JP6641346B2 - 冷凍機油及び冷凍機用作動流体組成物 - Google Patents
冷凍機油及び冷凍機用作動流体組成物 Download PDFInfo
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- JP6641346B2 JP6641346B2 JP2017238736A JP2017238736A JP6641346B2 JP 6641346 B2 JP6641346 B2 JP 6641346B2 JP 2017238736 A JP2017238736 A JP 2017238736A JP 2017238736 A JP2017238736 A JP 2017238736A JP 6641346 B2 JP6641346 B2 JP 6641346B2
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- 239000012530 fluid Substances 0.000 title claims description 15
- 238000005057 refrigeration Methods 0.000 title description 5
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- 229910052760 oxygen Inorganic materials 0.000 claims description 30
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- MIZLGWKEZAPEFJ-UHFFFAOYSA-N 1,1,2-trifluoroethene Chemical group FC=C(F)F MIZLGWKEZAPEFJ-UHFFFAOYSA-N 0.000 claims description 19
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- 239000002253 acid Substances 0.000 claims description 19
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- 239000002199 base oil Substances 0.000 claims description 14
- 239000002516 radical scavenger Substances 0.000 claims description 4
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- 235000014113 dietary fatty acids Nutrition 0.000 description 30
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- 238000004519 manufacturing process Methods 0.000 description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
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- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 4
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 3
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical class C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 3
- 125000003229 2-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- OILUAKBAMVLXGF-UHFFFAOYSA-N 3,5,5-trimethyl-hexanoic acid Chemical compound OC(=O)CC(C)CC(C)(C)C OILUAKBAMVLXGF-UHFFFAOYSA-N 0.000 description 3
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 3
- GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 3
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- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
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- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
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- QQWAKSKPSOFJFF-UHFFFAOYSA-N oxiran-2-ylmethyl 2,2-dimethyloctanoate Chemical compound CCCCCCC(C)(C)C(=O)OCC1CO1 QQWAKSKPSOFJFF-UHFFFAOYSA-N 0.000 description 3
