HK36192A - Norbornyl dimer ester and polyester additives for lubricants and fuels - Google Patents

Norbornyl dimer ester and polyester additives for lubricants and fuels

Info

Publication number
HK36192A
HK36192A HK361/92A HK36192A HK36192A HK 36192 A HK36192 A HK 36192A HK 361/92 A HK361/92 A HK 361/92A HK 36192 A HK36192 A HK 36192A HK 36192 A HK36192 A HK 36192A
Authority
HK
Hong Kong
Prior art keywords
polyester
alkyl
carbon atoms
acid
aryl
Prior art date
Application number
HK361/92A
Other languages
English (en)
French (fr)
Inventor
Richard Michael Lange
Original Assignee
The Lubrizol Corporation
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 The Lubrizol Corporation filed Critical The Lubrizol Corporation
Publication of HK36192A publication Critical patent/HK36192A/en

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    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L10/00—Use of additives to fuels or fires for particular purposes
    • C10L10/08—Use of additives to fuels or fires for particular purposes for improving lubricity; for reducing wear
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
    • C07F9/165—Esters of thiophosphoric acids
    • C07F9/177—Esters of thiophosphoric acids with cycloaliphatic alcohols
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
    • C08G63/692—Polyesters containing atoms other than carbon, hydrogen and oxygen containing phosphorus
    • C08G63/6924—Polyesters containing atoms other than carbon, hydrogen and oxygen containing phosphorus derived from polycarboxylic acids and polyhydroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/26—Organic compounds containing phosphorus
    • C10L1/2633—Organic compounds containing phosphorus phosphorus bond to oxygen (no P. C. bond)
    • C10L1/265—Organic compounds containing phosphorus phosphorus bond to oxygen (no P. C. bond) oxygen and/or sulfur bonds
    • C—CHEMISTRY; METALLURGY
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
    • C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
    • C10M137/04—Phosphate esters
    • C10M137/10—Thio derivatives
    • C10M137/105—Thio derivatives not containing metal
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    • C10M153/00—Lubricating compositions characterised by the additive being a macromolecular compound containing phosphorus
    • C10M153/04—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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    • C10M173/00—Lubricating compositions containing more than 10% water
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    • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/02—Water
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    • C10M2201/087—Boron oxides, acids or salts
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    • C10M2205/06—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing conjugated dienes
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    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/14—Synthetic waxes, e.g. polythene waxes
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    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/107—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of two or more specified different alkylene oxides covered by groups C10M2209/104 - C10M2209/106
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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
    • C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
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    • C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2215/042—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Alkoxylated derivatives thereof
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    • 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
    • C10M2215/064—Di- and triaryl amines
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Claims (21)

