JP2021046476A - Antifreeze agent, voc free aqueous emulsion coating containing the same - Google Patents
Antifreeze agent, voc free aqueous emulsion coating containing the same Download PDFInfo
- Publication number
- JP2021046476A JP2021046476A JP2019168897A JP2019168897A JP2021046476A JP 2021046476 A JP2021046476 A JP 2021046476A JP 2019168897 A JP2019168897 A JP 2019168897A JP 2019168897 A JP2019168897 A JP 2019168897A JP 2021046476 A JP2021046476 A JP 2021046476A
- Authority
- JP
- Japan
- Prior art keywords
- antifreeze agent
- antifreeze
- carbon atoms
- water
- polyoxyalkylene compound
- 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
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Landscapes
- Materials Applied To Surfaces To Minimize Adherence Of Mist Or Water (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Paints Or Removers (AREA)
Abstract
Description
本発明は凍結防止剤、これを含有するＶＯＣフリー水性エマルション塗料に関する。 The present invention relates to an antifreeze agent and a VOC-free water-based emulsion coating material containing the agent.
塗料用凍結防止剤として、以下のものが知られている（特許文献１の０１０７段落等）。
「（１）単糖類、多糖類およびこれらの誘導体。例えば、グルコース、スクロース、マルトース、トレハロース、ソルビトール、マンニトール、マンノース、フルクトース、リボース、キシロース、アラビノース、ガラクトース、アルドン酸、セロビオース、ラクトース、マルトトリオース、及びこれらの糖類の還元糖や酸化物、脱水糖誘導体、アミノ糖、チオ糖などが挙げられる。中でも好ましくは グルコース、アラビノース、ガラクトースである。
（２）グリセリンまたはアルキレングリコール類。例えば、グリセリン、エチレングリコール、ジエチレングリコール、トリエチレングリコール、プロピレングリコール、ジプロピレングリコール、１，２−ヘキサンジオール、１，６−ヘキサンジオール、１，５−ペンタンジオール、１，４−ブタンジオールなどが挙げられる。中でも好ましくはグリセリン、エチレングリコールである。
（３）アミノ酸およびその誘導体。例えば、ヒスチジン、アルギニン、リシン、グリシン、Ｌ−アラニン、ＤＬ−アラニン、Ｌ−イソロイシン、Ｌ−バリン、Ｌ−ロイシン、Ｌ−セリン、Ｌ−トレオニン、Ｌ−システイン、Ｌ−シスチン、Ｌ−フェニルアラニン、Ｌ−プロリン、Ｌ−チロシン、Ｌ−ホモセリン、Ｌ−メチオニン、Ｌ−メチオニン、ＤＬ−メチオニン、ε−アミノカプロン酸、γ−アミノ酪酸、ＤＬ−トレオニン、アスパラギン酸、グルタミン酸などが挙げられる。中でも好ましくはグリシン、Ｌ−アラニン、ＤＬ−アラニン、アルギニンである。
（４）尿素およびその誘導体。例えば、尿素、チオ尿素、エチレン尿素、Ｎ−メチル尿素、Ｎ，Ｎ−ジメチル尿素、Ｎ−エチル尿素、Ｎ−ヒドロキシエチル尿素などが挙げられる。中でも好ましくは尿素、チオ尿素、エチレン尿素である。
（５）環状アミド基を有する化合物。例えば、２−ピロリドン、Ｎ−メチル−２−ピロリドン、ε−カプロラクタム、γ−カプロラクタム、Ｎ−ヒドロキシエチル−２−ピロリドン、Ｎ−エチル−２−ピロリドンなどが挙げられる。中でも好ましくは２−ピロリドン、Ｎ−メチル−２−ピロリドンである。」
The following are known as antifreeze agents for paints (paragraph 0107 of Patent Document 1 and the like).
"(1) Monosaccharides, polysaccharides and derivatives thereof. For example, glucose, sucrose, maltose, trehalose, sorbitol, mannitol, mannose, fructose, ribose, xylose, arabinose, galactose, aldonic acid, cellobiose, lactose, maltotriose. , And reduced sugars and oxides of these sugars, dehydrated sugar derivatives, amino sugars, thiosaccharides and the like. Among them, glucose, arabinose and galactose are preferable.
(2) Glycerin or alkylene glycols. For example, glycerin, ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, 1,2-hexanediol, 1,6-hexanediol, 1,5-pentanediol, 1,4-butanediol and the like can be mentioned. Be done. Of these, glycerin and ethylene glycol are preferable.
(3) Amino acids and their derivatives. For example, histidine, arginine, lysine, glycine, L-alanine, DL-alanine, L-isoleucine, L-valine, L-leucine, L-serine, L-threonine, L-cysteine, L-cystine, L-phenylalanine, Examples thereof include L-proline, L-tyrosine, L-homoseline, L-methionine, L-methionine, DL-methionine, ε-aminocaproic acid, γ-aminobutyric acid, DL-threonine, aspartic acid, and glutamic acid. Of these, glycine, L-alanine, DL-alanine, and arginine are preferable.