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- 125000000755 henicosyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- YAQXGBBDJYBXKL-UHFFFAOYSA-N iron(2+);1,10-phenanthroline;dicyanide Chemical compound [Fe+2].N#[C-].N#[C-].C1=CN=C2C3=NC=CC=C3C=CC2=C1.C1=CN=C2C3=NC=CC=C3C=CC2=C1 YAQXGBBDJYBXKL-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 125000002463 lignoceryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 125000002960 margaryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000006078 metal deactivator Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- GMEUEHIGFJMSTL-UHFFFAOYSA-N n,n'-bis(2,3-dibutylphenyl)methanediimine Chemical compound CCCCC1=CC=CC(N=C=NC=2C(=C(CCCC)C=CC=2)CCCC)=C1CCCC GMEUEHIGFJMSTL-UHFFFAOYSA-N 0.000 description 1
- WCQUXQDPAFJFHB-UHFFFAOYSA-N n,n'-bis(2-butylphenyl)methanediimine Chemical compound CCCCC1=CC=CC=C1N=C=NC1=CC=CC=C1CCCC WCQUXQDPAFJFHB-UHFFFAOYSA-N 0.000 description 1
- POOVXLCLGSARNP-UHFFFAOYSA-N n,n'-bis(2-propan-2-ylphenyl)methanediimine Chemical compound CC(C)C1=CC=CC=C1N=C=NC1=CC=CC=C1C(C)C POOVXLCLGSARNP-UHFFFAOYSA-N 0.000 description 1
- ONWRHZSCWAZSHZ-UHFFFAOYSA-N n,n'-bis[2,3,4-tri(propan-2-yl)phenyl]methanediimine Chemical compound CC(C)C1=C(C(C)C)C(C(C)C)=CC=C1N=C=NC1=CC=C(C(C)C)C(C(C)C)=C1C(C)C ONWRHZSCWAZSHZ-UHFFFAOYSA-N 0.000 description 1
- CMESPBFFDMPSIY-UHFFFAOYSA-N n,n'-diphenylmethanediimine Chemical compound C1=CC=CC=C1N=C=NC1=CC=CC=C1 CMESPBFFDMPSIY-UHFFFAOYSA-N 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 125000001196 nonadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- XRQKARZTFMEBBY-UHFFFAOYSA-N oxiran-2-ylmethyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1CO1 XRQKARZTFMEBBY-UHFFFAOYSA-N 0.000 description 1
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 1
- UJMWVICAENGCRF-UHFFFAOYSA-N oxygen difluoride Chemical class FOF UJMWVICAENGCRF-UHFFFAOYSA-N 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- MSSNHSVIGIHOJA-UHFFFAOYSA-N pentafluoropropane Chemical compound FC(F)CC(F)(F)F MSSNHSVIGIHOJA-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920013636 polyphenyl ether polymer Polymers 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 239000010726 refrigerant oil Substances 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QZZGJDVWLFXDLK-UHFFFAOYSA-N tetracosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCC(O)=O QZZGJDVWLFXDLK-UHFFFAOYSA-N 0.000 description 1
- 125000002469 tricosyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Landscapes
- Lubricants (AREA)
Description
[上記式(A−1)中、X1は水素原子、アルキル基、シクロアルキル基又は下記一般式(A−2):
Y2−(OA3)e− (A−2)
(上記式(A−2)中、Y2は水素原子、アルキル基又はシクロアルキル基を示し、A3は炭素数2〜4のアルキレン基を示し、eは1〜50の整数を示す)で表される基を示し、A1及びA2は同一でも異なっていてもよく、それぞれ炭素数2〜4のアルキレン基を示し、Y1は水素原子、アルキル基又はシクロアルキル基を示し、Bは水酸基3〜20個を有する化合物の残基を示し、aは1〜20、bは0〜19でかつa+b=3〜20となる整数を示し、cは0〜50の整数、dは1〜50の整数をそれぞれ示す]
[式中、R1、R2及びR3は互いに同一でも異なっていてもよく、それぞれ水素原子又は炭化水素基を示し、R4は二価の炭化水素基又は二価のエーテル結合酸素含有炭化水素基を示し、R5は炭化水素基を示し、mは0以上の整数を示す。mが2以上である場合には、複数のR4は互いに同一でも異なっていてもよい。]
[式中、R6〜R9は互いに同一でも異なっていてもよく、それぞれ水素原子又は炭素数1〜20の炭化水素基を示す。]
