CN104761684A - Waterborne acrylic modified saturated polyester resin - Google Patents

Waterborne acrylic modified saturated polyester resin Download PDF

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Publication number
CN104761684A
CN104761684A CN201410559256.6A CN201410559256A CN104761684A CN 104761684 A CN104761684 A CN 104761684A CN 201410559256 A CN201410559256 A CN 201410559256A CN 104761684 A CN104761684 A CN 104761684A
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CN
China
Prior art keywords
parts
acid
polyester resin
saturated polyester
modified saturated
Prior art date
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Pending
Application number
CN201410559256.6A
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Chinese (zh)
Inventor
陈明
秦文
王英
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.)
LANGFANG JINHWEILI INDUSTRIAL COATINGS Co Ltd
BEIJING JINHWEILI APPLIED CHEMICAL PRODUCTS Co Ltd
Original Assignee
LANGFANG JINHWEILI INDUSTRIAL COATINGS Co Ltd
BEIJING JINHWEILI APPLIED CHEMICAL PRODUCTS Co Ltd
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Application filed by LANGFANG JINHWEILI INDUSTRIAL COATINGS Co Ltd, BEIJING JINHWEILI APPLIED CHEMICAL PRODUCTS Co Ltd filed Critical LANGFANG JINHWEILI INDUSTRIAL COATINGS Co Ltd
Priority to CN201410559256.6A priority Critical patent/CN104761684A/en
Publication of CN104761684A publication Critical patent/CN104761684A/en
Pending legal-status Critical Current

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    • 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

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  • 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

The invention relates to a waterborne acrylic modified saturated polyester resin, which is synthesized from the following raw materials by the weight: 5-25 parts of polybasic acid, 15-40 parts of polyols, 1-3 parts of a cosolvent, 5-20 parts of acrylic monomer I, 0.5-10 parts of acrylic monomers II, 0.01-8 parts of an initiator, 0.5-10 parts of a neutralizing agent, 2-20 parts of tertiary carbonate glycidyl ester and 40-50 deionized water. The waterborne acrylic modified saturated polyester resin prepared by the invention has the advantages of excellent stability, high solid, low viscosity and low VOC content, and is mainly used in amino baking finish for waterborne coatings.

