JPS6367519B2 - - Google Patents
Info
- Publication number
- JPS6367519B2 JPS6367519B2 JP11400981A JP11400981A JPS6367519B2 JP S6367519 B2 JPS6367519 B2 JP S6367519B2 JP 11400981 A JP11400981 A JP 11400981A JP 11400981 A JP11400981 A JP 11400981A JP S6367519 B2 JPS6367519 B2 JP S6367519B2
- Authority
- JP
- Japan
- Prior art keywords
- oil
- acid
- fluorocarbons
- oils
- fluorocarbon
- 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
- -1 polyol ester Chemical class 0.000 claims description 15
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 claims description 11
- 229920005862 polyol Polymers 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 3
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 239000003921 oil Substances 0.000 description 34
- 239000000126 substance Substances 0.000 description 11
- 239000002199 base oil Substances 0.000 description 9
- AFVFQIVMOAPDHO-UHFFFAOYSA-N methanesulfonic acid Substances CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 229940098779 methanesulfonic acid Drugs 0.000 description 5
- 238000005057 refrigeration Methods 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 150000004996 alkyl benzenes Chemical class 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- MHPUGCYGQWGLJL-UHFFFAOYSA-N dimethyl pentanoic acid Natural products CC(C)CCCC(O)=O MHPUGCYGQWGLJL-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000010721 machine oil Substances 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- MBABOKRGFJTBAE-UHFFFAOYSA-N methyl methanesulfonate Chemical compound COS(C)(=O)=O MBABOKRGFJTBAE-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 150000004671 saturated fatty acids Chemical class 0.000 description 3
- QJRRBVNPIKYRQJ-UHFFFAOYSA-N 10-methylundecanoic acid Chemical compound CC(C)CCCCCCCCC(O)=O QJRRBVNPIKYRQJ-UHFFFAOYSA-N 0.000 description 2
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 description 2
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- 239000005297 pyrex Substances 0.000 description 2
- 230000000087 stabilizing effect Effects 0.000 description 2
- 238000005979 thermal decomposition reaction Methods 0.000 description 2
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 1
- ZONJATNKKGGVSU-UHFFFAOYSA-N 14-methylpentadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCC(O)=O ZONJATNKKGGVSU-UHFFFAOYSA-N 0.000 description 1
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- HFWHTGSLDKKCMD-UHFFFAOYSA-N 2,2-bis(octanoyloxymethyl)butyl octanoate Chemical compound CCCCCCCC(=O)OCC(CC)(COC(=O)CCCCCCC)COC(=O)CCCCCCC HFWHTGSLDKKCMD-UHFFFAOYSA-N 0.000 description 1
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 1
