EP0635005A1 - Derives de l'acide acetique et de l'acide amino-3-acrylique contenant des groupes polyalkylpiperidine - Google Patents

Derives de l'acide acetique et de l'acide amino-3-acrylique contenant des groupes polyalkylpiperidine

Info

Publication number
EP0635005A1
EP0635005A1 EP93908853A EP93908853A EP0635005A1 EP 0635005 A1 EP0635005 A1 EP 0635005A1 EP 93908853 A EP93908853 A EP 93908853A EP 93908853 A EP93908853 A EP 93908853A EP 0635005 A1 EP0635005 A1 EP 0635005A1
Authority
EP
European Patent Office
Prior art keywords
groups
formula
alkyl
phenyl
radical
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Withdrawn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
EP93908853A
Other languages
German (de)
English (en)
Inventor
Martin Holderbaum
Alexander Aumueller
Hubert Trauth
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
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 SE filed Critical BASF SE
Publication of EP0635005A1 publication Critical patent/EP0635005A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D211/40—Oxygen atoms
    • C07D211/44—Oxygen atoms attached in position 4
    • C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/92—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with a hetero atom directly attached to the ring nitrogen atom
    • C07D211/94—Oxygen atom, e.g. piperidine N-oxide
    • 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
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
    • C08K5/3432—Six-membered rings
    • C08K5/3435—Piperidines
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/48—Stabilisers against degradation by oxygen, light or heat

