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WO2025211819A1 - Composition adhésive à base de polymère comprenant un matériau à base de graphène et son procédé de préparation - Google Patents

Composition adhésive à base de polymère comprenant un matériau à base de graphène et son procédé de préparation

Info

Publication number
WO2025211819A1
WO2025211819A1 PCT/KR2025/004479 KR2025004479W WO2025211819A1 WO 2025211819 A1 WO2025211819 A1 WO 2025211819A1 KR 2025004479 W KR2025004479 W KR 2025004479W WO 2025211819 A1 WO2025211819 A1 WO 2025211819A1
Authority
WO
WIPO (PCT)
Prior art keywords
polymer
graphene
group
adhesive composition
paragraph
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
PCT/KR2025/004479
Other languages
English (en)
Korean (ko)
Inventor
박종보
이현택
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.)
Graphene Square Chemical Inc
Original Assignee
Graphene Square Chemical Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from KR1020250042958A external-priority patent/KR20250147302A/ko
Application filed by Graphene Square Chemical Inc filed Critical Graphene Square Chemical Inc
Publication of WO2025211819A1 publication Critical patent/WO2025211819A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/02—Elements
    • C08K3/04—Carbon
    • 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
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/02—Non-macromolecular additives
    • C09J11/04—Non-macromolecular additives inorganic
    • 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
    • C09J201/00—Adhesives based on unspecified macromolecular compounds
    • 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
    • C09J5/00—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers
    • C09J5/06—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers involving heating of the applied adhesive
    • 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
    • C09J7/35—Heat-activated

