JPH01226847A - Composition - Google Patents
CompositionInfo
- Publication number
- JPH01226847A JPH01226847A JP5226888A JP5226888A JPH01226847A JP H01226847 A JPH01226847 A JP H01226847A JP 5226888 A JP5226888 A JP 5226888A JP 5226888 A JP5226888 A JP 5226888A JP H01226847 A JPH01226847 A JP H01226847A
- Authority
- JP
- Japan
- Prior art keywords
- methoxyacetone
- peroxide
- composition
- polymerization
- useful
- 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.)
- Pending
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 12
- CUZLJOLBIRPEFB-UHFFFAOYSA-N 1-methoxypropan-2-one Chemical compound COCC(C)=O CUZLJOLBIRPEFB-UHFFFAOYSA-N 0.000 claims abstract description 28
- 150000002978 peroxides Chemical class 0.000 claims abstract description 17
- 150000001875 compounds Chemical class 0.000 abstract description 7
- 239000002904 solvent Substances 0.000 abstract description 6
- 239000011248 coating agent Substances 0.000 abstract description 4
- 238000000576 coating method Methods 0.000 abstract description 4
- 238000006116 polymerization reaction Methods 0.000 abstract description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 2
- 239000000178 monomer Substances 0.000 abstract description 2
- 150000001451 organic peroxides Chemical class 0.000 abstract description 2
- 239000001301 oxygen Substances 0.000 abstract description 2
- 229910052760 oxygen Inorganic materials 0.000 abstract description 2
- 229920000642 polymer Polymers 0.000 abstract description 2
- 239000003505 polymerization initiator Substances 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract description 2
- 239000000470 constituent Substances 0.000 abstract 1
- 230000000977 initiatory effect Effects 0.000 abstract 1
- 238000010526 radical polymerization reaction Methods 0.000 abstract 1
- 239000010408 film Substances 0.000 description 7
- 230000000704 physical effect Effects 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical group CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- 239000008199 coating composition Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 235000021388 linseed oil Nutrition 0.000 description 2
- 239000000944 linseed oil Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- FJWGYAHXMCUOOM-QHOUIDNNSA-N [(2s,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6s)-4,5-dinitrooxy-2-(nitrooxymethyl)-6-[(2r,3r,4s,5r,6s)-4,5,6-trinitrooxy-2-(nitrooxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-3,5-dinitrooxy-6-(nitrooxymethyl)oxan-4-yl] nitrate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O)O[C@H]1[C@@H]([C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@@H](CO[N+]([O-])=O)O1)O[N+]([O-])=O)CO[N+](=O)[O-])[C@@H]1[C@@H](CO[N+]([O-])=O)O[C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O FJWGYAHXMCUOOM-QHOUIDNNSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 229920005603 alternating copolymer Polymers 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000001867 hydroperoxy group Chemical group [*]OO[H] 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- -1 methoxyacetone forms peroxides Chemical class 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 238000005502 peroxidation Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000003021 water soluble solvent Substances 0.000 description 1
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明はメトキシアセトンおよびその過酸化物からなる
組成物に関する。DETAILED DESCRIPTION OF THE INVENTION (Industrial Field of Application) The present invention relates to a composition comprising methoxyacetone and its peroxide.
（従来の技術）
メトキシアセトンは分子内にカルゲニル基とエーテル結
合金あわせ持つ特異な構造から、極性に富み、水性媒体
に対する相溶性も大キく、広範囲な利用範囲が期待され
る吸これまでわずかに塩化ビニル系、酢酸ビニル系、ニ
トロセルロース系樹脂に対する溶剤としての利用が知ら
れてｈるに過ぎない（米国粋計第３６２５８３６号明細
書）。(Prior art) Methoxyacetone has a unique structure in which it has both a cargenyl group and an ether-bonded gold in its molecule, making it highly polar and highly compatible with aqueous media. The only known use is as a solvent for vinyl chloride, vinyl acetate, and nitrocellulose resins (US Ikei No. 3,625,836).
（発明が解決しようとする課題）
メトキシアセトンについてはこれ１で物性がほとんと知
られておらず、本発明者らの知る限りでは上記文献に記
載されている以外には具体的用途が知られていないのが
現状である。(Problems to be Solved by the Invention) The physical properties of methoxyacetone are largely unknown, and as far as the present inventors know, there are no known specific uses other than those described in the above documents. The current situation is that this is not the case.