Definitions

  • the present invention relates to novel polyalkylpiperidine group-containing acetic acid and 3-aminoacrylic acid derivatives I
  • R 1 is hydrogen, C 1 -C 1 -alkyl, formyl, C 2 - to
  • R 3 is hydrogen, -C ⁇ to C ß alkyl or a radical of the formula -CO-OR 4 and
  • R 4 Ci to C 20 alkyl, C 5 to Cs cycloalkyl, C 7 to
  • R 2 cyano, a radical of the formula -CO-R 5 or -CO-OR 5 or a group of the formula
  • R 5 is C-- to -C 2 alkyl, C 5 - to Cs-cycloalkyl, benzyl, phenyl or tolyl,
  • X represents 0, NH or NR ⁇ , where
  • R 6 means Ci to -C 2 alkyl
  • R 7 is phenyl which groups 2 alkyl substituted by one to three C ⁇ ⁇ to C ⁇ , C ⁇ ⁇ C ⁇ to groups 2 alkoxy groups, halogen atoms, cyano groups, hydroxyl groups, phenyl groups or groups of the formula -CO-OR 5, -CO-R 5 , -CO-NHR 5 , -0-CO-R 5 or -NH-CO-R 5 may be substituted, a five- or six-membered unsaturated or saturated heterocyclic ring with up to three heteroatoms from the group nitrogen, oxygen and sulfur be additionally comprising benzo- fused and up C ⁇ pen 2 -Alkylgrup- by one to three C ⁇ ⁇ pen C ⁇ ⁇ to C ⁇ 2 alkoxy groups, halogen atoms, Cyanogrup ⁇ , hydroxyl groups, phenyl groups, phenoxy groups or C to C 2 alkoxycarbonyl groups substituted can, or - in the event that at least one variable X is
  • the invention relates to compounds I stabilized against the action of light, oxygen and heat, organic material, in particular stabilized plastics and paints.
  • organic material especially plastics and paints
  • This destruction is usually manifested in yellowing, discoloration, cracking or embrittlement of the material. Satisfactory protection against the destruction of organic material by light, oxygen and heat should therefore be achieved with light stabilizers and stabilizers.
  • DE-A 38 05 786 (2) relates to 3- (polyalkylpiperidinylamino) acrylic acid polyalkylpiperidinyl esters. These compounds are recommended as stabilizers for organic material, especially synthetic polymers.
  • R 1 , R 3 to R 6 , R 8 as substituents on the phenyl nucleus and on heterocyclic rings and as an alcohol radical in alkoxycarbonyl groups, which are known as Ci to C 4 , C 1 to C 4 , C 4 ⁇ to C 12 - and C ⁇ ⁇ to C 2 o-alkyl radicals are suitable, for example, methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-amyl, iso-amyl, sec.-amyl, tert.-amyl, neopentyl, n-hexyl, n-heptyl, n-octyl, 2-ethyl hexyl, n-nonyl, iso-nonyl, n-
  • Suitable straight-chain or branched C 2 -C 6 -alkanoyl for R 1 are acetyl in particular, but also propionyl, butyryl, isobutyryl, pentanoyl and hexanoyl.
  • C ⁇ ⁇ to C ⁇ 2 alkoxy groups for R 1 and as substituents on the phenyl nucleus and on heterocyclic rings are especially C ⁇ ⁇ to C 4 alkoxy groups such as methoxy, ethoxy, n-propoxy, iso-propoxy , n-butoxy, iso-butoxy, sec-butoxy and tert-butoxy, but also n-pentoxy, n-hexoxy, iso-hexoxy, n-heptoxy, iso-heptoxy, n-octoxy, 2-ethylhexoxy, iso-octoxy, n-nonoxy, n-decoxy, n-undecoxy and n-dodecoxy.
  • C 5 - to C 6 ⁇ cycloalkoxy groups for R 1 are especially cyclopentoxy and cyclohexoxy.
  • R 3 is preferably C 1 -C 4 -alkoxycarbonyl, such as especially methoxycarbonyl and ethoxycarbonyl or in particular hydrogen.
  • Suitable C 5 - to Ca-cycloalkyl radicals for R 4 and R 5 are especially C 5 - to C ß- cycloalkyl such as cyclopentyl and cyclohexyl, but also cycloheptyl, cyclooctyl, methylcyclopentyl, dimethylcyclopentyl, methylcyclohexyl, ethylcyclohexyl and dimethylcyclohexyl .
  • Suitable C 7 - to C ⁇ 8 -aralkyl radicals for R 4 are, for example, naphthylmethyl, diphenylmethyl or methylbenzyl, but in particular C 7 - to cin-phenylalkyl such as 1-phenylethyl, 2-phenylethyl, 1-phenylpropyl, 2-phenylpropyl , 3-phenylpropyl, 2-phenylprop-2-yl, 4-phenylbutyl, 2,2-dimethyl-2-phenylethyl, 5-phenylamyl, 10-phenyldecyl, 12-phenyldodecyl or especially benzyl.
  • Suitable tolyl radicals are ortho-, meta and especially p-tolyl.
  • the degree of alkoxylation n in the polyoxyethylene and polyoxypropylene radicals for R 4 is preferably 1 to 10, in particular 2 to 7, very particularly preferably 3 to 5.
  • Halogen atoms are to be understood as fluorine, iodine, but especially bromine and especially chlorine. '
  • substituted phenyl radicals occur as radicals R 7 and R 9 , the preferred degree of substitution is 2 or in particular 1.
  • Monosubstituted phenyl radicals are ortho-, meta- or preferably para-substituted, doubly substituted phenyl radicals often have a 2,4- Substitution patterns and triply substituted phenyl radicals are often used
  • the structure I includes both the respective E with respect to the spatial position of the substituents on the CC double bond in the compounds I. - as well as the Z isomers. Mixtures of both isomers can of course also occur.
  • R 2 denotes cyano or C bis ⁇ to C 4 alkoxycarbonyl.
