JPS6113447B2 - - Google Patents
Info
- Publication number
- JPS6113447B2 JPS6113447B2 JP52118601A JP11860177A JPS6113447B2 JP S6113447 B2 JPS6113447 B2 JP S6113447B2 JP 52118601 A JP52118601 A JP 52118601A JP 11860177 A JP11860177 A JP 11860177A JP S6113447 B2 JPS6113447 B2 JP S6113447B2
- Authority
- JP
- Japan
- Prior art keywords
- fluorocarbons
- alcoholic hydroxyl
- hydroxyl groups
- present
- stabilizer
- 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
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- 230000001476 alcoholic effect Effects 0.000 claims description 13
- FKIJMTKJEMUCQG-UHFFFAOYSA-N 1,2-dimethyl-3-prop-1-en-2-ylbenzene Chemical group CC(=C)C1=CC=CC(C)=C1C FKIJMTKJEMUCQG-UHFFFAOYSA-N 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 5
- 230000000087 stabilizing effect Effects 0.000 claims description 4
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 claims 2
- 230000006641 stabilisation Effects 0.000 claims 2
- 238000011105 stabilization Methods 0.000 claims 2
- 229920005862 polyol Polymers 0.000 description 13
- 239000003381 stabilizer Substances 0.000 description 13
- 150000003077 polyols Chemical class 0.000 description 10
- 229920002635 polyurethane Polymers 0.000 description 7
- 239000004814 polyurethane Substances 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 238000004040 coloring Methods 0.000 description 5
- 238000005187 foaming Methods 0.000 description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 4
- -1 amine polyol Chemical class 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- QIDIFDCCFHVZOR-UHFFFAOYSA-N 2,4-dimethyl-1-prop-1-en-2-ylbenzene Chemical group CC(=C)C1=CC=C(C)C=C1C QIDIFDCCFHVZOR-UHFFFAOYSA-N 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 2
- 238000002845 discoloration Methods 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- UGCSPKPEHQEOSR-UHFFFAOYSA-N 1,1,2,2-tetrachloro-1,2-difluoroethane Chemical compound FC(Cl)(Cl)C(F)(Cl)Cl UGCSPKPEHQEOSR-UHFFFAOYSA-N 0.000 description 1
- AJDIZQLSFPQPEY-UHFFFAOYSA-N 1,1,2-Trichlorotrifluoroethane Chemical compound FC(F)(Cl)C(F)(Cl)Cl AJDIZQLSFPQPEY-UHFFFAOYSA-N 0.000 description 1
- XSQYYLSXKMCPJQ-UHFFFAOYSA-N 1,2-dimethyl-4-prop-1-en-2-ylbenzene Chemical group CC(=C)C1=CC=C(C)C(C)=C1 XSQYYLSXKMCPJQ-UHFFFAOYSA-N 0.000 description 1
- 241001550224 Apha Species 0.000 description 1
- 239000004604 Blowing Agent Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 229920005830 Polyurethane Foam Polymers 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000003421 catalytic decomposition reaction Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 239000011496 polyurethane foam Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000012086 standard solution Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Polyurethanes Or Polyureas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
本発明はアルコール性水酸基に対するフロンの
安定化法に関するものである。
低級脂肪族弗素化塩素化炭化水素（以下、本発
明においてフロンと称する）はアルコール性水酸
基と容易に反応し分解を起すことが知られてい
る。塩素を含まない低級脂肪族弗素化炭化水素は
アルコール性水酸基に対して安定である。フロン
のアルコール性水酸基に対する反応は特に金属な
どの存在下に顕著である。この反応はたとえば
CCl3F＋CH3OH→CHCl2F＋HCHO＋HClの如き
もので、アルコールが酸化されてアルデヒドやケ
トンを生じ塩化水素を生成するものである。
一方、フロンはアルコール性水酸基と併用され
ることが多い。たとえばフロンをプロペラントと
したエアゾール製品にあつてはアルコールを溶剤
として使用することが多い。また、フロンを発泡