（課題を解決するための手段ン
本発明者らはこのたびメトキシアセトンの基礎物性を中
心に鋭意検討を重ねた結果、この化合物は意外なことに
温和な条件下に過酸化物を形成する能力を有しているこ
とを見出し次。本発明者らはかかる知見に基づきさらに
検討を進めた結果、メトキシアセトンおよびその過酸化
物からなる組成物が以下に述べる如き興味ある性質を示
すこと全見出し、本発明を完成するに至った。(Means for solving the problem) The present inventors have conducted extensive studies focusing on the basic physical properties of methoxyacetone, and have found that this compound has the unexpected ability to form peroxides under mild conditions. Based on this knowledge, the present inventors conducted further studies and found that a composition consisting of methoxyacetone and its peroxide exhibits the following interesting properties. , we have completed the present invention.
メトキシアセトンｔ！ ０４Ｈ８０□０分子式で表わさ
れ、１．４−ジオキサンと異性体の関係にある沸点１１
６℃／ ７６０ ｖｍＨｇの無色の液体である。本発明
者らによる物性測定によればこの化合物はトルエン希釈
比３．９、蒸発速度１８０（酢酸ブチルｔ１００とした
値）の値を示した。これらの物性値から判断するとメト
キシアセトンはメチルイソブチルケトン（ＭＩＢＫ ）
に近い物性？有しながら水とは任意の組成で混和し、水
溶性の良溶剤としての期待がもてる。Methoxyacetone! 04H80□0 Boiling point 11, which is represented by the molecular formula and has an isomer relationship with 1,4-dioxane
It is a colorless liquid at 6°C/760 vmHg. According to physical property measurements by the present inventors, this compound exhibited a toluene dilution ratio of 3.9 and an evaporation rate of 180 (value based on butyl acetate t100). Judging from these physical property values, methoxyacetone is methyl isobutyl ketone (MIBK).
Physical properties close to ? However, it is miscible with water in any composition, and is expected to be a good water-soluble solvent.
メトキシアセトンの基礎物性についてさらに詳細なる検
討を行なった結果、メトキシアセトンは室温、空気接触
程度の温和な条件下に過酸化物を形成することがわかっ
た。例えばメトキシアセトンに室温下、数分〜数時間、
好ましくは３０分〜数時間空気を吹き込むだけで、０．
１〜２．０モルチ程度の過酸化物が形成される（ヨート
メ） ＩＪ−法にて定量可）。この過酸化物含有メトキ
シアセトンは加熱すると酢酸および蟻酸メチルが副生ず
ることなどからメトキシアセトンの過酸化＋！５！ｌは
アセチル基とメトキシ基の間のメチレン基中の１個の水
素がヒドロペルオキシ基ＫＷ換された構造を有するもの
と推定される。従ってラジカル重合性の二重結合を有す
るモノマー、オリゴマー、Ｉリマー等を前述のように調
製した過酸化ｖｌＪ廿有メトキシアセトンに溶解した場
合、または重合性二車結合を有する化合物のメトキシア
セトン溶液ｔ２素に接触させた場合は容易に重合硬化が
進行する。As a result of a more detailed study of the basic physical properties of methoxyacetone, it was found that methoxyacetone forms peroxides under mild conditions such as room temperature and air contact. For example, add methoxyacetone to room temperature for several minutes to several hours.
Preferably, just by blowing air for 30 minutes to several hours, 0.
Approximately 1 to 2.0 mole peroxide is formed (quantitative by IJ-method). When this peroxide-containing methoxyacetone is heated, acetic acid and methyl formate are produced as by-products, so methoxyacetone peroxidation +! 5! It is presumed that l has a structure in which one hydrogen in the methylene group between the acetyl group and the methoxy group is replaced with a hydroperoxy group KW. Therefore, when monomers, oligomers, I-limers, etc. having radically polymerizable double bonds are dissolved in peroxide vlJ 廿 methoxyacetone prepared as described above, or when a methoxyacetone solution of a compound having a polymerizable divalent bond is dissolved in t2 If it is brought into contact with a base material, polymerization and curing will proceed easily.