- UJZKCQGCOVJQEM-UHFFFAOYSA-N 4-methylpentane-1-sulfonic acid Chemical compound CC(C)CCCS(O)(=O)=O UJZKCQGCOVJQEM-UHFFFAOYSA-N 0.000 description 1
- OEOIWYCWCDBOPA-UHFFFAOYSA-N 6-methyl-heptanoic acid Chemical compound CC(C)CCCCC(O)=O OEOIWYCWCDBOPA-UHFFFAOYSA-N 0.000 description 1
- HUFKTRBTUGKAJF-UHFFFAOYSA-N 7-methyloctane-1-sulfonic acid Chemical compound CC(C)CCCCCCS(O)(=O)=O HUFKTRBTUGKAJF-UHFFFAOYSA-N 0.000 description 1
- XZOYHFBNQHPJRQ-UHFFFAOYSA-N 7-methyloctanoic acid Chemical compound CC(C)CCCCCC(O)=O XZOYHFBNQHPJRQ-UHFFFAOYSA-N 0.000 description 1
- OAOABCKPVCUNKO-UHFFFAOYSA-N 8-methyl Nonanoic acid Chemical compound CC(C)CCCCCCC(O)=O OAOABCKPVCUNKO-UHFFFAOYSA-N 0.000 description 1
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 1
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- PLUBXMRUUVWRLT-UHFFFAOYSA-N Ethyl methanesulfonate Chemical compound CCOS(C)(=O)=O PLUBXMRUUVWRLT-UHFFFAOYSA-N 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 239000005643 Pelargonic acid Substances 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- DRRMRHKHTQRWMB-UHFFFAOYSA-N [3-(2-ethylhexanoyloxy)-2,2-bis(2-ethylhexanoyloxymethyl)propyl] 2-ethylhexanoate Chemical compound CCCCC(CC)C(=O)OCC(COC(=O)C(CC)CCCC)(COC(=O)C(CC)CCCC)COC(=O)C(CC)CCCC DRRMRHKHTQRWMB-UHFFFAOYSA-N 0.000 description 1
- 239000000370 acceptor Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 238000004378 air conditioning Methods 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- LFLBHTZRLVHUQC-UHFFFAOYSA-N butyl methanesulfonate Chemical compound CCCCOS(C)(=O)=O LFLBHTZRLVHUQC-UHFFFAOYSA-N 0.000 description 1
- 239000010725 compressor oil 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
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- KOGOBKOHQTZGIS-UHFFFAOYSA-N cyclohexyl methanesulfonate Chemical compound CS(=O)(=O)OC1CCCCC1 KOGOBKOHQTZGIS-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- AGHOUEDRPDQZBI-UHFFFAOYSA-N decyl methanesulfonate Chemical compound CCCCCCCCCCOS(C)(=O)=O AGHOUEDRPDQZBI-UHFFFAOYSA-N 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 239000010696 ester oil Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- ANNNGOUEZBONHD-UHFFFAOYSA-N ethyl phenylmethanesulfonate Chemical compound CCOS(=O)(=O)CC1=CC=CC=C1 ANNNGOUEZBONHD-UHFFFAOYSA-N 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- FESYLDKBOOCXRD-UHFFFAOYSA-N hexadecyl methanesulfonate Chemical compound CCCCCCCCCCCCCCCCOS(C)(=O)=O FESYLDKBOOCXRD-UHFFFAOYSA-N 0.000 description 1
- FYAQQULBLMNGAH-UHFFFAOYSA-N hexane-1-sulfonic acid Chemical compound CCCCCCS(O)(=O)=O FYAQQULBLMNGAH-UHFFFAOYSA-N 0.000 description 1