(4) Urea and its derivatives. For example, urea, thiourea, ethylene urea, N-methylurea, N, N-dimethylurea, N-ethylurea, N-hydroxyethylurea and the like can be mentioned. Of these, urea, thiourea, and ethylene urea are preferable.
(5) A compound having a cyclic amide group. For example, 2-pyrrolidone, N-methyl-2-pyrrolidone, ε-caprolactam, γ-caprolactam, N-hydroxyethyl-2-pyrrolidone, N-ethyl-2-pyrrolidone and the like can be mentioned. Of these, 2-pyrrolidone and N-methyl-2-pyrrolidone are preferable. "
従来の塗料用凍結防止剤では、凍結防止性が不十分であったり、ＶＯＣに該当したり、耐水性が不十分であるという問題がある。
本発明の目的は、優れた凍結防止性及び優れた耐水性を発揮するＶＯＣフリーの凍結防止剤を提供することである。
なお、ＶＯＣとは、沸点が２６０℃までの有機溶剤を揮発性有機化合物（Volatile Organic Compounds；ＶＯＣ）として定義され、シックハウス症候群の原因の一つとされている｛世界保健機関（ＷＨＯ）｝。
Conventional antifreeze agents for paints have problems such as insufficient antifreezing properties, VOCs, and insufficient water resistance.
An object of the present invention is to provide a VOC-free antifreeze agent that exhibits excellent antifreeze properties and excellent water resistance.
VOC is defined as volatile organic compounds (VOCs) of organic solvents having a boiling point of up to 260 ° C., and is regarded as one of the causes of sick building syndrome {World Health Organization (WHO)}.
本発明の凍結防止剤の特徴は、揮発性有機化合物（Volatile Organic Compounds）を含まない（ＶＯＣフリー）の水性エマルション塗料の凍結を防止するための薬剤であって、
式（１）で表されるポリオキシアルキレン化合物（Ｘ）を含有してなる点を要旨とする。
The feature of the antifreeze agent of the present invention is an agent for preventing freezing of a (VOC-free) water-based emulsion paint that does not contain volatile organic compounds (Volatile Organic Compounds).
The gist is that it contains the polyoxyalkylene compound (X) represented by the formula (1).
Ｒ−Ｎ｛−（ＡＯ）ｎ―Ｈ｝２ （１） RN {-(AO) n-H} 2 (1)
Ｒは炭素数８〜２２のアルキル基又はアルケニル基、Ｎは窒素原子、Ｈは水素原子、ＡＯは炭素数２〜４のオキシアルキレン基、ｎは２〜２０の整数を表す。 R represents an alkyl group or an alkenyl group having 8 to 22 carbon atoms, N represents a nitrogen atom, H represents a hydrogen atom, AO represents an oxyalkylene group having 2 to 4 carbon atoms, and n represents an integer of 2 to 20 carbon atoms.
本発明の水性エマルション塗料の特徴は、水、エマルション樹脂及び上記の凍結防止剤を含んでなる水性エマルション塗料であって、
この凍結防止剤の含有量が水、エマルション樹脂及び凍結防止剤の重量に基づいて０．５〜５重量％である点を要旨とする。
A feature of the water-based emulsion paint of the present invention is a water-based emulsion paint containing water, an emulsion resin and the above-mentioned antifreeze agent.
The gist is that the content of the antifreeze is 0.5 to 5% by weight based on the weight of water, the emulsion resin and the antifreeze.
本発明の凍結防止剤は、優れた凍結防止性及び優れた耐水性を発揮すると共に、揮発性有機化合物（Volatile Organic Compounds）を含まない（ＶＯＣフリー）の水性エマルション塗料を調製することができる。 The antifreeze agent of the present invention exhibits excellent antifreeze properties and excellent water resistance, and can prepare a (VOC-free) water-based emulsion coating material containing no volatile organic compounds (Volatile Organic Compounds).
本発明の水性エマルション塗料は、上記の凍結防止剤を含むので、優れた凍結防止性及び優れた耐水性を発揮すると共にＶＯＣフリーとすることができる。 Since the water-based emulsion coating material of the present invention contains the above-mentioned antifreezing agent, it can exhibit excellent antifreezing properties and excellent water resistance and can be VOC-free.