Definitions

  • the present invention relates to a polymer-based adhesive composition comprising a graphene-based material and a method for producing the same.
  • Polymer-based adhesives currently used for assembling and bonding components such as automotive interiors, clothing, and shoes work by heating to a predetermined temperature, then pressing and cooling to bond.
  • the polymer curing temperature is too high, the components may deform or decompose, resulting in poor quality.
  • Working at too low a temperature can take longer and fail to achieve the required bonding strength.
  • conventional adhesives often suffer from uneven heat transfer across the thickness of the component during curing, increasing the defect rate.
  • repeated heat treatments to bond multiple layers of components can lead to product deformation and damage.
  • the inventors of the present invention confirmed that when a graphene-based material is added to an existing polymer-based adhesive, the internal temperature increases more quickly compared to the existing polymer-based adhesive, shortening the curing time and increasing the tensile strength, thereby improving the adhesive strength. Based on this, the present invention was completed.
  • Figure 1b is a drawing showing the results of confirming the change in internal temperature over time by applying infrared heating to a graphene-containing polymer adhesive according to one embodiment of the present invention.
  • FIG. 2a is a drawing showing a photograph of a film formed through infrared heating to confirm the tensile strength of a graphene-containing polymer adhesive film according to one embodiment of the present invention.
  • Figure 2b is a drawing showing the results of confirming the change in tensile strength according to the graphene content in a graphene-containing polymer adhesive film according to one embodiment of the present invention.
  • FIG. 3a is a drawing showing a photograph of a peeling test for confirming the adhesive strength between various materials using a graphene-containing polymer adhesive according to one embodiment of the present invention.
  • Figure 3b is a drawing showing the results of confirming the adhesive strength between various materials using a graphene-containing polymer adhesive according to one embodiment of the present invention.
  • the polymer-based adhesive composition according to the present invention comprises a graphene-based material, and based on the property of graphene absorbing external energy of various wavelengths and releasing it as heat energy, the adhesive performance of the adhesive can be improved, and the cost-effectiveness can be improved through process improvement, thereby reducing the defect rate.
  • the change in tensile strength of a PU adhesive film according to the graphene flake content was confirmed, and as a result, it was confirmed that as the graphene content in the PU solution increases, more external infrared energy is absorbed and released as heat energy, so that more moisture inside is evaporated, and the curing of the adhesive is more effective, and the tensile strength of the film increases (see Example 3).
  • the adhesive strength between various materials was confirmed using an adhesive containing a graphene-based material, and when PU and rubber, ethylene vinyl acetate (EVA) and thermoplastic polyurethane (TPU), and EVA and rubber were bonded, it was confirmed that the adhesive strength of the PU adhesive containing graphene flakes was superior to that of a general PU adhesive (see Example 4).
  • EVA ethylene vinyl acetate
  • TPU thermoplastic polyurethane
  • the present invention relates to a polymer-based adhesive composition comprising a graphene-based material
  • An adhesive composition is provided, characterized in that the polymer is at least one selected from the group consisting of natural polymers, thermosetting polymers, and thermoplastic polymers.
  • the natural polymer may be, but is not limited to, one or more plant-based polymers selected from the group consisting of starch, cellulose, tannin, gum arabic, and sodium alginate, or one or more animal-based polymers selected from the group consisting of bone glue, fish gelatin, blood protein, casein, and shellac.
  • thermosetting polymer may be at least one selected from the group consisting of epoxy, phenolic resin, unsaturated polyester, polyurethane (PU), silicone, polyimide, bismaleimide, allyl resin, furan resin, amino resin, and alkyd resin, but is not limited thereto.
