JPS5851995B2 - Stabilization method for 1,1,2↓-trichloro↓-1,2,2↓-trifluoroethane solvent - Google Patents
Stabilization method for 1,1,2↓-trichloro↓-1,2,2↓-trifluoroethane solventInfo
- Publication number
- JPS5851995B2 JPS5851995B2 JP14710878A JP14710878A JPS5851995B2 JP S5851995 B2 JPS5851995 B2 JP S5851995B2 JP 14710878 A JP14710878 A JP 14710878A JP 14710878 A JP14710878 A JP 14710878A JP S5851995 B2 JPS5851995 B2 JP S5851995B2
- Authority
- JP
- Japan
- Prior art keywords
- freon
- mixed solvent
- solvent
- added
- weight
- 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
- 239000002904 solvent Substances 0.000 title claims description 12
- 238000000034 method Methods 0.000 title claims description 5
- 230000006641 stabilisation Effects 0.000 title description 2
- 238000011105 stabilization Methods 0.000 title description 2
- 150000002828 nitro derivatives Chemical class 0.000 claims description 12
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 claims description 10
- 230000000087 stabilizing effect Effects 0.000 claims description 8
- AJDIZQLSFPQPEY-UHFFFAOYSA-N 1,1,2-Trichlorotrifluoroethane Chemical compound FC(F)(Cl)C(F)(Cl)Cl AJDIZQLSFPQPEY-UHFFFAOYSA-N 0.000 description 28
- 239000012046 mixed solvent Substances 0.000 description 24
- 239000003381 stabilizer Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 239000002184 metal Substances 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 125000002947 alkylene group Chemical group 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910001369 Brass Inorganic materials 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 235000002597 Solanum melongena Nutrition 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- -1 aliphatic alcohols Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 239000010951 brass Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000005108 dry cleaning Methods 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- 125000004971 nitroalkyl group Chemical group 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
Landscapes
- Detergent Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【発明の詳細な説明】
本発明は1,1.2−トリクロロ−1,2,2−トリフ
ルオロエタン(以下フロン113と称する)およびその
混合溶剤に関するものであり、更に詳しくはフロン11
3およびその混合溶剤にニトロ化合物とグリシドールを
添加することによって溶剤の分解を防止し、金属材料の
腐食防止を図ろうとするものである。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to 1,1,2-trichloro-1,2,2-trifluoroethane (hereinafter referred to as Freon 113) and its mixed solvent.
By adding a nitro compound and glycidol to No. 3 and its mixed solvent, the decomposition of the solvent is prevented and the corrosion of metal materials is prevented.
本発明で言う1,1.2−1リクロロ−1,2゜2−ト
リフルオロエタン系溶剤とはフロン113およびフロン
113を含む混合溶剤をさし、このフロン113含有混
合溶剤とは、フロン113の特性を損なわない範囲で種
々の有機溶剤と混合し変性したものであり、かかる目的
に使用される有機溶剤の例として、メタノール、エタノ
ール、イソ−プロパツール等の低級脂肪族アルコール、
アセトン、メチルエチルケトン等のカルボニル基を持つ
化合物および、塩化メチレンをはじめとする各種のハロ
ゲン化炭化水素等を挙げることが出来る。In the present invention, the 1,1.2-1-lichloro-1,2゜2-trifluoroethane solvent refers to a mixed solvent containing Freon 113 and Freon 113, and the mixed solvent containing Freon 113 refers to Freon 113. Examples of organic solvents used for this purpose include lower aliphatic alcohols such as methanol, ethanol, and isopropanol;
Examples include compounds having a carbonyl group such as acetone and methyl ethyl ketone, and various halogenated hydrocarbons including methylene chloride.
フロン113お゛よびその混合溶剤は優れた安定性に加
えて不燃性、低毒性、選択的溶解性等の点で優れた特性
を有しているので、プラスチック、エラストマー、金属
等の被洗浄物構成材料を侵すことなく、目的の油脂等の
汚れだけを良く溶解除去できる溶剤としてフィルム、磁
気テープの洗浄、プリント基板、リレー・モーター等の
電子、電気関係機器の洗浄、レンズ、時計等の光学、精
密機器関係の洗浄、プラスチックの加工における仕上げ
洗浄あるいはドライクリーニング等に広く使用されてい
る。Freon 113 and its mixed solvents have excellent properties such as nonflammability, low toxicity, and selective solubility in addition to excellent stability, so they can be used to clean objects such as plastics, elastomers, and metals. As a solvent that can effectively dissolve and remove target oils and other dirt without attacking the constituent materials, it can be used to clean films, magnetic tapes, electronic and electrical equipment such as printed circuit boards, relays and motors, and optical equipment such as lenses and watches. It is widely used for cleaning precision equipment, finishing cleaning in plastic processing, dry cleaning, etc.
