WO1996018764A1 - Procede de finition anti-salissure pour fibre de cellulose et produit de finition anti-salissure - Google Patents

Procede de finition anti-salissure pour fibre de cellulose et produit de finition anti-salissure Download PDF

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Publication number
WO1996018764A1
WO1996018764A1 PCT/JP1995/002559 JP9502559W WO9618764A1 WO 1996018764 A1 WO1996018764 A1 WO 1996018764A1 JP 9502559 W JP9502559 W JP 9502559W WO 9618764 A1 WO9618764 A1 WO 9618764A1
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WO
WIPO (PCT)
Prior art keywords
cellulose
copolymer
weight
group
fiber
Prior art date
Application number
PCT/JP1995/002559
Other languages
English (en)
French (fr)
Japanese (ja)
Inventor
Motonobu Kubo
Takashi Enomoto
Original Assignee
Daikin Industries, Ltd.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Daikin Industries, Ltd. filed Critical Daikin Industries, Ltd.
Priority to US08/849,842 priority Critical patent/US5879408A/en
Publication of WO1996018764A1 publication Critical patent/WO1996018764A1/ja

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Classifications

    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
    • D06M13/184—Carboxylic acids; Anhydrides, halides or salts thereof
    • D06M13/188—Monocarboxylic acids; Anhydrides, halides or salts thereof
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
    • D06M13/184—Carboxylic acids; Anhydrides, halides or salts thereof
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
    • D06M13/184—Carboxylic acids; Anhydrides, halides or salts thereof
    • D06M13/192—Polycarboxylic acids; Anhydrides, halides or salts thereof
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/263—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/263—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof
    • D06M15/277—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof containing fluorine
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2101/00—Chemical constitution of the fibres, threads, yarns, fabrics or fibrous goods made from such materials, to be treated
    • D06M2101/02—Natural fibres, other than mineral fibres
    • D06M2101/04—Vegetal fibres
    • D06M2101/06—Vegetal fibres cellulosic
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
    • Y10T428/2913—Rod, strand, filament or fiber
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
    • Y10T428/2913—Rod, strand, filament or fiber
    • Y10T428/2915—Rod, strand, filament or fiber including textile, cloth or fabric
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
    • Y10T442/20—Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
    • Y10T442/2279—Coating or impregnation improves soil repellency, soil release, or anti- soil redeposition qualities of fabric
    • Y10T442/2287—Fluorocarbon containing
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
    • Y10T442/20—Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
    • Y10T442/2279—Coating or impregnation improves soil repellency, soil release, or anti- soil redeposition qualities of fabric
    • Y10T442/2295—Linear polyether group chain containing