＜ポリオキシアルキレン化合物（Ｘ）＞
炭素数８〜２２（１０〜２０が好ましく、さらに好ましくは１２〜１８）のアルキル基又はアルケニル基（Ｒ）としては、ｎ−オクチル、２−エチルヘキシル、ｎ−ノニル、ｎ−デシル、イソデシル、ｎ−ウンデシル、ｎ−ドデシル、ｎ−トリデシル、イソトリデシル、ｎ−テトラデシル、ｎ−ペンタデシル、ｎ−ヘキサデシル、ｎ−ヘプタデシル、ｎ−オクタデシル、イソオクタデシル、ｎ−デセニル、２−ドデセニル、イソトリデセニル及びｎ−オクタデセニル等が挙げられる。
<Polyoxyalkylene compound (X)>
Examples of the alkyl group or alkenyl group (R) having 8 to 22 carbon atoms (preferably 10 to 20 and more preferably 12 to 18) include n-octyl, 2-ethylhexyl, n-nonyl, n-decyl, isodecyl and n. -Undecylic, n-dodecyl, n-tridecylic, isotridecylic, n-tetradecyl, n-pentadecylic, n-hexadecyl, n-heptadecyl, n-octadecyl, isooctadecyl, n-decenyl, 2-dodecenyl, isotridecenyl and n-octadeceln Can be mentioned.
オキシアルキレン基（ＡＯ）として、複数種類のオキシアルキレン基を含む場合、結合様式はブロック状、ランダム状及びこれらの混合のいずれでもよい。 When a plurality of types of oxyalkylene groups are contained as the oxyalkylene group (AO), the bonding mode may be block-shaped, random-shaped, or a mixture thereof.
一般式（１）で表されるポリオキシアルキレン化合物（Ｘ）としては、炭素数８〜２２のアルキルアミン（ａ１）又はアルケニルアミン（ａ２）とエチレンオキシド、プロピレンオキシド及び／又はブチレンオキシド（ａ３）との化学反応により製造される構造を有するポリオキシアルキレン化合物が含まれる｛（ａ１）又は（ａ２）１モルに対して（ａ３）４〜４０モルの量が好ましい。｝。 Examples of the polyoxyalkylene compound (X) represented by the general formula (1) include alkylamines (a1) or alkenylamines (a2) having 8 to 22 carbon atoms and ethylene oxide, propylene oxide and / or butylene oxide (a3). The amount of (a3) 4 to 40 mol is preferable with respect to 1 mol of {(a1) or (a2) containing the polyoxyalkylene compound having a structure produced by the chemical reaction of. }.
炭素数８〜２２のアルキルアミン（ａ１）又はアルケニルアミン（ａ２）としては、ｎ−オクチルアミン、２−エチルヘキシルアミン、ｎ−ノニルアミン、ｎ−デシルアミン、イソデシルアミン、ｎ−ウンデシルアミン、ｎ−ドデシルアミン、ｎ−トリデシルアミン、イソトリデシルアミン、ｎ−テトラデシルアミン、ｎ−ペンタデシルアミン、ｎ−ヘキサデシルアミン、ｎ−ヘプタデシルアミン、ｎ−オクタデシルアミン、イソオクタデシルアミン、ｎ−デセニルアミン、２−ドデセニルアミン、イソトリデセニルアミン及びｎ−オクタデセニルアミン等が挙げられる。 Examples of the alkylamine (a1) or alkenylamine (a2) having 8 to 22 carbon atoms include n-octylamine, 2-ethylhexylamine, n-nonylamine, n-decylamine, isodecylamine, n-undecylamine, and n-. Dodecylamine, n-tridecylamine, isotridecylamine, n-tetradecylamine, n-pentadecylamine, n-hexadecylamine, n-heptadecylamine, n-octadecylamine, isooctadecylamine, n-decenylamine , 2-Dodecenylamine, Isotridecenylamine, n-octadecenylamine and the like.
＜ポリオキシアルキレン化合物Ｙ＞
本発明の凍結防止剤には、式（２）で表されるポリオキシアルキレン化合物（Ｙ）を含有することが好ましい。
<Polyoxyalkylene compound Y>
The antifreeze agent of the present invention preferably contains the polyoxyalkylene compound (Y) represented by the formula (2).
Ｑ｛（−ＡＯ）ｍ−Ｈ｝ｔ （２） Q {(-AO) m- H} t (2)
ただし、Ｑは非還元性の二又は三糖類のｔ個の１級水酸基から水素原子を除いた残基、ＡＯは炭素数２〜４のオキシアルキレン基、ｍは５〜３０の整数、ｔは２〜４の整数、Ｈは水素原子を表し、ＡＯの総数は残基（Ｑ）１個当たり２０〜８０個であり、（−ＡＯ）ｍが一分子中に複数個含まれる場合、それぞれは同じでも異なっていてもよい。 However, Q is a residue obtained by removing a hydrogen atom from t primary hydroxyl groups of a non-reducing di or trisaccharide, AO is an oxyalkylene group having 2 to 4 carbon atoms, m is an integer of 5 to 30, and t is an integer of 5 to 30. An integer of 2 to 4, H represents a hydrogen atom, the total number of AOs is 20 to 80 per residue (Q), and when a plurality of (-AO) m are contained in one molecule, each of them It may be the same or different.
