WO2003097707A1 - Procede de production de copolymeres de n-vinyl lactames et d'olefines - Google Patents

Procede de production de copolymeres de n-vinyl lactames et d'olefines Download PDF

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Publication number
WO2003097707A1
WO2003097707A1 PCT/EP2003/004917 EP0304917W WO03097707A1 WO 2003097707 A1 WO2003097707 A1 WO 2003097707A1 EP 0304917 W EP0304917 W EP 0304917W WO 03097707 A1 WO03097707 A1 WO 03097707A1
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WO
WIPO (PCT)
Prior art keywords
aliphatic
olefins
aromatic
carboxylic acids
esters
Prior art date
Application number
PCT/EP2003/004917
Other languages
German (de)
English (en)
Inventor
Matthias Kroner
Franz Weingart
Axel Kistenmacher
Original Assignee
Basf Aktiengesellschaft
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 Basf Aktiengesellschaft filed Critical Basf Aktiengesellschaft
Priority to AU2003224155A priority Critical patent/AU2003224155A1/en
Publication of WO2003097707A1 publication Critical patent/WO2003097707A1/fr

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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
    • C10M173/00—Lubricating compositions containing more than 10% water
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
    • C08F210/14—Monomers containing five or more carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F222/00—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 carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
    • C08F222/04—Anhydrides, e.g. cyclic anhydrides
    • C08F222/06—Maleic anhydride
    • 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
    • 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
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
    • C10M2205/028—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms
    • 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
    • C10M2209/02—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
    • C10M2209/086—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 polycarboxylic, e.g. maleic acid
    • 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
    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/02—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/028—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a nitrogen-containing hetero ring
    • 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
    • C10N2040/20—Metal working
    • C10N2040/24—Metal working without essential removal of material, e.g. forming, gorging, drawing, pressing, stamping, rolling or extruding; Punching metal
    • 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
    • C10N2070/00—Specific manufacturing methods for lubricant compositions

