JP7129481B2 - 水性分散体、その製造方法、塗料組成物及び塗膜 - Google Patents
水性分散体、その製造方法、塗料組成物及び塗膜 Download PDFInfo
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- 239000010959 steel Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 238000009864 tensile test Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- WFEZEFHULWPUDG-UHFFFAOYSA-N triazanium 2-methylprop-2-enoate sulfate Chemical compound [NH4+].[NH4+].[NH4+].[O-]S([O-])(=O)=O.CC(=C)C([O-])=O WFEZEFHULWPUDG-UHFFFAOYSA-N 0.000 description 1
- GQIUQDDJKHLHTB-UHFFFAOYSA-N trichloro(ethenyl)silane Chemical compound Cl[Si](Cl)(Cl)C=C GQIUQDDJKHLHTB-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940117013 triethanolamine oleate Drugs 0.000 description 1
- SOUMBTQFYKZXPN-UHFFFAOYSA-N trimethoxy(4-phenylbut-3-enyl)silane Chemical compound CO[Si](OC)(OC)CCC=CC1=CC=CC=C1 SOUMBTQFYKZXPN-UHFFFAOYSA-N 0.000 description 1
- FZGFBJMPSHGTRQ-UHFFFAOYSA-M trimethyl(2-prop-2-enoyloxyethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CCOC(=O)C=C FZGFBJMPSHGTRQ-UHFFFAOYSA-M 0.000 description 1
- 229960004418 trolamine Drugs 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 239000005050 vinyl trichlorosilane Substances 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
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Description
R1-O-(R2O)nSO3X (S)
(式中、R1は炭素数8~20の脂肪族炭化水素基であり、R2は炭素数2~4のアルキレン基であり、nは2~15であり、Xは、一価のカチオンを表す。)
R1-O-(R2O)nSO3X (S)
(式中、R1は炭素数8~20の脂肪族炭化水素基であり、R2は炭素数2~4のアルキレン基であり、nは2~15であり、Xは、一価のカチオンを表す。)
で表される硫酸エステル化合物を含有する水性分散体の製造方法であって、付加重合性オキサゾリンを含有する単量体混合物を、硫酸エステル化合物を含有する界面活性剤の存在下で乳化重合を行う重合体(A)の製造工程を備える。
R1-O-(R2O)nSO3X (S)
(式中、R1は炭素数8~20の脂肪族炭化水素基であり、R2は炭素数2~4のアルキレン基であり、nは2~15であり、Xは、一価のカチオンを表す。)
で表される硫酸エステル化合物を含有する。
R1-O-(R2O)nSO3X (S)
(式中、R1は炭素数8~20の脂肪族炭化水素基であり、R2は炭素数2~4のアルキレン基であり、nは2~15であり、Xは、一価のカチオンを表す。)
で表される硫酸エステル化合物と、カルボキシル基を有する重合体(B)とを含む。
R1-O-(R2O)nSO3X (S)
(式中、R1は炭素数8~20の脂肪族炭化水素基であり、R2は炭素数2~4のアルキレン基であり、nは2~15であり、Xは、一価のカチオンを表す。)
