JPWO2018100930A1 - 水性樹脂組成物、及び、繊維積層体 - Google Patents
水性樹脂組成物、及び、繊維積層体 Download PDFInfo
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- JPWO2018100930A1 JPWO2018100930A1 JP2018521668A JP2018521668A JPWO2018100930A1 JP WO2018100930 A1 JPWO2018100930 A1 JP WO2018100930A1 JP 2018521668 A JP2018521668 A JP 2018521668A JP 2018521668 A JP2018521668 A JP 2018521668A JP WO2018100930 A1 JPWO2018100930 A1 JP WO2018100930A1
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- resin composition
- urethane resin
- mass
- aqueous resin
- aqueous
- Prior art date
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- XFSBVAOIAHNAPC-WSORPINJSA-N acetylbenzoylaconine Chemical compound O([C@H]1[C@]2(O)C[C@H]3C45[C@@H]6[C@@H]([C@@]([C@H]31)(OC(C)=O)[C@@H](O)[C@@H]2OC)[C@H](OC)C4[C@]([C@@H](C[C@H]5OC)O)(COC)CN6CC)C(=O)C1=CC=CC=C1 XFSBVAOIAHNAPC-WSORPINJSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000012790 adhesive layer Substances 0.000 description 1
- 239000005456 alcohol based solvent Substances 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
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- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical group C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
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- 238000011088 calibration curve Methods 0.000 description 1
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- 238000013329 compounding Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- GEQHKFFSPGPGLN-UHFFFAOYSA-N cyclohexane-1,3-diamine Chemical compound NC1CCCC(N)C1 GEQHKFFSPGPGLN-UHFFFAOYSA-N 0.000 description 1
- VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical compound NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 description 1
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- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 235000013681 dietary sucrose Nutrition 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- PJMICNUGBHGMKQ-UHFFFAOYSA-N ethane-1,1,2-triamine Chemical compound NCC(N)N PJMICNUGBHGMKQ-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 235000019256 formaldehyde Nutrition 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000011487 hemp Substances 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000005453 ketone based solvent Substances 0.000 description 1
- 238000009940 knitting Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- AYLRODJJLADBOB-QMMMGPOBSA-N methyl (2s)-2,6-diisocyanatohexanoate Chemical compound COC(=O)[C@@H](N=C=O)CCCCN=C=O AYLRODJJLADBOB-QMMMGPOBSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 239000012875 nonionic emulsifier Substances 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000002918 oxazolines Chemical class 0.000 description 1
- 229920000747 poly(lactic acid) Polymers 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000004626 polylactic acid Substances 0.000 description 1
- 229920000259 polyoxyethylene lauryl ether Polymers 0.000 description 1
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 description 1
- 229920006389 polyphenyl polymer Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/40—Layered products comprising a layer of synthetic resin comprising polyurethanes
