EP0790980A1 - 2-cyanacrylsäureester - Google Patents

2-cyanacrylsäureester

Info

Publication number
EP0790980A1
EP0790980A1 EP95938395A EP95938395A EP0790980A1 EP 0790980 A1 EP0790980 A1 EP 0790980A1 EP 95938395 A EP95938395 A EP 95938395A EP 95938395 A EP95938395 A EP 95938395A EP 0790980 A1 EP0790980 A1 EP 0790980A1
Authority
EP
European Patent Office
Prior art keywords
cyanoacrylic acid
acid esters
hydrogen
acid ester
esters according
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Withdrawn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
EP95938395A
Other languages
German (de)
English (en)
French (fr)
Inventor
Martin Holderbaum
Alexander Aumüller
Hubert Trauth
Guido Voit
Karin Sperling
Alfred Krause
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
Priority claimed from DE4440055A external-priority patent/DE4440055A1/de
Priority claimed from DE19519895A external-priority patent/DE19519895A1/de
Application filed by BASF SE filed Critical BASF SE
Priority to EP98120701A priority Critical patent/EP0900782B1/de
Publication of EP0790980A1 publication Critical patent/EP0790980A1/de
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/23—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and carboxyl groups, other than cyano groups, bound to the same unsaturated acyclic carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
    • C07C255/41—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by carboxyl groups, other than cyano groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B63/00—Purification; Separation; Stabilisation; Use of additives
    • C07B63/04—Use of additives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/19—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and carboxyl groups, other than cyano groups, bound to the same saturated acyclic carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/30—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the same unsaturated acyclic carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
    • C07C255/42—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by singly-bound nitrogen atoms, not being further bound to other hetero atoms
    • 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
    • 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
    • C08K5/315—Compounds containing carbon-to-nitrogen triple bonds
    • 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
    • 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
    • C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
    • C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
    • C09K15/16—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing nitrogen

