RU2017125059A - Способ получения сополимеров алкилметакрилатов и малеинового ангидрида - Google Patents
Способ получения сополимеров алкилметакрилатов и малеинового ангидрида Download PDFInfo
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- RU2017125059A RU2017125059A RU2017125059A RU2017125059A RU2017125059A RU 2017125059 A RU2017125059 A RU 2017125059A RU 2017125059 A RU2017125059 A RU 2017125059A RU 2017125059 A RU2017125059 A RU 2017125059A RU 2017125059 A RU2017125059 A RU 2017125059A
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- maleic anhydride
- alkyl methacrylates
- copolymer
- sulfur
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- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 title claims 11
- 238000004519 manufacturing process Methods 0.000 title 1
- -1 alkyl methacrylate Chemical compound 0.000 claims 12
- 238000000034 method Methods 0.000 claims 11
- 229920001577 copolymer Polymers 0.000 claims 8
- 238000006243 chemical reaction Methods 0.000 claims 5
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- 239000007870 radical polymerization initiator Substances 0.000 claims 3
- 239000002904 solvent Substances 0.000 claims 3
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 claims 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 2
- 239000000654 additive Substances 0.000 claims 2
- 230000000996 additive effect Effects 0.000 claims 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims 2
- 238000005227 gel permeation chromatography Methods 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 claims 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims 1
- 239000003208 petroleum Substances 0.000 claims 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 claims 1
- 238000006116 polymerization reaction Methods 0.000 claims 1
- 239000004926 polymethyl methacrylate Substances 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
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- C08F2/00—Processes of polymerisation
- C08F2/001—Multistage polymerisation processes characterised by a change in reactor conditions without deactivating the intermediate polymer
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08F2/00—Processes of polymerisation
- C08F2/04—Polymerisation in solution
- C08F2/06—Organic solvent
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- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1811—C10or C11-(Meth)acrylate, e.g. isodecyl (meth)acrylate, isobornyl (meth)acrylate or 2-naphthyl (meth)acrylate
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- 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
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1812—C12-(meth)acrylate, e.g. lauryl (meth)acrylate
-
- 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
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1818—C13or longer chain (meth)acrylate, e.g. stearyl (meth)acrylate
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- 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
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- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/18—Organic compounds containing oxygen
- C10L1/192—Macromolecular compounds
- C10L1/195—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- C10L1/196—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and a carboxyl group or salts, anhydrides or esters thereof homo- or copolymers of compounds having one or more unsaturated aliphatic radicals each having one carbon bond to carbon double bond, and at least one being terminated by a carboxyl radical or of salts, anhydrides or esters thereof
- C10L1/1966—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and a carboxyl group or salts, anhydrides or esters thereof homo- or copolymers of compounds having one or more unsaturated aliphatic radicals each having one carbon bond to carbon double bond, and at least one being terminated by a carboxyl radical or of salts, anhydrides or esters thereof poly-carboxylic
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- 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, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L10/00—Use of additives to fuels or fires for particular purposes
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M145/00—Lubricating compositions characterised by the additive being a macromolecular compound containing oxygen
- C10M145/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C10M145/10—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
- C10M145/16—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 polycarboxylic
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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
- 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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- 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
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- C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
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Claims (13)
1. Способ получения не содержащего серы сополимера, содержащего мономерные звенья на основе алкилметакрилата и мономерные звенья на основе малеинового ангидрида, посредством полимеризации в растворе одного или более алкилметакрилатов и малеинового ангидрида в растворителе в присутствии инициатора радикальной полимеризации, при этом указанный способ включает стадии:
a) получения исходного реакционного раствора, содержащего малеиновый ангидрид, часть инициатора радикальной полимеризации и растворитель,
b) добавления добавочного раствора, содержащего один или более алкилметакрилатов и часть инициатора радикальной полимеризации, к исходному реакционному раствору.
2. Способ по п. 1, отличающийся тем, что добавочный раствор добавляют в течение от 30 мин до 12 ч.
3. Способ по п. 1 или 2, отличающийся тем, что исходный реакционный раствор содержит от 50 до 100 вес.% малеинового ангидрида в пересчете на общее количество малеинового ангидрида.
4. Способ по п. 1 или 2, отличающийся тем, что молярное соотношение одного или более алкилметакрилатов и малеинового ангидрида находится в диапазоне от 10:1 до 1:1.