たとえばこれらの溶液を空気雰囲下に基板上に薄膜状に
塗布した場合、硬化被膜を得ることができる。不飽和化
合物としてアマニ油を選び、基板上に薄膜状に塗布し硬
化速度を比較した結果、メトキシアセトン溶液の糸は短
時間で硬化し被膜が形成されたが、メトキシアセトンを
用いない系は硬化被膜が得られなかった。For example, when these solutions are applied in the form of a thin film onto a substrate in an air atmosphere, a cured film can be obtained. We selected linseed oil as the unsaturated compound and applied it in a thin film onto a substrate and compared the curing speed.The results showed that the threads in the methoxyacetone solution cured in a short time to form a film, but the system without methoxyacetone did not cure. No coating was obtained.
メトキシアセトンは上述の性能、即ち優れた溶解力とラ
ジカル重合の開始・促進能力１有するので、本発明の組
成物はこの性能によって工業的に広い用途を有する有橋
過酸化物の原料として有用であるばかりでなく、重合開
始剤の添加全必要としない塗料組成物の構成に有用であ
り、該塗料組成物は１合硬化性塗料として特別な硬化手
段を必要としない点で塗装作業上極めて有用である。従
って本発明の組成物は新しいタイプの複合機能溶剤とし
て広範囲な利用が期待される。Methoxyacetone has the above-mentioned properties, that is, excellent dissolving power and the ability to initiate and promote radical polymerization1, so the composition of the present invention is useful as a raw material for bridged peroxides, which have a wide range of industrial applications. Not only that, it is useful for constructing a coating composition that does not require the addition of a polymerization initiator, and the coating composition is extremely useful for painting work in that it does not require any special curing means as a single-curing coating. It is. Therefore, the composition of the present invention is expected to be widely used as a new type of multifunctional solvent.
メトキシアセトンの合成はメトキシデロノセノールの（
酸化）脱水素反応により液相又は気相にて容易に実施で
きる。The synthesis of methoxyacetone is made from methoxyderonosenol (
It can be easily carried out in liquid phase or gas phase by oxidation) dehydrogenation reaction.
以下、実施例により本発明を具体的に説明するが、本発
明は実施例により制限を受けるものではない。EXAMPLES Hereinafter, the present invention will be specifically explained with reference to Examples, but the present invention is not limited by the Examples.
実施例１゜
ガスフィードロ、還流冷却器、温度計、攪拌装置を備え
九内容２００ｍの三つロフラスコにメトキシアセトン５
０ゴを仕込み、室温にて攪拌下に空気を１’０１ ／
ｈｒの流速で導入した。空気を導入しながら攪拌を１０
時間実施し、１時間毎にサンプリングを行なって、イン
グロノ９ノール／氷酢ｒＲ溶媒系におけるヨードメトリ
ー法により過酸化物の定ｊｉ金行なった。空気導入前お
よび空気導入開始１，３．５．１０時間後における活性
酸素量と過酸化物生成量（モル％）を下表にまとめて示
す。Example 1 5 5 of methoxyacetone was placed in a 200 m three-necked flask equipped with a gas feeder, reflux condenser, thermometer, and stirrer.
Pour 1'01 of air into the mixture and stir at room temperature.
It was introduced at a flow rate of hr. Stir for 10 minutes while introducing air.
Peroxide determinations were carried out by iodometry in the Inglono9ol/glacial vinegar rR solvent system with hourly sampling. The amount of active oxygen and the amount of peroxide produced (mol %) before air introduction and 1, 3, 5, and 10 hours after the start of air introduction are summarized in the table below.
注）過酸化物の定量法は小力等者”有機過酸化物”によ
った。Note: The method for quantifying peroxide was based on the organic peroxide method.
実施例２゜
縁どりをした内径１００■の円形ガラス板上に、アマニ
油０．５．９と実施例１にて得られた過酸化物含有メト
キシアセトンｏ、 ｓ ｇ ２よく混合した溶液を広げ
、室内の大気中に放置することにより被膜が形成される
までの時間全測定した。被膜形成までに１０日間を要し
た。Example 2 Spread a well-mixed solution of linseed oil 0.5.9 and peroxide-containing methoxyacetone o, s g obtained in Example 1 on a circular glass plate with an inner diameter of 100 mm and a border. The total time until a film was formed by leaving it in the indoor air was measured. It took 10 days to form a film.
