CN108138067B - 冷冻机油、冷冻机用组合物、冷冻机和冷冻机油的选择方法 - Google Patents
冷冻机油、冷冻机用组合物、冷冻机和冷冻机油的选择方法 Download PDFInfo
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- CN108138067B CN108138067B CN201680058420.2A CN201680058420A CN108138067B CN 108138067 B CN108138067 B CN 108138067B CN 201680058420 A CN201680058420 A CN 201680058420A CN 108138067 B CN108138067 B CN 108138067B
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- 230000001590 oxidative effect Effects 0.000 description 1
- 125000006353 oxyethylene group Chemical group 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- GTLACDSXYULKMZ-UHFFFAOYSA-N pentafluoroethane Chemical compound FC(F)C(F)(F)F GTLACDSXYULKMZ-UHFFFAOYSA-N 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
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- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
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- 239000010726 refrigerant oil Substances 0.000 description 1
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- 229920005989 resin Polymers 0.000 description 1
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- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
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- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
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Abstract
本发明提供热稳定性和氧化稳定性优异的冷冻机油。冷冻机油，其包含选自聚乙烯基醚类、聚氧亚烷基二醇类和多元醇酯类中的至少一种化合物，按照ASTM D1209‑05得到的Hazen色数为0~10。
Description
技术领域
本发明涉及冷冻机油、冷冻机用组合物、冷冻机和冷冻机油的选择方法。
背景技术
一般来说，冷冻机至少由压缩机、凝缩器、膨胀机构(膨胀阀等)、蒸发器、干燥器等构成，形成制冷剂与润滑油(冷冻机油)的混合液体在该密闭体系内循环的结构。
用于冷冻机的制冷剂广泛使用氯氟烃等含氯化合物，但存在破坏臭氧层等环境污染的担忧，因此，逐渐替代为不含氯的氢氟烃(HFC)、二氧化碳等天然系制冷剂。
作为含氯的氟利昂制冷剂用冷冻机油，使用矿物油、烷基苯等合成烃油。但是，这些油相对于替代氟利昂制冷剂的相容性低，因此难以充分发挥出作为冷冻机油的性能。
因此，作为近年来的冷冻机油，广泛使用聚乙烯基醚类、聚氧亚烷基二醇类和多元醇酯类等(例如参照专利文献1)。
现有技术文献
专利文献
专利文献1：日本特开2012-97638号公报。
发明内容
发明要解决的问题
近年来，随着机器的紧凑化等，推进了减少机器内的冷冻机油的使用量，冷冻机油的使用条件变得严苛，对冷冻机油要求现有以上的高品质。例如，由于压缩机滑动部处的摩擦热，有可能导致局部被暴露在高温条件下的冷冻机油发生热分解、所生成的分解物腐蚀金属部件或者对树脂材料造成不良影响。因此，对冷冻机油要求现有以上的高稳定性。
包含选自聚乙烯基醚类、聚氧亚烷基二醇类和多元醇酯类中的化合物的冷冻机油有时热稳定性和氧化稳定性不充分。但是，专利文献1中针对该问题未进行任何研究。
本发明是鉴于上述问题点而进行的，其课题在于，提供热稳定性和氧化稳定性优异的冷冻机油。
用于解决问题的方法
本发明人进行了深入研究，结果发现合成时的聚乙烯基醚类、聚氧亚烷基二醇类和多元醇酯类的颜色与热稳定性和氧化稳定性的关联，从而完成了本发明。
