JP6050360B2 - 潤滑油基油、冷凍機油及び冷凍機用作動流体組成物 - Google Patents
潤滑油基油、冷凍機油及び冷凍機用作動流体組成物 Download PDFInfo
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- JP6050360B2 JP6050360B2 JP2014527005A JP2014527005A JP6050360B2 JP 6050360 B2 JP6050360 B2 JP 6050360B2 JP 2014527005 A JP2014527005 A JP 2014527005A JP 2014527005 A JP2014527005 A JP 2014527005A JP 6050360 B2 JP6050360 B2 JP 6050360B2
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- refrigerating machine
- machine oil
- component
- oil according
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- VNXBKJFUJUWOCW-UHFFFAOYSA-N methylcyclopropane Chemical compound CC1CC1 VNXBKJFUJUWOCW-UHFFFAOYSA-N 0.000 description 1
- PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 description 1
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- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 description 1
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- 230000002265 prevention Effects 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
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- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
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- 238000010998 test method Methods 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
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Classifications
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- C09K2205/126—Unsaturated fluorinated hydrocarbons
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- C09K2205/00—Aspects relating to compounds used in compression type refrigeration systems
- C09K2205/22—All components of a mixture being fluoro compounds
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Description
[1]2〜4個のヒドロキシル基を有する多価アルコールから選ばれる少なくとも1種である第一の成分と、炭素数6〜12の多塩基酸から選ばれる少なくとも1種である第二の成分と、炭素数4〜18の一価アルコール及び炭素数2〜12の一価脂肪酸から選ばれる少なくとも1種である第三の成分と、から合成されるエステルを含有する潤滑油基油。
[2]前記第一の成分がネオペンチルグリコール、トリメチロールプロパン及びペンタエリスリトールから選ばれる少なくとも1種を含む、[1]に記載の潤滑油基油。
[3]前記第一の成分が、ネオペンチルグリコール、トリメチロールプロパン及びペンタエリスリトールから選ばれる少なくとも1種である第一のアルコールと、ネオペンチルグリコール以外の炭素数2〜10の二価アルコールから選ばれる少なくとも1種である第二のアルコールと、を含む、[1]又は[2]に記載の潤滑油基油。
