EP1819678A1 - Diimides d'acide tetracarboxylique de rylene substitues par des groupes amino cycliques - Google Patents

Diimides d'acide tetracarboxylique de rylene substitues par des groupes amino cycliques

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Publication number
EP1819678A1
EP1819678A1 EP05810887A EP05810887A EP1819678A1 EP 1819678 A1 EP1819678 A1 EP 1819678A1 EP 05810887 A EP05810887 A EP 05810887A EP 05810887 A EP05810887 A EP 05810887A EP 1819678 A1 EP1819678 A1 EP 1819678A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
substituted
alkoxy
interrupted
aryl
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.)
Ceased
Application number
EP05810887A
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German (de)
English (en)
Inventor
Martin KÖNEMANN
Jianqiang Qu
Klaus MÜLLEN
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.)
BASF SE
Original Assignee
BASF SE
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Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Publication of EP1819678A1 publication Critical patent/EP1819678A1/fr
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/06—Peri-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
    • C09B5/62—Cyclic imides or amidines of peri-dicarboxylic acids of the anthracene, benzanthrene, or perylene series
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/04—Ortho- or peri-condensed ring systems
    • C07D221/18—Ring systems of four or more rings

Definitions

  • the present invention relates to novel Rylenetetracarbonklarediimide of the general formula I.
  • -SO 2 - may be interrupted and which may be monosubstituted or polysubstituted by:
  • R 1 is hydrogen or C 1 -C 18 -alkyl, where the radicals R 1 may be identical or different if they occur more than once;
  • R 2 , R 3 are independently hydrogen;
  • -O-, -S-, -CO-, -SO- and / or -SO 2 - may be interrupted and the one or more times by C 1 -C 12 -Akoxy 1 C r C 6 alkylthio, hydroxy, mercapto , Halogen, cyano, nitro and / or -COOR 1 may be substituted;
  • Aryl or hetaryl, to each of which further saturated or unsaturated 5- to 7-membered rings, whose carbon skeleton may be interrupted by one or more groups -O-, -S-, -CO- and / or -SO 2 - be annelated can, with the entire ring system one or more times by C 1 -Ci 2 - Alkyl and / or the above, as substituents for alkyl mentioned radicals can be substituted;
  • C 1 -C 30 -alkyl whose carbon chain may be interrupted by one or more groups -O-, -S-, -NR 1 -, -CO- and / or -SO 2 - and which may be interrupted by cyano, hydroxy, nitro, C 1 -C 6 -alkoxy, -COOR 2, -CONR 2 R 3, aryl substituted by C 1 - 1 -C 6 -alkoxy can be substituted C 18 alkyl or C, and / or bonded via a nitrogen atom 5- to 7-membered heterocyclic radical containing further heteroatoms and may be aromatic, mono- or polysubstituted;
  • C 5 -C 8 -cycloalkyl whose carbon skeleton may be interrupted by one or more groups -O-, -S- and / or -NR 1 - and / or which may be mono- or polysubstituted by C 1 -C 6 -alkyl;
  • Aryl or hetaryl each by CrC 18 alkyl, Ci-C 6 alkoxy, cyano, nitro, halogen, -CONR 2 R 3 , -NR 2 COR 3 , -SO 2 NR 2 R 3 and / or aryl or Hetarylazo, which may be substituted in each case by C 1 -C 10 -AIRyI, C 1 -C 6 -alkoxy or cyano, may be mono- or polysubstituted, and where the radicals A may be the same or different for m>1;
  • X is chlorine or bromine, where the radicals X may be the same or different for x> 1;
  • ZC 3 -C 20 -alkyl, C 3 -C 20 -alken-2-yl or C 3 -C 2 o-alkyn-2-yl, whose alkyl chain is in each case represented by one or more groups -O-, -S-, - NR 1 -, -CO- and / or -SO 2 - may be interrupted and by cyano, C 1 -C 6 -alkoxy, -COOR 2 ,
  • aryl which may be substituted by C 1 -C 18 -alkyl or C 1 -C 6 -alkoxy, and / or a 5- to 7-membered heterocyclic radical bonded via a nitrogen atom and containing further heteroatoms may be aromatic, mono- or polysubstituted;
  • the invention relates to the preparation of these Rylenetetracarbonklarediimide and their use for coloring organic and inorganic materials, in particular paints, printing inks and plastics, as dispersants and pigment additives for organic pigments, for production in the near-infrared region of the electromagnetic spectrum absorbing aqueous polymer dispersions, for the production of the human eye of invisible infrared-absorbing markers and labels and as an infrared absorber for thermal management.
