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EP2158186A1 - Composés ioniques contenant n - Google Patents

Composés ioniques contenant n

Info

Publication number
EP2158186A1
EP2158186A1 EP08773394A EP08773394A EP2158186A1 EP 2158186 A1 EP2158186 A1 EP 2158186A1 EP 08773394 A EP08773394 A EP 08773394A EP 08773394 A EP08773394 A EP 08773394A EP 2158186 A1 EP2158186 A1 EP 2158186A1
Authority
EP
European Patent Office
Prior art keywords
radicals
group
alkyl
atoms
cycloalkyl
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.)
Withdrawn
Application number
EP08773394A
Other languages
German (de)
English (en)
Inventor
Stefan Busch
Paul Birnbrich
Joachim Meyer
Ronald Klagge
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.)
Cognis IP Management GmbH
Original Assignee
Cognis IP Management GmbH
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 Cognis IP Management GmbH filed Critical Cognis IP Management GmbH
Publication of EP2158186A1 publication Critical patent/EP2158186A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/06—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
    • C07D233/08—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms with alkyl radicals, containing more than four carbon atoms, directly attached to ring carbon atoms
    • C07D233/10—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms with alkyl radicals, containing more than four carbon atoms, directly attached to ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring nitrogen 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
    • C08F2/00—Processes of polymerisation
    • C08F2/12—Polymerisation in non-solvents
    • C08F2/16—Aqueous medium
    • C08F2/22—Emulsion polymerisation
    • C08F2/24—Emulsion polymerisation with the aid of emulsifying agents
    • C08F2/28—Emulsion polymerisation with the aid of emulsifying agents cationic
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/32—Heterocyclic compounds

