JP7124316B2 - 水性樹脂分散体の製造方法 - Google Patents
水性樹脂分散体の製造方法 Download PDFInfo
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- JP7124316B2 JP7124316B2 JP2017533644A JP2017533644A JP7124316B2 JP 7124316 B2 JP7124316 B2 JP 7124316B2 JP 2017533644 A JP2017533644 A JP 2017533644A JP 2017533644 A JP2017533644 A JP 2017533644A JP 7124316 B2 JP7124316 B2 JP 7124316B2
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- polymerization
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Classifications
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- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
- C09D4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09D159/00 - C09D187/00
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- C08F2/16—Aqueous medium
- C08F2/22—Emulsion polymerisation
- C08F2/24—Emulsion polymerisation with the aid of emulsifying agents
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- C08F255/00—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00
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- C08F255/00—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00
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- C08F255/00—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00
- C08F255/08—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00 on to polymers of olefins having four or more carbon atoms
- C08F255/10—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00 on to polymers of olefins having four or more carbon atoms on to butene polymers
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- C08F285/00—Macromolecular compounds obtained by polymerising monomers on to preformed graft polymers
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- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
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- C09D123/00—Coating compositions based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Coating compositions based on derivatives of such polymers
- C09D123/26—Coating compositions based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Coating compositions based on derivatives of such polymers modified by chemical after-treatment