  • the thermoplastic polymer may be at least one selected from the group consisting of polyethylene (PE), polypropylene (PP), polyvinyl chloride (PVC), polystyrene (PS), acrylic resin, nylon, polycarbonate (PC), polyoxymethylene (POM), thermoplastic polyester, polyphenylene ether (PPE), fluoropolymer, polyphenylene sulfide (PPS), polysulfone (PSU), polyketone, polyphenyl ester, and liquid crystal polymer (LCP), but is not limited thereto.
  • PE polyethylene
  • PP polypropylene
  • PVC polyvinyl chloride
  • PS polystyrene
  • acrylic resin nylon
  • PC polycarbonate
  • POM polyoxymethylene
  • thermoplastic polyester polyphenylene ether
  • PPS polyphenylene ether
  • PPS polyphenylene ether
  • PPS polysulfone
  • LCP liquid crystal polymer
  • graphene-based materials means various types of materials that are functionalized or modified while having graphene as the basic structure, and the graphene-based materials may be at least one selected from the group consisting of graphene, graphite, nano/micro graphite, graphene oxide, reduced graphene oxide, graphene quantum dots, reduced graphene quantum dots, carbon nanotubes, carbon black, and carbon dots, but are not limited thereto.
  • the graphene-based material may be graphene or graphite, and the graphene or graphite may have a thickness of 1 nm to 1 mm, 10 nm to 1 mm, 50 nm to 1 mm, 100 nm to 1 mm, 500 nm to 1 mm, 1 ⁇ m to 1 mm, 10 ⁇ m to 1 mm, 50 ⁇ m to 1 mm, 100 ⁇ m to 1 mm, 500 ⁇ m to 1 mm, 1 nm to 500 ⁇ m, 1 nm to 100 ⁇ m, 1 nm to 50 ⁇ m, 1 nm to 10 ⁇ m, 1 nm to 1 ⁇ m, 1 nm to 500 nm, 1 nm to 100 nm, 1 nm to 50 nm, 1 nm to 10 nm, 1 ⁇ m to 500 nm, 1 nm to 100 nm, 1 nm to 50 nm, 1 nm to 10 nm, 1
  • the adhesive composition is a polymer-based adhesive with a graphene-based material added thereto, wherein the graphene-based material is added in an amount of 0.1 to 5% (w/w), 0.1 to 4.5% (w/w), 0.1 to 4% (w/w), 0.1 to 3.5% (w/w), 0.1 to 3% (w/w), 0.1 to 2.5% (w/w), 0.1 to 2% (w/w), 0.1 to 1.5% (w/w), 0.1 to 1% (w/w), 0.2 to 5% (w/w), 0.2 to 4.5% (w/w), 0.2 to 4% (w/w), 0.2 to 3.5% (w/w), 0.2 to 3% (w/w), 0.2 to 2.5% (w/w), 0.2 to 2 %(w/w), 0.2 to 1.5 %(w/w), 0.2 to 1 %(w/w), 0.5 to 5 %(w/w), 0.5 to 4.5 %(w/w), 0.5 to 4
  • the adhesive composition may further include, but is not limited to, one or more selected from the group consisting of a solvent, a curing agent, a plasticizer, a filler, an accelerator, a catalyst, a wetting agent, a surfactant, and a stabilizer.
  • the above solvent may be at least one selected from the group consisting of xylene, cyclohexanone, ethyl acetate, methyl ethyl ketone, toluene, isopropyl alcohol, methyl isobutyl ketone, acetone, butyl acetate, and cellosolve acetate, but is not limited thereto.
  • the above hardener may be one or more selected from the group consisting of isocyanate (NCO), polyamine, and moisture, but is not limited thereto.
  • the above plasticizer may be one or more selected from the group consisting of dioctyl phthalate (DOP), dibutyl phthalate (DBP), and adipic acid esters, but is not limited thereto.
  • DOP dioctyl phthalate
  • DBP dibutyl phthalate
  • adipic acid esters but is not limited thereto.
  • the above filler may be one or more selected from the group consisting of calcium carbonate (CaCO3), silica (SiO2), and titanium oxide (TiO2), but is not limited thereto.
  • the above promoter or catalyst may be an amine or organotin material, but is not limited thereto.
  • Siloxane or fluorine-based surfactants may be used as the above wetting agent or surfactant, but are not limited thereto.
  • the above stabilizer may include, but is not limited to, a UV stabilizer or an antioxidant (BHT, phenols).
  • the adhesive composition can be used for the manufacture of adhesives, sealants, coatings, embedding compounds or moldings, but is not limited thereto.
  • the adhesive composition comprises at least one natural polymer selected from the group consisting of cotton, linen, silk, wool, and fur;
  • One or more synthetic polymers selected from the group consisting of polyester, nylon, rayon, acrylic, polyurethane (PU), rubber, ethylene vinyl acetate (EVA), and thermoplastic polyurethane (TPU); and
  • One or more selected from the group consisting of one or more plastics selected from the group consisting of polyethylene (PE), polypropylene (PP), polystyrene (PS), acrylonitrile butadiene styrene (ABS), polyvinyl chloride (PVC), polyoxymethylene (POM), polytetrafluoroethylene (PTFE), phenol formaldehyde resin (PF), and epoxy resin (EP) can be bonded, but is not limited thereto.
