GB886978A - Polyphenyl ethers - Google Patents
Polyphenyl ethersInfo
- Publication number
- GB886978A GB886978A GB39285/59A GB3928559A GB886978A GB 886978 A GB886978 A GB 886978A GB 39285/59 A GB39285/59 A GB 39285/59A GB 3928559 A GB3928559 A GB 3928559A GB 886978 A GB886978 A GB 886978A
- Authority
- GB
- United Kingdom
- Prior art keywords
- benzene
- mixture
- polyphenyl
- bis
- phenoxyphenoxy
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- 229920013636 polyphenyl ether polymer Polymers 0.000 title abstract 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 15
- 239000000203 mixture Substances 0.000 abstract 9
- 229920000570 polyether Polymers 0.000 abstract 6
- -1 aromatic carboxylic acids Chemical class 0.000 abstract 5
- 229920006389 polyphenyl polymer Polymers 0.000 abstract 5
- 239000000314 lubricant Substances 0.000 abstract 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 3
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 3
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- BEJQGHGEZNFPLR-UHFFFAOYSA-N 1,4-bis(3-phenoxyphenoxy)benzene Chemical compound C=1C=CC(OC=2C=CC(OC=3C=C(OC=4C=CC=CC=4)C=CC=3)=CC=2)=CC=1OC1=CC=CC=C1 BEJQGHGEZNFPLR-UHFFFAOYSA-N 0.000 abstract 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 2
- 239000000654 additive Substances 0.000 abstract 2
- 150000001336 alkenes Chemical class 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 229910052751 metal Inorganic materials 0.000 abstract 2
- 239000002184 metal Substances 0.000 abstract 2
- 150000002989 phenols Chemical class 0.000 abstract 2
- 229920000642 polymer Polymers 0.000 abstract 2
- 238000002360 preparation method Methods 0.000 abstract 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 abstract 2
- 150000003751 zinc Chemical class 0.000 abstract 2
- KOKDSALTQSQPDH-UHFFFAOYSA-N 1,3-bis(3-phenoxyphenoxy)benzene Chemical compound C=1C=CC(OC=2C=C(OC=3C=C(OC=4C=CC=CC=4)C=CC=3)C=CC=2)=CC=1OC1=CC=CC=C1 KOKDSALTQSQPDH-UHFFFAOYSA-N 0.000 abstract 1
- JSRLURSZEMLAFO-UHFFFAOYSA-N 1,3-dibromobenzene Chemical compound BrC1=CC=CC(Br)=C1 JSRLURSZEMLAFO-UHFFFAOYSA-N 0.000 abstract 1
- JTNRGGLCSLZOOQ-UHFFFAOYSA-N 1,3-diphenoxybenzene Chemical compound C=1C=CC(OC=2C=CC=CC=2)=CC=1OC1=CC=CC=C1 JTNRGGLCSLZOOQ-UHFFFAOYSA-N 0.000 abstract 1
- SWJPEBQEEAHIGZ-UHFFFAOYSA-N 1,4-dibromobenzene Chemical compound BrC1=CC=C(Br)C=C1 SWJPEBQEEAHIGZ-UHFFFAOYSA-N 0.000 abstract 1
- BYIDGIRFXKNNDX-UHFFFAOYSA-N 1-(3,4-diphenoxy-2-phenylphenoxy)-3,4-diphenoxy-2-phenylbenzene Chemical compound C=1C=C(OC=2C(=C(OC=3C=CC=CC=3)C(OC=3C=CC=CC=3)=CC=2)C=2C=CC=CC=2)C(C=2C=CC=CC=2)=C(OC=2C=CC=CC=2)C=1OC1=CC=CC=C1 BYIDGIRFXKNNDX-UHFFFAOYSA-N 0.000 abstract 1
- MVCITNPWSJQCBC-UHFFFAOYSA-N 1-phenoxy-3-(3-phenoxyphenoxy)benzene Chemical compound C=1C=CC(OC=2C=C(OC=3C=CC=CC=3)C=CC=2)=CC=1OC1=CC=CC=C1 MVCITNPWSJQCBC-UHFFFAOYSA-N 0.000 abstract 1
- KCHIDDSVUFHVCV-UHFFFAOYSA-N 1-phenoxy-4-[3-[3-[3-(4-phenoxyphenoxy)phenoxy]phenoxy]phenoxy]benzene Chemical compound C=1C=C(OC=2C=C(OC=3C=C(OC=4C=C(OC=5C=CC(OC=6C=CC=CC=6)=CC=5)C=CC=4)C=CC=3)C=CC=2)C=CC=1OC1=CC=CC=C1 KCHIDDSVUFHVCV-UHFFFAOYSA-N 0.000 abstract 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 abstract 1
- JDGSDUNFBXVXHP-UHFFFAOYSA-N 2-(4-phenoxyphenoxy)phenol Chemical compound OC1=CC=CC=C1OC(C=C1)=CC=C1OC1=CC=CC=C1 JDGSDUNFBXVXHP-UHFFFAOYSA-N 0.000 abstract 1
- YEVQZPWSVWZAOB-UHFFFAOYSA-N 2-(bromomethyl)-1-iodo-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(I)C(CBr)=C1 YEVQZPWSVWZAOB-UHFFFAOYSA-N 0.000 abstract 1
- KDTZBYPBMTXCSO-UHFFFAOYSA-N 2-phenoxyphenol Chemical compound OC1=CC=CC=C1OC1=CC=CC=C1 KDTZBYPBMTXCSO-UHFFFAOYSA-N 0.000 abstract 1
- HBUCPZGYBSEEHF-UHFFFAOYSA-N 3-phenoxyphenol Chemical compound OC1=CC=CC(OC=2C=CC=CC=2)=C1 HBUCPZGYBSEEHF-UHFFFAOYSA-N 0.000 abstract 1
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 abstract 1
- SAIKULLUBZKPDA-UHFFFAOYSA-N Bis(2-ethylhexyl) amine Chemical compound CCCCC(CC)CNCC(CC)CCCC SAIKULLUBZKPDA-UHFFFAOYSA-N 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- 239000005069 Extreme pressure additive Substances 0.000 abstract 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- 239000004721 Polyphenylene oxide Substances 0.000 abstract 1
- 238000006085 Schmidt reaction Methods 0.000 abstract 1
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 125000005396 acrylic acid ester group Chemical group 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 230000002152 alkylating effect Effects 0.000 abstract 1
- 230000003466 anti-cipated effect Effects 0.000 abstract 1
- DVRQHPGPSJMVRD-UHFFFAOYSA-N butoxy(trichloromethyl)phosphinic acid Chemical compound CCCCOP(O)(=O)C(Cl)(Cl)Cl DVRQHPGPSJMVRD-UHFFFAOYSA-N 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 238000004939 coking Methods 0.000 abstract 1
- 229910052802 copper Inorganic materials 0.000 abstract 1
- 239000010949 copper Substances 0.000 abstract 1
- 238000005336 cracking Methods 0.000 abstract 1
- 238000000354 decomposition reaction Methods 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000005165 hydroxybenzoic acids Chemical class 0.000 abstract 1
- 230000005865 ionizing radiation Effects 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 239000012188 paraffin wax Substances 0.000 abstract 1
- 239000008188 pellet Substances 0.000 abstract 1
- 230000000737 periodic effect Effects 0.000 abstract 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 abstract 1
