WO2023177038A1 - Procédé de préparation d'adhésif à l'aide d'une émission à faible teneur en carbone, et procédé de fabrication d'un ruban adhésif fabriqué à l'aide de celui-ci - Google Patents

Procédé de préparation d'adhésif à l'aide d'une émission à faible teneur en carbone, et procédé de fabrication d'un ruban adhésif fabriqué à l'aide de celui-ci Download PDF

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Publication number
WO2023177038A1
WO2023177038A1 PCT/KR2022/016984 KR2022016984W WO2023177038A1 WO 2023177038 A1 WO2023177038 A1 WO 2023177038A1 KR 2022016984 W KR2022016984 W KR 2022016984W WO 2023177038 A1 WO2023177038 A1 WO 2023177038A1
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adhesive
manufacturing
low
reaction
solvent
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PCT/KR2022/016984
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English (en)
Korean (ko)
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박서규
고세윤
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주식회사 켐코
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Publication of WO2023177038A1 publication Critical patent/WO2023177038A1/fr

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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
    • 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
    • C09J133/08—Homopolymers or copolymers of acrylic acid esters
    • 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
    • C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
    • C09J4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00
    • 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]

Definitions

  • the present invention relates to a method for manufacturing an adhesive using a low-carbon emission process and a method for manufacturing an adhesive tape manufactured using the same. More specifically, to manufacture an adhesive with excellent adhesion while applying an improved manufacturing process that can reduce carbon emissions. It relates to a manufacturing method that can be made and a method of manufacturing an adhesive tape using the adhesive.
  • adhesives are used to manufacture adhesive sheets or adhesive films that can be attached and detached to adherends, and are generally manufactured by mixing ingredients including monomers, solvents, polymerization initiators, curing agents, and additives. At this time, sufficient equipment operation time and energy consumption for heating are required to meet the required physical properties of the adhesive, and this production activity itself is a cause of carbon emissions.
  • the present invention was developed in consideration of the above-described prior art, and its purpose is to provide a method for manufacturing an adhesive using an improved process that significantly reduces carbon emissions compared to existing processes.
  • the method of manufacturing an adhesive using the low-carbon emission process of the present invention to solve the above problems is a method of producing an adhesive containing an adhesive resin, a polymerization initiator, a low boiling point solvent, and a curing agent, wherein the adhesive resin is a mixture of a hydrophilic monomer and a solvent. It is characterized in that it is manufactured by including a first step of producing a colloidal polymer and a second step of producing a sticky polymer by mixing a hydrophobic monomer with the colloidal polymer.
  • the low boiling point solvent preferably has a boiling point of 80°C or lower.
  • the adhesive preferably has a non-volatile matter (NVM) content of 50% by weight or more and a viscosity of 20 to 200 kcps.
  • NVM non-volatile matter
  • an adhesive tape can be manufactured including a process of coating a substrate with the adhesive produced using the adhesive manufacturing method of the present invention.
  • the method for manufacturing an adhesive according to the present invention shows the effect of applying a low-carbon emission process by applying an improved process that significantly reduces carbon emissions compared to existing processes.
  • a high concentration of adhesive can be produced through a low-carbon emission process, which has the effect of increasing production efficiency.
  • 1 is a conceptual diagram showing a process for manufacturing the adhesive resin of the present invention.
  • Figure 2 shows the results of observing the change in turbidity over the course of the reaction.
  • Figure 3 shows the results of measuring the viscosity change at each reaction step in Synthesis Examples 1 to 6.
  • the present invention relates to a method of manufacturing an adhesive using a low-carbon emission process.
  • a low-carbon emission process must meet the following conditions from both a technical and economic perspective.
  • the productivity of the production utility must be increased by increasing the concentration of the adhesive. In other words, it must be possible to increase efficiency relative to operating time. To achieve this, the volatilization time of the solvent used in the production of the adhesive must be reduced and the amount of volatile solvent must be reduced. For this purpose, a low boiling point solvent must be used and a suitable process must be developed. Additionally, energy consumption must be reduced by lowering the overall construction temperature of production utilities. Despite these improvements in process conditions, the physical properties of the adhesive should not deteriorate.
  • the present invention relates to a method of manufacturing an adhesive by applying an improved process to meet the conditions of such a low-carbon emission process.
  • the first step of producing a colloidal polymer by mixing a hydrophilic monomer and a solvent in the process of producing the adhesive resin is to apply a process that includes a second step of producing a functional polymer that develops adhesiveness by mixing a hydrophobic monomer with a colloidal polymer.
  • hydrophilic monomers are dispersed in a solvent as a colloid-forming material ( Figure 1a).
