WO2023120946A1 - Additive for epoxy adhesive and one-component epoxy adhesive composition comprising same - Google Patents

Additive for epoxy adhesive and one-component epoxy adhesive composition comprising same Download PDF

Info

Publication number
WO2023120946A1
WO2023120946A1 PCT/KR2022/016780 KR2022016780W WO2023120946A1 WO 2023120946 A1 WO2023120946 A1 WO 2023120946A1 KR 2022016780 W KR2022016780 W KR 2022016780W WO 2023120946 A1 WO2023120946 A1 WO 2023120946A1
Authority
WO
WIPO (PCT)
Prior art keywords
epoxy adhesive
formula
compound
additive
epoxy
Prior art date
Application number
PCT/KR2022/016780
Other languages
French (fr)
Korean (ko)
Inventor
최영선
Original Assignee
부산대학교 산학협력단
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
Application filed by 부산대학교 산학협력단 filed Critical 부산대학교 산학협력단
Publication of WO2023120946A1 publication Critical patent/WO2023120946A1/en

Links

Images

Classifications

    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09JADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J11/00Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/08Macromolecular additives
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/20Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
    • C08G59/22Di-epoxy compounds
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/42Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/42Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof
    • C08G59/4207Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof aliphatic
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09JADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J163/00Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins

Definitions

  • the present invention relates to an epoxy adhesive additive and a one-component epoxy adhesive composition comprising the same.
  • Epoxy adhesives have excellent properties such as adhesion to various substrates, heat resistance, chemical resistance, electrical properties, and mechanical properties, and are therefore used in a wide range of industrial fields.
  • Epoxy adhesives include one-component epoxy adhesives in which a single composition is cured, and two-component epoxy adhesives in which a base material and a curing agent are first cured by mixing.
  • One-component epoxy adhesives have the advantage of being more convenient to use than two-component epoxy adhesives.
  • a one-component epoxy adhesive containing a urethane-based intermediate exhibits excellent performance in bonding metal materials.
  • one-component epoxy adhesives containing urethane-based intermediates are inferior in adhesion performance of heterogeneous materials having different polarities, such as between metal and wood or plastic and wood. Therefore, a one-component epoxy adhesive capable of improving adhesion performance between different materials is required, and an epoxy adhesive additive for realizing this is required.
  • One object of the present invention is to provide an additive for an epoxy adhesive capable of improving adhesion performance between different materials.
  • Another object of the present invention is to provide a one-component epoxy adhesive comprising the additive for the epoxy adhesive.
  • the present invention provides an additive for an epoxy adhesive having the following formula (I).
  • X may be a polyether functional group
  • Y may be a polybutadiene functional group
  • Z is selected from one or more of chain-type, branched-chain hydrocarbons and hydrocarbons containing at least one aromatic ring. It may be a functional group, and n may be an integer from 1 to 100.
  • the X may be a functional group having the following formula (II).
  • r may be an integer from 1 to 100
  • s may be an integer from 1 to 100
  • r may be greater than s.
  • Z may be selected from one or more of a functional group having the following formula (III) and a functional group having the following formula (IV).
  • q may be an integer from 1 to 100.
  • the weight ratio of the functional group having Chemical Formula (III) and the functional group having Chemical Formula (IV) may be 2:8 to 4:6.
  • the additive for epoxy adhesive may be obtained by reacting a compound having the following formula (V), a compound having the following formula (VI), a compound having the following formula (VII), and a compound having the following formula (VIII).
  • q may be an integer from 1 to 100
  • r may be an integer from 1 to 100
  • s may be an integer from 1 to 100.
  • the weight ratio of the compound having Formula (V) and the compound having Formula (VI) may be 2:8 to 4:6.
  • the total weight of the compound having the formula (V) and the compound having the formula (VI) may be 60 to 80% by weight, and the weight of the compound having the formula (VII) Silver may be 25 to 35% by weight, and the weight of the compound having Chemical Formula (VIII) may be 2 to 5% by weight.
  • the one-component epoxy adhesive including the additive for epoxy adhesive according to the embodiment of the present invention can improve the adhesive strength between different materials.
  • the present invention provides an additive for an epoxy adhesive having the following formula (IX).
  • Y' may be a polyethylene functional group
  • Z may be a functional group selected from one or more of chain-type, branched-chain hydrocarbons and hydrocarbons containing one or more aromatic rings
  • n' is 1 to 100 may be an integer of
  • Z may be a functional group selected from one or more of a functional group having the following formula (III) and a functional group having the following formula (IV).
  • q may be an integer from 1 to 100.
  • the weight ratio of the functional group having Chemical Formula (III) and the functional group having Chemical Formula (IV) may be 2:8 to 4:6.
  • the additive for the epoxy adhesive may be obtained by reacting a compound having the following formula (V), a compound having the following formula (VI), and the following formula (X).
  • q may be an integer from 1 to 100.
  • the weight ratio of the compound having Formula (V) and the compound having Formula (VI) may be 2:8 to 4:6.
  • the total weight of the additive for the epoxy adhesive is 60 to 80% by weight, and the weight of the compound having the formula (X) is 20 to 40% by weight.
  • the one-component epoxy adhesive including the additive for epoxy adhesive according to the embodiment of the present invention can improve the adhesive strength between different materials.
  • the present invention provides one or more additives for epoxy adhesives among the additives for epoxy adhesives; polymers of at least one of polypropylene glycol (PPG) and polytetramethyleneether glycol (PTMEG); And dicyandiamide (DICY) and imidazole (imidazole) of at least one catalyst; it provides a one-component epoxy adhesive composition comprising a.
  • PPG polypropylene glycol
  • PTMEG polytetramethyleneether glycol
  • DIY dicyandiamide
  • imidazole imidazole
  • the one-component epoxy adhesive composition may have high adhesive shear strength of different materials independently selected from the group including metal, plastic, and wood, compared to the one-component epoxy adhesive composition that does not contain the epoxy adhesive additive. .
  • the additive for an epoxy adhesive according to an embodiment of the present invention is included in a one-component epoxy adhesive, adhesive strength between different materials may be improved.
  • the one-component epoxy adhesive composition according to the embodiment of the present invention may improve adhesive strength between different materials.
  • FIG 1 and 2 are views showing a reaction formula for preparing an additive for an epoxy adhesive according to an embodiment of the present invention.
  • FIG. 1 is a diagram showing an example of a reaction formula for preparing a first additive for an epoxy adhesive among additives for an epoxy adhesive according to an embodiment of the present invention.
  • a first additive for an epoxy adhesive among additives for an epoxy adhesive according to an embodiment of the present invention may have the following Chemical Formula (I).
  • FIG. 1 shows an example of a reaction scheme for preparing a first additive for epoxy adhesive among additives for epoxy adhesive according to an embodiment of the present invention, and the additive for epoxy adhesive having Chemical Formula (I) is not limited to the above manufacturing method. .
  • X may be a polyether functional group
  • Y may be a polybutadiene functional group
  • Z may be chain-like, branched-chain hydrocarbons and hydrocarbons containing one or more aromatic rings. It may be one or more functional groups selected, and n may be an integer from 1 to 100.
  • Additives for epoxy adhesives as described above may be optimized for adhesion of heterogeneous materials having different polarities by introducing a long chain having hydrophobicity.
  • the above additives for epoxy adhesives can be applied to all epoxy adhesive compositions including one-component epoxy adhesive compositions.
  • the X may be a functional group having the following formula (II).
  • r may be an integer from 1 to 100, s may be an integer from 1 to 100, and r may be greater than s.
  • Z may be selected from one or more of a functional group having the following formula (III) and a functional group having the following formula (IV).
  • q may be an integer from 1 to 100.
  • the weight ratio of the functional group having Chemical Formula (III) and the functional group having Chemical Formula (IV) may be 2:8 to 4:6.
  • the additive for epoxy adhesive reacts a compound having the following formula (V), a compound having the following formula (VI), a compound having the following formula (VII), and a compound having the following formula (VIII) can be obtained.