Definitions

  • the invention relates to ionic N-containing compounds of special structure and their use as temporary surfactants, in particular for the preparation of aqueous emulsions or dispersions.
  • Coalescing agents also called film-forming aids
  • They are added to aqueous coating materials and cause a film formation of the dispersing agent.
  • th polymer particles to a homogeneous paint film. Their addition is required if the film-forming temperature of the binder is above the application temperature.
  • Known film-forming aids are: ethylene glycol ethyl ether, ethylene glycol propyl ether, ethylene glycol butyl ether, ethylene glycol hexyl ether, diethylene glycol methyl ether, diethylene glycol ethyl ether, diethylene glycol butyl ether, diethylene glycol hexyl ether, propylene glycol n-butyl ether, dipropylene glycol n-butyl ether, dipropylene glycol methyl ether, tripropylene glycol methyl ether, propylene glycol phenyl ether, propylene glycol t-butyl ether, 2. 2,4-trimethyl-1,3-pentanediol mono-isobutyrate, 2,2,4-trimethyl-1,3-pentanediol diisobutyrate.
  • coalescents have been used in substantial quantities in latex coatings, which are based in particular on small particles of synthetic plastics such as polyacrylates.
  • These coalescing agents are added to the coatings to improve film formation.
  • the function is based on the fact that the coalescing agent softens the latex particles so that they flow together and form a continuous film.
  • This film has optimal film properties after the evaporation of the water.
  • the so-called film-forming temperature is important, in which (or above) the polymer particles flow together to form a film.
  • the usual coalescing agents lower the film forming temperature of the polymer.
  • the object of the present invention to provide novel temporary surfactants. These should be suitable in particular as emulsifiers or dispersants for emulsion polymerization.
  • the temporary surfactants to be developed should preferably also have the property that the nonionic compounds formed when the temporary surfactant is switched off are suitable as coalescing agents.
  • Another object of the present invention relates to the preparation of paints and coatings based on aqueous emulsions.
  • lacquer latexes are produced by emulsion polymerization.
  • a suitable surfactant is indispensable during the emulsion polymerization and the storage of the aqueous emulsion or dispersion until it is used, so that the polymerization takes place at all and thus the emulsion or dispersion prepared is stabilized, various undesirable characteristics of paint films such as low Water resistance attributed to remaining in the coating surfactant.
  • Another aspect of the present invention relates to the problem of remedy this situation.
  • radicals R 1 to R 3 independently of one another are hydrogen or alkyl, cycloalkyl or aryl radicals having 1 to 25 C atoms, where the alkyl radicals may be saturated or olefinically unsaturated, straight-chain or branched and the cycloalkyl radicals may be saturated or olefinically unsaturated , with the following provisos: (a) at least one of the radicals R 1 , R 2 or R 3 must have 8 to 25 C atoms, (b) in the radicals R 1 to R 3 , if these are alkyl or cycloalkyl radicals, optionally a hydrogen atom attached to a C atom is substituted by a group -OH or NH 2, or a group -O-, -COO- or -NH- is inserted between two adjacent C atoms linked via a C-C single bond, ( c) in the radicals R 1 to R 3 - if these aryl radicals are
  • the radical R 1 is preferably a saturated or olefinically unsaturated alkyl radical having 8 to 25 C atoms.
  • the radical R 1 is a saturated or olefinically unsaturated alkyl radical having 8 to 25 C atoms and the radicals R 2 and R 3 are each hydrogen.
  • the compounds (I) or (Ia) can be prepared by all methods known to those skilled in the art, for example by reacting N-containing compounds of the general formula (II) or (II-a) with CO 2 in the presence of water.
  • the compounds (II) can be prepared by all methods known to the person skilled in the art, for example by reacting corresponding 1,2-diamines or 1,3-diamines with fatty acids.
  • suitable 1,2-diamines are ethylenediamine and propylenediamine.
  • 1,3-diamine is about 1,3-diaminopropane.
  • Suitable fatty acids are the saturated fatty acids hexanoic acid (caproic acid), heptanoic acid, octanoic acid (caprylic acid), nonanoic acid (pelargonic acid), decanoic acid (capric acid), undecanoic acid, dodecanoic acid (lauric acid), tridecanoic acid, Tetradecanoic acid (myristic acid), pentadecanoic acid, hexadecanoic acid (palmitic acid), heptadecanoic acid, oxadecanoic acid (stearic acid), nonadecanoic acid, eicosanoic acid (arachic acid), dodecanoic acid (behenic acid) and the olefinically unsaturated fatty acids 10- undecenoic acid, lauroleinic acid, myristoleic acid, palmitoleic acid, petroselinic acid, oleic acid , Elaidic acid, linoleic acid,
  • R 1 to R 3 have the same meaning as in the above
  • the compounds (II-a) represent imidazoline derivatives.
  • the radicals R 1 , R 2 , R 3 and R 5 have the same meaning as in the above formula (Ia). These compounds can be prepared, for example, from N-substituted 1,2-diamines.
  • a further subject of the invention is the use of the compounds (I) as temporary (switchable) surfactants, in particular as temporary surfactants for the preparation of aqueous emulsions or dispersions and very particularly preferably as temporary surfactants in the emulsion polymerization. In this case, the switching between the ionic surfactant (I) and the resulting by elimination of CO 2 nonionic compounds (II)
  • Atoms a group -O-, -COO- or -NH- used (b) in radicals R 1 to R 5 if these aryl radicals are present, it is optionally possible for a hydrogen atom connected to a C atom to be substituted by an alkyl or cycloalkyl group having from 1 to 12 C atoms, with Stipulation that for this Alkyl or cycloalkyl group: if appropriate, a hydrogen atom attached to a carbon atom can be substituted by a group -OH or NH 2, or a group -O-, -COO- or - is attached between two adjacent carbon atoms linked via a single carbon-carbon bond NH- inserted, by means of an inert gas, for example nitrogen or argon, causes.
  • an inert gas for example nitrogen or argon
  • the compounds (I) to be used according to the invention as temporary surfactants can be used in pure form or in the form of mixtures with one another. If desired, it is also possible to use the compounds (I) in combination with other surfactants.
  • Another subject of the invention is a process for the preparation of coatings based on aqueous polymer or latex dispersions, which comprises preparing the aqueous polymer or latex dispersions using the above-defined temporary surfactants (I) as emulsifiers and the temporary surfactants (I) when applying the aqueous polymer or latex dispersions by cleavage of CO 2 in the above-defined non-surfactant compounds (II) transferred, which then serve as a coalescing agent.
  • coalescing agents also referred to in the literature as filming assistants or film-forming aids
  • filming assistants or film-forming aids are to be understood in the sense which is well-known to those skilled in the art and described above.
  • aqueous dispersions may contain further additives and additives known to those skilled in the art, depending on the desired application or the type of coating.
  • aqueous dispersions containing temporary surfactants (I) to be used according to the invention can, in principle, be applied to any surfaces, for example wood, metal, plastic, glass, paper, concrete, masonry and plasters.
  • Example 1 a) Preparation of imidazoline 150 g (2.5 mol) of ethylenediamine were heated in a 4-necked flask with stirrer, dropping funnel and reflux condenser and under reflux 279 g (1 mol) of oleic acid (Edenor T105, Cognis) dosed within 3 hours. After distillative removal of the water of reaction (18 g) and the excess ethylenediamine, the imidazoline was obtained as a slightly yellow solid. The yellow coloration was due to unseparated ethylenediamine.
  • the ionic surfactant can be termed temporary, since it can be converted back into the imidazoline by splitting off CO 2 (switching off the ionic surfactant).

