JP5546726B2 - 冷凍機油および冷凍機用作動流体組成物 - Google Patents
冷凍機油および冷凍機用作動流体組成物 Download PDFInfo
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- JP5546726B2 JP5546726B2 JP2007334916A JP2007334916A JP5546726B2 JP 5546726 B2 JP5546726 B2 JP 5546726B2 JP 2007334916 A JP2007334916 A JP 2007334916A JP 2007334916 A JP2007334916 A JP 2007334916A JP 5546726 B2 JP5546726 B2 JP 5546726B2
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- Prior art keywords
- acid
- hfc
- branched
- linear
- refrigerant
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- 239000000203 mixture Substances 0.000 title claims description 59
- 239000012530 fluid Substances 0.000 title claims description 26
- 239000003507 refrigerant Substances 0.000 claims description 96
- 239000010721 machine oil Substances 0.000 claims description 55
- RWRIWBAIICGTTQ-UHFFFAOYSA-N difluoromethane Chemical compound FCF RWRIWBAIICGTTQ-UHFFFAOYSA-N 0.000 claims description 42
- 239000002253 acid Substances 0.000 claims description 41
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 claims description 37
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 claims description 37
- 150000002148 esters Chemical class 0.000 claims description 26
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- GTLACDSXYULKMZ-UHFFFAOYSA-N pentafluoroethane Chemical compound FC(F)C(F)(F)F GTLACDSXYULKMZ-UHFFFAOYSA-N 0.000 claims description 22
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 claims description 19
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 16
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- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 10
- NPNPZTNLOVBDOC-UHFFFAOYSA-N 1,1-difluoroethane Chemical compound CC(F)F NPNPZTNLOVBDOC-UHFFFAOYSA-N 0.000 claims description 8
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- 125000001931 aliphatic group Chemical group 0.000 claims description 8
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 claims description 8
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- FYIRUPZTYPILDH-UHFFFAOYSA-N 1,1,1,2,3,3-hexafluoropropane Chemical compound FC(F)C(F)C(F)(F)F FYIRUPZTYPILDH-UHFFFAOYSA-N 0.000 claims description 7
- NSGXIBWMJZWTPY-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropane Chemical compound FC(F)(F)CC(F)(F)F NSGXIBWMJZWTPY-UHFFFAOYSA-N 0.000 claims description 7
- WXGNWUVNYMJENI-UHFFFAOYSA-N 1,1,2,2-tetrafluoroethane Chemical compound FC(F)C(F)F WXGNWUVNYMJENI-UHFFFAOYSA-N 0.000 claims description 7
- 239000004215 Carbon black (E152) Substances 0.000 claims description 7
- UHCBBWUQDAVSMS-UHFFFAOYSA-N fluoroethane Chemical compound CCF UHCBBWUQDAVSMS-UHFFFAOYSA-N 0.000 claims description 7
