繊維又は繊維製品を得ることができる。当該範囲のpHは処理液に対して中和剤、即ち適当なアルカリ又は塩を添加することにより調整できる。 The pH of the treatment liquid is preferably adjusted to 1-9, preferably 2-7. If the pH of the treatment liquid is within this range, the fiber or fiber product desired in the present invention can be obtained. The pH in this range can be adjusted by adding a neutralizing agent, that is, an appropriate alkali or salt to the treatment liquid.
pHの調整に使用される中和剤として、例えば水酸化ナトリウム、重炭酸ナトリウム、炭酸ナトリウム、過炭酸ナトリウム、ホウ酸ナトリウム、メタホウ酸ナトリウム、水素化ホウ素ナトリウム、ケイ酸ナトリウム、メタケイ酸ナトリウム、亜硫酸ナトリウム、チオ硫酸ナトリウム、リン酸ナトリウム、メタリン酸ナトリウム、ポリリン酸ナトリウム、ピロリン酸ナトリウム、亜リン酸ナトリウム、次亜リン酸ナトリウム、ギ酸ナトリウム、酢酸ナトリウム、リンゴ酸ナトリウム、酒石酸ナトリウム、乳酸ナトリウム等が挙げられる。また、上記のナトリウム塩に代わり、カリウム塩、アンモニウム塩、メチルアミン、ジメチルアミン、トリメチルアミン、トリエチルアミン等の揮発性の低級アミンの塩も使用できる。これらの中和剤は、単独で又は2種以上を組み合わせて使用してもよい。 Examples of neutralizing agents used for pH adjustment include sodium hydroxide, sodium bicarbonate, sodium carbonate, sodium percarbonate, sodium borate, sodium metaborate, sodium borohydride, sodium silicate, sodium metasilicate, and sulfurous acid. Sodium, sodium thiosulfate, sodium phosphate, sodium metaphosphate, sodium polyphosphate, sodium pyrophosphate, sodium phosphite, sodium hypophosphite, sodium formate, sodium acetate, sodium malate, sodium tartrate, sodium lactate, etc. Can be mentioned. Further, in place of the above-mentioned sodium salt, salts of volatile lower amines such as potassium salt, ammonium salt, methylamine, dimethylamine, trimethylamine and triethylamine can also be used. These neutralizing agents may be used alone or in combination of two or more.
上記中和剤の添加量は、使用されるPMIEC及び被膜を形成し得る化合物の溶解量や種類にもよるが、処理液中の濃度として通常0.1〜10重量%程度とするのがよい。 The amount of the neutralizing agent to be added depends on the amount and type of the PMIEC used and the compound capable of forming a film, but the concentration in the treatment liquid is usually about 0.1 to 10% by weight. .
上記処理液を構成する溶媒としては有機溶媒でも差支えないが、安全、価格を考慮すれば水を溶媒にするのが好ましい。また処理液の形態は、所定の効果が得られる限り特に限定されるものではなく、溶液の形態であっても乳化液の形態であってもよいが、処理効率及び安全性の観点から水溶液であることが好ましい。 The solvent constituting the treatment liquid may be an organic solvent, but it is preferable to use water as a solvent in consideration of safety and price. The form of the treatment liquid is not particularly limited as long as a predetermined effect can be obtained, and may be in the form of a solution or an emulsion, but it may be an aqueous solution from the viewpoint of treatment efficiency and safety. Preferably there is.
上記処理液の繊維又は繊維製品に対する浸透速度は充分に速く、浸漬時間、浴温度に特に制限はない。通常、浸漬時間0.1〜300秒、浴温は10〜40℃で行われる。絞りは加工する製品によって異なり、夫々に適当な絞り方法、絞り率が採用できる。通常、絞り率は30〜200%で行うのが好ましい。 The permeation rate of the treatment liquid into the fiber or fiber product is sufficiently high, and there is no particular limitation on the immersion time and bath temperature. Usually, the immersion time is 0.1 to 300 seconds and the bath temperature is 10 to 40 ° C. The aperture varies depending on the product to be processed, and an appropriate aperture method and aperture ratio can be adopted for each. Usually, it is preferable that the drawing ratio is 30 to 200%.