本发明提供下述的(1)~(4)。
(1)冷冻机油，其包含选自聚乙烯基醚类、聚氧亚烷基二醇类和多元醇酯类中的至少一种化合物，按照ASTM D1209-05得到的Hazen色数为0~10。
(2)冷冻机用组合物，其包含前述(1)的冷冻机油和制冷剂。
(3)冷冻机，其含有前述(1)所述的冷冻机油或前述(2)所述的冷冻机用组合物。
(4)冷冻机油的选择方法，其中，测定冷冻机油的按照ASTM D1209-05得到的Hazen色数，选择Hazen色数满足0~10的条件的冷冻机油作为冷冻机油，所述冷冻机油包含选自聚乙烯基醚类、聚氧亚烷基二醇类和多元醇酯类中的至少一种化合物。
发明的效果
根据本发明，能够提供热稳定性和氧化稳定性优异的冷冻机油、冷冻机用组合物和冷冻机。此外，根据本发明，可简易地选择热稳定性和氧化稳定性优异的冷冻机油。
具体实施方式
以下，说明本发明的实施方式。
<冷冻机油>
本实施方式的冷冻机油是包含选自聚乙烯基醚类、聚氧亚烷基二醇类和多元醇酯类中的至少一种化合物，且按照ASTM D1209-05得到的Hazen色数为0~10。
包含选自聚乙烯基醚类、聚氧亚烷基二醇类和多元醇酯类中的化合物的油(以下有时称为“油X”)的热稳定性和氧化稳定性有时不充分。以往，未充分研究油X的热稳定性和氧化稳定性不充分的原因。
本发明人进行了深入研究的结果发现：在油X之中，按照ASTM D1209-05得到的Hazen色数(APHA色)为0~10的油能够使热稳定性和氧化稳定性达到良好。具体而言，在油X之中，Hazen色数为0~10的油能够在高温环境下抑制油的变质，因此，能够抑制油的酸值的上升、油的变色、金属的腐蚀等。另一方面，在油X之中，Hazen色数超过10的油无法使热稳定性和氧化稳定性达到良好。
可以认为：在油X之中，Hazen色数超过10的油无法使热稳定性和氧化稳定性达到良好的理由在于，“在聚乙烯基醚类、聚氧亚烷基二醇类和多元醇酯类的合成过程中生成副产物时，因副产物而发生着色”、“据信，着色源自副产物中包含的不饱和基团、羧基、酮基、醛基和醇基等，通过在分子内存在多个这些基团，未配对电子发生共振，从而着色”、“副产物容易因热等而变质，因此，如果油中包含副产物，则因副产物变质而产生油的酸值的上升、油的变色、金属的腐蚀等”。换言之，油X的Hazen色数为0~10是指油中的副产物的比例少，据信，副产物的比例少会有助于油的热稳定性和氧化稳定性。
可推测：Hazen色数为0~10的油中的副产物的比例为小于1质量%的程度。
从热稳定性和氧化稳定性的观点出发，油X的Hazen色数优选为0。应予说明，Hazen色数为0还包括通过基于ASTM D1209-05的测定方法的检测限以下的情况。
[聚乙烯基醚类(PVE)]
聚乙烯基醚类(PVE)为具有源自乙烯基醚的结构单元的聚合物，具体而言，可以举出具有下述通式(A-1)所示结构单元的化合物。PVE可以使用一种或两种以上。
[化学式1]
前述通式(A-1)中的R1a、R2a和R3a各自独立地表示氢原子或碳原子数为1~8的烃基，它们可以彼此相同也可以不同。在此，作为烃基，具体而言，可以举出甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、各种戊基、各种己基、各种庚基、各种辛基等烷基；环戊基、环己基、各种甲基环己基、各种乙基环己基、各种二甲基环己基等环烷基；苯基、各种甲基苯基、各种乙基苯基、各种二甲基苯基等芳基；苄基、各种苯基乙基、各种甲基苄基等芳基烷基，优选为烷基。
此外，R1a、R2a和R3a更优选是氢原子或碳原子数为3以下的烷基，最优选均为氢原子。
R4a表示碳原子数为2~10的二价烃基，在此，作为碳原子数为2~10的二价烃基，具体而言，有亚乙基、苯基亚乙基、1,2-亚丙基、2-苯基-1,2-亚丙基、1,3-亚丙基、各种亚丁基、各种亚戊基、各种亚己基、各种亚庚基、各种亚辛基、各种亚壬基、各种亚癸基等二价的脂肪族烃基；在环己烷、甲基环己烷、乙基环己烷、二甲基环己烷、丙基环己烷等脂环式烃上具有2个键合部位的脂环式烃基；各种亚苯基、各种甲基亚苯基、各种乙基亚苯基、各种二甲基亚苯基、各种亚萘基等二价的芳族烃基；在甲苯、乙基苯等烷基芳族烃的烷基部分和芳族部分上分别具有一价键合部位的烷基芳族烃基；在二甲苯、二乙基苯等多烷基芳族烃的烷基部分上具有键合部位的烷基芳族烃基等。这些之中，更优选碳原子数为2~4的脂肪族烃基。此外，多个R4aO可以相同也可以不同。此外，通式(A-1)中的r表示重复单元数，其平均值优选为0~10、更优选为0~5、进一步优选为0~2。
进一步，通式(A-1)中的R5a表示碳原子数为1~10的烃基，该烃基具体而言，表示甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、各种戊基、各种己基、各种庚基、各种辛基、各种壬基、各种癸基等烷基；环戊基、环己基、各种甲基环己基、各种乙基环己基、各种丙基环己基、各种二甲基环己基等环烷基；苯基、各种甲基苯基、各种乙基苯基、各种二甲基苯基、各种丙基苯基、各种三甲基苯基、各种丁基苯基、各种萘基等芳基；苄基、各种苯基乙基、各种甲基苄基、各种苯基丙基、各种苯基丁基等芳基烷基。
