JPWO2018180538A1 - 布帛用撥水処理剤及び布帛 - Google Patents
布帛用撥水処理剤及び布帛 Download PDFInfo
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- JPWO2018180538A1 JPWO2018180538A1 JP2018560691A JP2018560691A JPWO2018180538A1 JP WO2018180538 A1 JPWO2018180538 A1 JP WO2018180538A1 JP 2018560691 A JP2018560691 A JP 2018560691A JP 2018560691 A JP2018560691 A JP 2018560691A JP WO2018180538 A1 JPWO2018180538 A1 JP WO2018180538A1
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- fabric
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- water repellent
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- 239000012760 heat stabilizer Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- DWYKRMTVNUXSIM-UHFFFAOYSA-N hexane-1,6-diol;prop-2-enoic acid Chemical compound OC(=O)C=C.OCCCCCCO DWYKRMTVNUXSIM-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000005453 ketone based solvent Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- HNEGQIOMVPPMNR-NSCUHMNNSA-N mesaconic acid Chemical compound OC(=O)C(/C)=C/C(O)=O HNEGQIOMVPPMNR-NSCUHMNNSA-N 0.000 description 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- HNEGQIOMVPPMNR-UHFFFAOYSA-N methylfumaric acid Natural products OC(=O)C(C)=CC(O)=O HNEGQIOMVPPMNR-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229920006120 non-fluorinated polymer Polymers 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 239000013500 performance material Substances 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920003216 poly(methylphenylsiloxane) Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- WYKYCHHWIJXDAO-UHFFFAOYSA-N tert-butyl 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOC(C)(C)C WYKYCHHWIJXDAO-UHFFFAOYSA-N 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- GTZCVFVGUGFEME-UHFFFAOYSA-N trans-aconitic acid Natural products OC(=O)CC(C(O)=O)=CC(O)=O GTZCVFVGUGFEME-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/12—Hydrolysis
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- C09K3/18—Materials not provided for elsewhere for application to surfaces to minimize adherence of ice, mist or water thereto; Thawing or antifreeze materials for application to surfaces
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Combustion & Propulsion (AREA)
- Materials Engineering (AREA)
- Textile Engineering (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Materials Applied To Surfaces To Minimize Adherence Of Mist Or Water (AREA)
Abstract
Description
測定装置:高速GPC装置(東ソー株式会社製「HLC−8220GPC」)
カラム:東ソー株式会社製の下記のカラムを直列に接続して使用した。
「TSKgel G5000」(7.8mmI.D.×30cm)×1本
「TSKgel G4000」(7.8mmI.D.×30cm)×1本
「TSKgel G3000」(7.8mmI.D.×30cm)×1本
「TSKgel G2000」(7.8mmI.D.×30cm)×1本
検出器:RI(示差屈折計)
カラム温度:40℃
溶離液:テトラヒドロフラン(THF)
流速:1.0mL/分
注入量:100μL(試料濃度4mg/mLのテトラヒドロフラン溶液)
標準試料:下記の単分散ポリスチレンを用いて検量線を作成した。
東ソー株式会社製「TSKgel 標準ポリスチレン A−500」
東ソー株式会社製「TSKgel 標準ポリスチレン A−1000」
東ソー株式会社製「TSKgel 標準ポリスチレン A−2500」
東ソー株式会社製「TSKgel 標準ポリスチレン A−5000」
東ソー株式会社製「TSKgel 標準ポリスチレン F−1」
東ソー株式会社製「TSKgel 標準ポリスチレン F−2」
東ソー株式会社製「TSKgel 標準ポリスチレン F−4」
東ソー株式会社製「TSKgel 標準ポリスチレン F−10」
