EP1678220A1 - Cires de copolymere d'ethylene contenant des groupes amino et leur utilisation - Google Patents

Cires de copolymere d'ethylene contenant des groupes amino et leur utilisation

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Publication number
EP1678220A1
EP1678220A1 EP04787001A EP04787001A EP1678220A1 EP 1678220 A1 EP1678220 A1 EP 1678220A1 EP 04787001 A EP04787001 A EP 04787001A EP 04787001 A EP04787001 A EP 04787001A EP 1678220 A1 EP1678220 A1 EP 1678220A1
Authority
EP
European Patent Office
Prior art keywords
ethylene copolymer
copolymer waxes
comonomer
waxes according
ionic
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Withdrawn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
EP04787001A
Other languages
German (de)
English (en)
Inventor
Andreas FECHTENKÖTTER
Meik Ranft
Bernhard Hauer
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 EP1678220A1 publication Critical patent/EP1678220A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • 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
    • C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
    • C08F210/02—Ethene

Definitions

  • the present invention relates to ethylene copolymer waxes with a molecular weight M w in the range from 1000 to 20,000 g / mol, which contain copolymerized comonomers
  • polymers which are essentially composed of structural units which are derived from trialkylamonium alkyl esters of acrylic acid or methacrylic acid and in which two of the three alkyl groups are composed of C 8 -C 12 alkyl and C 8 -C 2 -Alkenyl are selected, are suitable as a biocidal coating for example textile.
  • nonwovens can be finished with antimicrobial polymers.
  • antimicrobial polymers polymers of for example, dimethylaminopropyl methacrylamide or tert-butylaminomethacrylate or 3-aminopropyl vinyl ether.
  • polyethylene waxes of ethylene and dimethylaminoethyl acrylate with a molecular weight M w of 25,000 and 45,000 g / mol are known.
  • the polyethylene waxes disclosed in DE 42 34324 can be used as dispersants for polymeric molding compositions.
  • the object was to provide new substances which are suitable for controlling microorganisms and avoid the disadvantages of the microbicidal compositions known from the prior art. Furthermore, the task was to provide a process for the production of new microbicidal substances.
  • microorganisms or microorganism includes, for example, bacteria and also yeasts such as e.g. Candida albicans and mushrooms such as Aspergillus niger continues to understand algae.
  • Ethylene copolymer waxes according to the invention have a molecular weight M w in the range from 1000 to 20,000 g / mol, preferably 2000 to 15,000 g / mol.
  • Ethylene copolymer waxes according to the invention contain as copolymerized copolymerized comonomers:
  • Data in% by weight are based in each case on the total mass of ethylene copolymer wax according to the invention.
  • the alkylated or cycloalkylated amino group of comonomer (b) or comonomers (b) can be alkylated or cycloalkylated once or more than once. If it is desired to polymerize in several comonomers (b), the different comonomers (b) can have the same or different spacers or have the same or different polymerizable groups or can carry the same or different alkyl groups or cycloalkyl groups on the amino group or groups. It is also in the frame of the present invention it is conceivable that at least one comonomer (b) has two or more alkylated or cycloalkylated amino groups which are each connected via a spacer to a polymerizable group.
  • At least one comonomer (b) corresponds to the general formula I.
  • R 1 and R 2 are the same or different
  • R 1 is selected from hydrogen and
  • unbranched and branched CrC-io-alkyl such as, for example, methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec.-butyl, tert.-butyl, n-pentyl, iso-pentyl, sec .- Pentyl, neo-pentyl, 1,2-dimethylpropyl, iso-amyl, n-hexyl, iso-hexyl, sec.-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, n-decyl ; particularly preferably dC 4 -alkyl such as methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl and tert
  • R 2 is selected from unbranched and branched d-C ⁇ o-alkyl such as methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, iso -Pentyl, sec.-pentyl, neo-pentyl, 1, 2-dimethylpropyl, iso-amyl, n-hexyl, iso-hexyl, sec.-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl , n-decyl; particularly preferably CC 4 alkyl such as methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl and tert-buty