  • Figure 1b a colloid-forming material and hydrophobic monomers for developing adhesiveness are mixed together.
  • Figure 1c micelles are formed by hydrophilic monomers, and as the molecular weight of the hydrophobic monomer increases, the hydrophobic monomer permeates into the micelle due to the difference in solubility.
  • polymerization (oligomerization) of the monomers present inside the micelle progresses to form an adhesive-generating functional polymer ( Figure 1d), making it possible to obtain the adhesive resin desired in the present invention. do.
  • the polymer mentioned in the manufacturing process of the present invention should be understood as an oligomer-like form in which the monomer has a high molecular weight rather than a typical polymer resin.
  • solubility decreases as the polymer is converted from a monomer to an oligomer.
  • dispersibility is improved due to the repulsion between micelles, so solubility can be maintained even in the polymerized state. There will be.
  • the adhesive is manufactured by mixing monomers, polymerization initiators, solvents, curing agents, and other additives that make up the adhesive.
  • an adhesive resin is formed by polymerization of monomers.
  • a high-concentration adhesive can be manufactured with a non-volatile matter (NVM) content of 50% by weight or more, and the viscosity is 20 to 200 kcps, which has the advantage in the process of maintaining a low viscosity. do.
  • NVM non-volatile matter
  • the present invention uses a low boiling point solvent and goes through a separate process of manufacturing the adhesive resin to maintain the viscosity appropriately.
  • the process for producing the adhesive resin includes a first step of reacting a hydrophilic monomer and a solvent to produce a colloid, and a second step of adding a hydrophobic monomer to the colloid to form a protective layer.
  • a colloid is prepared by reacting hydrophilic monomers dispersed in a solvent. Through this, a dispersion medium for granulated polymers is obtained.
  • it is advantageous to increase the crosslinking rate of the hydrophilic monomer so itaconic acid, hydroxypropyl acrylate, and hydroxybutyl acrylate are used as the hydrophilic monomer. It is preferable to use any one of the following monomers: hydroxyethyl acrylate, 1,6-hexanediol diacrylate, and trimethylolpropane triacylate. . Additionally, maleic anhydride may be added to increase the crosslinking rate and prevent blocking. Therefore, in the first step, the dispersion medium of the monomer is crosslinked and polymerized to form a colloidal phase.
  • a hydrophobic monomer When a hydrophobic monomer is added to the colloid dispersed in a solvent, a protective layer is formed on the surface of the colloid. Through this, a non-aqueous dispersion (NAD) polymer phase is formed.
  • NAD non-aqueous dispersion
  • the volatilization rate of the solvent can be increased, the physical properties of the adhesive can be easily controlled, and a high concentration polymer that is environmentally resistant and eco-friendly can be synthesized, thereby increasing the efficiency of the adhesive manufacturing process.
  • hydrophobic monomers for forming the adhesive development functional polymer monomers such as butylacrylate (BA), butylmelamine, 2-ethylhexyl acrylate (2-EHA), divinyl acrylate, and trivinyl acrylate can be used. there is.
  • An adhesive can be manufactured by mixing a polymerization initiator, a low boiling point solvent, and a curing agent with the adhesive resin obtained through the above manufacturing process. Additionally, in the process of manufacturing the adhesive, unreacted products can be reduced by additionally adding a catalyst as needed.
  • the adhesive manufacturing process is completed by terminating the reaction by adding a solvent, a diluent, when an adhesive of the target molecular weight is produced. Unlike the existing process in which raw materials are added all at once, when the reaction is carried out through sequential addition, the reaction time is longer, but it is easier to control the physical properties by controlling the molecular weight, and the stability of the product is also improved because the reaction proceeds sequentially. It represents an increasing advantage.
  • NVM non-volatile matter
  • the production speed was only 10 to 18 m/min, but the production speed of the present invention was only 10 to 18 m/min.
  • the production speed was 25 to 35 m/min, dramatically increasing production efficiency.
  • the adhesive manufacturing method of the present invention uses a low boiling point solvent.
  • low boiling point solvents include acetone (boiling point 56°C), methanol (boiling point 65°C), and ethanol (boiling point 78).
  • the solvents are mixed in an appropriate ratio. It is preferable to use it by mixing.
  • drying furnace temperature existing process Process of the present invention 1st stage (°C) 100 60 2nd stage (°C) 120 80 3rd stage (°C) 140 100 4th stage (°C) 110 80 5 steps (°C) 90 60
  • test operation results showed that applying the process of the present invention can lower the overall drying temperature of the drying furnace by 30 to 40°C compared to the existing process. These results serve as a factor in reducing carbon emissions by reducing the process temperature.
  • Viscosity of existing process Viscosity (kcps) of the process of the present invention 25 >1,000 - 30 700 ⁇ 1,000 - 35 400 ⁇ 600 - 40 300 - 50 - 100 ⁇ 200 55 - 50 ⁇ 100 60 - 25 ⁇ 10
  • the adhesive manufacturing method of the present invention can increase production efficiency by reducing utility operation time compared to existing processes, increase production speed by reducing the content of volatile solvents and using low boiling point solvents, and increase the content of NVM. It can be seen that it is a highly efficient process that can reduce carbon emissions because the viscosity range can be adjusted to increase production efficiency without reducing production efficiency.