- 229960004889 salicylic acid Drugs 0.000 abstract 1
- 150000003870 salicylic acids Chemical class 0.000 abstract 1
- 238000010008 shearing Methods 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 238000003756 stirring Methods 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
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- C10M3/00—Liquid compositions essentially based on lubricating components other than mineral lubricating oils or fatty oils and their use as lubricants; Use as lubricants of single liquid substances
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- C10M173/00—Lubricating compositions containing more than 10% water
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- 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
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- C10M2207/02—Hydroxy compounds
- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/027—Neutral salts thereof
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- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
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- C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
- C10M2207/046—Hydroxy ethers
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- C10M2207/10—Carboxylix acids; Neutral salts thereof
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- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/14—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/141—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings monocarboxylic
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- C10M2207/142—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings polycarboxylic
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- C10M2207/146—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings having carboxyl groups bound to carbon atoms of six-membeered aromatic rings having a hydrocarbon substituent of thirty or more carbon atoms
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- C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
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- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
- C10M2209/084—Acrylate; Methacrylate
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- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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- C10M2211/04—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen, halogen, and oxygen
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- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
- C10M2215/062—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings containing hydroxy groups bound to the aromatic ring
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- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
- C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
- C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
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- C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
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- 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
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
- C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
- C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
- C10M2219/089—Overbased salts
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- 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
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
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- 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
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/041—Triaryl phosphates
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- 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
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/042—Metal salts thereof
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- 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
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
- C10M2223/063—Ammonium or amine salts
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- 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
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
- C10M2223/065—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds containing sulfur
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- 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
- C10N2010/00—Metal present as such or in compounds
- C10N2010/04—Groups 2 or 12
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- 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
- C10N2030/08—Resistance to extreme temperature
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- 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
- C10N2030/32—Light or X-ray resistance
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- 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
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/12—Gas-turbines
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- 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
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/12—Gas-turbines
- C10N2040/13—Aircraft turbines
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- 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
- C10N2050/00—Form in which the lubricant is applied to the material being lubricated