上述のごとく、フロン113系溶剤は一般に安定性が高
いので通常の使用条件下ではテトラクロルエチレン、ト
リクロルエチレンあるいは1,1゜1−トリクロルエタ
ン等の塩素系溶剤にみられる安定剤の添加は不必要とさ
れている。As mentioned above, Freon 113 solvents are generally highly stable, so under normal usage conditions, it is not necessary to add stabilizers found in chlorinated solvents such as tetrachlorethylene, trichlorethylene, or 1,1°1-trichloroethane. is necessary.
ところが、該溶剤に鉄、アルミニウム、銅、真鍮をはじ
めとする各種金属の接触下において、多量の水が混入し
た場合にはかかる安定性を長期間維持することが困難と
なり、加水分解により溶剤が劣化するばかりか、生成し
た酸が被洗浄物あるいは洗浄機等を腐食する場合がある
。However, if a large amount of water is mixed into the solvent when it comes into contact with various metals such as iron, aluminum, copper, and brass, it becomes difficult to maintain such stability for a long period of time, and the solvent is degraded by hydrolysis. Not only does it deteriorate, but the generated acid may corrode the object to be cleaned or the cleaning machine.
これらの傾向はフロン113単一の溶剤よりも前記混合
系溶剤について顕著である。These trends are more pronounced for the mixed solvent than for the single Freon 113 solvent.
ところでフロン113系溶剤の安定性を向上させる方法
として、従来第一級、第二級アルキルアミン(特公昭4
0−13724号公報)、プロピレンオキサイドとニト
ロメタンの混合物(特公昭45−12488号公報)、
ハロゲン化ベンゼン(特公昭45−32048号公報)
、ベンズイミダゾール類0持公昭45−35319号公
報)あるいはエポキシドとオレフィンの混合物(特公昭
49−37031号公報)等の各種安定剤が提案されて
いる。By the way, as a method to improve the stability of Freon 113-based solvents, conventionally, primary and secondary alkyl amines (Special Publications
0-13724), a mixture of propylene oxide and nitromethane (Japanese Patent Publication No. 45-12488),
Halogenated benzene (Japanese Patent Publication No. 45-32048)
Various stabilizers have been proposed, such as benzimidazole compounds (Japanese Patent Publication No. 49-37031) and mixtures of epoxides and olefins (Japanese Patent Publication No. 37031-1982).
しかしながら、これらの安定剤は水と金属の共存する様
な厳しい条件下では必ずしも満足できるものではなかっ
た。However, these stabilizers were not necessarily satisfactory under severe conditions where water and metal coexist.
そこで本発明者らはフロン113およびその混合溶剤の
安定性を向上させるために各種の安定剤について検討を
行なった結果、ニトロメタンおよび/またはニトロエタ
ンのような炭素数が1〜6のニトロアルカン(以下ニト
ロ化合物と称する)とグリシドールの両化合物を組合せ
て添加することによって驚くべき高安定化効果の発揮さ
れることを見出し、本発明に到達したものである。Therefore, the present inventors investigated various stabilizers to improve the stability of Freon 113 and its mixed solvent, and found that nitroalkanes having 1 to 6 carbon atoms such as nitromethane and/or nitroethane (hereinafter referred to as The inventors have discovered that a surprisingly high stabilizing effect can be achieved by adding a combination of both compounds (referred to as nitro compounds) and glycidol, and have arrived at the present invention.
すなわち、本発明はフロン113およびその混合溶剤に
ニトロ化合物、好ましくはニトロメタンおよび/または
ニトロエタンとグリシドールを組合せて添加することを
特徴とする新規な安定化法であって、その目的とすると
ころは金属および水の共存するごとき厳しい条件下にも
良い安定性を維持できるフロン113およびその混合溶
剤の安定化方法を提供するものである。That is, the present invention is a novel stabilization method characterized by adding a nitro compound, preferably nitromethane and/or nitroethane in combination with glycidol, to Freon 113 and its mixed solvent. The object of the present invention is to provide a method for stabilizing Freon 113 and its mixed solvent, which can maintain good stability even under severe conditions such as the coexistence of water.