浸漬、絞りを行った後、乾燥を行う。工業的には、乾燥温度は40〜150℃、時間は温度に応じて選定すればよい。 After soaking and squeezing, drying is performed. Industrially, the drying temperature may be 40 to 150 ° C., and the time may be selected according to the temperature.
本発明においては、PMIEC及び被膜を形成し得る化合物を付着及び/又は含浸させた繊維又は繊維製品を次いで加熱処理する。 In the present invention, the fiber or the fiber product to which the PMIEC and the compound capable of forming a film are attached and / or impregnated is then heat-treated.
加熱処理の温度は、通常100〜250℃、好ましくは120〜200℃、処理時間は20秒〜1時間である。 The temperature of the heat treatment is usually 100 to 250 ° C, preferably 120 to 200 ° C, and the treatment time is 20 seconds to 1 hour.
本発明では、加熱処理された繊維又は繊維製品をソーピング処理する。ソーピング処理により、繊維又は繊維製品に格段に優れた抗ウイルス作用を付与することができる。 In the present invention, the heat-treated fiber or fiber product is soaped. By the soaping treatment, a remarkably excellent antiviral effect can be imparted to the fiber or the fiber product.
ソーピング処理の条件は、特に限定されない。 The conditions for the soaping process are not particularly limited.
本発明の方法で得られる繊維又は繊維製品は、顕著に優れた抗ウイルス作用を備えている。 The fiber or fiber product obtained by the method of the present invention has a remarkably excellent antiviral effect.
本発明の繊維又は繊維製品が有効なウイルスとしては、例えば、単純ヘルペスウイルス1型 (Herpes simplex I)、単純ヘルペスウイルス2型 (Herpes simplex II)等のシンプレックスウイルス属 (Simplexvirus)に属するウイルス;水痘帯状疱疹ウイルス(Varicella-zoster virus)等のワリセロウイルス属(Varicellovirus)に属するウイルス;エプスタイン・バール・ウイルス(Epstein-Barr virus)等のリンホクリプトウイルス属(lymphocryptovirus)に属するウイルス;ワクシニアウイルス(Vaccinia virus)、痘瘡ウイルス(Variola virus)、牛痘ウイルス(Cowpox virus)、サル痘ウイルス(Monkeypox virus) 等のオルトポックスウイルス属 (Orthopoxvirus, Vaccinia Subgroup)に属するウイルス;SARSウイルス等のコロナウイルス科 (Coronaviridae)に属するウイルス;黄熱病ウイルス(Yellow fever virus)、日本脳炎ウイルス(Japanese encephalitis virus)、C型肝炎ウイルス(hepatitis C virus)、デング熱ウイルス(Dengue fever virus)、西ナイルウイルス等のフラビウイルス属(Flavivirus)に属するウイルス;牛ウイルス性下痢ウイルス、豚コレラウイルス、ボーダー病ウイルス等のペスチウイルス属(pesti virus) に属するウイルス;口蹄疫ウイルス(Foot-and-mouth disease virus)等のアフトウイルス属(Aphthovirus)に属するウイルス;ポリオウイルス(Poliovirus)等のエンテロウイルス属(Enterovirus)に属するウイルス;A型肝炎ウイルス(Hepatitis A virus)等のヘパトウイルス属(Hepatovirus)に属するウイルス;風邪ウイルス(Common cold virus)等のライノウイルス属(Rhinovirus)に属するウイルス;風疹ウイルス(Rubella virus)等のルビウイルス属(Rubivirus)に属するウイルス;脳炎ウイルス(Encephalitis virus)等のアルファウイルス属(Alphavirus, Arbovirus group A)に属するウイルス;E型肝炎ウイルス(Hepatitis E virus)等のへぺウイルス属 (Hepevirus)に属するウイルス;タバコモザイクウイルス等のトバモウイルス属(Tobamovirus)に属するウイルス;マールブルグウイルス(Marburg virus);エボラウイルス(Ebola virus);狂犬病ウイルス(Rabies virus)等のリッサウイルス属 (Lyssavirus, Rabies virus group)に属するウイルス;水疱性口内炎ウイルス(Vesicular stomatitis virus)等のベシクロウイルス属Vesiculovirus, Vesicular stomatitis virus group)に属するウイルス;はしかウイルス(Measles virus)等のモルビリウイルス属 (Morbillivirus)に属するウイルス;おたふくかぜウイルス(Mumps virus)等のルブラウイルス属(Rubulavirus)に属するウイルス;仙台ウイルス(Sendai virus)等のレスピロウイルス属(Respirovirus)に属するウイルス;ニューカッスル病ウイルス(Newcastle disease virus)等のアブラウイルス属 (Avulavirus)に属するウイルス;RSウイルス(Respiratory syncytial virus)等のニューモウイルス属(Pneumovirus, Respiratory syncytial virus group) に属するウイルス;ヒト・メタニューモウイルス(human