1. Dimer-Ester der Formel in der A bedeutet, wobei R einen Alkyl-, Aryl- oder Aralkylrest bedeutet und R1 unabhängig ein Wasserstoffatom oder einen Kohlenwasserstoffrest darstellt und T einen Kohlenwasserstoffrest bedeutet.
2. Dimer-Ester nach Anspruch 1, wobei Reinen Alkylenrest mit 1 bis etwa 6 Kohlenstoffatomen bedeutet und R1 einen Alkylrest mit 2 bis etwa 12 Kohlenstoffatomen darstellt.
3. Dimer-Ester nach Anspruch 2, wobei R eine Ethylengruppe bedeutet und R1 einen Alkylrest mit 2 bis etwa 7 Kohlenstoffatomen darstellt.
4. Polyester der Formel in derX und Y Endgruppen des Polymers sind und unabhängig Wasserstoffatome, Alkyl-, Aryl-, Aralkyl-, Hydroxy-, Alkoxy-, Carboalkoxy-, Aryloxy-, Dialkylamino-, Diarylamino-, Alkylthio- oder Arylthioreste bedeuten, p 3 bis etwa 30 ist, r 0 bis etwa 30 ist und die Summe von p + r von 3 bis etwa 40 reicht, D bedeutet, wobei R einen Alkyl-, Aryl- oder Aralkylrest darstellt und R2 und R3 eine Bindung zu den anderen wiederkehrenden Einheiten sind und Ebedeutet, wobei R4 und R5 gleich oder verschieden sind und Kohlenwasserstoffreste bedeuten, und n 0 oder 1 ist.
5. Polyester nach Anspruch 4, wobei p 4 bis 10 ist, r 0 ist und R3 einen Alkylenrest mit 1 bis etwa 6 Kohlenstoffatomen bedeutet.
6. Polyester nach Anspruch 5, wobei R3 eine Ethylengruppe ist.
7. Polyester nach Anspruch 4, wobei p 4 bis 10 ist, r 3 bis 10 ist und die Summe von p + r von 7 bis 12 reicht, R3 einen Alkylenrest mit 1 bis etwa 6 Kohlenstoffatomen bedeutet, R4 und R5 alkylierte Bernsteinsäurereste darstellen, in denen der Alkylrest etwa 8 bis etwa 200 Kohlenstoffatome enthält.
8. Diester, hergestellt nach dem Verfahren, das umfaßt : Kondensation von
(A) 5-Norbornen-2,3-dicarbonsäureanhydrid ;
(B) 0,0-disubstituierter Dithiophosphorsäure, in der die Substituenten, die gleich oder verschieden sein können, Alkyl-, Aryl- oder Alkylreste mit bis zu 30 Kohlenstoffatomen sind ; und
(C) einem Polyol ; wobei das Addukt von (A) und (B) mit dem Polyol (C) in einem solchen Verhältnis und unter solchen Bedingungen kondensiert wird, daß das Produkt ein dimerer Ester der Formel A-T-A ist, in der A bedeutet, wobei R einen Alkyl-, Aryl- oder Aralkylrest bedeutet und RI unabhängig ein Wasserstoffatom oder einen Kohlenwasserstoffrest darstellt und T ein Kohlenwasserstoffrest ist.
9. Dimer-Ester nach Anspruch 8, wobei das Polyol ein Alkylenglykol ist.
10. Dimer-Ester nach Anspruch 9, wobei das Alkylenglykol Ethylenglykol ist.
11. Polyester, hergestellt nach dem Verfahren, das umfaßt : Kondensation von
(A) 5-Norbornen-2,3-dicarbonsäureanhydrid ;
(B) 0,0-disubstituierter Dithiophosphorsäure, in der die Substituenten, die gleich oder verschieden sein können, Alkyl-, Aryl- oder Aralkylreste mit bis zu 30 Kohlenstoffatomen sind ; und
(C) einem Polyol ; wobei die Umsetzung derart durchgeführt wird, daß äquivalente Verhältnisse von OH : C = O eingesetzt werden, die Umsetzung bis zum Punkt vollständiger Entfernung des Wassers durchgeführt wird und der hergestellte Polyester ein Molekulargewicht von etwa 1000 bis etwa 10000 aufweist.
12. Polyester nach Anspruch 11, wobei das Polyol ein Alkylenglykol ist.
13. Polyester nach Anspruch 12, wobei das Alkylenglykol Ethylenglykol ist.
14. Polyester nach Anspruch 11, wobei der Polyesterfemer aus einer zusätzlichen Polycarbonsäure oder einem Derivat davon hergestellt wird.
15. Polyester nach Anspruch 14, wobei die zusätzliche Polycarbonsäure eine alkylierte Bemsteinsäure oder ein Derivat davon ist, in der der Alkylrest etwa 8 bis etwa 200 Kohlenstoffatome enthält.
16. Schmiermittel, umfassend eine größere Menge eines Schmieröls mit Schmiermittel-Viskosität und eine kleinere, wirksame Menge mindestens eines Dimer-Esters undloder Polyesters nach einem der Ansprüche 1 bis 15.
17. Treibstoff-Zusammensetzung, umfassend eine größere Menge eines Treibstoffs und eine kleinere, wirksame Menge mindestens eines Dimer-Esters und/oder Polyesters nach einem der Ansprüche 1 bis 15.
18. Konzentrat zur Formulierung einer Schmiermittel- oder Treibstoff-Zusammensetzung, umfassend von etwa 1 bis etwa 99 Gew.-% mindestens eines Dimer-Esters und/oder Polyesters nach einem der Ansprüche 1 bis 15 und ein normalerweise flüssiges, im wesentlichen inertes organisches LösungsmittelNerdünnungsmittel.
19. Zusatz zur Formulierung von Schmiermittel- und Treibstoff-Zusammensetzungen, umfassend mindestens einen Dimer-Ester oder Polyester nach einem der Ansprüche 1 bis 15.
20. Verfahren zur Herstellung eines Diesters, umfassend die Kondensation von
(A) 5-Norbornen-2,3-dicarbonsäureanhydrid ;
(B) 0,0-disubstituierter Dithiophosphorsäure, in der die Substituenten, die gleich oder verschieden sein können, Alkyl-, Aryl- oder Aralkylreste mit bis zu 30 Kohlenstoffatomen sind ; und
(C) einem Polyol, wobei das Addukt von (A) und (B) mit dem Polyol (C) in einem solchen Verhältnis und unter solchen Bedingungen kondensiert wird, daß das Produkt ein dimerer Ester der Formel A-T-A ist, in der A bedeutet, wobei R einen Alkyl-, Aryl- oder Aralkylrest darstellt und Rl unabhängig ein Wasserstoffatom oder einen Kohlenwasserstoffrest bedeutet und T einen Kohlenwasserstoffrest darstellt.
21. Verfahren zur Herstellung eines Polyesters, umfassend die Polykondensation von
(A) 5-Norbornen-2,3-dicarbonsäureanhydrid ;
(B) 0,0-disubstituierter Dithiophosphorsäure, in der die Substituenten, die gleich oder verschieden sein können, Alkyl-, Aryl- oder Aralkylreste mit bis zu 30 Kohlenstoffatomen sind ; und
(C) einem Polyol ; wobei die Umsetzung derart durchgeführt wird, daß äquivalente Verhältnisse von OH : C = O eingesetzt werden, die Umsetzung bis zu dem Punkt vollständiger Entfernung des Wassers durchgeführt wird, und der hergestellte Polyester ein Molekulargewicht von etwa 1000 bis etwa 10000 aufweist.
HK361/92A 1986-07-11 1992-05-21 Norbornyl dimer ester and polyester additives for lubricants and fuels HK36192A (en)

