JPS6362244B2 - - Google Patents
Info
- Publication number
- JPS6362244B2 JPS6362244B2 JP59178213A JP17821384A JPS6362244B2 JP S6362244 B2 JPS6362244 B2 JP S6362244B2 JP 59178213 A JP59178213 A JP 59178213A JP 17821384 A JP17821384 A JP 17821384A JP S6362244 B2 JPS6362244 B2 JP S6362244B2
- Authority
- JP
- Japan
- Prior art keywords
- parts
- paint
- polymerization
- present
- antifoaming
- 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.)
- Expired
Links
- 239000002518 antifoaming agent Substances 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 10
- 230000003254 anti-foaming effect Effects 0.000 claims description 8
- 229920001577 copolymer Polymers 0.000 claims description 4
- 229920001519 homopolymer Polymers 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000003973 paint Substances 0.000 description 14
- 238000006116 polymerization reaction Methods 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000004519 manufacturing process Methods 0.000 description 8
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- -1 ethylhexyl Chemical group 0.000 description 5
- 229920001296 polysiloxane Polymers 0.000 description 5
- 239000008096 xylene Substances 0.000 description 5
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000004342 Benzoyl peroxide Substances 0.000 description 3
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- 235000019400 benzoyl peroxide Nutrition 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 229910001873 dinitrogen Inorganic materials 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000006260 foam Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000004925 Acrylic resin Substances 0.000 description 2
- 229920000178 Acrylic resin Polymers 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 229920000180 alkyd Polymers 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000005187 foaming Methods 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 239000000976 ink Substances 0.000 description 2
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 238000010422 painting Methods 0.000 description 2
- 235000012424 soybean oil Nutrition 0.000 description 2
- 239000003549 soybean oil Substances 0.000 description 2
- 229920003002 synthetic resin Polymers 0.000 description 2
- 239000000057 synthetic resin Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 2
- JHPBZFOKBAGZBL-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylprop-2-enoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)=C JHPBZFOKBAGZBL-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- JLPULHDHAOZNQI-ZTIMHPMXSA-N 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC JLPULHDHAOZNQI-ZTIMHPMXSA-N 0.000 description 1
- WYGWHHGCAGTUCH-UHFFFAOYSA-N 2-[(2-cyano-4-methylpentan-2-yl)diazenyl]-2,4-dimethylpentanenitrile Chemical compound CC(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)C WYGWHHGCAGTUCH-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 description 1
- NKFIBMOQAPEKNZ-UHFFFAOYSA-N 5-amino-1h-indole-2-carboxylic acid Chemical compound NC1=CC=C2NC(C(O)=O)=CC2=C1 NKFIBMOQAPEKNZ-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 235000019484 Rapeseed oil Nutrition 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- 125000005396 acrylic acid ester group Chemical group 0.000 description 1
