WO2020115235A1 - Huile hydraulique ignifuge - Google Patents

Huile hydraulique ignifuge Download PDF

Info

Publication number
WO2020115235A1
WO2020115235A1 PCT/EP2019/083875 EP2019083875W WO2020115235A1 WO 2020115235 A1 WO2020115235 A1 WO 2020115235A1 EP 2019083875 W EP2019083875 W EP 2019083875W WO 2020115235 A1 WO2020115235 A1 WO 2020115235A1
Authority
WO
WIPO (PCT)
Prior art keywords
hydraulic oil
mass
additive
flame
tert
Prior art date
Application number
PCT/EP2019/083875
Other languages
English (en)
Inventor
Hiroshi Kaneko
Mai KITAGAWA
Original Assignee
Shell Internationale Research Maatschappij B.V.
Shell Oil Company
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Shell Internationale Research Maatschappij B.V., Shell Oil Company filed Critical Shell Internationale Research Maatschappij B.V.
Publication of WO2020115235A1 publication Critical patent/WO2020115235A1/fr

Links

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
    • 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/026—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with tertiary alkyl groups
    • 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic acids
    • C10M2207/2815—Esters of (cyclo)aliphatic monocarboxylic acids used as base material
    • 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/283—Esters of polyhydroxy compounds
    • C10M2207/2835—Esters of polyhydroxy compounds used as base material
    • 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/40—Fatty vegetable or animal oils
    • C10M2207/401—Fatty vegetable or animal oils used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • C10N2020/067—Unsaturated Compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • C10N2020/081—Biodegradable compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/10—Inhibition of oxidation, e.g. anti-oxidants