Definitions

  • the present invention relates to an antifouling method and an antifouling product for cellulose fibers.
  • Conventional technology
  • Cellulose fibers and fiber products in the present specification mean cotton, hemp, viscose rayon, cuprammonium rayon, wood pulp, and fabrics, nonwoven fabrics, sheets, and the like manufactured using these.
  • An object of the present invention is to provide an antifouling method and an antifouling product for cellulose fibers themselves.
  • X is -CH (CH S ) _CH 2 -or-CH 2 -CH (CH 3 )-
  • Y is -CH 2 CH 2-
  • R is a hydrogen atom or a methyl group
  • R 2 is a hydrogen atom Or, an alkyl group having 1 to 8 carbon atoms
  • m and n each represent an integer of 0 to 50.
  • m + n is 1 to 70.
  • the object of the present invention is also achieved by an antifouling product obtained by the above antifouling processing method.
  • the portion formed by X0 and YO may be buccal or random.
  • the hydroxyl group of the cellulose fiber is
  • the degree of esterification is preferably 0.01 to 1.5, particularly preferably 0.03 to 1.3, when represented by the degree of substitution (DS) defined below.
  • DS degree of substitution
  • esterifying agents include carboxylic acids, carboxylic anhydrides, carboxylic acid chlorides and ketene.
  • the esterification reaction can be carried out in a liquid phase using a solvent and / or (ii) a medium as required, but a system in which the produced cellulose ester does not dissolve, in other words, while maintaining the male fiber state It is important to select a system that will react.
  • the reaction can be performed in a gas phase.
  • esterification catalyst a commonly used catalyst, for example, sulfuric acid, perchloric acid, methanesulfonic acid, aromatic sulfonic acid, zinc chloride, sodium hydroxide, pyridine and the like are used.
  • the reaction temperature in the nostillation reaction is usually room temperature to 120, preferably room temperature to 80 ° C.
  • the reaction time is chosen such that the above-mentioned degree of substitution is achieved.
  • the copolymer used in the second step contains a repeating unit derived from a fluoroalkyl group-containing polymerizable compound and a repeating unit derived from the unsaturated compound represented by the above general formula.
  • the fluoroalkyl group-containing polymerizable compound used in the present invention has, for example, the following formula:
  • R f— A 1 — 0 C ⁇ -1 CA 2 CH 2 [Wherein, R f is a fluoroalkyl group, A is [ ⁇ 2 ), —,
  • R is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, 1 is 1 to 10
  • a 2 is a hydrogen atom or a methyl group.
  • Rf is preferably a perfluoroalkyl group.
  • fluoroalkyl group-containing polymerizable compound Preferred examples of the fluoroalkyl group-containing polymerizable compound are as follows.
  • n and m are each 1 to 25 is preferable. These compounds may be used alone or in combination of two or more.
  • the copolymer used in the present invention contains a fluoroalkyl group-containing polymerizable compound in an amount of usually 5 to 95% by weight, preferably 30 to 80% by weight, and more preferably 40 to 70% by weight, based on the total weight fi.
  • a fluoroalkyl group-containing polymerizable compound in an amount of usually 5 to 95% by weight, preferably 30 to 80% by weight, and more preferably 40 to 70% by weight, based on the total weight fi.
  • the proportion of the fluoroalkyl group-containing polymerizable compound exceeds 95% by weight, the soil release property becomes insufficient. On the other hand, if it is less than 5%, the oil repellency is insufficient.
  • the molecular weight of the copolymer is usually 1000-100000 (measured by gel permeation chromatography (GPC)).
  • a copolymerizable monomer such as a crosslinking monomer may be added.
  • Ds alkyl ester of acrylic acid or methacrylic acid, styrene, benzyl (meth) acrylate, vinyl alkyl ketone, vinyl alkyl ether, isoprene, Butage And chlorobrene can also be copolymerized.
  • These third monomers are generally used in an amount of 0 to 40% by weight, preferably 0 to 25% by weight, more preferably 0 to 15% by weight, based on the total weight of the copolymer.
  • Suitable combinations of monomers include:
  • a water repellent and oil repellent for example, TG-521 (manufactured by Daikin Industries, Ltd.)
  • the weight ratio of the copolymer to the water / oil repellent active ingredient is preferably 10: 0 to 10:50.
  • various polymerization reaction methods and conditions can be arbitrarily selected, such as bulk polymerization, solution polymerization, suspension polymerization, emulsification base, radiation polymerization, and the like. Any of various polymerization systems can be employed.
  • a method in which a mixture of compounds to be copolymerized is emulsified in water in the presence of a surfactant and copolymerized with stirring can be adopted.
  • the polymerization initiator for the reaction system various peroxide, azo or persulfuric acid initiators can be used.
  • Polyalkylene glycol acrylate or methacrylate works as a surfactant, so there is no need to use a surfactant, but various anionic, picking or nonionic emulsifiers are optional. May be added.
  • the raw material monomer is dissolved in a suitable solvent, and solution polymerization is carried out by the action of a polymerization initiator (peroxide, azo compound or ionizing radiation soluble in the organic solvent used). You can also.