- URIRDRHUUFRHAS-UHFFFAOYSA-N hexyl methanesulfonate Chemical compound CCCCCCOS(C)(=O)=O URIRDRHUUFRHAS-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- FGKJLKRYENPLQH-UHFFFAOYSA-N isocaproic acid Chemical compound CC(C)CCC(O)=O FGKJLKRYENPLQH-UHFFFAOYSA-N 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- MNRGFUBMMILKAL-UHFFFAOYSA-N methyl phenylmethanesulfonate Chemical compound COS(=O)(=O)CC1=CC=CC=C1 MNRGFUBMMILKAL-UHFFFAOYSA-N 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 231100000989 no adverse effect Toxicity 0.000 description 1
- VEWQLGOULVHVSR-UHFFFAOYSA-N nonyl methanesulfonate Chemical compound CCCCCCCCCOS(C)(=O)=O VEWQLGOULVHVSR-UHFFFAOYSA-N 0.000 description 1
- AGOZHKWJCGWDRV-UHFFFAOYSA-N nonyl phenylmethanesulfonate Chemical compound CCCCCCCCCOS(=O)(=O)CC1=CC=CC=C1 AGOZHKWJCGWDRV-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- KNPLQZXBTKKRAJ-UHFFFAOYSA-N octadecyl methanesulfonate Chemical compound CCCCCCCCCCCCCCCCCCOS(C)(=O)=O KNPLQZXBTKKRAJ-UHFFFAOYSA-N 0.000 description 1
- 229960002446 octanoic acid Drugs 0.000 description 1
- GRJPLADOIKKOGS-UHFFFAOYSA-N octyl methanesulfonate Chemical compound CCCCCCCCOS(C)(=O)=O GRJPLADOIKKOGS-UHFFFAOYSA-N 0.000 description 1
- RJMTUAMLNHKEJL-UHFFFAOYSA-N octyl phenylmethanesulfonate Chemical compound CCCCCCCCOS(=O)(=O)CC1=CC=CC=C1 RJMTUAMLNHKEJL-UHFFFAOYSA-N 0.000 description 1
- TWBKZBJAVASNII-UHFFFAOYSA-N pentadecane-1-sulfonic acid Chemical compound CCCCCCCCCCCCCCCS(O)(=O)=O TWBKZBJAVASNII-UHFFFAOYSA-N 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- WXVUCMFEGJUVTN-UHFFFAOYSA-N phenyl methanesulfonate Chemical compound CS(=O)(=O)OC1=CC=CC=C1 WXVUCMFEGJUVTN-UHFFFAOYSA-N 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- SWWHCQCMVCPLEQ-UHFFFAOYSA-N propan-2-yl methanesulfonate Chemical compound CC(C)OS(C)(=O)=O SWWHCQCMVCPLEQ-UHFFFAOYSA-N 0.000 description 1
- DKORSYDQYFVQNS-UHFFFAOYSA-N propyl methanesulfonate Chemical compound CCCOS(C)(=O)=O DKORSYDQYFVQNS-UHFFFAOYSA-N 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 239000006076 specific stabilizer Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 125000005472 straight-chain saturated fatty acid group Chemical group 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- GTSMGKYOGFOSAR-UHFFFAOYSA-N tridecane-1-sulfonic acid Chemical compound CCCCCCCCCCCCCS(O)(=O)=O GTSMGKYOGFOSAR-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Landscapes
- Lubricants (AREA)
Description
この発明はネオペンチル構造を有するポリオー
ル（以下、単にネオペンチル系ポリオールと称す
る）のエステルを基油とした耐フロン性油に関す
る。
近年、冷凍、冷戻工業、産業機器の高度化に伴
なう冷却、あるいは廃エネルギーの再利用など各
種の分野でフロンの利用が計られている。これら
の具体例としては、冷凍機、冷房機器をはじめ、
変圧機、整流器などの絶縁油の冷却、油の難燃
化、フロンタービンなどがある。こうしたフロン
を使用する機器においては、油とフロンとの反