Definitions

  • the present invention relates to a lubricating oil composition, and particularly relates to a flame-retardant hydraulic oil.
  • the hydraulic oil of the above-mentioned equipment does not use a mineral oil-based base oil, but uses a flame- retardant base oil such as one or more fatty acid esters.
  • the performance of a fatty acid ester base oil depends on the composition of the fatty acids constituting the ester.
  • esters formed of saturated fatty acids have
  • esters of saturated fatty acids may be synthesized from petroleum or produced by hydrogenating unsaturated fatty acids contained in natural fats and oils, but the cost is increased. Therefore, ester oils using fatty acids of naturally occurring fats and oils are frequently used because it is advantageous in terms of cost .
  • animal fats and oils have a high content of saturated fatty acids and a low content of unsaturated fatty acids, but in the case of vegetable fats and oils, the content of unsaturated fatty acids is higher than that of animal fats and oils. Therefore, in the case of vegetable fats and oils, oxidation stability further becomes a problem.
  • antioxidants hydraulic oil, phenolic or amine-based antioxidants are used as antioxidants, but there is a problem that
  • the present invention provides a flame-retardant hydraulic oil comprising: a 2 , 6-di-tert-butylphenol as an additive; and a fatty acid ester containing one or more unsaturated bonds as a base oil.
  • An object of the present invention is to obtain a flame-retardant hydraulic oil that can withstand high temperature and high pressure and can be stably used for a long time by obtaining sufficient oxidation stability by the addition of additives in the fatty acid ester oil containing one or more unsaturated bond as a base oil, as described above.
  • Another object of the present invention is to obtain a biodegradable flame-retardant hydraulic oil by making the base oil biodegradable.
  • the inventors proceeded with the examination by conducting various studies on antioxidant additives effective for base oils of fatty acid esters containing unsaturated bonds and found that 2 , 6-di-tert-butylphenol gives very good results. Thus, the present invention was completed based on such findings.
  • the present invention provides a flame- retardant hydraulic oil by adding and including 2,6-di- tert-butylphenol to the fatty acid ester containing an unsaturated bond.
  • This additive, 2 6-di-tert-butylphenol , is effective when it is contained in an amount of more than 0.5 mass% and 6.0 mass% or less by mass based on the total amount of the hydraulic oil.
  • the 2 , 6-di-tert-butylphenol is even more effective when used in combination with tris (2,4-di- tert-butylphenyl ) phosphite as a phosphoric acid ester type antioxidant.
  • the amount of tris (2, 4-di-tert- butylphenyl) phosphite used is more than 0.5 mass% on the basis of the total amount of the hydraulic oil, and preferably 3.0 mass% or less.
  • the hydraulic oil where fatty acid esters containing one or more unsaturated bond are used as the base oil, is flame retardant and has excellent antioxidant performance even when used under conditions of high temperature and
  • the fatty acid ester used for the base oil of the flame-retardant hydraulic oil of the present invention generally can be economically obtained by esterification using fatty acid obtained from natural fats and oils.
  • the fatty acids of these fatty acid esters contain unsaturated bonds.
  • ester examples include hindered esters. Furthermore, among the hindered esters, esters of pentaerythritol and trimethylolpropane are more preferable. Moreover, since these esters have biodegradability that passes any of OECD 301 B, OECD 301 C, OECD 301 F, ASTM D 5864, ASTM D 6731, ISO 14593, and ISO 9439, the hydraulic oil made using said esters can also be used as a biodegradable flame-retardant hydraulic oil .
  • animal fats and oils such as beef tallow, lard and mutton tallow have a relatively small proportion of unsaturated fatty acids, but vegetable fats and oils such as coconut oil and palm oil have a large content of unsaturated fatty acids.
  • linoleic acid is about 6% in beef tallow
  • the content thereof is increased to about 12% in vegetable fats and oils.
  • Examples of the existing esters include those where the beef tallow containing unsaturated fatty acid of 5.8% of linoleic acid, 74.1% of oleic acid, and 6.4% of
  • palmitoleic acid and the rest being saturated fatty acid is used as the raw material.
  • the base oil contains fatty acids derived from natural fats and oils as described above.
  • ester oils containing unsaturated bonds obtained by pure synthesis and hydrogenated products of natural fats and oils may also be used.
  • 6-di-tert-butylphenol is added and used.
  • the 2,6-di- tert-butylphenol is a phenolic substance having the following structure.
  • the 2 , 6-di-tert-butylphenol has a structure similar to that of BHT (butylhydroxytoluene) (2, 6-di-tert-butyl-
  • 6-di-tert-butylphenol has been known as a phenolic substance having a similar structure to BHT, but it has hardly been practically used as an antioxidant, and in the present invention, it was found to have good compatibility with fatty acid esters containing unsaturated bonds.
  • the 2 , 6-di-tert-butylphenol is considered to form a dimer due to the fact that the position 4 of the benzene ring is a hydrogen atom.