非還元性の二又は三糖類のｔ個の１級水酸基から水素原子を除いた残基（Ｑ）を構成することができる非還元性の二又は三糖類としては、蔗糖（サッカロース）、トレハロース、イソトレハロース、イソサッカロース、ゲンチアノース、ラフィノース、メレチトース及びプランテオース等が挙げられる。これらのうち、凍結防止性及び耐水性の観点から、蔗糖、トレハロース、ゲンチアノース、ラフィノース及びプランテオースが好ましく、さらに好ましくは蔗糖、トレハロース及びラフィノースであり、供給性及びコスト等の観点から特に好ましくは蔗糖である。 Non-reducing di- or trisaccharides that can constitute the residue (Q) obtained by removing the hydrogen atom from the t primary hydroxyl groups of the non-reducing di- or trisaccharide include sucrose, trehalose, and the like. Examples thereof include isototrehalose, isosaccalose, gentianose, raffinose, meletitos and planteose. Of these, sucrose, trehalose, gentianose, raffinose and planteose are preferable from the viewpoint of antifreezing property and water resistance, and sucrose, trehalose and raffinose are more preferable, and sucrose is particularly preferable from the viewpoint of supply and cost. Is.
炭素数２〜４のオキシアルキレン基（ＡＯ）としては、オキシエチレン、オキシプロピレン及びオキシブチレン等が挙げられる。これらのうち、凍結防止性及び耐水性の観点から、残基（Ｑ）１個当たりのオキシアルキレン基（ＡＯ）の総数が２５〜５９個の場合、オキシプロピレン単独が好ましく、この総数が１５〜２４個の場合、オキシブチレンとオキシプロピレンの混合が好ましく、この総数が６０〜８０個の場合、オキシエチレンとオキシプロピレンの混合が好ましい。 Examples of the oxyalkylene group (AO) having 2 to 4 carbon atoms include oxyethylene, oxypropylene and oxybutylene. Of these, from the viewpoint of antifreeze and water resistance, when the total number of oxyalkylene groups (AOs) per residue (Q) is 25 to 59, oxypropylene alone is preferable, and the total number is 15 to 15. In the case of 24 pieces, a mixture of oxybutylene and oxypropylene is preferable, and in the case of a total of 60 to 80 pieces, a mixture of oxyethylene and oxypropylene is preferable.
オキシプロピレン及び／又はオキシブチレンとオキシエチレンとの混合を含む場合、オキシエチレンの含有割合（モル％）は、オキシアルキレン基の全モル数に基づいて、２〜１０が好ましく、さらに好ましくは２〜８、特に好ましくは４〜６である。また、この場合、反応残基（Ｑ）から離れた端部にオキシプロピレン及び／又はオキシブチレンが位置することが好ましい。すなわち、この場合、反応残基（Ｑ）にオキシエチレン基が直接的に結合していることが好ましい。また、複数種類のオキシアルキレン基（ＯＡ又はＡＯ）を含む場合、結合様式はブロック状、ランダム状及びこれらの混合のいずれでもよいが、少なくともブロック状を含むことが好ましい。 When oxypropylene and / or a mixture of oxybutylene and oxyethylene is included, the content ratio (mol%) of oxyethylene is preferably 2 to 10 based on the total number of moles of oxyalkylene groups, and more preferably 2 to 10. 8, particularly preferably 4 to 6. Further, in this case, it is preferable that oxypropylene and / or oxybutylene is located at the end away from the reaction residue (Q). That is, in this case, it is preferable that the oxyethylene group is directly bonded to the reaction residue (Q). When a plurality of types of oxyalkylene groups (OA or AO) are contained, the bonding mode may be block-like, random-like, or a mixture thereof, but at least block-like is preferable.
ｍは、５〜３０の整数が好ましく、さらに好ましくは７〜２８の整数、特に好ましくは１０〜２５の整数である。この範囲であると、凍結防止性及び耐水性がさらに良好となる。 m is preferably an integer of 5 to 30, more preferably an integer of 7 to 28, and particularly preferably an integer of 10 to 25. Within this range, antifreezing properties and water resistance are further improved.
ｔは、２〜４の整数が好ましく、さらに好ましくは３である。この範囲であると、凍結防止性及び耐水性がさらに良好となる。 t is preferably an integer of 2 to 4, and more preferably 3. Within this range, antifreezing properties and water resistance are further improved.
ポリオキシアルキレン化合物（Ｙ）を含有する場合、ポリオキシアルキレン化合物（Ｘ）と、ポリオキシアルキレン化合物（Ｙ）の含有重量比｛（Ｘ）：（Ｙ）｝は、凍結防止性及び耐水性の観点から、５０〜９５：５０〜５が好ましく、さらに好ましくは５５〜９０：４５〜１０である。 When the polyoxyalkylene compound (Y) is contained, the weight ratio of the polyoxyalkylene compound (X) to the polyoxyalkylene compound (Y) {(X): (Y)} is antifreezing and water resistant. From the viewpoint, it is preferably 50 to 95:50 to 5, and more preferably 55 to 90:45 to 10.
