JP2011021129A - Film-forming auxiliary and coating composition - Google Patents
Film-forming auxiliary and coating composition Download PDFInfo
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- JP2011021129A JP2011021129A JP2009168339A JP2009168339A JP2011021129A JP 2011021129 A JP2011021129 A JP 2011021129A JP 2009168339 A JP2009168339 A JP 2009168339A JP 2009168339 A JP2009168339 A JP 2009168339A JP 2011021129 A JP2011021129 A JP 2011021129A
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- 239000008199 coating composition Substances 0.000 title claims abstract description 22
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- 150000001875 compounds Chemical class 0.000 claims abstract description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
- 239000001257 hydrogen Substances 0.000 claims abstract description 4
- 239000000839 emulsion Substances 0.000 claims description 38
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 239000004814 polyurethane Substances 0.000 claims description 9
- 229920002635 polyurethane Polymers 0.000 claims description 9
- 238000000576 coating method Methods 0.000 claims description 6
- 239000011248 coating agent Substances 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 239000000463 material Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 6
- 238000009835 boiling Methods 0.000 abstract description 3
- 231100000053 low toxicity Toxicity 0.000 abstract description 2
- 230000000052 comparative effect Effects 0.000 description 11
- 239000011347 resin Substances 0.000 description 11
- 229920005989 resin Polymers 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 239000003973 paint Substances 0.000 description 10
- PYSAJDICZJMKGG-UHFFFAOYSA-N 1-hydroxy-2,2,4-trimethylpentan-3-one Chemical compound CC(C)C(=O)C(C)(C)CO PYSAJDICZJMKGG-UHFFFAOYSA-N 0.000 description 8
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 8
- 230000002087 whitening effect Effects 0.000 description 8
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 5
- 239000004816 latex Substances 0.000 description 5
- 229920000126 latex Polymers 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- DAFHKNAQFPVRKR-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylpropanoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)C DAFHKNAQFPVRKR-UHFFFAOYSA-N 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- -1 acrylic ester Chemical class 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- JCTXKRPTIMZBJT-UHFFFAOYSA-N 2,2,4-trimethylpentane-1,3-diol Chemical compound CC(C)C(O)C(C)(C)CO JCTXKRPTIMZBJT-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- VPJOGDPLXNTKAZ-UHFFFAOYSA-N 2-methylpropanoic acid;2,2,4-trimethylpentane-1,3-diol Chemical compound CC(C)C(O)=O.CC(C)C(O)C(C)(C)CO VPJOGDPLXNTKAZ-UHFFFAOYSA-N 0.000 description 2
- HSJKGGMUJITCBW-UHFFFAOYSA-N 3-hydroxybutanal Chemical compound CC(O)CC=O HSJKGGMUJITCBW-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000004060 metabolic process Effects 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000012855 volatile organic compound Substances 0.000 description 2
- 229920003067 (meth)acrylic acid ester copolymer Polymers 0.000 description 1
- 150000000185 1,3-diols Chemical class 0.000 description 1
- CJTNLEQLKKYLFO-UHFFFAOYSA-N 1-butoxyethanol Chemical compound CCCCOC(C)O CJTNLEQLKKYLFO-UHFFFAOYSA-N 0.000 description 1
- TYXULUBCBKMSSK-UHFFFAOYSA-N 1-hydroxypentan-3-one Chemical compound CCC(=O)CCO TYXULUBCBKMSSK-UHFFFAOYSA-N 0.000 description 1
- ITUPVOZAYWZFTF-UHFFFAOYSA-N 3-(hydroxymethyl)heptan-4-one Chemical compound CCCC(=O)C(CC)CO ITUPVOZAYWZFTF-UHFFFAOYSA-N 0.000 description 1
- LVSQXDHWDCMMRJ-UHFFFAOYSA-N 4-hydroxybutan-2-one Chemical compound CC(=O)CCO LVSQXDHWDCMMRJ-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical class OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- 229920000459 Nitrile rubber Polymers 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229920002319 Poly(methyl acrylate) Polymers 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical class CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- NTXGQCSETZTARF-UHFFFAOYSA-N buta-1,3-diene;prop-2-enenitrile Chemical compound C=CC=C.C=CC#N NTXGQCSETZTARF-UHFFFAOYSA-N 0.000 description 1
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- HDERJYVLTPVNRI-UHFFFAOYSA-N ethene;ethenyl acetate Chemical group C=C.CC(=O)OC=C HDERJYVLTPVNRI-UHFFFAOYSA-N 0.000 description 1
- CYKDLUMZOVATFT-UHFFFAOYSA-N ethenyl acetate;prop-2-enoic acid Chemical compound OC(=O)C=C.CC(=O)OC=C CYKDLUMZOVATFT-UHFFFAOYSA-N 0.000 description 1
- 229920001038 ethylene copolymer Polymers 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Paints Or Removers (AREA)
Abstract
Description
本発明は、分子内にカルボニル基と水酸基を有し、カルボニル基と水酸基の間に炭素を有する化合物からなる造膜助剤、およびこの造膜助剤を含有した塗料用組成物に関する。 The present invention relates to a film-forming aid comprising a compound having a carbonyl group and a hydroxyl group in the molecule and having carbon between the carbonyl group and the hydroxyl group, and a coating composition containing the film-forming aid.