応、あるいはフロンの熱分解によつて塩化水素を
生成し、これによつて装置の金属部分が腐食した
り、油の劣化が促進されるなどの問題がある。
この発明の目的は、フロンの共存下に使用して
も化学的に安定であり、つまりフロン共存下で高
温にさらされても油の分解がおこりにくく、しか
もフロンに対してもほとんど悪影響をおよぼさな
いいわゆる耐フロン性にすぐれた油を提供するこ
とにある。
ところで、従来、冷凍機油としては、ナフテン
系鉱油やアルキルベンゼン系油が一般に使用され
てきたが、これらの油では高温における化学的安
定性が不十分であつた。また、耐フロン性油とし
て、多価アルコールエステルないし二塩基性酸エ
ステルを基油とし、これに安定剤としてホスフア
イトやチオホスフアイトを添加したものが提案さ
れているが、熱安定性の面でなお満足できるもの
とはいえなかつた。
この発明者らは、上記の観点から鋭意検討した
結果、特定の基油に対して特定の安定剤を含ませ
たものが、従来にない化学的安定性を有し、耐フ
ロン性にすぐれたものとなることを見い出し、こ
の発明を完成するに至つたものである。
すなわち、この発明は、ネオペンチル系ポリオ
ールのエステル100重量部に、つぎの一般式；
（式中、Ｒはアルキル基、シクロアルキル基、フ
エニル基またはアルキルフエニル基である）
で表わされるメタンスルホン酸エステルを0.005
重量部以上含ませたことを特徴とする耐フロン性
油に係るものである。
この発明において基油として用いられるネオペ
ンチル系ポリオールのエステルは、一般にネオペ
ンチル系ポリオールおよび飽和脂肪酸あるいはこ
れらの低級アルキルエステルの如き誘導体を、そ
れぞれ１種または２種以上使用し、通常のエステ
ル化反応やエステル交換反応を行なわせることに
よつて得られるものであり、そのエステル化物の
水酸基価は０に近いほど望ましい。
上記に用いるネオペンチル系ポリオールとして
は、ネオペンチルグリコール、トリメチロールエ
タン、トリメチロールプロパン、ペンタエリスリ
トール、ジペンタエリスリトールなどが挙げられ
る。飽和脂肪酸は直鎖または分枝鎖の天然脂肪酸
ないし合成脂肪酸をいずれも適用できるが、その
炭素数は６〜18であるのが好適である。
具体的には、天然油脂から得られる天然脂肪酸
や合成脂肪酸のうち炭素数６〜18の直鎖飽和脂肪
酸として、カプロン酸、エナント酸、カプリル
酸、ペラルゴン酸、カプリン酸、ラウリン酸、ミ
リスチン酸、パルミチン酸、ステアリン酸などが
あり、また炭素数６〜18の合成分枝鎖飽和脂肪酸
として、イソヘキサン酸、イソヘプタン酸、イソ
オクタン酸、２−エチルヘキサン酸、イソノナン
酸、イソカプリン酸、イソラウリン酸、イソミリ
スチン酸、イソパルミチン酸、イソステアリン酸
などがある。
このような基油に対して安定剤として添加する
メタンスルホン酸エステルは、前記の一般式で表
わされるものであるが、一般式中のＲがアルキル
基またはアルキルフエニル基の場合、各アルキル
基の炭素数は１〜18であるのが好適であり、炭素
数があまりに多くなりすぎると基油に対する溶解
性が低下してくるから好ましくない。また、シク
ロアルキル基の代表例はシクロヘキシル基である
が、構造的安定なものであれば他のシクロアルキ
ル基であつてもよい。
上記メタンスルホン酸エステルの代表例を示す
と、たとえばメチルメタンスルフオネート、エチ
ルメタンスルフオネート、プロピルメタンスルフ
オネート、イソプロピルメタンスルフオネート、
ブチルメタンスルフオネート、アミルメタンスル
フオネート、イソアミルメタンスルフオネート、
ヘキシルメタンスルフオネート、シクロヘキシル
メタンスルフオネート、オクチルメタンスルフオ
ネート、イソオクチルメタンスルフオネート、ノ
ニルメタンスルフオネート、デシルメタンスルフ
オネート、ラウリルメタンスルフオネート、ミリ
スチルメタンスルフオネート、セチルメタンスル
フオネート、ステアリルメタンスルフオネート、
フエニルメタンスルフオネート、メチルフエニル
メタンスルフオネート、エチルフエニルメタンス
ルフオネート、オクチルフエニルメタンスルフオ
ネート、ノニルフエニルメタンスルフオネートな
どがある。
メタンスルホン酸エステルの使用量は、ネオペ
ンチル系ポリオールのエステルからなる基油100
重量部に対して、0.005重量部以上とすることが
必要で、上記より少なくなると高温におけるすぐ
れた化学的安定性が得られない。使用量が多くな
るにしたがつて化学的安定性は向上してくるが、
ある量を越えるとそれ以上使用しても効果が認め
られなくなり、さらに過剰使用は化学的安定性を
却つて損なう結果となるから、一般には30重量部
以下、とくに好適には５重量部以下とするのがよ
い。
この発明においてメタンスルホン酸エステルに
よる熱安定性向上効果がいかなる理由に基づくも
のであるかは必らずしも明らかではない。上記の
エステルは、油とフロンとの反応あるいはフロン
の熱分解によつて生ずる塩化水素の受容体の形成
を促進し、安定化させる機能を有しているものと
思われるが、他の基油、たとえばナフテン系鉱油
やアルキルベンゼン系油などに上記エステルを添
加しても、安定性向上効果はほとんど認められな
いことから、ネオペンチル系ポリオールのエステ
ルと併用されることによつて、その相乗的作用に
より、前記機能を顕著に発揮するに至つたものと
考えられる。
この発明の耐フロン性油は、本質的にネオペン
チル系ポリオールのエステルとメタンスルホン酸
エステルとからなるものであるが、必要ならこれ
ら成分に公知の添加剤を配合してもよく、またホ
スフアイトやチオホスフアイトの如き公知の安定
剤をこの発明の効果を失なわない使用割合で添加
することもできる。
以上詳細したとおり、この発明の耐フロン性油
は、高温での化学的安定性にすぐれ、フロンとほ
とんど反応せず、しかもフロンの安定化効果もあ
るので、フロン直接冷却方式を採用した絶縁油、
軸受油として、またフロン圧縮機油、冷凍機油な
どのフロンの存在下で使用される機器用の潤滑油
などとして広く利用できる。
つぎにこの発明を実施例により説明する。
実施例 １