其中，优选碳原子数为1~8的烃基、更优选碳原子数为1~6的烷基、进一步优选碳原子数为1~3的烷基。应予说明，烷基可以为直链状、支链状、环状中的任一者。
前述具有通式(A-1)所示结构单元的化合物之中，优选为包含R1a、R2a和R3a均为氢原子、r为0、且R5a为乙基或甲基的结构单元的化合物。更具体而言，优选为包含50质量%以上、更优选包含70质量%以上、进一步优选包含80质量%以上的R1a、R2a和R3a均为氢原子、r为0、且R5a为乙基或甲基的结构单元的化合物。
作为这样的具体化合物的名称，可以举出聚乙基聚丁基乙烯基醚、聚乙基乙烯基醚、聚甲基乙烯基醚。
PVE具有前述通式(A-1)所示的结构单元，其重复单元数根据目标运动粘度来适当选择即可。此外，PVE可通过一种下述通式(A-2)所示的乙烯基醚系单体的均聚、或者两种以上的下述通式(A-2)所示的乙烯基醚系单体的共聚来合成。
应予说明，通过常规的方法合成时，所得PVE的Hazen色数会超过10。因此，优选在常规的合成反应结束后进行加氢反应，直至Hazen色数达到10以下为止。可以认为：通过加氢反应，副产物中的不饱和基团、羧基、酮基、醛基和醇基等被氢化，热稳定性和氧化稳定性提高。
加氢反应的条件因常规的合成反应结束后的Hazen色数而异，因此无法一概而论，优选为氢气压力为0.1~10MPa(优选为1~6MPa)、反应温度为10~250℃(优选为50~200℃)的条件。此外，加氢反应时，作为催化剂，优选使用镍系催化剂、铂系催化剂、钯系催化剂、钌系催化剂等金属催化剂、将这些金属催化剂担载于氧化铝、硅藻土等上而得到的催化剂、兰尼型催化剂等。后述的PAG、POE的加氢反应也是相同的条件。
[化学式2]
(式中，R1a、R2a、R3a、R4a和R5a和r与前述相同)。
作为该乙烯基醚系单体，有与前述具有通式(A-1)所示结构单元的化合物对应的各种单体，可以举出例如乙烯基甲基醚、乙烯基乙基醚、乙烯基正丙基醚、乙烯基异丙基醚、乙烯基正丁基醚、乙烯基异丁基醚、乙烯基仲丁基醚、乙烯基叔丁基醚、乙烯基正戊基醚、乙烯基正己基醚、乙烯基-2-甲氧基乙基醚、乙烯基-2-乙氧基乙基醚、乙烯基-2-甲氧基-1-甲基乙基醚、乙烯基-2-甲氧基丙基醚、乙烯基-3,6-二氧杂庚基醚、乙烯基-3,6,9-三氧杂癸基醚、乙烯基-1,4-二甲基-3,6-二氧杂庚基醚、乙烯基-1,4,7-三甲基-3,6,9-三氧杂癸基醚、乙烯基-2,6-二氧杂-4-庚基醚、乙烯基-2,6,9-三氧杂-4-癸基醚、1-甲氧基丙烯、1-乙氧基丙烯、1-正丙氧基丙烯、1-异丙氧基丙烯、1-正丁氧基丙烯、1-异丁氧基丙烯、1-仲丁氧基丙烯、1-叔丁氧基丙烯、2-甲氧基丙烯、2-乙氧基丙烯、2-正丙氧基丙烯、2-异丙氧基丙烯、2-正丁氧基丙烯、2-异丁氧基丙烯、2-仲丁氧基丙烯、2-叔丁氧基丙烯、1-甲氧基-1-丁烯、1-乙氧基-1-丁烯、1-正丙氧基-1-丁烯、1-异丙氧基-1-丁烯、1-正丁氧基-1-丁烯、1-异丁氧基-1-丁烯、1-仲丁氧基-1-丁烯、1-叔丁氧基-1-丁烯、2-甲氧基-1-丁烯、2-乙氧基-1-丁烯、2-正丙氧基-1-丁烯、2-异丙氧基-1-丁烯、2-正丁氧基-1-丁烯、2-异丁氧基-1-丁烯、2-仲丁氧基-1-丁烯、2-叔丁氧基-1-丁烯、2-甲氧基-2-丁烯、2-乙氧基-2-丁烯、2-正丙氧基-2-丁烯、2-异丙氧基-2-丁烯、2-正丁氧基-2-丁烯、2-异丁氧基-2-丁烯、2-仲丁氧基-2-丁烯、2-叔丁氧基-2-丁烯等。这些乙烯基醚系单体可通过公知的方法进行制造。
PVE可以为具有除了源自乙烯基醚的结构单元之外的结构单元的共聚物。作为所述共聚物，可以举出具有源自乙烯基醚的结构单元(A)和源自聚(氧)亚烷基二醇或其单醚的结构单元(B)的结构的共聚物。
应予说明，聚(氧)亚烷基二醇是指聚亚烷基二醇和聚氧亚烷基二醇这两者。
[聚氧亚烷基二醇类(PAG)]
作为聚氧亚烷基二醇类(PAG)，可以举出下述通式(B-1)所示的化合物。PAG可以使用一种或两种以上。
R1b[-(OR2b)m-OR3b]n (B-1)
(式中，R1b表示氢原子、碳原子数为1~10的烃基、碳原子数为2~10的酰基、具有2~6个键合部的碳原子数为1~10的烃基、或碳原子数为1~10的含氧烃基；R2b表示碳原子数为2~4的亚烷基；R3b表示氢原子、碳原子数为1~10的烃基、或碳原子数为2~10的酰基、或碳原子数为1~10的含氧烃基；n表示1~6的整数；m表示使m×n的平均值达到6~80的数)。
前述通式(B-1)中，R1b和R3b各自中的碳原子数为1~10的烃基可以为直链状、支链状、环状中的任一者。该烃基优选为烷基，作为其具体例，可以举出甲基、乙基、正丙基、异丙基、各种丁基、各种戊基、各种己基、各种庚基、各种辛基、各种壬基、各种癸基、环戊基、环己基等。通过使前述烃基的碳原子数为10以下，其与制冷剂的相容性变得良好。从这样的观点出发，烃基的碳原子数更优选为1~4、进一步优选为1~2、更进一步优选为1。