[4]前記第一の成分がネオペンチルグリコール及びトリメチロールプロパンから選ばれる少なくとも1種を含む、[1]〜[3]のいずれか一項に記載の潤滑油基油。
[5]前記第二の成分がアジピン酸及びセバシン酸から選ばれる少なくとも1種を含む、[1]〜[4]のいずれか一項に記載の潤滑油基油。
[6]前記第一の成分がブタンジオールを含む、[1]〜[5]のいずれか一項に記載の潤滑油基油。
[7]前記第三の成分が炭素数8〜10の一価アルコールから選ばれる少なくとも1種を含む、[1]〜[6]のいずれか一項に記載の潤滑油基油。
[8][1]〜[7]のいずれか一項に記載の潤滑油基油を含有する冷凍機油。
[9]ハイドロフルオロカーボン、ハイドロフルオロオレフィン、炭素数2〜4の炭化水素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共に用いられる、[8]に記載の冷凍機油。
[10]地球温暖化係数が1000以下の冷媒と共に用いられる、[8]又は[9]に記載の冷凍機油。
[11]地球温暖化係数が700以下の冷媒と共に用いられる、[8]〜[10]のいずれか一項に記載の冷凍機油。
[12]ジフルオロメタンを含有する冷媒と共に用いられる、[8]〜[11]のいずれか一項に記載の冷凍機油。
[13]プロパンまたはイソブタンを含有する冷媒と共に用いられる、請求項8〜12のいずれか一項に記載の冷凍機油。
[14]ハイドロフルオロプロペンの少なくとも一種を含有する冷媒と共に用いられる、[8]〜[12]のいずれか一項に記載の冷凍機油。
[15][1]〜[7]のいずれか一項に記載の潤滑油基油を含有する冷凍機油と、ハイドロフルオロカーボン、ハイドロフルオロオレフィン、炭素数2〜4の炭化水素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、を含有する冷凍機用作動流体組成物。
本発明の第1実施形態に係る潤滑油基油は、以下に示す第一の成分と第二の成分と第三の成分とから合成されるエステル(以下、場合により「本実施形態に係るコンプレックスエステル」ともいう)を含有する。
第一の成分:2〜4個のヒドロキシル基を有する多価アルコールから選ばれる少なくとも1種、
第二の成分:炭素数6〜12の多塩基酸から選ばれる少なくとも1種、
第三の成分:炭素数4〜18の一価アルコール及び炭素数2〜12の一価脂肪酸から選ばれる少なくとも1種。
(A)ネオペンチルグリコール、トリメチロールプロパン及びペンタエリスリトールから選ばれる少なくとも1種である第一のアルコールと、
(B)ネオペンチルグリコール以外の炭素数2〜10の二価アルコールから選ばれる少なくとも1種である第二のアルコールと、
(C)炭素数6〜12の多塩基酸から選ばれる少なくとも1種の多塩基酸と、
(D)炭素数4〜18のモノアルコールから選ばれる少なくとも1種である第三のアルコールと、
から合成されるエステルを挙げることができる。
まず、(A)成分と(B)成分と(C)成分とを反応させて第一のエステル中間体を得る。このとき、得られる第一のエステル中間体において、(B)成分に由来するカルボン酸基(−COOH)が存在するように、(A)成分と(B)成分と(C)成分とのモル比を調整する。
次に、上記第一のエステル中間体と(D)成分とを反応させて、第一のエステル中間体のカルボン酸基(−COOH)を(D)成分(炭素数が4〜18の一価アルコール)でエステル化して目的のエステル(本実施形態に係るコンプレックスエステル)を得る。
上記の各工程におけるエステル化反応は、常法に従って行うことができ、また、エステル化反応の反応条件は適宜選択することができる。
本発明の第2実施形態に係る冷凍機油は、ネオペンチルグリコール、トリメチロールプロパン及びペンタエリスリトールから選ばれる少なくとも1種である第一のアルコールと、炭素数6〜12の多塩基酸から選ばれる少なくとも1種である多塩基酸と、ネオペンチルグリコール以外の炭素数2〜10の二価アルコールから選ばれる少なくとも1種である第二のアルコールと、炭素数4〜18の一価アルコールから選ばれる少なくとも1種である第三のアルコールとから合成されるエステル(以下、場合により「本実施形態に係るコンプレックスエステル」ともいう)を含有する。なお、当該コンプレックスエステルは、上記第1実施形態に係るコンプレックスエステルと同様であるため、ここでは重複する説明を省略する。
