JP7235178B2 - 水性樹脂組成物、コーティング剤及び接着剤 - Google Patents
水性樹脂組成物、コーティング剤及び接着剤 Download PDFInfo
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- JP7235178B2 JP7235178B2 JP2022546162A JP2022546162A JP7235178B2 JP 7235178 B2 JP7235178 B2 JP 7235178B2 JP 2022546162 A JP2022546162 A JP 2022546162A JP 2022546162 A JP2022546162 A JP 2022546162A JP 7235178 B2 JP7235178 B2 JP 7235178B2
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- JZFHXRUVMKEOFG-UHFFFAOYSA-N tert-butyl dodecaneperoxoate Chemical compound CCCCCCCCCCCC(=O)OOC(C)(C)C JZFHXRUVMKEOFG-UHFFFAOYSA-N 0.000 description 1
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- 238000005292 vacuum distillation Methods 0.000 description 1
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- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
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- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
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- 239000004711 α-olefin Substances 0.000 description 1
Classifications
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- C09D151/00—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers
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Description
シクロペンチル(メタ)アクリレート、シクロヘキシル(メタ)アクリレート、イソボルニル(メタ)アクリレート等の炭素原子数6~20のシクロアルキル(メタ)アクリレート;
フェニル(メタ)アクリレート等のアリル(メタ)アクリレート;
ベンジル(メタ)アクリレート、フェネチル(メタ)アクリレート等の炭素原子数10~20のアラルキル(メタ)アクリレート;
フェノキシエチル(メタ)アクリレート等のアリルオキシアルキル(メタ)アクリレート;
クロトン酸メチル、クロトン酸エチル等のクロトン酸アルキルエステル;
ジメチルマレート、ジブチルマレート、ジメチルフマレート、ジブチルフマレート、ジメチルイタコネート、ジブチルイタコネート等の不飽和ジカルボン酸アルキルエステル;
スチレン、p-tert-ブチルスチレン、α-メチルスチレン、ビニルトルエン、ビニルピリジン、クロロスチレン、クロロメチルスチレン等の芳香族ビニルモノマー;
