JP5871688B2 - 冷凍機用作動流体組成物 - Google Patents
冷凍機用作動流体組成物 Download PDFInfo
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- JP5871688B2 JP5871688B2 JP2012076301A JP2012076301A JP5871688B2 JP 5871688 B2 JP5871688 B2 JP 5871688B2 JP 2012076301 A JP2012076301 A JP 2012076301A JP 2012076301 A JP2012076301 A JP 2012076301A JP 5871688 B2 JP5871688 B2 JP 5871688B2
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- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- UJMWVICAENGCRF-UHFFFAOYSA-N oxygen difluoride Chemical compound FOF UJMWVICAENGCRF-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 239000002530 phenolic antioxidant Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical class OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920013636 polyphenyl ether polymer Polymers 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 150000003580 thiophosphoric acid esters Chemical class 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-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
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 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
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- C09K5/041—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems
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- C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
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- C10M107/30—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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- C10M171/008—Lubricant compositions compatible with refrigerants
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- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F25—REFRIGERATION OR COOLING; COMBINED HEATING AND REFRIGERATION SYSTEMS; HEAT PUMP SYSTEMS; MANUFACTURE OR STORAGE OF ICE; LIQUEFACTION SOLIDIFICATION OF GASES
- F25B—REFRIGERATION MACHINES, PLANTS OR SYSTEMS; COMBINED HEATING AND REFRIGERATION SYSTEMS; HEAT PUMP SYSTEMS
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Description
ポリオールエステル、ポリビニルエーテルおよびポリアルキレングリコール化合物から選ばれる少なくとも1種を基油として含有し、該基油の炭素/酸素モル比が2.5以上5.8以下である冷凍機油と、
を含有する冷凍機用作動流体組成物を提供する。
CpHqFr (A)
[式中、pは1〜4の整数を示し、qは1〜10の整数を示し、rは0〜5の整数を示す。]
[式中、R1,R2およびR3は同一でも異なっていてもよく、それぞれ水素原子または炭素数1〜8の炭化水素基を示し、R4は炭素数1〜10の二価の炭化水素基または炭素数2〜20の二価のエーテル結合酸素含有炭化水素基を示し、R5は炭素数1〜20の炭化水素基を示し、mは前記ポリビニルエーテルについてのmの平均値が0〜10となるような数を示し、R1〜R5は構造単位毎に同一であっても異なっていてもよく、一の構造単位においてmが2以上である場合には、複数のR4Oは同一でも異なっていてもよい。]