metapneumovirus)等のメタニューモウイルス属 (Metapneumovirus)に属するウイルス;ニパウイルス (Nipah virus)等のヘニパウイルス属(Henipavirus)に属するウイルス;インフルエンザウイルスA,B,C(Influenza virus A,B,C)等のオルソミキソウイルス科インフルエンザ属(Influenza virus)に属するウイルス;ブニヤムウェラウイルス(Bunyamwera virus )等のブニヤウイルス属(Bunyavirus, Bunyamwear subgroup)に属するウイルス;ハンタウイルス(Hantavirus)等のハンタウイルス属 (Hantaviruses)に属するウイルス;リンパ球性脈絡髄膜炎ウイルス(Lymphocytic choriomeningitis virus)、ラッサウイルス等のアレナウイルス属(Arenavirus, LCM virus group)に属するウイルス;ヒト免疫不全ウイルス (Human immunodeficiency virus, HIV)等のレンチウイルス属(Lentivirus);成人T細胞白血病ウイルス(Human T-lymphotropic virus, Adult T cell leukemia virus)等のレトロウイルス科オンコウイルス属(Oncovirus, Type C oncovirus group)に属するウイルス;B型肝炎ウイルス(hepatitis B virus);カリフラワーモザイクウイルス(Cauliflower Mosaic virus)等のカリモウイルス属(Caulimovirus) に属するウイルス等を挙げることができる。 Examples of viruses in which the fiber or fiber product of the present invention is effective include viruses belonging to the genus of simplex viruses such as herpes simplex virus type 1 (Herpes simplex I) and herpes simplex virus type 2 (Herpes simplex II); Viruses belonging to the genus Varicellovirus such as Varicella-zoster virus; viruses belonging to the genus lymphocryptovirus such as Epstein-Barr virus; vaccinia viruses ( Viruses belonging to the genus Orthopoxvirus, Vaccinia Subgroup, such as Vaccinia virus), Variola virus, Cowpox virus, Monkeypox virus; Coronaviridae, such as SARS virus ): Yellow fever virus, Japanese encephalitis virus (Japanese) encephalitis virus, hepatitis C virus, dengue fever virus, viruses belonging to the genus Flavivirus such as West Nile virus; bovine viral diarrhea virus, swine cholera virus, border disease virus Viruses belonging to the genus pesti virus such as; viruses belonging to the genus Aphthovirus such as foot-and-mouth disease virus; viruses belonging to the enterovirus genus such as poliovirus A virus belonging to the genus Hepatovirus (Hepatitis A virus) such as Hepatitis A virus; a virus belonging to the genus Rhinovirus such as Common cold virus; a ruby virus such as Rubella virus; Viruses belonging to the genus (Rubivirus); Alphaviruses such as Encephalitis virus (Alphavirus, Viruses belonging to Arbovirus group A); viruses belonging to the genus Hepevirus such as hepatitis E virus (Hepatitis E virus); viruses belonging to the genus Tobamovirus such as tobacco mosaic virus; Marburg virus Ebola virus; viruses belonging to the genus Lyssavirus, Rabies virus group such as Rabies virus; vesiculoviruses such as vesicular stomatitis virus Vesiculovirus, Vesicular stomatitis virus group Virus belonging to the genus Morbillivirus such as Measles virus; Virus belonging to the genus Rubulavirus such as Mumps virus; Sendai virus, etc. Virus belonging to the genus Respirovirus; Newcastle disease virus Virus belonging to the genus Avulavirus such as Newcastle disease virus; Virus belonging to the genus Pneumovirus, Respiratory syncytial virus group such as Respiratory