CN114989362B - Functional polyfunctional siloxane prepolymer acrylate emulsion and preparation method thereof - Google Patents

Functional polyfunctional siloxane prepolymer acrylate emulsion and preparation method thereof Download PDF

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CN114989362B
CN114989362B CN202210811464.5A CN202210811464A CN114989362B CN 114989362 B CN114989362 B CN 114989362B CN 202210811464 A CN202210811464 A CN 202210811464A CN 114989362 B CN114989362 B CN 114989362B
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siloxane prepolymer
emulsion
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CN114989362A (en
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袁小刚
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Anhui Kebang Resin Technology Co ltd
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    • 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
    • C08F275/00—Macromolecular compounds obtained by polymerising monomers on to polymers of monomers containing phosphorus, selenium, tellurium or a metal as defined in group C08F30/00
    • 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
    • C08F230/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
    • C08F230/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal
    • C08F230/08—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon
    • C08F230/085—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon the monomer being a polymerisable silane, e.g. (meth)acryloyloxy trialkoxy silanes or vinyl trialkoxysilanes

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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)
  • Paints Or Removers (AREA)
  • Silicon Polymers (AREA)

Abstract

The invention discloses a polyfunctional siloxane prepolymer modified acrylic emulsion and a preparation method thereof, wherein the acrylic emulsion comprises the following components: 100 parts by weight of methyl methacrylate, 20-70 parts by weight of butyl acrylate, 10-30 parts by weight of hydroxy acrylic ester monomer, 1-5 parts by weight of polyfunctional siloxane prepolymer, 0.5 part by weight of initiator ammonium persulfate, 1-2 parts by weight of emulsifier, 1 part by weight of pH regulator ammonia water and 200 parts by weight of deionized water. The multi-functionality siloxane prepolymer is obtained by the reaction of a small-molecule silane coupling agent and a double unsaturated bond functional monomer under a catalyst, has large molecular weight, has the functionality of more than 6, can be introduced into a main chain or a side chain of acrylic ester through free radical polymerization or hydroxyl condensation, can greatly improve the crosslinking degree of resin by a small amount of addition, and can improve the water resistance and corrosion resistance of a cured paint film by introducing a large amount of silicon into a resin structure.