  • q may be an integer from 1 to 100
  • r may be an integer from 1 to 100
  • s may be an integer from 1 to 100.
  • the weight ratio of the compound having Formula (V) and the compound having Formula (VI) may be 2:8 to 4:6.
  • the total weight of the compound having the formula (V) and the compound having the formula (VI) may be 60 to 80% by weight, the formula (VII) ) may be 25 to 35% by weight, and the weight of the compound having Formula (VIII) may be 2 to 5% by weight.
  • FIG. 2 is a view showing an example of a reaction formula for preparing a second additive for an epoxy adhesive among additives for an epoxy adhesive according to an embodiment of the present invention.
  • the second additive for an epoxy adhesive among additives for an epoxy adhesive according to an embodiment of the present invention may have the following Chemical Formula (IX).
  • FIG. 2 shows an example of a reaction scheme for preparing a second additive for epoxy adhesive among additives for epoxy adhesive according to an embodiment of the present invention, and the additive for epoxy adhesive having the formula (IX) is not limited to the above manufacturing method. .
  • Y' may be a polyethylene functional group
  • Z may be a functional group selected from one or more of chain-type, branched-chain hydrocarbons, and hydrocarbons containing one or more aromatic rings
  • n' may be an integer from 1 to 100.
  • Additives for epoxy adhesives as described above may be optimized for adhesion of heterogeneous materials having different polarities by introducing a long chain having hydrophobicity.
  • the above additives for epoxy adhesives can be applied to all epoxy adhesive compositions including one-component epoxy adhesive compositions.
  • Z may be a functional group selected from one or more of a functional group having the following formula (III) and a functional group having the following formula (IV).
  • q may be an integer from 1 to 100.
  • the weight ratio of the functional group having Chemical Formula (III) and the functional group having Chemical Formula (IV) may be 2:8 to 4:6.
  • the additive for the epoxy adhesive may be obtained by reacting a compound having the following Chemical Formula (V), a compound having the following Chemical Formula (VI), and the following Chemical Formula (X).
  • q may be an integer from 1 to 100.
  • the weight ratio of the compound having Formula (V) and the compound having Formula (VI) may be 2:8 to 4:6.
  • the total weight of the compound having the formula (V) and the compound having the formula (VI) is 60 to 80% by weight, the formula (X)
  • the weight of the compound having may be 20 to 40% by weight.
  • the one-component epoxy adhesive composition according to an embodiment of the present invention includes at least one additive for epoxy adhesive among the additives for epoxy adhesive; one or more of the polymers including polyurethane; and a catalyst.
  • the type of the polymer is not particularly limited, but non-limiting examples include polypropylene glycol (PPG) and polytetramethyleneether glycol (PTMEG).
  • PPG polypropylene glycol
  • PTMEG polytetramethyleneether glycol
  • the type of the catalyst is not particularly limited, but non-limiting examples include dicyandiamide (DICY) and imidazole.
  • the one-component epoxy adhesive composition may have high adhesive shear strength of different materials independently selected from the group including metal, plastic, and wood, compared to the one-component epoxy adhesive composition that does not contain the epoxy adhesive additive. .
  • Diglycidyl ether derived from 1,6-hexanediol (first epoxy) and diglycidyl ether derived from bisphenol A (second epoxy) were prepared as epoxy.
  • Ricon® l30MA20 was prepared with maleinized polybutadiene.
  • SURFONAMINE® L-100 was prepared as a polyether amine.
  • Diglycidyl ether derived from 1,6-hexanediol (first epoxy) and diglycidyl ether derived from bisphenol A (second epoxy) were prepared as epoxy.
  • Kumgang MPE-50 was prepared with maleinized ethylene.
  • Methyl ethyl ketone (MEK) was prepared as a solvent.
  • the epoxy 30% by weight of the first epoxy and 70% by weight of the second epoxy were mixed.
  • Epoxy and maleinized ethylene were mixed in a 70:30 weight ratio.
  • the solvent was mixed so as to be 40% of the total weight.
  • the mixed reactants were reacted at 120 °C for 2 hours, and then the solvent was removed in vacuum.
  • the second additive for epoxy adhesives was prepared.
  • Kukdo Chemical YD 128 was prepared as an epoxy for a one-component epoxy adhesive composition.
  • a first additive for an epoxy adhesive according to Example 1 was prepared.
  • Huntsman DY-965 was prepared as a polymer.
  • Epoxy, the additive for the first epoxy adhesive, and the polymer were prepared in a weight ratio of 60:30:10.
  • Silica and silane were prepared as separate additives.
  • Evonik dicyandiamide (DICY) was prepared as a catalyst. 5 phr of silica, 1 phr of silane, and 2.5 phr of catalyst were added. The reactants were mixed to prepare a one-component epoxy adhesive composition according to an embodiment of the present invention.
  • Kukdo Chemical YD 128 was prepared as an epoxy for a one-component epoxy adhesive composition.
  • As an additive for epoxy adhesive a second additive for epoxy adhesive according to Example 2 was prepared. Huntsman DY-965 was prepared as a polymer. Epoxy, the additive for the second epoxy adhesive, and the polymer were prepared in a weight ratio of 60:30:10.
  • Silica and silane were prepared as separate additives.
  • Evonik dicyandiamide (DICY) was prepared as a catalyst. 5 phr of silica, 1 phr of silane, and 2.5 phr of catalyst were added. The reactants were mixed to prepare a one-component epoxy adhesive composition according to an embodiment of the present invention.
  • Kukdo Chemical YD 128 was prepared as an epoxy for a one-component epoxy adhesive composition.
  • additives for epoxy adhesives the first and second additives for epoxy adhesives according to Examples 1 and 2 were both prepared.
  • Huntsman DY-965 was prepared as a polymer.
  • Epoxy, the additive for the first epoxy adhesive, the additive for the second epoxy adhesive, and the polymer were prepared in a weight ratio of 30:30:30:10.
  • Silica and silane were prepared as separate additives.
  • Evonik dicyandiamide (DICY) was prepared as a catalyst. 5 phr of silica, 1 phr of silane, and 2.5 phr of catalyst were added. The reactants were mixed to prepare a one-component epoxy adhesive composition according to an embodiment of the present invention.
  • a one-component epoxy adhesive composition was prepared in the same manner as in Example 3-3, but the epoxy, the first epoxy adhesive additive, the second epoxy adhesive additive, and the polymer were prepared in a weight ratio of 20:40:30:10.
  • a one-component epoxy adhesive composition was prepared in the same manner as in Example 3-3, but the epoxy, the first epoxy adhesive additive, the second epoxy adhesive additive, and the polymer were prepared in a weight ratio of 20:30:40:10.
  • a one-component epoxy adhesive composition was prepared in the same manner as in Example 3-3, but the epoxy, the first epoxy adhesive additive, the second epoxy adhesive additive, and the polymer were prepared in a weight ratio of 10:40:40:10.
  • Kukdo Chemical YD 128 was prepared as an epoxy for a one-component epoxy adhesive composition.
  • Huntsman DY-965 was prepared as a polymer. Epoxy and polymer were prepared in a weight ratio of 90:10.
  • Silica and silane were prepared as separate additives.
  • Evonik dicyandiamide (DICY) was prepared as a catalyst. 5 phr of silica, 1 phr of silane, and 2.5 phr of catalyst were added. The reactants were mixed to prepare a one-component epoxy adhesive composition according to a comparative example of the present invention.
  • Test pieces of SUS and HDPE were prepared for the measurement of heterogeneous adhesive shear strength. Each specimen was prepared with a size of 100 mm ⁇ 25 mm. Both test pieces were arranged to overlap each other by 12.7 mm in the longitudinal direction, and the epoxy adhesive composition according to Examples 3-1 to 3-6 and Comparative Example 1 was applied to the overlapping portion to a thickness of 0.2 mm. Both test pieces were cured at 200 to 220 degrees for 30 minutes by applying a pressure of 25 kgf/cm 2 using a pressure jig.
  • the one-component epoxy adhesive composition to which one is added has two or more times the bonding strength of different materials.
  • the first The one-component epoxy adhesive composition to which both the additive for epoxy adhesive and the additive for second epoxy adhesive according to Example 2 of the present invention are added is the first additive for epoxy adhesive according to Example 1 of the present invention or the embodiment of the present invention. It can be seen that the adhesive strength of the second epoxy adhesive according to 2 is somewhat stronger than that of the one-component epoxy adhesive composition to which one of the additives for epoxy adhesive is added.
  • the first epoxy adhesive additive according to Example 1 of the present invention and the second epoxy adhesive additive according to Example 2 of the present invention have a content of a certain level or more In this case, it can be confirmed that the adhesive strength of the different materials is slightly reduced again. This is because the additive for epoxy adhesive according to the embodiment of the present invention contributes to the adhesion of materials having hydrophobicity, but the adhesive strength to materials having polarity decreases when the content increases above a certain level.

