CN113929812A - Acrylate thermal polymerization resin and preparation method thereof - Google Patents
Acrylate thermal polymerization resin and preparation method thereof Download PDFInfo
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- CN113929812A CN113929812A CN202111296140.4A CN202111296140A CN113929812A CN 113929812 A CN113929812 A CN 113929812A CN 202111296140 A CN202111296140 A CN 202111296140A CN 113929812 A CN113929812 A CN 113929812A
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- acrylate
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- polymerization resin
- initiator
- peroxide
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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
- 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
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/04—Homopolymers or copolymers of esters
- C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09J133/062—Copolymers with monomers not covered by C09J133/06
- C09J133/064—Copolymers with monomers not covered by C09J133/06 containing anhydride, COOH or COOM groups, with M being metal or onium-cation
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/04—Homopolymers or copolymers of esters
- C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09J133/062—Copolymers with monomers not covered by C09J133/06
- C09J133/066—Copolymers with monomers not covered by C09J133/06 containing -OH groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J7/00—Adhesives in the form of films or foils
- C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
- C09J7/38—Pressure-sensitive adhesives [PSA]
- C09J7/381—Pressure-sensitive adhesives [PSA] based on macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- C09J7/385—Acrylic polymers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J2301/00—Additional features of adhesives in the form of films or foils
- C09J2301/30—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier
- C09J2301/302—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier the adhesive being pressure-sensitive, i.e. tacky at temperatures inferior to 30°C
Abstract
The invention discloses an acrylate thermal polymerization resin and a preparation method thereof. A preparation method of acrylate thermal polymerization resin comprises the following steps: putting an acrylate monomer into a reaction vessel, adding a thermal initiator in an inert gas atmosphere, heating to 110-150 ℃, reacting for 4-5 hours to obtain an acrylate polymer, and adding hydroxypropyl acrylate or isooctyl acrylate to adjust the viscosity of the system to obtain the acrylate thermal polymerization resin. The acrylate thermal polymerization resin provided by the invention has strong viscosity, good adhesive force and a solvent-free process, can solve the solvent problem of the existing solvent-based pressure-sensitive adhesive synthesis, and can fill the vacancy of the low-TG point solvent-free pressure-sensitive adhesive in the market.
Description
Technical Field
The invention belongs to the technical field of pressure-sensitive adhesives, and particularly relates to an acrylate thermal polymerization resin and a preparation method thereof.
Background
Pressure-sensitive adhesives, which are one type of adhesive that is pressure-sensitive, are tightly bonded to an adherend by application of a certain pressure, and are often processed into adhesive tapes, labels, or various sheet-like products for application. The solvent type acrylate pressure-sensitive adhesive is widely applied to pressure-sensitive labels, packaging tapes, double-sided tapes and the like because of the advantages of strong adhesive force, high drying speed, water resistance, cold resistance, high temperature resistance, high humidity resistance and the like, but the solvent of the solvent type acrylate is mainly ethyl acetate and toluene, and the solvents are toxic and flammable and can pollute the environment. In addition, the acrylate monomer is also polymerized in an emulsion polymerization mode, wherein the emulsion polymerization takes water as a solvent, the monomer is dispersed into emulsion in water under the action of an emulsifier and by means of mechanical stirring, the polymerization reaction initiated by an initiator is partially used in an emulsion form, and partially needs complicated processes of coagulation, separation, washing and the like, is prepared into proper solid resin, and can be used after being melted by proper monomers. The emulsifier used in the method also has influence on the performance of the resin, and has the disadvantages of long process, high energy consumption and much danger. The solvent-free polyacrylate products sold on the market at present are high-TG solid granular acrylic acid, and are not sold by low-TG solvent-free synthesis process polyacrylate.
Disclosure of Invention
Aiming at the problems in the prior art, the invention aims to provide the acrylic acid thermal polymerization resin and the preparation method thereof, and the ultraviolet light curing polyacrylic acid pressure-sensitive adhesive prepared by the preparation method provided by the invention has the characteristics of pure product, complex separation, purification and reprocessing, simple operation compared with other processes, low cost, high utilization rate of production equipment, high performance, strong viscosity, good adhesive force, solvent-free process, environmental friendliness and strong market competitiveness.