  • an adhesive tape can be manufactured including the process of applying the adhesive produced using the above adhesive manufacturing method to a substrate and curing it to form an adhesive layer.
  • the substrate is a substrate for manufacturing a tape and may be made of a material selected from polyethylene terephthalate (PET), polyethylene (PE), polypropylene (PP), polyurethane (PU), polycarbonate (PC), or polyimide (PI).
  • PET is a rigid material that can act as a buffer through shock absorption, making it more suitable for application as a tape.
  • the method of applying the adhesive to the substrate can be used in conventional tape manufacturing such as the bar coat method, reverse roll coat method, knife coat method, roll knife coat method, gravure coat method, doctor blade coat method, and slot die coat method. Any method used can be used.
  • composition A was prepared by adding 110 g of vinyl acetate monomer, 15 g of acrylic acid, and 180 g of ethyl alcohol to the reaction device, and 0.5 g of Azobisisobutyronitrile (AIBN) was added to the composition A as a polymerization initiator. The reaction was initiated by raising the temperature to 80°C, and the maintenance reaction was carried out for 30 minutes.
  • AIBN Azobisisobutyronitrile
  • composition B 15 g of acrylic acid monomer, 336 g of 2-Ethyl hexyl acrylate monomer, 144 g of n-butyl acrylate monomer, and ethyl alcohol Composition B was prepared by mixing 120 g of alcohol), the composition B was placed in a dropping tank, and 0.5 g of AIBN (Azobisisobutyronitrile) as a polymerization initiator was mixed thereto and added dropwise for 90 minutes. After the dropwise addition, a maintenance reaction was carried out for 60 minutes, and then composition C prepared by mixing 60g of ethyl acetate and 0.5g of the polymerization initiator AIBN was added dropwise for 30 minutes until the reaction was completed. After cooling, 50 g of ethyl acetate was added to terminate the reaction. The viscosity of the adhesive resin (A) obtained after completion of the reaction was 6,000 cPs, and the non-volatile content was 60%.
  • AIBN Azobisisobutyronit
  • composition A 110 g of vinyl acetate monomer, 10 g of acrylic acid monomer, 180 g of ethyl alcohol, 0.5 g of Azobisisobutyronitrile (AIBN), composition B;
  • Adhesive resin (B) was obtained in the same manner except that 10g of acrylic acid monomer, 336g of 2-ethylhexyl acrylate monomer, 144g of n-butylacrylate monomer, 120g of ethyl alcohol, and 0.5g of AIBN (Azobisisobutyronitrile) were used.
  • the viscosity of the adhesive resin (B) was 5,000 cPs, and the non-volatile content was 60%.
  • the same reaction device as Synthesis Example 1 was prepared, and 620 g of an acrylic mixture consisting of 110 g of vinyl acetate monomer, 30 g of acrylic acid monomer, 336 g of 2-ethylhexyl acrylate monomer, and 144 g of n-buty acrylate monomer was prepared, and 30% of the prepared acrylic mixture was added.
  • 0.5 g of polymerization initiator (AIBN) and solvent (380 g of ethyl acetate, 50 g of toluene) were added to the reactor and heated to 80°C to initiate the reaction. A maintenance reaction was carried out for 30 minutes, and then 70% of the acrylic mixture was added to the reactor.
  • AIBN polymerization initiator
  • solvent 380 g of ethyl acetate, 50 g of toluene
  • the viscosity of the adhesive resin (D) was 5,000 ⁇ 1,000 cPs, and the non-volatile content was 60%.
  • the reaction was carried out in the same manner as in Synthesis Example 3, the amount of acrylic monomer was the same, and the amount of solvent (ethyl acetate) was reduced by 500 g to obtain an adhesive resin with 60% non-volatile content. However, due to gelation of the monomers in the middle of the reaction, the final result was was not obtained and the reaction was terminated.
  • the reaction was performed in the same manner as Synthesis Example 3, the amount of acrylic monomer was the same, and the amount of solvent (ethyl acetate) was reduced by 320 g to obtain an adhesive resin with 50% non-volatile content. However, due to gelation of the monomers in the middle of the reaction, the final The reaction was terminated without obtaining any results.
  • composition ratios for the colloidal polymer formation step and the adhesive function-expressing polymer formation step in Synthesis Examples 1 to 6 are shown in Table 3.
  • the unit is g.
  • Synthesis Example 1 Synthesis Example 2 Synthesis Example 3 Synthesis Example 5 Synthesis Example 6 vinyl acetate 110 110 110 110 110 acrylic acid 30 20 30 30 30 30 2-ethylhexyl acrylate 336 336 336 336 n-butylacrylate 144 144 144 144 ethyl alcohol 300 300 Ethyl acetate 100 110 850 350 530 toluene 50 50 50 Solid content (%) 60 60 40 - - Viscosity (cPs) 6,000 5,000 5,000 - -
  • the adhesive layer was manufactured to have a thickness of 25 ⁇ m, 50 ⁇ m PET release paper was used, and 25 ⁇ m PET was used as the carrier. After applying the adhesive layer, a drying process was performed at 110°C for 90 seconds for No. 4 in Preparation Example 1, and a drying process was performed at 110°C for 120 seconds for No. 6 in Preparation Examples 5. Afterwards, the aging process was performed at 60°C for 48 hours.
  • the physical properties of the adhesive tape were measured as follows. Adhesion was measured using UTM equipment according to KS T 1028.
  • a 25 mm wide tape was pressed to a SUS304 adherend using a rubber roller (2.0 kg load) and left at room temperature for 30 minutes, and the 180° Peel value was measured at a speed of 300 mm/min.
  • Heat resistance was measured by increasing the temperature at a rate of 10°C/10 minutes and then measuring the desorption temperature. After producing a sample of 25 Afterwards, a 500g load was applied to raise the temperature from 50°C to 10°C per 10 minutes, and the temperature during desorption was recorded.
  • Example 1 Example 2 Example 3 Example 4 Comparative Example 1 Comparative Example 2 Comparative Example 3 Room temperature adhesion (gf/25mm) 2,228 2,585 2,053 2,274 2,029 2,348 1,246 Heat resistance (°C) 150 or more 150 or more 150 or more 140 150 or more 100