syncytial virus; Human metapneumovirus Viruses belonging to the genus Metapneumovirus such as Metapneumovirus; viruses belonging to the genus Henipavirus such as Nipah virus; Orthomyki such as influenza viruses A, B, C (Influenza virus A, B, C) Viruses belonging to the genus Influenza virus; viruses belonging to the genus Bunyavirus, Bunyamwear subgroup such as Bunyamwera virus; belonging to the genus Hantaviruses such as Hantavirus Virus; Lymphocytic choriomeningitis vir us), viruses belonging to the genus Arenavirus, LCM virus group such as Lassa virus; lentiviruses such as human immunodeficiency virus (HIV); adult T-cell leukemia virus (Human T- Viruses belonging to the genus Oncovirus, Type C oncovirus group such as lymphotropic virus, Adult T cell leukemia virus; hepatitis B virus; caulimo such as cauliflower mosaic virus Examples include viruses belonging to the genus Caulimovirus.
本発明の方法で得られる繊維又は繊維製品は、顕著に優れた抗ウイルス作用を備えている。 The fiber or fiber product obtained by the method of the present invention has a remarkably excellent antiviral effect.
本発明の方法で得られる繊維又は繊維製品は、耐洗濯性に優れており、該繊維又は繊維製品を繰り返し洗濯しても実質的に低下しない。 The fiber or fiber product obtained by the method of the present invention has excellent washing resistance, and even when the fiber or fiber product is repeatedly washed, it does not substantially decrease.
以下に実施例及び比較例を掲げて、本発明をより一層明らかにする。 The present invention will be further clarified by the following examples and comparative examples.
実施例1
目付150g/m2の綿織物を精練し、漂白し、シルケット処理を行った。次いで、処理後の綿織物を、ポリオキシエチレン(ジメチルイミノ)エチレン(ジメチルイミノ)エチレンクロライド1.5重量%、メラミン樹脂(リケンレジンMM65S、三木理研工業製)1重量%及び触媒(リケンフィクサーRC−3、三木理研工業製)0.5重量%を含む水溶液に浸漬し、マングルで絞り(絞り率60%)、100℃で乾燥し、160℃で2分間熱処理を行った。熱処理後の綿織物を、以下「綿織物A」という。更に、綿織物Aを、ノニオン界面活性剤(商品名:ソフタノール90、日本触媒製)0.05重量%を含む水溶液を使用して40℃で5分間ソーピングを行い、次に5分間水洗することにより、綿織物を得た。ソーピング及び水洗処理して得られる本発明の綿織物を、以下「綿織物B」という。
Example 1
A cotton fabric having a basis weight of 150 g / m 2 was scoured, bleached, and mercerized. The treated cotton fabric was then treated with 1.5% by weight of polyoxyethylene (dimethylimino) ethylene (dimethylimino) ethylene chloride, 1% by weight of melamine resin (Riken Resin MM65S, manufactured by Miki Riken Kogyo) and catalyst (Rickenfixer RC-3). (Manufactured by Miki Riken Kogyo Co., Ltd.) It was immersed in an aqueous solution containing 0.5% by weight, drawn with a mangle (drawing ratio 60%), dried at 100 ° C., and heat-treated at 160 ° C. for 2 minutes. The cotton fabric after the heat treatment is hereinafter referred to as “cotton fabric A”. Further, cotton fabric A is soaped for 5 minutes at 40 ° C. using an aqueous solution containing 0.05% by weight of a nonionic surfactant (trade name: Softanol 90, manufactured by Nippon Shokubai), and then washed with water for 5 minutes. A cotton fabric was obtained. The cotton fabric of the present invention obtained by the soaping and washing treatment is hereinafter referred to as “cotton fabric B”.