Definitions

  • the present invention relates to a new process for the preparation of copolymers of N-vinyl lactams and olefins by radical copolymerization in the presence of a solvent.
  • the invention also relates to polymer solutions which contain as essential constituents (A) at least one copolymer of N-vinyl lactams and olefins and (B) at least one ester of aromatic carboxylic acids with aliphatic and / or aromatic alcohols or of aliphatic carboxylic acids with aliphatic and / or contain aromatic alcohols as solvents, and their use as emulsifiers for lubricants.
  • A at least one copolymer of N-vinyl lactams and olefins
  • B at least one ester of aromatic carboxylic acids with aliphatic and / or aromatic alcohols or of aliphatic carboxylic acids with aliphatic and / or contain aromatic alcohols as solvents, and their use as emulsifiers for lubricants.
  • processing aids are usually emulsions of lubricants, in particular lubricating oils, in water, which contain emulsifiers and other additives (w / o emulsions).
  • the lubricant emulsions are subject to high demands with regard to lubrication, circulation stability and wastewater pollution.
  • the lubricating effect and emulsion stability behave in opposite directions: If you try to determine the amount of plating, i.e. the oil film on the metal; to increase, the emulsion stability is usually deteriorated. However, a stable emulsion has a poor lubricating effect because there is too little oil on the metal sheet.
  • suitable emulsifiers it is possible to influence the emulsion stability and adjust it to the desired level.
  • DE-C-34 21 967 describes cationic copolymers of nitrogen-containing monomers based on acrylate with vinyl monomers, inter alia.
  • N-vinyl pyrrolidone proposed as an emulsifier for metalworking oils.
  • the invention was based on the object of making further emulator systems for lubricants advantageously accessible.
  • polymer solutions were found which as essential constituents (A) at least one copolymer of N-vinyl lactams and olefins and (B) at least one ester of aromatic carboxylic acids with aliphatic and / or aromatic alcohols or of aliphatic carboxylic acids with aliphatic and / or aromatic alcohols Contain solvents.
  • Suitable solvents according to the invention are esters of aromatic carboxylic acids with aliphatic and / or aromatic alcohols and esters (preferably saturated) aliphatic carbon acids with aliphatic and / or aromatic alcohols.
  • the carboxylic acids can contain one or more, in particular two, carboxyl groups.
  • the esters of polyhydric alcohols can of course also be mixed esters. Monohydric alcohols are preferred as the alcohol component.
  • Esters of aromatic carboxylic acids, especially aromatic dicarboxylic acids, with aliphatic alcohols are particularly preferred.
  • Esters of aliphatic carboxylic acids with aliphatic alcohols preferably have a minimum number of 8 carbon atoms.
  • the alcohols can also be alkoxylated and have 1 to 200, preferably 1 to 40, alkylene oxide units.
  • alkylene oxide ethylene oxide, propylene oxide and butylene oxide can be used alone or in mixtures. If different alkylene oxides are used, the alkylene oxide units can be arranged randomly or in blocks in the alkoxylation products.
  • Benzoic acid esters such as methyl benzoate, ethyl benzoate, nyl benzoate, tridecyl benzoate, eicosano benzoate and benzyl benzoate;
  • Phenylacetic acid esters such as phenylacetic acid nyl ester and p enyl acetic acid benzyl ester;
  • Phthalic acid esters such as dimethyl phthalate, diethyl phthalate, dibutyl phthalate, diisobutyl phthalate, diphthalate phthalate, bis-2-ethylhexyl phthalate,
  • Isophthalic acid esters such as dibutyl isophthalate
  • Terephthalic acid esters such as dimethyl terephthalate, dinonyne terephthalate and dibenzyl terephthalate
  • Acetic acid esters such as acetic acid hexyl ester and acetic acid tallow fatty alcohol ester
  • Propionic acid esters such as * propionic acid tridecyl ester
  • 2-ethylhexyl acid esters such as 2-ethylhexyl acid 2'-ethylhexyl ester
  • Oxalic acid esters such as dibutyl oxalate
  • Succinic acid esters such as diethyl succinate
  • Adipic acid esters such as diethyl adipate, dimethyl adipate, bis-2-ethylhexyl adipate, diisononate adipate and bisbutyl pentyl adipate;
  • Citric acid esters such as trimethyl citrate, triethyl citrate and tributyl citrate.
  • phthalic acid esters and adipic acid esters Preference is given to phthalic acid esters and adipic acid esters, phthalic acid esters being particularly preferred and phthalic acid esters with aliphatic C 1 -C 2 -alcohols being very particularly preferred.
  • N-vinyl lactams used according to the invention as starting material are in particular N-vinyl pyrrolidone, N-vinyl piperidone and N-vinyl caprolactam, with N-vinyl pyrrolidone being preferred.
  • olefins can be used for the alkylation.
  • Mono-olefins with a terminal double bond (I-01efine) are preferred, but it is also possible to use olefins in which the double bond is within the molecule.
  • Aliphatic and cycloaliphatic olefins with 2 to 1000 carbon atoms and aromatic olefins with 8 to 50 carbon atoms are particularly suitable.