(メタ)アクリロニトリル、クロトノニトリル、(メタ)アクリルアミド、N-メチル(メタ)アクリルアミド、N-イソプロピル(メタ)アクリルアミド、N-ヒドロキシエチル(メタ)アクリルアミド、N-メチロール(メタ)アクリルアミド、N-メトキシエチル(メタ)アクリルアミド、N,N-ジメチル(メタ)アクリルアミド、N,N-ジエチル(メタ)アクリルアミド、N,N-ジメチルアミノエチル(メタ)アクリレート、N,N-ジメチルアミノプロピル(メタ)アクリルアミド、N,N-ジエチルアミノエチル(メタ)アクリレート、N,N-ジエチルアミノプロピル(メタ)アクリレート、N-(メタ)アクリロイルモルホリン、N-(メタ)アクリロイルピロリジン、N-ビニルホルムアミド、N-ビニルピロリドン、N-ビニルイミダゾール、N-ビニルカルバゾール、N-ビニルキノリン、N-ビニルピペリジン等の窒素原子含有モノマー(好ましくは1置換又は2置換の(メタ)アクリルアミド(置換基が結合して環を形成しているものも含む))及び該窒素原子含有モノマーの塩化メチル塩;
フッ化ビニル、フッ化ビニリデン、テトラフルオロエチレン、クロロトリフルオロエチエレン、ヘキサフルオロプロピレン、塩化ビニル、塩化ビニリデン等のハロゲン化オレフィン;エチレン、プロピレン、イソブチレン、1-ブテン等のα-オレフィン;
酢酸ビニル、プロピオン酸ビニル、ピバリン酸ビニル、バーサティック酸ビニル、安息香酸ビニル、ネオデカン酸ビニル等のカルボン酸ビニルエステル;
メチルビニルエーテル、エチルビニルエーテル、n-ブチルビニルエーテル、イソブチルビニルエーテル等のアルキルビニルエーテル;シクロヘキシルビニルエーテル等のシクロアルキルビニルエーテル;
アクロレイン、メチルビニルケトン等のカルボニル基含有モノマー;
ポリエチレングリコール(メタ)アクリレート、メトキシポリエチレングリコール(メタ)アクリレート、ポリエチレングリコールポリプロピレングリコール共重合(メタ)アクリレート、メトキシポリエチレングリコールポリプロピレングリコール共重合(メタ)アクリレート、ポリエチレングリコールポリテトラメチレングリコール共重合(メタ)アクリレート、メトキシポリエチレングリコールポリテトラメチレングリコール共重合(メタ)アクリレート等のポリオキシエチレン基含有(メタ)アクリルモノマー;
パーフルオロシクロヘキシル(メタ)アクリレート、ジ-パーフルオロシクロヘキシルフマレート、N-イソプロピルフルオロオクタンスルホン酸アミドエチル(メタ)アクリレート等のフルオロアルキル基含有モノマー;
無水マレイン酸、無水シトラコン酸、無水メサコン酸、無水イタコン酸、テトラヒドロ無水フタル酸等の不飽和ジカルボン酸類無水物;
テトラヒドロフルフリル(メタ)アクリレート等の環状エーテル含有モノマー;
ビニリトリクロロシラン、ビニルトリエトキシシラン、ビニルトリス(β-メトキシエトキシ)シラン、γ-(メタ)アクリロキシプロピルトリメトキシシラン等のシリル基含有モノマー;
ビニルスルホン酸、3-アクリロキシプロパン-1-スルホン酸、3-アクリロキシオクチルオキシベンゼンスルホン酸、3-アクリロキシベンゼンジアゾスルホン酸、3-アクリロキシアゾベンゼン-4’-スルホン酸、2-アクリロイルアミノ-2-メチルプロパン-1-スルホン酸、2-アクリロイルアミド-2-メチルプロパンスルホン酸、アクリロニトリル-tert-ブチルスルホン酸等のビニル基含有スルホン酸化合物並びにそれらの塩などが挙げられる。
1/Tga=Σ(Wi/Tgi)・・・
前記ウレタン樹脂(A2)がアニオン性基を有するものである場合、前記水性樹脂組成物は、塩基性化合物を含んでいてもよい。前記基性化合物としては、例えば、アンモニア、トリエチルアミン、モルホリン、モノエタノールアミン、ジエチルエタノールアミン等の有機アミン;水酸化ナトリウム、水酸化カリウム、水酸化リチウム等を含む金属水酸化物などが挙げられる。水性樹脂組成物の水分散安定性を向上させる観点から、前記塩基性化合物とアニオン性基とのモル比(塩基性基/アニオン性基)は、好ましくは0.5以上3.0以下、より好ましくは0.8以上2.0以下である。
本明細書にいう酸価は、原料組成に基づいて前記ウレタン樹脂(A2)に含まれるアニオン性基の量を算出し、これに基づいて前記ウレタン樹脂(A2)1gを中和するのに必要な水酸化カリウムのmg数として算出した理論値である。