- CEGOLXSVJUTHNZ-UHFFFAOYSA-K aluminium tristearate Chemical compound [Al+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CEGOLXSVJUTHNZ-UHFFFAOYSA-K 0.000 description 1
- 229940063655 aluminum stearate Drugs 0.000 description 1
- 239000006265 aqueous foam Substances 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- 239000012969 di-tertiary-butyl peroxide Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 1
- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [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])* 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 239000005453 ketone based solvent Substances 0.000 description 1
- GIWKOZXJDKMGQC-UHFFFAOYSA-L lead(2+);naphthalene-2-carboxylate Chemical compound [Pb+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 GIWKOZXJDKMGQC-UHFFFAOYSA-L 0.000 description 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 231100000989 no adverse effect Toxicity 0.000 description 1
- ZWWQICJTBOCQLA-UHFFFAOYSA-N o-propan-2-yl (propan-2-yloxycarbothioyldisulfanyl)methanethioate Chemical compound CC(C)OC(=S)SSC(=S)OC(C)C ZWWQICJTBOCQLA-UHFFFAOYSA-N 0.000 description 1
- HMZGPNHSPWNGEP-UHFFFAOYSA-N octadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C(C)=C HMZGPNHSPWNGEP-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 229940083466 soybean lecithin Drugs 0.000 description 1
- 235000015096 spirit Nutrition 0.000 description 1
- 230000002194 synthesizing effect Effects 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
- 238000012360 testing method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-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
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
Description
産業上の利用分野
本発明はアクリル酸エステルあるいはメタクリ
ル酸エステルのホモポリマー又はコポリマー及び
該成分を溶解しうる溶剤からなる新規な消泡剤で
発泡性傾向を有する非水系の泡の防止又は抑制の
ために有効な消泡剤に関する。
従来の技術
従来、合成樹脂、塗料、インキ、接着剤の製造
加工工程において、発泡現象が作業を進める上で
種々の障害をもたらしている。例えば、塗料工業
においては、製造工程（顔料分散時）で空気を巻
き込むと塗料中に泡が細かく拡散され、これを除
去する事が困難となり、単に製造時の作業性の問
題のみならず、最終製品の品質にも致命的な影響
を及ぼす。又、ローラー塗装、ハケ塗装などの施
工時に、気泡の巻き込みによる泡の残存で、塗膜
の状態を悪化させ、種々のトラブルの原因とな
る。この泡による障害を防止あるいは抑制するた
め、非水系においては、従来、主にシリコーン系
消泡剤が使用されてきた。
発明が解決しようとする問題点
しかしながら、シリコーン系消泡剤は、通常、
消泡力、消泡作用の持続性などの消泡性能は優れ
ているが、高価格のため、一般的な使用には問題
がある。又、もう一方の欠点として、塗料製造時
にシリコーン系消泡剤を用いると、塗料成分との
相溶性が悪いため、ゆず肌、フイツシユアイ現象
が起こり易く、又重ね塗りにおける接着性を低下
させる事も知られている。
しかして、本発明者らは、これら従来の消泡剤
の欠点を解消すべく鋭意研究の結果、本発明に到
達したものである。
問題点を解決するための手段
本発明は、即ち、下記一般式
〔上式中、R1及びR2は、それぞれ独立に、炭素
数１〜22の直鎖又は分枝鎖状のアルキル基を表わ
し、ｍ及びｎは、それぞれ独立に、０又は１以上
であつて、合計で30〜1200の整数を表わす〕
で示されるホモポリマー又はコポリマーの１種又
は２種以上の混合物を適当な溶剤に溶解させてな
る非水系抑泡型消泡剤組成物を提供する。上記一
般式のポリマーにおいて、ｍ個のR1とｎ個のR2
は、それぞれ、前記炭素数１〜22のアルキル基の
２種又はそれ以上の混合物であつてよいことを理
解されたい。
上記一般式におけるR1、R2としては、例えば、
メチル、エチル、ｎ−プロピル、iso−プロピル、
ｎ−ブチル、iso−ブチル、tert−ブチル、２−
エチルヘキシル、ラウリル、トリデシル、ステア
リルベヘニル基の様な炭素数１〜22のアルキル基
があり、重合度（ｍ＋ｎ）は30〜1200の範囲であ
るのが特に効果において優れる。分子量の小さい
場合には界面での吸着力が弱いため十分な効果が
得られず、分子量の大きい場合には拡散性が弱い
ため効果が劣る。溶剤としては、ベンゼン、トル
エン、キシレン、エチルベンゼン等の芳香族系溶
剤、ｎ−ヘキサン、ｎ−ヘプタン、シクロヘキサ
ン、ケロシン、鉱物油等の炭化水素系溶剤、四塩
化炭素、トリクロルエチレン、パークロルエチレ
ン等の塩素系溶剤、テトラヒドロフラン、ジオキ
サン等のエーテル系溶剤、メチルエチルケトン、
メチルイソブチルケトン等のケトン系溶剤、綿実
油、ナタネ油、大豆油、ヒマシ油等の植物油系溶
剤が挙げられる。これらの溶剤は、一般式のホモ
ポリマー又はコポリマーを合成する時の重合溶媒
として使用されてもよく、もしくは反応後の稀釈
溶剤として使用されてもよい。
本発明における一般式のポリマーの一般的な製
造方法においては、アクリル酸エステル又はメタ
クリル酸エステルモノマーを、上記溶剤を重合溶
媒とし、ラジカル重合開始剤、例えば、ベンゾイ
ルパーオキサイド、ラウロイルパーオキサイド、
ジ−ターシヤリブチルパーオキサイド等の有機過
酸化物、あるいは２，2′−アゾビスイソブチロニ
トリル、２，2′−アゾビス（２，４−ジメチルバ
レロニトリル）等のアゾ化合物を用いて所定の条