  • R 3 are different or preferably identical and selected from hydrogen and branched and preferably unbranched CC 10 alkyl, for example methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec.-butyl, tert.- Butyl, n-pentyl, isopentyl, sec.-pentyl, neo-pentyl, 1, 2-dimethylpropyl, iso-amyl, n-hexyl, iso-hexyl, sec.-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, n-decyl; preferably methyl, ethyl, n-propyl, n-butyl, n-pentyl, isopentyl, n-hexyl, n-heptyl,
  • C 3 -C 2 cycloalkyl such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, cycloundecyl and cyclododecyl; cyclopentyl, cyclohexyl and cycloheptyl are preferred
  • R 3 radicals can be connected to one another to form a 3- to 10-membered, preferably 5- to 7-membered ring which is optionally substituted by CC 4 -alkyl radicals,
  • radicals R 3 are different, one of the radicals R 3 can be hydrogen.
  • X is selected from sulfur, NR 4 and especially oxygen.
  • R 4 is selected from hydrogen and unbranched and branched CrC 10 alkyl, such as methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, iso-pentyl, sec.-pentyl, neo-pentyl, 1, 2-dimethylpropyl, iso-amyl, n-hexyl, iso-hexyl, sec.-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n- Nonyl, n-decyl; particularly preferably C 1 -C 4 -alkyl such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl and tert-butyl
  • a 1 is chosen from divalent groups such as
  • Crdo-alkylene such as -CH 2 -, -CH (CH 3 ) -, - (CH 2 ) 2 -, -CH 2 -CH (CH 3 ) -, ice and trans-CH (CH 3 ) -CH (CH 3 ) -, - (CH 2 ) 3 -, -CH 2 -CH (C 2 H 5 ) -, - (CH 2 ) 4 -, - (CH 2 ) 5 -, - (CH 2 ) 6 - , - (CH 2 ) 7 -, - (CH 2 ) 8 -, - (CH 2 ) 9-, - (CH 2 ) ⁇ o-; preferably C 2 -C 4 alkylene; such as - (CH 2 ) 2 -, -CH 2 - CH (CH 3 ) -, - (CH 2 ) 3 -, - (CH 2 ) - and -CH 2 -CH (C 2 H 5
  • Phenylene for example ortho-phenylene, meta-phenylene and particularly preferably para-phenylene.
  • R represents hydrogen or methyl.
  • R 1 very particularly preferably denotes methyl.
  • R 1 is hydrogen or methyl and R 2 is hydrogen.
  • R 1 is hydrogen or methyl and R 2 is hydrogen, both radicals R 3 are the same and each represents methyl or ethyl.
  • XA 1 -N (R 3 ) 2 represents O-CH 2 -CH 2 -N (CH 3 ) 2 .
  • ethylene copolymer waxes according to the invention contain no further comonomers copolymerized. In one embodiment of the present invention, ethylene copolymer waxes according to the invention contain at least one further comonomer (c) in copolymerized form.
  • Preferred further copolymerized comonomers (c) are, for example, isobutene and (meth) acrylic acid esters, in particular (meth) acrylic acid alkyl esters, for example (methacrylic acid-CrC ⁇ alkyl esters.
  • ethylene copolymer waxes according to the invention have a melt flow rate (MFR) in the range from 1 to 500 g / 10 min, preferably 5 to 200 g / 10 min, particularly preferably 7 to 50 g / 10 min, measured at 160 ° C. and a load of 325 g according to DIN 53735.
  • MFR melt flow rate
  • ethylene copolymer waxes according to the invention have a kinematic melt viscosity v in the range from 500 to 10,000 mm 2 / s, preferably in the range from 800 to 4000 mm 2 / s, measured in accordance with DIN 51562.
  • the melting ranges of ethylene copolymer wax according to the invention can be wide and relate to a temperature interval of at least 5 to at most 20 ° C., preferably at least 7 ° C. to at most 15 ° C.
  • the melting points of ethylene copolymer wax according to the invention are sharp and lie in a temperature interval of less than 2 ° C., preferably less than 1 ° C., determined according to DIN 51007.
  • the density of the ethylene copolymer waxes according to the invention is 0.89 to 1.10 g / cm 3 , preferably 0.92 to 0.94 g / cm 3 , determined in accordance with DIN 534-79.
  • Ethylene copolymer waxes according to the invention can be alternating copolymers or block copolymers or preferably statistical copolymers.
  • Ethylene copolymer waxes according to the invention can advantageously be prepared by free-radically initiated copolymerization of ethylene with at least one comonomer which has at least one alkylated or cycloalkylated amino group, each of which is connected to a polymerizable group via a spacer, and, if appropriate, one or more further comonomers under high pressure conditions, below also called the polymerization process according to the invention.
  • the polymerization process according to the invention can be carried out, for example, in stirred high-pressure autoclaves or in high-pressure tube reactors or in combinations of or in combinations of high-pressure autoclave and high-pressure tube reactor which are connected in series.