Description

Functional polyfunctional siloxane prepolymer acrylate emulsion and preparation method thereof
Technical Field
The invention relates to the technical field of industrial paint resin synthesis, in particular to a functional polyfunctional siloxane prepolymer modified acrylic emulsion and a preparation method thereof.
Background
The traditional silicone-acrylate emulsion is prepared by adding a proper auxiliary agent into a silane coupling agent containing unsaturated bonds and an acrylic monomer, and polymerizing the emulsion through a core-shell polymerization process, and the introduction of an organosilicon monomer improves the weather resistance, chemical resistance and hydrophobicity of a paint film, has low surface energy and is not easy to pollute, and is widely applied to the field of environment-friendly building paint.
But the silane coupling agent used in the common silicone-acrylate emulsion has small molecular weight, low functionality and less addition, and the performance of the paint film is not obviously improved.
Disclosure of Invention
Therefore, the technical problem to be solved by the invention is to provide the functional multi-functionality siloxane prepolymer modified acrylic emulsion and the preparation method thereof, the multi-functionality siloxane prepolymer is prepared by a small-molecule silane coupling agent and a double unsaturated bond functional monomer under the action of a catalyst, the acrylic emulsion is modified, the crosslinking degree of the resin can be greatly improved by a small amount of the acrylic emulsion, a large amount of silicon is introduced into the resin structure, and the water resistance and the corrosion resistance of a paint film after curing are improved.
In order to solve the technical problems, the invention provides the following technical scheme:
a polyfunctional siloxane prepolymer modified acrylate emulsion consists of the following components: 100 parts by weight of methyl methacrylate, 20-70 parts by weight of butyl acrylate, 10-30 parts by weight of hydroxy acrylic ester monomer, 1-5 parts by weight of polyfunctional siloxane prepolymer, 0.5 part by weight of initiator ammonium persulfate, 1-2 parts by weight of emulsifier, 1 part by weight of pH regulator ammonia water and 200 parts by weight of deionized water;
the polyfunctional siloxane prepolymer is prepared by the following steps:
1) Preparing materials: 100 parts by weight of a silane coupling agent, 10-50 parts by weight of a double unsaturated bond functional monomer and 1 part by weight of a catalyst;
2) Adding the silane coupling agent and the double unsaturated bond functional monomer in the step 1) into a reaction kettle, heating to 60-80 ℃ under the stirring condition, and adding a catalyst to react for 0.5-2 h;
3) And (3) cooling to normal temperature after the reaction in the step (2) is finished, and discharging to obtain the polyfunctional siloxane prepolymer.
The multifunctional siloxane prepolymer modified acrylate emulsion, wherein the hydroxyl acrylate monomer is one of HEA, HPA, HEMA and HPMA.
The multifunctional siloxane prepolymer modified acrylic emulsion is characterized in that the emulsifier is one or a combination of more of sodium dodecyl benzene sulfonate, sodium dodecyl sulfate and alkyl polyoxyethylene ether.
The polyfunctional siloxane prepolymer modified acrylate emulsion is characterized in that the silane coupling agent is one or a combination of a plurality of A151, A171 and A174.
The multifunctional siloxane prepolymer modified acrylic emulsion is characterized in that the double unsaturated bond functional monomer is one or a combination of more than one of diethylene glycol diacrylate, tripropylene glycol diacrylate and hexanediol diacrylate.
The catalyst is AIBN or BPO.
The preparation method of the polyfunctional siloxane prepolymer modified acrylic emulsion comprises the following steps:
i) Mixing methyl methacrylate, butyl acrylate, hydroxy acrylate monomers and a polyfunctional siloxane prepolymer into an oil phase;
II) adding the emulsifier and the pH regulator into water to be mixed into a water phase, adding the oil phase into the water phase, and stirring to obtain a pre-emulsion;
III) adding 10% of the pre-emulsion into a reaction kettle, stirring and heating to 80 ℃, adding 10% of a catalyst, and reacting for 20min;
IV) dripping the rest 90% of pre-emulsion and the catalytic initiator into the reaction kettle at 80 ℃, carrying out heat preservation reaction for 2 hours after dripping for 2 hours, and cooling and discharging.
The technical scheme of the invention has the following beneficial technical effects:
the multi-functionality siloxane prepolymer is obtained by the reaction of a small-molecule silane coupling agent and a double unsaturated bond functional monomer under a catalyst, and has large molecular weight and functionality of more than 6. The epoxy resin can be introduced onto the main chain or side chain of acrylic ester through free radical polymerization or condensation with hydroxyl in the polymerization process, the crosslinking degree of the resin can be greatly improved by adding a small amount of the epoxy resin, and the water resistance and corrosion resistance of a cured paint film are improved by introducing a large amount of silicon into the resin structure.
Detailed Description
Example 1
In this example, a modified acrylate emulsion of a polyfunctional siloxane prepolymer consists of 100 parts by weight of methyl methacrylate, 20 parts by weight of butyl acrylate, 10 parts by weight of a hydroxyacrylate monomer, 1 part by weight of a polyfunctional siloxane prepolymer, 0.5 part by weight of initiator ammonium persulfate, 1 part by weight of emulsifier sodium dodecyl benzene sulfonate, 1 part by weight of pH regulator ammonia water and 200 parts by weight of deionized water. The specific preparation process is as follows: i) Mixing methyl methacrylate, butyl acrylate, hydroxy acrylate monomers and a polyfunctional siloxane prepolymer into an oil phase; II) adding the emulsifier and the pH regulator into water to be mixed into a water phase, adding the oil phase into the water phase, and stirring to obtain a pre-emulsion; III) adding 10% of the pre-emulsion into a reaction kettle, stirring and heating to 80 ℃, adding 10% of a catalyst, and reacting for 20min; IV) dripping the rest 90% of pre-emulsion and the catalytic initiator into the reaction kettle at 80 ℃, carrying out heat preservation reaction for 2 hours after dripping for 2 hours, and cooling and discharging.
Wherein, 100 parts by weight of silane coupling agent A151 and 10 parts by weight of di-unsaturated functional monomer diethylene glycol diacrylate are added into a reaction kettle, the temperature is raised to 60 ℃ under the condition of stirring, and 1 part by weight of catalyst AIBN is added for reaction for 2 hours; cooling to normal temperature after the reaction is finished, and discharging.
Example 2
The functional multi-functional silicone prepolymer acrylate emulsion in this example differs from example 1 in that: in this example, the amount of butyl acrylate added was changed to 50 parts by weight.
Example 3
The functional multi-functional silicone prepolymer acrylate emulsion in this example differs from example 1 in that: in this example, the amount of the hydroxy acrylate HEA added was changed to 20 parts by weight.
Example 4
The functional multi-functional silicone prepolymer acrylate emulsion in this example differs from example 1 in that: in this example, the amount of the hydroxy acrylate HEA added was changed to 30 parts by weight.
Example 5
The functional multi-functional silicone prepolymer acrylate emulsion in this example differs from example 1 in that: in this example the hydroxy acrylate monomer is changed to HPA.
Example 6
The functional multi-functional silicone prepolymer acrylate emulsion in this example differs from example 1 in that: in this example the hydroxy acrylate monomer is replaced by HEMA.
Example 7
The functional multi-functional silicone prepolymer acrylate emulsion in this example differs from example 1 in that: in this example the hydroxy acrylate monomer is instead HPMA.
Example 8
The functional multi-functional silicone prepolymer acrylate emulsion in this example differs from example 1 in that: the amount of the polyfunctional siloxane prepolymer added in this example was changed to 3 parts by weight.
Example 9
The functional multi-functional silicone prepolymer acrylate emulsion in this example differs from example 1 in that: the amount of the polyfunctional siloxane prepolymer added in this example was changed to 5 parts by weight.
Example 10
The functional multi-functional silicone prepolymer acrylate emulsion in this example differs from example 1 in that: the amount of the emulsifier added in this example was changed to 1.5 parts by weight.
Example 11
The functional multi-functional silicone prepolymer acrylate emulsion in this example differs from example 1 in that: in this example, the amount of the emulsifier added was changed to 2 parts by weight.
Example 12
The functional multi-functional silicone prepolymer acrylate emulsion in this example differs from example 1 in that: in this example, the emulsifier was changed to sodium dodecyl sulfate.
Example 13
The functional multi-functional silicone prepolymer acrylate emulsion in this example differs from example 1 in that: in this example, the emulsifier was changed to alkyl polyoxyethylene ether.