Description

A kind of aqueous acrylic modified saturated polyester resin
Technical field
The present invention relates to a kind of aqueous acrylic modified saturated polyester resin, belong to water-borne coatings field.
Background technology
Water-borne coatings is subject to applying more and more widely as a kind of low VOC content coating.And water-borne coatings is because its construction is solid containing lower, be difficult to the high-decoration effect reaching dissolubility type.Water-base resin is as the filmogen of water-borne coatings, and the solid of its water dispersion plays a decisive role on the performance of paint film with on affecting environment containing, viscosity and VOC content.Saturated polyester has high gloss, high plumpness, excellent weathering resistance are applied in medium-to-high grade amino-stoving varnish and polyurethane finish.But there is construction at present admittedly containing the defect low, facile hydrolysis, VOC content are high in water-based saturated polyester resin product.
Summary of the invention
Technical problem to be solved by this invention is to provide a kind of aqueous acrylic modified saturated polyester resin, aqueous acrylic modified saturated polyester resin prepared by the present invention has the characteristic of excellent stability, high solid, low viscosity and low VOC content, have great importance, this resin is mainly used in water-borne coatings amino-stoving varnish.
The technical scheme that the present invention solves the problems of the technologies described above is as follows: a kind of aqueous acrylic modified saturated polyester resin, by raw material weight number, by following Material synthesis: 5 ~ 25 parts of polyprotonic acids, 15 ~ 40 parts of polyvalent alcohols, 1 ~ 3 part of solubility promoter, 5 ~ 20 parts of Acrylic Acid Monomer I, 0.5 ~ 10 part of Acrylic Acid Monomer II, 0.01 ~ 8 part of initiator, 0.5 ~ 10 part of neutralizing agent, 2 ~ 20 parts of tertiary carbonic acid glycidyl esters, 40 ~ 50 parts of deionized waters.
Wherein, described Acrylic Acid Monomer I is one or more in isobornyl methacrylate, methyl acrylate, methyl methacrylate, ethyl propenoate, β-dimethyl-aminoethylmethacrylate, vinylbenzene, butyl acrylate, butyl methacrylate, butyl methacrylate, lauryl acrylate, lauryl methacrylate(LMA), ethyl acrylate, methacrylic acid-2-ethylhexyl, Hydroxyethyl acrylate, hydroxyethyl methylacrylate, Propylene glycol monoacrylate, Rocryl 410, hy-droxybutyl;
Described Acrylic Acid Monomer II is one or more in vinylformic acid, methacrylic acid, Hydroxyethyl acrylate, hydroxyethyl methylacrylate, Propylene glycol monoacrylate, Rocryl 410, hy-droxybutyl, methyl acrylate, methyl methacrylate.
For described aqueous acrylic modified saturated polyester resin, the preferable range of various raw material is: 15 ~ 25 parts of polyprotonic acids, 15 ~ 25 parts of polyvalent alcohols, 1 ~ 3 part of solubility promoter, 5 ~ 15 parts of Acrylic Acid Monomer I, 0.5 ~ 2 part of Acrylic Acid Monomer II, 1 ~ 5 part of initiator, 0.5 ~ 5 part of neutralizing agent, 3 ~ 8 parts of tertiary carbonic acid glycidyl esters, 40 ~ 50 parts of deionized waters.
On the basis of technique scheme, the present invention can also do following improvement.
Further, described polyprotonic acid is one or more in hexanodioic acid, 1, 4-succinic acid, hexanodioic acid, m-phthalic acid, terephthalic acid, 1,4 cyclohexanedicarboxylic acid, trimellitic acid 1,2-anhydride, HHPA, MALEIC ANHYDRIDE, fumaric acid.
Further, described polyvalent alcohol is 1, ammediol, neopentyl glycol, 1,4-butyleneglycol, 1,6-hexylene glycol, 1,4 cyclohexane dimethanol, hydroxypivalyl hydroxypivalate, 2,2, one or more in 4-trimethylammonium-1,3 pentanediol, 2-butyl-2-ethyl-1,3-PD, tetramethylolmethane, TriMethylolPropane(TMP), trimethylolethane.
Further, described solubility promoter is one or more in propylene glycol monobutyl ether, Virahol, isopropylcarbinol, propyl carbinol, ethylene glycol monobutyl ether, propylene glycol monomethyl ether, butyl, 1-Methoxy-2-propyl acetate, ethylene glycol ethyl ether, dipropylene glycol methyl ether.
Further, described initiator is one or more in Diisopropyl azodicarboxylate, benzoyl peroxide, tertbutyl peroxide, ditertiary butyl peroxide, two t-amyl peroxy compounds, isopropyl benzene hydroperoxide, peroxidized t-butyl perbenzoate, the peroxidation trimethylacetic acid tert-butyl ester.
Further, described neutralizing agent is one or more in triethylamine, 2-amino-2-methyl-1-propanol, trolamine, diethanolamine, N, N-dimethylethanolamine, ammoniacal liquor.
Present invention also offers the preparation method of aqueous acrylic modified saturated polyester resin as above, comprising:
1) in the reactor that whipping appts, reflux condensate device, Dropping feeder and temperature regulating device are housed, drop into polyprotonic acid, tertiary carbonic acid glycidyl ester (E10P), polyvalent alcohol, pass into nitrogen, slowly be heated to 110 ~ 190 DEG C, insulation 0.5 ~ 3h, slowly be warming up to 200 ~ 250 DEG C, insulated and stirred 3 ~ 6h, refluxing xylene to the acid number adding this step charging capacity 2 ~ 4% is 0 ~ 20mgKOH/g, and reaction process controls to heat up in a steamer a temperature and is less than 100 DEG C;
2) be cooled to 80 ~ 190 DEG C, add solubility promoter;
3) be cooled to 80 ~ 190 DEG C, drip and account for the initiator of initiator total amount 50 ~ 70% and the mixture of Acrylic Acid Monomer I, 3.5 ~ 4h drips off under stirring;
4) 80 ~ 190 DEG C of droppings account for the initiator of initiator total amount 20 ~ 30% and the mixture of Acrylic Acid Monomer II, and 0.5 ~ 1h drips off under stirring;
5) residue initiator is added, 80 ~ 190 DEG C of insulated and stirred 4h;
