WO2015058681A1 - Procédé de préparation d'une résine de polyester saturée à modification acrylique à base d'eau - Google Patents

Procédé de préparation d'une résine de polyester saturée à modification acrylique à base d'eau Download PDF

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Publication number
WO2015058681A1
WO2015058681A1 PCT/CN2014/089104 CN2014089104W WO2015058681A1 WO 2015058681 A1 WO2015058681 A1 WO 2015058681A1 CN 2014089104 W CN2014089104 W CN 2014089104W WO 2015058681 A1 WO2015058681 A1 WO 2015058681A1
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WO
WIPO (PCT)
Prior art keywords
parts
polyester resin
saturated polyester
acid
acrylate
Prior art date
Application number
PCT/CN2014/089104
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English (en)
Chinese (zh)
Inventor
程建军
秦文
王英
Original Assignee
北京金汇利应用化工制品有限公司
廊坊金汇利工业涂料有限公司
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Application filed by 北京金汇利应用化工制品有限公司, 廊坊金汇利工业涂料有限公司 filed Critical 北京金汇利应用化工制品有限公司
Publication of WO2015058681A1 publication Critical patent/WO2015058681A1/fr

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Classifications

    • 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
    • C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
    • C09D167/06—Unsaturated polyesters having carbon-to-carbon unsaturation
    • 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
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C08F220/1804—C4-(meth)acrylate, e.g. butyl (meth)acrylate, isobutyl (meth)acrylate or tert-butyl (meth)acrylate
    • 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
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C08F220/1808—C8-(meth)acrylate, e.g. isooctyl (meth)acrylate or 2-ethylhexyl (meth)acrylate
    • 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
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C08F220/1811—C10or C11-(Meth)acrylate, e.g. isodecyl (meth)acrylate, isobornyl (meth)acrylate or 2-naphthyl (meth)acrylate
    • 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
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/20—Esters of polyhydric alcohols or phenols, e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(meth)acrylate

