JPWO2017010211A1 - 凝固物の製造方法 - Google Patents
凝固物の製造方法 Download PDFInfo
- Publication number
- JPWO2017010211A1 JPWO2017010211A1 JP2016569463A JP2016569463A JPWO2017010211A1 JP WO2017010211 A1 JPWO2017010211 A1 JP WO2017010211A1 JP 2016569463 A JP2016569463 A JP 2016569463A JP 2016569463 A JP2016569463 A JP 2016569463A JP WO2017010211 A1 JPWO2017010211 A1 JP WO2017010211A1
- Authority
- JP
- Japan
- Prior art keywords
- urethane resin
- mass
- parts
- resin composition
- aqueous 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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- 238000005345 coagulation Methods 0.000 claims abstract description 24
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- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Natural products C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 6
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- 239000004721 Polyphenylene oxide Substances 0.000 description 4
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- KXBFLNPZHXDQLV-UHFFFAOYSA-N [cyclohexyl(diisocyanato)methyl]cyclohexane Chemical compound C1CCCCC1C(N=C=O)(N=C=O)C1CCCCC1 KXBFLNPZHXDQLV-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
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- 125000002091 cationic group Chemical group 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
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- 229920001778 nylon Polymers 0.000 description 3
- 125000006353 oxyethylene group Chemical group 0.000 description 3
- 229920005906 polyester polyol Polymers 0.000 description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- BJZYYSAMLOBSDY-QMMMGPOBSA-N (2s)-2-butoxybutan-1-ol Chemical compound CCCCO[C@@H](CC)CO BJZYYSAMLOBSDY-QMMMGPOBSA-N 0.000 description 2
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 2
- WFRBDWRZVBPBDO-UHFFFAOYSA-N 2-methyl-2-pentanol Chemical compound CCCC(C)(C)O WFRBDWRZVBPBDO-UHFFFAOYSA-N 0.000 description 2
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Abstract
Description
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」
メチルエチルケトン3,281質量部及びオクチル酸第一錫0.1質量部の存在下、ポリカーボネートポリオール(日本ポリウレタン株式会社製「ニッポラン980R」、数平均分子量;2,000)1,000質量部と、2,2’−ジメチロールプロピオン酸17質量部と、エチレングリコール47質量部と、ジフェニルメタンジイソシアネート344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水性ウレタン樹脂(A−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);14)70質量部と、トリエチルアミン13質量部を混合させた後に、イオン交換水800質量部を加えて転相乳化させることで前記水性ウレタン樹脂(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40質量%の水性ウレタン樹脂組成物(X−1)を得た。なお、前記水性ウレタン樹脂(A−1)中の芳香環の含有量は、1.93mol/kgであった。
