JPWO2019181476A1 - 接着剤、及び、合成皮革 - Google Patents
接着剤、及び、合成皮革 Download PDFInfo
- Publication number
- JPWO2019181476A1 JPWO2019181476A1 JP2019545828A JP2019545828A JPWO2019181476A1 JP WO2019181476 A1 JPWO2019181476 A1 JP WO2019181476A1 JP 2019545828 A JP2019545828 A JP 2019545828A JP 2019545828 A JP2019545828 A JP 2019545828A JP WO2019181476 A1 JPWO2019181476 A1 JP WO2019181476A1
- Authority
- JP
- Japan
- Prior art keywords
- mass
- urethane resin
- parts
- adhesive
- anionic urethane
- Prior art date
- Legal status (The legal status 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 status listed.)
- Granted
Links
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- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Dispersion Chemistry (AREA)
- Textile Engineering (AREA)
- Manufacturing & Machinery (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Polyurethanes Or Polyureas (AREA)
- Synthetic Leather, Interior Materials Or Flexible Sheet Materials (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Description
メチルエチルケトン1,374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57質量部と、イソホロンジイソシアネート317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)69質量部と、トリエチルアミン(中和剤;沸点89.5℃)38質量部を混合させた後に、イオン交換水2,748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35質量%のウレタン樹脂組成物を得た。なお、前記アニオン性ウレタン樹脂の流動開始温度は40℃以下、酸価は17.4mgKOH/gであった。
架橋剤を配合する前のウレタン樹脂組成物を離型紙に塗布し(塗布厚さ150μm)、熱風乾燥機にて70℃、2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。
架橋剤を配合する前のウレタン樹脂組成物を乾燥し、乾燥固化した樹脂粒子の0.05g〜0.5gを、300mL三角フラスコに秤量し、次いで、テトラヒドロフランとイオン交換水との質量割合[テトラヒドロフラン/イオン交換水]が80/20の混合溶媒約80mLを加えそれらの混合液を得た。
次いで、前記混合液にフェノールフタレイン指示薬を混合した後、あらかじめ標定された0.1mol/Lの水酸化カリウム水溶液で滴定し、滴定に用いた水酸化カリウム水溶液の量から下記計算式(1)に従い、水性ウレタン樹脂(A)の酸価(mgKOH/g)を求めた。
計算式 A=(B×f×5.611)/S (1)
式中、Aは樹脂の固形分酸価(mgKOH/g)、Bは滴定に用いた0.1mol/L水酸化カリウム水溶液の量(mL)、fは0.1mol/L水酸化カリウム水溶液のファクター、Sは樹脂粒子の質量(g)、5.611は水酸化カリウムの式量(56.11/10)である。
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、接着剤を得た。なお、前記アニオン性ウレタン樹脂の流動開始温度は40℃以下、酸価は17.2mgKOH/g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「プラクセル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、接着剤を得た。なお、前記アニオン性ウレタン樹脂の流動開始温度は40℃以下、酸価は17.2mgKOH/gであった。
メチルエチルケトン1,374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57質量部と、イソホロンジイソシアネート317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)69質量部と、トリプロピルアミン(中和剤;沸点156℃)61質量部を混合させた後に、イオン交換水2,748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35質量%のウレタン樹脂組成物を得た。なお、前記アニオン性ウレタン樹脂の流動開始温度は40℃以下、酸価は17.4mgKOH/gであった。
メチルエチルケトン1,374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57質量部と、イソホロンジイソシアネート317質量部とを溶液粘度が40,000mPa・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)69質量部と、トリエチルアミン(中和剤;沸点89.5℃)38質量部を混合させた後に、イオン交換水2,748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35質量%のウレタン樹脂組成物を得た。なお、前記アニオン性ウレタン樹脂の流動開始温度は52℃、酸価は17.4mgKOH/gであった。