剤として使用するポリウレタン発泡にあたつては
フロンかポリウレタン原料であるポリオールと接
触する。その他、フロンがアルコール性水酸基と
接触する機会は少くない。
前記した如く、アルコール性水酸基と接触する
フロンは、その分解を防止するため安定剤を必要
とする。安定剤がない場合、たとえばエアゾール
製品にあつてはアルコールの酸化されたものによ
る臭気や塩化水素による容器の腐蝕や液の着色な
ど、ポリウレタン発泡にあつてはさらにアミン系
触媒の不活性化による発泡倍率の減少や製品の黄
褐色着色、粘度の上昇など製造に不都合をきた
し、製品の性質を劣化させる。このため、フロン
の安定剤は従来より種々研究されており、多くの
安定剤が知られている。しかしながら、従来の安
定剤は必ずしも満足しうる性質を有するものばか
りではなかつた。
例えば、ポリウレタン原料であるアミン系ポリ
オールとフロンとの混合物を貯蔵、輸送などする
場合、アルコール性水酸基とフロンとの接触分解
に基く着色やPH低下が充分に防止できない。後述
の加速試験などの結果からも明白な如く、従来の
各種安定剤では、着色程度が著しく、褐色、黒褐
色など著しい着色を招き、PH低下も大きい。かゝ
る着色やPH低下は、これを原料とした発泡ポリウ
レタン製品の汚染着色による外観、品位などの不
利と共に、発泡倍率の低下、更には製品の品質劣
化などの原因となる。
本発明者は、前記の如き欠点を解消する手段を
提供すべく、種々の研究検討を重ねた結果、ｐ−
イソプロペニル−ｏ−キシレンやｐ−イソプロペ
ニル−ｍ−キシレンを安定剤として使用すると苛
酷な条件下でもアルコール性水酸基とフロンの反
応を効果的に抑制し、著しい着色やPH低下を防止
し得ることを見出したものである。
かくして、本発明は、イソプロペニルキシレン
を含有せしめることを特徴とするアルコール性水
酸基に対するフロンの安定化法を新規に提供する
ものである。
本発明におけるイソプロペニルキシレンとして
は、ベンゼン核に２個のメチル基及び１個のイソ
プロペニル基が結合している公知乃至周知の化合
物が種々例示され得るが、通常は入手の容易性な
どから、ｐ−イソプロペニル−ｏ−キシレン又は
ｐ−イソプロペニル−ｍ−キシレンが好適であ
る。
本発明におけるフロンとは低級脂肪族弗素化塩
素化炭化水素のことであり、特に炭素数が１また
は２の弗素化塩素化アルカンである。アルコール
性水酸基に対して特に不安定なものは、その中で
も塩素の数が弗素の数と同数あるいはそれより大
なるもので、たとえばトリクロロフルオロメタ
ン、１・１・２−トリフルオロトリクロロエタ
ン、１・２−ジフルオロテトラクロルエタンなど
があり、これらに対して本発明の安定剤は効果が
大きい。
アルコール性水酸基としては、通常の脂肪族１
価あるいは多価アルコールの他、ポリウレタンの
原料となる種々のポリオール、その他のアルコー
ルの水酸基が含まれる。特に炭素数１〜４の１価
あるいは多価アルコール（たとえばメタノール、
エタノール、プロパノール、エチレングリコー
ル、プロピレングリコール、グリセリン等）、お
よびポリエーテルポリオール（ポリエチレングリ
コール、ポリプロピレングリコール等）、アミン
等の窒素含有基を有するポリオール、その他、特
にポリウレタン原料となるポリオールが含まれ
る。
ポリウレタン発泡体の製造の場合、発泡剤とし
てのフロンはポリオールと混合され、次いでイソ
シアネート類と混合される。通常、フロンとポリ
オールの混合物は長時間保存される場合が多い。
この場合、鉄の存在する場合が多く、フロンの不
安定化をきたすことがある。フロンの分解により
塩化水素が発生し、それがポリオール、特にアミ
ン系ポリオールと反応する。これにより、ウレタ
ンの発泡が阻害されるが、又たとえアミン系ポリ
オールが存在しない場合も触媒の阻害やその他の
不都合をきたす。本発明の安定剤は特にアミン系
ポリオールを含むウレタン発泡の場合有効であ
る。また、ポリオール中の不純物の影響が少いの
みならず、発泡体のセルがより均一になるという
効果も有している。
本発明における安定剤の添加量は特に限定され
ないが、好ましくはフロンに対して0.01重量％以
上、好ましくは0.05〜5.0重量％、特に0.2〜2.0重
量％が適当である。また、本発明の安定剤系にさ
らに他の成分を加えて２成分以上の安定剤系とし
て使用することも可能である。
以下、本発明を実施例により具体的に説明する
が、本発明はこれらの実施例のみに限定されるも
のではない。
実施例１〜４および比較例１〜11
Ｎ・Ｎ・N′・N′−テトラキス−２−ヒドロキ
シプロピルエチレンジアミン200重量部、トリエ
チレンジアミン２重量部、フロンＲ−11
（CCl3F）100重量部、下表に示される安定剤の所
定量を混合し、これを耐圧ガラス容器に入れ、鉄
板（10×50×２mm）をこの液に浸漬したままエア
ーバス中で温度を90℃に保持し、150時間加熱試
験を行う。フロンの分解が起ると塩化水素が生成
するので、PHを調べることによりその分解の程度
がわかり、また色度の上昇程度により安定化効果
が測定される。
前記加熱試験後に、試料液の色度をASTM−
D2108（1971）に準じて測定する。即ち、標準液
との対比により色度をApHAにて表示する。ま
た、試料液５ｇに、イソプロピルアルコール水溶
液（イソプロピルアルコール／純水の容積比10／
６）30mlを添加混合し、PHを測定する。これらの
結果を下表にまとめて示す。尚、加熱試験前のPH
は11.4、色度は10であつた。
The present invention relates to a method for stabilizing chlorofluorocarbons against alcoholic hydroxyl groups. It is known that lower aliphatic fluorinated chlorinated hydrocarbons (hereinafter referred to as fluorocarbons in the present invention) easily react with alcoholic hydroxyl groups and cause decomposition. Chlorine-free lower aliphatic fluorinated hydrocarbons are stable towards alcoholic hydroxyl groups. The reaction of chlorofluorocarbons to alcoholic hydroxyl groups is particularly noticeable in the presence of metals. For example, this reaction