The technical scheme adopted by the invention is as follows: a preparation method of acrylate thermal polymerization resin comprises the following steps: putting an acrylate monomer into a reaction vessel, adding a thermal initiator in an inert gas atmosphere, heating to 110-150 ℃, reacting for 4-5 hours to obtain an acrylate polymer, and adding hydroxypropyl acrylate or isooctyl acrylate to adjust the viscosity of the system to obtain the acrylate thermal polymerization resin.
Preferably, the acrylate monomer is selected from at least one of n-butyl acrylate, n-butyl methacrylate, isooctyl acrylate, acrylic acid, hydroxyethyl acrylate, hydroxyethyl methacrylate, hydroxypropyl acrylate, hydroxypropyl methacrylate, hydroxybutyl acrylate, isobornyl methacrylate and ethylene glycol dimethacrylate.
Preferably, the thermal initiator is selected from more than one of benzoyl peroxide, benzoyl tert-butyl peroxide, methyl ethyl ketone peroxide, stearyl peroxide, lauroyl peroxide and 3,5, 5-trimethylhexanoyl peroxide.
Preferably, the hydroxypropyl acrylate or isooctyl acrylate for dilution accounts for 20-30% of the total weight, based on the sum of the mass of the acrylate monomer, the thermal initiator, the hydroxypropyl acrylate or isooctyl acrylate.
Preferably, the mass of the thermal initiator accounts for 0.02-0.03% of the mass of the acrylate monomer.
Preferably, the specific steps of heating to 110-150 ℃ and reacting for 4-5 hours are as follows: heating to 110 deg.c for 2-3 hr, and gradually heating to 150 deg.c for 2-2.5 hr.
The invention also provides the acrylate thermal polymerization resin prepared by the preparation method of the acrylate thermal polymerization resin.
An ultraviolet light curing polyacrylic acid pressure sensitive adhesive comprises the acrylic ester thermal polymerization resin. The TG (glass transition temperature) of the ultraviolet curing polyacrylic acid pressure-sensitive adhesive is-40 ℃ to-20 ℃.
Preferably, the ultraviolet curing polyacrylic acid pressure-sensitive adhesive specifically comprises the following components in parts by mass: 100 parts of acrylic ester thermal polymerization resin, 1 part of initiator TPO and 1841.5 parts of initiator.
Compared with the prior art, the invention has the advantages that:
1. the acrylate thermopolymerization resin provided by the invention has strong viscosity, good adhesive force and a solvent-free process, can solve the solvent problem of the synthesis of the existing solvent-based pressure-sensitive adhesive, and can fill the vacancy of the low-TG point solvent-free pressure-sensitive adhesive in the market, the TG point of the pressure-sensitive adhesive provided by the invention is between 40 ℃ below zero and 20 ℃ below zero, and the TG point of the solvent-free pressure-sensitive adhesive sold in the market at present is between 40 ℃ below zero and 100 ℃.
2. The preparation method of the thermal polymerization of the acrylic ester provided by the invention has short reaction time, is a rapid production technology for synthesizing the pressure-sensitive adhesive with low cost and high performance, and can be used for industrial mass production.
Detailed Description
The following examples are further illustrative of the present invention and are not intended to be limiting thereof. Unless otherwise specified, the reagents proposed in the present invention are all commercially available. In the following examples, the mass fraction of each reactant is represented by the sum of the mass of the reactants being 100%.
Example 1
Putting 10% of acrylic acid, 30% of isooctyl acrylate and 29.985% of n-butyl acrylate monomer into a reaction container, introducing nitrogen for 2 hours, adding 0.015% of thermal initiator benzoyl peroxide, continuously heating to 100 ℃ in a nitrogen environment for 2 hours of pre-initiation, gradually heating to 150 ℃ for 2 hours of reaction to obtain acrylic acid (ester) polymer, and finally adding 30% of isooctyl acrylate monomer to adjust the viscosity of the system to be between 40000 and 60000cps/60 ℃ to obtain the acrylic acid ester thermal polymerization resin.
Example 2
Putting 15% of acrylic acid, 35% of isooctyl acrylate and 21.98% of n-butyl methacrylate monomer into a reaction vessel, introducing nitrogen for 2 hours, adding a thermal initiator of methyl ethyl ketone peroxide to 0.02%, continuously heating to 100 ℃ in a nitrogen environment for pre-initiation for 3 hours, gradually heating to 150 ℃ for reaction for 2 hours to obtain an acrylic acid (ester) polymer, and finally adding 28% of isooctyl acrylate monomer to adjust the viscosity to be 40000-60000cps/60 ℃ to obtain the acrylic acid ester thermal polymerization resin.