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B5/00—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts
- B32B5/22—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts characterised by the presence of two or more layers which are next to each other and are fibrous, filamentary, formed of particles or foamed
- B32B5/24—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts characterised by the presence of two or more layers which are next to each other and are fibrous, filamentary, formed of particles or foamed one layer being a fibrous or filamentary layer
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L39/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions of derivatives of such polymers
- C08L39/04—Homopolymers or copolymers of monomers containing heterocyclic rings having nitrogen as ring member
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/04—Polyurethanes
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
- Laminated Bodies (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Synthetic Leather, Interior Materials Or Flexible Sheet Materials (AREA)
Abstract
Description
メチルエチルケトン3,736質量部及びオクチル酸第一錫0.1質量部の存在下、ポリエーテルポリオール(三菱化学株式会社製「PTMG1000」、数平均分子量;1,000)1,000質量部と、2,2−ジメチロールプロピオン酸20質量部と、1,4−ブタンジオール77質量部と、ジフェニルメタンジイソシアネート485質量部とを溶液粘度が20,000mPa・sに達するまで70℃で反応させた後、メタノール3質量部を加えて反応を停止させてアニオン性ウレタン樹脂(A−1−1)のメチルエチルケトン溶液を得た。このウレタン樹脂溶液にポリオキシエチレンジスチレン化フェニルエーテル(Hydrophile−Lipophile Balance(以下、「HLB」と略記する。);13)70質量部と、トリエチルアミン17質量部を混合させた後に、イオン交換水5,408質量部を加えて転相乳化させることで前記アニオン性ウレタン樹脂(A−A−1−1)が水に分散した乳化液を得た。
次いで、前記乳化液からメチルエチルケトンを留去することによって、不揮発分60質量%の樹脂組成物(X−1)を得た。なお、前記アニオン性ウレタン樹脂(A−A−1−1)の流動開始温度は100℃であった。
この樹脂組成物(X−1)100質量部、増粘剤(Borchers社製「Borchi Gel ALA」)2質量部、オキサゾリン架橋剤(日本触媒株式会社製「エポクロスWS−700」(固形分25質量%)、以下「WS−700」と略記する。)5質量部を容器に入れ、メカニカルミキサーにて2,000rpmで2分間撹拌し、次いで、真空脱泡器により脱泡させて水性樹脂組成物(X−1)を得た。
得られた水性樹脂組成物(X−1)を離型紙に塗布し(塗布厚さ150μm)、熱風乾燥機にて70℃、4分間、次いで120℃で2分間乾燥することで乾燥物を得た。この乾燥物を、株式会社島津製作所製フローテスター「CFT−500A」(口径1mm、長さ1mmのダイスを使用、荷重98N、昇温速度3℃/分)を使用して、流動開始温度を測定した。
ポリエーテルポリオールをポリカーボネートポリオール(宇部興産株式会社製「ETERNACOLL UH−100」、数平均分子量;1,000)に変更した以外は、実施例1と同様にして、アニオン性ウレタン樹脂(A−A−1−2)を含む水性樹脂組成物(X−2)を得た。なお、前記アニオン性ウレタン樹脂(A−A−1−2)の流動開始温度は110℃であった。
ポリエーテルポリオールをポリエステルポリオール(株式会社ダイセル製「プラクセ210」、数平均分子量;1,000)に変更した以外は、実施例1と同様にして、アニオン性ウレタン樹脂(A−A−1−3)を含む水性樹脂組成物(X−3)を得た。なお、前記アニオン性ウレタン樹脂(A−A−1−3)の流動開始温度は100℃であった。
実施例1において、オキサゾリン架橋剤(日本触媒株式会社製「エポクロスWS−700」)7質量部を0質量部に変更した以外は、同様にして、水性樹脂組成物(X’−1)を得た。
実施例1において、オキサゾリン架橋剤(日本触媒株式会社製「エポクロスWS−700」)5質量部を、ヘキサメチレンジイソシアネートのイソシアヌレート化合物(以下、「NCO架橋剤」と略記する。)2質量部に変更した以外は、同様にして、水性樹脂組成物(X’−2)を得た。
実施例1において、オキサゾリン架橋剤(日本触媒株式会社製「エポクロスWS−700」)7質量部を、カルボジイミド架橋剤(日清紡ケミカル株式会社製「カルボジライトV−02」(固形分40質量%)、以下「カルボジイミド架橋剤」と略記する。)3質量部に変更した以外は、同様にして、水性樹脂組成物(X’−3)を得た。
メチルエチルケトン3,080質量部及びオクチル酸第一錫0.1質量部の存在下、ポリエーテルポリオール(三菱化学株式会社製「PTMG1000」、数平均分子量;1,000)1,000質量部と、2,2−ジメチロールプロピオン酸20質量部と、ジフェニルメタンジイソシアネート288質量部とを溶液粘度が20,000mPa・sに達するまで70℃で反応させた後、メタノール3質量部を加えて反応を停止させてアニオン性ウレタン樹脂(A’−3)のメチルエチルケトン溶液を得た。このウレタン樹脂溶液にポリオキシエチレンジスチレン化フェニルエーテル(Hydrophile−Lipophile Balance(以下、「HLB」と略記する。);13)66質量部、トリエチルアミン17質量部を混合させた後に、イオン交換水4,474質量部を加えて転相乳化させることで前記アニオン性ウレタン樹脂(A’−1)が水に分散した乳化液を得た。
次いで、前記乳化液からメチルエチルケトンを留去することによって、不揮発分60質量%の樹脂組成物(X’−4)を得た。なお、前記アニオン性ウレタン樹脂(A’−1)の流動開始温度は40℃以下であった。