件で重合反応を行なう。又、重合度調整のため、
メルカプタン類、芳香族ニトロ化合物、チオグリ
コール酸、ジイソプロピルジキサントゲン等の重
合抑制剤を使用する。重合は、ブロツク重合でも
ランダム重合でもよい。
発明の効果
本発明の消泡剤組成物を使用することにより、
合成樹脂、塗料、インキ、接着剤の製造加工工程
に於て、発泡現象を大巾に抑制し、気泡の持ち込
みも少なく、泡による障害を大巾に減少させるこ
とが可能となる。また、本発明の消泡剤組成物
は、シリコン系消泡剤と比較しても消泡効果に優
れ、シリコン系消泡剤の欠点であるハジキ現象や
塗膜への悪影響も全くなく、非常に優れた品質の
製品を与える。
実施例
次に、例をもつて本発明を更に説明する。尚、
例中、部は重量部を示す。
製造例 １
四つ口フラスコに、メタクリル酸ｎ−ブチル
100部、溶媒としてトルエン200部、触媒として
２，2′−アゾビスイソブチロニトリル0.1部をと
り、窒素ガス気流下、70〜80℃で５時間重合反応
を行なつた所、淡黄色の粘稠な液体が得られた。
この重合体の分子量は、GPC測定で約32000であ
つた（本発明品）。
製造例 ２
四つ口フラスコに、メタクリル酸２−エチルヘ
キシル80部、アクリル酸ｎ−ブチル20部、溶媒と
してトルエン200部、触媒として２，2′−アゾビ
スイソブチロニトリル0.2部をとり、窒素ガス気
流下、70〜80℃で４時間重合反応を行なつた所、
分子量約21500の淡黄色の粘稠な液体が得られた
（本発明品）。
製造例 ３
四つ口フラスコに、メタクリル酸ラウリル90
部、メタクリル酸メチル10部、溶媒としてキシレ
ン100部、触媒としてベンゾイルパーオキサイド
0.1部、重合抑制剤としてラウリルメルカプタン
0.02部をとり、窒素ガス気流下、80〜90℃で４時
間重合反応を行ない、冷却後鉱物油100部を加え
て稀釈した。分子量約85000の淡黄色粘稠液体が
得られた（本発明品）。
製造例 ４
四つ口フラスコに、メタクリル酸ブチル75部、
メタクリル酸ステアリル25部、溶媒としてキシレ
ン150部、触媒としてベンゾイルパーオキサイド
0.2部をとり、窒素ガス気流下、80〜90℃で５時
間重合を行ない、冷却後キシレン50部を加えて稀
釈した。分子量が約115000の淡黄色粘稠液体であ
つた（本発明品）。
実施例 １
消泡剤として本発明品および比較品を用いて、
下記配合により、アクリル樹脂塗料を作成した。
そして、この塗料20ｇ及びシンナー10ｇを共栓試
験管（直径25mm×長さ200mm）に取り、30秒間上
下に激しく振盪の後、液表面及び液内部の泡の消
失時間を測定した。その結果を表１に示すが、本
発明品は消泡性、抑泡性ともにすぐれている。塗料配合
熱可塑性アクリル樹脂（60％） 80 部
トルエン 10 部
キシレン 6 部
ブタノール 3 部
ブチルセロソルブ 1 部
消泡剤 0.1部
Industrial Application Field The present invention is a novel antifoaming agent comprising a homopolymer or copolymer of acrylic acid ester or methacrylic acid ester and a solvent capable of dissolving the components, and is useful for preventing or suppressing non-aqueous foams having a tendency to foam. It relates to an antifoaming agent effective for. BACKGROUND OF THE INVENTION Conventionally, in the manufacturing and processing processes of synthetic resins, paints, inks, and adhesives, foaming phenomena have caused various problems in the progress of the work. For example, in the paint industry, when air is introduced during the manufacturing process (during pigment dispersion), bubbles are finely dispersed in the paint, making it difficult to remove. It also has a fatal impact on product quality. Furthermore, during construction such as roller painting or brush painting, residual bubbles caused by entrainment of air bubbles deteriorate the condition of the paint film and cause various troubles. In order to prevent or suppress problems caused by foam, silicone antifoaming agents have conventionally been mainly used in non-aqueous systems. Problems to be Solved by the Invention However, silicone antifoaming agents usually
Although it has excellent antifoaming properties such as antifoaming power and durability of antifoaming action, it has problems in general use due to its high price. Another drawback is that when silicone antifoaming agents are used during paint manufacturing, they have poor compatibility with paint components, which tends to cause orange peel and hard eye phenomena, and can also reduce adhesion in repeated coatings. Are known. As a result of intensive research aimed at solving the drawbacks of these conventional antifoaming agents, the present inventors have arrived at the present invention. Means for Solving the Problems The present invention is based on the following general formula: [In the above formula, R 1 and R 2 each independently represent a straight or branched alkyl group having 1 to 22 carbon atoms, and m and n each independently represent 0 or 1 or more; and the total represents an integer of 30 to 1,200] A non-aqueous antifoaming antifoaming agent composition is provided by dissolving one or a mixture of two or more homopolymers or copolymers represented by the following in an appropriate solvent. . In the polymer of the above general formula, m R 1 and n R 2