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Chemical Kinetics & Catalysis (AREA)

Abstract

La présente invention concerne un procédé de préparation d'un adhésif à l'aide d'une émission à faible teneur en carbone, l'adhésif comprenant une résine adhésive, un initiateur de polymérisation, un solvant à bas point d'ébullition et un agent de durcissement, et la résine adhésive étant préparée par : une première étape consistant à mélanger un monomère hydrophile et un solvant, ce qui permet de préparer un polymère colloïdal; et une seconde étape consistant à mélanger le polymère colloïdal et un monomère hydrophobe, ce qui permet de préparer un polymère ayant un pouvoir adhésif.
PCT/KR2022/016984 2022-03-17 2022-11-02 Procédé de préparation d'adhésif à l'aide d'une émission à faible teneur en carbone, et procédé de fabrication d'un ruban adhésif fabriqué à l'aide de celui-ci WO2023177038A1 (fr)

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KR1020220033134A KR102423152B1 (ko) 2022-03-17 2022-03-17 저탄소 배출 공정을 이용한 점착제의 제조방법 및 이를 이용하여 제조된 점착제 테이프의 제조방법.

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KR102423152B1 (ko) * 2022-03-17 2022-07-28 주식회사 켐코 저탄소 배출 공정을 이용한 점착제의 제조방법 및 이를 이용하여 제조된 점착제 테이프의 제조방법.

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