メチルエチルケトン1,418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74質量部と、イソホロンジイソシアネート345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)69質量部と、トリエチルアミン(中和剤;沸点89.5℃)38質量部を混合させた後に、イオン交換水2,836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35質量%のウレタン樹脂組成物を得た。なお、前記アニオン性ウレタン樹脂の流動開始温度は40℃以下、酸価は21.8mgKOH/gであった。
実施例1において、カルボジイミド架橋剤を用いなかった以外は実施例1と同様にして接着剤を得た。
実施例1において、カルボジイミド架橋剤に代えて、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」、固形分25質量%)を用いた以外は実施例1と同様にして接着剤を得た。
メチルエチルケトン4,121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57質量部と、イソホロンジイソシアネート317質量部とを溶液粘度が100,000mPa・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)69質量部と、トリエチルアミン(中和剤;沸点89.5℃)38質量部を混合させた後に、イオン交換水5,495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35質量%のウレタン樹脂組成物を得た。なお、前記アニオン性ウレタン樹脂の流動開始温度は110℃、酸価は17.4mgKOH/gであった。
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および比較例で得た接着剤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6分間乾燥させた。最後に、不織布基材を前記乾燥物上に重ね、熱ロールプレス(ロール温度100℃、プレス線圧3MPa/m2、送り速度1m/min)にて熱圧着させ、さらに熱風乾燥機にて70℃で2日間エージングさせることで合成皮革を得た。
実施例および比較例で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」
実施例および比較例において、架橋剤を配合してから10分経過後、および3日経過後の接着剤の粘度を測定し(B型粘度計、10Pコーン、ローター回転数;50rpm)、10分経過後に対する3日経過後粘度上昇率が架橋剤配合前から0.5〜2倍以内であるものは「○」と評価し、0.5倍より小さい、または2倍を超えているものは「×」と評価した。
2.5cm幅のホットメルトテープ(サン化成株式会社製「BW−2」)を合成皮革表面に載置し150℃で30秒加熱し、ホットメルトテープを接着した。その後、ホットメルトテープの幅に沿って試料を裁断した。この資料の一部を剥離し、基材とホットメルトテープとをチャックで挟み、張試験機「オートグラフAG−I」(株式会社島津製作所製)を使用して剥離強度を測定した(以下「初期剥離強度」と略記する。)。得られたデータ(n=3)の平均値を求め、1cm幅に換算した(単位;kgf/cm)。
また、実施例および比較例において、架橋剤を配合してから6時間経過してから、合成皮革を作製したものを同様に評価したものを「配合6時間経過後の剥離強度」とした。
Claims (6)
- 流動開始温度が100℃以下であるアニオン性ウレタン樹脂(A)、中和剤(B)、カルボジイミド架橋剤(C)、及び、水性媒体(D)を含有することを特徴とする接着剤。
- 前記アニオン性ウレタン樹脂(A)の酸価が、1〜35mgKOH/gの範囲である請求項1記載の接着剤。
- 前記中和剤(B)の沸点が、200℃以下である請求項1又は2記載の接着剤。
- 前記カルボジイミド架橋剤(C)が、1,3−ビス(1−メチル−1−イソシアナトエチル)ベンゼン、1,4−ビス(1−メチル−1−イソシアナトエチル)ベンゼン、及び、ジシクロヘキシルメタンジイソシアネートからなる群より選ばれる1種以上のポリイソシアネートを原料とするものである請求項1〜3のいずれか1項記載の接着剤。
- 前記カルボジイミド架橋剤(C)の含有量が、前記アニオン性ウレタン樹脂(A)100質量部に対して、0.5〜25質量部の範囲である請求項1〜4のいずれか1項記載の接着剤。
- 少なくとも、基材(i)、請求項1〜5のいずれか1項記載の接着剤により形成された接着層(ii)、及び、表皮層(iii)を有することを特徴とする合成皮革。
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2019
- 2019-03-05 KR KR1020207025918A patent/KR102356293B1/ko active IP Right Grant
- 2019-03-05 US US16/982,111 patent/US20210009875A1/en not_active Abandoned
- 2019-03-05 WO PCT/JP2019/008552 patent/WO2019181476A1/ja unknown
- 2019-03-05 EP EP19770982.7A patent/EP3770229A4/en active Pending
- 2019-03-05 CN CN201980019687.4A patent/CN111868195B/zh active Active
- 2019-03-05 JP JP2019545828A patent/JP6620965B1/ja active Active
- 2019-03-07 TW TW108107560A patent/TWI798376B/zh active
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TWI798376B (zh) | 2023-04-11 |
KR20200118182A (ko) | 2020-10-14 |
CN111868195A (zh) | 2020-10-30 |
EP3770229A4 (en) | 2021-11-24 |
KR102356293B1 (ko) | 2022-02-08 |
TW201940637A (zh) | 2019-10-16 |
CN111868195B (zh) | 2022-05-06 |
EP3770229A1 (en) | 2021-01-27 |
WO2019181476A1 (ja) | 2019-09-26 |
US20210009875A1 (en) | 2021-01-14 |
JP6620965B1 (ja) | 2019-12-18 |
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