CCl 3 F + CH 3 OH → CHCl 2 F + HCHO + HCl, where alcohol is oxidized to produce aldehydes and ketones and hydrogen chloride. On the other hand, Freon is often used in combination with an alcoholic hydroxyl group. For example, aerosol products that use fluorocarbons as a propellant often use alcohol as a solvent. Furthermore, in polyurethane foaming using fluorocarbons as a foaming agent, the fluorocarbons come into contact with polyol, which is a raw material for polyurethane. In addition, there are many opportunities for fluorocarbons to come into contact with alcoholic hydroxyl groups. As mentioned above, fluorocarbons that come into contact with alcoholic hydroxyl groups require a stabilizer to prevent their decomposition. If there is no stabilizer, for example, in the case of aerosol products, there may be odor caused by oxidized alcohol, corrosion of the container due to hydrogen chloride, coloring of the liquid, etc., and in the case of polyurethane foaming, foaming may occur due to the inactivation of amine catalysts. This causes inconveniences in manufacturing, such as a decrease in magnification, yellowish-brown coloring of the product, and an increase in viscosity, and deteriorates the properties of the product. For this reason, a variety of stabilizers for fluorocarbons have been studied in the past, and many stabilizers are known. However, conventional stabilizers do not always have satisfactory properties. For example, when storing or transporting a mixture of an amine polyol, which is a raw material for polyurethane, and fluorocarbons, it is not possible to sufficiently prevent discoloration and a decrease in pH due to catalytic decomposition of alcoholic hydroxyl groups and fluorocarbons. As is clear from the results of the accelerated tests described below, various conventional stabilizers cause significant coloring, such as brown or blackish brown, and also cause a large drop in pH. Such coloring and pH reduction cause disadvantages such as appearance and quality due to contamination and coloring of foamed polyurethane products made from this raw material, as well as a decrease in foaming ratio and further deterioration of product quality. In order to provide a means to eliminate the above-mentioned drawbacks, the present inventor has conducted various research studies and found that p-
When isopropenyl-o-xylene or p-isopropenyl-m-xylene is used as a stabilizer, the reaction between alcoholic hydroxyl groups and chlorofluorocarbons can be effectively suppressed even under severe conditions, and significant discoloration and pH drop can be prevented. This is what we discovered. Thus, the present invention provides a novel method for stabilizing chlorofluorocarbons against alcoholic hydroxyl groups, which is characterized by containing isopropenylxylene. As isopropenylxylene in the present invention, various known or well-known compounds in which two methyl groups and one isopropenyl group are bonded to a benzene nucleus can be exemplified, but usually, due to ease of acquisition, etc. Preference is given to p-isopropenyl-o-xylene or p-isopropenyl-m-xylene. In the present invention, fluorocarbons refer to lower aliphatic fluorinated chlorinated hydrocarbons, particularly fluorinated chlorinated alkanes having 1 or 2 carbon atoms. Particularly unstable to alcoholic hydroxyl groups are those in which the number of chlorine is equal to or greater than the number of fluorine, such as trichlorofluoromethane, 1,1,2-trifluorotrichloroethane, 1,2 -difluorotetrachloroethane, etc., and the stabilizer of the present invention is highly effective against these. As the alcoholic hydroxyl group, ordinary aliphatic 1