  • R 9 is phenyl which is substituted by one or two Cteil ⁇ to C 4 alkyl groups, C ⁇ ⁇ to C 4 Alkoxy groups, chlorine atoms, cyano groups, hydroxyl groups or C ⁇ ⁇ to C 4 ⁇ alkoxycarbonyl groups can be substituted, or a six-membered unsaturated or saturated heterocyclic ring with up to three nitrogen atoms, which additionally benzanelliert and by one or two C ⁇ ⁇ to C 4 -alkyl groups, C ⁇ ⁇ to C 4 ⁇ alkoxy groups, chlorine atoms, cyano groups, hydroxy groups or C ⁇ ⁇ to C 4 ⁇ alkoxycarbonyl groups can be substituted.
  • Pyridine, pyrimidine, pyridazine, pyrazine and 1,3,5-triazine are particularly suitable as heterocyclic rings for R 9 .
  • polyalkylpiperidine groups according to the invention containing the acetic acid and 3-aminoacrylic acid derivatives I can be prepared by methods known per se.
  • the reaction is conveniently carried out in a suitable polar organic solvent such as an alcohol, e.g. n-propanol, n-butanol, ethylene glycol, diethylene glycol, ethylene glycol monomethyl ether or cyclohexanol.
  • a suitable polar organic solvent such as an alcohol, e.g. n-propanol, n-butanol, ethylene glycol, diethylene glycol, ethylene glycol monomethyl ether or cyclohexanol.
  • Carboxylic acid amides such as dimethylformamide or excess trialkyl orthoformate are also suitable as solvents. If the starting compounds used already form a liquid mixture, an additional solvent can be dispensed with.
  • Lewis acids such as boric acid, AICI3, ZrCl 4 , TiCl4 or, above all, ZnCl 2 can also be used as catalysts for the reaction in the amounts customary for this.
  • the 3-aminoacrylic acid alkyl esters prepared in this way can be easily converted into the corresponding derivatives I containing polyalkylpiperidine groups.
  • This is advantageously done by transesterification with, for example, 2,2,6,6-tetramethyl-4-piperidinol in an inert organic solvent such as toluene or xylene in the presence of a catalyst such as tetrabutyl orthotitanate, phenothiazine, lithium amide or dibutyltin acetate.
  • polyalkylpiperidinyl-substituted a ides of the formula I is advantageously carried out by reacting the above-mentioned alkyl cyanoacetates, malonalkyl esters or alkyl acetoacetates with triacetone diamine and, if desired, subsequent reaction with aromatic or heterocyclic amines of the formula R 7 -NH 2 or R 7 - NHR 6 as described above.
  • radical R 1 in the compounds I denotes an acrylic acid ester group
  • compounds I in which R 1 is hydrogen are advantageously reacted with acetylenecarboxylic acid derivatives such as propiolic acid esters or acetylenedicarboxylic acid esters to prepare such compounds.
  • the compounds I according to the invention are outstandingly suitable for stabilizing organic material against the action of light, oxygen and heat. They are also effective as metal deactivators. They are added to the organic material to be stabilized in a concentration of 0.01 to 5% by weight, preferably 0.02 to 2% by weight, based on the organic material, before, during or after its production.
  • Organic material means, for example, cosmetic preparations such as ointments and lotions, pharmaceutical formulations such as pills and suppositories, photographic recording materials, in particular photographic emulsions, or precursors for plastics and lacquers, but especially plastics and lacquers themselves.
  • the present invention also relates to organic material, in particular plastics and lacquers, which is stabilized against the action of light, oxygen and heat and which contains the compounds I in the concentrations indicated above.
  • the organic material stabilized by the compounds I according to the invention may optionally contain further additives, e.g. B. antioxidants, light stabilizers, metal deactivators, antistatic agents, flame retardants, pigments and fillers.
  • further additives e.g. B. antioxidants, light stabilizers, metal deactivators, antistatic agents, flame retardants, pigments and fillers.
  • Antioxidants and light stabilizers which can be added in addition to the compounds I according to the invention are, for. B. Compounds based on sterically hindered phenols or sulfur or phosphorus containing CoStabili ⁇ sators.
  • phenolic antioxidants examples include 2,6-di-tert-butyl-4-methylph.enol, n-octa-decyl- ⁇ - (3,5-di-tert-butyl-4-hydroxyphenyl) - propionate, 1,1,3-tris (2-methyl-4-hydroxy-5-tert-butylphenyl) butane.
  • phosphorus-containing antioxidants examples include tris (nonylphenyl) phosphite, distearylpentaerythritol diphosphite, tris (2,4-di-tert-butyl-phenyl) phosphite, tris (2-tert-butyl-4-methylphenyl) -phosphite, bis- (2,4-di-tert-butylphenyl) pentaerythritol diphosphite and tetrahis (2,4-di-tert-butylphenyl) -4,4'-biphenylene diphosphite.
  • sulfur-containing antioxidants are dilauryl thiodipropionate, dimyristyl thiodipropionate, distearyl thiodipropionate, pentaerythritol tetris (ß-laurylthiopropionate) and pentaerythritol tetris (ß-hexylthiopropionate).