Landscapes

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

Abstract

Disclosed are an additive for an epoxy adhesive and a one-component epoxy adhesive composition comprising same. The additive for an epoxy adhesive may be obtained by reacting epoxy, maleinized polybutadiene and polyetheramine. In addition, the additive for the epoxy adhesive may be obtained by reacting epoxy and maleinized ethylene. The one-component epoxy adhesive composition may include, of the additives for an epoxy adhesive, one or more additives for an epoxy adhesive, a urethane polymer, and a catalyst.

Description

에폭시 접착제용 첨가제 및 이를 포함하는 일액형 에폭시 접착제 조성물Additive for epoxy adhesive and one-component epoxy adhesive composition containing the same
본 발명은 에폭시 접착제용 첨가제 및 이를 포함하는 일액형 에폭시 접착제 조성물에 관한 것이다.The present invention relates to an epoxy adhesive additive and a one-component epoxy adhesive composition comprising the same.
에폭시 접착제는 각종 기재에 대한 접착성, 내열성, 내약품성, 전기 특성, 기계 특성 등 우수한 특성을 가지고 있어 넓은 산업 분야에서 이용되고 있다. 에폭시 접착제에는 단일 조성물이 경화되는 일액형 에폭시 접착제 및 주제와 경화제의 혼합에 의해 비로소 경화되는 이액형 에폭시 접착제가 있다. Epoxy adhesives have excellent properties such as adhesion to various substrates, heat resistance, chemical resistance, electrical properties, and mechanical properties, and are therefore used in a wide range of industrial fields. Epoxy adhesives include one-component epoxy adhesives in which a single composition is cured, and two-component epoxy adhesives in which a base material and a curing agent are first cured by mixing.
일액형 에폭시 접착제는 이액형 에폭시 접착제에 비해 사용하기 편리하다는 장점이 있다. 특히, 우레탄 기반 중간체를 포함하는 일액형 에폭시 접착제는 금속 재질 접착에 우수한 성능을 보인다. 그러나 우레탄 기반 중간체를 포함하는 일액형 에폭시 접착제는 극성이 서로 다른 이종 재질의 접착 성능, 예컨대 금속과 목재 또는 플라스틱과 목재 등의 접착 성능이 열등하다. 따라서 이종 재질 간의 접착 성능을 향상할 수 있는 일액형 에폭시 접착제가 요구되며, 이를 구현하기 위한 에폭시 접착제용 첨가제가 요구된다.One-component epoxy adhesives have the advantage of being more convenient to use than two-component epoxy adhesives. In particular, a one-component epoxy adhesive containing a urethane-based intermediate exhibits excellent performance in bonding metal materials. However, one-component epoxy adhesives containing urethane-based intermediates are inferior in adhesion performance of heterogeneous materials having different polarities, such as between metal and wood or plastic and wood. Therefore, a one-component epoxy adhesive capable of improving adhesion performance between different materials is required, and an epoxy adhesive additive for realizing this is required.
본 발명의 일 목적은 이종 재질 간의 접착 성능을 향상할 수 있는 에폭시 접착제용 첨가제를 제공하는 것이다.One object of the present invention is to provide an additive for an epoxy adhesive capable of improving adhesion performance between different materials.
본 발명의 다른 목적은 상기 에폭시 접착제용 첨가제를 포함하는 일액형 에폭시 접착제를 제공하는 것이다.Another object of the present invention is to provide a one-component epoxy adhesive comprising the additive for the epoxy adhesive.
일 측면에서 본 발명은 하기 화학식(Ⅰ)을 가지는, 에폭시 접착제용 첨가제를 제공한다.In one aspect, the present invention provides an additive for an epoxy adhesive having the following formula (I).
Figure PCTKR2022016780-appb-img-000001
(Ⅰ)
Figure PCTKR2022016780-appb-img-000001
(Ⅰ)
여기서, X는 폴리에테르(polyether) 작용기일 수 있고, Y는 폴리부타디엔(polybutadiene) 작용기일 수 있으며, Z는 사슬형, 분지된 사슬형 탄화수소 및 하나 이상의 방향족 고리를 포함하는 탄화수소 중 하나 이상으로 선택되는 작용기일 수 있고, n은 1 내지 100의 정수일 수 있다.Here, X may be a polyether functional group, Y may be a polybutadiene functional group, and Z is selected from one or more of chain-type, branched-chain hydrocarbons and hydrocarbons containing at least one aromatic ring. It may be a functional group, and n may be an integer from 1 to 100.
상기 X는 하기 화학식(Ⅱ)를 가지는 작용기일 수 있다.The X may be a functional group having the following formula (II).
Figure PCTKR2022016780-appb-img-000002
(Ⅱ)
Figure PCTKR2022016780-appb-img-000002
(II)
여기서, r은 1 내지 100의 정수일 수 있고, s는 1 내지 100의 정수일 수 있으며, r은 s보다 클 수 있다.Here, r may be an integer from 1 to 100, s may be an integer from 1 to 100, and r may be greater than s.
상기 Z는 하기 화학식(Ⅲ)을 가지는 작용기 및 하기 화학식(Ⅳ)을 가지는 작용기 중 하나 이상으로 선택될 수 있다.Z may be selected from one or more of a functional group having the following formula (III) and a functional group having the following formula (IV).
Figure PCTKR2022016780-appb-img-000003
(Ⅲ)
Figure PCTKR2022016780-appb-img-000003
(III)
Figure PCTKR2022016780-appb-img-000004
(Ⅳ)
Figure PCTKR2022016780-appb-img-000004
(IV)
여기서, q는 1 내지 100의 정수일 수 있다.Here, q may be an integer from 1 to 100.
상기 화학식(Ⅲ)을 가지는 작용기 및 상기 화학식(Ⅳ)을 가지는 작용기의 중량비는 2:8 내지 4:6일 수 있다.The weight ratio of the functional group having Chemical Formula (III) and the functional group having Chemical Formula (IV) may be 2:8 to 4:6.