Example 14
The functional multi-functional silicone prepolymer acrylate emulsion in this example differs from example 1 in that: the silane coupling agent was changed to a171 in this example.
Example 15
The functional multi-functional silicone prepolymer acrylate emulsion in this example differs from example 1 in that: in this example, the silane coupling agent was changed to a174.
Example 16
The functional multi-functional silicone prepolymer acrylate emulsion in this example differs from example 1 in that: the silane coupling agent was changed to 50 parts by weight of a151 and 50 parts by weight of a174 in this example.
Example 17
The functional multi-functional silicone prepolymer acrylate emulsion in this example differs from example 1 in that: in this example, the amount of the double unsaturated bond functional monomer added was changed to 30 parts by weight.
Example 18
The functional multi-functional silicone prepolymer acrylate emulsion in this example differs from example 1 in that: in this example, the amount of the double unsaturated bond functional monomer added was changed to 50 parts by weight.
Example 19
The functional multi-functional silicone prepolymer acrylate emulsion in this example differs from example 1 in that: in this example, the double unsaturated bond functional monomer is changed to tripropylene glycol diacrylate.
Example 20
The functional multi-functional silicone prepolymer acrylate emulsion in this example differs from example 1 in that: in this example, the di-unsaturated bond functional monomer was changed to hexanediol diacrylate.
Example 21
The functional multi-functional silicone prepolymer acrylate emulsion in this example differs from example 1 in that: the catalyst in the preparation of the polyfunctional siloxane prepolymer in this example was changed to BPO.
Example 22
The functional multi-functional silicone prepolymer acrylate emulsion in this example differs from example 1 in that: in this example, the process during the preparation of the polyfunctional siloxane prepolymer was changed to 70℃for 1 hour.
Example 23
The functional multi-functional silicone prepolymer acrylate emulsion in this example differs from example 1 in that: in this example, the process during the preparation of the polyfunctional siloxane prepolymer was changed to 80℃for 0.5h.
The testing method comprises the following steps:
(1) The particle size of the emulsion is detected by a Markov laser particle size analyzer;
(2) Configuration of varnish: 100 parts of emulsion is added with 0.3 part of flatting agent and 0.3 part of wetting agent, and after defoaming, the emulsion is coated on tin plate by a 45-micrometer wire rod coater, and after surface drying for 30min, the emulsion is baked for 1h in a 50-DEG oven to measure other physical properties.
(3) Contact angle the varnish-coated tin plate was subjected to a water drop test by a contact angle analyzer, the adhesion was measured by a hundred-cell method, and the water resistance test was a test in which the varnish-coated tin plate was immersed in water to see the phenomenon of blushing, swelling, and even falling off in how many hours.
Table 1 comparison of emulsion properties
Sample name particle size/nm contact angle adhesion water resistance/h
Example 1 121 85 stage 1 70
Example 2 115 92 stage 1 75
Example 3 112 78 stage 0 60
Example 4 103 67 stage 0.54
Example 5 135 87 stage 1 75
Example 6 137 90 stage 0 75
Example 7 138 95 stage 0.80
Example 8 125 98 stage 0 96
Example 9 148 113 stage 0 120
Example 10 108 80 stage 1 65
Example 11 97 73 stage 1 50
Example 12 108 78 stage 1 60
Example 13 136 87 stage 1 75
Example 14 125 85 stage 1 75
Example 15 127 90 stage 1 80
Example 16 136 97 stage 0 100
Example 17 125 88 stage 0 75
Example 18 140 95 stage 0.90
Example 19 127 89 stage 0.85
Example 20 138 96 stage 0.95
Example 21 117 77 stage 1 60
Example 22 132 96 stage 0.84
Example 23 145 103 stage 0 105
As is clear from the data in table 1, the addition amount of the polyfunctional siloxane prepolymer was increased, and the contact angle, adhesion and water resistance of the polyfunctional siloxane prepolymer-modified acrylate emulsion were all improved.
It is apparent that the above examples are given by way of illustration only and are not limiting of the embodiments. Other variations or modifications of the above teachings will be apparent to those of ordinary skill in the art. It is not necessary here nor is it exhaustive of all embodiments. While the obvious variations or modifications which are extended therefrom remain within the scope of the claims of this patent application.