  • antioxidants and light stabilizers that can be used together with the compounds I according to the invention are, for. B. 2- (2 r -hydroxyphenyl) benzotriazoles,
  • 2-hydroxybenzophenones aryl esters of hydroxybenzoic acids, ⁇ -cyanocinnamic acid derivatives, benzimidazolecarboxylic acid anilides, nickel compounds or oxalic acid dianilides.
  • a particularly good stabilization is obtained if at least one further light stabilizer from the class of sterically hindered amines is added to the compounds I in the usual concentration.
  • Examples of further sterically hindered amines are: bis- (2,2,6,6-tetramethylpiperidyl) sebacate, bis- (1,2,2,6,6-pentamethylpiperidyl) sebacate, the condensation product of l-Hydroxyethyl-2,2, 6, 6-tetramethyl-4-hydroxypiperidine and succinic acid, the condensation product of N, N '- (2,2,6, 6-tetramethylpiperidyl) -hexamethylene diamine and 4-tert-octylamino -2, 6-dichloro-l, 3,5-triazine, tris (2,2, 6, 6-tetramethylpiperidyl) nitrilotriacetate, tetrakis (2,2,6, 6-tetramethyl-4-piperidyl) -1,2,3,4-butane-tetra- carboxylic acid, 1,1 '- (1,2-ethanediyl) -bis- (3,3,5,5-tetramethyl
  • plastics which can be stabilized by the compounds I according to the invention are:
  • Polymers of mono- and diolefins such as. B. low or high density polyethylene, polypropylene, linear poly-1-butene, polyisoprene, polybutadiene and copolymers of mono- or diolefins or mixtures of the above-mentioned polymers;
  • Copolymers of mono- or diolefins with other vinyl monomers such as.
  • Polystyrene and copolymers of styrene or ⁇ -methylstyrene with dienes and / or acrylic derivatives such as.
  • ABS acrylonitrile-butadiene-styrene
  • MBS methyl methacrylate-butadiene-styrene
  • Halogen-containing polymers such as. B. polyvinyl chloride, polyvinyl fluoride, polyvinylidene fluoride and their copolymers;
  • Polymers derived from ⁇ , ⁇ -unsaturated acids and their derivatives such as polyacrylates, polymethacrylates, polyacrylamides and polyacrylonitriles;
  • Polymers derived from unsaturated alcohols and amines or from their acrylic derivatives or acetals e.g. B. polyvinyl alcohol and polyvinyl acetate;
  • lacquer coatings can be stabilized with the compounds I according to the invention, for. B. Industrial paints. Among these, stove enamels, among them in turn vehicle paints, preferably two-coat paints, are particularly noteworthy.
  • the compounds I according to the invention can be added to the lacquer in solid or dissolved form. Their good solubility in coating systems is of particular advantage.
  • the compounds I according to the invention are preferably used to stabilize polyurethanes, polyesters, polystyrene, polyolefins such as ethylene or propylene polymers, polyamides, and ABS and SAN polymers, in particular molding compositions thereof, and of lacquer coatings, in particular from acid-curing lacquers .
  • Another preferred area of application is the stabilization of fibers made of polypropylene and polyamide.
  • the compounds I according to the invention are notable for good compatibility with the customary types of plastics and for good solubility and excellent compatibility in the conventional coating systems. As a rule, they have no or only a very slight intrinsic color, are stable at the usual plastics and lacquer processing temperatures and are non-volatile and, above all, bring about a long protection period for the materials treated with them.
  • the invention is further illustrated by the examples below.
  • the manufacturing conditions have not been optimized.
  • Example 1 Analogously to Example 1, using the corresponding aromatic or heterocyclic amines, the products listed in Table 1 were prepared from N- (2,2,6,6-tetramethyl-piperidin-4-yl) -cyanoacetic acid amide. The melting points and the spectroscopic data of the products are also given in Table 1.
  • Example 15a Analogously to Example 15a, the products listed in Table 2 were prepared from the compounds of Examples 2, 3, 5, 6, 7, 9, 10, 11, 12 and 13 and ethyl propiolate. The melting points and the spectroscopic data of the products are also given in Table 2.
  • Example 26 Analogously to Example 26, using the corresponding aromatic or heterocyclic amines, the products listed in Table 3 were prepared from 2,2,6,6-tetramethyl-4-piperidinyl esters of cyanoacetate. The melting points and the spectroscopic data of the products are also given in Table 3.
  • Example 15a Analogously to Example 15a, the products listed in Table 4 were prepared from the compounds of Examples 26, 27, 28, 29 and 30 and ethyl propiolate. The melting points and the spectroscopic data of the products are also given in Table 4.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Hydrogenated Pyridines (AREA)