Definitions

  • the present invention relates to new 2-cyanoacrylic acid esters of the formula I,
  • radicals R 1 and R 2 are hydrogen or a radical having an iso- or heterocyclic ring system with at least one iso- or heteroaromatic nucleus, where at least one of the radicals R 1 or R 2 must be different from hydrogen,
  • n has a value from 2 to 10 and
  • X in the event that n> 2, denotes the radical of an n-valent aliphatic or cycloaliphatic polyol having 3 to 20 carbon atoms, it being possible for a cycloaliphatic radical to also contain 1 to 2 heteroatoms and one aliphatic The rest can be interrupted by up to 8 non-adjacent oxygen atoms, sulfur atoms, imino or C ⁇ -C alkylimino groups.
  • the invention further relates to a process for the preparation of the compounds I, their use as light stabilizers or stabilizers for organic materials, in particular for cosmetic or dermatological preparations, plastics or lacquers, and also organic materials which contain the compounds I.
  • US Pat. No. 3,215,725 and DE-A 41 22 475 disclose 2-cyanoacrylic acid esters of monohydric and dihydric alcohols as light stabilizers for plastics and paints.
  • the 2-cyanoacrylic acid ester groups of I can be in either the ice or the trans form. Mixtures of these isomers are usually formed in the preparation of the compounds. Separation of these isomers is possible, but is not necessary for most applications.
  • Suitable organic radicals for R 1 and R 2 are generally ring structures which contain at least one iso- or hetero-aromatic nucleus which is preferably bonded directly to the 3-C atom of the acrylic acid group, but also via ali- phatic or cycloaliphatic groups as well as a bridge member -NR 3 - can be linked to this carbon atom.
  • R 1 or R 2 is preferably a radical of the formula III
  • R 3 is hydrogen or -CC-alkyl
  • r represents the number 0 or 1
  • R 4 to R 8 independently of one another are hydrogen, Ci-Cg-alkyl, chlorine, bromine, cyano, nitro, amino,
  • C 3 -C 6 -alkyl radicals are suitable as R 3 , such as methyl, ethyl, n-propyl, iso-propyl, iso-propyl, n-propyl, n-butyl, iso-butyl-sec-butyl, tert-butyl, n-pentyl, iso-pentyl, sec.-pentyl, tert.-pentyl, neo-pentyl, n-hexyl, n-heptyl, n-octyl, iso-octyl, 2-ethylhexyl, n-nonyl , iso-nonyl, n-decyl and iso-decyl.
  • the alkyl radicals contained therein can be, for example, methyl, ethyl, n- Propyl, iso-propyl, n-propyl, n-butyl, iso-butyl, sec.-butyl, tert.-butyl, n-pentyl, iso-pentyl, sec.-pentyl, tert.-pentyl, neo-pentyl, be n-hexyl, n-heptyl, n-octyl or 2-ethylhexyl.
  • Ci-Cie-alkoxy or C ⁇ -C ⁇ 2 alkoxy carbonyl groups come, for example, nonyl, 2-methylnonyl, isononyl, 2-methyloctyl, decyl, isodecyl, 2-methylnonyl, undecyl, isoundecyl, dodecyl, isododecyl , Tridecyl, isotridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl and octadecyl.
  • Suitable C 3 - to C ⁇ -cycloalkyl radicals are, for example, cyclopropyl, cyclobutyl, cyclopentyl, methylcyclopentyl or cyclohexyl. These cycloalkyl groups are also suitable radicals in C 3 - to C ⁇ -cycloalkylcarbonyl groups.
  • Preferred 2-cyanoacrylic acid esters I are those in which R 3 is hydrogen, methyl or ethyl.
  • 2-cyanoacrylic esters I are preferred in which up to three, particularly preferably one of the radicals R 4 to R 8 are hydrogen ⁇ material, C ⁇ -C 4 alkyl, chlorine, cyano, hydroxy, acetyl, C ⁇ -05-alkoxy, Ci-C ⁇ -alkoxycarbonyl or cyclohexoxycarbonyl and the rest of these radicals are hydrogen.
  • Those 2-cyanoacrylic acid esters I in which R 6 denotes a hydroxyl, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy or tert-butoxy group are particularly preferred, since such groups 4-substituted phenyl groups contribute to the stabilizing effect of the compounds.
  • 2-cyanoacrylic esters in which R 5 and / or R 7 are hydrogen, a methyl or tert-butyl group are particularly preferred, in particular when R 6 is a hydroxyl group.
  • R 1 or R 2 is hydrogen
  • R 1 and R 2 are identical radicals
  • one of the radicals R 1 or R 2 is phenylamino, p-tolylamino, p-methoxy- or p-ethoxycarbonylphenylamino and the other is hydrogen.
  • R 1 or R 2 Another preferred radical for R 1 or R 2 is the chroman radical Ib
  • R 1 and R 2 are heterocyclic groups such as substituted or unsubstituted thiophenyl, furfuryl and pyridyl radicals.
  • m is a value from 2 to 8, preferably 2 to 6, but particularly preferably 2.
  • X stands for the remainder of an n-valent aliphatic or cycloaliphatic alcohol. These alcohols can be linear or branched, and their C chains can be interrupted by one or more oxygen or sulfur atoms, by imino groups (-NH-) or Ci-Ci-alkylimino groups.
  • the grouping X is preferably derived from the following known polyols:
  • the 2-cyanoacrylic acid esters of the formula I in which R 1 and R 2 are not bonded to the ⁇ -C atom via a nitrogen atom are preferably by reaction of cyanoacetic acid esters of the general formula III
  • the reaction can be carried out, for example, in aromatic solvents such as toluene or xylene (see, for example, Organikum, edition 1976, p. 572).
  • aromatic solvents such as toluene or xylene
  • polar organic solvents such as dimethylformamide, dimethylacetamide, N-methylpyrrolidone, tri-alkyl orthoformate or alcohols such as n-propanol, n-butanol, ethylene glycol, diethylene glycol, ethylene glycol monomethyl ether, cyclohexanol or similar compounds are preferably used. If the starting compounds used already form a liquid mixture, an additional solvent can be dispensed with.
  • the reaction temperatures are preferably between 20 and 180 ° C, particularly preferably between 40 and 150 ° C.
  • the pressure is preferably normal atmospheric pressure.
  • suitable catalysts are ammonium acetate, piperidine and ⁇ -alanine and their acetates.
  • Lewis acids such as A1C1 3 , ZrCl 4 , TiCl or, above all, ZnCl 2 can also be used as catalysts for the reaction in the amounts customary for this.