  • the implementation in stirred high pressure autoclaves is preferred.
  • Stirred high-pressure autoclaves are known per se, a description can be found in Ullmann's Encyclopedia of Industrial Chemistry, 5th edition, keywords: Waxes, Vol. A 28, p. 146 ff., Verlag Chemie Weinheim, Basel, Cambridge, New York, Tokyo, 1996.
  • the ratio length / diameter is predominantly in intervals of 5: 1 to 30: 1, preferably 10: 1 to 20: 1.
  • Suitable pressure conditions for the polymerization process according to the invention are 500 to 4000 bar, preferably 1500 to 2500 bar. Conditions of this type are also referred to below as high pressure.
  • the reaction temperatures are in the range from 170 to 300 ° C., preferably in the range from 195 to 280 ° C.
  • the copolymeosation can be carried out in the presence of at least one regulator.
  • the regulator used is, for example, hydrogen or at least one aliphatic aldehyde or at least one aliphatic ketone of the general formula III
  • radicals R 5 and R 6 are the same or different and selected from
  • d-Ce-alkyl such as methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, iso-pentyl, sec-pentyl, neo-pentyl, 1, 2-dimethylpropyl, iso- Amyl, n-hexyl, iso-hexyl, sec.-hexyl, particularly preferably CrC 4 alkyl such as methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec.-butyl and tert.- butyl;
  • C 3 -C 12 cycloalkyl such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, cycloundecyl and cyclododecyl; cyclopentyl, cyclohexyl and cycloheptyl are preferred.
  • R 5 and R 6 are covalently bonded to one another to form a 4- to 13-membered ring.
  • R 6 and R 5 can be common: - (CH 2 ) -, - (CH 2 ) 5 -, - (CH 2 ) 6 , - (CH 2 ) 7-, -CH (CH 3 ) - CH 2 -CH 2 -CH (CH 3 ) - or -CH (CH 3 ) -CH 2 -CH2-CH 2 -CH (CH 3 ) -.
  • radical initiators such as organic peroxides, oxygen or azo compounds can be used as starters for radical polymerization. Mixtures of several radical initiators are also suitable.
  • C 6 -C 14 aryl such as phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl and 9-phenanthryl, preferably phenyl, 1-naphthyl and 2-naphthyl, particularly preferably phenyl.
  • Peroxides of the general formulas III a to III c and processes for their preparation are known from EP-A 0 813 550.
  • Di-tert-butyl peroxide, tert-butyl peroxypivalate, tert-butyl peroxyisononanoate or dibenzoyl peroxide or mixtures thereof are particularly suitable as peroxides.
  • Azobisisobutyronitrile (“AIBN”) may be mentioned as an example as an azo compound.
  • Free radical initiators are metered in amounts customary for polymerizations.
  • the quantitative ratio of comonomers in the dosage usually does not exactly correspond to the ratio of the units in the ethyl Lencopolymer wax because comonomer, which has at least one alkylated or cycloalkylated amino group, each of which is connected via a spacer to a polymerizable group, is generally more easily incorporated into ethylene copolymer waxes than ethylene.
  • the proportion of comonomer which has at least one alkylated or cycloalkylated amino group which is in each case connected to a polymerizable group via a spacer is below 30% by weight of the total feed of comonomer, preferably below 20% by weight .-%.
  • the comonomer (s) and ethylene are usually metered in together or separately.
  • the comonomers can be compressed to the polymerization pressure in a compressor.
  • the comonomers are first brought to an increased pressure of, for example, 150 to 400 bar, preferably 200 to 300 bar and in particular 260 bar with the aid of a pump and then to the actual polymerization pressure using a compressor.
  • the polymerization process according to the invention can optionally be carried out in the absence and in the presence of solvents, mineral oils, white oil and other solvents which are present in the reactor during the polymerization and which have been used for the desensitization of the radical initiator, in the sense of the present invention, not as Solvents apply.
  • solvents are, for example, toluene, isododecane, isomers of xylene.
  • Y is selected from OH and 0-R 13 and
  • copolymerization of ethylene with at least one comonomer with a functional group can be carried out by methods familiar to the person skilled in the art.
  • the polymer-analogous reaction can be carried out, for example, in a solvent.
  • the present invention further provides ionic ethylene copolymer waxes which can be obtained by reacting ethylene copolymer waxes according to the invention with Bransted acid.