  • the adhesive composition can exhibit high adhesive strength when bonding polyurethane and rubber, but is not limited thereto.
  • the adhesive composition may be heated or cured by one or more external energies selected from the group consisting of infrared light, microwaves, and radio frequencies, but is not limited thereto.
  • the curing time of the polymer-based adhesive can be shortened and the adhesive strength can be increased by utilizing the principle of absorbing external energy and releasing heat.
  • the heating is 40 to 90 °C, 40 to 85 °C, 40 to 80 °C, 40 to 75 °C, 40 to 70 °C, 40 to 65.5 °C, 40 to 60 °C, 40 to 55 °C, 40 to 50 °C, 40 to 45 °C, 45 to 90 °C, 45 to 85 °C, 45 to 80 °C, 45 to 75 °C, 45 to 70 °C, 45 to 65.5 °C, 45 to 60 °C, 45 to 55 °C, 45 to 50 °C, 50 to 90 °C, 50 to 85 °C, 50 to 80 °C, 50 to 75 °C, 50 to 70 °C, 50 to 65.5 °C, 50 to 60 °C, 50 to 55 °C, 55 to 90 °C, 55 to 85 °C, 55 to 80 °C, 55 to 75 °C, 55 to 70 °C, 55 to 60 °C, 60 to 90 °C, 55 to 85 °C, 55 to 80
  • the curing includes drying, and at this time, the drying may be drying at the heating temperature for 5 to 30 minutes, 5 to 25 minutes, 5 to 20 minutes, 10 to 30 minutes, 10 to 25 minutes, 10 to 20 minutes, 15 to 30 minutes, 15 to 25 minutes, 15 to 20 minutes, 20 to 30 minutes, 20 to 25 minutes, or 20 minutes.
  • natural drying may be performed for 12 to 36 hours, 12 to 32 hours, 12 to 28 hours, 12 to 24 hours, 16 to 36 hours, 16 to 32 hours, 16 to 28 hours, 16 to 24 hours, 20 to 36 hours, 20 to 32 hours, 20 to 28 hours, 20 to 24 hours, 24 to 36 hours, 24 to 32 hours, 24 to 28 hours, or 24 hours, but is not limited thereto.
  • the present invention provides a method for preparing the adhesive composition, comprising the step of adding a graphene-based material to a polymer-based adhesive,
  • a manufacturing method is provided, characterized in that the polymer is at least one selected from the group consisting of natural polymers, thermosetting polymers, and thermoplastic polymers.
  • the method comprises adding a graphene-based material to a polymer-based adhesive and bonding the graphene-based material at 100 to 2000 rpm, 100 to 1500 rpm, 100 to 1000 rpm, 500 to 2000 rpm, 500 to 1500 rpm, 500 to 1000 rpm, 1000 to 2000 rpm, 1000 to 1500 rpm, or 1000 rpm for 1 to 30 minutes, 1 to 25 minutes, 1 to 20 minutes, 1 to 15 minutes, 1 to 10 minutes, 5 to 30 minutes, 5 to 25 minutes, 5 to 20 minutes, 5 to 15 minutes, 5 to 10 minutes, 10 to 30 minutes, 10 to 25 minutes, 10 to 20 minutes, 10 to It may include a step of stirring for 15 minutes, or 10 minutes.
  • the temperature during the stirring may be room temperature, for example, 20 to 30°C, 20 to 29°C, 20 to 28°C, 20 to 27°C, 20 to 26°C, 20 to 25°C, 20 to 24°C, 20 to 23°C, 20 to 22°C, 20 to 21°C, 22 to 30°C, 22 to 29°C, 22 to 28°C, 22 to 27°C, 22 to 26°C, 22 to 25°C, 22 to 24°C, 22 to 23°C, 24 to 30°C, 24 to 29°C, 24 to 28°C, 24 to 27°C, 24 to 26 °C, or 24 to 25 °C, but is not limited thereto.
  • the present invention relates to an adhesive use of a polymer-based adhesive composition comprising a graphene-based material,
  • the present invention is for use in the manufacture of a formulation for bonding a polymer-based adhesive composition comprising a graphene-based material,
  • the invention provides a use characterized in that the polymer is at least one selected from the group consisting of natural polymers, thermosetting polymers, and thermoplastic polymers.
  • Example 1 Preparation of a polymer adhesive comprising a graphene-based material.
  • a polyurethane (PU) adhesive solution was prepared by adding an isocyanate (LOCTITE AQUACE ARF-50) as a hardener to a polyol (LOCTITE AQUACE W-90S), a water-based adhesive component, at a volume ratio (v/v) of 100:5 (polyol:isocyanate) and stirring the mixture at 1,000 rpm for 10 minutes at room temperature using a stirrer.
  • LOCTITE AQUACE ARF-50 isocyanate
  • LOCTITE AQUACE W-90S polyol
  • Example 2 Confirmation of internal temperature change under infrared heating (IR heating) of an adhesive containing a graphene-based material.
  • the polymer-based adhesive composition according to the present invention has the effect of increasing the internal temperature more quickly than existing polymer-based adhesives, shortening the curing time and increasing the tensile strength, thereby improving the adhesive strength, and thus can be used more efficiently than existing polymer-based adhesives, and thus has industrial applicability.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Inorganic Chemistry (AREA)
  • Adhesives Or Adhesive Processes (AREA)

