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
  • C08F8/00—Chemical modification by after-treatment
  • C08F8/14—Esterification
• • 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
  • C08F8/00—Chemical modification by after-treatment
  • C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups

Definitions

• Copolymers with varying proportions of ethylene and acrylic acid are widely used. They are characterized by a high linear
• side-chain-modified copolymer waxes of the type mentioned at the outset characterized in that they are produced from waxy copolymers of long-chain ⁇ -olefins with 18 to 60 carbon atoms, methyl acrylate, acrylic acid and / or acrylic acid amides, the carboxyl functionality of which is obtained by chemical reaction with nucleophilic ones Components was modified.
• the nucleophilic components are preferably long-chain alcohols, perfluoroalkyl alcohols, short-chain amines, long-chain amines and / or amino alcohols.
• the long-chain alcohols are preferably tallow fatty alcohol, coconut fatty alcohol, oxo alcohols and / or Guerbet alcohol.
• the perfluoroalcohols are preferably C ⁇ -C-i ⁇ -perfluoroalkylpropanol and distillate cuts of these alcohols.
• Distillate cut Distillation is a physical separation method in which the different boiling points of the constituents (components) of a mixture are used for the separation. In its simplest variant, the liquid dripping from the cooler is successively in small portions and caught separately. This process continues until most of the original volume has been distilled. The composition of the individual fractions is then examined using a suitable method. These fractions are also referred to as distillation cuts. The composition of these fractions depends on the boiling point differences of the individual components and the distillation conditions.
• the short-chain amines are preferably butylamine, dimethylaminopropylamine, diethylaminoethanol, tetramethylpiperidinol and / or triacetone diamine.
• the present object is also achieved by a process for the production of side-chain-modified copolymer waxes, characterized in that long-chain alpha-olefins having 18 to 60 C atoms are first reacted with acrylic acid esters, acrylic acid and / or acrylic acid amides to give long-chain copolymer waxes and then with nucleophilic components to the side chain modified copolymer waxes.
• the nucleophilic components are preferably long-chain alcohols such as tallow fatty alcohol, coconut fatty alcohol, oxo alcohols and / or Guerbet alcohol; perfluoroalkyl alcohol such as C 8 -C 8 perfluoroalkyl propanol 'and distillate cuts of these alcohols; short-chain amines such as butylamine, dimethylaminopropylamine, diethylaminoethanol, tetramethylpiperidinol and / or triacetone diamine; to long-chain amines, such as octylamine, decylamine, dodecylamine, tallow fatty amine, coconut fatty amine, didecylamine and / or cyclohexylamine and / or to alkanolamines, such as diethylaminoethanol, 2,2,6,6-tetramethyl-piperidinol, N-methyl-2,2,6 ,
• long-chain alcohols such as t
• the invention also relates to the use of the side chain-modified copolymer waxes according to the invention in emulsified form for coatings and the water-repellent effect.
• the side chain modified copolymer waxes are also used in micronized form as matting agents, slip agents, anti-scratch agents and to improve chemical resistance.
• carboxyl functionality is explained as follows: When olefins are copolymerized with acrylic acid and acrylic acid esters, polymers are formed which contain carboxylic acid and ester functions. These functions are commonly referred to as carboxyl functions. In the raw materials, it is the functionality of the acid COOH and the methyl ester COOCH3 that are changed to COOR and CONR 1 R 2 in the reaction products according to the invention. Here R is to be understood as meaning alkyl groups which are not CH 3 .
• Comparative Example 1 Copolymer of C3o- ⁇ -olefins with acrylic acid / acrylic acid methyl ester
• the olefin is melted at 100 ° C., the batch is heated to 150 ° C., then di-tert-butyl ester, methyl acrylate and acrylic acid are metered in and the mixture is stirred for 5 hours. The free monomers are distilled off.
• Acrylic acid methyl ester 1.5 mol of di-tert-butyl peroxide 5% by weight on acrylic acid methyl ester
• the olefin is melted at 100 ° C., the mixture is heated to 150 ° C., then di-tert-butyl peroxide and methyl acrylate are metered in and the mixture is stirred for 3 hours. The free monomers are distilled off.