  • the present invention further provides a process for the preparation of ionic ethylene copolymer waxes according to the invention. sen by reacting ethylene copolymer wax according to the invention with Bronsted acid.
  • the amino groups contained in the ethylene copolymer waxes according to the invention are partially or completely protonated.
  • the mixture is advantageously heated to a temperature which is at least 10 ° C., particularly advantageously to a temperature which is at least 30 ° C. above the melting point of the ethylene copolymer wax or waxes according to the invention.
  • the mixture is heated to a temperature which is above the melting point of the ethylene copolymer wax according to the invention melting at the highest temperature.
  • the mixture is advantageously heated to a temperature which is at least 10 ° C. above the melting point of the ethylene copolymer wax melting at the highest temperature.
  • it is particularly advantageously heated to a temperature of at least 30 ° C above the melting point of the ethylene copolymer wax melting at the highest temperature.
  • more Bronsted acid or Bronsted acids can be added than is necessary for the complete protonation of the amino groups of the ethylene copolymer wax or waxes according to the invention, for example an excess of up to 100 mol%, preferably up to 50 mol%.
  • Another object of the present invention are ionic ethylene copolymer waxes, hereinafter also called quaternized ethylene copolymer waxes according to the invention, obtainable by reacting at least one ethylene copolymer wax according to the invention with an alkylating agent R 11 -Z, R 11 being selected from benzyl and CrC 10 alkyl and in particular Benzyl and methyl, and Z is selected from halogen, preferably chlorine, bromine or iodine, and fl 11 SO. -;
  • the amino groups contained in the ethylene copolymer waxes according to the invention are partially or completely alkylated (quaternized).
  • the resulting emulsion is homogenized, for example by mechanical or pneumatic stirring or by shaking. It is advantageously heated to a temperature above the melting point of the ethylene copolymer wax or waxes according to the invention.
  • the mixture is advantageously heated to a temperature which is at least 10 ° C., particularly advantageously to a temperature which is at least 30 ° C. above the melting point of the ethylene copolymer wax or waxes according to the invention.
  • the mixture is heated to a temperature which is above the melting point of the ethylene copolymer wax according to the invention melting at the highest temperature.
  • the mixture is advantageously heated to a temperature which is at least 10 ° C. above the melting point of the ethylene copolymer wax melting at the highest temperature.
  • it is particularly advantageously heated to a temperature which is at least 30 ° C. above the melting point of the ethylene copolymer wax melting at the highest temperature.
  • an excess of base is added, selected from aqueous sodium hydroxide solution and aqueous potassium hydroxide solution, excess based on equivalents of alkylating agent
  • enough alkylating agent is added that at least half, preferably at least 60 mol%, of the amino groups of the ethylene copolymer wax or waxes according to the invention is alkylated.
  • sufficient alkylating agent is added that the amino groups of the ethylene copolymer wax or waxes according to the invention are alkylated quantitatively.
  • an excess of alkylating agent can be added, based on amino groups of the ethylene copolymer wax or waxes according to the invention, for example an excess of up to 100 mol%, preferably up to 50 mol%.
  • the process according to the invention for producing quaternized ethylene copolymer waxes according to the invention gives dispersions, preferably aqueous dispersions, which contain quaternized ethylene copolymer wax according to the invention and are likewise an object of the present invention.
  • the process according to the invention for the production of ionic ethylene copolymer waxes gives dispersions, preferably aqueous dispersions, which contain ionic ethylene copolymer waxes and are likewise an object of the present invention.
  • the solids content of aqueous dispersions according to the invention can be selected within a wide range. Suitable solids contents are, for example, 0.1% by weight to 50% by weight of ionic ethylene copolymer wax.
