JP6736050B2 - 耐摩耗添加剤、冷凍機油及び冷凍機用作動流体組成物 - Google Patents
耐摩耗添加剤、冷凍機油及び冷凍機用作動流体組成物 Download PDFInfo
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- JP6736050B2 JP6736050B2 JP2016531258A JP2016531258A JP6736050B2 JP 6736050 B2 JP6736050 B2 JP 6736050B2 JP 2016531258 A JP2016531258 A JP 2016531258A JP 2016531258 A JP2016531258 A JP 2016531258A JP 6736050 B2 JP6736050 B2 JP 6736050B2
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- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
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- 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
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
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- 239000002184 metal Substances 0.000 description 1
- 239000006078 metal deactivator Substances 0.000 description 1
- VNXBKJFUJUWOCW-UHFFFAOYSA-N methylcyclopropane Chemical compound CC1CC1 VNXBKJFUJUWOCW-UHFFFAOYSA-N 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 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
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 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
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- 229940055577 oleyl alcohol Drugs 0.000 description 1
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- 239000012188 paraffin wax Substances 0.000 description 1
- GTLACDSXYULKMZ-UHFFFAOYSA-N pentafluoroethane Chemical compound FC(F)C(F)(F)F GTLACDSXYULKMZ-UHFFFAOYSA-N 0.000 description 1
- UWJJYHHHVWZFEP-UHFFFAOYSA-N pentane-1,1-diol Chemical compound CCCCC(O)O UWJJYHHHVWZFEP-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920001083 polybutene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920013636 polyphenyl ether polymer Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920001289 polyvinyl ether Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- QZZGJDVWLFXDLK-UHFFFAOYSA-N tetracosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCC(O)=O QZZGJDVWLFXDLK-UHFFFAOYSA-N 0.000 description 1
- OFHCXWMZXQBQMH-UHFFFAOYSA-N trifluoro(trifluoromethylsulfanyl)methane Chemical compound FC(F)(F)SC(F)(F)F OFHCXWMZXQBQMH-UHFFFAOYSA-N 0.000 description 1
- VPAYJEUHKVESSD-UHFFFAOYSA-N trifluoroiodomethane Chemical compound FC(F)(F)I VPAYJEUHKVESSD-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M155/00—Lubricating compositions characterised by the additive being a macromolecular compound containing atoms of elements not provided for in groups C10M143/00 - C10M153/00
- C10M155/02—Monomer containing silicon
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- 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
- C10M169/04—Mixtures of base-materials and additives
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
- C10M105/32—Esters
- C10M105/38—Esters of polyhydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
- C10M105/32—Esters
- C10M105/42—Complex esters, i.e. compounds containing at least three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compound: monohydroxy compounds, polyhydroxy compounds, monocarboxylic acids, polycarboxylic acids and hydroxy carboxylic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
Description
(a)多価アルコールと多塩基酸とのモル比を調整して、多塩基酸のカルボキシル基の一部がエステル化されずに残存するエステル中間体を合成し、次いでその残存するカルボキシル基を一価アルコールでエステル化する方法
(b)多価アルコールと多塩基酸とのモル比を調整して、多価アルコールの水酸基の一部がエステル化されずに残存するエステル中間体を合成し、次いでその残存する水酸基を一価脂肪酸でエステル化する方法
[エステル(A−1)の製造]
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、残存した未反応物を蒸留で除去した。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℃)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、残存した未反応物を蒸留で除去した。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、流動点−55℃)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、残存した未反応物を蒸留で除去した。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、流動点−55℃)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、残存した未反応物を蒸留で除去した。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℃)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、残存した未反応物を蒸留で除去した。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℃)を得た。
(b−1)ペンタエリスリトールと、2−メチルプロパン酸及び3,5,5−トリメチルヘキサン酸の混合酸(2−メチルプロパン酸:3,5,5−トリメチルヘキサン酸=1:1(質量比))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、ノルマルブタン酸及び3,5,5−トリメチルヘキサン酸の混合酸(ノルマルブタン酸:3,5,5−トリメチルヘキサン酸=7:3(質量比))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、流動点−45℃)
(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)
(b−5)ペンタエリスリトールと2−エチルヘキサン酸と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68.3mm2/s、粘度指数87、流動点−45℃)
添加剤1:ジメチルポリシロキサン(25℃における動粘度:30000mm2/s)
添加剤2:ジメチルポリシロキサンの主鎖の末端をポリアルキレングリコールで変性した変性シリコーン油
添加剤3:ジメチルポリシロキサンの主鎖の末端をエステルで変性した変性シリコーン油
添加剤4:ジメチルポリシロキサンの側鎖をフルオロポリエーテル基に変性したフッ素化シリコーン油
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、冷媒圧力変動耐摩耗性試験を行った。試験条件は、評価冷媒の種類ごとに下記の耐摩耗性試験−(1)〜(6)の条件のいずれかとした。
耐摩耗性試験−(1):冷媒にR134aを使用し、試験容器内圧力は1.6MPa。
耐摩耗性試験−(2):冷媒にR410Aを使用し、試験容器内圧力は1.6MPa。
耐摩耗性試験−(3):冷媒にR32を使用し、試験容器内圧力は1.6MPa。
耐摩耗性試験−(4):冷媒にHFO−1234yfを使用し、試験容器内圧力は1.6MPa。
耐摩耗性試験−(5):n−ヘキサン(冷凍機油に対して容積で20%配合。R290等の炭化水素冷媒は安全面での不安があるため代替として使用。)、試験容器内圧力は常圧より若干高い圧力。
耐摩耗性試験−(6):冷媒にCO2を使用し、試験容器内圧力は1.6MPa。
Claims (8)
- 多価アルコールと炭素数4〜9の脂肪酸とからなるポリオールエステル、及びコンプレックスエステルからなる群より選ばれる少なくとも1種のみからなる基油と、
ジメチルポリシロキサンであるシリコーン油、ジメチルポリシロキサンの主鎖の末端をポリアルキレングリコールで変性した変性シリコーン油、及びジメチルポリシロキサンの側鎖をフルオロポリエーテル基に変性したフッ素化シリコーン油からなる群より選ばれる少なくとも1種である耐摩耗添加剤と、を含有し、
前記基油の含有量が冷凍機油全量基準で95質量%以上であり、かつ、
前記耐摩耗添加剤の含有量が冷凍機油全量基準で0.1質量ppm以上500質量ppm以下である、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1に記載の冷凍機油。
- 不飽和フッ化炭化水素冷媒を含有する冷媒と共に用いられる、請求項1又は2に記載の冷凍機油。
- 前記基油が前記ポリオールエステルを含有する、請求項1〜3のいずれか一項に記載の冷凍機油。
- 前記基油が、前記コンプレックスエステルとして、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種と、炭素数6〜12の多塩基酸から選ばれる少なくとも1種と、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種とから合成されるコンプレックスエステルを含有する、請求項1〜4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冷凍機油と、冷媒と、を含有する冷凍機用作動流体組成物。
- 前記冷媒がジフルオロメタンを含有する、請求項6に記載の冷凍機用作動流体組成物。
- 前記冷媒が不飽和フッ化炭化水素冷媒を含有する、請求項6又は7に記載の冷凍機用作動流体組成物。
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