GB790923A - New or improved glycol complex esters - Google Patents

New or improved glycol complex esters

Info

Publication number
GB790923A
GB790923A GB11956/55A GB1195655A GB790923A GB 790923 A GB790923 A GB 790923A GB 11956/55 A GB11956/55 A GB 11956/55A GB 1195655 A GB1195655 A GB 1195655A GB 790923 A GB790923 A GB 790923A
Authority
GB
United Kingdom
Prior art keywords
glycol
dicarboxylic acids
saturated aliphatic
sebacic acid
residue
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
Application number
GB11956/55A
Inventor
Stuart Walter Critchley
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Geigy Co Ltd
Original Assignee
Geigy Co Ltd
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 Geigy Co Ltd filed Critical Geigy Co Ltd
Publication of GB790923A publication Critical patent/GB790923A/en
Expired legal-status Critical Current

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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
    • C07C69/80—Phthalic acid esters
    • 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
    • C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
    • C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
    • C08G63/16—Dicarboxylic acids and dihydroxy compounds
    • C08G63/20—Polyesters having been prepared in the presence of compounds having one reactive group or more than two reactive groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/10—Esters; Ether-esters
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L27/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers
    • C08L27/02—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment
    • C08L27/04—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment containing chlorine atoms
    • C08L27/06—Homopolymers or copolymers of vinyl chloride
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
    • C08L67/02—Polyesters derived from dicarboxylic acids and dihydroxy 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
    • 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
    • C10M2207/30—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids
    • C10M2207/304—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids derived from the combination of monohydroxy compounds, dihydroxy compounds and dicarboxylic acids only and having no free hydroxy or carboxyl 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
    • C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
    • 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
    • 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
    • C10M2209/102—Polyesters
    • 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
    • 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
    • C10M2209/11—Complex polyesters
    • C10M2209/112—Complex polyesters having dihydric acid centres
    • 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
    • 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
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Lubricants (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

The invention comprises complex esters of the general formula: <FORM:0790923/IV (b)/1> wherein n is a number from 2 to 10, the R1's represent the residues of dicarboxylic acids at least one being saturated aliphatic and at least one being aromatic, R2 is the residue of an alkylene glycol and R3 is the residue of a saturated aliphatic monohydric alcohol. They may be obtained by bringing about a reaction by heat in the absence of an esterification catalyst between a saturated aliphatic dicarboxylic acid, an aromatic dicarboxylic acid, an alkylene glycol, and at least one saturated aliphatic monohydric alcohol, the molecular proportion of glycol being between 0.66 and 0.96 and the molecular proportion of monohydric alcohol being between 0.12 and 0.66 for each molecular proportion of total dicarboxylic acids. Either or both of the dicarboxylic acids can be used in the form of their anhydrides. The reaction can be carried out by heating the dicarboxylic acids the glycol and the monohydric alcohol in the absence of air, e.g. in a nitrogen atmosphere, and by bubbling nitrogen through the reaction mass, or the dicarboxylic acids and the glycol can first be heated together in the absence of air and the resulting acid glycol ester then heated with a monohydric alcohol. Specified glycols are 1 : 2 propylene glycol, ethylene glycol, and butylene glycol. Polyglycols may also be used. The dicarboxylic acids are preferably sebacic acid and phthalic acid and specified monohydric alcohols are 2-ethyl hexanol and 3,5,5-trimethyl hexanol. The reaction can be carried out at above 130 DEG C. and is preferably carried out at progressively increasing temperatures, e.g. up to 200-250 DEG C. It is preferred to carry out the reaction in the absence of a diluent. Examples are given for the production of complex esters from sebacic acid, phthalic anhydride, 2-ethyl hexanol, and 1,2-propylene glycol using various molecular proportions of the reactants to give different values of "n." A comparative example is also given for the preparation of a complex ester from sebacic acid (3 mols.), 2-ethylhexanol (0.9 mol.) and 1.2-propylene glycol (2.83 mols.). The products are stated to be useful as thickeners for synthetic diester lubricants (see Group III) and as plasticizers for thermoplastic materials especially polyvinyl chloride (see Group IV (a)).ALSO:Complex esters of the formula: R3OOCR1COO(R2OOCR1COO)nR3 wherein n is a number from 2 to 10, the R1's represent the residues of dicarboxylic acids at least one being saturated aliphatic and at least one being aromatic, R2 is the residue of an alkylene glycol, and R3 is the residue of a saturated aliphatic monohydric alcohol (see Group IV (b)) may be used as thickeners for synthetic diester lubricants, e.g. for those prepared from sebacic acid and 2-ethylhexanol or 3,5,5-trimethylhexanol, or for mixed esters of these two alcohols. A table is given to show the effect on the viscosity, A.S.T.M. slope, and pour point, of adding various proportions of complex esters of the above type derived from sebacic acid, phthalic anhydride, 1,2-propylene glycol and 2-ethyl-hexanol to di-2-ethyl-hexyl sebacate and comparative figures are also given to show the effect of adding to the same diester a complex ester derived from sebacic acid (3 mol) 2-ethylhexanol (0.9 mol.) and 1,2-propylene glycol (2.85 mol.). Other glycols and monohydric alcohols from which the aliphatic-aromatic complex ester may be derived are ethylene and butylene glycols, polyglycols and 3,5,5-trimethyl hexanol.ALSO:Polymers, e.g. polyvinyl chloride, are plasticized with complex esters of the formula R3OOCR1COO(R2OOCR1COO)nR3 wherein n is a number from 2 to 10, the R1's are residues of dicarboxylic acids, at least one being saturated aliphatic and at least one being aromatic, R2 is the residue of an alkylene glycol, and R3 is the residue of a saturated aliphatic monohydric alcohol (see Group IV (b)). In an example a plasticized composition is made by milling together polyvinyl chloride, a complex ester in which n is 4.3 and which is derived from sebacic acid, phthalic anhydride, 1,2-propylene glycol and 2-ethyl hexanol and a paste comprising white lead and dioctyl phthalate. Other glycols and monohydric alcohols from which the complex esters may be derived are ethylene- and butylene glycols, polyglycols and 3-, 5,5-trimethyl hexanol.
GB11956/55A 1955-04-26 1955-04-26 New or improved glycol complex esters Expired GB790923A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB357385X 1955-04-26

Publications (1)

Publication Number Publication Date
GB790923A true GB790923A (en) 1958-02-19

Family

ID=10381030

Family Applications (1)

Application Number Title Priority Date Filing Date
GB11956/55A Expired GB790923A (en) 1955-04-26 1955-04-26 New or improved glycol complex esters

Country Status (4)

Country Link
CH (1) CH357385A (en)
DE (1) DE1016696B (en)
GB (1) GB790923A (en)
NL (1) NL101240C (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2991252A (en) * 1957-08-16 1961-07-04 British Petroleum Co Synthetic lubricants

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE793201A (en) * 1971-12-27 1973-06-22 Monsanto Co POLYESTERS AND VINYL HALOGENIDE RESINS PLASTICIZED BY THEM

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2991252A (en) * 1957-08-16 1961-07-04 British Petroleum Co Synthetic lubricants

Also Published As

Publication number Publication date
DE1016696B (en) 1957-10-03
NL101240C (en)
CH357385A (en) 1961-10-15

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