Abstract

Dérivés de l'acide acétique et de l'acide amino-3-acrylique contenant les groupes polyalkylpipéridine, de formule (I) dans laquelle R1 désigne un hydrogène, un alkyle en C¿1? à C6, formyle, alcanoyle en C2 à C6, alcoxy en C1 à C12, cycloalcoxy en C5 à C6, cyanométhyle, 2-hydroxyéthyle, benzyle ou un reste de formule -CR?3¿=CH-CO-OR?4- où R3¿ est un hydrogène, un alkyle en C¿1? à C6 ou un reste de formule -CO-OR?4, et R4¿ est un alkyle en C¿1? à C20, cycloalkyle en C5 à C8, aralkyle en C7 à C18, phényle, tolyle ou un reste de formule -(CH2CH2O)nH ou -[CH(CH3)CH2O]nH, où n est un nombre compris entre 1 et 30; R?2¿ désigne un cyano, un reste de formule -CO-R5 ou -CO-OR5 ou un groupe de formule (II) où R5 désigne un alkyle en C¿1? à C12, un cycloalkyle en C5 à C8, benzyle, phényle ou tolyle, X désigne O, NH ou NR?6, où R6¿ désigne un alkyle en C¿1? à C12, et Y désigne un atome d'hydrogène ou un groupement de formule =CH-NHR?7¿ ou =CH-NR?6R7, où R7¿ désigne un phényle pouvant être substitué par un à trois groupes alkyle en C¿1? à C12, alcoxy en C1 à C12, atomes d'halogène, cyano, hydroxyle, phényle ou groupes de formule -CO-OR?5, -CO-R5¿, -CO-NHR5, -O-CO-R5 ou -NH-CO-R5, un hétérocycle insaturé ou saturé, à cinq ou six chaînons, ayant jusqu'à trois hétéroatomes du groupe azote, oxygène et soufre, pouvant être en outre benzo-anellé et substitué par un à trois groupes alkyle en C¿1? à C12, groupes alcoxy en C1 à C12, atomes d'halogène, groupes cyano, groupes hydroxyle, groupes phényle, groupes phénoxy ou groupes alcoxycarbonyle en C1 à C12, ou bien désigne, dans le cas où il existe une variable X pour NH ou NR?6¿, un groupe de formule (III).
EP93908853A 1992-04-07 1993-03-26 Derives de l'acide acetique et de l'acide amino-3-acrylique contenant des groupes polyalkylpiperidine Withdrawn EP0635005A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE4211603 1992-04-07
DE4211603A DE4211603A1 (de) 1992-04-07 1992-04-07 Polyalkylpiperidin-Gruppen enthaltende Essigsäure- und 3-Aminoacrylsäure-Derivate
PCT/EP1993/000739 WO1993020051A1 (fr) 1992-04-07 1993-03-26 Derives de l'acide acetique et de l'acide amino-3-acrylique contenant des groupes polyalkylpiperidine