Example 3
5 percent of acrylic acid, 30 percent of isooctyl acrylate, 15 percent of isobornyl acrylate and 24.98 percent of n-butyl acrylate monomer are put into a reaction vessel, after 2 hours of nitrogen gas introduction, 0.02 percent of thermal initiator benzoyl peroxide is added, the mixture is continuously heated to 100 ℃ in the nitrogen environment for 3 hours of pre-initiation, then the temperature is gradually increased to 150 ℃ for 2 hours of reaction to obtain acrylic acid (ester) polymer, and finally 25 percent of hydroxybutyl acrylate monomer is added to adjust the viscosity to be between 30000-60000cps/60 ℃ to obtain the acrylic acid ester thermal polymerization resin.
Example 4
Putting 8% of acrylic acid, 1% of ethylene glycol dimethacrylate, 6% of hydroxypropyl acrylate, 39% of isooctyl acrylate and 25.97% of n-butyl acrylate monomer into a reaction container, introducing nitrogen for 2 hours, adding 0.03% of benzoyl peroxide tert-butyl as a thermal initiator, continuously heating to 100 ℃ in a nitrogen environment for 2 hours for pre-initiation, gradually heating to 150 ℃ for reaction for 2.5 hours to obtain acrylic acid (ester) polymer, and finally adding 20% of isooctyl acrylate monomer to adjust the viscosity to be 40000-50000cps/60 ℃ to obtain the acrylic acid ester thermal polymerization resin.
Comparative example 1
The proportion is expressed by the mass fraction of each reactant, wherein the sum of the mass of each reactant is 100%.
Putting 40% deionized water, 2% emulsifier OP-10 and 0.35% catalyst ammonium persulfate into a reaction kettle, introducing nitrogen, heating to 75 ℃ and stirring for 10 minutes to uniformly dissolve all substances, then adding 2% acrylic acid, 48% butyl acrylate and 48% methacrylic acid, stirring and emulsifying for 15 minutes to obtain pre-emulsion, transferring the pre-emulsion into a constant-pressure settling funnel, adjusting the temperature of the reaction kettle to 50 ℃, adding 0.5% emulsifier OP-10 and 8% deionized water, stirring uniformly, gradually and slowly adding the pre-emulsion into the reaction kettle by using the constant-pressure settling funnel, gradually heating to 75 ℃ and keeping the temperature stable, then adding 0.006% catalyst ammonium persulfate every 5 minutes, keeping the temperature for 3 hours after totally adding 24 times, feeding the emulsion after reaction homogenization into a flocculation reaction kettle through a slurry pump for flocculation, feeding the coagulated material into a material dehydration device for dehydration, and (3) the dehydrated material enters a boiling granulation fluidized bed for granulation through a material conveying device, and solid acrylate polymerization particles are obtained after granulation is finished.
Testing the performance of the pressure-sensitive adhesive resin:
100g of the resins obtained in examples 1 to 4 above were taken and added with 1g of initiator TPO and 1.5g of initiator 184, respectively, and after uniform dispersion, the following two curing methods were used: 1. aerobic curing: after curing by an RW-UVA201-20X type UV machine, 2, anaerobic curing: resin with the thickness of 100um is coated on a PET film, the PET film is covered with a release film, a 395nm LED lamp box is used for curing, and after curing, a KJ-1065 peeling force tester is used for testing the peeling force.