2-オキサゾリン基を有する重合体としては、2-オキサゾリン基を有する構造単位を含有する重合体であれば制限はなく、2-オキサゾリン基を有する構造単位としては、1種のみが含まれていてもよく、2種以上が含まれていてもよい。また、当該重合体は、2-オキサゾリン基を有しないその他の構造単位を含有していてもよい。なお、以下、2-オキサゾリン基を有する重合体を重合体(A)とも呼ぶ。
重合体(A)の重量平均分子量としては、100000~5000000g/molであることが好ましく、300000~3000000g/molであることがより好ましい。重量平均分子量は、ゲル濾過クロマトグラフィー(GPC)により測定することができる。重量平均分子量は、例えば、以下の測定条件で測定する。
測定機器:HLC-8120GPC(商品名、東ソー社製)
分子量カラム:TSK-GEL GMHXL-Lと、TSK-GELG5000HXL(いずれも東ソー社製)とを直列に接続して使用
溶離液:テトラヒドロフラン(THF)
検量線用標準物質:ポリスチレン(東ソー社製)
測定方法:測定対象物を固形分が約0.2質量%となるようにTHFに溶解し、フィルターにてろ過したものを測定サンプルとして分子量を測定する。
また、重合体(A)を含む水性分散体の場合、水性分散体に含まれるエマルション粒子は、重合体(A)および界面活性剤を含むが、上記重合体(A)同士が、例えば架橋剤等により結合(架橋)された架橋体を有してもよい。重合体(A)が架橋体を有する場合、その重量平均分子量を測定することは困難であるため、重合体(A)の重量平均分子量の上限値は、特に限定されない。
上記計算式(1)により重合性単量体成分のガラス転移温度(Tg)を算出するのに使用する、代表的なホモポリマーのTg値を下記に示す。
メチルメタクリレート(MMA):105℃
スチレン(St):100℃
ブチルアクリレート(BA):-56℃
2-エチルヘキシルアクリレート(2EHA):-70℃
アクリル酸(AA):95℃
2-イソプロペニルー2-オキサゾリン:100℃
本実施形態の硫酸エステル化合物は、下記化学式(S)で表される。
R1-O-(R2O)nSO3X (S)
式中、R1は、炭素数8~20の脂肪族炭化水素基であり、直鎖又は分岐鎖の脂肪族炭化水素基であることが好ましい。また、R1としては、一般式CmH2m+1で表されるアルキル基であることが好ましく、mは、8~20であることが好ましく、10~18であることがより好ましく、10~16であることが更に好ましく、11~15であることがより更に好ましく、12~14であることが特に好ましい。具体的には、オクチル基、ノニル基、デシル基、ウンデシル基、ドデシル基、トリデシル基、テトラデシル基、ペンタデシル基、ヘキサデシル基、ヘプタデシル基、ノナデシル基、イコシル基等が挙げられる。また、R1は、一つ以上の不飽和二重結合を有する直鎖又は分岐鎖の脂肪族炭化水素基であってよく、一つの不飽和二重結合を有する直鎖又は分岐鎖の脂肪族炭化水素基であってよい。そのようなR1としては、具体的には、オレイル基等が挙げられる。
本開示の水性分散体は、重合体(A)および硫酸エステル化合物を含む。水性分散体における重合体(A)の含有量は水性分散体の総量に対して、1~80質量%であることが好ましく、5~60質量%であることがより好ましく、10~50質量%であることが更に好ましい。本開示の水性分散体は、効果を阻害しない範囲において、重合体(A)以外の成分を含むことができる。また、本開示の水性分散体における不揮発分の含有量は、水性分散体の総量に対して、1~80質量%であることが好ましく、5~60質量%であることがより好ましく、10~50質量%であることが更に好ましい。
重合体(A)を含む水性分散体は、付加重合性オキサゾリン(a)及び必要に応じて少なくとも1種の他の単量体(b)を、従来公知の重合法によって水性媒体中で重合を行うことにより製造することができる。より具体的には、本実施形態の水性分散体は、付加重合性オキサゾリンを含有する単量体混合物を、上記硫酸エステル化合物を含有する界面活性剤の存在下で乳化重合を行う工程(重合体(A)の製造工程)を備える製造方法によって製造できる。乳化重合は、界面活性剤を含む水溶液に単量体混合物を添加して得られたプレエマルションに対して行ってもよいし、界面活性剤を含む水溶液に単量体混合物を滴下しながら行ってもよい。上記硫酸エステル化合物を用いると、単量体混合物の乳化が容易であると共に、上記硫酸エステル化合物の存在下で乳化重合を行うと、重合中に生じる凝集物の量が少なく、安定して乳化重合が行える傾向にある。使用することができる水性媒体は、特に制限はないが、例示すれば、水;又は、水とメタノール、エタノール、プロパノール、イソプロパノール、ブタノール、ターシャリーブタノール、エチレングリコール、エチレングリコールモノメチルエーテル、エチレングリコールモノブチルエーテル、ジエチレングリコール、アセトン、メチルエチルケトン等の有機溶媒との混合溶液が挙げられる。