  • the 2-cyanoacrylic esters of the formula I in which r is 1, ie in which a radical R 1 or R 2 is bonded to the ⁇ -C atom via a nitrogen atom, can advantageously be prepared by using a cyanoacetic acid ester of the general formula IV
  • trialkyl orthoformate e.g. Trimethyl orthoformate and triethyl orthoformate have proven themselves.
  • the cyanoacetic esters II can be prepared, for example, by reacting cyanoacetic acid or its esters with the corresponding polyols X (OH) n in the presence of a catalyst such as boric acid, Na 2 CO 3 or K CO 3 or tetrabutyl orthotitanate, preferably in toluene or xylene.
  • a catalyst such as boric acid, Na 2 CO 3 or K CO 3 or tetrabutyl orthotitanate, preferably in toluene or xylene.
  • the compounds according to the invention are outstandingly suitable for stabilizing organic materials against the action of light, oxygen and heat.
  • plastics which can be stabilized by the compounds I according to the invention are:
  • Polymers of mono- and diolefins such as low or high density polyethylene, polypropylene, linear polybutene-1, polyisoprene, polybutadiene and copolymers of mono- or diolefins or mixtures of the polymers mentioned; Copolymers of mono- or diolefins with other vinyl monomers, such as, for example, ethylene-alkyl acrylate copolymers, ethylene-alkyl methacrylate copolymers, ethylene-vinyl acetate copolymers or ethylene-acrylic acid copolymers;
  • Polystyrene and copolymers of styrene or ⁇ -methylstyrene with dienes and / or acrylic derivatives such as e.g. Styrene-butadiene, styrene-acrylonitrile (SAN), styrene-ethyl methacrylate, styrene-butadiene-ethyl acrylate, styrene-acrylonitrile-methacrylate, acrylonitrile-butadiene-styrene (ABS) or methyl methacrylate-butadiene-styrene (MBS);
  • SAN styrene-acrylonitrile
  • ABS acrylonitrile-butadiene-styrene
  • MVS methyl methacrylate-butadiene-styrene
  • Halogen-containing polymers e.g. 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. Polyvinyl alcohol and polyvinyl acetate;
  • Polyurethanes polyamides, polyureas, polyphenylene ethers, polyesters, polycarbonates, polyoxymethylenes, polysulfones, polyether sulfones and polyether ketones.
  • Coatings can also be stabilized with the compounds I according to the invention, e.g. Industrial paints.
  • Industrial paints e.g., stove enamels, among them 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 for stabilizing polyolefins, in particular polyethylene, polycarbonates, polyamides, polyesters, polystyrene, ABS and polyurethanes.
  • polyolefins in particular polyethylene, polycarbonates, polyamides, polyesters, polystyrene, ABS and polyurethanes.
  • films made from the plastics mentioned can also be stabilized.
  • the compounds are used in concentrations of 0.01 to 5% by weight, based on the amount of the plastic, preferably in a concentration of 0.02 to 2% by weight.
  • stabilizers for example antioxidants, metal deactivators or other light Protective agents and with antistatic or flame-retardant agents are often advantageous.
  • Particularly important costabilizers are, for example, sterically hindered phenols and phosphites, phosphonites, amines and sulfur compounds.
  • Suitable costabilizers are e.g. considered:
  • Pentaerythritol tetrakis [ß- (3,5-di-tert-butyl-4-hydroxy) propionate]
  • sulfur-containing antioxidants such as dilauryl thiodipropionate
  • Pentaerythritol tetrakis (ß-laurylthiopropionate)
  • Oxalic acid dianilides
  • the 2-cyanoacrylic acid esters 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 customary 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 bring about a long protection period for the materials treated with them. Above all, however, they show practically no tendency to migrate in plastics.
  • the UV radiation is divided into three areas: the UV-A area (320-400 nm), the UV-B area (290-320 nm) and the UV-C area (200-290 nm) .
  • the high-energy UV-C range is mainly absorbed by the ozone layer. Radiation in the UV-B range is primarily responsible for the development of sunburn and skin cancer. When exposed to UV-A for a long time, it tans the skin, but is also responsible for the aging of the skin.
  • the compounds according to the invention are particularly suitable for applications in the cosmetic and dermatological range.
  • the compounds can also be used advantageously to protect cosmetic preparations such as perfumes, creams and lotions.
  • Particularly preferred are combinations with light stabilizers that absorb in the UV-B range.
  • the 2-cyanoacrylic acid esters I are used in concentrations of 0.05 to 15% by weight, preferably 0.1 to 10% by weight, based on the total amount of the cosmetic formulation.
  • organic materials to which the compounds according to the invention are advantageously admixed are pharmaceutical formulations such as pills and suppositories, photographic recording materials, in particular photographic emulsions, and preliminary products for plastics and paints.
  • Example 2 was prepared in analogy to Example 1 from the corresponding cyanate 40 and benzophenone imine; Melting point: 92 ° C; UV (CH 2 C1 2 ) t ⁇ max - 308 nm, ⁇ - 36700.
  • Example 40 was prepared in analogy to Example 1 from the corresponding cyanoacetic acid ester and benzophenone imine; Melting point: 124 to 128 ° C; UV (CH 2 C1 2 ) ⁇ ax - 308 nm, ⁇ * 76000.
  • UV stabilizer specified below 0.3% by weight of the UV stabilizer specified below was dissolved in polyethylene by extrusion twice in the polymer at a mass temperature of 180 ° C., after which the polymer was granulated and blown to give 100 ⁇ m thick films.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Hydrogenated Pyridines (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Materials For Medical Uses (AREA)
EP95938395A 1994-11-10 1995-11-03 2-cyanacrylsäureester Withdrawn EP0790980A1 (de)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP98120701A EP0900782B1 (de) 1994-11-10 1995-11-03 2-Cyanacrylsäureester