トリメチロールプロパントリカプリレートにメ
タンスルホン酸エステル７種類を添加配合し、高
温における化学的安定性を評価するためにシール
ドチユーブテストを行つた。
すなわち、肉厚パイレツクス試験管に試料油
（1.5ml）とフロンＲ−113（1.5ml）を入れて減圧
下に封管した。これを220℃の熱風乾燥器に入れ
て加熱試験を30日間行つた。試験後の試料油とフ
ロンの混合物について塩素イオン濃度を測定し
た。結果を第１表に示す。
表より、安定剤のメタンスルホン酸エステルは
基油100重量部に対する添加配合率が0.005重量部
以上で効果を発揮することがわかる。
This invention relates to a fluorocarbon-resistant oil using an ester of a polyol having a neopentyl structure (hereinafter simply referred to as a neopentyl polyol) as a base oil. In recent years, fluorocarbons have been used in a variety of fields, including refrigeration, refrigeration, cooling as industrial equipment becomes more sophisticated, and the reuse of waste energy. Specific examples of these include refrigerators, air conditioning equipment,
Examples include cooling insulating oil for transformers and rectifiers, making oil flame-retardant, and fluorocarbon turbines. In equipment that uses such fluorocarbons, hydrogen chloride is produced by the reaction between oil and fluorocarbons or by the thermal decomposition of fluorocarbons, which corrodes the metal parts of the equipment and accelerates the deterioration of the oil. There are problems such as. The purpose of this invention is to ensure that the oil is chemically stable even when used in the coexistence of fluorocarbons.In other words, even when exposed to high temperatures in the coexistence of fluorocarbons, oil decomposition is unlikely to occur, and moreover, it has almost no adverse effect on fluorocarbons. The object of the present invention is to provide an oil with excellent so-called fluorocarbon resistance that does not cause pollution. By the way, naphthenic mineral oils and alkylbenzene oils have conventionally been generally used as refrigerating machine oils, but these oils have insufficient chemical stability at high temperatures. In addition, as CFC-resistant oils, oils in which polyhydric alcohol esters or dibasic acid esters are used as base oils and phosphites or thiophosphites are added as stabilizers have been proposed, but they are still unsatisfactory in terms of thermal stability. I couldn't say it was possible. As a result of extensive research from the above perspective, the inventors found that a specific base oil containing a specific stabilizer has unprecedented chemical stability and excellent CFC resistance. This led to the completion of this invention. That is, in this invention, 100 parts by weight of ester of neopentyl polyol is added with the following general formula; (wherein R is an alkyl group, a cycloalkyl group, a phenyl group or an alkylphenyl group)