此外，R1b和R3b各自中的碳原子数为2~10的酰基所具有的烃基部分可以为直链状、支链状、环状中的任一者。该酰基的烃基部分优选为烷基，作为其具体例，可以举出能够选作上述R1b和R3b的烷基之中的碳原子数为1~9的基团。通过使该酰基的碳原子数为10以下，其与制冷剂的相容性变得良好。优选酰基的碳原子数为2~4。
R1b和R3b均为烃基或酰基时，R1b与R3b可以相同，也可以彼此不同。
R1b为具有2~6个键合部位的碳原子数为1~10的烃基时，该烃基可以为链状，也可以为环状。作为具有2个键合部位的烃基，优选为脂肪族烃基，可以举出例如亚乙基、亚丙基、亚丁基、亚戊基、亚己基、亚庚基、亚辛基、亚壬基、亚癸基、亚环戊基、亚环己基等。作为其它的烃基，可以举出从联苯酚、双酚F、双酚A等双酚类中去除羟基而得到的残基。此外，作为具有3~6个键合部位的烃基，优选为脂肪族烃基，可以举出例如从三羟甲基丙烷、甘油、季戊四醇、山梨糖醇、1,2,3-三羟基环己烷、1,3,5-三羟基环己烷等多元醇中去除羟基而得到的残基。
通过使该脂肪族烃基的碳原子数为10以下，其与制冷剂的相容性变得良好。该脂肪族烃基的碳原子数优选为2~6。
进一步，作为R1b和R3b各自中的碳原子数为1~10的含氧烃基，可以举出具有醚键的链状脂肪族基团、环状脂肪族基团(例如四氢糠基)等。
前述R1b和R3b中的至少一者优选为烷基、更优选碳原子数为1~4的烷基、进一步优选碳原子数为1~2的烷基、更进一步优选碳原子数为1的烷基。此外，优选前述R1b和R3b均满足前述条件。
前述通式(B-1)中的R2b是碳原子数为2~4的亚烷基，作为重复单元的氧亚烷基，可以举出氧亚乙基、氧亚丙基、氧亚丁基。1分子中的氧亚烷基可以相同，也可以包含2种以上的氧亚烷基，优选在1分子中至少包含氧亚丙基单元，更优选在氧亚烷基单元中包含50摩尔%以上的氧亚丙基单元，更优选包含70摩尔%以上的氧亚丙基单元。
前述通式(B-1)中的n为1~6的整数，其根据R1b的键合部位的数量来确定。例如，R1b为烷基、酰基时，n为1；R1b为具有2、3、4、5和6个键合部位的脂肪族烃基时，n分别为2、3、4、5和6。
此外，m为使m×n的平均值达到6~80的数。通过使该平均值达到80以下，与制冷剂的相容性变得良好。但是，m×n的平均值优选以基础油的粘度达到期望范围的方式进行适当设定。
此外，n优选为1~3的整数、更优选为1。n为1时，优选R1b和R3b中的任一者为烷基，更优选两者为烷基。同样地，n为2以上时，优选1分子内存在的多个R3b中的任一者为烷基，更优选均为烷基。
应予说明，n为2以上时，1分子中的多个R3b可以相同，也可以不同。
前述通式(B-1)所示的化合物可以在末端具有羟基。应予说明，末端具有羟基时，优选末端羟基相对于全部末端基团的比例为50%以下。
作为这样的具体化合物的名称，可以举出聚丙二醇聚乙二醇二甲基醚、聚丙二醇二甲基醚。
PAG可通过例如使醇类与环氧乙烷、环氧丙烷等环氧烷烃进行加成聚合，将末端羟基进行醚化来合成。
应予说明，通过常规的方法合成时，所得PAG的Hazen色数会超过10。因此，优选在常规的合成反应结束后进行加氢反应，直至Hazen色数达到10以下为止。可以认为：通过加氢反应，副产物中的不饱和基团、羧基、酮基、醛基和醇基等被氢化，热稳定性和氧化稳定性提高。
<多元醇酯类(POE)>
作为多元醇酯类(POE)，优选使用二元醇或具有3~20个左右的羟基的多元醇与碳原子数为1~24左右的脂肪酸形成的酯。POE可以使用一种或两种以上。
应予说明，本实施方式中，简称为“酯”时，是指全酯。
作为二元醇，可以举出例如乙二醇、1,3-丙二醇、丙二醇、1,4-丁二醇、1,2-丁二醇、2-甲基-1,3-丙二醇、1,5-戊二醇、新戊二醇、1,6-己二醇、2-乙基-2-甲基-1,3-丙二醇、1,7-庚二醇、2-甲基-2-丙基-1,3-丙二醇、2,2-二乙基-1,3-丙二醇、1,8-辛二醇、1,9-壬二醇、1,10-癸二醇、1,11-十一烷二醇、1,12-十二烷二醇等。
作为多元醇，可以举出例如三羟甲基乙烷、三羟甲基丙烷、三羟甲基丁烷、二(三羟甲基丙烷)、三(三羟甲基丙烷)、季戊四醇、二季戊四醇、三季戊四醇、甘油、聚甘油(甘油的2~20聚体)、1,3,5-戊三醇、山梨糖醇、脱水山梨糖醇、山梨糖醇甘油缩合物、核糖醇(adonitol)、阿拉伯糖醇、木糖醇、甘露醇等多元醇；木糖、阿拉伯糖、核糖、鼠李糖、葡萄糖、果糖、半乳糖、甘露糖、山梨糖、纤维二糖、麦芽糖、异麦芽糖、海藻糖、蔗糖、棉子糖、龙胆三糖、松三糖(Melezitose)等糖类；以及它们的部分醚化物和甲基葡糖苷(配糖体)等。
二元醇和多元醇的碳原子数没有特别限定，碳原子数优选为3~15、更优选为4~12、进一步优选为5~10。
这些二元醇和多元醇之中，优选为新戊二醇、三羟甲基乙烷、三羟甲基丙烷、三羟甲基丁烷、二(三羟甲基丙烷)、三(三羟甲基丙烷)、季戊四醇、二季戊四醇和三季戊四醇(以下有时称为“多元醇组A”)。