フロン113およびその混合溶剤にニトロ化合物あるい
はグリシドールを各々単独に添加した場合には安定化効
果が小さいか;あるいは全く安定化効果が発揮されない
のに対して、単にこれらを組合せて添加することによっ
て著しい安定化効果がみとめられたという事実は全く予
想外の成果といえる。When a nitro compound or glycidol is added to Freon 113 or a mixed solvent thereof, the stabilizing effect is small; or it does not exhibit any stabilizing effect at all, whereas simply adding them in combination results in a significant stabilizing effect. The fact that a stabilizing effect was observed is a completely unexpected result.
本発明においてフロン113及びその混合溶剤に添加す
る該安定剤の割合は、フロン113及びその混合溶剤に
対してニトロ化合物がo、oi〜3.0重量%、好まし
くは0.1〜2.0重量%、グリシドールが0.001
〜0.5重量%、好ましくは0.01〜0.2重量%が
それぞれ適している。In the present invention, the proportion of the stabilizer added to Freon 113 and its mixed solvent is such that the nitro compound is o, oi to 3.0% by weight, preferably 0.1 to 2.0% by weight. Weight%, glycidol 0.001
~0.5% by weight, preferably 0.01-0.2% by weight, respectively, are suitable.
安定剤の添加量を前記の範囲より少なくした場合は安定
化効果は認められなくなり、また前記の範囲より多くし
た場合はかえってフロン113及びその混合溶剤の特性
を損なうためいずれも好ましくない。If the amount of the stabilizer added is less than the above range, no stabilizing effect will be observed, and if it is more than the above range, the properties of Freon 113 and its mixed solvent will be adversely affected, which is not preferable.
以下、本発明を実施例より更に具体的に説明するが、本
発明はこれらの実施例に限定されるものではない。EXAMPLES Hereinafter, the present invention will be explained in more detail with reference to Examples, but the present invention is not limited to these Examples.
実施例 1〜9
ガラス製容器(内径45間、深さ90順)に表1に示さ
れるニトロ化合物及びグリシドールを各各組合せて添加
したフロン113又はその混合溶剤30gに0.3重量
%相当量の水(フロン113とインプロパツールの混合
溶剤の場合は1.5重量%)を加え、十分層いた金属片
(40mrIL×20關×2間)を投入後、密栓し、常
温で15日間の浸漬試験を行なった。Examples 1 to 9 Each combination of the nitro compound and glycidol shown in Table 1 was added to a glass container (inner diameter: 45mm, depth: 90mm) in an amount equivalent to 0.3% by weight to 30g of Freon 113 or its mixed solvent. of water (1.5% by weight in the case of a mixed solvent of Freon 113 and Improper Tool), put in a sufficient layer of metal pieces (40 mr IL x 20 m x 2 spaces), then seal tightly and leave at room temperature for 15 days. An immersion test was conducted.
以上の結果を第1表に示した。比較例 1〜8
安定剤を添加しないフロン113又はその混合溶剤に0
.3重量%相当量の水(フロン113とイソプロパツー
ルの混合溶剤の場合は1.5重量%)を加えて実施例1
〜9と同様の方法で試験した場合の結果を第2表の比較
例1,2,6,7.8に示した。The above results are shown in Table 1. Comparative Examples 1 to 8 0 to Freon 113 or its mixed solvent without adding stabilizer
.. Example 1 by adding water equivalent to 3% by weight (1.5% by weight in the case of a mixed solvent of Freon 113 and isopropanol)
Comparative Examples 1, 2, 6, and 7.8 in Table 2 show the results of tests conducted in the same manner as in Examples 1 to 9.
また、安定剤としてニトロ化合物又はグリシドール−ル
を各々単独に添加したフロン113又はその混合溶剤及
びニトロ化合物とアルキレンオキサイドを組合せて添加
したフロン113又はその混合溶剤のそれぞれに0.3
重量%相当量の水を加えて試験した場合の結果を第2表
の比較例3,4.5に示した。In addition, 0.3% was added to each of Freon 113 or a mixed solvent thereof to which a nitro compound or glycidol was added as a stabilizer, and Freon 113 or a mixed solvent thereof to which a nitro compound and alkylene oxide were added in combination.