It is to be understood that each of may be a mixture of two or more of the above C1-C22 alkyl groups. As R 1 and R 2 in the above general formula, for example,
Methyl, ethyl, n-propyl, iso-propyl,
n-butyl, iso-butyl, tert-butyl, 2-
There are alkyl groups having 1 to 22 carbon atoms such as ethylhexyl, lauryl, tridecyl, and stearylbehenyl groups, and those having a degree of polymerization (m+n) of 30 to 1200 are particularly effective. When the molecular weight is small, the adsorption force at the interface is weak, so a sufficient effect cannot be obtained, and when the molecular weight is large, the diffusivity is weak, so the effect is inferior. Examples of solvents include aromatic solvents such as benzene, toluene, xylene, and ethylbenzene, hydrocarbon solvents such as n-hexane, n-heptane, cyclohexane, kerosene, and mineral oil, carbon tetrachloride, trichloroethylene, perchlorethylene, etc. Chlorinated solvents, ether solvents such as tetrahydrofuran and dioxane, methyl ethyl ketone,
Examples include ketone solvents such as methyl isobutyl ketone, vegetable oil solvents such as cottonseed oil, rapeseed oil, soybean oil, and castor oil. These solvents may be used as a polymerization solvent when synthesizing a homopolymer or copolymer of the general formula, or as a dilution solvent after the reaction. In the general method for producing a polymer of the general formula in the present invention, an acrylic ester or methacrylic ester monomer is used as a polymerization solvent, and a radical polymerization initiator, such as benzoyl peroxide, lauroyl peroxide,
Specified organic peroxides such as di-tertiary butyl peroxide, or azo compounds such as 2,2'-azobisisobutyronitrile and 2,2'-azobis(2,4-dimethylvaleronitrile) are used. The polymerization reaction is carried out under the following conditions. In addition, to adjust the degree of polymerization,
Polymerization inhibitors such as mercaptans, aromatic nitro compounds, thioglycolic acid, and diisopropyl dixanthogen are used. Polymerization may be block polymerization or random polymerization. Effects of the invention By using the antifoam composition of the present invention,
In the manufacturing process of synthetic resins, paints, inks, and adhesives, it is possible to greatly suppress the foaming phenomenon, reduce the introduction of air bubbles, and greatly reduce problems caused by bubbles. In addition, the antifoam composition of the present invention has an excellent antifoaming effect compared to silicone antifoaming agents, has no cissing phenomenon, which is a disadvantage of silicone antifoaming agents, and has no adverse effect on the coating film, and is extremely effective. to provide superior quality products. EXAMPLES The invention will now be further illustrated by examples. still,
In the examples, parts indicate parts by weight. Production example 1 In a four-necked flask, add n-butyl methacrylate.