  • rylenetetracarboxylic diimides (referred to below as “rylenimides” for short) are known to be of particular application-related interest because of their strong absorption in the near-infrared region of the electromagnetic spectrum.
  • rylenimides referred to below as "rylenimides” for short
  • WO-A-02/77081 describes the use of quaterrylenetetracarboxylic diimides as infrared absorbers for thermal protection in glass laminates.
  • Rylenimiden based on terrylene and quaterrylene such Rylenimide are known which carry halogen, aryloxy, arylthio, hetaryloxy, hetarylthio, alkyl, alkenyl or alkynyl as substituents on the rylene skeleton (Chem. Eur. J. 3, 219-225 (1997) WO-A-03/104232; WO-A-96/22332; Angew. Chem. 107, 1487-1489 (1995); WO-A-02/76988).
  • Tetrahedron Letters 40, 7047-7050 (1999) discloses N, N'-dicyclohexylperylene-S, N, O-tetracarboxylic diimides bearing 2 pyrrolidyl, piperidyl or morpholinyl radicals in the perylene skeleton.
  • R, R 1 , A, Z and m have the meaning given at the outset and n1 and z1 have the following meanings:
  • Rylenimide I for coloring high molecular weight organic and inorganic materials, as a dispersing aid and pigment additives for organic pigments, for production in the near-infrared region of the electrical magnetic spectrum of absorbing aqueous polymer dispersions, for generating invisible to the human eye, infrared light absorbing markers and found as infrared absorbers for thermal management.
  • Carboxymethyl 2-carboxyethyl, 3-carboxypropyl, 4-carboxybutyl, 5-carboxypentyl, 6-carboxyhexyl, 8-carboxyctyl, 10-carboxydecyl, 12-carboxydodecyl and 14-carboxytetradecyl;
  • Sulfomethyl 2-sulfoethyl, 3-sulfopropyl, 4-sulfobutyl, 5-sulfopentyl, 6-sulfohexyl, 8-sulfooctyl, 10-sulfodecyl, 12-sulfododecyl and 14-sulfotetradecyl;
  • Aminosulfonyl N, N-dimethylaminosulfonyl, N, N-diethylaminosulfonyl, N, N-dipropylaminosulfonyl, N, N-diisopropylaminosulfonyl, N, N-dibutylaminosulfonyl, N, N-diisobutylaminosulfonyl, N, N'-di-sec-butylaminosulfonyl , NN-di-tert-butylaminosulfonyl, N, N-Dipentylaminosulfonyl, N, N-Dihexylaminosulfonyl, NN-Diheptylaminosulfonyl, N, N-Dioctylaminosulfonyl, N, N-Dinonylaminosulfonyl, N, N-Didecylaminosul
  • the terryleneimides I according to the invention can carry up to 6 substituents in the terrylene skeleton, preferably 4 or 2 substituents.
  • the quaterryleneimides I according to the invention can have up to 8 substituents in the quaterrylene skeleton; preferably 6, 4 or 2 substituents.
  • the rylene skeletons are preferably substituted by at least 2 cyclic amino radicals A which, as a constituent of the chromophoric system, cause an unexpectedly strong bathochromic shift of absorption and emission, which is about 110 nm for the terryleneimides and about 60 nm for the quaterryleneimides non-substituted or substituted by other radicals Rylenimiden.
  • the rylenimides according to the invention are generally produced in the form of product mixtures with different degrees of substitution which, if desired, can be separated by chromatography.
  • the preparation of the inventive rylenimides Ia which are substituted exclusively by the cyclic amino radicals A, can advantageously be carried out by reacting the halogenated, preferably chlorinated and particularly preferably brominated, rylenimides IIa with the corresponding amine III.
  • halogenated rylenimides IIa and their preparation are known from WO-A-03/104232, 96/22332 and 02/76988 and the earlier German patent application 102004048729.4.
  • the rylenimides Ib according to the invention which are substituted in the rylene skeleton both by the cyclic amine radicals A and by (Het) aryloxy and / or (Het) arylthio radicals Z, can be prepared starting from rylenimides IIb, which are already substituted by the radicals Z. and further halogen atoms X carry for exchange with the cyclic amino radicals A.
  • the rylenimides IIb are likewise known from the abovementioned WO-A-03/104232, 96/22332 and 02/76988 and are obtainable from the halogenated rylenimides IIa by incomplete replacement of the halogen atoms X by the radicals Z.
  • Rylenimides I according to the invention which carry cyclic amino radicals A, (Het) aryloxy and / or (Het) arylthio radicals Z and halogen atoms X or cyclic amino radicals A and halogen atoms X in the rylene skeleton are analogous in each case by incomplete replacement of the halogen atoms X by the amino radicals A and if appropriate, the radicals Z are available.
  • these rylenimides I are only of minor importance.