  • unbranched 1-olefins such as ethylene, propylene, 1-butene, isobutene, 1-pentene, 1-hexene, 1-octene, 1-decene, 1-dodecene, 1-tridecene, 1-tetradecene, 1-pentadecene, 1- Hexadecene, 1-heptadecene, 1-octa-decene, 1-nonadecene, 1-eicosen, 1-docosen, 1-tricosen, 1-tetra- cosen, 1-pentacosen and 1-triaconten;
  • unbranched 1-olefins such as ethylene, propylene, 1-butene, isobutene, 1-pentene, 1-hexene, 1-octene, 1-decene, 1-dodecene, 1-tridecene, 1-tetradecene, 1-pentadecene, 1- Hexade
  • branched 1-olefins such as 2-ethyl-1-butene, 2-methyl-1-pentene, 5-methyl-1-hexene, 2-methyl-1-pentene, 2,4, 4-trimethyl-1-pentene, 3-ethyl-1-pentene and 2-ethyl-1-hexene;
  • olefin mixtures such as Cn-Cis-olefins, Ci5-C 2 o _ 01efine, Co-C 24 -olefins, mixtures of olefins with more than 20 carbon atoms, mixtures of olefins with more than 30 carbon atoms and mixtures of olefins with 20 up to 42 carbon atoms;
  • olefins of different lengths such as mixtures of 50% by weight of 1-decene and 50% by weight of 1-eicose, 80% by weight of 1-dodecene and 20% by weight of 1-hexadecene and 30% by weight of isobutene and 70 wt% C 0 -C 24 olefin;
  • Olefins with a non-permanent double bond such as 2-butene, 2-decene, cyclohexene, indene, 2, 4, 4-trimethylpentene-2 and diisobutene;
  • aromatic olefins such as styrene and ⁇ -methylstyrene.
  • Aliphatic olefins are preferred as pure substances or mixtures, particularly preferably those with terminal double bonds, very particularly preferably aliphatic C 4 -C 24 -01efins with terminal double bonds as pure substances or as mixtures.
  • the weight ratio of N-vinyl lactam to olefin according to the invention is generally 10:90 to 90:10, preferably 40:60 to 80:20.
  • the copolymerization takes place according to the invention in the form of a solution polymerization. This is usually the case when using esters of aromatic carboxylic acids as solvents. However, the copolymers are not soluble in some esters of aliphatic carboxylic acids, here the reaction takes the form of a precipitation polymerization.
  • initiators can be used as polymerization initiators.
  • examples include hydrogen peroxide and organic peroxy compounds, for example hydroperoxides such as tert. Butyl hydroperoxide, dialkyl peroxides such as di-tert. -butyl peroxide and
  • Peroxyesters such as tert-butyl perethyl hexanoate and azo initiators. Mixtures of two or more initiators can of course also be used.
  • initiator based on the weight of N-vinyl lactam and olefin, are used.
  • the initiator is preferably added dissolved in carboxylic acid ester.
  • polymerization regulators can be added to achieve particularly low molecular weights.
  • polymerization regulators can be added to achieve particularly low molecular weights.
  • compounds known for this purpose e.g. Mercapto compounds such as mercaptoethanol, thioglycolic acid, mercaptopropionic acid and dodecyl erca tan, and phosphorus compounds with low oxidation states such as phosphorous acid and hypophosphorous acid are suitable.
  • the process according to the invention is preferably carried out without a polymerization regulator.
  • the polymerization temperature is usually 100 to 250 ° C, preferably 120 to 170 ° C. Temperatures in the upper range favor the formation of copolymers with a low molecular weight M w and lower proportions of N-vinyllactam homopolymer.
  • the polymerization time is generally from 0.5 to 20 h, preferably from 1 to 10 h.
  • a mixture of carboxylic acid ester and olefin is heated to the desired reaction temperature while stirring and introducing an inert gas, for example nitrogen. Then N-vinyl lactam and, in parallel, initiator, if desired both of which are each dissolved in further carboxylic acid ester, are metered in in about 0.5 to 8 h. However, it is also possible to add only the carboxylic acid ester and add the olefin in parallel with N-vinyl lactam and initiator or to add carboxylic acid ester, olefin and N-vinyl lactam and add only the initiator. After a post-polymerization time of about 0 to 8 hours, the reaction mixture is cooled to room temperature.
  • the molecular weight M w of the copolymers obtained according to the invention is generally 500 to 30,000, preferably 1,000 to 10,000.
  • the K value of the copolymers is usually 10 to 50, in particular 15 to 40, determined by H. Fikentscher, Cellulose-Chemie, Vol. 13, pp. 58-64 and 71-74 (1932) 1% by weight in chloroform at 25 ° C.
  • the copolymerization is advantageously carried out in such a way that 10 to 70% by weight, especially 25 to 50% by weight, solutions of the copolymers are obtained.
  • the polymer solutions according to the invention are outstandingly suitable as emulsifiers for lubricants.
  • emulsions of lubricating oils' can be prepared in water, which are stabilized with the polymer solutions.
  • the emulsions obtained can advantageously be used as metalworking agents, e.g. can be used as a lubricant for cutting and rolling metal sheets.
  • metalworking agents e.g. can be used as a lubricant for cutting and rolling metal sheets.
  • 0.1 to 20% by weight of a 5 to 50% by weight polymer solution is used.
  • Preferred emulsifiers are solutions of copolymers of N-vinylpyrrolidone and aliphatic C 1 -C 30 -01efins in phthalic C 1 -C 4 -alkyl esters.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