A polymerization reaction was carried out at 70 to 80°C for 5 hours under a nitrogen gas stream using 200 parts of toluene as a solvent and 0.1 part of 2,2'-azobisisobutyronitrile as a catalyst. A viscous liquid was obtained.
The molecular weight of this polymer was approximately 32,000 as measured by GPC (product of the present invention). Production Example 2 In a four-necked flask, take 80 parts of 2-ethylhexyl methacrylate, 20 parts of n-butyl acrylate, 200 parts of toluene as a solvent, and 0.2 part of 2,2'-azobisisobutyronitrile as a catalyst, and add nitrogen When the polymerization reaction was carried out at 70 to 80℃ for 4 hours under a gas stream,
A pale yellow viscous liquid with a molecular weight of about 21,500 was obtained (product of the present invention). Production example 3 Lauryl methacrylate 90 in a four-necked flask
10 parts of methyl methacrylate, 100 parts of xylene as a solvent, benzoyl peroxide as a catalyst
0.1 part, lauryl mercaptan as a polymerization inhibitor
0.02 part was taken and a polymerization reaction was carried out at 80 to 90°C for 4 hours under a nitrogen gas stream, and after cooling, 100 parts of mineral oil was added to dilute it. A pale yellow viscous liquid with a molecular weight of about 85,000 was obtained (product of the present invention). Production example 4 75 parts of butyl methacrylate in a four-necked flask,
25 parts of stearyl methacrylate, 150 parts of xylene as solvent, benzoyl peroxide as catalyst
0.2 part was taken and polymerized at 80 to 90°C for 5 hours under a nitrogen gas flow, and after cooling, 50 parts of xylene was added to dilute. It was a pale yellow viscous liquid with a molecular weight of approximately 115,000 (product of the present invention). Example 1 Using the present invention product and comparative product as antifoaming agents,
An acrylic resin paint was created using the following formulation.
Then, 20 g of this paint and 10 g of thinner were placed in a stoppered test tube (diameter 25 mm x length 200 mm), and after vigorous shaking up and down for 30 seconds, the time for bubbles to disappear on the liquid surface and inside the liquid was measured. The results are shown in Table 1, and the product of the present invention has excellent anti-foaming and foam-inhibiting properties. Paint formulation Thermoplastic acrylic resin (60%) 80 parts Toluene 10 parts Xylene 6 parts Butanol 3 parts Butyl cellosolve 1 part Antifoaming agent 0.1 part
【表】
実施例 ２
本発明品および比較品を用いて、下記配合に
て、アルキツド樹脂塗料を作成し、この塗料をロ
ーラーバケ（巾75mm）を用いて鉄板上に塗布し、
状態を観察した。結果を表２に示すが、本発明品
は消泡性、塗膜状態とも良好であつた。塗料配合
大豆油変性アルキツド樹脂（油長65％） 48部
酸化チタン（ルチル型） 30部
亜鉛華 ３部
大豆レシチン 0.3部
ステアリン酸アルミニウム 0.1部
ミネラルスピリツト 17部
ジペンテン １部
６％ナフテン酸コバルト 0.4部
24％ナフテン酸鉛 0.1部
５％ナフテン酸カルシウム 0.1部消泡剤 0.1部
（ボールミルにて24時間ミリングし塗料を作成す
る）[Table] Example 2 An alkyd resin paint was prepared using the inventive product and the comparative product with the following formulation, and this paint was applied onto an iron plate using a roller bucket (width 75 mm).