  • a non-acidic solvent may be present as the reaction medium, but the amine III may also itself act as a solvent.
  • Particularly suitable cyclic amines III are piperidines, pyrrolidines, piperazines, morpholines and thiomorpholines (1,4-thiazines), the piperidines, pyrrolidines, piperazines and morpholines being preferred and the piperidines being particularly preferred.
  • the cyclic amines III can be chemically modified, ie their carbon chain can be interrupted not only by -O-, -S- or -NR 1 - but also by -CO-, -SO- or -SO 2 -, they can be a or two aromatic or saturated 4- to 7-membered fused rings whose carbon chain may also be interrupted by said groups, and they may be substituted by the above-mentioned alkyl, cycloalkyl and / or (Het) aryl radicals.
  • the unmodified amines III are preferred.
  • Piperidine 2- or 3-methylpiperidine, 6-ethylpiperidine, 2,6- or 3,5-dimethylpiperidine, 2,2,6,6-tetramethylpiperidine, 4-benzylpiperidine, 4-phenylpiperidine, piperidin-4-ol, piperidine pyridine-4-carboxylic acid, piperidine-4-carboxylic acid methyl ester, piperidine-4-carboxylic acid ethyl ester, piperidine-4-carboxylic acid amide, 2,2,6,6-tetramethylpiperidin-4-one, 2,2,6,6-tetramethylpiperidine 4-ylamine, decahydroquinoline and decahydroisoquinoline;
  • Piperazine diketopiperazine, 1-benzylpiperazine, 1-phenethylpiperazine, 1-cyclohexylpiperazine, 1-phenylpiperazine, 1- (2,4-dimethylphenyl) piperazine, 1- (2-, 3- or 4-methoxyphenyl) -piperazine, 1- (2-, 3- or 4-ethoxyphenyl) piperazine, 1- (2-, 3- or 4-fluorophenyl) piperazine, 1- (2-, 3- or 4-chlorophenyl) piperazine, 1- ( 2-, 3- or 4-bromophenyl) piperazine, 1-, 2- or 3-pyridin-2-ylpiperazine and 1-benzo [1,3] dioxol-4-ylmethylpiperazine;
  • salts e.g. the salts of inorganic acids, such as the hydrofluorides, hydrochlorides, hydrobromides, hydroiodides, hydrogen sulfates, hydrogen sulfites, Hydrogenphoshate and hydrogen phosphites, or the salts of organic acids, such as the formates, acetates and propionates, are used, from which by addition of base again the amines are released.
  • inorganic acids such as the hydrofluorides, hydrochlorides, hydrobromides, hydroiodides, hydrogen sulfates, hydrogen sulfites, Hydrogenphoshate and hydrogen phosphites
  • organic acids such as the formates, acetates and propionates
  • the cyclic amine III is used only as a reactant and not as a solvent at the same time, its amount used is usually from 1 to 10 mol, in particular from 1 to 3 mol, per halogen atom to be exchanged in the rylenimide IIa or IIb.
  • Suitable bases are, under the reaction conditions, liquid trialkylamines, in particular tri (C 3 -C 6 -alkyl) amines, such as tripropylamine and tributylamine, and especially nitrogen-containing heterocycles, such as pyridine, N-methylpiperidine, N-methylmorpholine, pyrimidine, quinoline , Isoquinoline, quinaldine, diazabicyclononene (DBN) and diazabicycloundecene (DBU).
  • liquid trialkylamines in particular tri (C 3 -C 6 -alkyl) amines, such as tripropylamine and tributylamine
  • nitrogen-containing heterocycles such as pyridine, N-methylpiperidine, N-methylmorpholine, pyrimidine, quinoline , Isoquinoline, quinaldine, diazabicyclononene (DBN) and diazabicycloundecene (DBU).
  • a non-nucleophilic base is used, its amount is generally 1 to 5 mol, preferably 1 to 3 mol, per halogen atom to be exchanged in the rylenimide IIa or IIb.
  • Suitable solvents for the reaction according to the invention of the halogenated rylenimide IIa or IIb with the cyclic amine III are non-acidic solvents which do not protonate the amine III.
  • One group of preferred solvents are aliphatic carboxylic acid amides, especially N, N-di (C 1 -C 6 alkyl) - (Ci-C 6 carboxylic acid) amides such as N, N-dimethylformamide, N 1 N-diethylformamide, N, N-dimethylacetamide and N, N-dimethylbutyramide, and lactams, in particular N- (C 1 -C 6 -alkyl) lactams, such as N-methylpyrrolidone, with dimethylformamide and N-methylpyrrolidone being particularly preferred.
  • N-di (C 1 -C 6 alkyl) - (Ci-C 6 carboxylic acid) amides such as N, N-dimethylformamide, N 1 N-diethylformamide, N, N-dimethylacetamide and N, N-dimethylbutyramide
  • lactams in particular N- (C 1 -C 6 -al
  • halogenated aromatic and aliphatic hydrocarbons such as chlorobenzene, dichlorobenzene and trichlorobenzene, and halogenated methanes and ethanes, for example methylene chloride, chloroform, tribromomethane, tetrachloromethane, tetrabromomethane, 1, 2-dichloro, 1,1- and 1 , 2-dibromo, 1, 1, 1 and 1, 1, 2-trichloro, 1, 1, 1 and 1,1, 2-tribromo, 1, 1, 1, 1, 2 and 1, 1 , 2,2-tetrachloro and 1, 1,1, 2- and 1, 1, 2,2-tetrabromoethane, with methylene chloride, chloroform and chlorobenzene being particularly preferred.