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- C09D123/00—Coating compositions based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Coating compositions based on derivatives of such polymers
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- C09D133/00—Coating compositions based on 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 only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
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- C09D133/00—Coating compositions based on 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 only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
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Description
〔1〕ポリオレフィン分散体(A)、ラジカル重合性単量体(B)及び乳化重合用界面活性剤(C)を混合して重合する重合工程を含む水性樹脂分散体の製造方法であって、前記重合工程において、重合開始剤添加時に前記ラジカル重合性単量体(B)の混合量が、前記ポリオレフィン分散体(A)の固形分質量部の0.5~2倍であり、前記乳化重合用界面活性剤(C)の固形分の混合量が、前記ラジカル重合性単量体(B)の全量100質量部に対して0~3質量部である水性樹脂分散体の製造方法。
〔2〕 前記重合工程において、前記水性樹脂分散体の製造に用いる全てのラジカル重合性単量体(B)の50~100質量%を重合開始剤により一括重合する操作を含む〔1〕に記載の水性樹脂分散体の製造方法。
〔3〕 ポリオレフィン分散体(A)及び乳化重合用界面活性剤(C)の存在下でラジカル重合性単量体(B)を重合する重合工程を含む水性樹脂分散体の製造方法であって、前記重合工程において、前記水性樹脂分散体の製造に用いるラジカル重合性単量体(B)の全量に対して50~100質量%のラジカル重合性単量体(B)を重合開始剤により一括重合する操作を含み、前記乳化重合用界面活性剤(C)の使用量が、前記水性樹脂分散体の製造に用いるラジカル重合性単量体(B)の全量100質量部に対して0~3質量部である水性樹脂分散体の製造方法。
〔4〕 前記ポリオレフィン分散体(A)がハロゲン原子を含有しない〔1〕~〔3〕に記載の水性樹脂分散体の製造方法。
〔5〕 前記ポリオレフィン分散体(A)が、ポリオレフィンと、グリフィン法で計算されるHLBが1~8のポリエーテル樹脂(D)とを分散媒に分散させて製造したものである〔1〕~〔4〕のいずれかに記載の水性樹脂分散体の製造方法。
〔6〕 前記水性樹脂分散体がプライマー用である〔1〕~〔5〕のいずれかに記載の水性樹脂分散体の製造方法。
本発明の一つの態様は、ポリオレフィン分散体(A)、ラジカル重合性単量体(B)及び乳化重合用界面活性剤(C)を混合して重合する工程を含む水性樹脂分散体の製造方法であって、前記ラジカル重合性単量体(B)の混合量が、前記ポリオレフィン分散体(A)の固形分質量部の0.5~2倍であり、前記乳化重合用界面活性剤(C)の固形分の混合量が、前記ラジカル重合性単量体(B)100質量部に対して0~3質量部であることを特徴とする水性樹脂分散体の製造方法である。
また本発明の別の態様は、ポリオレフィン分散体(A)及び乳化重合用界面活性剤(C)の存在下でラジカル重合性単量体(B)を重合する重合工程を含む水性樹脂分散体の製造方法であって、前記重合工程において、前記水性樹脂分散体の製造に用いる全てのラジカル重合性単量体(B)の50~100質量%を重合開始剤により一括重合する操作を含み、前記乳化重合用界面活性剤(C)の使用量が、前記水性樹脂分散体の製造に用いるラジカル重合性単量体(B)の全量100質量部に対して0~3質量部であることを特徴とする水性樹脂分散体の製造方法である。
本発明において、ポリオレフィン分散体(A)は、オレフィン重合体(以下、「ポリオレフィン」とも称する。)を水、及び/又は水以外の溶媒に分散させたオレフィン重合体の分散体をいう。また、オレフィン重合体とは、主な構成単位としてオレフィンを含む重合体をいい、オレフィンの単独重合体や共重合体等のオレフィン系重合体(A1)(以下、「重合体(A1)」とも称する。)等を示す。
前記オレフィン系重合体(A1)(重合体(A1))としては、反応性基を有さないオレフィン系重合体(A11)(以下、「重合体(A11)」とも称する。)や、反応性基を有する変性オレフィン系重合体(A12)(以下、「重合体(A12)」とも称する。)等が挙げられる。