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- WZLFPVPRZGTCKP-UHFFFAOYSA-N 1,1,1,3,3-pentafluorobutane Chemical compound CC(F)(F)CC(F)(F)F WZLFPVPRZGTCKP-UHFFFAOYSA-N 0.000 claims description 5
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- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 5
- 239000001294 propane Substances 0.000 claims description 5
- OFHCXWMZXQBQMH-UHFFFAOYSA-N trifluoro(trifluoromethylsulfanyl)methane Chemical compound FC(F)(F)SC(F)(F)F OFHCXWMZXQBQMH-UHFFFAOYSA-N 0.000 claims description 5
- 239000001282 iso-butane Substances 0.000 claims description 4
- IJDNQMDRQITEOD-UHFFFAOYSA-N sec-butylidene Natural products CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 3
- -1 polyol esters Chemical class 0.000 description 43
- 229910019142 PO4 Inorganic materials 0.000 description 30
- 239000010452 phosphate Substances 0.000 description 30
- 235000021317 phosphate Nutrition 0.000 description 30
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 28
- VJGCZWVJDRIHNC-UHFFFAOYSA-N 1-fluoroprop-1-ene Chemical compound CC=CF VJGCZWVJDRIHNC-UHFFFAOYSA-N 0.000 description 21
- 239000004593 Epoxy Substances 0.000 description 19
- 150000001875 compounds Chemical class 0.000 description 19
- HBGGXOJOCNVPFY-UHFFFAOYSA-N diisononyl phthalate Chemical compound CC(C)CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC(C)C HBGGXOJOCNVPFY-UHFFFAOYSA-N 0.000 description 17
- 239000003921 oil Substances 0.000 description 15
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- 239000002199 base oil Substances 0.000 description 13
- 238000005057 refrigeration Methods 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 150000005846 sugar alcohols Polymers 0.000 description 8
- 239000000654 additive Substances 0.000 description 7
- UJPMYEOUBPIPHQ-UHFFFAOYSA-N 1,1,1-trifluoroethane Chemical compound CC(F)(F)F UJPMYEOUBPIPHQ-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- MSSNHSVIGIHOJA-UHFFFAOYSA-N pentafluoropropane Chemical compound FC(F)CC(F)(F)F MSSNHSVIGIHOJA-UHFFFAOYSA-N 0.000 description 6
- 229920001515 polyalkylene glycol Polymers 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 5
- 229930195729 fatty acid Natural products 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- 150000004665 fatty acids Chemical class 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 239000002480 mineral oil Substances 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical class OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 5
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 4
- OHMHBGPWCHTMQE-UHFFFAOYSA-N 2,2-dichloro-1,1,1-trifluoroethane Chemical compound FC(F)(F)C(Cl)Cl OHMHBGPWCHTMQE-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 150000004996 alkyl benzenes Chemical class 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 4