I observed the condition. The results are shown in Table 2, and the product of the present invention had good antifoaming properties and good coating film condition. Paint blended soybean oil modified alkyd resin (oil length 65%) 48 parts titanium oxide (rutile type) 30 parts zinc white 3 parts soybean lecithin 0.3 parts aluminum stearate 0.1 part mineral spirits 17 parts dipentene 1 part 6% cobalt naphthenate 0.4 Part 24% Lead naphthenate 0.1 part 5% Calcium naphthenate 0.1 part Antifoaming agent 0.1 part (Create paint by milling for 24 hours in a ball mill)
Claims (1)
数１〜22の直鎖又は分枝鎖状のアルキル基を表わ
し、ｍ及びｎは、それぞれ独立に、０又は１以上
であつて、合計で30〜1200の整数を表わす〕で示
されるホモポリマー又はコポリマーの１種又は２
種以上の混合物を適当な溶剤に溶解させてなる非
水系抑泡型消泡剤組成物。[Claims] 1. General formula [In the above formula, R 1 and R 2 each independently represent a straight or branched alkyl group having 1 to 22 carbon atoms, and m and n each independently represent 0 or 1 or more; , representing an integer from 30 to 1200 in total] or two homopolymers or copolymers represented by
A non-aqueous anti-foaming antifoam composition prepared by dissolving a mixture of at least one species in a suitable solvent.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59178213A JPS6157211A (en) | 1984-08-29 | 1984-08-29 | Non-aqueous foam suppressing type defoaming composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59178213A JPS6157211A (en) | 1984-08-29 | 1984-08-29 | Non-aqueous foam suppressing type defoaming composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6157211A JPS6157211A (en) | 1986-03-24 |
| JPS6362244B2 true JPS6362244B2 (en) | 1988-12-01 |
Family
ID=16044557
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59178213A Granted JPS6157211A (en) | 1984-08-29 | 1984-08-29 | Non-aqueous foam suppressing type defoaming composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6157211A (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE58903406D1 (en) * | 1989-01-09 | 1993-03-11 | Ciba Geigy Ag | ALKALINE-RESISTANT SILICONE-OIL-FREE FOAMING AGENT. |
| US5100582A (en) * | 1989-12-28 | 1992-03-31 | Nalco Chemical Company | Water soluble polymer as water-in-oil demulsifier |
| JP2002301306A (en) * | 2001-04-05 | 2002-10-15 | San Nopco Ltd | Defoaming agent |
| JP5771795B2 (en) * | 2012-10-19 | 2015-09-02 | サンノプコ株式会社 | Antifoam |
| JP6752060B2 (en) * | 2016-06-01 | 2020-09-09 | 花王株式会社 | Polymer dispersant for inorganic pigments |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS54117204A (en) * | 1978-03-02 | 1979-09-12 | Nippon Synthetic Chem Ind | Antiifoaming printing ink |
-
1984
- 1984-08-29 JP JP59178213A patent/JPS6157211A/en active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS54117204A (en) * | 1978-03-02 | 1979-09-12 | Nippon Synthetic Chem Ind | Antiifoaming printing ink |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6157211A (en) | 1986-03-24 |
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