脂肪酸没有特别限定，通常可以使用碳原子数为1~24的脂肪酸。碳原子数为1~24的脂肪酸之中，从润滑性的观点出发，优选碳原子数为3以上的脂肪酸，更优选碳原子数为4以上的脂肪酸，进一步优选碳原子数为5以上的脂肪酸。此外，从与制冷剂的相容性的观点出发，优选碳原子数为18以下的脂肪酸，更优选碳原子数为12以下的脂肪酸，进一步优选碳原子数为9以下的脂肪酸。
此外，可以是直链状脂肪酸、支链状脂肪酸中的任一者，从润滑性的观点出发，优选为直链状脂肪酸，从水解稳定性的观点出发，优选为支链状脂肪酸。进一步，可以为饱和脂肪酸、不饱和脂肪酸中的任一者。
作为脂肪酸，可以举出例如异丁酸、戊酸、己酸、庚酸、辛酸、壬酸、癸酸、十一烷酸、十二烷酸、十三烷酸、十四烷酸、十五烷酸、十六烷酸、十七烷酸、十八烷酸、十九烷酸、二十烷酸、油酸等直链或支链的脂肪酸；或者α碳原子为季碳原子的所谓新酸等。
这些脂肪酸之中，优选为异丁酸、戊酸(正戊酸)、己酸(正己酸)、庚酸(正庚酸)、辛酸(正辛酸)、壬酸(正壬酸)、癸酸(正癸酸)、油酸(顺式-9-十八碳烯酸)、异戊酸(3-甲基丁酸)、2-甲基丁酸、2-乙基丁酸、2-甲基戊酸、2-乙基戊酸、2-甲基己酸、2-乙基己酸和3,5,5-三甲基己酸(以下有时称为“脂肪酸组A”)。
作为POE，优选为选自前述多元醇组A中的至少一种与选自前述脂肪酸组A中的至少一种形成的酯。
作为这样的具体化合物的名称，可以举出新戊二醇与2-甲基戊酸形成的二酯、三羟甲基丙烷与3,5,5-三甲基己酸形成的三酯、季戊四醇与2-乙基丁酸形成的四酯、季戊四醇与正戊酸和2-乙基己酸形成的四酯、季戊四醇与2-甲基己酸和3,5,5-三甲基己酸形成的四酯、季戊四醇与2-乙基己酸形成的四酯、季戊四醇与3,5,5-三甲基己酸形成的四酯、二季戊四醇与2-甲基丁酸形成的六酯、二季戊四醇与2-甲基戊酸形成的六酯、二季戊四醇与2-乙基己酸形成的六酯。
POE可通过二元醇或多元醇与脂肪酸的酯化反应来合成。
应予说明，通过常规的方法进行合成时，所得POE的Hazen色数会超过10。因此，优选在常规的合成反应结束后进行加氢反应，直至Hazen色数达到10以下为止。可以认为：通过加氢反应，副产物中的不饱和基团、羧基、酮基、醛基和醇基等被氢化，热稳定性和氧化稳定性提高。
PVE、PAG和POE的聚苯乙烯换算的重均分子量(Mw)优选低于5000，更优选为200~3000、进一步优选为250~2000。
作为本实施方式中的冷冻机油，优选包含选自PVE、PAG和POE中的至少一种化合物作为主成分。在此，作为主成分而包含是指在冷冻机油中以50质量%以上的比例包含该化合物。
冷冻机油中的该化合物含量更优选为70质量%以上、进一步优选为90质量%以上、更进一步优选为95质量%以上、特别优选为97质量%以上。
此外，在冷冻机油中包含选自PVE、PAG和POE中的至少一种化合物作为主成分时，构成该主成分的化合物优选为PVE、PAG和POE中的任意单一种类。例如，优选仅由选自PVE中的化合物来构成该主成分。或者，优选仅由选自PAG中的化合物来构成该主成分。或者，优选仅由选自POE中的化合物来构成该主成分。
冷冻机油在不损害本发明效果的范围内可以含有除了PVE、PAG和POE之外的合成油(例如多元醇中的羟基未全部被酯化而残留的偏酯等)、矿物油。
[冷冻机油的物性]
从润滑不良的抑制与动力损失的平衡的观点出发，冷冻机油的40℃的运动粘度优选为3~200mm2/s、更优选为3~150mm2/s。
从润滑不良的抑制与动力损失的平衡的观点出发，冷冻机油的100℃的运动粘度优选为1~40mm2/s、更优选为1~25mm2/s。
冷冻机油的粘度指数优选为50以上、更优选为60以上。
40℃的运动粘度、100℃的运动粘度和粘度指数可按照JIS K2283:2000进行测定。
从稳定性的观点出发，冷冻机油的酸值优选为0.05mgKOH/g以下、更优选为0.03mgKOH/g以下、进一步优选为0.01mgKOH/g以下。酸值可按照JIS K2501:2003的“指示剂滴定法”进行测定。
从稳定性的观点出发，冷冻机油的羟值优选为10mgKOH/g以下、更优选为5mgKOH/g以下、进一步优选为3mgKOH/g以下。羟值可按照JIS K0070:1992的“中和滴定法”进行测定。
冷冻机油的体积电阻率优选为2.0×108Ω・m以上、更优选为5.0×108Ω・m以上、进一步优选为1.0×109Ω・m以上。如果体积电阻率达到2.0×108Ω・m以上，则冷冻机油物的绝缘性提高，即使如电动汽车空调等那样地驱动源为电动的情况下，也难以产生实用上会成为问题的1mA以上的漏电流。
冷冻机油的水分含量优选低于1000ppm、更优选为300ppm以下、进一步优选为150ppm以下。通过降低水分含量，冷冻机油难以发生水解，冷冻机油的稳定性提高，能够提供长期良好的润滑性能。
<冷冻机用组合物>
本实施方式的冷冻机用组合物含有上述本实施方式的冷冻机油、以及制冷剂。