モノフルオロエタンを含有する冷媒と、
ポリオールエステル、ポリビニルエーテルおよびポリアルキレングリコール化合物から選ばれる少なくとも1種を基油として含有し、該基油の炭素/酸素モル比が2.5以上5.8以下である冷凍機油と、
を含有する。
C2HnF6−n (A)
[式中、nは1または2を示す。]
本実施形態における冷媒はモノフルオロエタン(HFC−161)を含有する。モノフルオロエタンは分子内にフッ素を1個有し、特徴的な特性を示す。
CpHqFr (A)
[式中、pは1〜4の整数を示し、qは1〜10の整数を示し、rは0〜5の整数を示す。]
また、効率を高めるためには高圧な冷媒、つまり沸点の低い冷媒を配合することになるが、プロパンは強燃性であることから、HFC−32、HFC−143a、HFC−125が候補となる。
本実施形態に係る冷凍機油はポリオールエステル、ポリビニルエーテルおよびポリアルキレングリコール化合物から選ばれる少なくとも1種を基油として含有し、該基油の炭素/酸素モル比は2.5以上5.8以下である。基油中の炭素および酸素については、一般的な元素分析法により定量分析することができる。炭素分析については燃焼により二酸化炭素に変換した後の熱伝導度法やガスクロマトグラフィー法などがあり、酸素分析については炭素により一酸化炭素に導き定量分析する炭素還元法が一般的であり、Shutze−Unterzaucher法が広く実用化されている。
ポリオールエステルは、多価アルコールとカルボン酸とから合成されるエステルであり、炭素/酸素モル比が、好ましくは2.5以上5.8以下であり、より好ましくは3.2以上5.0以下であり、更に好ましくは4.0以上5.0以下である。カルボン酸としては、脂肪酸(1価脂肪族カルボン酸)、特には飽和脂肪酸が好ましく用いられ、その炭素数は4以上9以下が、特には5以上9以下が好ましい。ポリオールエステルは、多価アルコールの水酸基の一部がエステル化されずに水酸基のまま残っている部分エステルであっても良く、全ての水酸基がエステル化された完全エステルであっても良く、また部分エステルと完全エステルの混合物であっても良いが、水酸基価が好ましくは10mgKOH/g以下、さらに好ましくは5mgKOH/g以下、最も好ましくは3mgKOH/g以下であることが好ましい。
(a)冷媒の主成分である上記一般式(A)で示されるハイドロフルオロエタン、ジフルオロメタンおよび2,3,3,3−テトラフルオロプロペンのうち、冷凍機油との相溶性に劣るジフルオロメタンの割合が多い場合、例えば冷媒中のジフルオロメタンの割合が40質量%以上の場合には、ポリオールエステルを構成する脂肪酸のうち、分岐脂肪酸の割合が50〜100モル%、特には70〜100モル%、更には90〜100モル%が好ましい。
ポリオールエステルを構成する多価アルコールとしては、水酸基を2〜6個有する多価アルコールが好ましく用いられる。多価アルコールの炭素数としては、4〜12、特には5〜10が好ましい。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、トリメチロールブタン、ジ−(トリメチロールプロパン)、トリ−(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)などのヒンダードアルコールが好ましい。冷媒との相溶性および加水分解安定性に特に優れることからペンタエリスリトールまたはペンタエリスリトールとジ−(ペンタエリスリトール)の混合エステルが最も好ましい。
ポリビニルエーテルの炭素/酸素モル比は、好ましく2.5以上5.8以下であり、より好ましくは3.2以上5.8以下であり、更に好ましくは4.0以上5.0以下である。炭素/酸素モル比がこの範囲未満では吸湿性が高くなり、この範囲を超えると相溶性が低下する。また、ポリビニルエーテルの重量平均分子量は、好ましくは200以上3000以下、より好ましくは500以上1500以下である。
[式中、R1,R2およびR3は同一でも異なっていてもよく、それぞれ水素原子または炭素数1〜8の炭化水素基を示し、R4は炭素数1〜10の二価の炭化水素基または炭素数2〜20の二価のエーテル結合酸素含有炭化水素基を示し、R5は炭素数1〜20の炭化水素基を示し、mは前記ポリビニルエーテルについてのmの平均値が0〜10となるような数を示し、R1〜R5は構造単位毎に同一であっても異なっていてもよく、一の構造単位においてmが2以上である場合には、複数のR4Oは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、それぞれ水素原子または炭素数1〜20の炭化水素基を示す。]
本実施形態に係るポリビニルエーテルは、それぞれ対応するビニルエーテル系モノマーの重合、および対応するオレフィン性二重結合を有する炭化水素モノマーと対応するビニルエーテル系モノマーとの共重合により製造することができる。一般式(1)で表される構造単位に対応するビニルエーテル系モノマーとしては、下記一般式(3)で表されるモノマーが好適である。
[式中、R1、R2、R3、R4、R5およびmは、それぞれ一般式(1)中のR1、R2、R3、R4、R5およびmと同一の定義内容を示す。]
(A)一方の末端が、一般式(4)または(5)で表され、かつ他方の末端が一般式(6)または(7)で表される構造を有するもの。