상기 에폭시 접착제용 첨가제는 하기 화학식(Ⅴ)을 가지는 화합물, 하기 화학식(Ⅵ)을 가지는 화합물, 하기 화학식(Ⅶ)을 가지는 화합물 및 하기 화학식(ⅤⅢ)을 가지는 화합물을 반응하여 수득될 수 있다.The additive for epoxy adhesive may be obtained by reacting a compound having the following formula (V), a compound having the following formula (VI), a compound having the following formula (VII), and a compound having the following formula (VIII).
Figure PCTKR2022016780-appb-img-000005
(Ⅴ)
Figure PCTKR2022016780-appb-img-000005
(V)
Figure PCTKR2022016780-appb-img-000006
(Ⅵ)
Figure PCTKR2022016780-appb-img-000006
(VI)
Figure PCTKR2022016780-appb-img-000007
(Ⅶ)
Figure PCTKR2022016780-appb-img-000007
(VII)
Figure PCTKR2022016780-appb-img-000008
(ⅤⅢ)
Figure PCTKR2022016780-appb-img-000008
(ⅤⅢ)
여기서, q는 1 내지 100의 정수일 수 있고, r은 1 내지 100의 정수일 수 있으며, s는 1 내지 100의 정수일 수 있다.Here, q may be an integer from 1 to 100, r may be an integer from 1 to 100, and s may be an integer from 1 to 100.
상기 화학식(Ⅴ)을 가지는 화합물과 상기 화학식(Ⅵ)을 가지는 화합물의 중량비는 2:8 내지 4:6일 수 있다.The weight ratio of the compound having Formula (V) and the compound having Formula (VI) may be 2:8 to 4:6.
상기 에폭시 접착제용 첨가제 총 중량에 대하여, 상기 화학식(Ⅴ)을 가지는 화합물과 상기 화학식(Ⅵ)을 가지는 화합물의 총 중량은 60 내지 80 중량% 일 수 있고, 상기 화학식(Ⅶ)을 가지는 화합물의 중량은 25 내지 35 중량% 일 수 있으며, 상기 화학식(ⅤⅢ)을 가지는 화합물의 중량은 2 내지 5 중량% 일 수 있다.With respect to the total weight of the additive for the epoxy adhesive, the total weight of the compound having the formula (V) and the compound having the formula (VI) may be 60 to 80% by weight, and the weight of the compound having the formula (VII) Silver may be 25 to 35% by weight, and the weight of the compound having Chemical Formula (VIII) may be 2 to 5% by weight.
상기와 같은 구성을 통해 본 발명의 실시예에 따른 에폭시 접착제용 첨가제를 포함하는 일액형 에폭시 접착제는 이종 재질간 접착 강도가 향상될 수 있다.Through the configuration as described above, the one-component epoxy adhesive including the additive for epoxy adhesive according to the embodiment of the present invention can improve the adhesive strength between different materials.
다른 측면에서 본 발명은 하기 화학식(Ⅸ)를 가지는 에폭시 접착제용 첨가제를 제공한다.In another aspect, the present invention provides an additive for an epoxy adhesive having the following formula (IX).
Figure PCTKR2022016780-appb-img-000009
(Ⅸ)
Figure PCTKR2022016780-appb-img-000009
(Ⅸ)
여기서, Y'는 폴리에틸렌(polyethylene) 작용기일 수 있고, Z는 사슬형, 분지된 사슬형 탄화수소 및 하나 이상의 방향족 고리를 포함하는 탄화수소 중 하나 이상으로 선택되는 작용기일 수 있으며, n'은 1 내지 100의 정수일 수 있다.Here, Y' may be a polyethylene functional group, Z may be a functional group selected from one or more of chain-type, branched-chain hydrocarbons and hydrocarbons containing one or more aromatic rings, and n' is 1 to 100 may be an integer of
상기 Z는 하기 화학식(Ⅲ)을 가지는 작용기 및 하기 화학식(Ⅳ)을 가지는 작용기 중 하나 이상으로 선택되는 작용기일 수 있다.Z may be a functional group selected from one or more of a functional group having the following formula (III) and a functional group having the following formula (IV).
Figure PCTKR2022016780-appb-img-000010
(Ⅲ)
Figure PCTKR2022016780-appb-img-000010
(III)
Figure PCTKR2022016780-appb-img-000011
(Ⅳ)
Figure PCTKR2022016780-appb-img-000011
(IV)
여기서, q는 1 내지 100의 정수일 수 있다.Here, q may be an integer from 1 to 100.
상기 화학식(Ⅲ)을 가지는 작용기 및 상기 화학식(Ⅳ)을 가지는 작용기의 중량비는 2:8 내지 4:6일 수 있다.The weight ratio of the functional group having Chemical Formula (III) and the functional group having Chemical Formula (IV) may be 2:8 to 4:6.
상기 에폭시 접착제용 첨가제는, 하기 화학식(Ⅴ)을 가지는 화합물, 하기 화학식(Ⅵ)을 가지는 화합물 및 하기 화학식(Ⅹ)을 반응하여 수득될 수 있다.The additive for the epoxy adhesive may be obtained by reacting a compound having the following formula (V), a compound having the following formula (VI), and the following formula (X).
Figure PCTKR2022016780-appb-img-000012
(Ⅴ)
Figure PCTKR2022016780-appb-img-000012
(V)
Figure PCTKR2022016780-appb-img-000013
(Ⅵ)
Figure PCTKR2022016780-appb-img-000013
(VI)
Figure PCTKR2022016780-appb-img-000014
(Ⅹ)
Figure PCTKR2022016780-appb-img-000014
(X)
여기서, q는 1 내지 100의 정수일 수 있다.Here, q may be an integer from 1 to 100.
상기 화학식(Ⅴ)을 가지는 화합물과 상기 화학식(Ⅵ)을 가지는 화합물의 중량비는 2:8 내지 4:6일 수 있다.The weight ratio of the compound having Formula (V) and the compound having Formula (VI) may be 2:8 to 4:6.
상기 에폭시 접착제용 첨가제 총 중량에 대하여, 상기 화학식(Ⅴ)을 가지는 화합물과 상기 화학식(Ⅵ)을 가지는 화합물의 총 중량은 60 내지 80 중량% 이고, 상기 화학식(Ⅹ)을 가지는 화합물의 중량은 20 내지 40 중량% 일 수 있다.With respect to the total weight of the additive for the epoxy adhesive, the total weight of the compound having the formula (V) and the compound having the formula (VI) is 60 to 80% by weight, and the weight of the compound having the formula (X) is 20 to 40% by weight.
상기와 같은 구성을 통해 본 발명의 실시예에 따른 에폭시 접착제용 첨가제를 포함하는 일액형 에폭시 접착제는 이종 재질간 접착 강도가 향상될 수 있다.Through the configuration as described above, the one-component epoxy adhesive including the additive for epoxy adhesive according to the embodiment of the present invention can improve the adhesive strength between different materials.