This relates to a fluorocarbon-resistant oil characterized in that it contains at least part by weight. The neopentyl polyol ester used as the base oil in this invention is generally made by using one or more of neopentyl polyol and saturated fatty acid or their derivatives such as lower alkyl esters, and carrying out a normal esterification reaction or esterification. It is obtained by carrying out an exchange reaction, and it is desirable that the hydroxyl value of the esterified product be as close to 0 as possible. Examples of the neopentyl polyol used above include neopentyl glycol, trimethylolethane, trimethylolpropane, pentaerythritol, dipentaerythritol, and the like. As the saturated fatty acid, any linear or branched natural fatty acid or synthetic fatty acid can be used, but it is preferable that the number of carbon atoms is 6 to 18. Specifically, among natural fatty acids and synthetic fatty acids obtained from natural fats and oils, straight chain saturated fatty acids with 6 to 18 carbon atoms include caproic acid, enanthic acid, caprylic acid, pelargonic acid, capric acid, lauric acid, myristic acid, Palmitic acid, stearic acid, etc., as well as synthetic branched chain saturated fatty acids with 6 to 18 carbon atoms, such as isohexanoic acid, isoheptanoic acid, isooctanoic acid, 2-ethylhexanoic acid, isononanoic acid, isocapric acid, isolauric acid, and isomyristine. acids, isopalmitic acid, isostearic acid, etc. The methanesulfonic acid ester added as a stabilizer to such a base oil is represented by the general formula above, and when R in the general formula is an alkyl group or an alkylphenyl group, each alkyl group It is preferable that the number of carbon atoms is 1 to 18, and if the number of carbon atoms is too large, the solubility in the base oil will decrease, which is not preferable. Further, a typical example of the cycloalkyl group is a cyclohexyl group, but other cycloalkyl groups may be used as long as they are structurally stable. Representative examples of the above methanesulfonate esters include methylmethanesulfonate, ethylmethanesulfonate, propylmethanesulfonate, isopropylmethanesulfonate,
Butylmethanesulfonate, amylmethanesulfonate, isoamylmethanesulfonate,
Hexylmethanesulfonate, cyclohexylmethanesulfonate, octylmethanesulfonate, isooctylmethanesulfonate, nonylmethanesulfonate, decylmethanesulfonate, laurylmethanesulfonate, myristylmethanesulfonate, cetyl methanesulfonate, stearyl methanesulfonate,
Examples include phenyl methanesulfonate, methyl phenyl methanesulfonate, ethyl phenyl methanesulfonate, octylphenyl methanesulfonate, and nonylphenyl methanesulfonate. The amount of methanesulfonic acid ester used is 100% of the base oil made of neopentyl polyol ester.