現在は1,1,1,2−テトラフルオロエタン(HFC−134a、R134a)が冷蔵庫及びカーエアコン用として、ジフルオロメタン(HFC−32、R32)とペンタフルオロエタン(HFC−125、R125)の質量比1/1の混合冷媒であるR410Aがルームエアコン用として広く使用されている。これらの冷媒を使用した冷凍機用の冷凍機油の基油としては、エステル(但し、本実施形態に係るコンプレックスを含まない)、ポリエーテル、特にはポリオールエステル、ポリアルキレングリコール、ポリビニルエーテルが適していると考えられていた。これは、冷凍・空調機器の冷媒循環サイクルにおいて、コンプレッサを潤滑する冷凍機油が冷媒とともにサイクル内を循環するため、冷凍機油と冷媒の相溶性が要求されるからである。冷凍機油と冷媒が相溶しないと、コンプレッサから吐出された冷凍機油がサイクル内に滞留しやすくなり、その結果、コンプレッサ内の油量が低下し潤滑不良による摩耗や、キャピラリ等の膨張機構を閉塞するといった問題を生じる。
ネオペンチルグリコールと1,4−ブタンジオールとアジピン酸とを、ネオペンチルグリコール/1,4−ブタンジオール/アジピン酸=1/0.3/2.4(モル比)で反応させてエステル中間体を得た。このエステル中間体に、さらに3,5,5−トリメチルヘキサノールを、ネオペンチルグリコール/3,5,5−トリメチルヘキサノール=1/2.5(モル比)で、触媒、溶媒を使用せずに反応させ、残存したアルコールを蒸留で除去した。そして、最終工程で吸着処理(白土処理)を行って微量の不純物を除去し、エステル(40℃における動粘度67.8mm2/s、粘度指数145、流動点−50℃、以下、エステル(A−1)という)を得た。
ネオペンチルグリコールと1,3−ブタンジオールとセバシン酸とを、ネオペンチルグリコール/1,3−ブタンジオール/セバシン酸=1/0.2/2.4(モル比)で反応させてエステル中間体を得た。このエステル中間体に、さらにノルマルオクタノールを、ネオペンチルグリコール/ノルマルオクタノール=1/2.6(モル比)となるように触媒、溶媒を使用せずに反応させ、残存したアルコールを蒸留で除去した。そして、最終工程で吸着処理(白土処理)を行って微量の不純物を除去し、エステル(40℃における動粘度59.0mm2/s、粘度指数158、流動点−50℃、以下「エステル(A−2)」という)を得た。
トリメチロールプロパンと1,4−ブタンジオールとアジピン酸とを、トリメチロールプロパン/1,4−ブタンジオール/アジピン酸=1/0.2/2.4(モル比)で反応させてエステル中間体を得た。このエステル中間体に、さらにノルマルヘプタノールを、トリメチロールプロパン/ノルマルヘプタノール=1/1.6(モル比)となるように触媒、溶媒を使用せずに反応させ、残存したアルコールを蒸留で除去した。そして、最終工程で吸着処理(白土処理)を行って微量の不純物を除去し、エステル(40℃における動粘度75.8mm2/s、粘度指数148、以下、「エステル(A−3)」という)を得た。
トリメチロールプロパンとアジピン酸とを、トリメチロールプロパン/アジピン酸=1/2.4(モル比)で反応させて、エステル中間体を得た。このエステル中間体に、さらに2−エチルヘキサノールを、トリメチロールプロパン/2−エチルヘキサノール=1/1.9(モル比)となるように反応させ、残存したアルコールを蒸留で除去した。そして、最終工程で吸着処理(白土処理)を行って微量の不純物を除去し、エステル(40℃における動粘度68.8mm2/s、粘度指数120、以下、「エステル(A−4)」という、)を得た。
ネオペンチルグリコールとアジピン酸とを、ネオペンチルグリコール/アジピン酸=1/0.8(モル比)で反応させて、エステル中間体を得た。このエステル中間体に、さらに3,5,5−トリメチルヘキサン酸を、ネオペンチルグリコール/3,5,5−トリメチルヘキサン酸=1/0.5(モル比)となるように反応させ、残存した脂肪酸を蒸留で除去した。そして、最終工程で吸着処理(白土処理)を行って微量の不純物を除去し、エステル(動粘度71.5mm2/s、粘度指数114、以下、「エステル(A−5)」という、)を得た。
ネオペンチルグリコールと1,4−ブタンジオールとアジピン酸とを、ネオペンチルグリコール/1,4−ブタンジオール/アジピン酸=1/0.1/1.2(モル比)で反応させてエステル中間体を得た。このエステル中間体に、さらに3,5,5−トリメチルヘキサノールを、ネオペンチルグリコール/3,5,5−トリメチルヘキサノール=1/0.3(モル比)で、触媒、溶媒を使用せずに反応させ、残存したアルコールを蒸留で除去した。そして、最終工程で吸着処理(白土処理)を行って微量の不純物を除去し、エステル(40℃における動粘度275.9mm2/s、粘度指数117、流動点−35℃、以下、エステル(A−6)という)を得た。