L'invention concerne un procédé de production de copolymères de N-vinyl lactames et d'oléfines, par copolymérisation radicalaire en présence d'un solvant, caractérisé en ce que ce solvant se présente sous la forme d'un ester d'acide carboxylique. L'invention se rapporte en outre à des solutions polymères comprenant les principaux ingrédients suivants : (A) au moins un copolymère de N-vinyl lactames et d'oléfines ; et (B) au moins un ester d'acides carboxyliques aromatiques comportant des alcools aliphatiques et/ou aromatiques ou un ester d'acides carboxyliques aliphatiques comprenant des alcools aliphatiques et/ou aromatiques en tant que solvant. L'invention concerne par ailleurs l'utilisation de ces solutions polymères en tant qu'émulsifiants pour des lubrifiants.
PCT/EP2003/004917 2002-05-15 2003-05-12 Procede de production de copolymeres de n-vinyl lactames et d'olefines WO2003097707A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2003224155A AU2003224155A1 (en) 2002-05-15 2003-05-12 Method for producing copolymers of n-vinyl lactams and olefins

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10221806 2002-05-15
DE10221806A DE10221806A1 (de) 2002-05-15 2002-05-15 Verfahren zur Herstellung von Copolymerisaten von N-Vinyllactamen und Olefinen

Publications (1)

Publication Number Publication Date
WO2003097707A1 true WO2003097707A1 (fr) 2003-11-27

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AU (1) AU2003224155A1 (fr)
DE (1) DE10221806A1 (fr)
WO (1) WO2003097707A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2022805A2 (fr) 2007-08-03 2009-02-11 Basf Se Copolymères à base de N- vinyllactams et oléfines pour leur utilisation en tant que stabilisateurs pour des composants légèrement solubles dans l'eau
WO2012039900A2 (fr) * 2010-09-23 2012-03-29 Shrieve Chemical Products, Inc. Copolymères de α-oléfine / vinylpyrrolidinone en tant que dispersants d'asphaltène

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3287272A (en) * 1964-05-18 1966-11-22 Gen Aniline & Film Corp Lubricating oil composition
US3423381A (en) * 1964-04-08 1969-01-21 Gaf Corp Simultaneous copolymerization and alkylation of heterocyclic n-vinyl monomers with alpha-olefins
US5026540A (en) * 1987-06-04 1991-06-25 Chesebrough-Pond's Usa Co. Sunscreen composition
DE10019470A1 (de) * 1999-04-22 2000-11-02 Nippon Catalytic Chem Ind Vinylpyrrolidon-Polymer und sein Stabilisierungs- und Konservierungsverfahren
WO2000078901A1 (fr) * 1999-06-21 2000-12-28 Quaker Chemical Corporation Fluides pour le travail des metaux

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3423381A (en) * 1964-04-08 1969-01-21 Gaf Corp Simultaneous copolymerization and alkylation of heterocyclic n-vinyl monomers with alpha-olefins
US3287272A (en) * 1964-05-18 1966-11-22 Gen Aniline & Film Corp Lubricating oil composition
US5026540A (en) * 1987-06-04 1991-06-25 Chesebrough-Pond's Usa Co. Sunscreen composition
DE10019470A1 (de) * 1999-04-22 2000-11-02 Nippon Catalytic Chem Ind Vinylpyrrolidon-Polymer und sein Stabilisierungs- und Konservierungsverfahren
WO2000078901A1 (fr) * 1999-06-21 2000-12-28 Quaker Chemical Corporation Fluides pour le travail des metaux

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2022805A2 (fr) 2007-08-03 2009-02-11 Basf Se Copolymères à base de N- vinyllactams et oléfines pour leur utilisation en tant que stabilisateurs pour des composants légèrement solubles dans l'eau
WO2012039900A2 (fr) * 2010-09-23 2012-03-29 Shrieve Chemical Products, Inc. Copolymères de α-oléfine / vinylpyrrolidinone en tant que dispersants d'asphaltène
WO2012039900A3 (fr) * 2010-09-23 2012-06-14 Shrieve Chemical Products, Inc. Copolymères de α-oléfine / vinylpyrrolidinone en tant que dispersants d'asphaltène

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DE10221806A1 (de) 2003-11-27
AU2003224155A1 (en) 2003-12-02

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