In addition to hydric or polyhydric alcohols, the hydroxyl groups of various polyols and other alcohols, which are raw materials for polyurethane, are included. In particular, monohydric or polyhydric alcohols having 1 to 4 carbon atoms (e.g. methanol,
ethanol, propanol, ethylene glycol, propylene glycol, glycerin, etc.), polyether polyols (polyethylene glycol, polypropylene glycol, etc.), polyols having nitrogen-containing groups such as amines, and others, especially polyols that serve as raw materials for polyurethane. In the production of polyurethane foams, freon as blowing agent is mixed with polyols and then with isocyanates. Usually, mixtures of fluorocarbons and polyols are often stored for long periods of time.
In this case, iron is often present, which may destabilize the fluorocarbon. The decomposition of fluorocarbons generates hydrogen chloride, which reacts with polyols, especially amine-based polyols. This inhibits foaming of the urethane, but also causes catalyst inhibition and other disadvantages even in the absence of the amine polyol. The stabilizer of the present invention is particularly effective in the case of urethane foam containing an amine polyol. Moreover, it not only has less influence from impurities in the polyol, but also has the effect of making the cells of the foam more uniform. The amount of stabilizer added in the present invention is not particularly limited, but it is preferably 0.01% by weight or more, preferably 0.05 to 5.0% by weight, particularly 0.2 to 2.0% by weight based on Freon. It is also possible to add other components to the stabilizer system of the present invention and use it as a stabilizer system containing two or more components. EXAMPLES Hereinafter, the present invention will be specifically explained with reference to Examples, but the present invention is not limited to these Examples. Examples 1 to 4 and Comparative Examples 1 to 11 200 parts by weight of N・N・N′・N′-tetrakis-2-hydroxypropylethylenediamine, 2 parts by weight of triethylenediamine, Freon R-11
Mix 100 parts by weight of (CCl 3 F) and the specified amount of the stabilizer shown in the table below, place this in a pressure-resistant glass container, and place a steel plate (10 x 50 x 2 mm) in an air bath while immersed in this liquid. The temperature is maintained at 90°C and a heating test is conducted for 150 hours. Hydrogen chloride is produced when fluorocarbons decompose, so the degree of decomposition can be determined by examining the pH, and the stabilizing effect can be measured by the degree of increase in chromaticity. After the heating test, the chromaticity of the sample solution was determined by ASTM-
Measure according to D2108 (1971). That is, the chromaticity is expressed in ApHA by comparison with a standard solution. In addition, add isopropyl alcohol aqueous solution (volume ratio of isopropyl alcohol/pure water 10/
6) Add 30ml, mix, and measure the pH. These results are summarized in the table below. In addition, PH before heating test
was 11.4, and the chromaticity was 10.