近年、トルエンやキシレンに代表される揮発性有機化合物（Volatile Organic Compoud VOC）は、作業環境や生活環境の悪化が懸念されるため、忌避される傾向にあり、有機溶剤系塗料に変わり水系塗料の台頭が著しい。水系エマルション塗料は水系塗料の代表であり塗料の多くの部分を占める媒体に水を用いる塗料である。水系エマルション塗料は塗料が乾燥する際にエマルション内の油滴粒子同士が融着し強固な樹脂塗膜を形成する必要がある。この際、特にＴｇ（ガラス転位点）の高い樹脂を用いた場合、低温での粒子同士の融着が不十分であるため一般に造膜助剤と呼ばれる添加剤を用いる。この造膜助剤として２，２，４−トリメチル−１，３−ペンタンジオールモノイソブチレート（ＣＳ−１２、チッソ株式会社の商品名）や、４−ブトキシ−１−エタノール（ブチルセロソルブ）と言った化合物が市販されているが、エマルションに用いる樹脂の種類によっては造膜効果が十分でないか、造膜助剤の構造が複雑で合成に手間がかかるものであるか（特許文献１）、或いはブチルセロソルブ、エチルセロソルブと言った安全性に問題のあるものであった。ブチルセロソルブ或いはエチルセロソルブといったエチレングリコール誘導体は体内での代謝過程でシュウ酸が形成されるために毒性を発現するとされているため、代謝過程でシュウ酸を生じないプロピレングリコール誘導体への代替が進んでいる（特許文献２）。 In recent years, volatile organic compounds such as toluene and xylene (Volatile Organic Compoud VOC) have been evaded due to concerns about deterioration of the work environment and living environment. The rise is remarkable. Water-based emulsion paints are representative of water-based paints and use water as a medium that occupies a large part of the paint. The water-based emulsion paint needs to form a strong resin coating film by fusing the oil droplet particles in the emulsion when the paint dries. At this time, particularly when a resin having a high Tg (glass transition point) is used, an additive generally referred to as a film-forming aid is used because the particles are not sufficiently fused at low temperatures. As this film-forming auxiliary, 2,2,4-trimethyl-1,3-pentanediol monoisobutyrate (CS-12, trade name of Chisso Corporation) or 4-butoxy-1-ethanol (butyl cellosolve) However, depending on the type of resin used in the emulsion, the film-forming effect may not be sufficient, or the structure of the film-forming aid may be complex and time-consuming to synthesize (Patent Document 1), or Butyl cellosolve and ethyl cellosolve had safety problems. Ethylene glycol derivatives such as butyl cellosolve or ethyl cellosolve are said to be toxic because oxalic acid is formed in the metabolic process in the body, so replacement with propylene glycol derivatives that do not produce oxalic acid in the metabolic process is progressing (Patent Document 2).