- C10N2050/01—Emulsions, colloids, or micelles
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Lubricants (AREA)
Abstract
Polyphenyl polyethers comprising at least three, preferably 4 to 8, benzene nuclei connected to one another by oxygen atoms, there being at least one meta dioxyphenylene group, are effective lubricants for metal surfaces at high operating temperatures and/or in the presence of ionizing radiation. The specification includes tables showing the flash point, fire point, initial decomposition temperature, viscosities at 100 DEG , 210 DEG , 400 DEG and 600 DEG F., oxidation stability and coking resistance of m-diphenoxybenzene, bis(m-phenoxyphenyl)-ether, m-phenoxyphenyl-p-phenoxyphenyl ether, p-bis(m-phenoxyphenoxy) benzene, m-bis(m-phenoxyphenoxy) benzene, and m-bis[m-(p-phenoxyphenoxy) phenoxy] benzene compared with polyphenyl polyethers containing no meta dioxyphenyl groups, and with other lubricants. Where temperatures below 300 DEG F. are anticipated during the useful life of the lubricant, pour point depressants and viscosity index improvers such as the polymers of acrylic acid esters or of 2-alkyl acrylic acid esters may be utilized. It may be desirable to subject the polymers to a shearing action, e.g. by passing them through an injector nozzle, before incorporating them in the compositions. Suitable anti-lacquering agents for addition to the compositions are salts of aromatic carboxylic acids or of phenols with a metal of Group II of the Periodic Table. Particularly effective additives of this type are the zinc salts of alkylated salicyclic acids containing 8 to 20 carbon atoms in the alkyl group. Extreme pressure additives may be added, such as trioctyl phosphate, tricresyl phosphate, monobutyl hydrogen trichloromethyl-phosphonate and its salts with di(2-ethylhexyl) amine. For the preparation of the polyphenyl polyethers see Group IV(b).ALSO:Polyphenyl polyethers comprising at least four benzene nuclei connected to one another by oxygen atoms, there being at least one metadioxyphenylene group, are prepared by heating, in the presence of copper powder, a halogenated benzene hydrocarbon, a halogenated polyphenyl ether or polyether with an alkali metal salt of a phenol, a phenoxyphenol or a polyphenoxyphenol. In Example 3, a mixture of m-phenoxyphenol and potassium hydroxide pellets is heated under vacuum until no more water is evolved. Copper catalyst is added, and the mixture is heated to 180 DEG C. in an atmosphere of nitrogen. p-Dibromobenzene is then gradually added with stirring; and the mixture is heated at about 220 DEG C. for 7 hours. The product is extracted with benzene, and the extract is distilled under reduced pressure to isolate p-bis(m-phenoxyphenoxy) benzene <FORM:0886978/IV (b)/1> Example 4 describes the preparation of an ether having 7 benzene nuclei joined by 6 oxygen atoms - [meta - bis meta - (para - phenoxy - phenoxy)phenoxy] benzene, by reacting sodium meta (p-phenoxyphenoxy) phenol with m-dibromobenzene. These polyphenyl polyethers have use as lubricants (see Group III). Suitable additives are salts of alkylated hydroxy-benzoic acids which may be produced (a) by reacting salicylic acid or 4-hydroxybenzoic acid with a mixture of alkenes obtained by cracking paraffin wax, or with a mixture of alcohols, or (b) from alkylated phenols by the Kolbe-Schmidt reaction. The zinc salt of a mixture of alkyl salicylic acids, made by alkylating phenol with a mixture of alkenes containing 14 to 18 carbon atoms in the molecule and converting the resulting alkyl phenols into the corresponding salicylic acids, is referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US77537058A | 1958-11-21 | 1958-11-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB886978A true GB886978A (en) | 1962-01-10 |
Family
ID=25104185
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB39285/59A Expired GB886978A (en) | 1958-11-21 | 1959-11-19 | Polyphenyl ethers |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE584837A (en) |
| CH (1) | CH383533A (en) |
| DE (1) | DE1444887A1 (en) |
| GB (1) | GB886978A (en) |
| NL (1) | NL114100C (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3391195A (en) * | 1963-12-04 | 1968-07-02 | Monsanto Res Corp | Fluorinated polyphenyl ethers |
| US3409677A (en) * | 1963-08-07 | 1968-11-05 | Monsanto Co | Polyphenyl ether treatment |
| CN111635799A (en) * | 2020-05-15 | 2020-09-08 | 清华大学 | Lubricating oil composition and its use |
-
0
- NL NL114100D patent/NL114100C/xx active
-
1959
- 1959-11-19 BE BE584837A patent/BE584837A/en unknown
- 1959-11-19 DE DE19591444887 patent/DE1444887A1/en active Pending
- 1959-11-19 GB GB39285/59A patent/GB886978A/en not_active Expired
- 1959-11-19 CH CH8081859A patent/CH383533A/en unknown
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3409677A (en) * | 1963-08-07 | 1968-11-05 | Monsanto Co | Polyphenyl ether treatment |
| US3391195A (en) * | 1963-12-04 | 1968-07-02 | Monsanto Res Corp | Fluorinated polyphenyl ethers |
| CN111635799A (en) * | 2020-05-15 | 2020-09-08 | 清华大学 | Lubricating oil composition and its use |
| CN111635799B (en) * | 2020-05-15 | 2021-09-03 | 清华大学 | Lubricating oil composition and use thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| BE584837A (en) | 1960-05-19 |
| DE1444887A1 (en) | 1969-03-20 |
| NL114100C (en) | |
| CH383533A (en) | 1964-10-31 |
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