R1-O-(R2O)nSO3X (S)
(式中、R1は炭素数8~20の脂肪族炭化水素基であり、R2は炭素数2~4のアルキレン基であり、nは2~15であり、Xは、一価のカチオンを表す。)
で表される硫酸エステル化合物と、カルボキシル基を有する重合体(B)と、を含む。乾燥する際に加熱してもよく、100~140℃で5~60分の加熱乾燥を行ってもよい。乾燥する際の雰囲気としては、特に限定されないが、60~70%の相対湿度の雰囲気であってよい。
攪拌機、還流冷却器、窒素導入管、温度計及び滴下ロートを備えたフラスコに、脱イオン水782.4質量部及び表1に記載された界面活性剤18.7質量部〔2-オキサゾリン基を有する重合体を形成する単量体混合物の質量(該重合体の質量に相当)に対し、2.9質量%〕を仕込み、適量の28質量%アンモニア水でpH9.0に調整し、ゆるやかに窒素ガスを流しながら70℃に加熱した。そこへ過硫酸カリウムの5質量%水溶液64質量部を注入し、続いて予め調製しておいたアクリル酸ブチル288質量部、スチレン288質量部、2-イソプロペニル-2-オキサゾリン64質量部及びジビニルベンゼン6質量部からなる単量体混合物を3時間にわたって滴下しながら、重合反応を行った。反応中は窒素ガスを吹き込み続け、フラスコ内の温度を70±1℃に保った。滴下終了後も2時間同じ温度に保った後、内温を80℃に昇温させて1時間攪拌を続けて反応を完結させた。その後冷却し、300のメッシュの金網で濾過し、凝集物を分離し、pH8.0の2-オキサゾリン基を有する重合体の水性分散体を得た。不揮発分量を測定したところ、43.5質量%であった。重合体のガラス転移温度をFox式で見積もったところ、10℃であった。また、動的光散乱法による粒度分布測定器(Particle Sizing Systems社製「NICOMP Model 380」)を用い、水性分散体に含まれるエマルション粒子の平均粒子径(体積平均粒子径)を測定した。結果を表1に示す。
<比較例3(2-オキサゾリン基を有する重合体の製造)>
表1に記載された界面活性剤25.8質量部〔2-オキサゾリン基を有する重合体を形成する単量体混合物の質量(該重合体の質量に相当)に対し、4.0質量%〕を仕込む以外は、実施例1と同様の方法で製造した。不揮発分量を測定したところ、43.5質量%であった。重合体のガラス転移温度をFox式で見積もったところ、10℃であった。また、動的光散乱法による粒度分布測定器(Particle Sizing Systems社製「NICOMP Model 380」)を用い、水性分散体に含まれるエマルション粒子の平均粒子径(体積平均粒子径)を測定した。結果を表1に示す。
得られた各水性分散体に対して、以下の条件でマロン機械的安定性試験を行った。試験機としては、株式会社安田精機製作所製、商品名:「No.156マロン機械的安定度試験機」を使用した。試験後、100メッシュの金網により試料を濾過し、回収された凝集物の質量を測定した。試験に使用した試料の量に対する得られた凝集物の質量を計算し、凝集率を求めた。結果を表1に示す。凝集率が小さいほど機械的安定性に優れている。
(試験条件)
サンプル量:70g
負荷 :10kg
回転数 :1000rpm
試験時間 :10分
フラスコに、脱イオン水782.4質量部及び実施例1、2、及び比較例1~3で使用した各界面活性剤を一定量(脱イオン水及び単量体混合物の総量に対して3質量%)添加した水溶液を用意した。当該水溶液に、上記単量体混合物と同じ組成の単量体混合物を添加した際の乳化しやすさを以下の基準で評価した。
A:単量体混合物を一括して添加し、回転数300rpmで15分攪拌して乳化できた。
B:単量体混合物を一括して添加すると乳化できないが、単量体混合物を10回に分けて添加し、添加するごとに回転数300rpmで15分攪拌した場合であれば、乳化可能であった。
C:乳化できなかった。
乳化重合の直後に分離した凝集物の質量を測定し、水性分散体の総量に対する割合(%)を算出し、以下の基準で評価した。結果を表1に示す。
A:凝集物量が0.2%未満
B:凝集物量が0.2~1.0%
C:凝集物量が1.0%より大きい
LA-10:第一工業製薬株式会社製、商品名「ハイテノール LA-10」、化学式(S)において、R1:ラウリル、R2:エチレン、n=4、X:NH4の化合物。