  • the amount of solvent is selected in the process according to the invention so that generally 10 to 100 g, preferably 10 to 50 g, of a liquid phase under the reaction conditions per g of halogenated Rylenimid IIa or IIb are present.
  • the liquid phase is composed of the nonacidic solvent and the cyclic amine III or, if the cyclic amine III simultaneously acts as a solvent, of the amine IM alone and optionally the non-nucleophilic base.
  • the reaction temperature in the process according to the invention is generally from 30 to 200 ° C., preferably from 50 to 150 ° C.
  • the reaction time is usually 12 h to 10 d, in particular 1 to 5 d.
  • a mixture of rylenimide IIa or IIb and cyclic amine III and, if desired, nonacid solvent and / or nonnucleophilic base are heated to the chosen reaction temperature and stirred at this temperature for 12 h to 10 d.
  • the workup of the reaction mixture on the Rylenimide I can be done by filtering off the possibly precipitated reaction product or evaporation and subsequent column filtration or column chromatography.
  • protic solvents such as water, alcohols, in particular Ci-C 6 alkanols, for example methanol, ethanol, n- and i-propanol, n-, i- and sec-butanol, n-pentanol, amyl alcohol and n- and i-hexanol, ethylene glycol mono (C r C 4 alkyl) ether, for example ethylene glycol mono-n-butyl ether, and carboxylic acids, in particular aliphatic Ci-C 4 -carboxylic acids, for example formic acid, acetic acid, propionic acid and butyric acid ,
  • reaction product subsequently isolated by filtration or by evaporation is usually washed with one of these solvents or a dilute inorganic acid, such as sulfuric acid, hydrochloric acid or phosphoric acid, or a combination of solvents, or stirred in these solvents and filtered again.
  • a dilute inorganic acid such as sulfuric acid, hydrochloric acid or phosphoric acid, or a combination of solvents
  • recrystallization may be carried out from the chlorinated hydrocarbons or carboxylic acid amides and lactams mentioned as reaction solvents, optionally in combination with the solvents suitable for precipitation or dilute inorganic acids.
  • the reaction product can be further purified.
  • the rylenimides I of the different degrees of substitution can be separated from one another.
  • Suitable eluents for the above-mentioned chlorinated hydrocarbons, with chloroform and methylene chloride are preferred, are, as well as mixtures of esters, such as ethyl acetate, and / or alcohols, for example methanol or ethanol, and aliphatic rule hydrocarbons, for example petroleum ethers with a boiling range 35-120 0 C, or aromatic hydrocarbons, for example benzene, toluene, xylenes, mesitylene and ethylbenzene.
  • Silica gel is usually used as the stationary phase.
  • the rylenimides I can be obtained in yields of generally from 30 to 90% and purities of at least 90%.
  • the rylenimides I according to the invention exhibit strong absorption in the near infrared range at wavelengths of up to 1100 nm and thus advantageously supplement the spectral range accessible with the aid of the hitherto known rylene compounds.
  • organic and inorganic materials such as paints, printing inks and plastics, as dispersing agents and pigment additives for organic pigments, for production in the near-infrared region of the electromagnetic spectrum absorbing aqueous polymer dispersions, for the production of the human eye invisible, infrared absorbing markers and markings, and as an infrared absorber for thermal management.
  • ⁇ m a x ( ⁇ ) (methylene chloride) 791 nm (53 l g '1 cm -1 ).
  • ⁇ m a x ( ⁇ ) (methylene chloride) 805 nm (61 l g '1 cm -1 ).
  • reaction mixture was then added to a mixture of 100 ml of water and 100 ml of methanol and stirred at room temperature for 30 minutes before filtration.
  • the moist presscake was stirred in 50 ml of 1m hydrochloric acid for 30 min, filtered off, then stirred in 100 ml of water / methanol (1: 1 v / v), filtered off and dried in vacuo.
  • reaction mixture After cooling to 8O 0 C, the reaction mixture was precipitated to 500 ml of water. The mixture was stirred at 8O 0 C for 3 h. The precipitated reaction product was filtered off, washed with warm water and then dried in vacuo.
  • ⁇ m ax ( ⁇ ) (methylene chloride) 877 nm (51 l g -1 cm -1 ).