(1)プロピレン含有率が50モル%以上である。なお、プロピレン含有率は、より好ましくは60モル%以上であり、さらに好ましくは70モル%以上である。
(2)融点(Tm)が125℃以下である。なお、Tmは、より好ましくは100℃以下、さらに好ましくは90℃以下である。さらに、Tmは、好ましくは60℃以上である。
前記反応性基を有さないオレフィン系重合体(A11)(重合体(A11))としては、公知の各種オレフィン系重合体及びオレフィン系共重合体を用いることができる。具体的には、特に限定されないが、以下のポリオレフィンを挙げることができる。エチレン又はプロピレンの単独重合体;エチレン及びプロピレンの共重合体;エチレン及び/又はプロピレンと、その他のコモノマー(例えば、ブテン-1、ペンテン-1、ヘキセン-1、ヘプテン-1、オクテン-1、シクロペンテン、シクロヘキセン、及びノルボルネンなどの炭素数2以上のα-オレフィンコモノマー)との共重合体;前記コモノマーから選択される2種以上からなる共重合体;α-オレフィンモノマーと、酢酸ビニル、アクリル酸エステル、メタクリル酸エステルなどのコモノマーとの共重合体;α-オレフィンモノマーと芳香族ビニルモノマーなどのコモノマーとの共重合体又はその水素添加体;共役ジエンブロック共重合体又はその水素添加物等。なお、単に「共重合体」という場合は、ランダム共重合体であってもブロック共重合体であってもよい。
前記反応性基を有する変性オレフィン系重合体(A12)(重合体(A12))としては、重合時にオレフィンと反応性基を有する不飽和化合物とを共重合した共重合体(A12a)や、反応性基を有するラジカル重合性不飽和化合物をオレフィン系重合体にグラフト重合したグラフト重合体(A12b)等が挙げられる。
ポリオレフィン分散体(A)中に含まれる水以外の溶媒の比率は、該分散体全体に対して好ましくは50質量%以下であり、より好ましくは20質量%以下、さらに好ましくは10質量%以下である。水以外の溶媒の比率が10質量%以下であれば、貯蔵安定性に優れる傾向にある。また、水以外の溶媒としては、水に1質量%以上溶解する溶媒が好ましく、水に5質量%以上溶解する溶媒がより好ましい。そのような溶媒としては、例えば、メチルエチルケトン、シクロヘキサノン、n-プロパノール、イソプロパノール、n-ブタノール、イソブタノール、t-ブタノール、シクロヘキサノール、テトラヒドロフラン、2-メトキシエタノール、2-エトキシエタノール、2-ブトキシエタノール、2-メトキシプロパノール、2-エトキシプロパノールが挙げられる。これらは1種を単独で用いてもよいし、2種以上を組み合わせて用いてもよい。
ラジカル重合性単量体(B)としては、重合性に優れることからビニル系単量体が好ましい。ビニル系単量体としては、(メタ)アクリル酸、(メタ)アクリル酸エステルなどの(メタ)アクリル系単量体;スチレンやα-メチルスチレンなどの芳香族系単量体;(メタ)アクリルアミド、ジメチル(メタ)アクリルアミドなどのアミド系単量体;(メタ)アクリロニトリル、酢酸ビニル、プロピオン酸ビニル、バーサチック酸ビニル等が挙げられる。これらは1種を単独で用いてもよいし、2種以上を組み合わせて用いてもよい。なお、本発明の効果を著しく損なわない限り、ビニル系単量体は特に限定なく用いることができる。
乳化重合用界面活性剤(C)としては、各種のアニオン性、カチオン性、またはHLBが8以上のノニオン性の界面活性剤を用いることができる。また、界面活性剤成分中にエチレン性不飽和結合を持つ、いわゆる反応性界面活性剤も使用することができる。これらの中でも、得られる水性樹脂分散体の貯蔵安定性向上の点から、アニオン性の界面活性剤としては、特に限定されないが、例えば、反応性界面活性剤であるアデカリアソープSR(商品名、株式会社ADEKA製)や、非反応性界面活性剤のネオコールSW-C(商品名、第一工業製薬株式会社製)を用いることができる。
本発明において、前記ポリオレフィン分散体(A)はポリエーテル樹脂(D)を含有することが好ましい。すなわち、ポリオレフィン分散体(A)が、前記オレフィン重合体とポリエーテル樹脂(D)とを分散媒(水、及び/又は水以外の溶媒)に分散させて製造したものであることが好ましい。オレフィン重合体としては、オレフィン系重合体(A1)が好ましい。
本発明に係る水性樹脂分散体の製造方法は、ポリオレフィン分散体(A)、ラジカル重合性単量体(B)及び乳化重合用界面活性剤(C)を混合して重合する重合工程を含む。前記重合工程は、重合開始剤の添加時に前記ラジカル重合性単量体(B)の混合量(固形分)が、前記オレフィン分散体(A)の固形分質量部の0.5~2倍であり、前記乳化重合用界面活性剤(C)の固形分の混合量が、前記水性樹脂分散体の製造に用いるラジカル重合性単量体(B)の全量100質量部(固形分)に対して0~3質量部となるように各成分を混合する。
本発明では、さらに還元剤を添加して、レドックス系重合反応を行ってもよい。特に、重合安定性の観点から、重合開始剤として有機過酸化物類を用いて、還元剤として硫酸第一鉄とイソアスコルビン酸等を用いたレドックス系重合反応を行うことが好ましい。