Definitions

  • the invention relates to a preparation method of an aqueous acrylic modified saturated polyester resin, and belongs to the field of water-based coatings.
  • Waterborne coatings are becoming more and more widely used as a low VOC coating.
  • the solid content, viscosity and VOC content of the aqueous dispersion play a decisive role in the performance of the paint film and on the environment.
  • Saturated polyester has high gloss, high fullness and excellent weather resistance for medium and high grade amino baking varnishes and polyurethane topcoats.
  • the current aqueous saturated polyester resin products have the defects of low solid content, easy hydrolysis, and high VOC content.
  • the technical problem to be solved by the present invention is to provide a preparation method of an aqueous acrylic modified saturated polyester resin, which has excellent stability, high solid content, low viscosity and low VOC. The characteristics of the content are of great significance.
  • the resin is mainly used in the amino baking varnish for waterborne coatings.
  • an aqueous acrylic modified saturated polyester resin which is synthesized from the following raw materials by weight of the raw materials: 5 to 25 parts of polybasic acid, 15 to 40 parts of polyhydric alcohol, 1 to 3 parts of cosolvent, 5 to 20 parts of acrylic monomer I, 0.5 to 10 parts of acrylic monomer II, 0.01 to 8 parts of initiator, 0.5 to 10 parts of neutralizing agent, 2 to 20 parts of glycidyl tert-carbonate, 40 to 50 parts of deionized water.
  • the acrylic monomer I is isobornyl methacrylate, methyl acrylate, methyl propyl acrylate Methyl enoate, ethyl acrylate, ethyl methacrylate, styrene, butyl acrylate, butyl methacrylate, butyl methacrylate, lauryl acrylate, lauryl methacrylate, 2-ethyl acrylate
  • the acrylic monomer II is acrylic acid, methacrylic acid, hydroxyethyl acrylate, hydroxyethyl methacrylate, hydroxypropyl acrylate, hydroxypropyl methacrylate, hydroxybutyl acrylate, methyl acrylate, methacrylic acid One or more of the esters.
  • the preferred range of various raw materials is: 15 to 25 parts of polybasic acid, 15 to 25 parts of polyhydric alcohol, 1 to 3 parts of a cosolvent, and 5 to 15 parts of an acrylic monomer I. 0.5 to 2 parts of acrylic monomer II, 1 to 5 parts of initiator, 0.5 to 5 parts of neutralizing agent, 3 to 8 parts of glycidyl tert-carbonate, and 40 to 50 parts of deionized water.
  • the present invention can also be improved as follows.
  • the polybasic acid is adipic acid, 1,4-succinic acid, adipic acid, isophthalic acid, terephthalic acid, 1,4-cyclohexanedicarboxylic acid, trimellitic anhydride, hexahydrophthalic anhydride, cis One or more of butylene dianhydride and fumaric acid.
  • the polyol is 1,3-propanediol, neopentyl glycol, 1,4-butanediol, 1,6-hexanediol, 1,4-cyclohexanedimethanol, hydroxypivalic acid hydroxyl new Amyl ester, 2,2,4-trimethyl-1,3 pentanediol, 2-butyl-2-ethyl-1,3-propanediol, pentaerythritol, trimethylolpropane, trimethylolethane One or several of them.
  • the co-solvent is propylene glycol monobutyl ether, isopropanol, isobutanol, n-butanol, ethylene glycol monobutyl ether, propylene glycol methyl ether, diethylene glycol butyl ether, propylene glycol methyl ether acetate, ethylene One or more of alcohol ether and dipropylene glycol methyl ether.
  • the initiator is azobisisobutyronitrile, benzoyl peroxide, t-butyl hydroperoxide, di-tert-butyl peroxide, di-tert-amyl peroxide, cumene hydroperoxide, One or more of tert-butyl peroxybenzoate and t-butyl peroxypivalate.
  • the neutralizing agent is one or more of triethylamine, 2-amino-2-methyl-1-propanol, triethanolamine, diethanolamine, N,N-dimethylethanolamine, and ammonia water.
  • the present invention provides a method for preparing an aqueous acrylic modified saturated polyester resin as described above, comprising:
  • reaction process control head temperature is less than 100 ° C;
  • the first stage reaction temperature in the step (1) is 150 to 185 ° C
  • the second stage reaction temperature is 210 to 235 ° C
  • reaction temperature in the step (3) and the step (4) is in the range of 125 to 180 °C.
  • the raw material range is 5 to 25 parts of polybasic acid, 15 to 40 parts of polyhydric alcohol, 1 to 3 parts of a cosolvent, 5 to 20 parts of an acrylic monomer I, and 0.5 to 10 parts of acrylic acid.
  • Monomer II 0.01-8 parts of initiator, 0.5-10 parts neutralizer, 2-20 parts of glycidyl tert-carbonate, 40 ⁇ 50 parts of deionized water.
  • the preferred range of various raw materials is: 15 to 25 parts of polybasic acid, 15 to 25 parts of polyhydric alcohol, 1 to 3 parts of a co-solvent, 5 to 15 parts of an acrylic monomer I, 0.5 to 2 parts of an acrylic monomer II, 1 to 5 Ingredients, 0.5 to 5 parts neutralizer, 3 to 8 parts of glycidyl tert-carbonate, 40 to 50 parts of deionized water.
  • Grafting provides a water-soluble and or functional acrylic monomer to form a spherical-like structure that is hydrolyzed outside the molecule. This special structure protects both ester and entanglement between resin molecules. Reduce the viscosity of the resin and increase the solid content of the construction.
  • the prepared aqueous acrylic modified saturated polyester resin modified with glycidyl tert-carbonate increases the protection of the sterically hindered group on the ester and improves the hydrolysis resistance of the resin.
  • Adding the acrylic monomer stepwise that is, first adding the acryl monomer and the functional acrylic monomer to adjust the TG, and then adding the water-soluble and or functional acrylic monomer to form a molecular internal hydrophobic external pro
  • the spherical structure of water enables the acrylic resin to modify the saturated polyester resin to lower the viscosity of the resin, reduce the amount of the co-solvent added, and increase the solid content of the construction, thereby reducing the VOC content.
  • the structure diagram is as follows:
  • the aqueous dispersion of the aqueous acrylic modified saturated polyester resin prepared by the invention has solid content of 45-50%, viscosity ⁇ 1000CP, VOC content ⁇ 20g/kg (aqueous dispersion), storage at room temperature for 6 months without delamination, sedimentation, etc. Stability problem, at the same time, the amino baking varnish prepared with the resin and fully methylated amino resin or high imino amino resin is baked at 140-160 ° C for 20-30 min or 110-130 ° C for 20-30 min, 60 ° angle Gloss ⁇ 95, vividness (DOI) ⁇ 95. It can also be used as a color paint.
  • the decorative effect is comparable to that of a soluble polyester amino baking varnish. It has high hardness and good flexibility. It also has excellent water resistance, solvent resistance, chemical resistance and aging resistance.
  • aqueous acrylic modified saturated polyester resin prepared in the above Examples 1, 2, 3, 4, 5 and the cyano amino resin 303 were (10-5):1 or with the cyanoamino resin 327 (10-6). :1 mixed Evenly, add water to adjust the viscosity to 30-40s (coating - 4 cups) spray plate (the substrate is tinplate and matt black glass plate), baking at 140-150 ° C for 20-40min or 110-130 ° C for 20-40min .
  • the varnish formula is as follows:
  • the above leveling agent BYK381 is a product purchased from BYK (bikehuaxue), and CYCAT600 is a product purchased from Cytec Industries Inc. (CYTEC, qingtegongchengcailiao).
  • the properties of the paint film are as follows:
  • BYK Freshness Analyzer Brightness is the objective criterion for brightness and gloss.
  • BYK is a kind of instrument for measuring the vividness of BYK Chemical. The measurement range is from 0 to 100. The larger the value, The better the better.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Paints Or Removers (AREA)
  • Macromonomer-Based Addition Polymer (AREA)