It is necessary to set the amount to 0.005 parts by weight or more, and if it is less than the above, excellent chemical stability at high temperatures will not be obtained. Chemical stability improves as the amount used increases, but
If it exceeds a certain amount, no effect will be observed even if it is used more than that, and furthermore, excessive use will actually impair chemical stability, so it is generally 30 parts by weight or less, particularly preferably 5 parts by weight or less. It is better to do so. In this invention, it is not necessarily clear what the reason is for the thermal stability improving effect of methanesulfonic acid ester. The above esters seem to have the function of promoting and stabilizing the formation of hydrogen chloride acceptors generated by the reaction between oil and fluorocarbons or the thermal decomposition of fluorocarbons, but other base oils For example, even if the above-mentioned ester is added to naphthenic mineral oil or alkylbenzene oil, there is almost no stability improvement effect. , it is thought that the above function has been achieved significantly. The fluorocarbon-resistant oil of this invention essentially consists of neopentyl polyol ester and methanesulfonic acid ester, but if necessary, known additives may be added to these components, and phosphite or thiophosphite may also be added. It is also possible to add known stabilizers such as the following in proportions that do not impair the effects of this invention. As detailed above, the fluorocarbon-resistant oil of this invention has excellent chemical stability at high temperatures, hardly reacts with fluorocarbons, and also has a stabilizing effect on fluorocarbons. ,
It can be widely used as a bearing oil and as a lubricating oil for equipment used in the presence of fluorocarbons, such as fluorocarbon compressor oil and refrigeration oil. Next, this invention will be explained by examples. Example 1 Seven types of methanesulfonic acid esters were added to trimethylolpropane tricaprylate, and a shield tube test was conducted to evaluate the chemical stability at high temperatures. That is, sample oil (1.5 ml) and Freon R-113 (1.5 ml) were placed in a thick-walled Pyrex test tube, and the tube was sealed under reduced pressure. This was placed in a hot air dryer at 220°C and a heating test was conducted for 30 days. The chloride ion concentration was measured for the sample oil and Freon mixture after the test. The results are shown in Table 1. From the table, it can be seen that the stabilizer methanesulfonic acid ester exhibits its effect when the addition ratio is 0.005 parts by weight or more based on 100 parts by weight of the base oil.
【表】
実施例 ２
ペンタエリスリトールテトラ２−エチルヘキサ
ノエートにメタンスルホン酸エステル６種類を添
加配合した本発明品と耐フロン性向上剤として知
られている亜リン酸エステルを前記エステル油に
添加配合した従来品および市販の冷凍機油２種類
と熱媒体油１種類について、高温における化学的
安定性を評価するためにシールドチユーブテスト
を行つた。
すなわち、肉厚パイレツクス試験管に試料油
（1.5ml）と冷媒〔フロンＲ−12およびＲ−22〕
（1.5ml）と鉄片（１×４×40mm）を入れて減圧下
に封管した。これを200℃の熱風乾燥器に入れて
加熱試験を30日間行つた。試験後の試料油とフロ
ン混合物について、色相、金属腐食の有無、塩素
イオン濃度を測定した。結果を第２表に示す。
本発明品は従来品、市販の冷凍機油や熱媒体油
と比較して化学的安定性に非常にすぐれているこ
とがわかる。[Table] Example 2 A product of the present invention in which six types of methanesulfonic acid esters are added to pentaerythritol tetra-2-ethylhexanoate, and a phosphorous acid ester known as a fluorocarbon resistance improver is added to the ester oil. A sealed tube test was conducted to evaluate the chemical stability at high temperatures for the conventional and commercially available two types of refrigeration oil and one type of heat transfer oil. That is, sample oil (1.5 ml) and refrigerant [Freon R-12 and R-22] are placed in a thick-walled Pyrex test tube.
(1.5 ml) and an iron piece (1 x 4 x 40 mm) were placed in the tube and sealed under reduced pressure. This was placed in a hot air dryer at 200°C and a heating test was conducted for 30 days. After the test, the hue, presence or absence of metal corrosion, and chloride ion concentration were measured for the sample oil and fluorocarbon mixture. The results are shown in Table 2. It can be seen that the product of the present invention has extremely superior chemical stability compared to conventional products and commercially available refrigerating machine oils and heat transfer oils.