  • Such 2 , 6-di-tert-butylphenol is used in an amount of more than 0.5 mass%, and 6.0 mass% or less, based on the total amount of the hydraulic oil, preferably, 1.0 mass% to 5.0 mass%, more preferably 2.0 mass% to 5.0 mass%.
  • the tris (2 , 4-di-tert-butylphenyl ) phosphite is used in an amount of more than 0.5 mass%, and 3.0 mass% or less, based on the total amount of hydraulic oil,
  • the flame-retardant hydraulic oil may contain other additives, if required.
  • additives include rust inhibitors, copper inactivators, antiwear agents, extreme pressure agents, dispersants, metal-based detergents, friction modifiers, corrosion inhibitors, demulsifiers, pour point depressants, antifoaming agents and other various additives. These may be blended alone or in combination of several kinds.
  • the flame-retardant hydraulic oil having biodegradability it can be used as a biodegradable hydraulic oil which does not inhibit biodegradability by appropriately selecting these additives.
  • Base oil Fatty acid ester oil (trimethylol propane ester: Main component is represented in CAS 57675-44-2)
  • the kinematic viscosity at 40°C. is 58.2 mm2/s
  • the kinematic viscosity at 100°C. is 11.3 mm2/s
  • the density at 15°C. is 0.921 g/cm3
  • the flash point is 360°C.
  • the saponification value is 188.0 mg KOH/g
  • derived unsaturated fatty acid linoleic acid 12.2%, oleic acid 77.6%, palmitoleic acid 0.02%, and rest is saturated fatty acid (having biodegradability that passes OECD 301 B) .
  • Additive (3) Benzenepropanoic acid 3,5-bis (1,1-dimethyl- ethyl) -4-hydroxy-C7 to C9 side chain alkyl ester (Irganox L135: manufactured by Chiba Specialty Chemicals)
  • Additive (5) Antirust agent (alkyl naphthalene sulfonic acid calcium salt / carboxylic acid calcium salt complex)
  • Additive (6) Copper inactivator (benzotriazole)
  • Antiwear agent (3- (di-isobutoxy- thiophosphorylsulfanyl ) -2-methyl-propionic acid)
  • Example 1 The following Examples and Comparative Examples were produced .
  • Example 1 The following Examples and Comparative Examples were produced .
  • test equipment and test method were based on JIS K 2514.
  • the catalyst was immersed in the sample and stirred with a stirrer at 135°C for 96 hours to oxidize the sample. It was then subjected to the ISOT test
  • test results are shown in Tables 1 to 3.
  • Table 1 in the case of using 2.0 mass% of 2,6- di-tert-butylphenol (additive 1) in Example 1, the result of the heat resistance test (kinematic viscosity at 40°C after ISOT) was 74.58 mm 2 /s and 100 mm 2 /s or less; and good results were obtained as a heat resistant hydraulic oil.
  • Example 2 3.0 mass% of additive 1 was used and in Example 3, the amount of additive 1 was increased to 5.0 mass%.
  • the results of the heat resistance test were 69.32 mm 2 s and 68.82 mm 2 /s, which were better than Example 1.
  • Example 4 was obtained by adding 1.0 mass% of tris ( 2 , 4-di-tert-butylphenyl ) phosphite (additive 2) to Example 1, and the result of the heat resistance test was 66.78 mm 2 /s, which was better than Example 1 due to the combined use with additive 1.
  • Example 5 and Example 6 were obtained by adding 1.0 mass% of additive 2 to Example 2 and Example 3, respectively. The results of the heat resistance test were 64.15 mm 2 /s in Example 5 and 63.44 mm 2 /s in Example 6.
  • the combined use of 2 , 6-di-tert-butylphenol and ( 2 , 4-di-tert-butylphenyl ) phosphite demonstrated further improvements .
  • Comparative Example 1 of Table 2 the additive 1 was reduced to 0.5 mass%, and the 1.0 mass% of additive 2 was used. Since the amount of the additive 1 added was small, the result of the heat resistance test was poor. In Comparative Example 2, additive 1 was not used and 0.5 mass% of the additive 2 was used, and the heat resistance test showed no satisfactory results. In Comparative Example 1 of Table 2, the additive 1 was reduced to 0.5 mass%, and the 1.0 mass% of additive 2 was used. Since the amount of the additive 1 added was small, the result of the heat resistance test was poor. In Comparative Example 2, additive 1 was not used and 0.5 mass% of the additive 2 was used, and the heat resistance test showed no satisfactory results. In Comparative Example 1 of Table 2, the additive 1 was reduced to 0.5 mass%, and the 1.0 mass% of additive 2 was used. Since the amount of the additive 1 added was small, the result of the heat resistance test was poor. In Comparative Example 2, additive 1 was not used and 0.5 mass% of the additive 2 was used, and the heat resistance test showed no satisfactory results. In Comparative
  • Example 3 and Comparative Example 4 similarly 1.5 mass% and 2.5 mass% of additive 2 were used, respectively. Even when the amount of additive 2 used was increased, the result of the heat resistance test was worse than that of Comparative Example 2.
  • Comparative Example 7 the amount of the additive 2 used was increased to 2.0 mass% with respect to that of Comparative Example 5, but no satisfactory results were obtained because additive 1 was not used. Further, in Comparative Example 8, the amount of the additive 3 used was increased to 3.0 mass% with respect to that of
  • compositions described in Examples 1 to 6 can also be used as biodegradable flame-retardant hydraulic oils .
  • the heat resistance test (*) represents the 40°C. kinematic viscosity after the ISOT test (oxidation stability test) .