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 4
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 4
- 150000003014 phosphoric acid esters Chemical class 0.000 description 4
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- 239000011574 phosphorus Substances 0.000 description 4
- 229920005862 polyol Polymers 0.000 description 4
- 229920001289 polyvinyl ether Polymers 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 3
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229920001774 Perfluoroether Polymers 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
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- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 3
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- KOWVWXQNQNCRRS-UHFFFAOYSA-N tris(2,4-dimethylphenyl) phosphate Chemical compound CC1=CC(C)=CC=C1OP(=O)(OC=1C(=CC(C)=CC=1)C)OC1=CC=C(C)C=C1C KOWVWXQNQNCRRS-UHFFFAOYSA-N 0.000 description 1
- HQUQLFOMPYWACS-UHFFFAOYSA-N tris(2-chloroethyl) phosphate Chemical compound ClCCOP(=O)(OCCCl)OCCCl HQUQLFOMPYWACS-UHFFFAOYSA-N 0.000 description 1
- XHTMGDWCCPGGET-UHFFFAOYSA-N tris(3,3-dichloropropyl) phosphate Chemical compound ClC(Cl)CCOP(=O)(OCCC(Cl)Cl)OCCC(Cl)Cl XHTMGDWCCPGGET-UHFFFAOYSA-N 0.000 description 1
- QQBLOZGVRHAYGT-UHFFFAOYSA-N tris-decyl phosphite Chemical compound CCCCCCCCCCOP(OCCCCCCCCCC)OCCCCCCCCCC QQBLOZGVRHAYGT-UHFFFAOYSA-N 0.000 description 1
- SVETUDAIEHYIKZ-IUPFWZBJSA-N tris[(z)-octadec-9-enyl] phosphate Chemical compound CCCCCCCC\C=C/CCCCCCCCOP(=O)(OCCCCCCCC\C=C/CCCCCCCC)OCCCCCCCC\C=C/CCCCCCCC SVETUDAIEHYIKZ-IUPFWZBJSA-N 0.000 description 1
- WYFGCJADJYRNAK-UHFFFAOYSA-N tritetradecyl phosphate Chemical compound CCCCCCCCCCCCCCOP(=O)(OCCCCCCCCCCCCCC)OCCCCCCCCCCCCCC WYFGCJADJYRNAK-UHFFFAOYSA-N 0.000 description 1
- XEQUZHYCHCGTJX-UHFFFAOYSA-N tritridecyl phosphate Chemical compound CCCCCCCCCCCCCOP(=O)(OCCCCCCCCCCCCC)OCCCCCCCCCCCCC XEQUZHYCHCGTJX-UHFFFAOYSA-N 0.000 description 1
- SUZOHRHSQCIJDK-UHFFFAOYSA-N triundecyl phosphate Chemical compound CCCCCCCCCCCOP(=O)(OCCCCCCCCCCC)OCCCCCCCCCCC SUZOHRHSQCIJDK-UHFFFAOYSA-N 0.000 description 1
- UKPASDNOVTUNJT-UHFFFAOYSA-N triundecyl phosphite Chemical compound CCCCCCCCCCCOP(OCCCCCCCCCCC)OCCCCCCCCCCC UKPASDNOVTUNJT-UHFFFAOYSA-N 0.000 description 1
- WMYJOZQKDZZHAC-UHFFFAOYSA-H trizinc;dioxido-sulfanylidene-sulfido-$l^{5}-phosphane Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([S-])=S.[O-]P([O-])([S-])=S WMYJOZQKDZZHAC-UHFFFAOYSA-H 0.000 description 1
- KJIOQYGWTQBHNH-UHFFFAOYSA-N undecanol Chemical compound CCCCCCCCCCCO KJIOQYGWTQBHNH-UHFFFAOYSA-N 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
Landscapes
- Lubricants (AREA)
Description