更にこれまでは、有機溶剤系塗料が主であったライン塗装においても水系エマルション塗料が台頭してきており、乾燥時における造膜性および乾燥性についても高機能化が求められている。これまでの造膜助剤は塗料の乾燥時、特に水や有機溶剤が蒸発する際には蒸発せず、理想的な塗膜を形成した後に大気中に揮散するというものであったが、迅速な乾燥が求められるライン塗装においては。溶剤が乾燥し理想的な塗膜を形成した後、即座に造膜助剤も蒸発することが求められる。従って、これまで特に建築物の外壁等に利用されてきた高沸点の造膜助剤では乾燥に時間がかかりすぎるという問題を有していた。 Furthermore, until now, water-based emulsion paints have also emerged in line coating, which has mainly been organic solvent-based paints, and there is a demand for higher film forming properties and drying properties during drying. Conventional film-forming aids have been designed to evaporate into the atmosphere after forming an ideal coating film, but do not evaporate when the paint is dried, especially when water or organic solvents evaporate. For line coatings that require dryness. After the solvent is dried and an ideal coating film is formed, it is required that the film-forming auxiliary also evaporates immediately. Therefore, the high boiling point film-forming aid that has been used especially for the outer walls of buildings has been problematic in that it takes too much time to dry.
本発明の目的は、上記従来の技術課題を解決することであり、造膜効果が大きく、毒性が小さくかつ低沸点で合成が容易な造膜助剤および、この造膜助剤を含有する塗料用組成物を提供することである。 An object of the present invention is to solve the above-mentioned conventional technical problems, a film-forming aid having a large film-forming effect, a low toxicity, a low boiling point and easy synthesis, and a paint containing this film-forming aid It is to provide a composition for use.
本発明者らは鋭意検討の結果、特定の構造である化合物が上記要求を満たす造膜助剤として有効である事を見出し、本発明を完成するに至った。 As a result of intensive studies, the present inventors have found that a compound having a specific structure is effective as a film-forming auxiliary that satisfies the above requirements, and have completed the present invention.
本発明は、以下の項（１）〜（７）などを含んでいる。
（１） 式１で表される化合物からなる造膜助剤。
式１において、Ｒ１は炭素数１から４の直鎖または分岐アルキルであり、Ｒ２およびＲ３は独立して、水素または炭素数１から２のアルキルである。
The present invention includes the following items (1) to (7).
(1) A film-forming aid comprising a compound represented by Formula 1.
In Formula 1, R 1 is linear or branched alkyl having 1 to 4 carbon atoms, and R 2 and R 3 are independently hydrogen or alkyl having 1 to 2 carbon atoms.
（２） 式１において、Ｒ１がイソプロピルであり、Ｒ２およびＲ３が共にメチルである項（１）に記載の造膜助剤。 (2) The film-forming aid according to item (1), wherein in formula 1, R 1 is isopropyl and R 2 and R 3 are both methyl.
（３） 項（１）または（２）に記載の造膜助剤をポリウレタン系エマルションに用いること。 (3) The film-forming aid described in item (1) or (2) is used in a polyurethane emulsion.
（４） 項（１）または（２）に記載の造膜助剤を含有する塗料用組成物。 (4) A coating composition containing the film-forming aid according to item (1) or (2).
（５） さらにポリウレタンを含有する項（４）に記載の塗料用組成物。 (5) The coating composition according to item (4), further containing polyurethane.
（６） 塗料用組成物の重量に基づいて、造膜助剤の含有量が０．１重量％から３０．０重量％の範囲である項（４）または（５）に記載の塗料用組成物。 (6) The coating composition according to item (4) or (5), wherein the content of the film-forming auxiliary is in the range of 0.1% by weight to 30.0% by weight based on the weight of the coating composition. object.
（７） 塗料用組成物の重量に基づいて、造膜助剤の含有量が、０．５重量％から２０．０重量％の範囲である項（４）または（５）に記載の塗料用組成物。 (7) The coating composition according to item (4) or (5), wherein the content of the film-forming auxiliary is in the range of 0.5 wt% to 20.0 wt% based on the weight of the coating composition. Composition.