【表】【table】
Claims (1)
を特徴とするアルコール性水酸基に対するフロン
の安定化法。 ２ イソプロペニルキシレンとしてＰ−イソプロ
ペニル−Ｏ−キシレン又はｐ−イソプロペニル−
ｍ−キシレンを使用する特許請求の範囲第１項記
載の安定化法。 ３ フロン100重量部に対してイソプロペニルキ
シレン0.05〜5.0重量部を含有せしめる特許請求
の範囲第１項又は第２項記載の安定化法。[Claims] 1. A method for stabilizing chlorofluorocarbons against alcoholic hydroxyl groups, which comprises containing isopropenylxylene. 2 As isopropenylxylene, P-isopropenyl-O-xylene or p-isopropenyl-
Stabilization method according to claim 1, using m-xylene. 3. The stabilization method according to claim 1 or 2, wherein 0.05 to 5.0 parts by weight of isopropenylxylene is contained per 100 parts by weight of chlorofluorocarbons.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11860177A JPS5455503A (en) | 1977-10-04 | 1977-10-04 | Stabilization of flon |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11860177A JPS5455503A (en) | 1977-10-04 | 1977-10-04 | Stabilization of flon |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5455503A JPS5455503A (en) | 1979-05-02 |
| JPS6113447B2 true JPS6113447B2 (en) | 1986-04-14 |
Family
ID=14740600
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11860177A Granted JPS5455503A (en) | 1977-10-04 | 1977-10-04 | Stabilization of flon |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5455503A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2682377A1 (en) * | 1991-10-11 | 1993-04-16 | Atochem | STABILIZATION OF 1,1-DICHLORO-1-FLUOROETHANE. |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2029460C3 (en) * | 1970-06-09 | 1973-12-20 | Siemens Ag, 1000 Berlin U. 8000 Muenchen | Method for starting and synchronizing synchronous machines and arrangement for carrying out this method |
-
1977
- 1977-10-04 JP JP11860177A patent/JPS5455503A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5455503A (en) | 1979-05-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5137929A (en) | Additives which stabilize hydrohalocarbon blowing agent in polyurethane and polyisocyanurate foam formulations during polymerization | |
| US9695267B2 (en) | Foams and foamable compositions containing halogenated olefin blowing agents | |
| JP2017071777A (en) | Azeotrope-like compositions comprising 1-chloro-3,3,3-trifluoropropene | |
| JPH05179043A (en) | Blowing agent comprising fluorobutene and production of plastic foam | |
| JPH05239251A (en) | Blowing agent comprising fluoropropane and production of plastic foam | |
| US6086784A (en) | Premixes for the preparation of polyurethane or polyisocyanurate foams | |
| CZ289141B6 (en) | Process for preparing hard polyurethane foam materials | |
| US5395859A (en) | Catalysts which stabilize hydrohalocarbon blowing agent in polyisocyanurate foam formulations during polymerization | |
| US5688834A (en) | Catalysts which stabilize hydrohalocarbon blowing agent in polyurethane foam formulations | |
| WO1994011329A1 (en) | Hydrofluorohalocarbon decomposition inhibitor and method | |
| JPH05179042A (en) | Blowing agent comprising fluoropropene and production of plastic foam | |
| JPH09111031A (en) | Premix for producing polyurethane foam | |
| JPH05279653A (en) | Application of (rerfluoroalkyl) ethylene as blowing agent and/or heat insulation gas for polymer foam | |
| JPS6113447B2 (en) | ||
| US5366662A (en) | Stabilized compositions comprising hydrofluoroalkanes, premixtures intended for the preparation of polymeric foams and polymeric foams obtained by the use thereof | |
| US5169996A (en) | Stabilized 141b | |
| US5100925A (en) | Flexible polyurethane foam having reduced discoloration due to scorch during manufacture | |
| US6753356B2 (en) | Foaming compositions | |
| DE69930998T2 (en) | propellant | |
| JPH05179045A (en) | Foaming agent composed of fluorobutene and production of plastic foam | |
| JPH01128944A (en) | Method for stabilizing hydrogen-containing fluorocarbon | |
| JPH0125726B2 (en) | ||
| US5560869A (en) | Stabilized compositions comprising 1,1-dichloro-1-fluoroethane and use of these compositions as blowing agents in premixes intended for the preparation of polyurethane foams | |
| JP3247144B2 (en) | Method for inhibiting the degradation of hydrochlorofluorocarbons used as blowing agents in the production of foamed polyurethanes and polyisocyanurates | |
| USH2233H1 (en) | Catalysts which stabilize hydrofluorocarbon blowing agents in polyurethane foam compositions |