08E :第一工業製薬株式会社製、商品名「ハイテノール 08E」、化学式(S)において、R1:オレイル、R2:エチレン、n=8、X:NH4の化合物。
LA-16:第一工業製薬株式会社製、商品名「ハイテノール LA-16」、化学式(S)において、R1:ドデシル、R2:エチレン、n=16、X:NH4の化合物。
E-1000A:花王株式会社製、商品名「ラムテル E-1000A」、下記化学式の多環芳香族化合物。
攪拌機、還流冷却器、窒素導入管、温度計及び滴下ロートを備えたフラスコに、脱イオン水376.5質量部及びハイテノールN-08(第一工業製薬株式会社製、ポリオキシエチレンノニルフェニルエーテル硫酸アンモニウム塩の15質量%水溶液)70.8質量部を仕込み、ゆるやかに窒素ガスを流しながら80℃に加熱した。予め調製しておいたアクリル酸2-エチルヘキシル131質量部、スチレン205質量部及びアクリル酸17質量部からなる単量体混合物の5質量%をフラスコに仕込み、続いて過硫酸カリウムの5質量%水溶液21質量部を注入し重合を開始した。10分後に残りの単量体混合物を3時間にわたって滴下した。反応中は窒素ガスを吹き込み続け、フラスコ内の温度を80±1℃に保った。滴下終了後も1時間同じ温度に保った後、冷却し、25質量%アンモニア水9質量部でpH8.5に調整し、不揮発分44.1質量%、pH8.5のアクリルエマルションを(重合体(B))得た。
各クリア塗料を、温度が23±2℃で、相対湿度が65±3%である雰囲気中でガラス板(縦:15cm、横:7cm)上に乾燥後の膜厚が150μmになるようにアプリケーターを用いて塗布した。このガラス板をこの雰囲気中で2分間放置し、次いで120℃の温度で30分間加熱した後、放冷することにより、塗膜が形成されたガラス板を作製した。
上記塗膜を、メチルエチルケトンを含ませた脱脂綿で50往復して擦った後(ラビング試験)、その塗膜の状態を目視で観察し、以下の評価基準に基づいて評価した。なお、塗膜に変化がないほど架橋性が良好である。
A:塗膜に変化が認められない。
B:塗膜の一部に溶解が認められる。
C:塗膜全体に溶解が認められる。
耐溶剤性試験と同様にして塗膜が形成されたガラス板を作製した。この塗膜が形成されたガラス板の塗膜上に直径30mm、長さ30mmのガラス管の開口部を載せて接着させた後、ガラス管の内部にある塗膜が水と接触するようにイオン交換水10mLをガラス管内に注いだ状態で、温度が23±2℃で、相対湿度が65±3%である雰囲気中に24時間放置した。その後、イオン交換水と接触している塗膜の状態を目視で観察し、以下の評価基準に基づいて評価した。なお、試験開始前の塗膜と比較して試験後の塗膜に変化が小さいほど架橋性が良好である。
(評価基準)
A:塗膜に変化が認められない。
B:塗膜の一部にやや白濁が認められる。
C:塗膜全体に白化が認められる。
耐溶剤性試験で用いた塗膜が形成されたガラス板から、カッターの刃で塗膜を剥ぎ取り、その剥ぎ取った塗膜(遊離フィルム)を強度測定用フィルムとした。強度測定用フィルムを恒温恒湿室(温度25℃、湿度60%RH)で24時間保存した。その後、引っ張り試験機〔株式会社島津製作所製、商品名:オートグラフAGS-100D〕のチャックに掴持し、JIS P-8113に準拠して引っ張り試験し、強度測定用フィルムの引張強度を測定した。製造例1で製造したアクリルエマルションのクリア塗料(実施例1、2及び比較例1~3の水性分散体を配合していない塗料)から形成したフィルムの引張強度をブランクとし、そのブランクと実施例1、2及び比較例1~3の水性分散体を配合した各クリア塗料から形成したフィルムとの引張強度を比較した。結果を以下の基準で評価した。
A:ブランクと比較して強度が1.5倍より大きくなった。
B:ブランクと比較して強度が1.0~1.5倍であった。
水性分散体に含まれる2-オキサゾリン基を有する重合体のモノマー組成、又は水性分散体に含まれる添加剤(防腐剤若しくは乳化剤)の種類若しくは含有量を表3に示すとおりに変更した以外は、実施例1と同様に水性分散体を製造し、各種性能評価を行った。結果を表3に示す。なお、表3における略号は、以下のとおりである。
ST:スチレン
BA:アクリル酸ブチル
DVB:ジビニルベンゼン
IPO:2-イソプロペニル-2-オキサゾリン
MMA:メチルメタクリレート
BIT:ベンゾイソチアゾリン(ロンザジャパン株式会社製、商品名:Proxel GXL、ベンゾイソチアゾリンの含有量:20質量%)
Claims (10)
- 2-オキサゾリン基を有する重合体(A)を含有するエマルション粒子と、
界面活性剤と、を含み、