綿織物Bを通常の洗濯条件下(洗濯方法:JIS L 0217 103法)に50回洗濯を繰り返した。50回洗濯を繰り返して得られる綿織物を、以下「綿織物C」という。 Cotton fabric B was repeatedly washed 50 times under normal washing conditions (washing method: JIS L 0217 103 method). The cotton fabric obtained by repeating washing 50 times is hereinafter referred to as “cotton fabric C”.
比較例1
目付150g/m2の綿織物を精練し、漂白し、シルケット処理を行った。次いで、処理後の綿織物を、ノニオン界面活性剤(商品名:ソフタノール90、日本触媒製)0.05重量%を含む水溶液を使用して40℃で5分間ソーピングを行い、次に5分間水洗することにより、綿織物を得た。
Comparative Example 1
A cotton fabric having a basis weight of 150 g / m 2 was scoured, bleached, and mercerized. Next, the treated cotton fabric is soaped at 40 ° C. for 5 minutes using an aqueous solution containing 0.05% by weight of a nonionic surfactant (trade name: Softanol 90, manufactured by Nippon Shokubai), and then washed with water for 5 minutes. As a result, a cotton fabric was obtained.
比較例2
目付150g/m2の綿織物を精練し、漂白し、シルケット処理を行った。次いで、処理後の綿織物を、メラミン樹脂(リケンレジンMM65S、三木理研工業製)1重量%及び触媒(リケンフィクサーRC−3、三木理研工業製)0.5重量%を含む水溶液に浸漬し、マングルで絞り(絞り率60%)、100℃で乾燥し、160℃で2分間熱処理を行った。更に、上記処理した綿織物を、ノニオン界面活性剤(商品名:ソフタノール90、日本触媒製)0.05重量%を含む水溶液を使用して40℃で5分間ソーピングを行い、次に5分間水洗することにより、綿織物を得た。
Comparative Example 2
A cotton fabric having a basis weight of 150 g / m 2 was scoured, bleached, and mercerized. Next, the treated cotton fabric was immersed in an aqueous solution containing 1% by weight of melamine resin (Riken Resin MM65S, manufactured by Miki Riken Kogyo) and 0.5% by weight of a catalyst (Riken Fixer RC-3, manufactured by Miki Riken Kogyo) with a mangle. Drawing (drawing ratio 60%), drying at 100 ° C., and heat treatment at 160 ° C. for 2 minutes. Further, the treated cotton fabric is soaped at 40 ° C. for 5 minutes using an aqueous solution containing 0.05% by weight of a nonionic surfactant (trade name: Softanol 90, manufactured by Nippon Shokubai), and then washed with water for 5 minutes. As a result, a cotton fabric was obtained.