  • the person skilled in the art can easily adjust the solids content of ionic ethylene copolymer wax during the process according to the invention for producing ionic ethylene copolymer wax by appropriately selecting the proportions of ethylene copolymer wax to Bronsted acid or Bransted acids.
  • Another object of the present invention is the use of ethylene copolymer wax according to the invention and the use of ionic ethylene copolymer wax according to the invention as a microbicidal agent or as a component of microbicidal agents.
  • Another object of the present invention is a method for controlling microorganisms using ethylene copolymer waxes according to the invention or ionic ethylene copolymer waxes according to the invention.
  • ionic ethylene copolymer waxes according to the invention or according to the invention can be applied, for example in the form of their aqueous solution or dispersion, to a substrate which has been attacked by microorganisms.
  • Suitable substrates that can be attacked by microorganisms are, for example, textiles, in particular textiles for the nursing area and for the intimate area.
  • Other substrates to be mentioned by way of example are furniture and appliance surfaces, as well as floors and walls, in particular in toilets, bathrooms, swimming pools, hospitals and in hospitals, in particular in rooms for intensive care and infant care. Facades and roofs are also suitable.
  • Other suitable substrates are foams.
  • ethylene copolymer wax or ionic copolymer wax according to the invention is mixed in paints such as, for example, emulsion paints or in formulations for plasters.
  • the ethylene copolymer waxes according to the invention and the ionic ethylene copolymer waxes according to the invention can also be used for prophylaxis against microorganisms.
  • Another object of the present invention is a method for the prophylactic treatment of substrates by treatment with ethylene copolymer waxes according to the invention or with ionic ethylene copolymer waxes according to the invention, substrates being defined as above.
  • ethylene copolymer waxes according to the invention ionic ethylene copolymer waxes according to the invention and quaternized ethylene copolymer waxes according to the invention into polymers, for example by blending or coextrusion. Microbicidal polymers are obtained.
  • T Reakt0 r is the maximum internal temperature of the high-pressure autoclave.
  • DMA3 N, N-dimethylaminoethyl acrylate
  • PA propionaldehyde
  • ID isododecane (2,2,4,6,6-pentamethylheptane)
  • PA in ID solution of propionaldehyde in isododecane, total volume of the solution.
  • PO tert-butyl peroxypivalate
  • ECW ethylene copolymer wax c (PO): concentration of PO in ID in mol / l The conversion relates to ethylene and is given in% by weight
  • nb not determined.
  • the “content” is to be understood as the proportion of copolymerized ethylene or DMA3 in the respective ethylene copolymer wax.
  • V dynamic melt viscosity, measured at 120 ° C. according to DIN 51562,
  • the amount of ethylene copolymer wax according to Example 1 given in Table 3 was placed in a 2 liter autoclave with anchor stirrer. The mixture was heated to 140 ° C. with stirring and then the amount of 37% by weight aqueous hydrochloric acid given in Table 3 was added dropwise over the course of 30 minutes. The mixture was then stirred at 99 ° C. for a further hour and then cooled to room temperature within 15 minutes. It was filtered with a Perlon filter (100 ⁇ m) and the dispersions 2.1 to 2.4 according to the invention were obtained.
  • Escherichia coli was prepared as a suspension in 0.9% by weight aqueous NaCl and plated out on meat peptone agar plates as a dense lawn. Filter plates (Chromatography Paper, from Whatman, Cat.No. 3030 931) were then placed on the agar plates, which were punched out with a punch and then dried in an autoclave at 20 min, 121 ° C., 1.5 bar.
  • the solution thus obtained was autoclaved in an autoclave at 121 ° C. and 1.5 bar for 20 minutes and then mixed with 20 ml of 10% by weight KH 2 PO 4 solution, 10 ml of vitamin stock solution and
  • the buffered dispersion 3.5 described above was diluted with water to different concentrations (in the range from 2.5% by volume of buffered dispersion 3.5 to 0.001% by volume of buffered dispersion 3.5).
  • the nutrient solutions 3.2.1 and 3.2.2 were inoculated in separate experiments with the microorganisms Escherichia Coli, Bacillus thuringiensis and Pseudomonas putida and mixed with buffered dispersion 3.5 in different concentrations.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Adhesives Or Adhesive Processes (AREA)