1.初期密着性
水性樹脂分散体の固形分100部に対し、造膜助剤としてジエチレングリコールモノブチルエーテル60部、及び基材濡れ剤としてTEGO WET KL-245(EVONIK社製)3部を加え、ホモディスパー攪拌機(ポリトロンPT-3100)を用いて、700rpmにて5分間攪拌した。室温で一日放置した後、300メッシュを用いて濾過を行うことにより、水性塗料を得た。
○(Excellent):100マス中、剥離マスが0~19マスである。
△(Average):100マス中、剥離マスが20~80マスである。
×(Bad):100マス中、剥離マスが81~100マスである。
ガラス基板表面をイソプロピルアルコールで清拭した。該ガラス基板上に、得られた水性樹脂分散体を乾燥膜厚が100μmとなるように塗布した。そして、セーフベンドライヤー中、90℃の雰囲気で30分間乾燥させて塗膜を形成した。これを1日室温で静置し、ガラス基板から塗膜を剥離して、試験片を得た。
作製した試験片を10mm×10mmに切断し、質量(初期質量:W1)が0.2gとなるようにサンプル瓶に入れた。サンプル瓶に水100mlを投入した後、40℃で10日間恒温器にて保管した。保管後、試験片を取り出して質量(40℃10日間後の質量:W2)を測定し、質量減少率を以下の計算式より算出した。
質量減少率(%)={(W1(g)-W2(g))/W1(g))}×100
○(Excellent):質量減少率が4.00%未満
△(Average):質量減少率が4.00%以上、10.00%未満
×(Bad):質量減少率が10.00%以上
メタロセン触媒によって重合されたプロピレン-ブテン共重合体(オレフィン系重合体に相当)であるタフマー(登録商標)XM-7070(商品名、三井化学社製、融点:75℃、プロピレン含有量:74モル%、重量平均分子量(Mw):250,000(ポリプロピレン換算)、分子量分布(Mw/Mn):2.2)200kgと、無水マレイン酸5kgとをスーパーミキサーでドライブレンドした。その後、2軸押出機(商品名:TEX54αII、日本製鋼所社製)を用いて、前記プロピレン-ブテン共重合体100質量部に対して1質量部となるように、t-ブチルパーオキシイソプロピルモノカルボナート(重合開始剤、商品名:パーブチル(登録商標)I、日油社製)を、液添ポンプで途中フィードしながら、ニーディング部のシリンダー温度200℃、スクリュー回転数125rpm、吐出量80kg/時間の条件下で混練し、ペレット状の無水マレイン酸変性プロピレン-ブテン共重合体(グラフト重合体(A12b))を得た。得られた無水マレイン酸変性プロピレン-ブテン共重合体の物性を以下に示す。
無水マレイン酸基の含有量(グラフト率):1.0質量%(無水マレイン酸基として0.1mmol/g、カルボン酸基として0.2mmol/g)
重量平均分子量(Mw):156,000(ポリスチレン換算)
数平均分子量(Mn):84,000
還流冷却管、温度計及び攪拌機を備えたガラスフラスコ中に、製造例1で得られた無水マレイン酸変性プロピレン-ブテン共重合体50g、タフマー(登録商標)XM-7070 50g、及びトルエン50gを入れて、容器内を窒素ガスで置換し、110℃に昇温した。昇温後、無水マレイン酸2.0gを加え、さらにt-ブチルパーオキシイソプロピルモノカルボナート(商品名:パーブチル(登録商標)I、日油社製)1gを加え、7時間同温度で攪拌を続けて反応を行った。
得られた無水マレイン酸変性プロピレン-ブテン共重合体の無水マレイン酸基の含有量(グラフト率)は2.0質量%(無水マレイン酸基として0.2mmol/g、カルボン酸基として0.4mmol/g)であった。
反応終了後、系を室温付近まで冷却し、トルエン70gを加え、次いで、ポリエーテル樹脂(D)として、2-プロパノール90gに溶解したジェファーミン(登録商標)M-2005(商品名、ハンツマン社製、HLB:3、数平均分子量:2000、)を10g(無水マレイン酸変性プロピレンーブテン共重合体100質量部に対して20質量部に相当)加え、70℃で1時間反応させた。その後、ポリエーテル樹脂(D)として、2-プロパノール90gに溶解したジェファーミン(登録商標)M-1000(商品名、ハンツマン社製、HLB:17、数平均分子量:1000)を10g(無水マレイン酸変性プロピレンーブテン共重合体100質量部に対して10質量部に相当)加え、70℃で1時間反応させた。
その後、ジメチルエタノールアミン2g、水54gを加えて系内を中和した。得られた反応液の温度を45℃に保ち、加熱・撹拌し、水300gを滴下しながら、系内の減圧度を下げて、ポリマー濃度が30質量%になるまでトルエンと2-プロパノールを減圧留去した。以上により、平均粒子径70nmの乳白色のポリオレフィン分散体(A)を得た。ポリオレフィン分散体(A)の固形分は30質量%であった。