5. Способ по п. 1 или 2, отличающийся тем, что исходный реакционный раствор не содержит какого-либо алкилметакрилата.
6. Способ по п. 1 или 2, отличающийся тем, что часть одного или более алкилметакрилатов в добавочном растворе составляет от 50 до 100 вес.% в пересчете на общее количество одного или более алкилметакрилатов.
7. Способ по п. 1 или 2, отличающийся тем, что общее количество одного или более алкилметакрилатов и малеинового ангидрида находится в диапазоне от 10 до 80 вес.% относительно общего веса всего исходного реакционного раствора и добавочного раствора.
8. Способ по п. 1 или 2, отличающийся тем, что по меньшей мере 80 мол.% одного или более алкилметакрилатов выбраны из группы C6-C22алкилметакрилатов или их смеси.
9. Способ по п. 1 или 2, где весь растворитель или его часть выбраны из группы, состоящей из метилэтилкетона, изобутилметилкетона, анизола, н-бутанола, диметилформамида, диметилсульфоксида, бензола (петролейного эфира), ацетона, 1-гексена, этанола, ортоксилола и их смесей.
10. Не содержащий серы сополимер, полученный с помощью способа по любому из пп. 1-9, отличающийся тем, что среднечисловой молекулярный вес сополимера находится в диапазоне от 4000 до 18000 г/моль и коэффициент полидисперсности сополимера находится в диапазоне от 1 до 5, где среднечисловой молекулярный вес и коэффициент полидисперсности определены с помощью гель-проникающей хроматографии (GPC) относительно стандартов на основе поли(метилметакрилата), и молярное соотношение одного или более алкилметакрилатов и малеинового ангидрида в полученном сополимере находится в диапазоне от 10:1 до 1:1 в пересчете на общие молярные количества одного или более алкилметакрилатов и малеинового ангидрида, применяемых для получения не содержащего серы сополимера.
11. Не содержащий серы сополимер по п. 10, отличающийся тем, что не содержащий серы сополимер содержит эквимолярные количества одного или более алкилметакрилатов и малеинового ангидрида.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP14198775.0 | 2014-12-18 | ||
| EP14198775 | 2014-12-18 | ||
| PCT/EP2015/080085 WO2016097046A1 (en) | 2014-12-18 | 2015-12-16 | Method for the preparation of copolymers of alkyl methacrylates and maleic anhydride |
Publications (3)
| Publication Number | Publication Date |
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| RU2017125059A3 RU2017125059A3 (ru) | 2019-01-18 |
| RU2017125059A true RU2017125059A (ru) | 2019-01-18 |
| RU2692103C2 RU2692103C2 (ru) | 2019-06-21 |
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| RU2017125059A RU2692103C2 (ru) | 2014-12-18 | 2015-12-16 | Способ получения сополимеров алкилметакрилатов и малеинового ангидрида |
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| Country | Link |
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| US (1) | US10703840B2 (ru) |
| EP (1) | EP3233946B1 (ru) |
| JP (1) | JP6752793B2 (ru) |
| CN (1) | CN107108809B (ru) |
| CA (1) | CA2969053A1 (ru) |
| RU (1) | RU2692103C2 (ru) |
| SG (1) | SG11201704236VA (ru) |
| WO (1) | WO2016097046A1 (ru) |
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| SG11201704236VA (en) * | 2014-12-18 | 2017-07-28 | Evonik Oil Additives Gmbh | Method for the preparation of copolymers of alkyl methacrylates and maleic anhydride |
| RU2693383C2 (ru) * | 2014-12-18 | 2019-07-02 | Эвоник Оил Эддитивс Гмбх | Способ получения сополимеров алкилметакрилатов и малеинового ангидрида |
| CN111117496A (zh) * | 2020-01-16 | 2020-05-08 | 陕西省石油化工研究设计院 | 一种耐水型厌氧黏胶剂及其制备方法 |
| CN116731245B (zh) * | 2023-06-15 | 2024-04-02 | 长江大学 | 一种石油天然气清防蜡剂及其制备方法和应用 |