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
DE4440055A DE4440055A1 (de) 1994-11-10 1994-11-10 2-Cyanacrylsäureester, Verfahren zu ihrer Herstellung und ihre Verwendung als Lichtschutzmittel und Stabilisatoren für organische Materialien
DE4440055 1994-11-10
DE19519895A DE19519895A1 (de) 1995-05-31 1995-05-31 2-Cyanacrylsäureester
DE19519895 1995-05-31
PCT/EP1995/004312 WO1996015102A2 (de) 1994-11-10 1995-11-03 2-cyanacrylsäureester

Related Child Applications (1)

Application Number Title Priority Date Filing Date
EP98120701A Division EP0900782B1 (de) 1994-11-10 1995-11-03 2-Cyanacrylsäureester

Publications (1)

Publication Number Publication Date
EP0790980A1 true EP0790980A1 (de) 1997-08-27

Family

ID=25941845

Family Applications (2)

Application Number Title Priority Date Filing Date
EP95938395A Withdrawn EP0790980A1 (de) 1994-11-10 1995-11-03 2-cyanacrylsäureester
EP98120701A Expired - Lifetime EP0900782B1 (de) 1994-11-10 1995-11-03 2-Cyanacrylsäureester

Family Applications After (1)

Application Number Title Priority Date Filing Date
EP98120701A Expired - Lifetime EP0900782B1 (de) 1994-11-10 1995-11-03 2-Cyanacrylsäureester

Country Status (19)

Country Link
US (1) US5821380A (zh)
EP (2) EP0790980A1 (zh)
JP (1) JP3889041B2 (zh)
KR (1) KR970707080A (zh)
CN (1) CN1046707C (zh)
AU (1) AU3980395A (zh)
BG (1) BG101460A (zh)
BR (1) BR9509644A (zh)
CA (1) CA2204430A1 (zh)
CZ (1) CZ134997A3 (zh)
DE (1) DE59510031D1 (zh)
ES (1) ES2172075T3 (zh)
FI (1) FI971991A0 (zh)
MX (1) MX9703351A (zh)
NO (1) NO972156L (zh)
PL (1) PL320203A1 (zh)
PT (1) PT0900782E (zh)
SK (1) SK56097A3 (zh)
WO (1) WO1996015102A2 (zh)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013068596A1 (de) 2011-11-12 2013-05-16 Anke Domaske Verfahren zur herstellung von milchprotein-fasern

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CN1162955A (zh) 1997-10-22
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DE59510031D1 (de) 2002-03-14
WO1996015102A2 (de) 1996-05-23
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CA2204430A1 (en) 1996-05-23
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