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Paints Or Removers (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne des composés ioniques contenant N de formule générale (I), dans laquelle l'indice n représente le chiffre 0 ou 1 et les radicaux R1 à R5 représentent indépendamment les uns des autres l'hydrogène ou des radicaux alkyle, cycloalkyle ou aryle ayant 1 à 25 atomes C, les radicaux alkyle pouvant être saturés ou oléfiniquement insaturés, à chaîne linéaire ou ramifiés et les radicaux cycloalkyle pouvant être saturés ou oléfiniquement insaturés, avec les conditions suivantes : (1) si n = 1, au moins un des radicaux R1 à R5 doit avoir 8 à 25 atomes C, (2) si n = 0, au moins un des radicaux R1, R2, R3 ou R5 doit avoir 8 à 25 atomes C, (3) les atomes C qui portent les radicaux R2 et R3 sont reliés par une liaison C-C simple ou une liaison C=C double, (4) dans les radicaux R1 à R5, si ces radicaux sont des radicaux alkyle ou cycloalkyle, un atome d'hydrogène relié à un atome C peut éventuellement être remplacé par un groupement -OH ou NH2 ou un groupement -O-, -COO- ou -NH- peut être interposé entre deux atomes C voisins et reliés par une liaison C-C simple, (5) dans les radicaux R1 à R5, si ces radicaux sont des radicaux aryle, un atome d'hydrogène relié à un atome C peut éventuellement être remplacé par un groupement alkyle ou cycloalkyle ayant 1 à 12 atomes C, à condition que pour ce groupement alkyle ou cycloalkyle : un atome d'hydrogène relié à un atome C peut éventuellement être remplacé par un groupement -OH ou NH2 ou un groupement -O-, -COO- ou -NH- peut être interposé entre deux atomes C voisins et reliés par une liaison C-C simple, utiles en tant que tensioactifs temporaires, notamment pour la fabrication d'émulsions ou de dispersions aqueuses.
EP08773394A 2007-06-21 2008-06-12 Composés ioniques contenant n Withdrawn EP2158186A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102007028714A DE102007028714A1 (de) 2007-06-21 2007-06-21 Ionische N-haltige Verbindungen
PCT/EP2008/004700 WO2008155058A1 (fr) 2007-06-21 2008-06-12 Composés ioniques contenant n

Publications (1)

Publication Number Publication Date
EP2158186A1 true EP2158186A1 (fr) 2010-03-03

Family

ID=39776385

Family Applications (1)

Application Number Title Priority Date Filing Date
EP08773394A Withdrawn EP2158186A1 (fr) 2007-06-21 2008-06-12 Composés ioniques contenant n

Country Status (6)

Country Link
US (1) US20100179260A1 (fr)
EP (1) EP2158186A1 (fr)
JP (1) JP2010530388A (fr)
CN (1) CN101679289A (fr)
DE (1) DE102007028714A1 (fr)
WO (1) WO2008155058A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112302588A (zh) * 2019-07-15 2021-02-02 中国石油化工股份有限公司 采用咪唑啉化合物降低co2驱最小混相压力的方法

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2839371A (en) * 1954-04-08 1958-06-17 California Research Corp Gasoline composition
US6121457A (en) * 1997-11-14 2000-09-19 Megabios Corporation Compositions and methods using novel substituted imidazolium lipids
US20060128601A1 (en) * 2002-01-09 2006-06-15 Croda, Inc. Imidazoline quats
CA2527144C (fr) * 2005-11-15 2014-04-29 Queen's University At Kingston Surfactants reversibles, et methodes d'utilisation

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2008155058A1 *

Also Published As

Publication number Publication date
US20100179260A1 (en) 2010-07-15
WO2008155058A1 (fr) 2008-12-24
JP2010530388A (ja) 2010-09-09
CN101679289A (zh) 2010-03-24
DE102007028714A1 (de) 2008-12-24

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