ネオペンチルグリコールと1,4−ブタンジオールとアジピン酸とを、ネオペンチルグリコール/1,4−ブタンジオール/アジピン酸=1/0.4/3.1(モル比)で反応させてエステル中間体を得た。このエステル中間体に、さらに3,5,5−トリメチルヘキサノールを、ネオペンチルグリコール/3,5,5−トリメチルヘキサノール=1/3.5(モル比)で、触媒、溶媒を使用せずに反応させ、残存したアルコールを蒸留で除去した。そして、最終工程で吸着処理(白土処理)を行って微量の不純物を除去し、エステル(40℃における動粘度32.2mm2/s、粘度指数161、流動点−55℃、以下、エステル(A−7)という)を得た。
ネオペンチルグリコールとアジピン酸とを、ネオペンチルグリコール/アジピン酸=1/0.8(モル比)で反応させてエステル中間体を得た。このエステル中間体に、さらに3,5,5−トリメチルヘキサン酸を、ネオペンチルグリコール/3,5,5−トリメチルヘキサン酸=1/0.3(モル比)で、触媒、溶媒を使用せずに反応させ、残存したアルコールを蒸留で除去した。そして、最終工程で吸着処理(白土処理)を行って微量の不純物を除去し、エステル(40℃における動粘度300mm2/s、粘度指数114、流動点−35℃、以下、エステル(A−8)という)を得た。
実施例9〜67においては、上記のエステル(A−1)〜(A−8)のいずれかを基油とし、これに酸化防止剤であるジ−tert.ブチル−p−クレゾール(DBPC)0.1質量%(冷凍機油全量基準)を配合して、冷凍機油を調製した。
比較例1〜45においては、それぞれ以下に示す(b−1)〜(b−3)、(c−1)、(c−2)のいずれかを基油とし、これに酸化防止剤であるジ−tert.ブチル−p−クレゾール(DBPC)0.1質量%(冷凍機油全量基準)を配合して、冷凍機油を調製した。
実施例9〜67及び比較例1〜45で用いた基油の種類は表1〜16に示したとおりである。
<基油>
(b−1)ペンタエリスリトールと、2−メチルプロパン酸と3,5,5−トリメチルヘキサン酸が質量比で1:1の混合酸とのエステル(40℃における動粘度69.4mm2/s、粘度指数95、流動点−45℃)
(b−2)ジペンタエリスリトールと、ノルマルブタン酸と3,5,5−トリメチルヘキサン酸が質量比で7:3の混合酸とのエステル(40℃における動粘度68.1mm2/s、粘度指数90)
(b−3)トリメチロールプロパンとオレイン酸とのエステル(40℃における動粘度50.3mm2/s、粘度指数176)
(b−4)ペンタエリスリトールとペンタン酸と3,5,5−トリメチルヘキサン酸とのエステル(40℃における動粘度31.4mm2/s、粘度指数118、流動点−55℃未満)
(c−1)ポリα−オレフィン(PAO)(40℃における動粘度34.0mm2/s、粘度指数170、流動点−55℃未満)
(c−2)ポリα−オレフィン(PAO)(40℃における動粘度68.0mm2/s、粘度指数94、流動点−55℃未満)
基油(b−1)〜(b−4)、(c−1)、(c−2)の動粘度及び粘度指数はJIS K2283に準拠し測定、計算した。また、これらの基油のうち(b−1)〜(b−4)については、製造の最終工程で吸着処理(白土処理)を行い、微量の不純物を除去した。
実コンプレッサと類似の冷媒雰囲気にできる、神鋼造機(株)製の高圧雰囲気摩擦試験機(回転ベーン材と固定ディスク材との回転しゅう動方式)を用いて、潤滑性試験を行った。試験条件は、冷媒の種類ごとに下記の潤滑性試験−(1)〜(4)のいずれかとした。
潤滑性試験−(1):冷媒にR32を使用し、試験容器内圧力は3.1MPa
潤滑性試験−(2):冷媒にHFO−1234yfを使用し、試験容器内圧力は1.6MPa
潤滑性試験−(3):冷媒にR410A(質量比でR32/R125=1/1)を使用し、試験容器内圧力は3.1MPa
潤滑性試験−(4):n−ヘキサン(n−C6)を油に対して容積で20%配合して試験した(R290等の炭化水素冷媒は安全面での不安があり、代替として使用)。圧力は常圧より若干高くなった程度である。
潤滑性試験−(5):冷媒にR404A(質量比でHFC−125/HFC−134a/HFC−143a=44/4/52)を使用し、試験容器内圧力は1.6MPa
潤滑性試験−(6):冷媒にR407C(質量比でHFC−32/HFC−125/HFC−134a=23/25/52)を使用し、試験容器内圧力は1.6MPa
潤滑性試験−(7):冷媒にR134aを使用し、試験容器内圧力は1.6MPa
潤滑性試験−(8):冷媒にCO2を使用し、試験容器内圧力は1.6MPa