Abstract

La présente invention concerne une composition adhésive à base de polymère comprenant un matériau à base de graphène, et son procédé de préparation. La composition adhésive à base de polymère selon la présente invention est obtenue par addition d'un matériau à base de graphène à un adhésif à base de polymère classique. Par comparaison avec les adhésifs classiques, la composition adhésive à base de polymère offre les avantages d'une augmentation plus rapide de la température interne, ce qui permet d'obtenir un temps de durcissement réduit, une résistance à la traction améliorée et une force adhésive améliorée. De plus, la présente invention peut augmenter la qualité de produits en réduisant le temps de traitement thermique et le nombre de cycles de traitement thermique par rapport aux adhésifs classiques, et est respectueuse de l'environnement en réduisant la quantité d'adhésif utilisé. En outre, la présente invention permet la liaison de multiples couches à la fois à l'aide d'un four à micro-ondes ou similaire, réduit les taux de défauts dus à une chaleur élevée générée à l'interface de liaison interne, et permet un décollement beaucoup plus facile par comparaison avec les adhésifs généraux, ce qui est avantageux pour le recyclage.
PCT/KR2025/004479 2024-04-03 2025-04-03 Composition adhésive à base de polymère comprenant un matériau à base de graphène et son procédé de préparation Pending WO2025211819A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
KR20240045327 2024-04-03
KR10-2024-0045327 2024-04-03
KR10-2025-0042958 2025-04-02
KR1020250042958A KR20250147302A (ko) 2024-04-03 2025-04-02 그래핀 기반 물질을 포함하는 고분자 기반 접착제 조성물 및 이의 제조 방법

Publications (1)

Publication Number Publication Date
WO2025211819A1 true WO2025211819A1 (fr) 2025-10-09

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2025/004479 Pending WO2025211819A1 (fr) 2024-04-03 2025-04-03 Composition adhésive à base de polymère comprenant un matériau à base de graphène et son procédé de préparation

Country Status (1)

Country Link
WO (1) WO2025211819A1 (fr)

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20140144576A (ko) * 2013-06-11 2014-12-19 한국신발피혁연구원 전자부품 방열용 접착제 조성물
KR20150011368A (ko) * 2012-05-03 2015-01-30 피피지 인더스트리즈 오하이오 인코포레이티드 그래핀계 탄소 입자를 포함하는 접착제 조성물
US20170233621A1 (en) * 2016-02-08 2017-08-17 Vorbeck Materials Corp. Graphene-containing epoxy adhesives
CN107974231A (zh) * 2016-10-24 2018-05-01 深圳光启空间技术有限公司 胶黏剂、其制备方法及囊体材料
KR20180047950A (ko) * 2016-11-02 2018-05-10 (주)티엘머티리얼 전도성물질을 이용한 전도성 접착 조성물과 그 응용제품
KR20230098130A (ko) * 2020-11-04 2023-07-03 린텍 가부시키가이샤 접착필름, 지지시트를 포함하는 접착필름, 경화체, 및 구조체의 제조방법

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20150011368A (ko) * 2012-05-03 2015-01-30 피피지 인더스트리즈 오하이오 인코포레이티드 그래핀계 탄소 입자를 포함하는 접착제 조성물
KR20140144576A (ko) * 2013-06-11 2014-12-19 한국신발피혁연구원 전자부품 방열용 접착제 조성물
US20170233621A1 (en) * 2016-02-08 2017-08-17 Vorbeck Materials Corp. Graphene-containing epoxy adhesives
CN107974231A (zh) * 2016-10-24 2018-05-01 深圳光启空间技术有限公司 胶黏剂、其制备方法及囊体材料
KR20180047950A (ko) * 2016-11-02 2018-05-10 (주)티엘머티리얼 전도성물질을 이용한 전도성 접착 조성물과 그 응용제품
KR20230098130A (ko) * 2020-11-04 2023-07-03 린텍 가부시키가이샤 접착필름, 지지시트를 포함하는 접착필름, 경화체, 및 구조체의 제조방법

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