東ソー株式会社製「TSKgel 標準ポリスチレン F−20」
東ソー株式会社製「TSKgel 標準ポリスチレン F−40」
東ソー株式会社製「TSKgel 標準ポリスチレン F−80」
東ソー株式会社製「TSKgel 標準ポリスチレン F−128」
東ソー株式会社製「TSKgel 標準ポリスチレン F−288」
東ソー株式会社製「TSKgel 標準ポリスチレン F−550」
攪拌機、還流冷却管、温度計および窒素吹き込み管を備えた4つ口フラスコに酢酸n−ブチル95質量部を仕込み120℃に昇温し、これに無水マレイン酸61.5質量部、ラウリルメタクリレート184.5質量部、酢酸n−ブチル75質量部、t−ブチルパーオキシベンゾエート3質量部の溶解混合物を2時間かけて滴下し、120〜125℃にて反応を行った。その後、120℃で2時間ホールドした後、温度を90℃に下げ、25質量%アンモニア水85.3質量部、イオン交換水1700質量部を添加し、中和、水溶解を行った。温度を90℃に保ち、フラスコ内を減圧(0.080〜0.095MPa)しながら、酢酸n−ブチルを脱溶剤した。脱溶剤後、冷却し、イオン交換水を添加することにより、不揮発分18質量%の布帛用撥水処理剤(1)を得た。この布帛用撥水処理剤(1)中のアクリル樹脂(A−1)の重量平均分子量は50,000であった。
攪拌機、還流冷却管、温度計および窒素吹き込み管を備えた4つ口フラスコに酢酸n−ブチル95質量部を仕込み120℃に昇温し、これに無水マレイン酸86.1質量部、シクロヘキシルメタクリレート159.9質量部、酢酸n−ブチル75質量部、t−ブチルパーオキシベンゾエート3質量部の溶解混合物を2時間かけて滴下し、120〜125℃にて反応を行った。その後、120℃で2時間ホールドした後、温度を90℃に下げ、25質量%アンモニア水119.4質量部、イオン交換水1700質量部を添加し、中和、水溶解を行った。温度を90℃に保ち、フラスコ内を減圧(0.080〜0.095MPa)しながら、酢酸n−ブチルを脱溶剤した。脱溶剤後、冷却し、イオン交換水を添加することにより、不揮発分18質量%の布帛用撥水処理剤(2)を得た。この布帛用撥水処理剤(2)中のアクリル樹脂(A−2)の重量平均分子量は55,000であった。
上記で得た布帛用撥水処理剤(2)100質量部に、シリコーンオイル(モメンティブ・パフォーマンス・マテリアルズ・ジャパン製「TSF451−100」)18質量部を添加し、均一になるまで攪拌を行い、布帛用撥水処理剤(3)を得た。
攪拌機、還流冷却管、温度計および窒素吹き込み管を備えた4つ口フラスコにステアリルアクリレート115.2質量部、イオン交換水240質量部、トリプロピレングリコール33質量部、ステアリン酸ジメチルアミノプロピルアミド6.08質量部、ポリオキシエチレンイソトリデシルエーテル(オキシエチレンの繰り返し単位数18)5.43質量部、ポリオキシエチレンイソトリデシルエーテル(オキシエチレンの繰り返し単位数3)1.71質量部、酢酸2.4質量部を仕込み、撹拌下に60℃で15分間、超音波で乳化分散させた。反応フラスコ内を窒素置換後、ラウリルメルカプタン0.24質量部、2,2−アゾビス(2−アミジノプロパン)二塩酸塩0.48質量部、及び水9質量部の溶液を添加し、60℃で5時間反応させることにより、不揮発分30質量%の布帛用撥水処理剤(R1)を得た。
攪拌機、還流冷却管、温度計および窒素吹き込み管を備えた4つ口フラスコに酢酸n−ブチル95質量部を仕込み120℃に昇温し、これに無水マレイン酸98.4質量部、n−ブチルメタクリレート147.6質量部、酢酸n−ブチル75質量部、t−ブチルパーオキシベンゾエート3質量部の溶解混合物を2時間かけて滴下し、120〜125℃にて反応を行った。その後、120℃で2時間ホールドした後、温度を90℃に下げ、25質量%アンモニア水136.5質量部、イオン交換水1700質量部を添加し、中和、水溶解を行った。温度を90℃に保ち、フラスコ内を減圧(0.080〜0.095MPa)しながら、酢酸n−ブチルを脱溶剤した。脱溶剤後、冷却し、イオン交換水を添加することにより、不揮発分25質量%の布帛用撥水処理剤(1)を得た。この布帛用撥水処理剤(R2)中のアクリル樹脂(RA−2)の重量平均分子量は50,000であった。
上記で得られた布帛用撥水処理剤をイオン交換水で不揮発分1%に希釈し、マングル塗工機にて基布(T/C)に乾燥後0.5g/m2の目付け量にて塗工し、120℃で5分間、さらに150℃で5分間乾燥し、撥水処理基材を得た。
上記で得た撥水処理基材を、JIS L1092の6.2.1C法に準拠して、洗濯処理を繰り返し30回行った。洗濯処理前後の各撥水処理基材について、JIS L1092のはっ水度試験(スプレー試験)を実施し、下記の基準により、撥水性(耐洗濯性)を評価した。
◎:4級以上
○:3級
△:2級
×:1級
Claims (4)
- 炭素原子数が6〜24のアルキル基を有する(メタ)アクリル酸エステル(a1)及び(無水)マレイン酸(a2)を必須原料とするアクリル樹脂(A)と、塩基性化合物(B)と、水性媒体(C)とを含有することを特徴とする布帛用撥水処理剤。
- 前記アクリル樹脂(A)の原料である単量体成分中の前記(メタ)アクリル酸エステル(a1)が45〜95質量%の範囲であり、前記(無水)マレイン酸(a2)が5〜55質量%の範囲である請求項1記載の布帛用撥水処理剤。
- 前記アクリル樹脂(A)の重量平均分子量が5,000〜150,000である請求項1又は2記載の布帛用撥水処理剤。
- 請求項1〜3いずれか1項記載の布帛用撥水処理剤で処理されたことを特徴とする布帛。
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JPS4920277B1 (ja) * | 1970-10-19 | 1974-05-23 | ||
JP2006328624A (ja) * | 2005-04-28 | 2006-12-07 | Nicca Chemical Co Ltd | 撥水剤、撥水加工方法及び撥水性繊維製品 |
JP2015120893A (ja) * | 2013-11-22 | 2015-07-02 | ダイキン工業株式会社 | 水系エマルション表面処理剤 |
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JPS4920277B1 (ja) * | 1970-10-19 | 1974-05-23 | ||
JP2006328624A (ja) * | 2005-04-28 | 2006-12-07 | Nicca Chemical Co Ltd | 撥水剤、撥水加工方法及び撥水性繊維製品 |
JP2015120893A (ja) * | 2013-11-22 | 2015-07-02 | ダイキン工業株式会社 | 水系エマルション表面処理剤 |
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