[制冷剂]
作为制冷剂，可以举出氟代烃制冷剂、氟代醚化合物制冷剂、氟代醇化合物制冷剂、氟代酮化合物制冷剂、天然制冷剂等。制冷剂可以为一种，也可以混合使用两种以上。
作为氟代烃制冷剂，可以举出饱和氟代烃制冷剂、不饱和氟代烃制冷剂。
作为饱和氟代烃制冷剂，可以举出二氟甲烷(R32)、氟乙烷(R161)、1,1,1,2,2-五氟乙烷(R125)、1,1,1,2-四氟乙烷(R134a)、1,1,2,2-四氟乙烷(R134)、1,1,1-三氟乙烷(R143a)、1,1,2-三氟乙烷(R143)、1,1-二氟乙烷(R152a)等。其中，优选为二氟甲烷(R32)。
作为不饱和氟代烃制冷剂，可以举出例如1,1,2-三氟乙烯(R1123)、1,2,3,3,3-五氟丙烯(R1225ye)、2,3,3,3-四氟丙烯(R1234yf)、1,3,3,3-四氟丙烯(R1234ze)、1,2,3,3-四氟丙烯(R1234ye)、(Z)-1,1,1,4,4,4-六氟-2-丁烯(反式-R1336mzz)等。其中，优选为1,1,2-三氟乙烯(R1123)、2,3,3,3-四氟丙烯(R1234yf)。
作为氟代醚化合物，可以举出例如六氟二甲基醚、五氟二甲基醚、双(二氟甲基)醚、氟甲基三氟甲基醚、三氟甲基甲基醚、二氟甲氧基五氟乙烷、1-三氟甲氧基-1,2,2,2-四氟乙烷、全氟氧杂环丁烷、全氟-1,3-二氧杂环戊烷、五氟氧杂环丁烷的各种异构体、四氟氧杂环丁烷的各种异构体等。
作为氟代醇化合物，可以举出例如单氟甲醇、二氟甲醇、三氟甲醇、二氟乙醇的各种异构体、三氟乙醇的各种异构体、四氟乙醇的各种异构体、五氟乙醇、二氟丙醇的各种异构体、三氟丙醇的各种异构体、六氟丙二醇等氟代丙二醇、以及与该氟代丙二醇对应的氟代三亚甲基二醇等。
作为氟代酮化合物，可以举出例如六氟二甲基甲酮、五氟二甲基甲酮、双(二氟甲基)甲酮、氟甲基三氟甲基甲酮、三氟甲基甲基甲酮、全氟甲乙酮、三氟甲基-1,1,2,2-四氟乙基甲酮等。
作为天然系制冷剂，可以举出二氧化碳(碳酸气体)、丙烷、正丁烷、异丁烷、2-甲基丁烷、正戊烷、环戊烷异丁烷、正丁烷等烃；氨。其中，优选为二氧化碳(碳酸气体)。
前述制冷剂之中，从冷冻机油的稳定性的观点出发，优选为选自二氟甲烷(R32)和2,3,3,3-四氟丙烯(R1234yf)中的至少一种，特别优选为二氟甲烷(R32)单独的制冷剂和2,3,3,3-四氟丙烯(R1234yf)单独的制冷剂、二氟甲烷(R32)与2,3,3,3-四氟丙烯(R1234yf)的混合制冷剂。
冷冻机油与制冷剂的含量比(冷冻机油/制冷剂)以质量比计优选为1/99~99/1、更优选为5/95~60/40。
[添加剂]
冷冻机油和冷冻机用组合物中可以含有选自包括抗氧化剂、极压剂、酸捕捉剂、氧捕捉剂和铜惰化剂在内的添加剂中的至少一种。各添加剂的含量相对于冷冻机油总量和冷冻机用组合物总量通常为0.01~5质量%、优选为0.05~3质量%。
作为抗氧化剂，可以举出2,6-二叔丁基-4-甲基苯酚、2,6-二叔丁基-4-乙基苯酚、2,2'-亚甲基双(4-甲基-6-叔丁基苯酚)、2,6-二叔丁基对甲酚等酚系抗氧化剂；苯基-α-萘基胺、N,N'-二苯基对苯二胺等胺系抗氧化剂等。其中，优选为2,6-二叔丁基对甲酚。
作为极压剂，可以举出磷酸酯、酸式磷酸酯、亚磷酸酯、酸式亚磷酸酯和它们的胺盐等磷系极压剂；硫化油脂、硫化脂肪酸、硫化酯等硫系极压剂；碳原子数为3~60的脂肪酸金属盐等。其中，优选为磷酸三甲苯酯。
作为酸捕捉剂，可以举出苯基缩水甘油醚、烷基缩水甘油醚、亚烷基二醇缩水甘油醚、缩水甘油酯、环氧环己烯、环氧α-烯烃、环氧化大豆油等环氧化合物。其中，优选为2-乙基己基缩水甘油醚。
作为氧捕捉剂，可以举出4,4'-硫代双(3-甲基-6-叔丁基苯酚)、二苯硫醚、二辛基二苯硫醚、二烷基二苯并噻吩(dialkylphenylene sulfide)、苯并噻吩、二苯并噻吩、吩噻嗪、苯并噻喃、噻喃、噻蒽、二苯并噻喃、二硫化二苯撑(diphenylene disulfide)等含硫芳族化合物、各种烯烃、二烯、三烯等脂肪族不饱和化合物、具有双键的萜烯类等。
作为铜惰化剂，可以举出N-[N,N'-二烷基(碳原子数为3~12的烷基)氨基甲基]三唑等。
[冷冻机用组合物的物性]
冷冻机用组合物的运动粘度、粘度指数、酸值、羟值、体积电阻率和水分含量的适合范围与上述冷冻机油的适合范围相同。
<冷冻机>
本实施方式的冷冻机含有上述本实施方式的冷冻机油或者上述本实施方式的冷冻机用组合物。
本实施方式的冷冻机优选为压缩型冷冻机。此外，压缩型冷冻机压缩机更优选具有：具备凝缩器、膨胀机构(膨胀阀等)和蒸发器的冷冻循环；或者具备压缩机、凝缩器、膨胀机构、干燥器和蒸发器的冷冻循环。
冷冻机油或冷冻机用组合物可用于对例如压缩机等中设置的滑动部分进行润滑。
应予说明，滑动部分没有特别限定，滑动部分中的任意者优选包含铁等金属，优选在金属-金属之间进行滑动。
冷冻机可用于例如空气调节器、燃气热泵(GHP)、空调、冰箱、自动售货机、陈列柜等的冷冻系统、供热水系统和暖气系统等。