Publications (1)

Publication Number Publication Date
EP0635005A1 true EP0635005A1 (fr) 1995-01-25

Family

ID=6456263

Family Applications (1)

Application Number Title Priority Date Filing Date
EP93908853A Withdrawn EP0635005A1 (fr) 1992-04-07 1993-03-26 Derives de l'acide acetique et de l'acide amino-3-acrylique contenant des groupes polyalkylpiperidine

Country Status (6)

Country Link
US (1) US5624981A (fr)
EP (1) EP0635005A1 (fr)
JP (1) JPH07505374A (fr)
DE (1) DE4211603A1 (fr)
TW (1) TW230779B (fr)
WO (1) WO1993020051A1 (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4211603A1 (de) * 1992-04-07 1993-10-14 Basf Ag Polyalkylpiperidin-Gruppen enthaltende Essigsäure- und 3-Aminoacrylsäure-Derivate
DE19544404A1 (de) * 1995-11-29 1997-06-05 Basf Ag Tetramethylpiperidinhaltige Copolymere
IT1278535B1 (it) 1995-12-14 1997-11-24 3V Sigma Spa Derivati di benzofurano e loro uso come fotostabilizzanti e filtri solari
JP4334033B2 (ja) * 1998-03-23 2009-09-16 アキレス株式会社 農業用塩化ビニル系樹脂フィルム
KR20100068083A (ko) * 2008-12-12 2010-06-22 제일모직주식회사 (메트)아크릴레이트 화합물, 감광성 폴리머, 및 레지스트 조성물

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL279734A (fr) * 1961-06-26
CH601232A5 (fr) * 1975-12-08 1978-06-30 Ciba Geigy Ag
DE2755340A1 (de) * 1976-12-23 1978-06-29 Ciba Geigy Ag Neue polyalkylpiperidinderivate
DE2849444A1 (de) * 1978-11-15 1980-05-29 Hoechst Ag Beta aminocrotonsaeurepiperidylester, verfahren zu ihrer herstellung und ihre verwendung als lichtschutzmittel
US4444928A (en) * 1981-08-14 1984-04-24 Ciba-Geigy Corporation Polymeric malonic acid derivatives
JPS5962651A (ja) * 1982-10-02 1984-04-10 Adeka Argus Chem Co Ltd 高分子材料用光安定剤
IT1203354B (it) * 1987-02-26 1989-02-15 Ciba Geigy Spa Composti piperidinici atti all'impiego come stabilizzanti per polimeri e copolimeri sintetici
EP0410970B1 (fr) * 1989-02-13 1996-08-14 Elf Atochem North America, Inc. Photostabilisants reactifs a amine inhibee
DE4211603A1 (de) * 1992-04-07 1993-10-14 Basf Ag Polyalkylpiperidin-Gruppen enthaltende Essigsäure- und 3-Aminoacrylsäure-Derivate

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9320051A1 *

Also Published As

Publication number Publication date
TW230779B (fr) 1994-09-21
JPH07505374A (ja) 1995-06-15
US5624981A (en) 1997-04-29
DE4211603A1 (de) 1993-10-14
WO1993020051A1 (fr) 1993-10-14