Abstract

L'invention concerne des cires de copolymère d'éthylène possédant un poids moléculaire Mw compris entre 1000 et 20 000 g/mol, ces cires contenant comme comonomères incorporés par polymérisation (a) 50 à 95 % en poids d'éthylène, (b) 5 à 50 % en poids d'au moins un comonomère comportant au moins un groupe amino alkylé ou cycloalkylé lié par l'intermédiaire d'un séparateur à un groupe polymérisable, (c) 0 à 30 % en poids d'autres comonomères, chacune des indications de % en poids se rapportant au poids total de cire de copolymère d'éthylène.
EP04787001A 2003-09-30 2004-09-24 Cires de copolymere d'ethylene contenant des groupes amino et leur utilisation Withdrawn EP1678220A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10345798A DE10345798A1 (de) 2003-09-30 2003-09-30 Aminogruppenhaltige Ethylencopolymerwachse und ihre Verwendung
PCT/EP2004/010720 WO2005033155A1 (fr) 2003-09-30 2004-09-24 Cires de copolymere d'ethylene contenant des groupes amino et leur utilisation

Publications (1)

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EP1678220A1 true EP1678220A1 (fr) 2006-07-12

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US (1) US20060257354A1 (fr)
EP (1) EP1678220A1 (fr)
DE (1) DE10345798A1 (fr)
WO (1) WO2005033155A1 (fr)

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CA2637772A1 (fr) * 2006-02-09 2007-08-16 Basf Se Procede de traitement de textiles en polypropylene
WO2007135040A1 (fr) * 2006-05-24 2007-11-29 Basf Se Substrats enduits de polymères oléfiniques pour un procédé d'impression électrophotographique
WO2007141199A2 (fr) * 2006-06-09 2007-12-13 Basf Se Procédé de protection de surfaces métalliques de la corrosion par des milieux liquides par utilisation de copolymères comprenant de l'éthylène et des groupements amino
EP2464681A1 (fr) * 2009-08-10 2012-06-20 Basf Se Fibres cellulosiques modifiées, fabrication et utilisation
US8652247B2 (en) 2010-03-25 2014-02-18 Basf Se PE wax dispersions in the coating of plastics
US9782260B1 (en) * 2014-01-29 2017-10-10 Lucas Anissian Materials and methods for prevention of cold welding, corrosion and tissue overgrowth between medical implant components
GB201708709D0 (en) * 2017-06-01 2017-07-19 Univ York Virus like particle

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CA1326730C (fr) * 1987-01-16 1994-02-01 Tadayuki Ohmae Copolymere d'ethylene et procede pour la production de ce polymere
DE4234324A1 (de) * 1992-10-12 1994-04-14 Basf Ag Härtbare Formmasse
DE19709075A1 (de) * 1997-03-06 1998-09-10 Huels Chemische Werke Ag Verfahren zur Herstellung antimikrobieller Kunststoffe
DE4333680A1 (de) * 1993-10-02 1995-04-06 Basf Ag Copolymerisate auf Ethylenbasis und ihre Verwendung als Fließverbesserer in Erdölmitteldestillaten
JP3499244B2 (ja) * 1993-10-02 2004-02-23 ビーエーエスエフ アクチェンゲゼルシャフト エチレンを基礎とする共重合体及びその鉱油中間留分における流動性改善剤としての使用
DE4341765A1 (de) * 1993-12-08 1995-06-14 Basf Ag Copolymerisate auf Ethylenbasis und ihre Verwendung als Fließverbesserer in Erdölmitteldestillaten
US5717048A (en) * 1994-12-07 1998-02-10 Dai-Ichi Kogyo Seiyaku Co., Ltd. Cation-modified acrylamide or methacrylamide copolymer as well as antistatic agent, thermoplastic resin composition, aqueous composition and thermoplastic resin laminate comprising same
DE19709076A1 (de) * 1997-03-06 1998-09-10 Huels Chemische Werke Ag Verfahren zur Herstellung antimikrobieller Kunststoffe
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DE10345798A1 (de) 2005-04-14
US20060257354A1 (en) 2006-11-16

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