<冷冻机油的选择方法>
本实施方式的冷冻机的选择方法中，测定冷冻机油的按照ASTM D1209-05得到的Hazen色数，选择Hazen色数满足0~10的条件的冷冻机油作为冷冻机油，所述冷冻机油包含选自聚乙烯基醚类、聚氧亚烷基二醇类和多元醇酯类中的至少一种化合物。
以往，针对包含选自聚乙烯基醚类、聚氧亚烷基二醇类和多元醇酯类中的化合物的油(油X)的热稳定性和氧化稳定性变得不充分的原因未作充分研究。因此，油X在出货前必须实施可靠性试验。
根据本实施方式的冷冻机油的选择方法，能够通过按照ASTM D1209-05测定Hazen色数这一简单方法来选择热稳定性和氧化稳定性优异的油X，不需要实施可靠性试验，能够大幅提高作业效率。
Hazen色数的判定条件优选为0~10，更优选为0。应予说明，Hazen色数为0还包括通过基于ASTM D1209-05的测定方法的检测限以下的情况。
实施例
以下，通过实施例，更具体地说明本发明，但本发明不因这些例子而受到任何限定。
1. 测定
针对实施例和比较例的冷冻机油和冷冻机用组合物，进行下述测定。将结果示于表2~5。
1-1. Hazen色数的测定
按照ASTM D1209-05，算出实施例和比较例的冷冻机油的Hazen色数。将结果示于表2。
1-2. 40℃运动粘度、100℃运动粘度、粘度指数
按照JIS K2283:2000，测定实施例和比较例的冷冻机油的40℃运动粘度、100℃运动粘度和粘度指数。将结果示于表2。
1-3. 重均分子量(Mw)
使用凝胶渗透色谱(GPC)，测定实施例和比较例的冷冻机油的重均分子量(Mw)。GPC中，作为柱而使用2根东曹株式会社制造的TSKgel SuperMultiporeHZ-M，将四氢呋喃作为洗脱液，检测器使用折射率检测器来进行测定，以聚苯乙烯作为标准试样，求出重均分子量(Mw)。将结果示于表2。
1-4. 酸值
按照JIS K2501:2003的“指示剂滴定法”，测定实施例和比较例的冷冻机油的酸值。将结果示于表2。应予说明，后述的稳定性试验1~3的酸值也通过指示剂滴定法进行测定。
2. 冷冻机油的合成
2-1. POE 1~20的合成
相对于表1-1中记载的醇类的羟基1当量，以表1-1中记载的羧酸的羧基达到1.2当量的方式投入至烧瓶内并混合，在氮气气氛下，在常压、230℃下进行加热并反应15小时来进行酯化，从而得到组合物A。从组合物A中去除未反应的羧酸，添加活性白土来进行吸附处理，通过过滤器去除活性白土，将酸值调整至0.03以下，从而得到POE 11~20。
进一步，对POE 11~20，进行加氢反应(反应温度为100℃、氢气压力为3.5MPa、催化剂：镍硅藻土)，直至Hazen色数达到表2的值为止，从而得到POE 1~10。
[表1-1]
2-2. PAG 1~4的合成
将100份甲醇投入气密容器并进行氮气置换，与5份氢氧化钾一同压入表1-2中记载的环氧烷烃，在110~140℃下聚合至达到表2中记载的重均分子量为止，从而得到聚亚烷基二醇单甲基醚。相对于聚亚烷基二醇单甲基醚1摩尔，添加1.05摩尔的甲醇钠，在130℃下、氮气中、2.7kPa的压力下进行脱甲醇。使其反应4小时后，耗时3小时压入相对于聚亚烷基二醇单甲基醚1摩尔为0.54摩尔的二氯甲烷，进一步熟化2小时，在120~140℃下进行搅拌，从而得到组合物B。将组合物B与作为过滤助剂的钠沸石(Radiolite)0.2份一同过滤，将酸值调整至0.03以下，从而得到PAG 3~4。
进一步，对PAG 3~4进行加氢反应(反应温度：140℃、氢气压力：3.5MPa、催化剂：镍硅藻土)，直至Hazen色数达到表1的值为止，从而得到PAG 1~2。
[表1-2]
2-3. PVE 1~6的合成
向安装有搅拌机的玻璃制1L烧瓶中，分别添加甲苯106g、乙醇24.3g和三氟化硼二乙基醚络合物0.2g。此外，向另行准备的锥形瓶中添加表1-3所记载的乙烯基醚系单体400g。
并且，启动搅拌机，通过泵以5mL/min向前述1L烧瓶的经搅拌的体系内供给了前述锥形瓶内的乙烯基醚系单体46g时，将泵暂停。
确认前述1L烧瓶的体系内的温度上升后，再次启动泵，耗时4小时向该1L烧瓶的经搅拌的体系内供给剩余的乙烯基醚系单体，在供给结束后进一步持续搅拌5分钟，从而得到组合物C。应予说明，在乙烯基醚系单体的供给中，体系内一直持续搅拌，体系内的温度使用水浴控制为25℃。
向组合物C中添加活性白土来进行吸附处理，通过过滤器来去除活性白土，进一步去除未反应的乙烯基醚系单体和溶剂，将酸值调整至0.03以下，从而得到PVE 4~6。
进一步，对PVE4~6进行加氢反应(反应温度为140℃、氢气压力为3.5MPa、催化剂：镍硅藻土)，直至Hazen色数达到表2的值为止，从而得到PVE 1~3。
[表1-3]
[表2]
使用2-1~2-3中合成的冷冻机油，进行下述稳定性试验。
[实施例1-1~1-15]、[比较例1-1~1-15]
<稳定性试验1(密封管试验1)>