6) temperature controls, at 50 ~ 160 DEG C, to add neutralizing agent, stirs 30min;
7) when the temperature of reactor is less than 100 DEG C, slowly add deionized water, by resin admittedly containing being adjusted to 45 ~ 50%, filtering discharging, obtaining aqueous acrylic modified saturated polyester resin.
Reaction principle of the present invention:
1. synthesize the vibrin with unsaturated link(age) and sterically hindered structure;
2. grafting adjustment TG Acrylic Acid Monomer and or functional Acrylic Acid Monomer;
3. grafting provide water-soluble and or functional Acrylic Acid Monomer; form the spheroidal structure of class of intramolecule hydrophobic external hydrophilic, this special structure was both protected ester is strong, can reduce again the winding between molecular resin; reduce the viscosity of resin, improve construction and admittedly contain.
The invention has the beneficial effects as follows:
A. the aqueous acrylic modified saturated polyester resin prepared adopts tertiary carbonic acid glycidyl ester modification to increase the space steric hindrance group protection strong to ester, improves the anti-hydrolytic performance of resin.
B. substep drips Acrylic Acid Monomer, namely first drip adjustment TG Acrylic Acid Monomer and or functional Acrylic Acid Monomer, again drip provide water-soluble and or functional Acrylic Acid Monomer, form the spheroidal structure of class of intramolecule hydrophobic external hydrophilic, realize acrylic resin and the viscosity that modification reduces resin is carried out to saturated polyester resin, reduce the add-on of solubility promoter, improve construction and admittedly contain, thus reduce VOC content.
The water dispersion of aqueous acrylic modified saturated polyester resin prepared by the present invention is admittedly containing 45 ~ 50%, viscosity≤1000CP, VOC content≤20g/kg (water dispersion), normal temperature storage 6 months is without layering, precipitation equistability problem, toast 20 ~ 30min or 110 ~ 130 DEG C with 140 ~ 160 DEG C, the amino-stoving varnish varnish that the aminoresin of this resin and complete methyl-etherified aminoresin or high imino-is prepared simultaneously and toast 20 ~ 30min, gloss >=95,60 ° of angles, clarity (DOI) >=95.Also can be mixed with colored paint, decorative effect can with the comparing favourably of dissolubility type Amino-Polyester baking vanish, hardness is high, and snappiness is good, has excellent water tolerance, solvent resistance, chemical-resistant and ageing resistance simultaneously.
Accompanying drawing explanation
Fig. 1 is the structural representation of a kind of aqueous acrylic modified saturated polyester resin of the specific embodiment of the invention.
Wherein 1 is graft acrylic acid (hydrophilic layer) 2 for polyester 3 is graft acrylic acid (hydrophobic layer).
Embodiment
Below in conjunction with the drawings and specific embodiments, the invention will be further described.Be described principle of the present invention and feature below, example, only for explaining the present invention, is not intended to limit scope of the present invention.
Concrete implementation step is as follows:
1) in the reaction flask of 1L that whipping appts, reflux condensate device, Dropping feeder and temperature regulating device are housed, polyprotonic acid, E10P, polyvalent alcohol is dropped into, pass into nitrogen, slowly be heated to 190 DEG C, insulation 1h, slowly be warming up to 250 DEG C, insulation 6h, the refluxing xylene adding this step charging capacity 3% is less than 20mgKOH/g to acid number, and reaction process controls to heat up in a steamer a temperature and is less than 100 DEG C;
2) be cooled to 110 DEG C, add solubility promoter;
3) 120 DEG C drip the mixture of Acrylic Acid Monomer I and initiator total amount 60%, stir lower 4h and drip off;
4) 120 DEG C drip the mixture of Acrylic Acid Monomer II and initiator total amount 25%, stir lower 1h and drip off;
5) residue initiator is added, 120 DEG C of insulated and stirred 4h, cooling;
6) be down to 80 DEG C when temperature in reaction flask and add neutralizing agent, stir 30min;
7) be down to 40 DEG C when temperature in reaction flask and slowly add deionized water, by resin admittedly containing being adjusted to 45 ~ 50%, filtering discharging, obtaining aqueous acrylic modified saturated polyester resin.
Concrete proportioning is in table 1
Table 1
The aqueous acrylic modified saturated polyester resin above embodiment 1,2,3,4,5 prepared and the special aminoresin 303 of cyanogen are with (10-5): 1 or with cyanogen spy aminoresin 327 with (10-6): 1 mixes, add water and viscosity is adjusted to 30-40s (being coated with-4 glasss) and sprays plate (base material is tinplate and sub-light welding glass plate), 140-150 DEG C of baking 20-40min or 110-130 DEG C of baking 20-40min.Lacquer formulation is as follows:
Table 2
Above flow agent BYK381 is purchased from German Bi Ke chemistry (BYK, bikehuaxue) product, CYCAT600 is the product of the special engineering materials (Cytec Industries Inc., CYTEC, qingtegongchengcailiao) of purchased from American cyanogen.
Obtain paint film property as follows:
Table 3
Remarks:
BYK clarity instrument: clarity is the objective criterion of lightness and gloss, BYK clarity instrument is the instrument of a measurement clarity of German Bi Ke chemical production, and useful range 0 ~ 100, numerical value is larger, and clarity is better.
The foregoing is only preferred embodiment of the present invention, not in order to limit the present invention, within the spirit and principles in the present invention all, any amendment done, equivalent replacement, improvement etc., all should be included within protection scope of the present invention.