또 다른 측면에서 본 발명은, 상기 에폭시 접착제용 첨가제 중 하나 이상의 에폭시 접착제용 첨가제; 폴리프로필렌 글리콜(polypropylene glycol; PPG) 및 폴리테트라메틸렌에테르 글리콜(polytetramethyleneether glycol; PTMEG) 중 하나 이상의 폴리머; 및 디사이안디아마이드(dicyandiamide; DICY) 및 이미다졸(imidazole) 중 하나 이상의 촉매;를 포함하는, 일액형 에폭시 접착제 조성물을 제공한다.In another aspect, the present invention provides one or more additives for epoxy adhesives among the additives for epoxy adhesives; polymers of at least one of polypropylene glycol (PPG) and polytetramethyleneether glycol (PTMEG); And dicyandiamide (DICY) and imidazole (imidazole) of at least one catalyst; it provides a one-component epoxy adhesive composition comprising a.
상기 일액형 에폭시 접착제 조성물은 상기 에폭시 접착제용 첨가제를 포함하지 않는 일액형 에폭시 접착제 조성물에 비해 금속, 플라스틱 및 목재를 포함하는 군에서 각각 독립적으로 서로 다르게 선택되는 이종 재질의 접착 전단 강도가 높을 수 있다.The one-component epoxy adhesive composition may have high adhesive shear strength of different materials independently selected from the group including metal, plastic, and wood, compared to the one-component epoxy adhesive composition that does not contain the epoxy adhesive additive. .
본 발명의 실시예에 따른 에폭시 접착제용 첨가제는 일액형 에폭시 접착제에 포함되었을 때 이종 재질 간 접착 강도가 향상될 수 있다.When the additive for an epoxy adhesive according to an embodiment of the present invention is included in a one-component epoxy adhesive, adhesive strength between different materials may be improved.
본 발명의 실시예에 따른 일액형 에폭시 접착제 조성물은 이종 재질 간 접착 강도가 향상될 수 있다.The one-component epoxy adhesive composition according to the embodiment of the present invention may improve adhesive strength between different materials.
도 1 및 도 2는 본 발명의 실시예에 따른 에폭시 접착제용 첨가제를 제조하는 반응식을 나타낸 도면이다.1 and 2 are views showing a reaction formula for preparing an additive for an epoxy adhesive according to an embodiment of the present invention.
이하, 첨부한 도면을 참조하여 본 발명의 실시예에 대해 상세히 설명한다. 본 발명은 다양한 변경을 가할 수 있고 여러 가지 형태를 가질 수 있는 바, 특정 실시 예들을 도면에 예시하고 본문에 상세하게 설명하고자 한다. 그러나 이는 본 발명을 특정한 개시 형태에 대해 한정하려는 것이 아니며, 본 발명의 사상 및 기술 범위에 포함되는 모든 변경, 균등물 내지 대체물을 포함하는 것으로 이해되어야 한다. 각 도면을 설명하면서 유사한 참조부호를 유사한 구성요소에 대해 사용하였다. 첨부된 도면에 있어서, 구조물들의 치수는 본 발명의 명확성을 기하기 위하여 실제보다 확대하여 도시한 것이다. Hereinafter, embodiments of the present invention will be described in detail with reference to the accompanying drawings. Since the present invention can have various changes and various forms, specific embodiments will be illustrated in the drawings and described in detail in the text. However, this is not intended to limit the present invention to a specific form disclosed, and should be understood to include all modifications, equivalents, and substitutes included in the spirit and scope of the present invention. Like reference numerals have been used for like elements throughout the description of each figure. In the accompanying drawings, the dimensions of the structures are shown enlarged than actual for clarity of the present invention.
본 출원에서 사용한 용어는 단지 특정한 실시 예를 설명하기 위해 사용된 것으로, 본 발명을 한정하려는 의도가 아니다. 단수의 표현은 문맥상 명백하게 다르게 뜻하지 않는 한, 복수의 표현을 포함한다. 본 출원에서, "포함하다" 또는 "가지다" 등의 용어는 명세서 상에 기재된 특징, 숫자, 단계, 동작, 구성요소 또는 이들을 조합한 것이 존재함을 지정하려는 것이지, 하나 또는 그 이상의 다른 특징들이나 숫자, 단계, 동작, 구성요소 또는 이들을 조합한 것들의 존재 또는 부가 가능성을 미리 배제하지 않는 것으로 이해되어야 한다.Terms used in this application are only used to describe specific embodiments, and are not intended to limit the present invention. Singular expressions include plural expressions unless the context clearly dictates otherwise. In this application, terms such as "comprise" or "have" are intended to designate that there is a feature, number, step, operation, component, or combination thereof described in the specification, but one or more other features or numbers However, it should be understood that it does not preclude the presence or addition of steps, operations, components, or combinations thereof.
다르게 정의되지 않는 한, 기술적이거나 과학적인 용어를 포함해서 여기서 사용되는 모든 용어들은 본 발명이 속하는 기술 분야에서 통상의 지식을 가진 자에 의해 일반적으로 이해되는 것과 동일한 의미를 가지고 있다. 일반적으로 사용되는 사전에 정의되어 있는 것과 같은 용어들은 관련 기술의 문맥 상 가지는 의미와 일치하는 의미를 가지는 것으로 해석되어야 하며, 본 출원에서 명백하게 정의하지 않는 한, 이상적이거나 과도하게 형식적인 의미로 해석되지 않는다. Unless defined otherwise, all terms used herein, including technical or scientific terms, have the same meaning as commonly understood by one of ordinary skill in the art to which the present invention belongs. Terms such as those defined in commonly used dictionaries should be interpreted as having a meaning consistent with the meaning in the context of the related art, and unless explicitly defined in the present application, they should not be interpreted in an ideal or excessively formal meaning. don't