向玻璃管中填充表3的冷冻机油4mL、制冷剂(R32)1g、添加剂(相对于冷冻机油100质量份为1质量份的磷酸三甲苯酯、0.5质量份的2,6-二叔丁基对甲酚、1质量份的2-乙基己基缩水甘油醚)、金属催化剂(铁、铜、铝)并封管，在空气压力为6.7kPa、温度为175℃的条件下保持10天。其后，测定玻璃管内的冷冻机用组合物后的酸值，并且目视评价油的外观、铁催化剂的外观。应予说明，将玻璃管内的冷冻机用组合物的水分调整至50ppm以下。将结果示于表3。
[表3]
[实施例2-1~2-6]、[比较例2-1~2-6]
<稳定性试验2(密封管试验2)>
将冷冻机油变更为表4的冷冻机油，将制冷剂变更为R32与R1234yf的1:1混合物(质量比)，将2-乙基己基缩水甘油醚的添加量变更为相对于冷冻机油100质量份为1.5质量份，除此之外，以与稳定性试验1同样的方式，评价冷冻机用组合物的酸值、油外观、铁催化剂外观。将结果示于表4。
[表4]
[实施例3-1~3-6]、[比较例3-1~3-6]
<稳定性试验3(密封管试验3)>
将冷冻机油变更为表5的冷冻机油，将制冷剂变更为R1234yf，将2-乙基己基缩水甘油醚的添加量变更为相对于冷冻机油100质量份为3质量份，除此之外，以与稳定性试验1同样的方式，评价冷冻机用组合物的酸值、油外观、铁催化剂外观。将结果示于表5。
[表5]
根据表1~3的结果可以确认：包含选自聚乙烯基醚类、聚氧亚烷基二醇类和多元醇酯类中的至少一种化合物、且按照ASTM D1209-05得到的Hazen色数为0~10的冷冻机油能够在高温环境下抑制油的变质，因此能够抑制油的酸值的上升、油的变色、金属的腐蚀等，热稳定性和氧化稳定性优异。
Claims (7)
1.冷冻机用组合物，其包含冷冻机油、以及不饱和氟代烃制冷剂，
所述冷冻机油包含选自聚乙烯基醚类、聚氧亚烷基二醇类和多元醇酯类中的至少一种化合物，按照ASTM D1209-05得到的Hazen色数为0~10，
在冷冻机油中以50质量%以上的比例包含所述选自聚乙烯基醚类、聚氧亚烷基二醇类和多元醇酯类中的至少一种化合物。
2.根据权利要求1所述的冷冻机用组合物，其中，所述冷冻机油的40℃的运动粘度为3~200mm2/s。
3.根据权利要求1或2所述的冷冻机用组合物，其中，所述冷冻机油的酸值为0.05mgKOH/g以下。
4.根据权利要求1所述的冷冻机用组合物，其中，所述制冷剂为2,3,3,3-四氟丙烯。
5.根据权利要求1或4所述的冷冻机用组合物，其还包含选自包括抗氧化剂、极压剂、酸捕捉剂、氧捕捉剂和铜惰化剂的添加剂中的至少一种。
6.冷冻机，其含有权利要求1~5中任一项所述的冷冻机用组合物。
7.冷冻机油的选择方法，其中，测定冷冻机油的按照ASTM D1209-05得到的Hazen色数，选择Hazen色数满足0~10的条件的冷冻机油作为冷冻机油，所述冷冻机油包含选自聚乙烯基醚类、聚氧亚烷基二醇类和多元醇酯类中的至少一种化合物，在冷冻机油中以50质量%以上的比例包含所述选自聚乙烯基醚类、聚氧亚烷基二醇类和多元醇酯类中的至少一种化合物。
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| CN106062159B (zh) * | 2014-02-20 | 2019-04-16 | Ａｇｃ株式会社 | 热循环系统用组合物以及热循环系统 |
| JP2018100349A (ja) | 2016-12-20 | 2018-06-28 | 出光興産株式会社 | 冷凍機油、及び冷凍機用組成物 |
| WO2019156126A1 (ja) | 2018-02-07 | 2019-08-15 | 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 |
| CN111699237B (zh) * | 2018-02-07 | 2022-08-09 | 引能仕株式会社 | 冷冻机油及冷冻机用工作流体组合物 |
| WO2020166272A1 (ja) * | 2019-02-14 | 2020-08-20 | 出光興産株式会社 | 冷凍機用組成物 |
| EP4036194A4 (en) * | 2019-09-27 | 2023-07-26 | Idemitsu Kosan Co.,Ltd. | LUBRICATING OIL COMPOSITION FOR REFRIGERATORS |
| KR20230161518A (ko) * | 2021-07-20 | 2023-11-27 | 미쓰이 가가쿠 가부시키가이샤 | 윤활유용 점도 조정제 및 작동유용 윤활유 조성물 |
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| EP3360950A1 (en) | 2018-08-15 |
| US20180282649A1 (en) | 2018-10-04 |
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