上記以外の試験条件は、潤滑性試験−(1)〜(8)のいずれも、油量600ml、試験温度110℃、回転数500rpm、負荷荷重80kgf、試験時間1時間で共通である。また、ベーン材としてはSKH−51、ディスク材としてはFC250を用いた点も共通である。
なお、耐摩耗の評価は、ディスク材の摩耗量が極めて少ないことから、ベーン材の摩耗深さによって行った。得られた結果を表1〜16に示す。
含有水分量を100ppmに調整した冷凍機油90g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×50mm)と以下の冷媒:
実施例9〜16及び比較例1〜6:R32、
実施例17〜24及び比較例7〜12:HFO−1234yf、
実施例25〜30及び比較例13〜16:R410A、
実施例31〜35及び比較例17〜21:n−ヘキサン、
実施例36〜43及び比較例22〜27:R404A、
実施例44〜51及び比較例28〜33:R407C、
実施例52〜59及び比較例34〜39:R134a、
実施例60〜67及び比較例40〜45:CO2
の10gを封入した後、175℃に加熱し、100時間後の試料油の外観観察と酸価の測定を行った。得られた結果を表1〜16に示す。
なお、安定性試験前の試料油(新油)の酸価は、すべて0.01mgKOH/gであった。
実施例9〜59の冷凍機油は、耐摩耗性が良好で、かつ、安定性も良いことがわかる。
Claims (13)
- 2〜4個のヒドロキシル基を有する多価アルコールから選ばれる少なくとも1種である第一の成分と、炭素数6〜12の多塩基酸から選ばれる少なくとも1種である第二の成分と、炭素数4〜18の一価アルコール及び炭素数2〜12の一価脂肪酸から選ばれる少なくとも1種である第三の成分と、から合成されるエステル
を含有し、
前記第一の成分が、
ネオペンチルグリコール、トリメチロールプロパン及びペンタエリスリトールから選ばれる少なくとも1種である第一のアルコールと、
ネオペンチルグリコール以外の炭素数2〜10の二価アルコールから選ばれる少なくとも1種である第二のアルコールと、
を含む、潤滑油基油。 - 前記第一の成分がネオペンチルグリコール及びトリメチロールプロパンから選ばれる少なくとも1種を含む、請求項1に記載の潤滑油基油。
- 前記第二の成分がアジピン酸及びセバシン酸から選ばれる少なくとも1種を含む、請求項1又は2に記載の潤滑油基油。
- 前記第一の成分がブタンジオールを含む、請求項1〜3のいずれか一項に記載の潤滑油基油。
- 前記第三の成分が炭素数8〜10の一価アルコールから選ばれる少なくとも1種を含む、請求項1〜4のいずれか一項に記載の潤滑油基油。
- 請求項1〜5のいずれか一項に記載の潤滑油基油を含有する冷凍機油。
- ハイドロフルオロカーボン、ハイドロフルオロオレフィン、炭素数2〜4の炭化水素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共に用いられる、請求項6に記載の冷凍機油。
- 地球温暖化係数が1000以下の冷媒と共に用いられる、請求項6又は7に記載の冷凍機油。
- 地球温暖化係数が700以下の冷媒と共に用いられる、請求項6〜8のいずれか一項に記載の冷凍機油。
- ジフルオロメタンを含有する冷媒と共に用いられる、請求項6〜9のいずれか一項に記載の冷凍機油。
- プロパンまたはイソブタンを含有する冷媒と共に用いられる、請求項6〜10のいずれか一項に記載の冷凍機油。
- ハイドロフルオロプロペンの少なくとも一種を含有する冷媒と共に用いられる、請求項6〜11のいずれか一項に記載の冷凍機油。
- 請求項1〜5のいずれか一項に記載の潤滑油基油を含有する冷凍機油と、
ハイドロフルオロカーボン、ハイドロフルオロオレフィン、炭素数2〜4の炭化水素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、
を含有する冷凍機用作動流体組成物。
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BR112015020797A2 (pt) * | 2013-03-25 | 2017-07-18 | Jx Nippon Oil & Energy Corp | composição de fluido de trabalho para refrigerador |
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CN106536693B (zh) * | 2014-10-03 | 2019-11-22 | 捷客斯能源株式会社 | 润滑油基础油和冷冻机油 |
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