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US06/884,573 US4707301A (en) 1986-07-11 1986-07-11 Norbornyl dimer ester and polyester additives for lubricants and fuels
PCT/US1987/001581 WO1988000589A2 (en) 1986-07-11 1987-07-02 Norbornyl dimer ester and polyester additives for lubricants and fuels

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KR100362938B1 (ko) * 1998-12-31 2003-10-10 주식회사 하이닉스반도체 신규의포토레지스트가교제,이를포함하는포토레지스트중합체및포토레지스트조성물
US7888298B2 (en) * 2007-03-20 2011-02-15 Exxonmobil Research And Engineering Company Lubricant compositions with improved properties
KR101278872B1 (ko) 2011-11-29 2013-07-01 한국화학연구원 디알킬 디티오카바메이트 그룹을 갖는 노보넨 디알킬 에스테르 화합물, 이를 포함하는 내마모제 및 윤활유
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US4707301A (en) 1987-11-17
ES2006777A6 (es) 1989-05-16
ATE67996T1 (de) 1991-10-15
EP0314700B1 (de) 1991-10-02
SG18992G (en) 1992-04-16
WO1988000589A2 (en) 1988-01-28
CA1291153C (en) 1991-10-22
MX164290B (es) 1992-07-30
US4753662A (en) 1988-06-28
ZA875003B (en) 1988-03-30
JPH02500973A (ja) 1990-04-05
AU7709787A (en) 1988-02-10
JP2582389B2 (ja) 1997-02-19

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