メチルエチルケトン3,281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(三菱化型株式会社製「PTMG2000」、数平均分子量;2,000)1,000質量部と、2,2’−ジメチロールプロピオン酸17質量部と、エチレングリコール47質量部と、ジフェニルメタンジイソシアネート344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水性ウレタン樹脂(A−2)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(HLB;14)70質量部と、トリエチルアミン13質量部を混合させた後に、イオン交換水800質量部を加えて転相乳化させることで前記水性ウレタン樹脂(A−2)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40質量%の水性ウレタン樹脂組成物(X−2)を得た。なお、前記水性ウレタン樹脂(A−2)中の芳香環の含有量は、1.93mol/kgであった。
メチルエチルケトン3,281質量部及びオクチル酸第一錫0.1質量部の存在下、ポリエステルポリオール(株式会社ダイセル製「プラクセル220」、数平均分子量;2,000)1,000質量部と、2,2’−ジメチロールプロピオン酸17質量部と、エチレングリコール47質量部と、ジフェニルメタンジイソシアネート344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水性ウレタン樹脂(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(HLB;14)70質量部と、トリエチルアミン13質量部を混合させた後に、イオン交換水800質量部を加えて転相乳化させることで前記水性ウレタン樹脂(A−3)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40質量%の水性ウレタン樹脂組成物(X−3)を得た。なお、前記水性ウレタン樹脂(A−3)中の芳香環の含有量は、1.93mol/kgであった。
メチルエチルケトン1,279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(三菱化型株式会社製「PTMG2000」、数平均分子量;2,000)1,000質量部と、2,2’−ジメチロールプロピオン酸17質量部と、ジシクロヘキシルメタンジイソシアネート262質量部とをイソシアネート含有率が1.23質量%に達するまで70℃で反応させ、水性ウレタン樹脂(A−4)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(HLB;14)64質量部と、トリエチルアミン13質量部を混合させた後に、イオン交換水2,558質量部を加えて転相乳化させ、更にイソホロンジアミンの10質量%溶液607質量部を混合させることで前記水性ウレタン樹脂(A−4)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及び水を留去することによって、不揮発分40質量%の水性ウレタン樹脂組成物(X−4)を得た。
メチルエチルケトン1,279質量部及びオクチル酸第一錫0.1質量部の存在下、ポリエステルポリオール(株式会社ダイセル製「プラクセル220」、数平均分子量;2,000)1,000質量部と、2,2’−ジメチロールプロピオン酸17質量部と、ジシクロヘキシルメタンジイソシアネート262質量部とをイソシアネート含有率が1.23質量%に達するまで70℃で反応させ、水性ウレタン樹脂(A−5)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(HLB;14)64質量部と、トリエチルアミン13質量部を混合させた後に、イオン交換水2,558質量部を加えて転相乳化させ、更にイソホロンジアミンの10質量%溶液607質量部を混合させることで前記水性ウレタン樹脂(A−5)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及び水を留去することによって、不揮発分40質量%の水性ウレタン樹脂組成物(X−5)を得た。
合成例1で得られた水性ウレタン樹脂組成物(X−1)100質量部、増粘剤(Borcher社製「Borch Gel L75N」)5質量部、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SV−02」)4質量部、イオン交換水200質量部をメカニカルミキサーにて2,000rpmで2分間撹拌し、次いで真空脱泡機で脱泡させることで、配合液を調製した。
次いで、不織布(目付250g/m2)に前記配合液を含浸させた後、ゴムローラーマングルを用いて含浸量が200%となるように不要な配合液を絞り取った。次いで、配合液を含ませた不織布を2−プロパノールの凝固浴に3分間浸漬させて配合液を凝固させた。最後に、100℃の熱風乾燥機にて30分乾燥させて凝固物を有する繊維基材を得た。
用いる水性ウレタン樹脂組成物の種類を表1に示す通り変更した以外は、実施例1と同様にして凝固物を有する繊維基材を得た。
合成例1で得られた水性ウレタン樹脂組成物(X−1)100質量部、塩化ナトリウム2質量%水溶液100質量部とをメカニカルミキサーを用い2,000rpmの条件で2分間撹拌することによって、それぞれ、含浸用の水性ウレタン樹脂組成物を調製した。