Heating 30g of isooctyl acrylate to 90 ℃, adding 70g of the solid acrylate polymer particles prepared in the comparative example 1, melting uniformly to obtain pressure-sensitive adhesive resin, adding 1g of initiator TPO and 1.5g of initiator 184, dispersing uniformly, and then curing in the following two ways: 1. aerobic curing: after curing by an RW-UVA201-20X type UV machine, 2, anaerobic curing: coating resin with the thickness of 100um on a PET film, coating the PET film with a release film, curing the PET film by using a 395nm LED lamp box, and testing the peel force of the cured PET film by using a KJ-1065 peel force tester:
the recorded data are shown in Table 1:
TABLE 1
| Example 1 | Example 2 | Example 3 | Example 4 | Comparative example 1 | |
| Peel force (aerobic curing) | 1400N | 1500N | 1500N | 1600N | 1300N |
| Peel force (oxygen free curing) | 1300N | 1300N | 1400N | 1500N | 1200N |
| Initial adhesion | 10 ball | 11 ball | 10 ball | 12 ball | 10 ball |
As can be seen from Table 1, the pressure-sensitive adhesive product prepared from the acrylate thermal polymerization resin has the advantages of solvent-free process, strong viscosity and good adhesive force. Comparative example 1 is that solid acrylic acid produced by emulsion polymerization process has high TG point, and when it is used as pressure sensitive adhesive resin, it needs to be dissolved again, and its process is complex, and it produces many dangerous wastes and its energy consumption is high. The pressure-sensitive adhesive finished product prepared from the acrylate thermopolymer has excellent performance, greatly improves the process, fills the gap of the low-TG solvent-free pressure-sensitive adhesive in the existing market, and has obvious market competitiveness.
The above is only a preferred embodiment of the present invention, and it should be noted that the above preferred embodiment should not be considered as limiting the present invention, and the protection scope of the present invention should be subject to the scope defined by the claims. It will be apparent to those skilled in the art that various modifications and adaptations can be made without departing from the spirit and scope of the invention, and these modifications and adaptations should be considered within the scope of the invention.
Claims (9)
1. The preparation method of the acrylate thermal polymerization resin is characterized by comprising the following steps: putting an acrylate monomer into a reaction vessel, adding a thermal initiator in an inert gas atmosphere, heating to 110-150 ℃, reacting for 4-5 hours to obtain an acrylate polymer, and adding hydroxypropyl acrylate or isooctyl acrylate to adjust the viscosity of the system to obtain the acrylate thermal polymerization resin.
2. The method of claim 1, wherein the acrylate monomer is at least one selected from the group consisting of n-butyl acrylate, n-butyl methacrylate, isooctyl acrylate, acrylic acid, hydroxyethyl acrylate, hydroxyethyl methacrylate, hydroxypropyl acrylate, hydroxypropyl methacrylate, hydroxybutyl acrylate, isobornyl methacrylate, and ethylene glycol dimethacrylate.
3. The method of claim 1, wherein the thermal initiator is selected from one or more of benzoyl peroxide, benzoyl tert-butyl peroxide, methyl ethyl ketone peroxide, stearyl peroxide, lauroyl peroxide, and 3,5, 5-trimethylhexanoyl peroxide.
4. The method for preparing the thermal acrylate polymerization resin according to claim 1, wherein the hydroxypropyl acrylate or isooctyl acrylate accounts for 20-30% of the total weight of the thermal acrylate polymerization resin, based on the total weight of the acrylate monomer, the thermal initiator and the hydroxypropyl acrylate or isooctyl acrylate.
5. The method for preparing the thermal acrylate polymerization resin as claimed in claim 4, wherein the thermal initiator accounts for 0.02-0.03% of the acrylate monomer by mass.
6. The method for preparing the thermal acrylate polymerization resin according to claim 1, wherein the heating to 110-150 ℃ for 4-5 hours comprises the following steps: heating to 110 deg.c for 2-3 hr, and gradually heating to 150 deg.c for 2-2.5 hr.
7. The thermal acrylate polymer resin prepared by the method of claim 1.
8. An ultraviolet-curable polyacrylic acid pressure-sensitive adhesive comprising the thermal acrylate polymerization resin according to claim 7.
9. The ultraviolet curing polyacrylic acid pressure sensitive adhesive according to claim 8, specifically comprising the following components in parts by mass: 100 parts of acrylic ester thermal polymerization resin, 1 part of initiator TPO and 1841.5 parts of initiator.
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| Application Number | Priority Date | Filing Date | Title |
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| CN202111296140.4A CN113929812A (en) | 2021-11-03 | 2021-11-03 | Acrylate thermal polymerization resin and preparation method thereof |
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| CN202111296140.4A CN113929812A (en) | 2021-11-03 | 2021-11-03 | Acrylate thermal polymerization resin and preparation method thereof |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN115717042A (en) * | 2022-11-30 | 2023-02-28 | 宁波大榭开发区综研化学有限公司 | Acrylate adhesive, preparation method thereof, acrylate pressure-sensitive adhesive tape and preparation method thereof |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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