造膜助剤となる式（１）で表される化合物は、具体的には、１−ヒドロキシ−３−ブタノン、２−エチル−１−ヒドロキシ−３−ヘキサノン、２，２，４−トリメチル−１−ヒドロキシ−３−ペンタノンなどが挙げられ、２，２，４−トリメチル−１−ヒドロキシ−３−ペンタノンが特に好ましい。 Specifically, the compound represented by the formula (1) serving as a film-forming aid is 1-hydroxy-3-butanone, 2-ethyl-1-hydroxy-3-hexanone, 2,2,4-trimethyl- Examples include 1-hydroxy-3-pentanone, and 2,2,4-trimethyl-1-hydroxy-3-pentanone is particularly preferable.
式（１）で表される化合物の製造方法としては、１，３−ジオールの脱水素による、または、ケトンへのフォルムアルデヒドのアルドール付加によるなどがある。
一例としては、２，２，４−トリメチル−１,３−ペンタンジオールにラネーニッケル触媒上、９０から１５０℃の温度範囲で加熱し、常圧下または減圧下で３から２０時間反応させる。得られた反応粗液を精留等の公知の方法にて精製を行うことにより、２，２，４−トリメチル−１−ヒドロキシ−３−ペンタノンを得ることができる。
Examples of the method for producing the compound represented by the formula (1) include dehydrogenation of 1,3-diol or addition of aldol of formaldehyde to a ketone.
As an example, 2,2,4-trimethyl-1,3-pentanediol is heated on a Raney nickel catalyst in a temperature range of 90 to 150 ° C. and reacted at normal pressure or reduced pressure for 3 to 20 hours. By purifying the obtained reaction crude liquid by a known method such as rectification, 2,2,4-trimethyl-1-hydroxy-3-pentanone can be obtained.
本発明の造膜助剤が使用される水系エマルションに用いられる樹脂の種類は、ポリアクリル酸メチル、ポリメタクリル酸メチル等のアクリル系樹脂、ポリ乳酸ビニル樹脂等の酢酸ビニル等の酢酸ビニル系樹脂、ポリウレタン系樹脂、あるいはこれらのモノマーを共重合させたコポリマーが好適に使用され、一般的には水系エマルション中の樹脂の含有割合は、１０重量％から６０重量％の範囲である。 The type of resin used in the water-based emulsion in which the film-forming aid of the present invention is used is acrylic resin such as polymethyl acrylate and polymethyl methacrylate, and vinyl acetate resin such as vinyl acetate such as polyvinyl lactate resin. Polyurethane resins or copolymers obtained by copolymerizing these monomers are preferably used, and the content of the resin in the aqueous emulsion is generally in the range of 10% to 60% by weight.
水系エマルションとして使用されるエマルションの種類は、上記の樹脂を水および有機溶剤などの媒体に分散させたエマルションが挙げられ、具体的には、アクリル酸エステルエマルション、メタクリル酸エステルエマルション、ポリウレタンエマルション、酢酸ビニルホモポリマーエマルション、酢酸ビニル−アクリル酸エステルコポリマーエマルション、酢酸ビニル−エチレンコポリマーエマルション、アクリル酸エステル−メタクリル酸エステルコポリマーエマルション、アクリル酸エステル−スチレンコポリマーエマルション等が好適に使用され、アクリル酸エマルション、ポリウレタンエマルションがより好ましく使用される。更に好ましく使用されるエマルションはポリウレタンエマルションである。 Examples of emulsions used as water-based emulsions include emulsions in which the above resins are dispersed in a medium such as water and an organic solvent. Specifically, acrylic ester emulsions, methacrylate ester emulsions, polyurethane emulsions, acetic acid Vinyl homopolymer emulsions, vinyl acetate-acrylic acid ester copolymer emulsions, vinyl acetate-ethylene copolymer emulsions, acrylic acid ester-methacrylic acid ester copolymer emulsions, acrylic acid ester-styrene copolymer emulsions are preferably used. An emulsion is more preferably used. Further preferably used emulsion is a polyurethane emulsion.
本発明における造膜助剤は、水系エマルション以外のいわゆるラテックスにも使用可能である。使用されるラテックスは、塩化ビニリデンコポリマーラテックス、塩化ビニル−コポリマーラテックス、ブタジエン−スチレンラテックス、ブタジエン−アクリロニトリルラテックスなどが挙げられる。 The film-forming aid in the present invention can be used for so-called latexes other than water-based emulsions. Examples of the latex used include vinylidene chloride copolymer latex, vinyl chloride-copolymer latex, butadiene-styrene latex, butadiene-acrylonitrile latex, and the like.