[式中、R11、R21およびR31は互いに同一でも異なっていてもよく、それぞれ水素原子または炭素数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または炭素数2〜20の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はポリビニルエーテルについてのmの平均値が0〜10となるような数を示し、mが2以上の場合には、複数のR41Oは同一でも異なっていてもよい。]
[式中、R61、R71、R81およびR91は互いに同一でも異なっていてもよく、それぞれ水素原子または炭素数1〜20の炭化水素基を示す。]
[式中、R12,R22およびR32は互いに同一でも異なっていてもよく、それぞれ水素原子または炭素数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または炭素数2〜20の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はポリビニルエーテルについてのmの平均値が0〜10となるような数を示し、mが2以上の場合には、複数のR41Oは同一でも異なっていてもよい。]
[式中、R62、R72、R82およびR92は互いに同一でも異なっていてもよく、それぞれ水素原子または炭素数1〜20の炭化水素基を示す。]
[式中、R13、R23およびR33は互いに同一でも異なっていてもよく、それぞれ水素原子または炭素数1〜8の炭化水素基を示す。]
(1)一方の末端が一般式(5)または(6)で表され、かつ他方の末端が一般式(7)または(8)で表される構造を有し、一般式(1)におけるR1、R2およびR3が共に水素原子、mが0〜4の数、R4が炭素数2〜4の二価の炭化水素基およびR5が炭素数1〜20の炭化水素基であるもの。
(2)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(7)で表される構造を有し、一般式(1)におけるR1、R2およびR3が共に水素原子、mが0〜4の数、R4が炭素数2〜4の二価の炭化水素基およびR5が炭素数1〜20の炭化水素基であるもの。
(3)一方の末端が一般式(5)または(6)で表され、かつ他方の末端が一般式(9)で表される構造を有し、一般式(1)におけるR1、R2およびR3が共に水素原子、mが0〜4の数、R4が炭素数2〜4の二価の炭化水素基およびR5が炭素数1〜20の炭化水素基であるもの。
(4)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、その一方の末端が一般式(III)で表され、かつ他方の末端が一般式(9)で表される構造を有し、一般式(1)におけるR1、R2およびR3が共に水素原子、mが0〜4の数、R4が炭素数2〜4の二価の炭化水素基およびR5が炭素数1〜20の二価の炭化水素基およびR5が炭素数1〜20の炭化水素基であるもの。
(5)上記(1)〜(4)の各々であって、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を有するもの。
本実施形態に係るポリビニルエーテルは、前記したモノマーをラジカル重合、カチオン重合、放射線重合などによって製造することができる。重合反応終了後、必要に応じて通常の分離・精製方法を施すことにより、目的とする一般式(1)で表される構造単位を有するポリビニルエーテル系化合物が得られる。
本実施形態に係るポリアルキレングリコール(PAG)化合物の炭素/酸素モル比は、好ましくは2.5以上5.8以下であり、好ましくは2.5以上4.0以下であり、更に好ましくは2.7以上3.5以下である。モル比がこの範囲未満では吸湿性が高く、電気絶縁性が低くなり、この範囲を超えると相溶性が低下する。当該ポリアルキレングリコール化合物の重量平均分子量は、好ましくは200以上3000以下、より好ましくは500以上1500以下である。
ポリアルキレングリコールは種々の化学構造のものがあるが、ポリエチレングリコール、ポリプロピレングリコール、ポリブチレングリコールなどが基本化合物で、単位構造はオキシエチレン、オキシプロピレン、オキシブチレンであり、それぞれモノマーであるエチレンオキサイド、プロピレンオキサイド、ブチレンオキサイドを原料として、開環重合により得ることができる。
R1−〔(OR2)f−OR3〕g (1)
[式(1)中、R1は水素原子、炭素数1〜10のアルキル基、炭素数2〜10のアシル基または水酸基を2〜8個有する化合物の残基を表し、R2は炭素数2〜4のアルキレン基を表し、R3は水素原子、炭素数1〜10のアルキル基または炭素数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。]
まず、以下に示す基油1〜4に酸化防止剤であるジ−ter.−ブチル−p−クレゾ−ル(DBPC)を0.1質量%添加し、冷凍機油1〜4を調製した。冷凍機油1〜4の各種性状を表1に示す。
[基油〕
基油1:2−エチルヘキサン酸および3,5,5−トリメチルヘキサン酸の混合脂肪酸(混合比(モル比):50/50)とペンタエリスリトールとのエステル。炭素/酸素モル比:4.8
基油2:n−ペンタン酸、n−ヘプタン酸、3,5,5−トリメチルヘキサン酸の混合脂肪酸(混合比(モル比):40/40/20)とペンタエリスリトールとのエステル。炭素/酸素モル比:3.3
基油3:エチルビニルエーテルとイソブチルビニルエーテルの共重合体(エチルビニルエーテル/イソブチルビニルエーテル=7/1(モル比)。重量平均分子量:910、炭素/酸素モル比:4.3