Claims (7)

1. an aqueous acrylic modified saturated polyester resin, it is characterized in that, by the weight parts of each raw material of synthetic resins, for: 5 ~ 25 parts of polyprotonic acids, 15 ~ 40 parts of polyvalent alcohols, 1 ~ 3 part of solubility promoter, 5 ~ 20 parts of Acrylic Acid Monomer I, 0.5 ~ 10 part of Acrylic Acid Monomer II, 0.01 ~ 8 part of initiator, 0.5 ~ 10 part of neutralizing agent, 2 ~ 20 parts of tertiary carbonic acid glycidyl esters, 40 ~ 50 parts of deionized waters;
Described Acrylic Acid Monomer I is one or more in isobornyl methacrylate, methyl acrylate, methyl methacrylate, ethyl propenoate, β-dimethyl-aminoethylmethacrylate, vinylbenzene, butyl acrylate, butyl methacrylate, lauryl acrylate, lauryl methacrylate(LMA), ethyl acrylate, methacrylic acid-2-ethylhexyl, Hydroxyethyl acrylate, hydroxyethyl methylacrylate, Propylene glycol monoacrylate, Rocryl 410, hy-droxybutyl;
Described Acrylic Acid Monomer II is one or more in vinylformic acid, methacrylic acid, Hydroxyethyl acrylate, hydroxyethyl methylacrylate, Propylene glycol monoacrylate, Rocryl 410, hy-droxybutyl, methyl acrylate, methyl methacrylate.
2. aqueous acrylic modified saturated polyester resin according to claim 1, the preferable range of various raw material is: 15 ~ 25 parts of polyprotonic acids, 15 ~ 25 parts of polyvalent alcohols, 1 ~ 3 part of solubility promoter, 5 ~ 15 parts of Acrylic Acid Monomer I, 0.5 ~ 2 part of Acrylic Acid Monomer II, 1 ~ 5 part of initiator, 0.5 ~ 5 part of neutralizing agent, 3 ~ 8 parts of tertiary carbonic acid glycidyl esters, 40 ~ 50 parts of deionized waters.
3. aqueous acrylic modified saturated polyester resin according to claim 1 and 2, described polyprotonic acid is hexanodioic acid, 1, one or more in 4-succinic acid, m-phthalic acid, terephthalic acid, 1,4 cyclohexanedicarboxylic acid, trimellitic acid 1,2-anhydride, HHPA, MALEIC ANHYDRIDE, fumaric acid.
4. aqueous acrylic modified saturated polyester resin according to claim 1 and 2, described polyvalent alcohol is 1, ammediol, neopentyl glycol, 1,4-butyleneglycol, 1,6-hexylene glycol, 1,4 cyclohexane dimethanol, hydroxypivalyl hydroxypivalate, 2,2, one or more in 4-trimethylammonium-1,3 pentanediol, 2-butyl-2-ethyl-1,3-PD, tetramethylolmethane, glycerol, TriMethylolPropane(TMP), trimethylolethane.
5. aqueous acrylic modified saturated polyester resin according to claim 1 and 2, described solubility promoter is one or more in propylene glycol monobutyl ether, Virahol, isopropylcarbinol, propyl carbinol, ethylene glycol monobutyl ether, propylene glycol monomethyl ether, butyl, 1-Methoxy-2-propyl acetate, ethylene glycol ethyl ether, dipropylene glycol methyl ether.
6. aqueous acrylic modified saturated polyester resin according to claim 1 and 2, described initiator is one or more in Diisopropyl azodicarboxylate, benzoyl peroxide, tertbutyl peroxide, ditertiary butyl peroxide, two t-amyl peroxy compounds, isopropyl benzene hydroperoxide, peroxidized t-butyl perbenzoate, the peroxidation trimethylacetic acid tert-butyl ester.
7. aqueous acrylic modified saturated polyester resin as claimed in claim 1 or 2, described neutralizing agent is one or more in triethylamine, 2-amino-2-methyl-1-propanol, trolamine, diethanolamine, N, N-dimethylethanolamine, ammoniacal liquor.
CN201410559256.6A 2013-10-21 2014-10-20 Waterborne acrylic modified saturated polyester resin Pending CN104761684A (en)

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CN201310495773.7A CN103554381A (en) 2013-10-21 2013-10-21 Water-based acrylic acid modified saturated polyester resin and preparation method thereof
CN2013104957737 2013-10-21
CN201410559256.6A CN104761684A (en) 2013-10-21 2014-10-20 Waterborne acrylic modified saturated polyester resin

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