도 1은 본 발명의 실시예에 따른 에폭시 접착제용 첨가제 중 제1 에폭시 접착제용 첨가제를 제조하는 반응식의 일례를 나타낸 도면이다.1 is a diagram showing an example of a reaction formula for preparing a first additive for an epoxy adhesive among additives for an epoxy adhesive according to an embodiment of the present invention.
도 1을 참조하면, 본 발명의 실시예에 따른 에폭시 접착제용 첨가제 중 제1 에폭시 접착제용 첨가제는 하기 화학식(Ⅰ)을 가질 수 있다. Referring to FIG. 1 , a first additive for an epoxy adhesive among additives for an epoxy adhesive according to an embodiment of the present invention may have the following Chemical Formula (I).
Figure PCTKR2022016780-appb-img-000015
(Ⅰ)
Figure PCTKR2022016780-appb-img-000015
(Ⅰ)
도 1은 본 발명의 실시예에 따른 에폭시 접착제용 첨가제 중 제1 에폭시 접착제용 첨가제를 제조하는 반응식의 일례를 나타낸 것이며, 상기 화학식(Ⅰ)을 가지는 에폭시 접착제용 첨가제는 상기 제조 방법에 한정되지 않는다.1 shows an example of a reaction scheme for preparing a first additive for epoxy adhesive among additives for epoxy adhesive according to an embodiment of the present invention, and the additive for epoxy adhesive having Chemical Formula (I) is not limited to the above manufacturing method. .
일 실시예에 있어서, X는 폴리에테르(polyether) 작용기일 수 있고, Y는 폴리부타디엔(polybutadiene) 작용기일 수 있으며, Z는 사슬형, 분지된 사슬형 탄화수소 및 하나 이상의 방향족 고리를 포함하는 탄화수소 중 하나 이상으로 선택되는 작용기일 수 있고, n은 1 내지 100의 정수일 수 있다.In one embodiment, X may be a polyether functional group, Y may be a polybutadiene functional group, and Z may be chain-like, branched-chain hydrocarbons and hydrocarbons containing one or more aromatic rings. It may be one or more functional groups selected, and n may be an integer from 1 to 100.
상기와 같은 에폭시 접착제용 첨가제는 소수성을 갖는 긴사슬이 도입되어 극성이 서로 다른 이종의 재질의 접착에도 최적화될 수 있다.Additives for epoxy adhesives as described above may be optimized for adhesion of heterogeneous materials having different polarities by introducing a long chain having hydrophobicity.
상기와 같은 에폭시 접착제용 첨가제는 일액형 에폭시 접착제 조성물을 포함한 모든 에폭시 접착제 조성물에 적용할 수 있다.The above additives for epoxy adhesives can be applied to all epoxy adhesive compositions including one-component epoxy adhesive compositions.
일 실시예에 있어서, 상기 X는 하기 화학식(Ⅱ)를 가지는 작용기일 수 있다.In one embodiment, the X may be a functional group having the following formula (II).
Figure PCTKR2022016780-appb-img-000016
(Ⅱ)
Figure PCTKR2022016780-appb-img-000016
(II)
일 실시예에 있어서, r은 1 내지 100의 정수일 수 있고, s는 1 내지 100의 정수일 수 있으며, r은 s보다 클 수 있다.In one embodiment, r may be an integer from 1 to 100, s may be an integer from 1 to 100, and r may be greater than s.
일 실시예에 있어서, 상기 Z는 하기 화학식(Ⅲ)을 가지는 작용기 및 하기 화학식(Ⅳ)을 가지는 작용기 중 하나 이상으로 선택될 수 있다.In one embodiment, Z may be selected from one or more of a functional group having the following formula (III) and a functional group having the following formula (IV).
Figure PCTKR2022016780-appb-img-000017
(Ⅲ)
Figure PCTKR2022016780-appb-img-000017
(III)
Figure PCTKR2022016780-appb-img-000018
(Ⅳ)
Figure PCTKR2022016780-appb-img-000018
(IV)
일 실시예에 있어서, q는 1 내지 100의 정수일 수 있다.In one embodiment, q may be an integer from 1 to 100.
일 실시예에 있어서, 상기 화학식(Ⅲ)을 가지는 작용기 및 상기 화학식(Ⅳ)을 가지는 작용기의 중량비는 2:8 내지 4:6일 수 있다.In one embodiment, the weight ratio of the functional group having Chemical Formula (III) and the functional group having Chemical Formula (IV) may be 2:8 to 4:6.
일 실시예에 있어서, 상기 에폭시 접착제용 첨가제는 하기 화학식(Ⅴ)을 가지는 화합물, 하기 화학식(Ⅵ)을 가지는 화합물, 하기 화학식(Ⅶ)을 가지는 화합물 및 하기 화학식(ⅤⅢ)을 가지는 화합물을 반응하여 수득될 수 있다.In one embodiment, the additive for epoxy adhesive reacts a compound having the following formula (V), a compound having the following formula (VI), a compound having the following formula (VII), and a compound having the following formula (VIII) can be obtained.
Figure PCTKR2022016780-appb-img-000019
(Ⅴ)
Figure PCTKR2022016780-appb-img-000019
(V)
Figure PCTKR2022016780-appb-img-000020
(Ⅵ)
Figure PCTKR2022016780-appb-img-000020
(VI)
Figure PCTKR2022016780-appb-img-000021
(Ⅶ)
Figure PCTKR2022016780-appb-img-000021
(VII)
Figure PCTKR2022016780-appb-img-000022
(ⅤⅢ)
Figure PCTKR2022016780-appb-img-000022
(ⅤⅢ)
일 실시예에 있어서, q는 1 내지 100의 정수일 수 있고, r은 1 내지 100의 정수일 수 있으며, s는 1 내지 100의 정수일 수 있다.In one embodiment, q may be an integer from 1 to 100, r may be an integer from 1 to 100, and s may be an integer from 1 to 100.
일 실시예에 있어서, 상기 화학식(Ⅴ)을 가지는 화합물과 상기 화학식(Ⅵ)을 가지는 화합물의 중량비는 2:8 내지 4:6일 수 있다.In one embodiment, the weight ratio of the compound having Formula (V) and the compound having Formula (VI) may be 2:8 to 4:6.
일 실시예에 있어서, 상기 에폭시 접착제용 첨가제 총 중량에 대하여, 상기 화학식(Ⅴ)을 가지는 화합물과 상기 화학식(Ⅵ)을 가지는 화합물의 총 중량은 60 내지 80 중량% 일 수 있고, 상기 화학식(Ⅶ)을 가지는 화합물의 중량은 25 내지 35 중량% 일 수 있으며, 상기 화학식(ⅤⅢ)을 가지는 화합물의 중량은 2 내지 5 중량% 일 수 있다.In one embodiment, with respect to the total weight of the additive for the epoxy adhesive, the total weight of the compound having the formula (V) and the compound having the formula (VI) may be 60 to 80% by weight, the formula (VII) ) may be 25 to 35% by weight, and the weight of the compound having Formula (VIII) may be 2 to 5% by weight.