基油4:ポリプロピレングリコ−ルの両末端をメチルエーテル化した化合物。重量平均分子量:1100、炭素/酸素モル比:2.9
基油5:ポリオキシエチレングリコールとポリオキシプロピレングリコールの共重合体であって、片末端をメチルエーテル化した化合物。重量平均分子量:1700、炭素/酸素モル比:2.7
実施例1〜11および比較例1〜9においては、それぞれ上記の冷凍機油1〜4のいずれかと、表2〜4に示す冷媒とを組み合わせた冷凍機用作動流体組成物について、以下に示す評価試験を実施した。なお、後述するように、冷凍機用作動流体組成物における冷媒と冷凍機油との質量比は、試験ごとに変更した。
比較例には、GWP値、燃焼性、熱力学特性から新冷媒として有力候補であるHFC−32、HFO−1234yfを用いた。
[冷媒]
HFC−161:モノフルオロエタン(GWP:約100)
HFC−134a:1,1,1,2−テトラフルオロエタン(GWP:1300)
HFC−32:ジフルオロメタン(GWP:675)
HFO−1234yf:2,3,3,3−テトラフルオロプロペン(GWP:4)
混合冷媒A:HFC−161/HFC−134a=85/15(質量比、GWP:280)
混合冷媒B:HFC−161/HFC−32/R744=60/20/20(質量比、GWP:195)
混合冷媒C:HFC−161/HFO−1234yf=60/40(質量比、GWP:62)
JIS−K−2211「冷凍機油」の「冷媒との相溶性試験方法」に準拠し、混合冷媒を含む上記冷媒のそれぞれ18gに対して冷凍機油を2g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2〜4に示す。表中、「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100ppm以下に調整した冷凍機油(初期色相L0.5)1gと、上記の各種冷媒1gと、触媒(鉄、銅、アルミの各線)とをガラス管に封入した後、鉄製の保護管に入れ175℃に加熱して1週間保持し試験した。試験後に、冷凍機油の色相および触媒の色変化を評価した。色相は、ASTMD156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。光沢なし、黒化の場合は冷凍機油と冷媒の混合液体、つまり作動流体が劣化しているといえる。得られた結果を表2〜4に示す。
Claims (5)
- モノフルオロエタン、ならびに、下記一般式(A)で示される化合物および二酸化炭素から選ばれる少なくとも1種を含有する冷媒と、
ポリオールエステルおよびポリアルキレングリコール化合物から選ばれる少なくとも1種を基油として含有し、該基油の炭素/酸素モル比が2.5以上5.8以下である冷凍機油と、
を含有し、
前記冷媒の地球温暖化係数が300以下である、冷凍機用作動流体組成物。
CpHqFr (A)
[式中、pは1〜4の整数を示し、qは1〜10の整数を示し、rは0〜5の整数を示す。] - 前記冷媒が、前記一般式(A)で示される化合物として、ジフルオロメタン、1,1−ジフルオロエタン、1,1,1−トリフルオロエタン、1,1,1,2−テトラフルオロエタン、ペンタフルオロエタン、1,3,3,3−テトラフルオロプロペン、2,3,3,3−テトラフルオロプロペン、プロパン(R290)およびイソブタン(R600a)から選ばれる少なくとも1種を含有する、請求項1に記載の冷凍機用作動流体組成物。
- 前記冷媒と前記冷凍機油の質量比が90:10〜30:70である、請求項1又は2に記載の冷凍機用作動流体組成物。
- 前記基油が炭素/酸素モル比が2.5以上5.8以下のポリオールエステルを含有し、該ポリオールエステルが、炭素数4〜9の脂肪酸と炭素数4〜12の多価アルコールとから合成されるポリオールエステルである、請求項1〜3のいずれか一項に記載の冷凍機用作動流体組成物。
- 前記基油が炭素/酸素モル比が2.5以上5.8以下のポリアルキレングリコール化合物を含有し、該ポリアルキレングリコール化合物が、プロピレンオキサイドの単独重合鎖またはプロピレンオキサイドとエチレンオキサイドの共重合鎖を有し、その両末端の少なくとも一方がエーテル結合で封鎖された化合物である、請求項1〜4のいずれか一項に記載の冷凍機用作動流体組成物。
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JPWO2016056392A1 (ja) * | 2014-10-09 | 2017-07-20 | Jxtgエネルギー株式会社 | 冷凍機油及び冷凍機用作動流体組成物 |
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EP2832834A1 (en) | 2015-02-04 |
KR20140142265A (ko) | 2014-12-11 |
CN104169405B (zh) | 2017-10-27 |
KR101879567B1 (ko) | 2018-07-19 |
CN104169405A (zh) | 2014-11-26 |
EP2832834A4 (en) | 2015-04-22 |
WO2013147045A1 (ja) | 2013-10-03 |
IN2014DN07563A (ja) | 2015-04-24 |
US20150041705A1 (en) | 2015-02-12 |
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