式１において、Ｒ１は炭素数１から４の直鎖または分岐のアルキルであり、Ｒ２およびＲ３は独立して水素または炭素数１から２のアルキルである。Ｒ１は炭素数２または３のアルキルが好ましく、Ｒ２およびＲ３は独立して、炭素数１から２のアルキルが好ましい。さらに好ましくは、Ｒ１は炭素数３のアルキルであり、Ｒ２およびＲ３は独立して炭素数１のアルキル、すなわちメチルが好ましい。Ｒ１が炭素数３のイソプロピルであり、Ｒ２およびＲ３が共にメチルである２，２，４−トリメチル−１−ヒドロキシ−３−ペンタノンが極めて好ましい。 In Formula 1, R 1 is linear or branched alkyl having 1 to 4 carbon atoms, and R 2 and R 3 are independently hydrogen or alkyl having 1 to 2 carbon atoms. R 1 is preferably alkyl having 2 or 3 carbon atoms, and R 2 and R 3 are independently preferably alkyl having 1 to 2 carbon atoms. More preferably, R 1 is alkyl having 3 carbon atoms, and R 2 and R 3 are preferably independently alkyl having 1 carbon atom, that is, methyl. 2,2,4-trimethyl-1-hydroxy-3-pentanone, in which R 1 is isopropyl having 3 carbon atoms and R 2 and R 3 are both methyl, is very preferred.
水系エマルションや塗料用組成物中の造膜助剤の測定法は公知の方法、例えばガスクロマト分析等にて分析可能である。また、水系エマルションや樹脂組成物における樹脂などの不揮発分の測定方法も公知の方法例えば、蒸発残分の測定等にて分析可能である。 The method for measuring the film-forming aid in the aqueous emulsion or coating composition can be analyzed by a known method such as gas chromatography analysis. Moreover, the measuring method of non volatile matters, such as resin in a water-system emulsion or a resin composition, can also be analyzed by a well-known method, for example, measurement of an evaporation residue, etc.
本発明における造膜助剤の塗料用組成物に対する添加量は、当該塗料用組成物の総重量に対する添加割合で定義できる。例えば、当該塗料用組成物の総重量に対し、造膜助剤の添加割合が０．１重量％から３０．０重量％の範囲で使用可能であり、好ましくは０．５重量％から２０．０重量％の範囲である。添加量が０．１重量％以上で造膜効果が十分となり、３０．０重量％以下で造膜速度が充分速くなる。 The addition amount of the film-forming aid in the present invention relative to the coating composition can be defined by the ratio of addition relative to the total weight of the coating composition. For example, the film forming aid can be used in a range of 0.1 wt% to 30.0 wt%, preferably 0.5 wt% to 20 wt% with respect to the total weight of the coating composition. It is in the range of 0% by weight. When the addition amount is 0.1% by weight or more, the film forming effect is sufficient, and when it is 30.0% by weight or less, the film forming speed is sufficiently high.
本発明における造膜助剤の含有量は、当該水系エマルションや塗料用組成物中の含有樹脂重量に対する添加割合でも定義できる。例えば、当該水系エマルションや塗料用組成物中に含有される樹脂重量に対し、造膜助剤の添加割合が０．１重量％から１００．０重量％の範囲での使用が好ましく、より好ましくは１．０重量％から５０．０重量％の範囲であり、さらに好ましくは２．０重量％から３０．０重量％の範囲である。０．１重量％以上で造膜効果が十分となり、１００．０重量％以下で造膜速度が充分速くなる。 The content of the film-forming aid in the present invention can also be defined by an addition ratio with respect to the weight of the resin contained in the aqueous emulsion or coating composition. For example, it is preferable to use the film forming aid in a range of 0.1 wt% to 100.0 wt% with respect to the resin weight contained in the aqueous emulsion or paint composition, more preferably It is in the range of 1.0 wt% to 50.0 wt%, more preferably in the range of 2.0 wt% to 30.0 wt%. When the amount is 0.1% by weight or more, the film forming effect is sufficient.