次いで、不織布(目付250g/m2)を、前記で得た含浸用の水性ウレタン樹脂組成物が入った槽に浸漬し、次いで、ゴムローラーのマングルを用いてそれを絞ることによって、前記不織布の質量と同質量のウレタン樹脂組成物が浸漬した浸漬物を得た。次いで、それを前記ギアー式熱風乾燥機を用い100℃で10分乾燥することによって、感熱凝固による凝固物を有する繊維基材を得た。
実施例1において、2−プロパノールの凝固浴に代えて、メタノールの凝固浴を使用した以外は実施例1と同様にして繊維基材の含浸工程を行ったが、水性ウレタン樹脂組成物(X−1)は凝固しなかった。
実施例1において、2−プロパノールの凝固浴に代えて、ヘキサノールの凝固浴を使用した以外は実施例1と同様にして繊維基材の含浸工程を行ったが、水性ウレタン樹脂組成物(X−1)は凝固しなかった。
実施例1〜5及び比較例1〜3で得られた凝固物を有する繊維基材を、5cm四方に裁断し、精密天秤にて質量を測定した。皮革用に含浸工程前の繊維基材を5cm四方に裁断し精密天秤にて質量を測定した。両者の質量の差を測定し、水性ウレタン樹脂の付着量(g/m2)を算出した。
実施例1〜5及び比較例1〜3で得られた凝固物を有する繊維基材を、日立ハイテクテクノロジー株式会社製走査型電子顕微鏡「SU3500」(倍率200倍)を使用して観察し、以下のように評価した。
「T」;水性ウレタン樹脂が繊維基材内部で繊維と絡み付いた状態が確認される。
「F」;水性ウレタン樹脂が繊維基材内部で繊維と絡み付いた状態が確認されない。
実施例1〜5及び比較例1〜3で得られた凝固物を有する繊維基材を、手で触った際の触感により以下のように評価した。
「A」;張り腰感、充実感共に優れている。
「B」;張り腰感、充実感が感じられる。
「C」;張り腰感、充実感がやや劣る。
「D」;張り腰感、充実感が全く感じられない。
合成例1で得られた水性ウレタン樹脂組成物(X−1)100質量部と水で5質量%に希釈したカルボキシメチルセルロース5質量部とをメカニカルミキサーを使用して2,000rpmで2分間撹拌し、次いで真空脱泡機を使用して脱泡させ、配合液を得た。
次いで、手型にナイロン繊維による編み手袋を装着させ、2−プロパノールに15秒浸漬させた後、更に前記配合液にこの手型を10秒間浸漬させ、引き上げた。その後、手型を熱風乾燥機を使用して、70℃で20分間、120℃で20分間乾燥して手型から編み手袋を取出し、凝固皮膜を有する手袋を得た。
用いる水性ウレタン樹脂組成物の種類を表2に示す通り変更した以外は、実施例1と同様にして凝固皮膜を有する手袋を得た。
合成例1で得られた水性ウレタン樹脂組成物(X−1)100質量部、塩化ナトリウム
1質量部、水で5質量%に希釈したカルボキシメチルセルロース5質量部をメカニカルミキサーにて2,000rpmで2分間撹拌し、次いで遠心脱泡機を使用して脱泡させ配合液を得た。
次いで、手型にナイロン繊維による編み手袋を装着させ、前記配合液にこの手型を10秒間浸漬させ、引き上げた。その後、手型を熱風乾燥機を使用して、70℃で20分間、120℃で20分間乾燥して手型から編み手袋を取出し、凝固皮膜を有する手袋を得た。
実施例6において、2−プロパノールの凝固浴に代えて、メタノールの凝固浴を使用した以外は実施例1と同様にして繊維基材の浸漬工程を行ったが、水性ウレタン樹脂組成物(X−1)は凝固しなかった。
実施例6において、2−プロパノールの凝固浴に代えて、ヘキサノールの凝固浴を使用した以外は実施例1と同様にして繊維基材の浸漬工程を行ったが、水性ウレタン樹脂組成物(X−1)は凝固しなかった。
実施例6〜10及び比較例4〜6で得られた手袋を目視観察することにより、以下のように評価した。
「T」;凝固皮膜が形成されている。
「F」;凝固皮膜が形成されていない。
実施例6〜10及び比較例4〜6で得られた凝手袋を、手で触った際の触感により以下のように評価した。
「A」;柔軟性に優れる。
「B」;柔軟性にやや優れる。
「C」;柔軟ではない。
「IPA」;2−プロパノール
Claims (4)
- 水性ウレタン樹脂組成物を炭素原子数2〜6のアルコール溶媒で凝固させることにより得られたことを特徴とする凝固物の製造方法。
- 繊維基材に、水性ウレタン樹脂組成物を含浸し、次いで、炭素原子数2〜6のアルコール溶媒の凝固浴に浸漬させる工程を有する請求項1記載の凝固物の製造方法。
- 繊維基材を、炭素原子数2〜6のアルコール溶媒の凝固浴に浸漬し、次いで、水性ウレタン樹脂組成物中に浸漬させる工程を有する請求項1記載の凝固物の製造方法。
- 前記アルコール溶媒が、2−プロパノールである請求項1〜3のいずれか1項記載の凝固物の製造方法。
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PCT/JP2016/067644 WO2017010211A1 (ja) | 2015-07-14 | 2016-06-14 | 凝固物の製造方法 |
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JPS5848579B2 (ja) * | 1974-10-03 | 1983-10-29 | テイジンコ−ドレ カブシキガイシヤ | ビタコウセイシ−トザイリヨウノ セイゾウホウ |
US4102959A (en) * | 1975-07-31 | 1978-07-25 | Idemitsu Kosan Company, Ltd. | Process for preparing film by wet method |
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JP6146546B1 (ja) | 2017-06-14 |
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