도 2는 본 발명의 실시예에 따른 에폭시 접착제용 첨가제 중 제2 에폭시 접착제용 첨가제를 제조하는 반응식의 일례를 나타낸 도면이다.2 is a view showing an example of a reaction formula for preparing a second additive for an epoxy adhesive among additives for an epoxy adhesive according to an embodiment of the present invention.
도 2를 참조하면, 본 발명의 실시예에 따른 에폭시 접착제용 첨가제 중 제2 에폭시 접착제용 첨가제는 하기 화학식(Ⅸ)을 가질 수 있다. Referring to FIG. 2 , the second additive for an epoxy adhesive among additives for an epoxy adhesive according to an embodiment of the present invention may have the following Chemical Formula (IX).
Figure PCTKR2022016780-appb-img-000023
(Ⅸ)
Figure PCTKR2022016780-appb-img-000023
(Ⅸ)
도 2는 본 발명의 실시예에 따른 에폭시 접착제용 첨가제 중 제2 에폭시 접착제용 첨가제를 제조하는 반응식의 일례를 나타낸 것이며, 상기 화학식(Ⅸ)을 가지는 에폭시 접착제용 첨가제는 상기 제조 방법에 한정되지 않는다.2 shows an example of a reaction scheme for preparing a second additive for epoxy adhesive among additives for epoxy adhesive according to an embodiment of the present invention, and the additive for epoxy adhesive having the formula (IX) is not limited to the above manufacturing method. .
일 실시예에 있어서, Y'는 폴리에틸렌(polyethylene) 작용기일 수 있고, Z는 사슬형, 분지된 사슬형 탄화수소 및 하나 이상의 방향족 고리를 포함하는 탄화수소 중 하나 이상으로 선택되는 작용기일 수 있으며, n'은 1 내지 100의 정수일 수 있다.In one embodiment, Y' may be a polyethylene functional group, Z may be a functional group selected from one or more of chain-type, branched-chain hydrocarbons, and hydrocarbons containing one or more aromatic rings, and n' may be an integer from 1 to 100.
상기와 같은 에폭시 접착제용 첨가제는 소수성을 갖는 긴사슬이 도입되어 극성이 서로 다른 이종의 재질의 접착에도 최적화될 수 있다.Additives for epoxy adhesives as described above may be optimized for adhesion of heterogeneous materials having different polarities by introducing a long chain having hydrophobicity.
상기와 같은 에폭시 접착제용 첨가제는 일액형 에폭시 접착제 조성물을 포함한 모든 에폭시 접착제 조성물에 적용할 수 있다.The above additives for epoxy adhesives can be applied to all epoxy adhesive compositions including one-component epoxy adhesive compositions.
일 실시예에 있어서, 상기 Z는 하기 화학식(Ⅲ)을 가지는 작용기 및 하기 화학식(Ⅳ)을 가지는 작용기 중 하나 이상으로 선택되는 작용기일 수 있다.In one embodiment, Z may be a functional group selected from one or more of a functional group having the following formula (III) and a functional group having the following formula (IV).
Figure PCTKR2022016780-appb-img-000024
(Ⅲ)
Figure PCTKR2022016780-appb-img-000024
(III)
Figure PCTKR2022016780-appb-img-000025
(Ⅳ)
Figure PCTKR2022016780-appb-img-000025
(IV)
일 실시예에 있어서, q는 1 내지 100의 정수일 수 있다.In one embodiment, q may be an integer from 1 to 100.
일 실시예에 있어서, 상기 화학식(Ⅲ)을 가지는 작용기 및 상기 화학식(Ⅳ)을 가지는 작용기의 중량비는 2:8 내지 4:6일 수 있다.In one embodiment, the weight ratio of the functional group having Chemical Formula (III) and the functional group having Chemical Formula (IV) may be 2:8 to 4:6.
일 실시예에 있어서, 상기 에폭시 접착제용 첨가제는, 하기 화학식(Ⅴ)을 가지는 화합물, 하기 화학식(Ⅵ)을 가지는 화합물 및 하기 화학식(Ⅹ)을 반응하여 수득될 수 있다.In one embodiment, the additive for the epoxy adhesive may be obtained by reacting a compound having the following Chemical Formula (V), a compound having the following Chemical Formula (VI), and the following Chemical Formula (X).
Figure PCTKR2022016780-appb-img-000026
(Ⅴ)
Figure PCTKR2022016780-appb-img-000026
(V)
Figure PCTKR2022016780-appb-img-000027
(Ⅵ)
Figure PCTKR2022016780-appb-img-000027
(VI)
Figure PCTKR2022016780-appb-img-000028
(Ⅹ)
Figure PCTKR2022016780-appb-img-000028
(X)
일 실시예에 있어서, q는 1 내지 100의 정수일 수 있다.In one embodiment, q may be an integer from 1 to 100.
일 실시예에 있어서, 상기 화학식(Ⅴ)을 가지는 화합물과 상기 화학식(Ⅵ)을 가지는 화합물의 중량비는 2:8 내지 4:6일 수 있다.In one embodiment, the weight ratio of the compound having Formula (V) and the compound having Formula (VI) may be 2:8 to 4:6.
일 실시예에 있어서, 상기 에폭시 접착제용 첨가제 총 중량에 대하여, 상기 화학식(Ⅴ)을 가지는 화합물과 상기 화학식(Ⅵ)을 가지는 화합물의 총 중량은 60 내지 80 중량% 이고, 상기 화학식(Ⅹ)을 가지는 화합물의 중량은 20 내지 40 중량% 일 수 있다.In one embodiment, with respect to the total weight of the additive for the epoxy adhesive, the total weight of the compound having the formula (V) and the compound having the formula (VI) is 60 to 80% by weight, the formula (X) The weight of the compound having may be 20 to 40% by weight.
한편, 본 발명의 실시예에 따른 일액형 에폭시 접착제 조성물은 상기 에폭시 접착제용 첨가제 중 하나 이상의 에폭시 접착제용 첨가제; 폴리우레탄을 포함하는 폴리머 중 하나 이상; 및 촉매를 포함할 수 있다.On the other hand, the one-component epoxy adhesive composition according to an embodiment of the present invention includes at least one additive for epoxy adhesive among the additives for epoxy adhesive; one or more of the polymers including polyurethane; and a catalyst.