【表】
実施例 ３
ネオペンチルポリオールエステル９種類にそれ
ぞれメチルメタンスルフオネートを添加配合した
本発明品と、アルキルベンゼン油およびポリオレ
フイン油にメチルメタンスルフオネートを添加配
合した比較品および市販の冷凍機油２種類と熱媒
体油１種類について、高温における化学的安定性
を評価するためにシールドチユーブテストを行つ
た。
すなわち、肉厚パイレツクス試験管に試料油
（1.5ml）とフロンＲ−113（1.5ml）と金属片（１
×４×40mm）としてステンレス鋼SUS304および
銅を入れて減圧下に封管した。これを200℃の熱
風乾燥器に入れて加熱試験を30日間行つた。試験
後の試料油とフロン混合物について、塩素イオン
濃度を測定した。結果を第３表に示す。
本発明品は比較品、市販の冷凍機油や熱媒体油
と比較して化学的安定性に非常にすぐれているこ
とがわかる。[Table] Example 3 A product of the present invention in which methyl methanesulfonate is added to each of nine neopentyl polyol esters, a comparative product in which methyl methanesulfonate is added to alkylbenzene oil and polyolefin oil, and a commercially available refrigeration oil. A sealed tube test was conducted on the two types and one type of heat transfer oil to evaluate their chemical stability at high temperatures. That is, sample oil (1.5 ml), Freon R-113 (1.5 ml), and metal piece (1
x 4 x 40 mm), stainless steel SUS304 and copper were placed in the tube and the tube was sealed under reduced pressure. This was placed in a hot air dryer at 200°C and a heating test was conducted for 30 days. The chloride ion concentration was measured for the sample oil and fluorocarbon mixture after the test. The results are shown in Table 3. It can be seen that the product of the present invention has extremely superior chemical stability compared to comparative products and commercially available refrigerating machine oils and heat transfer oils.
【表】【table】
【表】【table】
Claims (1)
テル100重量部に、つぎの一般式； （式中、Ｒはアルキル基、シクロアルキル基、フ
エニル基またはアルキルフエニル基である） で表わされるメタンスルホン酸エステルを0.005
重量部以上含ませたことを特徴とする耐フロン性
油。[Claims] 1. 100 parts by weight of a polyol ester having a neopentyl structure is added with the following general formula; (wherein R is an alkyl group, a cycloalkyl group, a phenyl group or an alkylphenyl group)
A fluorocarbon-resistant oil characterized by containing more than part by weight.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11400981A JPS5815592A (en) | 1981-07-20 | 1981-07-20 | Flow-resistant oil |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11400981A JPS5815592A (en) | 1981-07-20 | 1981-07-20 | Flow-resistant oil |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5815592A JPS5815592A (en) | 1983-01-28 |
| JPS6367519B2 true JPS6367519B2 (en) | 1988-12-26 |
Family
ID=14626765
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11400981A Granted JPS5815592A (en) | 1981-07-20 | 1981-07-20 | Flow-resistant oil |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5815592A (en) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH066716B2 (en) * | 1985-01-26 | 1994-01-26 | 日本油脂株式会社 | Freon-resistant refrigeration oil |
| JPS62592A (en) * | 1985-06-27 | 1987-01-06 | Nippon Oil & Fats Co Ltd | Highly viscous oil for refrigerator |
| DE69020085T3 (en) * | 1989-04-25 | 2010-04-22 | The Lubrizol Corp., Wickliffe | CARBONIC ACID CONTAINING LIQUID COMPOSITIONS. |
| JP2801703B2 (en) * | 1989-09-01 | 1998-09-21 | 花王株式会社 | Refrigerating machine oil |
| JP2573111B2 (en) * | 1990-09-12 | 1997-01-22 | 花王 株式会社 | Composition for working fluid of refrigerator |
| JP2967574B2 (en) | 1990-11-16 | 1999-10-25 | 株式会社日立製作所 | Refrigeration equipment |
| BR9207136A (en) * | 1992-06-03 | 1995-08-29 | Henkel Corp | Refrigerant working fluid, and, process to operate a mechanical refrigerant system |
| US5853609A (en) * | 1993-03-10 | 1998-12-29 | Henkel Corporation | Polyol ester lubricants for hermetically sealed refrigerating compressors |
| US9562208B2 (en) * | 2014-07-02 | 2017-02-07 | Basf Se | Sulfonate esters to improve fluoropolymer seal compatibility of lubricant compositions |
-
1981
- 1981-07-20 JP JP11400981A patent/JPS5815592A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5815592A (en) | 1983-01-28 |
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