比較例3
目付150g/m2の綿織物を精練し、漂白し、シルケット処理を行った。次いで、処理後の綿織物を、2−ピリジンチオール−ジンク−1−オキシド1重量%、メラミン樹脂(リケンレジンMM65S、三木理研工業製)1重量%及び触媒(リケンフィクサーRC−3、三木理研工業製)0.5重量%を含む水溶液に浸漬し、マングルで絞り(絞り率60%)、100℃で乾燥し、160℃で2分間熱処理を行った。更に、熱処理後の綿織物を、ノニオン界面活性剤(商品名:ソフタノール90、日本触媒製)0.05重量%を含む水溶液を使用して40℃で5分間ソーピングを行い、次に5分間水洗することにより、綿織物を得た。
Comparative Example 3
A cotton fabric having a basis weight of 150 g / m 2 was scoured, bleached, and mercerized. The treated cotton fabric was then treated with 1% by weight of 2-pyridinethiol-zinc-1-oxide, 1% by weight of melamine resin (Riken Resin MM65S, manufactured by Miki Riken Kogyo) and catalyst (Riken Fixer RC-3, manufactured by Miki Riken Kogyo). It was immersed in an aqueous solution containing 0.5% by weight, drawn with a mangle (drawing rate 60%), dried at 100 ° C., and heat-treated at 160 ° C. for 2 minutes. Furthermore, the cotton fabric after heat treatment is soaped at 40 ° C. for 5 minutes using an aqueous solution containing 0.05% by weight of a nonionic surfactant (trade name: Softanol 90, manufactured by Nippon Shokubai), and then washed with water for 5 minutes. As a result, a cotton fabric was obtained.
比較例4
目付150g/m2の綿織物を精練し、漂白し、シルケット処理を行った。次いで、処理後の綿織物を、酸化亜鉛1重量%及びアクリル酸樹脂(商品名:MAR、松本油脂製薬(株)製)2重量%を含む水溶液に浸漬し、マングルで絞り(絞り率60%)、100℃で乾燥し、160℃で2分間熱処理を行った。更に、熱処理後の綿織物を、ノニオン界面活性剤(商品名:ソフタノール90、日本触媒製)0.05重量%を含む水溶液を使用して40℃で5分間ソーピングを行い、次に5分間水洗することにより、綿織物を得た。
Comparative Example 4
A cotton fabric having a basis weight of 150 g / m 2 was scoured, bleached, and mercerized. Next, the treated cotton fabric is dipped in an aqueous solution containing 1% by weight of zinc oxide and 2% by weight of acrylic resin (trade name: MAR, manufactured by Matsumoto Yushi Seiyaku Co., Ltd.) and squeezed with a mangle (squeezing rate 60%). , Dried at 100 ° C. and heat-treated at 160 ° C. for 2 minutes. Furthermore, the cotton fabric after heat treatment is soaped at 40 ° C. for 5 minutes using an aqueous solution containing 0.05% by weight of a nonionic surfactant (trade name: Softanol 90, manufactured by Nippon Shokubai), and then washed with water for 5 minutes. As a result, a cotton fabric was obtained.
試験例1(抗ウイルス活性の確認試験)
(1)ウイルス液の調製
鳥インフルエンザウイルス(A/budgeringer/Aichi/1/77(H3N8))を発育鶏卵の尿膜腔内に接種し、35℃で3日間培養後に、尿膜腔液を採取し、ウイルス液として使用した。
Test Example 1 (Confirmation test of antiviral activity)
(1) Preparation of virus solution Avian influenza virus (A / budgeringer / Aichi / 1/77 (H3N8)) is inoculated into the allantoic cavity of growing eggs and cultured at 35 ° C for 3 days. And used as a virus solution.
(2)試験に使用した綿織物
実施例1で得られた綿織物A、綿織物B及び綿織物C(各綿織物の大きさは18mm×18mm)を121℃のオートクレーブ中に20分間入れ、次に乾燥させた。3枚の綿織物Aを1組とし、2組(計6枚)を試験に使用した。また、上記と同様に、3枚の綿織物Bを1組、3枚の綿織物Cを1組とし、これら各々2組を試験に使用した。更に、比較のために、未処理の綿織物、比較例1〜4で得られた綿織物及び比較例1〜4で得られた綿織物を50回洗濯した綿織物についても、上記と同様にして試験に使用した。
(2) Cotton fabric used in the test Cotton fabric A, cotton fabric B, and cotton fabric C (the size of each cotton fabric is 18 mm × 18 mm) obtained in Example 1 were placed in an autoclave at 121 ° C. for 20 minutes and then dried. . Three sets of cotton fabric A were used as one set, and two sets (6 sheets in total) were used for the test. Further, similarly to the above, one set of three cotton fabrics B and one set of three cotton fabrics C were used, and two sets of each were used in the test. Further, for comparison, an untreated cotton fabric, the cotton fabric obtained in Comparative Examples 1 to 4 and the cotton fabric obtained by washing the cotton fabric obtained in Comparative Examples 1 to 4 were used in the test in the same manner as described above. did.