本発明の凍結防止剤には、必要により公知の添加剤（消泡剤、粘度調整剤、湿潤剤等）等を含有できる。 The antifreeze agent of the present invention may contain known additives (antifoaming agent, viscosity modifier, wetting agent, etc.), if necessary.
消泡剤としてはＳＮデフォーマー１８０及び同１８４（サンノプコ株式会社製）等が挙げられ、粘度調整剤としてはＳＮシックナー６０１及び同６１２（サンノプコ株式会社製）等が挙げられ、湿潤剤としてはＳＮウエット１２５及び同１２６（サンノプコ株式会社製）等が挙げられる。なお、公知の添加剤を含有する場合、これらの含有量は、凍結防止剤の重量に基づいて、０．０１〜１０重量％程度が好ましい。 Examples of the defoaming agent include SN Deformer 180 and 184 (manufactured by San Nopco Co., Ltd.), examples of the viscosity modifier include SN Sixner 601 and 612 (manufactured by San Nopco Co., Ltd.), and examples of the wetting agent are SN Wet. 125 and 126 (manufactured by San Nopco Co., Ltd.) and the like can be mentioned. When known additives are contained, the content thereof is preferably about 0.01 to 10% by weight based on the weight of the antifreeze agent.
本発明の凍結防止剤の製造方法は、特に制限は無く公知の方法が適用でき、公知のアルキレンオキシド付加反応等により、ポリオキシアルキレン化合物（Ｘ）及びはポリオキシアルキレン化合物（Ｙ）を調製でき、ポリオキシアルキレン化合物（Ｙ）を含有する場合、ポリオキシアルキレン化合物（Ｘ）及びはポリオキシアルキレン化合物（Ｙ）を均一混合することにより得ることができる。均一混合温度に制限はないが、混合効率の観点から、１０〜７０℃程度が好ましい。 The method for producing the antifreeze agent of the present invention is not particularly limited, and a known method can be applied, and a polyoxyalkylene compound (X) and a polyoxyalkylene compound (Y) can be prepared by a known alkylene oxide addition reaction or the like. When the polyoxyalkylene compound (Y) is contained, the polyoxyalkylene compound (X) and the polyoxyalkylene compound (Y) can be obtained by uniformly mixing the polyoxyalkylene compound (Y). The uniform mixing temperature is not limited, but is preferably about 10 to 70 ° C. from the viewpoint of mixing efficiency.
本発明の凍結防止剤は、水を含む塗料に広く適用でき、特に水性エマルション塗料に好適である。 The antifreeze agent of the present invention can be widely applied to paints containing water, and is particularly suitable for water-based emulsion paints.
＜水性エマルション塗料＞
本発明の水性エマルション塗料としては、水、エマルション樹脂及び上記の凍結防止剤を含んでなり、必要により、顔料、分散剤、湿潤剤、粘弾性調整剤、消泡剤、防腐剤及び／又は造膜助剤を含むことができる。
<Aqueous emulsion paint>
The water-based emulsion coating material of the present invention contains water, an emulsion resin and the above-mentioned antifreeze agent, and if necessary, a pigment, a dispersant, a wetting agent, a viscoelasticity adjusting agent, a defoaming agent, a preservative and / or a product. Membrane aids can be included.
凍結防止剤の使用量（重量％）は、水、エマルション樹脂及び凍結防止剤の重量に基づいて０．５〜５が好ましく、さらに好ましくは１〜４である。この範囲であると、さらに凍結防止性及び耐水性を発揮がさらに良好となる。 The amount (% by weight) of the antifreeze agent used is preferably 0.5 to 5, more preferably 1 to 4, based on the weight of water, the emulsion resin and the antifreeze agent. Within this range, the antifreezing property and the water resistance are further improved.
本発明の水性エマルション塗料は、公知の方法等により得られ、凍結防止剤はいずれの工程で混合できる。 The aqueous emulsion coating material of the present invention can be obtained by a known method or the like, and the antifreeze agent can be mixed in any step.
本発明の水性エマルション塗料は、各種用途に用いることができ、建築塗料又はタンク、橋梁等の構造物用塗料等の塗料、塗工紙用コーティング液、電磁気・光学部材等の電子材料用塗料、セラミックスを使用した構造材料用塗料及び各種成型体へ塗布する機能性スラリー用塗料等のコーティング組成物などに適用できる。 The water-based emulsion paint of the present invention can be used for various purposes, such as building paints or paints for structures such as tanks and bridges, coating liquids for coating paper, paints for electronic materials such as electromagnetic and optical members, and the like. It can be applied to coating compositions such as paints for structural materials using ceramics and paints for functional slurry to be applied to various molded bodies.