Claims (5)

1. The multifunctional siloxane prepolymer modified acrylate emulsion is characterized by comprising the following components: 100 parts by weight of methyl methacrylate, 20-70 parts by weight of butyl acrylate, 10-30 parts by weight of hydroxy acrylic ester monomer, 1-5 parts by weight of polyfunctional siloxane prepolymer, 0.5 part by weight of initiator ammonium persulfate, 1-2 parts by weight of emulsifier, 1 part by weight of pH regulator ammonia water and 200 parts by weight of deionized water;
the polyfunctional siloxane prepolymer is prepared by the following steps:
1) Preparing materials: 100 parts by weight of a silane coupling agent, 10-50 parts by weight of a double unsaturated bond functional monomer and 1 part by weight of a catalyst; wherein the silane coupling agent is one or more of A151, A171 and A174, and the double unsaturated bond functional monomer is one or more of diethylene glycol diacrylate, tripropylene glycol diacrylate and hexanediol diacrylate;
2) Adding the silane coupling agent and the double unsaturated bond functional monomer in the step 1) into a reaction kettle, heating to 60-80 ℃ under the stirring condition, and adding a catalyst to react for 0.5-2 h;
3) And (3) cooling to normal temperature after the reaction in the step (2) is finished, and discharging to obtain the polyfunctional siloxane prepolymer.
2. The multi-functional silicone prepolymer modified acrylate emulsion according to claim 1 wherein the hydroxy acrylate monomer is one of HEA, HPA, HEMA and HPMA.
3. The multi-functionality silicone prepolymer modified acrylate emulsion according to claim 1 wherein the emulsifier is a combination of one or more of sodium dodecylbenzene sulfonate, sodium dodecylsulfate and alkyl polyoxyethylene ether.
4. The multi-functional silicone prepolymer modified acrylate emulsion according to claim 1 wherein the catalyst is AIBN or BPO.
5. The method for preparing the multi-functional siloxane prepolymer modified acrylate emulsion according to any one of claims 1 to 4, comprising the following steps:
i) Mixing methyl methacrylate, butyl acrylate, hydroxy acrylate monomers and a polyfunctional siloxane prepolymer into an oil phase;
II) adding the emulsifier and the pH regulator into water to be mixed into a water phase, adding the oil phase into the water phase, and stirring to obtain a pre-emulsion;
III) adding 10% of the pre-emulsion into a reaction kettle, stirring and heating to 80 ℃, adding 10% of an initiator, and reacting for 20min;
IV) dripping the rest 90% of pre-emulsion and the initiator into the reaction kettle at 80 ℃, carrying out heat preservation reaction for 2 hours after dripping for 2 hours, and cooling and discharging.
CN202210811464.5A 2022-07-11 2022-07-11 Functional polyfunctional siloxane prepolymer acrylate emulsion and preparation method thereof Active CN114989362B (en)

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101649153A (en) * 2009-09-07 2010-02-17 大连工业大学 Organic silicon modified acrylic ester aqueous wood lacquer latex and synthesizing method thereof
CN102898578A (en) * 2012-07-16 2013-01-30 杭州师范大学 Self-crosslinking silicone-acrylate copolymer emulsion and preparation method
CN102977253A (en) * 2012-11-06 2013-03-20 中科院广州化学有限公司 Silicone modified acrylate hybrid emulsion and preparation method and application thereof
CN103626933A (en) * 2013-10-14 2014-03-12 杭州师范大学 Polysilsesquioxane-polyacrylate-nano SiO2 composite emulsion and preparation method and application thereof
CN109762095A (en) * 2019-01-24 2019-05-17 广州秀珀化工涂料有限公司 Organic-silicon-modified hydroxy acrylate lotion and preparation method thereof

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101649153A (en) * 2009-09-07 2010-02-17 大连工业大学 Organic silicon modified acrylic ester aqueous wood lacquer latex and synthesizing method thereof
CN102898578A (en) * 2012-07-16 2013-01-30 杭州师范大学 Self-crosslinking silicone-acrylate copolymer emulsion and preparation method
CN102977253A (en) * 2012-11-06 2013-03-20 中科院广州化学有限公司 Silicone modified acrylate hybrid emulsion and preparation method and application thereof
CN103626933A (en) * 2013-10-14 2014-03-12 杭州师范大学 Polysilsesquioxane-polyacrylate-nano SiO2 composite emulsion and preparation method and application thereof
CN109762095A (en) * 2019-01-24 2019-05-17 广州秀珀化工涂料有限公司 Organic-silicon-modified hydroxy acrylate lotion and preparation method thereof

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Denomination of invention: A functional multifunctional siloxane prepolymer acrylate lotion and its preparation method

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