このアニオン性ウレタン樹脂(A’−1)100質量部、増粘剤(Borchers社製「Borch Gel ALA」)2質量部、オキサゾリン架橋剤(日本触媒株式会社製「エポクロスWS−700」、以下「WS−700」と略記する。)5質量部を容器に入れ、メカニカルミキサーにて2,000rpmで2分間撹拌し、次いで、真空脱泡器により脱泡させて水性樹脂組成物(X−4)を得た。
実施例及び比較例にて用いたポリオール等の数平均分子量は、ゲル・パーミエーション・カラムクロマトグラフィー(GPC)法により、下記の条件で測定し得られた値を示す。
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0.4質量%のテトラヒドロフラン溶液)
標準試料:下記の標準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」
実施例及び比較例において、ウレタン樹脂(A)に架橋剤(B)を配合したときを基点として、3時間経過した後の水性樹脂組成物の粘度(B型粘度計、10Pコーン)を測定し、30,000mPa・s以下であれば「T」、30,000mPa・sを超えた場合は「F」と評価した。
エーテル系ウレタンディスパージョン(DIC株式会社製「ハイドランWLS−120AR」100質量部、増粘剤(Borcher社製「Borch Gel ALA」)2質量部、レべリング剤(Evonik社製「TEGO Flow425」)0.2質量部、消泡剤(Evonik社製「TEGO Twin4000」)0.2質量部、黒色顔料(DIC株式会社製「DILAC HS−9550」)5質量部をメカニカルミキサーにて2,000rpm、2分間撹拌し、次いで真空脱泡機を使用して脱泡させて表皮層用配合液を得た。
離型紙(リンテック株式会社製「EK−100D」)上に、表皮層用配合液をナイフコーターにて塗布した後(塗布厚さ150μm)、熱風乾燥機を使用して70℃で2分間、次いで120℃で2分間乾燥させることにより表皮層を得た。更にこの表皮層上に、実施例及び比較例で得られた水性樹脂組成物を、ナイフコーターを使用して塗布した後(塗布厚さ150μm)、熱風乾燥機を使用して70℃で4分間、次いで120℃で2分間乾燥させた。最後に、不織布基材(目付300g/m2)を前記乾燥物上に重ね、熱ロールプレス(ロール温度130℃、プレス線圧8MPa/m2、送り速度1m/min)にて熱圧着させ、合成皮革を得た。
前記合成皮革から離型紙を剥離し、その上に2.5cm幅のホットメルトテープ(サン化成工業株式会社製「BW−2」)を載置して150℃で30秒間加熱し、接着させた。ホットメルトテープの幅に沿って試料を切断し、この一部を剥離し、基材とホットメルトテープをチャックでつかみ、株式会社島津製作所製オートグラフ試験機「AG−X plus」を使用して、剥離強度を測定した。試験片を20cm剥離して得られたデータの平均値を求め、1cm幅に換算した。なお、表皮層が剥離し、接着強度が測定できなかったものは「−」とした。
前記合成皮革を70℃、湿度95%の環境下で5週間放置した後、同様に剥離強度を測定した。なお、耐湿性試験中に表皮層が脱落したものは「−」とした。
前記合成皮革を120℃の環境下で200時間、及び400時間放置した後、同様に剥離強度を測定した。なお、耐湿性試験中に表皮層が脱落したものは「−」とした。
Claims (4)
- 流動開始温度が50〜155℃の範囲であるウレタン樹脂(A)、水性媒体(B)、及び、オキサゾリン架橋剤(C)を含有することを特徴とする水性樹脂組成物。
- 前記オキサゾリン架橋剤(C)の含有量が、前記ウレタン樹脂(A)100質量部に対して、0.01〜100質量部の範囲である請求項1記載の水性樹脂組成物。
- 請求項1又は2記載の水性樹脂組成物により形成された層(iii)、及び、繊維基材(iv)を有することを特徴とする繊維積層体。
- 前記繊維積層体が、ドライラミネート法により形成されたものである請求項3記載の繊維積層体。
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Application Number | Priority Date | Filing Date | Title |
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JP2016234112 | 2016-12-01 | ||
JP2016234112 | 2016-12-01 | ||
PCT/JP2017/038609 WO2018100930A1 (ja) | 2016-12-01 | 2017-10-26 | 水性樹脂組成物、及び、繊維積層体 |
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JPWO2018100930A1 true JPWO2018100930A1 (ja) | 2018-11-29 |
JP6447783B2 JP6447783B2 (ja) | 2019-01-09 |
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JP2003119677A (ja) * | 2001-10-11 | 2003-04-23 | Dainippon Ink & Chem Inc | 繊維積層体表皮層形成用水性樹脂組成物及びそれを用いた人工皮革 |
JP2003277636A (ja) * | 2002-03-27 | 2003-10-02 | Dainippon Ink & Chem Inc | 水性樹脂組成物 |
JP2008266520A (ja) * | 2007-04-24 | 2008-11-06 | Chuo Rika Kogyo Corp | 接着性樹脂水性エマルジョン |
WO2015093299A1 (ja) * | 2013-12-20 | 2015-06-25 | Dic株式会社 | コーティング剤及び積層体 |
WO2017169244A1 (ja) * | 2016-04-01 | 2017-10-05 | Dic株式会社 | 一液型水性樹脂組成物、及び、繊維積層体 |
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JP2003119677A (ja) * | 2001-10-11 | 2003-04-23 | Dainippon Ink & Chem Inc | 繊維積層体表皮層形成用水性樹脂組成物及びそれを用いた人工皮革 |
JP2003277636A (ja) * | 2002-03-27 | 2003-10-02 | Dainippon Ink & Chem Inc | 水性樹脂組成物 |
JP2008266520A (ja) * | 2007-04-24 | 2008-11-06 | Chuo Rika Kogyo Corp | 接着性樹脂水性エマルジョン |
WO2015093299A1 (ja) * | 2013-12-20 | 2015-06-25 | Dic株式会社 | コーティング剤及び積層体 |
WO2017169244A1 (ja) * | 2016-04-01 | 2017-10-05 | Dic株式会社 | 一液型水性樹脂組成物、及び、繊維積層体 |
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