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| FR2566288B1 (fr) | 1984-06-21 | 1991-10-18 | Elf Aquitaine | Additifs polymeriques utilisables pour l'inhibition du depot de paraffines dans les huiles brutes |
| US5349019A (en) * | 1988-12-24 | 1994-09-20 | Hoechst | New copolymers, mixtures thereof with poly(meth)acrylate esters and the use thereof for improving the cold fluidity of crude oils |
| DE4036225A1 (de) * | 1990-11-14 | 1992-05-21 | Basf Ag | Erdoelmitteldestillate mit verbesserten fliesseigenschaften in der kaelte |
| DE59106537D1 (de) | 1990-12-20 | 1995-10-26 | Siemens Ag | Mischpolymere. |
| JPH06206944A (ja) | 1993-01-08 | 1994-07-26 | Hitachi Chem Co Ltd | 防汚塗料用樹脂の製造方法 |
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| US6140431A (en) * | 1997-02-27 | 2000-10-31 | Rohm And Haas Company | Process for preparing continuously variable-composition copolymers |
| JP2002531684A (ja) * | 1998-12-04 | 2002-09-24 | インフィニューム ホールディングス ベスローテン フェンノートシャップ | 燃料添加剤及び該燃料添加剤を含む燃料組成物 |
| US7378379B2 (en) * | 2003-06-10 | 2008-05-27 | The Lubrizol Corporation | Functionalized polymer composition for grease |
| CN1302031C (zh) | 2005-03-25 | 2007-02-28 | 泰山玻璃纤维股份有限公司 | 甲基丙烯酸十四酯－顺丁烯二酸酐共聚物的应用 |
| CN1328392C (zh) | 2005-09-23 | 2007-07-25 | 浙江大学 | 一种长链烷基防水加脂剂的制备方法 |
| FR2943678B1 (fr) * | 2009-03-25 | 2011-06-03 | Total Raffinage Marketing | Polymeres (meth)acryliques de bas poids moleculaire, exempts de composes soufres,metalliques et halogenes et de taux de monomeres residuels faible,leur procede de preparation et leurs utilisations |
| DE102009001964A1 (de) * | 2009-03-30 | 2010-10-07 | Evonik Röhm Gmbh | Multifunktionales(Meth)acryl-Polymer, Beschichtungszusammensetzung, Verfahren zur Herstellung einer Beschichtung und beschichteter Gegenstand |
| DE102010001040A1 (de) * | 2010-01-20 | 2011-07-21 | Evonik RohMax Additives GmbH, 64293 | (Meth)acrylat-Polymere zur Verbesserung des Viskositätsindexes |
| DE102010038615A1 (de) * | 2010-07-29 | 2012-02-02 | Evonik Rohmax Additives Gmbh | Polyalkyl(meth)acrylat zur Verbesserung von Schmieröleigenschaften |
| SG11201704236VA (en) * | 2014-12-18 | 2017-07-28 | Evonik Oil Additives Gmbh | Method for the preparation of copolymers of alkyl methacrylates and maleic anhydride |
| RU2693383C2 (ru) * | 2014-12-18 | 2019-07-02 | Эвоник Оил Эддитивс Гмбх | Способ получения сополимеров алкилметакрилатов и малеинового ангидрида |
-
2015
- 2015-12-16 SG SG11201704236VA patent/SG11201704236VA/en unknown
- 2015-12-16 CA CA2969053A patent/CA2969053A1/en not_active Abandoned
- 2015-12-16 JP JP2017532862A patent/JP6752793B2/ja not_active Expired - Fee Related
- 2015-12-16 EP EP15813369.4A patent/EP3233946B1/en active Active
- 2015-12-16 US US15/536,465 patent/US10703840B2/en active Active
- 2015-12-16 CN CN201580068822.6A patent/CN107108809B/zh active Active
- 2015-12-16 RU RU2017125059A patent/RU2692103C2/ru active
- 2015-12-16 WO PCT/EP2015/080085 patent/WO2016097046A1/en active Application Filing
Also Published As
| Publication number | Publication date |
|---|---|
| EP3233946B1 (en) | 2020-04-29 |
| RU2692103C2 (ru) | 2019-06-21 |
| SG11201704236VA (en) | 2017-07-28 |
| US20170362360A1 (en) | 2017-12-21 |
| CN107108809B (zh) | 2021-03-09 |
| WO2016097046A1 (en) | 2016-06-23 |
| US10703840B2 (en) | 2020-07-07 |
| JP6752793B2 (ja) | 2020-09-09 |
| EP3233946A1 (en) | 2017-10-25 |
| JP2017538834A (ja) | 2017-12-28 |
| CN107108809A (zh) | 2017-08-29 |
| CA2969053A1 (en) | 2016-06-23 |
| RU2017125059A3 (ru) | 2019-01-18 |
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