  • a polymerization initiator peroxide, azo compound or ionizing radiation soluble in the organic solvent used. You can also.
  • Suitable solvents for solution polymerization are acetone, methyl ethyl ketone, isopropanol, ethyl sorb, propylene glycol monomethyl ether, dibu pyrene glycol monomethyl ether, diglyme, triglyme and the like.
  • the copolymer thus obtained can be prepared into an antifouling agent in any form, such as a milk crush, a solvent solution, or an aerosol, according to a conventional method.
  • the most appropriate method for applying the antifouling agent containing the copolymer as an active ingredient may be selected according to the type of the object to be treated, the purpose of use, the preparation form of the antifouling agent, and the like.
  • the substance may be attached to the surface of the object to be treated by a known method such as spraying, dipping, or coating, and then dried. If necessary, curing is performed.
  • an antistatic agent, a flame retardant, a screen inhibitor, and other polymers may be added to the copolymer of the present invention.
  • the amount of the copolymer to be applied to the cellulose fiber in which the hydroxyl group is esterified by the method of the present invention is usually 0.1 to 1 part by weight based on 100 parts by weight of the material to be treated (cellulose fiber). It is 0 times * part.
  • the water repellency was measured by the spray method of JI SL-1092 (see Table 1 below).
  • the oil repellency was determined by placing the test solution 0.051 shown in Table 2 below on a test cloth and measuring the permeation state after 30 seconds.
  • Judgment (AAT CC-TM118-1983) Table 1
  • the test for soil release is performed as follows. Spread the test cloth on a horizontal layer of paper. Drop the waste motor oil (0.1 ⁇ 1), cover it with a polyethylene sheet, place a 2 kg weight, and after 60 seconds, remove the weight and weight. Remove it, leave it at room temperature for 1 hour, wash it in an electric washing machine for 10 minutes with 60 g of detergent (sparsab: trade name), bath rates of 35 and 40, then rinse and air-dry. The condition of the dried test cloth shall be indicated using the applicable judgment in Table 3.
  • the bound acetic acid content was determined according to the method of Frank Howlett [Journal of Textile Institut (J. Text. Inst.) 3_5 T1 (1944) 3, 9.2% Met. That is, the S conversion (DS) was 0.266.
  • the S-degree of exchange (DS) after acetylation was specifically determined as follows:
  • Cotton cloth (30CIDX3 Ocn is immersed in 0.1N sulfuric acid at room temperature for 10 minutes, squeezed 3 times to evaporate water until the water content becomes 50%, and then steamed with acetic anhydride vapor in a desiccator. After the completion of the reaction, the degree of substitution was determined to be 0.247 by the same treatment as in Production Example 1.
  • the amount of propionic acid was determined as follows.
  • the degree of substitution of the obtained propionylated cotton was 0.18.
  • the cotton cloth was washed three times with methanol and acetone alternately, and then acetone-extracted with a Soxhlet extractor for 24 hours. After the acetone was removed under reduced pressure until the weight became constant, it was precisely weighed. The degree of substitution obtained by assuming the weight increase before and after the reaction to be due to palmityl esterification was 0.046.
  • CH 2 C (CH 3 ) COO-CH 2 -CH-CH 2
  • the solution was added, and the copolymerization reaction was carried out by stirring the mixture under a stream of room temperature with 6 (TC for 10 hours. According to gas chromatography, the conversion of the copolymerization reaction was 99% or more. From this conversion, the obtained total It was found that the proportion of each monomer unit in the polymer almost coincided with the proportion of the charged monomer, and the obtained dispersion contained 20% of a copolymer solid.
  • CoH 1 9 '> -0- (CH 2 CH 2 0) 2o-H 1 Og was placed in a glass four-quarter flask equipped with a mercury thermometer and a polytetrafluoroethylene crescent-shaped blade stirrer, and sufficiently emulsified and dispersed by stirring under a nitrogen stream. . After blowing nitrogen for about 1 hour, the copolymerization reaction was carried out at 60 ° C for 20 hours with gentle stirring. The conversion rate of the copolymerization reaction by gas chromatography was 99.6% (based on the polymerizable compound having a fluorine-containing alkyl group), and the obtained stable emulsified latex contained 22.5% of a copolymer solid. .
  • the copolymer dispersion liquid prepared in Production Example 6 was diluted with water so that the copolymer solid content was 0.5% by weight.
  • the acetylated cotton obtained in Production Example 1 was immersed, squeezed with a lip, and the pet pickup was set to 70%. Then, after drying at 100 for 3 minutes, treatment was further performed at 160 for 1 minute.
  • the cloth treated in this way has a water repellency of 7, an oil repellency ⁇ 7, and a dirt removal performance of 5.
  • Cotton not subjected to the treatment in the first step was treated in the same manner as in Example 1 using the copolymer dispersions obtained in Production Examples 6 to 10.
  • Table 4 shows the evaluation results.
  • Example 9 Production Example 3 6 7 0 6 5
  • Example 10 7 5 0 6 5
  • Example 11 ⁇ 8 5 0 5 5
  • Example 12 Production Example 4 6 7 0 6 5
  • Example 13 ⁇ 7 7 0 6 5
  • Example 14 8 5 0 5 ⁇
  • Example 15 Production Example 5 6 7 0 6 0
  • Example 16 ft 7 7 0 6 ⁇
  • Example 17 8 7 0 6 ⁇