攪拌機、還流冷却管及び温度制御装置を備えたフラスコに、製造例2で得られたポリオレフィン分散体(A)を333.3部(固形分は100部)、脱イオン水を119.6部、及び乳化重合用界面活性剤(C)としてアデカリアソープSR-1025(商品名、株式会社ADEKA製、固形分25部)を8.0部(固形分は2部)仕込み、30℃に昇温した。次いで、ラジカル重合性単量体(B)として、アクリル酸ブチル100部を加え、50℃に昇温して1時間保持した。重合開始剤としてパーブチル(登録商標)H69(商品名、日油(株)製、固形分69質量%):0.02部と、還元剤として、硫酸第一鉄:0.0002部、エチレンジアミン四酢酸(EDTA):0.00027部、イソアスコルビン酸ナトリウム一水和物:0.08部、脱イオン水:1部を添加し、重合を開始した。
重合の発熱ピークを検出した後、パーブチル(登録商標)H690.03部及び脱イオン水10.0部を、15分間かけて滴下した。滴下終了後、60℃で30分間熟成し、水性樹脂分散体を得た。得られた水性樹脂分散体について、初期密着性及び耐水性の評価を行った。評価結果を表1に示した。
ポリオレフィン分散体(A)、ラジカル重合性単量体(B)、乳化重合用界面活性剤(C)及び重合開始剤並びにそれらの混合比を、表1に示すように変更した以外は、実施例1と同様にして水性樹脂分散体を得た。得られた水性樹脂分散体について、初期密着性及び耐水性の評価を行った。評価結果を表1に示した。
攪拌機、還流冷却管及び温度制御装置を備えたフラスコに、製造例2で得られたポリオレフィン分散体(A)333.3部(固形分は100部)、及び脱イオン水を28.5部仕込み、50℃に昇温して1時間保持した。次いで、還元剤として、硫酸第一鉄:0.0002部、エチレンジアミン四酢酸(EDTA):0.00027部、イソアスコルビン酸ナトリウム一水和物:0.08部、及び脱イオン水:1部を添加した後、ラジカル重合性単量体(B)としてアクリル酸ブチル:100.0部、乳化重合用界面活性剤(C)としてアデカリアソープSR-1025:16.0部(固形分4部)、及び脱イオン水:58.0部を含むプレ乳化液を2時間かけて滴下した。また、同時に、重合開始剤としてパーブチル(登録商標)H69:0.05部及び脱イオン水:45.0部を2.15時間かけて並列滴下して、重合した。滴下終了後、50℃で30分間熟成し、水性樹脂分散体を得た。得られた水性樹脂分散体について、初期密着性及び耐水性の評価を行った。評価結果を表1に示した。
乳化重合用界面活性剤(C)を表1に示すように変更した以外は、比較例1と同様にして水性樹脂分散体を得た。得られた水性樹脂分散体について、初期密着性及び耐水性の評価を行った。評価結果を表1に示した。
ハードレン(登録商標)EW5303:塩素化ポリオレフィン分散体、商品名、東洋紡社製
ネオコールSW-C:商品名、第一工業製薬社製
一方、比較例1では、重合開始剤添加時にポリオレフィン分散体(A)と、ポリオレフィン分散体(A)の固形分質量部の0.01倍のラジカル重合性単量体(B)を、滴下により重合させて水性樹脂分散体を製造した。そのため、得られた塗膜は、密着性及び耐水性が劣っていた。さらに、比較例3及び4の水性樹脂分散体は、乳化重合用界面活性剤(C)の固形分の混合割合が、ラジカル重合性単量体(B)に対し3質量%より多いため、得られた塗膜は、耐水性が劣っていた。
Claims (5)
- ポリオレフィンと、グリフィン法で計算されるHLBが1~8のポリエーテル樹脂(D)との分散物であるポリオレフィン分散体(A)、ラジカル重合性単量体(B)及び乳化重合用界面活性剤(C)を混合して重合する重合工程を含む水性樹脂分散体の製造方法であって、前記重合工程において、重合開始剤添加時に前記ラジカル重合性単量体(B)の混合量が、前記ポリオレフィン分散体(A)の固形分質量部の0.5~2倍であり、前記乳化重合用界面活性剤(C)の固形分の混合量が、前記ラジカル重合性単量体(B)の全量100質量部に対して0~3質量部である水性樹脂分散体の製造方法。
- 前記重合工程において、前記水性樹脂分散体の製造に用いる全てのラジカル重合性単量体(B)の50~100質量%を重合開始剤により一括重合する操作を含む請求項1に記載の水性樹脂分散体の製造方法。
- ポリオレフィンと、グリフィン法で計算されるHLBが1~8のポリエーテル樹脂(D)との分散物であるポリオレフィン分散体(A)及び乳化重合用界面活性剤(C)の存在下でラジカル重合性単量体(B)を重合する重合工程を含む水性樹脂分散体の製造方法であって、前記重合工程において、前記ラジカル重合性単量体(B)の混合量が、前記ポリオレフィン分散体(A)の固形分質量部の0.5~2倍であり、前記水性樹脂分散体の製造に用いる全てのラジカル重合性単量体(B)の50~100質量%を重合開始剤により一括重合する操作を含み、前記乳化重合用界面活性剤(C)の使用量が、前記水性樹脂分散体の製造に用いるラジカル重合性単量体(B)の全量100質量部に対して0~3質量部である水性樹脂分散体の製造方法。
- 前記ポリオレフィン分散体(A)がハロゲン原子を含有しない請求項1又は2に記載の水性樹脂分散体の製造方法。
- 前記水性樹脂分散体がプライマー用である請求項1~4のいずれか一項に記載の水性樹脂分散体の製造方法。
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