比較例１゜
実施例２において過酸化物含有メトキシアセトンを用い
なかった以外は実施例２と同様の操作を行なった。放置
後２０日間を過ぎても被膜の形成は認められず、流動性
を有していた。Comparative Example 1 The same operation as in Example 2 was carried out except that the peroxide-containing methoxyacetone was not used in Example 2. No film formation was observed even after 20 days of standing, and the film remained fluid.
比較例２゜
実施例２において過酸化物含有メトキシアセトンのかわ
シに酢酸エチルｏ、ｓ、ｐｌ用いた以外は実施例２と同
様の操作を行なった。放置後２０日間を過ぎても被膜の
形成は認められなかった。Comparative Example 2 The same operation as in Example 2 was carried out except that ethyl acetate o, s, and pl were used as a substitute for peroxide-containing methoxyacetone. No film formation was observed even after 20 days of standing.
実施例３゜
無水マレイン酸０．９８ｇ及び３−メチル−３−１テニ
ルアセテ−）１．２８．１−メトキシアセトン２０１１
１に溶解し、２７℃で空気雰囲気下に放置したところ、
徐々に増粘し粘稠な液体となった。次に得られた溶液１
５０−のメチルイソブチルケトンに注いだところ、白色
粉末状の交互共重合体が得られた。Example 3 Maleic anhydride 0.98 g and 3-methyl-3-1-thenyl acetate) 1.28.1-methoxyacetone 2011
When dissolved in 1 and left in an air atmosphere at 27°C,
The viscosity gradually increased and became a viscous liquid. Next obtained solution 1
When poured into 50-methyl isobutyl ketone, a white powdery alternating copolymer was obtained.
比較例３゜
実施例３においてメトキシアセトンをベンゼンに変えた
以外は同様に行ったが、ポリマーの生成は認められなか
った。Comparative Example 3 The same procedure as in Example 3 was repeated except that benzene was used instead of methoxyacetone, but no polymer formation was observed.
（発明の効果）
本発明により提供されるメトキシアセトンおよびその過
酸化物からなる組成物は、優れた溶解力とう・ブチル重
合の開始・促進能力１有しており、重合硬化性塗料の構
成要素として、あるいは新しいタイプの複合機能溶剤と
して広範囲な利用が期待される。(Effects of the Invention) The composition comprising methoxyacetone and its peroxide provided by the present invention has excellent dissolving power and the ability to initiate and accelerate butyl polymerization, and is a component of polymerizable curable paints. It is expected to be widely used as a solvent or as a new type of multi-functional solvent.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5226888A JPH01226847A (en) | 1988-03-04 | 1988-03-04 | Composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5226888A JPH01226847A (en) | 1988-03-04 | 1988-03-04 | Composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH01226847A true JPH01226847A (en) | 1989-09-11 |
Family
ID=12910027
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5226888A Pending JPH01226847A (en) | 1988-03-04 | 1988-03-04 | Composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH01226847A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5342865A (en) * | 1992-04-24 | 1994-08-30 | The Dow Chemical Company | Solvent system |
| US5407977A (en) * | 1993-04-20 | 1995-04-18 | The Dow Chemical Company | Solvent system |
| JP2019145383A (en) * | 2018-02-22 | 2019-08-29 | トヨタ自動車株式会社 | Electrolyte and lithium ion battery |
-
1988
- 1988-03-04 JP JP5226888A patent/JPH01226847A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5342865A (en) * | 1992-04-24 | 1994-08-30 | The Dow Chemical Company | Solvent system |
| AU654619B2 (en) * | 1992-04-24 | 1994-11-10 | Dow Chemical Company, The | Solvent mixture |
| US5407977A (en) * | 1993-04-20 | 1995-04-18 | The Dow Chemical Company | Solvent system |
| JP2019145383A (en) * | 2018-02-22 | 2019-08-29 | トヨタ自動車株式会社 | Electrolyte and lithium ion battery |
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