本明細書にいうアミン価は、原料組成に基づいて前記ウレタン樹脂(A2)に含まれるカチオン性基の量を算出し、これに基づいてウレタン樹脂(A2)1gを中和するのに必要な塩化水素のモル数(mmol)及び水酸化カリウムの式量(56.1g/mol)の積として算出した理論値である。
ゲル分率(質量%)=(G2/G1)×100
温度計、窒素ガス導入管、攪拌機を備えた反応容器中で窒素ガスを導入しながら、イソフタル酸35.4部、セバシン酸17.8部、アジピン酸7.8部、エチレングリコール6.2部、ネオペンチルグリコール22.9部、1,6-ヘキサンジオール11.7部及びジブチル錫オキサイド0.03部を仕込み180~230℃で酸価が1以下になるまで24時間重縮合反応を行い、ポリエステルポリオール(1)〔酸価0.6mgKOH/g、水酸基価42.5mgKOH/g〕を得た。
温度計、窒素ガス導入管、攪拌機を備えた反応容器中で窒素ガスを導入しながら、イソフタル酸27.6質量部、テレフタル酸27.6質量部、エチレングリコール11.7質量部、ジエチレングリコール19.9質量部及びジブチル錫オキサイド0.03質量部を仕込み180~230℃で酸価が1以下になるまで230℃で24時間重縮合反応を行い、ポリエステルポリオール(2)〔酸価0.6mgKOH/g、水酸基価48.0mgKOH/g〕を得た。
温度計、窒素ガス導入管、攪拌機を備えた反応容器中で窒素ガスを導入しながら、1,6ヘキサンジオール24.8質量部、5-スルホイソフタル酸ジメチルナトリウム20.1質量部、ε―カプロラクトン62.0質量部及びテトライソプロピルチタネート0.02質量部を仕込み、180~230℃で酸価が1以下になるまで12時間重縮合反応を行い、ポリエステルポリオール(3)〔酸価0.3mgKOH/g、水酸基価145.0mgKOH/g〕を得た。
温度計、窒素ガス導入管、攪拌機を備えた反応容器中で窒素ガスを導入しながら、1,4ブタンジオール49.4質量部、アジピン酸71.1部及びテトライソプロピルチタネート0.01質量部を仕込み、180~230℃で酸価が1以下になるまで12時間重縮合反応を行い、ポリエステルポリオール(4)〔酸価0.3mgKOH/g、水酸基価56.0mgKOH/g〕を得た。
反応容器に合成例1のポリエステルポリオール(1)68.0質量部を減圧下100℃で脱水し、その後80℃まで冷却後、メチルエチルケトン98.1質量部を加え、攪拌し均一に混合した。次に、1,4-ブタンジオール4.5質量部、2,2’-ジメチロールプロピオン酸6.1質量部を加え、次いでキシリレンジイソシアネート21.5質量部を加えて、80℃で12時間反応させ、ウレタン化工程を実施した。所定の粘度になったことを確認した後、50℃まで冷却し、不揮発分=51.0%の親水基含有ポリウレタン樹脂(I)を得た。次いで、親水基含有ポリウレタン樹脂(I)に、トリエチルアミン4.8質量部を加え、イオン交換水512質量部をゆっくりと添加し水溶化を実施した。次いで減圧下、30~50℃にてメチルエチルケトンを除去し、不揮発分=23.0%のウレタン樹脂(2)を調製した。
反応容器に合成例2のポリエステルポリオール(2)75.0質量部を減圧下100℃で脱水し、その後80℃まで冷却後、メチルエチルケトン40.0質量部を加え、攪拌し均一に混合した。次に、2,2-ジメチロールプロピオン酸4.5質量部を加え、次いで、イソホロンジイソシアネート13.3質量部を加えて、80℃で12時間反応させ、ウレタン化工程を実施した。所定の粘度になったことを確認し、メタノール0.3質量部を加え、さらに2時間反応させた後、50℃まで冷却し、ウレタンプレポリマーの有機溶剤溶液を得た。
反応容器に合成例3のポリエステルポリオール(3)8.0質量部にメチルエチルケトン10.0質量部を加え、攪拌し均一に混合した後、イソホロンジイソシアネート6.1質量部を投入し、80℃で3時間反応させる。反応後、次に合成例4のポリエステルポリオール(4)8.6質量部及びメチルエチルケトン7.2質量部を加えて、80℃で6時間反応させ、ウレタン化工程を実施した。イソシアネート値が0.1%以下になったのを確認し、n-ブタノール0.1質量部を加え、さらに2時間反応させた後、50℃まで冷却し、ウレタンプレポリマーの有機溶剤溶液を得た。