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)

Abstract

L'invention concerne une huile hydraulique ignifuge comprenant: un 2,6-di-tert-butylphénol en tant qu'additif; et un ester d'acide gras contenant une ou plusieurs liaisons insaturées en tant qu'huile de base.
PCT/EP2019/083875 2018-12-07 2019-12-05 Huile hydraulique ignifuge WO2020115235A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2018-229510 2018-12-07
JP2018229510A JP7181778B2 (ja) 2018-12-07 2018-12-07 難燃性油圧作動油

Publications (1)

Publication Number Publication Date
WO2020115235A1 true WO2020115235A1 (fr) 2020-06-11

Family

ID=68808380

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2019/083875 WO2020115235A1 (fr) 2018-12-07 2019-12-05 Huile hydraulique ignifuge

Country Status (2)

Country Link
JP (1) JP7181778B2 (fr)
WO (1) WO2020115235A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113831948A (zh) * 2021-09-18 2021-12-24 新乡市瑞丰新材料股份有限公司 一种液压油复合剂及其制备方法

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0721979A2 (fr) * 1995-01-13 1996-07-17 Ciba-Geigy Ag Compositions lubrifiantes stabilisées
US5773391A (en) * 1994-11-15 1998-06-30 The Lubrizol Corporation High oleic polyol esters, compositions and lubricants, functional fluids and greases containing the same
WO2006018403A1 (fr) * 2004-08-18 2006-02-23 Ciba Specialty Chemicals Holding Inc. Compositions d'huile de graissage aux caracteristiques de fonctionnement ameliorees
JP2009161664A (ja) 2008-01-08 2009-07-23 Nippon Oil Corp 難燃性油圧作動油組成物
CN106833843A (zh) * 2017-01-21 2017-06-13 郑州人造金刚石及制品工程技术研究中心有限公司 一种含有纳米钻石烯的变压器用导热油及其制备方法

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3298112B1 (fr) 2015-05-19 2023-05-10 Quaker Chemical Corporation Esters synthétiques dérivés d'acide oléique à haute stabilité

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5773391A (en) * 1994-11-15 1998-06-30 The Lubrizol Corporation High oleic polyol esters, compositions and lubricants, functional fluids and greases containing the same
EP0721979A2 (fr) * 1995-01-13 1996-07-17 Ciba-Geigy Ag Compositions lubrifiantes stabilisées
WO2006018403A1 (fr) * 2004-08-18 2006-02-23 Ciba Specialty Chemicals Holding Inc. Compositions d'huile de graissage aux caracteristiques de fonctionnement ameliorees
JP2009161664A (ja) 2008-01-08 2009-07-23 Nippon Oil Corp 難燃性油圧作動油組成物
CN106833843A (zh) * 2017-01-21 2017-06-13 郑州人造金刚石及制品工程技术研究中心有限公司 一种含有纳米钻石烯的变压器用导热油及其制备方法

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113831948A (zh) * 2021-09-18 2021-12-24 新乡市瑞丰新材料股份有限公司 一种液压油复合剂及其制备方法
CN113831948B (zh) * 2021-09-18 2022-12-09 新乡市瑞丰新材料股份有限公司 一种液压油复合剂及其制备方法

Also Published As

Publication number Publication date
JP2020090630A (ja) 2020-06-11
JP7181778B2 (ja) 2022-12-01

Similar Documents

Publication Publication Date Title
US8557754B2 (en) Composition of biodegradable gear oil
WO2008134179A2 (fr) Composition de mélange lubrifiant
WO2014207235A1 (fr) Compositions de lubrification contenant des composants à base d'isoprène
JP2005314650A (ja) 潤滑油組成物
JP2011102375A (ja) 難燃性油圧作動油組成物
EP3746529A1 (fr) Composition lubrifiante
JP2017515949A (ja) 潤滑油
KR20130038357A (ko) 개선된 증점제 수율을 지니는 리튬 복합체 그리스
JP2024015129A (ja) 低粘度で摩耗防止を提供する潤滑油組成物
CA2859241C (fr) Additif de scellement gonflant renfermant un diester de sorbitol
WO2020115235A1 (fr) Huile hydraulique ignifuge
JP5441480B2 (ja) 潤滑油組成物
JPWO2017217297A1 (ja) 潤滑油基油
WO2019188809A1 (fr) Composition d'huile antirouille et son procédé de production
JP2016180052A (ja) 潤滑油組成物
KR20080014789A (ko) 질화 붕소를 포함하는 고온 생물학적 윤활제 조성물
JP2020143358A (ja) 錆止め油組成物及びその製造方法
JP3639876B2 (ja) 塑性加工用防錆潤滑剤組成物
JP2008138092A (ja) 亜鉛メッキ鋼板用金属加工油組成物
CN112119141B (zh) 往复式压缩机油
JP4315856B2 (ja) 耐冷性液状潤滑油及びその製造方法
JP5496502B2 (ja) 潤滑油組成物
CN107109291B (zh) α-烯烃吸附抑制性润滑剂组合物、吸附抑制方法及吸附抑制剂
JP6974216B2 (ja) 船尾管用潤滑油組成物
JP5529388B2 (ja) 金属加工用圧延油組成物

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 19816660

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 19816660

Country of ref document: EP

Kind code of ref document: A1