以下、実施例により本発明の効果を具体的に説明するが、本発明はこれらに限定されるものではない。 Hereinafter, the effects of the present invention will be specifically described by way of examples, but the present invention is not limited thereto.
（塗料組成物の調製）
実施例、比較例には、水系エマルションはＤＩＣ株式会社のポリウレタン系エマルション ハイドランＡＰ３０Ｆ（登録商標）及びアクリル系エマルション ボンコートＥＤ８５Ｅ、ボンコートＡＮ１５５Ｅ（登録商標）を用いた。実施例には、造膜助剤は本発明の造膜助剤である２，２，４−トリメチル−１−ヒドロキシ−３−ペンタノン（表１から表４ではＣＳ−８ＯＸと略する）を用い、比較例には、２−ブトキシエタノール（ブチルセロソルブ、和光純薬製、表１から表４ではＢＣと略する）、およびチッソ株式会社の２，２，４−トリメチル−１,３−ペンタンジオールモノイソブチレート（表１から表４ではＣＳ−１２と略する）を用いた。なお、２，２，４−トリメチル−１−ヒドロキシ−３−ペンタノンは、２，２，４−トリメチル−１，３−ペンタジオール（チッソ株式会社製）をラネーニッケルを触媒として、液相で脱水素を行い得られた反応粗液から公知の精留にて精製を行って得た。用いた造膜助剤は各々のエマルションに対し１重量％から５重量％の割合で添加し、ホモジナイザーを用いて混合した後、消泡するのを待って測定に供した。
（最低造膜温度および白化温度の測定）
(Preparation of coating composition)
In Examples and Comparative Examples, DIC Corporation polyurethane emulsion Hydran AP30F (registered trademark) and acrylic emulsion Boncoat ED85E and Boncoat AN155E (registered trademark) were used as water-based emulsions. In the examples, 2,2,4-trimethyl-1-hydroxy-3-pentanone (abbreviated as CS-8OX in Tables 1 to 4), which is the film forming aid of the present invention, was used as the film forming aid. Comparative examples include 2-butoxyethanol (butyl cellosolve, manufactured by Wako Pure Chemical Industries, Ltd., abbreviated as BC in Tables 1 to 4), and 2,2,4-trimethyl-1,3-pentanediol mono from Chisso Corporation. Isobutyrate (abbreviated as CS-12 in Tables 1 to 4) was used. In addition, 2,2,4-trimethyl-1-hydroxy-3-pentanone is dehydrogenated in a liquid phase using 2,2,4-trimethyl-1,3-pentadiol (manufactured by Chisso Corporation) as a catalyst for Raney nickel. It was obtained by performing purification by a known rectification from the reaction crude liquid obtained. The film-forming aid used was added in a ratio of 1 to 5% by weight to each emulsion, mixed using a homogenizer, and then waited for defoaming before being used for measurement.
(Measurement of minimum film-forming temperature and whitening temperature)
調製したハイドランＡＰ３０Ｆを水系エマルションとして用い、各々の造膜助剤を含んだ塗料組成物の最低造膜温度及び白化温度を測定した。
最低造膜温度の測定は、井元製作所製 簡易型最低造膜温度測定装置に循環型冷却液送液装置を接続し測定を行った。最低造膜温度及び白化温度の測定はＪＩＳ Ｋ−６８２８−２に則って行った。結果を表１および表２に示した。
ポリウレタン系エマルションであるＡＰ３０Ｆを用いた場合では、２，２，４−トリメチル−１−ヒドロキシ−３−ペンタノン（実施例１−１から１−５）は、ブチルセロソルブ（比較例２−１から２−５）および２，２，４−トリメチル−１,３−ペンタンジオールモノイソブチレート（比較例３−１から３−３）と比較して、どの添加割合においても最低造膜温度、白化温度共に低く、無添加（比較例１）との最低造膜温度の差（ΔＭＦＴ）は、５重量％の添加では５０℃を超えた。
Using the prepared hydran AP30F as an aqueous emulsion, the minimum film-forming temperature and the whitening temperature of each coating composition containing each film-forming aid were measured.