前記界面活性剤が、以下の化学式(S)で表される硫酸エステル化合物を含有し、
前記硫酸エステル化合物の含有量は、前記重合体(A)の総量に対して、0.5~10質量%である、水性分散体。
R1-O-(R2O)nSO3X (S)
(式中、R1は炭素数8~20の脂肪族炭化水素基であり、R2は炭素数2~4のアルキレン基であり、nは2~15であり、Xは、一価のカチオンを表す。) - 前記水性分散体に含まれる界面活性剤の総量に対する前記硫酸エステル化合物の割合が50~100質量%である、請求項1に記載の水性分散体。
- イソチアゾリン系化合物を更に含む、請求項1又は2に記載の水性分散体。
- 前記重合体(A)の総量に対して、10~5000質量ppmの前記イソチアゾリン系化合物を含む、請求項3に記載の水性分散体。
- 前記イソチアゾリン系化合物がベンゾイソチアゾリンを含む、請求項3又は4に記載の水性分散体。
- 前記重合体(A)は、当該重合体の総質量に対して、オキサゾリン基を有する構造単位を0.5~50質量%含む、請求項1~5のいずれか一項に記載の水性分散体。
- 前記重合体(A)は、当該重合体の総質量に対して、オキサゾリン基を有する構造単位を5~40質量%含む、請求項1~6のいずれか一項に記載の水性分散体。
- 2-オキサゾリン基を有する重合体(A)と、界面活性剤と、を含み、
前記界面活性剤が、以下の化学式(S);
R1-O-(R2O)nSO3X (S)
(式中、R1は炭素数8~20の脂肪族炭化水素基であり、R2は炭素数2~4のアルキレン基であり、nは2~15であり、Xは、一価のカチオンを表す。)
で表される硫酸エステル化合物を含有する水性分散体の製造方法であって、
付加重合性オキサゾリンを含有する単量体混合物を、前記硫酸エステル化合物を含有する界面活性剤の存在下で乳化重合を行う、重合体(A)の製造工程を備える、水性分散体の製造方法。 - 水性分散体及びカルボキシル基を有する重合体(B)を含み、
前記水性分散体が、
2-オキサゾリン基を有する重合体(A)と、
界面活性剤と、を含み、
前記界面活性剤が、以下の化学式(S);
R1-O-(R2O)nSO3X(S)
(式中、R1は炭素数8~20の脂肪族炭化水素基であり、R2は炭素数2~4のアルキレン基であり、nは2~15であり、Xは、一価のカチオンを表す。)
で表される硫酸エステル化合物を含有する、塗料組成物。 - 2-オキサゾリン基を有する重合体(A)と、
化学式(S);
R1-O-(R2O)nSO3X (S)
(式中、R1は炭素数8~20の脂肪族炭化水素基であり、R2は炭素数2~4のアルキレン基であり、nは2~15であり、Xは、一価のカチオンを表す。)
で表される硫酸エステル化合物と、
カルボキシル基を有する重合体(B)と、を含む、塗膜。
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- 2019-08-06 CN CN201980051547.5A patent/CN112543792A/zh active Pending
- 2019-08-06 EP EP19847298.7A patent/EP3835368A4/en active Pending
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- 2019-08-06 WO PCT/JP2019/030988 patent/WO2020032063A1/ja unknown
- 2019-08-06 US US17/265,598 patent/US20220275152A1/en active Pending
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JPWO2020032063A1 (ja) | 2021-08-10 |
KR20210041030A (ko) | 2021-04-14 |
WO2020032063A1 (ja) | 2020-02-13 |
EP3835368A1 (en) | 2021-06-16 |
US20220275152A1 (en) | 2022-09-01 |
EP3835368A4 (en) | 2022-05-18 |
KR102520999B1 (ko) | 2023-04-13 |
TW202017955A (zh) | 2020-05-16 |
CN112543792A (zh) | 2021-03-23 |
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