(3)感作方法
各々の綿織物1組(3枚)をマイクロチューブに入れ、ウイルス液0.1mlを浸み込ませ、室温で10分間感作させた。感作後、直ちにマイクロチューブを1分間当たり5000回転の速度で30秒間回転させ、各々の綿織物から感作ウイルス液を回収した。
(3) Sensitization method Each pair of cotton fabrics (3 sheets) was placed in a microtube, 0.1 ml of the virus solution was immersed, and sensitized at room temperature for 10 minutes. Immediately after the sensitization, the microtube was rotated at a speed of 5000 revolutions per minute for 30 seconds, and the sensitized virus solution was collected from each cotton fabric.
(4)ウイルス感染価の測定
回収した各感作ウイルス液を、直ちにPBSを用いて10倍段階希釈し、48穴マイクロプレートで培養した初代鶏腎細胞に接種し(0.1ml/ウエル、2ウエル)、37℃で1時間保持し、感作ウイルスを初代鶏腎細胞に吸着させた後、増殖培地(ダルベッコ変法イーグル培地に、10%牛血清、10%トリプトース・ホスフェート・ブロスを加えたもの)0.2mlを加え、37℃で培養し、翌日増殖培地を交換し、更に6日間(計7日間)培養を行った。
(4) Measurement of virus infectivity titer Each sensitized virus solution collected was immediately diluted 10-fold with PBS and inoculated into primary chicken kidney cells cultured on a 48-well microplate (0.1 ml / well, 2 Well), maintained at 37 ° C. for 1 hour, and adsorbed the sensitized virus to primary chicken kidney cells, and then added growth medium (Dulbecco's modified Eagle medium with 10% bovine serum, 10% tryptose phosphate broth) 1) 0.2 ml was added, cultured at 37 ° C., the growth medium was changed the next day, and further cultured for 6 days (7 days in total).
ウイルス増殖の有無は、細胞変性と培養液の赤血球凝集性で判定し、Reed and Muench の方法に従って、ウイルス感染価を算出した。 The presence or absence of virus growth was determined by cell degeneration and hemagglutination of the culture solution, and the virus infectivity titer was calculated according to the method of Reed and Muench.
(5)試験結果
綿織物B及び綿織物Cで感作させた後に回収されたウイルス液中に残存するウイルス感染価は、いずれも検出限界以下10≦0.5であり、洗濯を50回繰り返してもその抗ウイルス効果が低下しないことが確認できた。
(5) Test results The virus infectivity remaining in the virus solution recovered after sensitization with cotton fabric B and cotton fabric C is 10 ≦ 0.5 below the detection limit. It was confirmed that the virus effect did not decrease.
一方、綿織物Aで感作させた後に回収されたウイルス液中に残存するウイルス感染価は、未処理の綿織物と同様に105.0/0.1mlであり、抗ウイルス効果を確認できなかった。比較例1〜4で得られた綿織物及び比較例1〜4で得られた綿織物を50回洗濯した綿織物についても、未処理の綿織物と同様に抗ウイルス効果を確認できなかった。 On the other hand, the virus infectivity remaining in the virus solution collected after sensitization with cotton fabric A was 10 5.0 /0.1 ml as in the case of untreated cotton fabric, and the antiviral effect could not be confirmed. For the cotton fabric obtained by washing the cotton fabric obtained in Comparative Examples 1 to 4 and the cotton fabric obtained in Comparative Examples 1 to 4 50 times, the antiviral effect could not be confirmed as in the case of the untreated cotton fabric.
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