＜実施例１〜７＞
式（１）で表されるポリオキシアルキレン化合物（Ｘ）として、ｎ−オクタデシルアミン・エチレンオキシド２０モル付加体（Ｘ１）、イソデシルアミン・エチレンオキシド７モル付加体（Ｘ２）、ｎ−デセニルアミン・エチレンオキシド４モル付加体（Ｘ３）及び２−ドデセニルアミン・エチレンオキシド４０モル付加体（Ｘ４）を用い、式（２）で表されるポリオキシアルキレン化合物（Ｙ）として、蔗糖・エチレンオキシド３モル・プロピレンオキシド７２モルブロック付加体（Ｙ１）、トレハロース・プロピレンオキシド１２モル・ブチレンオキシド８モルランダム付加体（Ｙ２）、蔗糖・エチレンオキシド４モル・プロピレンオキシド６３モルブロック付加体（Ｙ３）及び蔗糖・プロピレンオキシド５９モル付加体（Ｙ４）を用いて、それぞれ、表１に記載した量（重量部）を均一混合して、実施例１〜７の凍結防止剤（１）〜（７）を調製した。
<Examples 1 to 7>
As the polyoxyalkylene compound (X) represented by the formula (1), n-octadecylamine / ethylene oxide 20 mol adduct (X1), isodecylamine / ethylene oxide 7 mol adduct (X2), n-decenylamine / ethylene oxide 4 Using a molar adduct (X3) and a 40 mol adduct of 2-dodecenylamine / ethylene oxide (X4), as the polyoxyalkylene compound (Y) represented by the formula (2), sugar / ethylene oxide 3 mol / propylene oxide 72 mol block. Addendum (Y1), trehalose / propylene oxide 12 mol / butylene oxide 8 mol random adduct (Y2), sucrose / ethylene oxide 4 mol / propylene oxide 63 mol block adduct (Y3) and sucrose / propylene oxide 59 mol adduct (Y2) Using Y4), the amounts (parts by weight) shown in Table 1 were uniformly mixed to prepare the antifreeze agents (1) to (7) of Examples 1 to 7.
＜比較例１＞
特許文献１に記載されたエチレングリコールを比較用の凍結防止剤（Ｈ１）とした。
<Comparative example 1>
The ethylene glycol described in Patent Document 1 was used as an antifreeze agent (H1) for comparison.
＜比較例２＞
特許文献１に記載されたグルコースを比較用の凍結防止剤（Ｈ２）とした。
<Comparative example 2>
The glucose described in Patent Document 1 was used as an antifreeze agent (H2) for comparison.
＜比較例３＞
特許文献１に記載された尿素を比較用の凍結防止剤（Ｈ３）とした。
<Comparative example 3>
The urea described in Patent Document 1 was used as an antifreeze agent (H3) for comparison.
＜比較例４＞
特許文献１に記載されたＮ−メチル−２−ピロリドンを比較用の凍結防止剤（Ｈ４）とした。
<Comparative example 4>
N-methyl-2-pyrrolidone described in Patent Document 1 was used as an antifreeze agent (H4) for comparison.
＜評価１＞
１．評価用エマルション塗料の調製
表２に記載した原料組成にて、円盤型羽根を装着した卓上サンドミル（カンペ家庭塗料株式会社、カンペサンドミル）でグラインディングし、ついでアンカー型羽根を装着した撹拌機（東京理化器械株式会社、ＭＡＺＥＬＬＡ ＺＺ−１１００）でレットダウンして、エマルションベース塗料を調製した。このエマルションベース塗料９８重量部並びに実施例で得た凍結防止剤（１）〜（７）のいずれか又は比較用の凍結防止剤（Ｈ１）〜（Ｈ４）のいずれか２重量をコーレス型羽根を装着したエクセルオートホモジナイザー（日本精器株式会社、モデルＥＤ）にて２５℃、３０００ｒｐｍ、５分間攪拌混合して評価用エマルション塗料を得た。
<Evaluation 1>
1. 1. Preparation of Emulsion Paint for Evaluation With the raw material composition shown in Table 2, grinding was performed with a desktop sand mill equipped with disk-shaped blades (Kampe Home Paint Co., Ltd., Kampe Sand Mill), and then a stirrer equipped with anchor-shaped blades (Tokyo). Rika Kikai Co., Ltd., MAZELLA ZZ-1100) was used to let down to prepare an emulsion-based paint. 98 parts by weight of this emulsion-based paint and any two weights of the antifreeze agents (1) to (7) obtained in the examples or any two of the antifreeze agents (H1) to (H4) for comparison were applied to the cores type blade. An emulsion paint for evaluation was obtained by stirring and mixing at 25 ° C., 3000 rpm for 5 minutes with the attached Excel autohomogenizer (Nippon Seiki Co., Ltd., model ED).