Landscapes

  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
PCT/JP1995/002559 1994-12-15 1995-12-14 Procede de finition anti-salissure pour fibre de cellulose et produit de finition anti-salissure WO1996018764A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US08/849,842 US5879408A (en) 1994-12-15 1995-12-14 Method of stainproofing cellulose fibers and stainproofed product

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP6/311635 1994-12-15
JP31163594 1994-12-15

Publications (1)

Publication Number Publication Date
WO1996018764A1 true WO1996018764A1 (fr) 1996-06-20

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ID=18019647

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Application Number Title Priority Date Filing Date
PCT/JP1995/002559 WO1996018764A1 (fr) 1994-12-15 1995-12-14 Procede de finition anti-salissure pour fibre de cellulose et produit de finition anti-salissure

Country Status (4)

Country Link
US (1) US5879408A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
CN (1) CN1074482C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
TW (1) TW289059B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
WO (1) WO1996018764A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013058244A1 (ja) * 2011-10-17 2013-04-25 三菱化学株式会社 化学修飾セルロース不織布の製造方法および化学修飾セルロース不織布、並びに、これを用いたセルロース繊維樹脂複合材料およびその製造方法
JP2019116705A (ja) * 2017-12-27 2019-07-18 東京応化工業株式会社 変性セルロース繊維、分散液、多孔質膜、蓄電素子、及び多孔質膜の製造方法

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6488718B1 (en) * 1998-11-13 2002-12-03 Cotton Incorporated Methods for reducing the flammability of cellulosic substrates
US6491727B1 (en) * 1999-06-09 2002-12-10 Cotton Incorporated Methods for reducing the flammability of cellulosic substrates
US20070167618A1 (en) * 2006-01-13 2007-07-19 Celanese Acetate, Llc Manufacture of cellulose esters: recycle of caustic and/or acid from pre-treatment of pulp

Citations (2)

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Publication number Priority date Publication date Assignee Title
JPS5296298A (en) * 1976-02-03 1977-08-12 Santo Tekkosho Kk Method and apparatus for improving quality of cellulosic fiber containing cloth
JPH0468006A (ja) * 1990-07-09 1992-03-03 Daikin Ind Ltd 新規共重合体および防汚加工剤

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JPH02277887A (ja) * 1989-04-14 1990-11-14 Toray Ind Inc 防汚性布帛
JP3132126B2 (ja) * 1992-02-25 2001-02-05 ソニー株式会社 半導体装置およびその製造方法
JP3300424B2 (ja) * 1992-10-07 2002-07-08 ダイキン工業株式会社 新規共重合体および防汚加工剤
JP4068006B2 (ja) * 2003-05-07 2008-03-26 信越化学工業株式会社 サーマルフロー工程を用いた微細なコンタクトホール形成方法

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Publication number Priority date Publication date Assignee Title
JPS5296298A (en) * 1976-02-03 1977-08-12 Santo Tekkosho Kk Method and apparatus for improving quality of cellulosic fiber containing cloth
JPH0468006A (ja) * 1990-07-09 1992-03-03 Daikin Ind Ltd 新規共重合体および防汚加工剤

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013058244A1 (ja) * 2011-10-17 2013-04-25 三菱化学株式会社 化学修飾セルロース不織布の製造方法および化学修飾セルロース不織布、並びに、これを用いたセルロース繊維樹脂複合材料およびその製造方法
JP2019116705A (ja) * 2017-12-27 2019-07-18 東京応化工業株式会社 変性セルロース繊維、分散液、多孔質膜、蓄電素子、及び多孔質膜の製造方法
JP7118639B2 (ja) 2017-12-27 2022-08-16 東京応化工業株式会社 変性セルロース繊維、分散液、多孔質膜、蓄電素子、及び多孔質膜の製造方法

Also Published As

Publication number Publication date
CN1074482C (zh) 2001-11-07
US5879408A (en) 1999-03-09
TW289059B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) 1996-10-21
CN1175293A (zh) 1998-03-04

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