Comparative Examples 3 and 4.5 in Table 2 show the results of a test in which water was added in an amount equivalent to % by weight.
なおアルキレンオキサイドとしてはブチレンオキサイド
を添加した。Note that butylene oxide was added as the alkylene oxide.
実施例 10〜19
還流冷却器を取り付けたガラス製ナスフラスコ(内容積
300mA’)にニトロ化合物及びグリシドールを各々
組合せて、添加したフロン113又はその混合溶剤20
0CCと0.3重量%相当量の水(フロン113とイン
プロパツールの混合溶剤の場合は1.5重量%)を入れ
、十分層いた金属片(40mm×20mrnX 2mm
)を気相部、液相部にそれぞれ設置し、約55℃で48
時間加熱還流した。Examples 10 to 19 A combination of a nitro compound and glycidol was added to a glass eggplant flask (inner volume 300 mA') equipped with a reflux condenser, and Freon 113 or its mixed solvent 20 was added.
Add water equivalent to 0CC and 0.3% by weight (1.5% by weight in the case of a mixed solvent of Freon 113 and Improper Tool), and place a sufficient layer of metal pieces (40 mm x 20 mrn x 2 mm).
) were installed in the gas phase and liquid phase, respectively, and heated to 48℃ at about 55℃.
The mixture was heated to reflux for an hour.
以上の結果を第3表に示した。The above results are shown in Table 3.
比較例 9〜16
安定剤を添加しないフロン113又はその混合溶剤に0
.3重量%相当量の水(フロン113とイソプロパツー
ルの混合溶剤の場合は1.5重量%)を加えて実施例1
0〜19と同様の方法で試験した結果を第4表の比較例
9,10,14,15゜16に示した。Comparative Examples 9 to 16 0 to Freon 113 or its mixed solvent without adding stabilizer
.. Example 1 by adding water equivalent to 3% by weight (1.5% by weight in the case of a mixed solvent of Freon 113 and isopropanol)
Comparative Examples 9, 10, 14, 15゜16 in Table 4 show the results of tests conducted in the same manner as those for Nos. 0 to 19.
また、安定剤としてニトロ化合物又はグリシドールを各
々単独に添加したフロン113及びその混合溶剤及びニ
トロ化合物とアルキレンオキサイドを組合せて添加した
フロン113及びその混合溶剤のそれぞれに0.3重量
%相当量の水を加えて試験した場合の結果を第4表の比
較例10.11に示した。In addition, an amount of water equivalent to 0.3% by weight was added to each of Freon 113 and its mixed solvent to which a nitro compound or glycidol was added individually as a stabilizer, and Freon 113 and its mixed solvent to which a nitro compound and alkylene oxide were added in combination. The results were shown in Comparative Examples 10 and 11 in Table 4.
なおアルキレンオキサイドとしてはブチレンオキサイド
を添加した。Note that butylene oxide was added as the alkylene oxide.
Claims (1)
エタン系溶剤にニトロ化合物とグリシドールとを添加す
ることを特徴とする1 、 1 、2−トリクロロ−1
22−1リフルオロエタン系溶剤の安定化法。11,1.2-) Lichloro-1.2.1,1,2-Trichloro-1 characterized by adding a nitro compound and glycidol to a 2-trifluoroethane solvent
22-1 Method for stabilizing refluoroethane solvent.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14710878A JPS5851995B2 (en) | 1978-11-30 | 1978-11-30 | Stabilization method for 1,1,2↓-trichloro↓-1,2,2↓-trifluoroethane solvent |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14710878A JPS5851995B2 (en) | 1978-11-30 | 1978-11-30 | Stabilization method for 1,1,2↓-trichloro↓-1,2,2↓-trifluoroethane solvent |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5573797A JPS5573797A (en) | 1980-06-03 |
| JPS5851995B2 true JPS5851995B2 (en) | 1983-11-19 |
Family
ID=15422689
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14710878A Expired JPS5851995B2 (en) | 1978-11-30 | 1978-11-30 | Stabilization method for 1,1,2↓-trichloro↓-1,2,2↓-trifluoroethane solvent |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5851995B2 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5936199A (en) * | 1982-08-24 | 1984-02-28 | 東亞合成株式会社 | Dry cleaning solvent composition |
-
1978
- 1978-11-30 JP JP14710878A patent/JPS5851995B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5573797A (en) | 1980-06-03 |
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