Similar Documents

Publication Publication Date Title
EP0316582B1 (fr) Dérivés de 4-formylaminopipéridine, leur utilisation comme stabilisateurs et les matériaux organiques ainsi stabilisés
DE3530666A1 (de) Glykolurilderivate und ihre verwendung als stabilisatoren fuer polymere
EP0212115B1 (fr) Dérivés d'aminoalkyl-3-t-butyl-4-hydroxyphénylpropionamide et du matériau organique stabilisé par ceux-ci
EP0325974B1 (fr) Hétérocycles à base de pipérazinopipérazine et leur utilisation
EP0635005A1 (fr) Derives de l'acide acetique et de l'acide amino-3-acrylique contenant des groupes polyalkylpiperidine
EP0349862B1 (fr) 2,6 polyalkyl pipéridine-4-amides, leur application comme stabilisateurs, en particulier pour matériaux synthétiques aussi bien que le matériau organique les contenant
EP0683785B1 (fr) Utilisation d'esters d'acide phosphonique aminovinylique comme agents photoprotecteurs et stabilisants pour matieres organiques
EP0593541B1 (fr) Esters et amides de l'acide aminomethylenecyanacetique
DE3643890A1 (de) Neue polyalkylpiperidinderivate mit alkylenbruecken, ihre verwendung als stabilisator und zwischenprodukte
EP0272590B1 (fr) Dérivés de glycolurile et leur utilisation comme stabilisants pour polymères
WO1993011111A1 (fr) DERIVES D'ESTERS DE L'ACIDE β-AMINOACRYLIQUE CONTENANT DES GROUPES POLYALKYLPIPERIDINE
DE4440055A1 (de) 2-Cyanacrylsäureester, Verfahren zu ihrer Herstellung und ihre Verwendung als Lichtschutzmittel und Stabilisatoren für organische Materialien
EP0682668B1 (fr) Derives de glycolurile contenant des groupes n-vinyl et leur utilisation comme agents photoprotecteurs et comme stabilisants pour des materiaux organiques
DE4403085A1 (de) Verfahren zur Herstellung von N,N'-verbrückten Bis-tetramethylpiperidinyl-Verbindungen
EP0481300A2 (fr) Polyalkyl-pipéridines et leur application comme stabilisateurs contre la lumière
EP0422492A1 (fr) Amides cycliques
DE4140304A1 (de) N-((beta)-carbonyl- und (beta)-cyanovinyl)-2,2,6,6- tetramethylpiperidin-derivate
WO1993009173A1 (fr) Utilisation d'esters 3-amino-2-(benzoylamino)acryliques comme stabilisants pour des matieres organiques
EP0272591A2 (fr) Dérivés d'acétylenediurée et leur application pour stabiliser les matières plastiques
EP0324945A2 (fr) Dérivés hétérocycliques de bicyclo [3.3.1] nonane et leur application
EP0503338A1 (fr) Hétérocycles aminovinyl-substitués comme stabiliseurs pour des matières organiques
EP0505802A1 (fr) Esters polyalkylpipéridinyliques des acides bêta-cétocarboxyliques cycliques
EP0355663A2 (fr) Bislactames substituées par 2,6-polyalkylpipéridinyle et leur utilisation pour la stabilisation de matériaux organique, en particulier, plastiques et matériaux stabilisés
CH669195A5 (de) Furan-3-carbonsaeurederivate und deren verwendung als lichtschutzmittel ausserhalb der textilindustrie.
EP0373437A2 (fr) Lactames substitués par des polyalcoylpipéridines et leur utilisation comme stabilisants pour polymères

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 19940903

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AT BE CH DE DK ES FR GB IE IT LI NL PT SE

17Q First examination report despatched

Effective date: 19971202

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION HAS BEEN WITHDRAWN

18W Application withdrawn

Withdrawal date: 19980225