Abstract

La présente invention porte sur un procédé de préparation d'une résine de polyester saturée à modification acrylique à base d'eau. Tout d'abord, un polyacide, un polyol, et un versatate de glycidyle sont utilisés pour synthétiser une résine de polyester saturée, ensuite, la résine de polyester saturée est modifiée à l'aide d'un monomère acrylique sous l'effet d'un amorceur, puis, un agent neutralisant est ajouté tout en ajustant la teneur en solides avec de l'eau, permettant ainsi d'obtenir la résine de polyester saturée à modification acrylique à base d'eau. La résine de polyester saturée à modification acrylique à base d'eau préparée par l'invention présente une excellente stabilité, une teneur élevée en solides, une faible viscosité, et une faible teneur en COV et est applicable principalement comme peinture amino destinée à être utilisée dans un revêtement à base d'eau.
PCT/CN2014/089104 2013-10-21 2014-10-21 Procédé de préparation d'une résine de polyester saturée à modification acrylique à base d'eau WO2015058681A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CN201310495773.7A CN103554381A (zh) 2013-10-21 2013-10-21 一种水性丙烯酸改性饱和聚酯树脂及其制备方法
CN201310495773.7 2013-10-21

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WO2015058681A1 true WO2015058681A1 (fr) 2015-04-30

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PCT/CN2014/089109 WO2015058685A1 (fr) 2013-10-21 2014-10-21 Résine aqueuse de polyester saturé modifié par de l'acide acrylique
PCT/CN2014/089104 WO2015058681A1 (fr) 2013-10-21 2014-10-21 Procédé de préparation d'une résine de polyester saturée à modification acrylique à base d'eau

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Cited By (1)

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WO2018041128A1 (fr) * 2016-08-30 2018-03-08 河北晨阳工贸集团有限公司 Peinture aminée aqueuse à cuire et son procédé de préparation

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