エポキシ当量132のエチレングリコールジグリシジルエーテル100質量部とヨウ化ナトリウム10質量部、1,8-ジアザビシクロ[5.4.0]-7-ウンデセン10質量部、N,N-ジメチルホルムアミド100質量部とを反応容器内に仕込んだ。次いで、撹拌しながら二酸化炭素を連続して吹き込み、100℃にて20時間反応を行った。得られたカーボナート化合物100質量部、ヘキサメチレンジアミン31.0質量部、リシン18.1質量部、N,N-ジメチルホルムアミド70部を加え、70℃の温度で撹拌しながら24時間の反応を行った。反応後冷却し、水330質量部を加え、十分に攪拌することにより、ウレタン樹脂の水分散体を得、次いでエージング・脱溶剤することによって、不揮発分25質量%のウレタン樹脂(4)を得た。
反応容器に合成例1のポリエステルポリオール(1)67.0質量部を減圧下100℃で脱水し、その後80℃まで冷却後、メチルエチルケトン98.0質量部を加え、攪拌し均一に混合した。次に、2,3-ビス(2-メルカプトエチルチオ)プロパン-1-チオール7.1質量部、2,2’-ジメチロールプロピオン酸6.0質量部を加え、次いでトリレンジイソシアネート18.0質量部を加えて、80℃で12時間反応させ、ウレタン化工程を実施した。所定の粘度になったことを確認した後、50℃まで冷却し、不揮発分=51.0%の親水基含有ポリウレタン樹脂(II)を得た。次いで、親水基含有ポリウレタン樹脂(II)に、トリエチルアミン4.8質量部を加え、イオン交換水512質量部をゆっくりと添加し水溶化を実施した。次いで減圧下、30~50℃にてメチルエチルケトンを除去し、不揮発分=23.0%のウレタン樹脂(5)を調製した。
反応容器に合成例1のポリエステルポリオール(1)69.0質量部を減圧下100℃で脱水し、その後80℃まで冷却後、メチルエチルケトン93.30質量部を加え、攪拌し均一に混合した。次に、1,4-ブタンジオール3.0質量部2,2’-ジメチロールプロピオン酸6.1質量部を加え、次いでトリレンジイソシアネート22.9質量部を加えて、80℃で12時間反応させ、ウレタン化工程を実施した。イソシアネート値が0.1%以下になったのを確認した後、50℃まで冷却し、不揮発分=51.0%の親水基含有ポリウレタン樹脂(II)を得た。次いで、親水基含有ポリウレタン樹脂(II)に、トリエチルアミン4.6質量部を加え、イオン交換水548質量部をゆっくりと添加し水溶化を実施した。次いで減圧下、30~50℃にてメチルエチルケトンを除去し、不揮発分=23.0%のウレタン樹脂(6)を調製した。
製造例1で得られたウレタン樹脂(1)321質量部にイオン交換水126質量部を加え、イソプレン25.3質量部、スチレン6.3質量部を過硫酸アンモニア(APS)0.3質量部でモノマー一括乳化重合(反応温度70℃)の条件下反応させて、次に未反応モノマー除去の濃縮を行い、水分量を調整後、固形分25%のラテックス複合ウレタン樹脂(1)を得た。
製造例2で得られたウレタン樹脂(2)305質量部にイオン交換水145質量部を加え、イソプレン23.0質量部、スチレン5.8質量部を過硫酸アンモニア(APS)0.3質量部でモノマー一括乳化重合(反応温度70℃)の条件下反応させて、次に未反応モノマー除去の濃縮を行い、水分量を調整後、固形分25%のラテックス複合ウレタン樹脂(2)を得た。
製造例1で得られたウレタン樹脂(1)378質量部にイオン交換水63.5質量部を加え、イソプレン18.6質量部、アクリル酸4-ヒドロキシブチル18.6質量部を過硫酸アンモニア(APS)0.3質量部でモノマー一括乳化重合(反応温度70℃)の条件下反応させて、次に未反応モノマー除去の濃縮を行い、水分量を調整後、固形分25%のラテックス複合ウレタン樹脂(3)を得た。
製造例3で得られたウレタン樹脂(3)269質量部にイオン交換水152質量部を加え、イソプレン28.8質量部、メタクリル酸グリシジル28.8質量部を過硫酸アンモニア(APS)0.3質量部でモノマー一括乳化重合(反応温度70℃)の条件下反応させて、50℃まで冷却後に2,3-ビス(2-メルカプトエチルチオ)プロパン-1-チオール17.6質量部を添加し、グリシジルを開環させる。次に未反応モノマー除去の濃縮を行い、水分量を調整後、固形分48%のラテックス複合ウレタン樹脂(4)を得た。