※１ 分散剤、サンノプコ株式会社、「ノプコール」は同社の登録商標である。
※２ 増粘剤、ダイセルファインケム株式会社
※３ 湿潤剤、サンノプコ株式会社
※４ 湿潤剤、サンノプコ株式会社
※５ 硫酸バリウム、堺化学工業株式会社、「バリエース」は同社の登録商標である。
※６ 二酸化チタン、石原産業株式会社、「タイペーク」は同社の登録商標である。
※７ アクリルフッ素エマルション、株式会社イーテック、「ＳＩＦＣＬＥＡＲ」はＪＳＲ株式会社の登録商標である。
※８ 造膜調整剤、ＪＮＣ株式会社
* 1 Dispersant, San Nopco Co., Ltd., and "Nopcol" are registered trademarks of the same company.
* 2 Thickener, Daicel FineChem Co., Ltd. * 3 Wetting agent, San Nopco Co., Ltd. * 4 Wetting agent, San Nopco Co., Ltd. * 5 Barium sulfate, Sakai Chemical Industry Co., Ltd., and "Variace" are registered trademarks of the same company.
* 6 Titanium dioxide, Ishihara Sangyo Co., Ltd., and "Typake" are registered trademarks of the same company.
* 7 Acrylic fluorine emulsion, E-Tech Co., Ltd., and "SIFCLEAR" are registered trademarks of JSR Corporation.
* 8 Film-forming conditioner, JNC Corporation
２．凍結防止性
評価用エマルション塗料を１４０ｃｃ容量のガラス瓶に１００重量部入れ、密閉し、−５℃で３６時間放置後、ガラス瓶を真横に倒して５分後の状態を以下の基準で評価し、表５に示した。
○：エマルション塗料は流動し、塗料液面は水平となった
×：エマルション塗料は流動せず、塗料面は垂直のままであった
2. Put 100 parts by weight of the emulsion paint for antifreeze evaluation in a glass bottle with a capacity of 140 cc, seal it, leave it at -5 ° C for 36 hours, lay the glass bottle sideways, and evaluate the state after 5 minutes according to the following criteria. Shown in 5.
◯: The emulsion paint flowed and the paint liquid level became horizontal. ×: The emulsion paint did not flow and the paint surface remained vertical.
２．耐水性
隙間１５０μｍのアプリケーターを用いて各評価用エマルション塗料をガラス板（アセトンで脱脂したもの）に塗布し、屋内（２５℃）で３日乾燥後の塗装片を、２５℃のイオン交換水に３日間浸漬した後、水から引き上げて中央部分の１０ｃｍ×１０ｃｍ面積内のブリスター（水膨れ）痕の有無を目視判定し、表５に示した。
○：ブリスターなし
×：ブリスターあり
2. Apply each evaluation emulsion paint to a glass plate (defatted with acetone) using an applicator with a water resistance gap of 150 μm, and dry the coated piece indoors (25 ° C) for 3 days into ion-exchanged water at 25 ° C. After soaking for 3 days, it was pulled up from water and visually judged for the presence or absence of blister (water swelling) marks within a 10 cm × 10 cm area in the central portion, and is shown in Table 5.
○: No blister ×: With blister
＜評価２＞
「表２に記載した原料組成」を「表３に記載した原料組成」に変更したこと以外、評価１と同様にして、エマルションベース塗料を調製し、評価用エマルション塗料を得た。
そして、評価１と同様にして、凍結防止性及び耐水性を評価して、表５に示した。
<Evaluation 2>
An emulsion-based paint was prepared in the same manner as in Evaluation 1 except that the "raw material composition shown in Table 2" was changed to the "raw material composition shown in Table 3" to obtain an emulsion paint for evaluation.
Then, the antifreeze property and the water resistance were evaluated in the same manner as in Evaluation 1, and are shown in Table 5.
※９ 分散剤、サンノプコ株式会社、「ノプコスパース」は同社の登録商標である。
※１０ 炭酸カルシウム、竹原化学工業株式会社
※１１ アクリルエマルション、ＢＡＳＦジャパン株式会社、「ＡＣＲＯＮＡＬ」はビーエーエスエフ ソシエタス・ヨーロピアの登録商標である。
* 9 Dispersants, San Nopco Co., Ltd., and "Nopco Spars" are registered trademarks of the same company.
* 10 Calcium carbonate, Takehara Chemical Industry Co., Ltd. * 11 Acrylic emulsion, BASF Japan Co., Ltd., "ACRONAL" are registered trademarks of BASF Society Europe.