[式中、R1、R2、R3、R4、R5及びmは、それぞれ一般式(1)中のR1、R2、R3、R4、R5及びmと同一の定義内容を示す。]
[式中、R11、R21及びR31は互いに同一でも異なっていてもよく、それぞれ水素原子又は炭素数1〜8の炭化水素基を示し、R41は炭素数1〜10の二価の炭化水素基又は二価のエーテル結合酸素含有炭化水素基を示し、R51は炭素数1〜20の炭化水素基を示し、mは一般式(1)中のmと同一の定義内容を示す。mが2以上の場合には、複数のR41は互いに同一でも異なっていてもよい。]
[式中、R61、R71、R81及びR91は互いに同一でも異なっていてもよく、それぞれ水素原子又は炭素数1〜20の炭化水素基を示す。]
[式中、R12,R22及びR32は互いに同一でも異なっていてもよく、それぞれ水素原子又は炭素数1〜8の炭化水素基を示し、R42は炭素数1〜10の二価の炭化水素基又は二価のエーテル結合酸素含有炭化水素基を示し、R52は炭素数1〜20の炭化水素基を示し、mは一般式(1)中のmと同一の定義内容を示す。mが2以上の場合には、複数のR41は同一でも異なっていてもよい。]
[式中、R62、R72、R82及びR92は互いに同一でも異なっていてもよく、それぞれ水素原子又は炭素数1〜20の炭化水素基を示す。]
[式中、R13、R23及びR33は互いに同一でも異なっていてもよく、それぞれ水素原子又は炭素数1〜8の炭化水素基を示す。]
(a)一方の末端が一般式(4)又は(5)で表され、かつ他方の末端が一般式(6)又は(7)で表される構造を有し、一般式(1)におけるR1、R2及びR3がいずれも水素原子、mが0〜4の整数、R4が炭素数2〜4の二価の炭化水素基、R5が炭素数1〜20の炭化水素基であるもの。
(b)一般式(1)で表される構造単位のみを有するものであって、一方の末端が一般式(4)で表され、かつ他方の末端が一般式(6)で表される構造を有し、一般式(1)におけるR1、R2及びR3がいずれも水素原子、mが0〜4の整数、R4が炭素数2〜4の二価の炭化水素基、R5が炭素数1〜20の炭化水素基であるもの。
(c)一方の末端が一般式(4)又は(5)で表され、かつ他方の末端が一般式(8)で表される構造を有し、一般式(1)におけるR1、R2及びR3がいずれも水素原子、mが0〜4の整数、R4が炭素数2〜4の二価の炭化水素基、R5が炭素数1〜20の炭化水素基であるもの。
(d)一般式(1)で表される構造単位のみを有するものであって、一方の末端が一般式(5)で表され、かつ他方の末端が一般式(8)で表される構造を有し、一般式(1)におけるR1、R2及びR3がいずれも水素原子、mが0〜4の整数、R4が炭素数2〜4の二価の炭化水素基、R5が炭素数1〜20の炭化水素基であるもの。
(e)上記(a),(b),(c)及び(d)のいずれかであって、一般式(1)におけるR5が炭素数1〜3の炭化水素基である構造単位と該R5が炭素数3〜20の炭化水素基である構造単位とを有するもの。
Rα−[(ORβ)f−ORγ]g (9)
[式(1)中、Rαは水素原子、炭素数1〜10のアルキル基、炭素数2〜10のアシル基又は水酸基を2〜8個有する化合物の残基を表し、Rβは炭素数2〜4のアルキレン基を表し、Rγは水素原子、炭素数1〜10のアルキル基又は炭素数2〜10のアシル基を表し、fは1〜80の整数を表し、gは1〜8の整数を表す。]
iC4:2−メチルプロパン酸
nC5:n−ペンタン酸
iC8:2−エチルヘキサン酸
iC9:3,5,5−トリメチルヘキサン酸
nC10:n−デカン酸
iC18:2−エチルヘキサデカン酸
PET:ペンタエリスリトール
添加剤1:グリシジルネオデカノエート
添加剤2:2−エチルヘキシルグリシジルエーテル
添加剤3:ビス(ジイソプロピルフェニル)カルボジイミド
添加剤4:ジイソプロピルカルボジイミド
安定性試験は、JIS K2211−09(オートクレーブテスト)に準拠して行った。具体的には、含有水分量を100ppmに調整した供試油80gをオートクレーブに秤取し、触媒(鉄、銅、アルミの線、いずれも外径1.6mm×長さ50mm)、及び、下記混合冷媒A〜Cから選ばれるいずれかの混合冷媒20gを封入した後、140℃に加熱し、150時間後の供試油の酸価(JIS C2101)を測定した。
混合冷媒A:2,3,3,3−テトラフルオロプロペン(HFO−1234yf)とトリフルオロエチレン(HFO−1123)との混合冷媒(質量比(HFO−1234yf/HFO−1123)=80/20)
混合冷媒B:ジフルオロメタン(HFC−32)とトリフルオロエチレン(HFO−1123)との混合冷媒(質量比(HFC−32/HFO−1123)=40/60)
混合冷媒C:1,1,1,2−テトラフルオロエタン(HFC−134a)とトリフルオロエチレン(HFO−1123)との混合冷媒(質量比(HFC−134a/HFO−1123)=20/80)
JIS−K−2211「冷凍機油」の「冷媒との相溶性試験方法」に準拠して、前記混合冷媒A〜Cのそれぞれ10gに対して供試油を10g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。
Claims (4)
- 炭素/酸素モル比が3.2以上5.0以下であり、ポリオールエステル及びポリビニルエーテルからなる群より選ばれる少なくとも1種の含酸素油を基油として含有し、
酸捕捉剤を更に含有し、
前記含酸素油の含有量が、基油全量基準で95質量%以上であり、
トリフルオロエチレンと、ジフルオロメタンとを含む冷媒と共に用いられる、冷凍機油。 - 前記トリフルオロエチレンの含有量が、冷媒全量基準で20質量%以上である、請求項1に記載の冷凍機油。
- 炭素/酸素モル比が3.2以上5.0以下であり、ポリオールエステル及びポリビニルエーテルからなる群より選ばれる少なくとも1種の含酸素油を基油として含有し、酸捕捉剤を更に含有し、前記含酸素油の含有量が基油全量基準で95質量%以上である、冷凍機油と、
トリフルオロエチレンと、ジフルオロメタンとを含む冷媒と、
を含有する、冷凍機用作動流体組成物。 - 前記トリフルオロエチレンの含有量が、冷媒全量基準で20質量%以上である、請求項3に記載の冷凍機用作動流体組成物。
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