製造例4で得られたウレタン樹脂(4)296質量部にイオン交換水152質量部を加え、イソプレン25.3質量部、スチレン6.3質量部を過硫酸アンモニア(APS)0.3質量部でモノマー一括乳化重合(反応温度70℃)の条件下反応させて、次に未反応モノマー除去の濃縮を行い、水分量を調整後、固形分30%のラテックス複合ウレタン樹脂(5)を得た。
製造例5で得られたウレタン樹脂(5)321質量部にイオン交換水126質量部を加え、イソプレン25.3部、スチレン6.3質量部を過硫酸アンモニア(APS)0.3質量部でモノマー一括乳化重合(反応温度70℃)の条件下反応させて、次に未反応モノマー除去の濃縮を行い、水分量を調整後、固形分25%のラテックス複合ウレタン樹脂(6)を得た。
製造例6で得られたウレタン樹脂(6)を使用した。
製造例6で得られたウレタン樹脂(6)321質量部にイオン交換水126質量部を加え、イソプレン25.3質量部、スチレン6.3質量部及びアクリル酸ブチル42.2質量部を過硫酸アンモニア(APS)0.3部でモノマー一括乳化重合(反応温度70℃)の条件下反応させて、次に未反応モノマー除去の濃縮を行い、水分量を調整後、固形分25%のラテックス複合ウレタン樹脂(8)を得た。
製造例4で得られたウレタン樹脂(4)を使用した。
PETへ塗工し140℃20秒で乾燥させた面に、SBR、NBR基材を貼り付け、約100℃で圧着し、約2日間エージングさせる。エージング後のPETとSBR, NBR基材を剥がし、剥がれた基材の状態を観察した。
〇:PET、もしくはSBR, NBR基材が材料破壊した。もしくは、剥がれなかった。
△:PETとSBR, NBR間で接着性を確認できたが、PETもしくはSBR, NBRのどちらかの基材のみに接着層が残った。
×:PETとSBR, NBR間でほとんど接着性を確認できず、PETもしくはSBR, NBRのどちらかの基材のみに接着層が残った。
酸素透過率の測定は、JIS-K7126(等圧法)に準じ、モコン社製酸素透過率測
定装置OX-TRAN1/50を用いて、温度23℃、湿度0%RHの雰囲気下、及び、
温度23℃、湿度90%RHの雰囲気下で実施した。なお、RHとは相対湿度を表す。
水蒸気透過率の測定は、JIS-K7129に準じ、イリノイ社製水蒸気透過率測定装
置7001を用いて、温度40℃、湿度90%RHの雰囲気下で測定した。
Claims (7)
- 複合樹脂(A)及び水性媒体(B)を含む水性樹脂組成物の製造方法であって、
前記複合樹脂(A)が、ビニル重合体(A1)と、ウレタン樹脂(A2)とを含むものであり、
前記ビニル重合体(A1)が、共役ジエン化合物(a1)を含むビニル単量体(a)に由来する単位を有するものであり、
前記ウレタン樹脂(A2)が、ヒドロキシ基及び/又はチオール基を有するものであり、
前記複合樹脂(A)が、ヒドロキシ基及び/又はチオール基を有するものであり、
前記複合樹脂(A)が、前記ウレタン樹脂(A2)の存在下、前記水性媒体(B)中で前記ビニル単量体(a)を一括乳化重合したものである水性樹脂組成物の製造方法。 - 前記ウレタン樹脂(A2)の含有量が、前記ビニル重合体(A1)1質量部に対して、0.1質量部以上、100質量部以下である請求項1記載の水性樹脂組成物の製造方法。
- 前記ウレタン樹脂(A2)の重量平均分子量が、5,000以上500,000以下である請求項1又は2記載の水性樹脂組成物の製造方法。
- 請求項1~3のいずれか1項記載の水性樹脂組成物の製造方法にて得た水性樹脂組成物を含む接着剤の製造方法。
- ゴム用接着剤である請求項4記載の接着剤の製造方法。
- 請求項1~3のいずれか1項記載の水性樹脂組成物の製造方法にて得た水性樹脂組成物を含むコーティング剤の製造方法。
- 紙基材用である請求項6記載のコーティング剤の製造方法。
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