The measurement of the minimum film-forming temperature was performed by connecting a circulation type coolant supply device to a simple minimum film-forming temperature measuring device manufactured by Imoto Seisakusho. The minimum film forming temperature and the whitening temperature were measured according to JIS K-6828-2. The results are shown in Tables 1 and 2.
When AP30F, which is a polyurethane-based emulsion, was used, 2,2,4-trimethyl-1-hydroxy-3-pentanone (Examples 1-1 to 1-5) was converted into butyl cellosolve (Comparative Examples 2-1 to 2- 5) and 2,2,4-trimethyl-1,3-pentanediol monoisobutyrate (Comparative Examples 3-1 to 3-3), both the minimum film-forming temperature and the whitening temperature at any addition ratio The difference in the minimum film-forming temperature (ΔMFT) from the low additive-free (Comparative Example 1) exceeded 50 ° C. with the addition of 5% by weight.
ボンコートＥＤ８５Ｅを水系エマルションとして用いた以外は全て実施例１と同様に最低造膜温度及び白化温度の測定を行った。結果を表３に示した。無添加を比較例４とした。
２，２，４−トリメチル−１−ヒドロキシ−３−ペンタノン（実施例２−１から２−３）は、最低造膜温度、白化温度共に、ブチルセロソルブ（比較例５−１から５−３）および２，２，４−トリメチル−１,３−ペンタンジオールモノイソブチレート（比較例６−１から６−３）と比較してほぼ同様の値を示した。
The minimum film-forming temperature and the whitening temperature were measured in the same manner as in Example 1 except that Boncoat ED85E was used as an aqueous emulsion. The results are shown in Table 3. The additive was determined as Comparative Example 4.
2,2,4-Trimethyl-1-hydroxy-3-pentanone (Examples 2-1 to 2-3) has a minimum film-forming temperature and a whitening temperature, both butyl cellosolve (Comparative Examples 5-1 to 5-3) and Compared with 2,2,4-trimethyl-1,3-pentanediol monoisobutyrate (Comparative Examples 6-1 to 6-3), almost the same value was shown.
ボンコートＡＮ１５５Ｅを水系エマルションとして用いた以外は全て実施例１と同様に最低造膜温度及び白化温度の測定を行った。結果を表４に示した。無添加を比較例７とした。
２，２，４−トリメチル−１−ヒドロキシ−３−ペンタノン（実施例３−１から３−３）は、最低造膜温度、白化温度共に、ブチルセロソルブ（比較例８−１から８−３）および２，２，４−トリメチル−１,３−ペンタンジオールモノイソブチレート（比較例９−１から９−３）と比較してほぼ同様の値を示した。
The minimum film-forming temperature and the whitening temperature were measured in the same manner as in Example 1 except that Boncoat AN155E was used as an aqueous emulsion. The results are shown in Table 4. No addition was designated as Comparative Example 7.
2,2,4-Trimethyl-1-hydroxy-3-pentanone (Examples 3-1 to 3-3) has butyl cellosolve (Comparative Examples 8-1 to 8-3) and a minimum film-forming temperature and a whitening temperature. Compared with 2,2,4-trimethyl-1,3-pentanediol monoisobutyrate (Comparative Examples 9-1 to 9-3), almost the same value was shown.
本発明における造膜助剤は、水系エマルションに加える造膜助剤として、特にポリウレタン系エマルションへの造膜助剤として非常に有効である。 The film-forming aid in the present invention is very effective as a film-forming aid added to an aqueous emulsion, particularly as a film-forming aid to a polyurethane-based emulsion.
Claims (7)
式１において、Ｒ１は炭素数１から４の直鎖または分岐アルキルであり、Ｒ２およびＲ３は独立して、水素または炭素数１から２のアルキルである。 A film-forming auxiliary comprising the compound represented by Formula 1.
In Formula 1, R 1 is linear or branched alkyl having 1 to 4 carbon atoms, and R 2 and R 3 are independently hydrogen or alkyl having 1 to 2 carbon atoms.
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| US3221441A (en) * | 1960-02-23 | 1965-12-07 | William J Shapiro | Toy aircraft and blank |
| JPH03141355A (en) * | 1989-10-27 | 1991-06-17 | Mitsubishi Kasei Corp | Production of planographic printing plate |
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