＜評価３＞
「表２に記載した原料組成」を「表４に記載した原料組成」に変更したこと以外、評価１と同様にして、エマルションベース塗料を調製し、評価用エマルション塗料を得た。
そして、評価１と同様にして、凍結防止性及び耐水性を評価して、表５に示した。
<Evaluation 3>
An emulsion-based paint was prepared in the same manner as in Evaluation 1 except that the "raw material composition shown in Table 2" was changed to the "raw material composition shown in Table 4" to obtain an emulsion paint for evaluation.
Then, the antifreeze property and the water resistance were evaluated in the same manner as in Evaluation 1, and are shown in Table 5.
※１２ 分散剤、サンノプコ株式会社、「ノプコール」は同社の登録商標である。
※１３ 増粘剤、サンノプコ株式会社
※１４ 湿潤剤、サンノプコ株式会社
※１５ アクリルエマルション、ＤＩＣ株式会社、「ボンコート」は同社の登録商標である。
※１６ 増粘剤、サンノプコ株式会社
* 12 Dispersants, San Nopco Co., Ltd., and "Nopcol" are registered trademarks of the same company.
* 13 Thickener, San Nopco Co., Ltd. * 14 Wetting agent, San Nopco Co., Ltd. * 15 Acrylic emulsion, DIC Corporation, and "Boncoat" are registered trademarks of the same company.
* 16 Thickener, San Nopco Co., Ltd.
表５において、ＶＯＣの欄に、揮発性有機化合物（Volatile Organic Compounds；ＶＯＣ）に該当するものに×、非該当のものに○を付した。 In Table 5, in the column of VOC, those corresponding to volatile organic compounds (VOC) are marked with x, and those not corresponding are marked with a circle.
Claims (5)
式（１）で表されるポリオキシアルキレン化合物（Ｘ）を含有してなることを特徴とする凍結防止剤。
Ｒ−Ｎ｛−（ＡＯ）ｎ―Ｈ｝２ （１）
Ｒは炭素数８〜２２のアルキル基又はアルケニル基、Ｎは窒素原子、Ｈは水素原子、ＡＯは炭素数２〜４のオキシアルキレン基、ｎは２〜２０の整数を表す。 A drug for preventing freezing of (VOC-free) water-based emulsion paints that do not contain volatile organic compounds (Volatile Organic Compounds).
An antifreeze agent containing the polyoxyalkylene compound (X) represented by the formula (1).
RN {-(AO) n-H} 2 (1)
R represents an alkyl group or an alkenyl group having 8 to 22 carbon atoms, N represents a nitrogen atom, H represents a hydrogen atom, AO represents an oxyalkylene group having 2 to 4 carbon atoms, and n represents an integer of 2 to 20 carbon atoms.
Ｑ｛（−ＡＯ）ｍ−Ｈ｝ｔ （２）
ただし、Ｑは非還元性の二又は三糖類のｔ個の１級水酸基から水素原子を除いた残基、ＡＯは炭素数２〜４のオキシアルキレン基、ｍは５〜３０の整数、ｔは２〜４の整数、Ｈは水素原子を表し、ＡＯの総数は残基（Ｑ）１個当たり２０〜８０個であり、（−ＡＯ）ｍが一分子中に複数個含まれる場合、それぞれは同じでも異なっていてもよい。 The antifreeze agent according to claim 1, further containing the polyoxyalkylene compound (Y) represented by the formula (2).
Q {(-AO) m- H} t (2)
However, Q is a residue obtained by removing a hydrogen atom from t primary hydroxyl groups of a non-reducing di or trisaccharide, AO is an oxyalkylene group having 2 to 4 carbon atoms, m is an integer of 5 to 30, and t is an integer of 5 to 30. An integer of 2 to 4, H represents a hydrogen atom, the total number of AOs is 20 to 80 per residue (Q), and when a plurality of (-AO) m are contained in one molecule, each of them It may be the same or different.
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH06228868A (en) * | 1993-01-30 | 1994-08-16 | Lion Corp | Liquid softener composition |
| JP2008308684A (en) * | 2007-05-15 | 2008-12-25 | Fujifilm Corp | Aqueous paint composition |
| JP2014523923A (en) * | 2011-07-28 | 2014-09-18 | アンガス ケミカル カンパニー | Amino alcohol compounds and their use as zero or low VOC additives for paints and coatings |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH06228868A (en) * | 1993-01-30 | 1994-08-16 | Lion Corp | Liquid softener composition |
| JP2008308684A (en) * | 2007-05-15 | 2008-12-25 | Fujifilm Corp | Aqueous paint composition |
| JP2014523923A (en) * | 2011-07-28 | 2014-09-18 | アンガス ケミカル カンパニー | Amino alcohol compounds and their use as zero or low VOC additives for paints and coatings |
| JP2017014524A (en) * | 2011-07-28 | 2017-01-19 | アンガス ケミカル カンパニー | Amino alcohol compound and use thereof as zero or low voc additive for paint and coating |
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