Abstract

L'invention concerne des diimides d'acide tétracarboxylique de rylène de formule (I). Cette invention concerne également la production de ces diimides d'acide tétracarboxylique de rylène et leur utilisation dans la coloration de matières organiques et inorganiques, en particulier de laques, d'encres d'imprimerie et de matières plastiques, comme auxiliaires de dispersion et additifs pour pigments organiques, dans la production de dispersions de polymères aqueuses à absorption dans la région proche infrarouge du spectre électromagnétique, dans la production de marquages et d'inscriptions absorbant la lumière infrarouge, invisibles à l'oeil humain, et comme absorbeurs d'infrarouge pour la gestion de la chaleur.
EP05810887A 2004-11-29 2005-11-26 Diimides d'acide tetracarboxylique de rylene substitues par des groupes amino cycliques Ceased EP1819678A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102004057585A DE102004057585A1 (de) 2004-11-29 2004-11-29 Durch cyclische Aminogruppen substituierte Rylentetracarbonsäurediimide
PCT/EP2005/012661 WO2006058674A1 (fr) 2004-11-29 2005-11-26 Diimides d'acide tetracarboxylique de rylene substitues par des groupes amino cycliques

Publications (1)

Publication Number Publication Date
EP1819678A1 true EP1819678A1 (fr) 2007-08-22

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Family Applications (1)

Application Number Title Priority Date Filing Date
EP05810887A Ceased EP1819678A1 (fr) 2004-11-29 2005-11-26 Diimides d'acide tetracarboxylique de rylene substitues par des groupes amino cycliques

Country Status (7)

Country Link
US (1) US20090124732A1 (fr)
EP (1) EP1819678A1 (fr)
JP (1) JP2008521766A (fr)
KR (1) KR20070090200A (fr)
CN (1) CN101068790A (fr)
DE (1) DE102004057585A1 (fr)
WO (1) WO2006058674A1 (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102005032583A1 (de) 2005-07-11 2007-01-25 Basf Ag Substituierte Rylenderivate
WO2009000831A1 (fr) * 2007-06-25 2008-12-31 Basf Se Dérivés d'acide rylène tétracarboxylique substitués par brome et leur utilisation
DE102007030076A1 (de) 2007-06-29 2007-11-15 Heidelberger Druckmaschinen Ag Verfahren zum Trocknen von Druckfarbe auf einem Bedruckstoff
CN101939352B (zh) * 2008-02-05 2014-04-16 巴斯夫欧洲公司 由萘嵌苯(rylene)-(π-受体)共聚物制备的半导体材料
EP3858946A1 (fr) 2020-01-29 2021-08-04 Basf Se Nouveaux rylènedicarboximides

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Publication number Priority date Publication date Assignee Title
DE10225595A1 (de) * 2002-06-07 2003-12-18 Basf Ag 1,6,9,14-Tetrasubstituierte Terrylentetracarbonsäurediimide

Non-Patent Citations (1)

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Title
See references of WO2006058674A1 *

Also Published As

Publication number Publication date
WO2006058674A1 (fr) 2006-06-08
US20090124732A1 (en) 2009-05-14
KR20070090200A (ko) 2007-09-05
CN101068790A (zh) 2007-11-07
DE102004057585A1 (de) 2006-06-01
JP2008521766A (ja) 2008-06-26

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