• Acrylic acid methyl ester 2.5 mol of di-tert-butyl peroxide 5% by weight on acrylic acid methyl ester
• the olefin is melted at 100 ° C., the batch is heated to 150 ° C., then di-tert-butyl peroxide and methyl acrylate are metered in and the mixture is stirred for 5 hours. The free monomers are distilled off.
• Example 1 copolymer wax modified with tallow fatty alcohol side chains copolymer according to Comparative Example 3 1 mol
• the copolymer is melted at 100 ° C., the catalyst (Na methylate) and the alcohol component (tallow fatty alcohol) are added and the mixture is heated to 180 ° C. At this temperature, the mixture is stirred for 7 hours and the methanol liberated is distilled off. Then vacuum is applied to distill off residues of methanol and other alcohols, it is neutralized with phosphoric acid, cooled to 120 ° C. and filtered.
• Viscosity number (cm 3 / g): 80 Dropping point (° C): 74.3
• the product is suitable as a lubricant for PVC with a light color and adjustable polarity via the degree of exchange, and as a dispersing aid for pigments
• Copolymer wax modified with perfluoroalkylpropanol (Ci 2 -C . ) Side chains
• the product is suitable for the production of emulsions with a water-repellent effect, car polishes, textile emulsions as well as for the production of micronisates with a particle size of approx. 10 microns and for the adjustment of gloss and slipperiness in aqueous and solvent-based paints.
• Test wax according to Example 3 5.0 g
• Example 4 Triacetone diamine-modified chain wax-modified copolymer wax Copolymer according to Comparative Example 4 1 mol
• the copolymer is melted at 100 ° C., the catalyst (/ ®Tc ascat 4102) and the amine component are added and the mixture is heated to 190 ° C. At this temperature, the mixture is stirred for 7 hours and the liberated methanol is distilled off. Then vacuum is applied in order to distill off residual methanol and amine, the mixture is cooled to 150 ° C. and filtered.
• Viscosity number (cm 3 / g): 136 Drop point (° C): 120 ° C Alkali number: 67.8 Melt viscosity (170 ° C): 572 mPas
• Example 5 Copolymer wax modified with 2,2,6,6-tetramethylpiperidinol side chain
• the copolymer is melted at 100 ° C., the catalyst and the amine component are added and the mixture is heated to 190 ° C. At this temperature, the mixture is stirred for 7 hours and the methanol liberated is distilled off. Then vacuum is applied to distill off residues of methanol and amine, it is cooled to 150 ° C. and filtered.
• the product is used as a processing aid in polypropylene with light protection.
• the copolymer is melted at 100 ° C, the catalyst and the amine component are added and the mixture is heated to 190 ° C. At this temperature, the mixture is stirred for 7 hours and the methanol liberated is distilled off. Then vacuum is applied to distill off residues of methanol and amine, it is cooled to 150 ° C. and filtered. Acid number: 16
• the copolymer is melted at 100 ° C., the catalyst and the amine component are added and the mixture is heated to 190 ° C. At this temperature, the mixture is stirred for 7 hours and the methanol liberated is distilled off. Then vacuum is applied to distill off residues of methanol and amine, it is cooled to 150 ° C. and filtered.
• Wax emulsifier 2.25 g
• the copolymer is melted at 100 ° C., the catalyst and the amine component are added and the mixture is heated to 190 ° C. At this temperature, the mixture is stirred for 7 hours and the methanol liberated is distilled off. Then vacuum is applied to distill off residues of methanol and amine, it is cooled to 150 ° C. and filtered.

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• Chemical & Material Sciences (AREA)
• General 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)

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• 2002
  • 2002-06-08 DE DE10225652A patent/DE10225652B4/de not_active Expired - Fee Related
• 2003
  • 2003-05-30 WO PCT/EP2003/005671 patent/WO2003104289A1/de not_active Ceased
  • 2003-05-30 US US10/516,929 patent/US20060036013A1/en not_active Abandoned
  • 2003-05-30 JP JP2004511356A patent/JP2005529204A/ja not_active Withdrawn
  • 2003-05-30 EP EP03732502A patent/EP1523507A1/de not_active Withdrawn
  • 2003-05-30 CN CNB03813165XA patent/CN1284803C/zh not_active Expired - Fee Related

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