飽和ハイドロフルオロカーボンとしては、ジフルオロメタン(HFC−32)、ペンタフルオロエタン(HFC−125)、1,1,2,2−テトラフルオロエタン(HFC−134)、1,1,1,2−テトラフルオロエタン(HFC−134a)、1,1−ジフルオロエタン(HFC−152a)、フルオロエタン(HFC−161)、1,1,1,2,3,3,3−ヘプタフルオロプロパン(HFC−227ea)、1,1,1,2,3,3−ヘキサフルオロプロパン(HFC−236ea)、1,1,1,3,3,3−ヘキサフルオロプロパン(HFC−236fa)、1,1,1,3,3−ペンタフルオロプロパン(HFC−245fa)および1,1,1,3,3−ペンタフルオロブタン(HFC−365mfc)から選ばれる少なくとも1種が好ましく;
炭素数3〜5の炭化水素としては、プロパン、ノルマルブタン、イソブタン、2−メチルブタンおよびノルマルペンタンから選ばれる少なくとも1種であることが好ましい。
1種の芳香族カルボン酸と1種の1価アルコールとの完全エステル、
1種の芳香族カルボン酸と2種以上の1価アルコールとの完全エステル、
1種の芳香族カルボン酸と1種の多価アルコールとの完全エステル、
1種の芳香族カルボン酸と2種以上の多価アルコールとの完全エステル、
2種以上の芳香族カルボン酸と1種の1価アルコールとの完全エステル、
2種以上の芳香族カルボン酸と2種以上の1価アルコールとの完全エステル、
2種以上の芳香族カルボン酸と1種の多価アルコールとの完全エステル
2種以上の芳香族カルボン酸と2種以上の多価アルコールとの完全エステル
のいずれであってもよい。
実施例1〜2および比較例1〜4においては、それぞれ以下に示す基油1〜6を用いて冷凍機油を調製した。得られた冷凍機油の各種性状を表1に示す。
基油1:フタル酸ジ−(2−エチルヘキシル)
基油2:フタル酸ジ−(3,5,5−トリメチルへキシル)
基油3:トリメリット酸トリ−(2−エチルヘキシル)
基油4:ピロメリット酸テトラエステル(アルコールはn−ヘプタノールとn−ノナノールの等モル混合物)
基油5:ポリエチレンプロピレングリコールジメチルエーテル。(エチレン基/プロピレン基のモル比:50/50)
基油6:n−ヘプタン酸とペンタエリスリトールとのエステル。
基油7:ナフテン系鉱油。
JIS−K−2211「冷凍機油」の「冷媒との相溶性試験方法」に準拠して、2,3,3,3−テトラフルオロプロペンと3フッ化ヨウ化メタンの混合冷媒(混合比(質量比):2,3,3,3−テトラフルオロプロペン/3フッ化ヨウ化メタン=70/30)19gに対して冷凍機油を1g配合し、冷媒と冷凍機油とが0℃において相互に溶解しているかを観察した。得られた結果を表1〜2に示す。表1〜11中、「相溶」は冷媒と冷凍機油とが相互に溶解したことを意味し、「分離」は冷媒と冷凍機油とが2層に分離したことを意味する。
JIS−K−2211「冷凍機油」の「冷媒との相溶性試験方法」に準拠して、2,3,3,3−テトラフルオロプロペン19gに対して冷凍機油を1g配合し、冷媒と冷凍機油とが0℃において相互に溶解しているかを観察した。得られた結果を表1〜2に示す。表1中、「相溶」は冷媒と冷凍機油とが相互に溶解したことを意味し、「分離」は冷媒と冷凍機油とが2層に分離したことを意味する。
JIS−K−2211に準拠し、水分を10ppm以下に調整した冷凍機油組成物(初期色相L0.5)1gと、2,3,3,3−テトラフルオロプロペンと3フッ化ヨウ化メタンの混合冷媒(混合比(質量比):2,3,3,3−テトラフルオロプロペン/3フッ化ヨウ化メタン=70/30)1gと、触媒(鉄、銅、アルミの各線)とをガラス管に封入した後、150℃に加熱して1週間保持し試験した。試験後は冷凍機油組成物の色相および触媒の色変化を評価した。色相は、ASTM D156に準拠して評価した。また、触媒の色変化は、外観を目視で観察し、変化なし、光沢なし、黒化のいずれに該当するかを評価した。得られた結果を表1〜2に示す。
JIS−K−2211に準拠し、水分を100ppm以下に調整した冷凍機油(初期色相L0.5)1gと、2,3,3,3−テトラフルオロプロペン1gと、触媒(鉄、銅、アルミの各線)とをガラス管に封入した後、150℃に加熱して1週間保持し試験した。試験後は冷凍機油組成物の色相および触媒の色変化を評価した。色相は、ASTM D156に準拠して評価した。また、触媒の色変化は、外観を目視で観察し、変化なし、光沢なし、黒化のいずれに該当するかを評価した。得られた結果を表1〜2に示す。
Claims (4)
- フタル酸、イソフタル酸、テレフタル酸、トリメリット酸及びピロメリット酸から選ばれる少なくとも1種の芳香族カルボン酸と炭素数2〜15の脂肪族1価アルコールとのエステルと、2,3,3,3−テトラフルオロプロペンと、を含有することを特徴とする冷凍機用作動流体組成物。
- 前記2,3,3,3−テトラフルオロプロペンと、飽和ハイドロフルオロカーボン、炭素数3〜5の炭化水素、ジメチルエーテル、二酸化炭素、ビス(トリフルオロメチル)サルファイドおよび3フッ化ヨウ化メタン冷媒から選ばれる少なくとも1種とを含有することを特徴とする、請求項1に記載の冷凍機用作動流体組成物。
- 前記飽和ハイドロフルオロカーボンが、ジフルオロメタン、ペンタフルオロエタン、1,1,2,2−テトラフルオロエタン、1,1,1,2−テトラフルオロエタン、1,1−ジフルオロエタン、フルオロエタン、1,1,1,2,3,3,3−ヘプタフルオロプロパン、1,1,1,2,3,3−ヘキサフルオロプロパン、1,1,1,3,3,3−ヘキサフルオロプロパン、1,1,1,3,3−ペンタフルオロプロパンおよび1,1,1,3,3−ペンタフルオロブタンから選ばれる少なくとも1種であり、前記炭素数3〜5の炭化水素が、プロパン、ノルマルブタン、イソブタン、2−メチルブタンおよびノルマルペンタンから選ばれる少なくとも1種であることを特徴とする、請求項2に記載の冷凍機用作動流体組成物。
- フタル酸、イソフタル酸、テレフタル酸、トリメリット酸及びピロメリット酸から選ばれる少なくとも1種の芳香族カルボン酸と炭素数2〜15の脂肪族1価アルコールとのエステルを含有し、2,3,3,3−テトラフルオロプロペンと共に用いられることを特徴とする冷凍機油。
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