상기 폴리머의 종류는 특별히 제한되지 않으나, 비제한적인 예시는 폴리프로필렌 글리콜(polypropylene glycol; PPG) 및 폴리테트라메틸렌에테르 글리콜(polytetramethyleneether glycol; PTMEG)을 포함한다.The type of the polymer is not particularly limited, but non-limiting examples include polypropylene glycol (PPG) and polytetramethyleneether glycol (PTMEG).
상기 촉매의 종류는 특별히 제한되지 않으나, 비제한적인 예시는 디사이안디아마이드(dicyandiamide; DICY) 및 이미다졸(imidazole)을 포함한다.The type of the catalyst is not particularly limited, but non-limiting examples include dicyandiamide (DICY) and imidazole.
상기 일액형 에폭시 접착제 조성물은 상기 에폭시 접착제용 첨가제를 포함하지 않는 일액형 에폭시 접착제 조성물에 비해 금속, 플라스틱 및 목재를 포함하는 군에서 각각 독립적으로 서로 다르게 선택되는 이종 재질의 접착 전단 강도가 높을 수 있다.The one-component epoxy adhesive composition may have high adhesive shear strength of different materials independently selected from the group including metal, plastic, and wood, compared to the one-component epoxy adhesive composition that does not contain the epoxy adhesive additive. .
이하 본 발명의 실시예에 대해 상술한다. 다만, 하기에 기재된 실시예는 본 발명의 일부 실시 형태에 불과한 것으로서, 본 발명의 범위가 하기 실시예에 한정되는 것은 아니다. Hereinafter, embodiments of the present invention will be described in detail. However, the examples described below are merely some embodiments of the present invention, and the scope of the present invention is not limited to the following examples.
[실시예 1] 제1 에폭시 접착제용 첨가제의 제조[Example 1] Preparation of additives for first epoxy adhesive
에폭시로 1,6-헥산디올 유래 디글리시딜 에테르(제1 에폭시) 및 비스페놀 A 유래 디글리시딜 에테르(제2 에폭시)를 준비하였다. 말레인화 폴리부타디엔으로 Ricon® l30MA20을 준비하였다. 폴리에테르 아민으로 SURFONAMINE® L-100을 준비하였다. Diglycidyl ether derived from 1,6-hexanediol (first epoxy) and diglycidyl ether derived from bisphenol A (second epoxy) were prepared as epoxy. Ricon® l30MA20 was prepared with maleinized polybutadiene. SURFONAMINE® L-100 was prepared as a polyether amine.
에폭시는 제1 에폭시를 30 중량%, 제2 에폭시를 70 중량% 혼합하였다. 에폭시, 말레인화 폴리부타디엔 및 폴리에테르 아민을 70:27:3의 중량비로 혼합하였다. 상기 혼합된 반응물을 120 ℃에서 2시간 반응하였다. 이로써 본 발명의 실시예에 따른 에폭시 접착제용 첨가제 중 제1 에폭시 접착제용 첨가제가 제조되었다.As for the epoxy, 30% by weight of the first epoxy and 70% by weight of the second epoxy were mixed. Epoxy, maleinized polybutadiene and polyether amine were mixed in a weight ratio of 70:27:3. The mixed reactants were reacted at 120 °C for 2 hours. Thus, a first additive for epoxy adhesive among additives for epoxy adhesive according to an embodiment of the present invention was prepared.
[실시예 2] 제2 에폭시 접착제용 첨가제의 제조[Example 2] Preparation of additives for second epoxy adhesive
에폭시로 1,6-헥산디올 유래 디글리시딜 에테르(제1 에폭시) 및 비스페놀 A 유래 디글리시딜 에테르(제2 에폭시)를 준비하였다. 말레인화 에틸렌으로 금강 MPE-50을 준비하였다. 용매로 메틸 에틸 케톤(MEK)을 준비하였다.Diglycidyl ether derived from 1,6-hexanediol (first epoxy) and diglycidyl ether derived from bisphenol A (second epoxy) were prepared as epoxy. Kumgang MPE-50 was prepared with maleinized ethylene. Methyl ethyl ketone (MEK) was prepared as a solvent.
에폭시는 제1 에폭시를 30 중량%, 제2 에폭시를 70 중량% 혼합하였다. 에폭시 및 말레인화 에틸렌을 70:30 중량비로 혼합하였다. 용매는 전체 중량의 40%가 되도록 혼합하였다. 상기 혼합된 반응물은 120 ℃에서 2시간 반응한 후, 진공으로 용매를 제거하였다. 이로써 본 발명의 실시예에 따른 에폭시 접착제용 첨가제 중 제2 에폭시 접착제용 첨가제가 제조되었다.As for the epoxy, 30% by weight of the first epoxy and 70% by weight of the second epoxy were mixed. Epoxy and maleinized ethylene were mixed in a 70:30 weight ratio. The solvent was mixed so as to be 40% of the total weight. The mixed reactants were reacted at 120 °C for 2 hours, and then the solvent was removed in vacuum. Thus, among the additives for epoxy adhesives according to the embodiment of the present invention, the second additive for epoxy adhesives was prepared.
[실시예 3-1] 일액형 에폭시 접착제 조성물의 제조[Example 3-1] Preparation of one-component epoxy adhesive composition
일액형 에폭시 접착제 조성물용 에폭시로 국도화학 YD 128을 준비하였다. 에폭시 접착제용 첨가제로 실시예 1에 따른 제1 에폭시 접착제용 첨가제를 준비하였다. 폴리머로 Huntsman DY-965을 준비하였다. 에폭시, 제1 에폭시 접착제용 첨가제 및 폴리머는 60:30:10의 중량비로 준비하였다.Kukdo Chemical YD 128 was prepared as an epoxy for a one-component epoxy adhesive composition. As an additive for an epoxy adhesive, a first additive for an epoxy adhesive according to Example 1 was prepared. Huntsman DY-965 was prepared as a polymer. Epoxy, the additive for the first epoxy adhesive, and the polymer were prepared in a weight ratio of 60:30:10.
별도의 첨가제로 실리카 및 실란을 준비하였다. 촉매로 Evonik dicyandiamide(DICY)를 준비하였다. 실리카는 5 phr, 실란은 1 phr, 촉매는 2.5 phr 첨가하였다. 상기 반응물을 혼합하여 본 발명의 실시예에 따른 일액형 에폭시 접착제 조성물을 제조하였다.Silica and silane were prepared as separate additives. Evonik dicyandiamide (DICY) was prepared as a catalyst. 5 phr of silica, 1 phr of silane, and 2.5 phr of catalyst were added. The reactants were mixed to prepare a one-component epoxy adhesive composition according to an embodiment of the present invention.
[실시예 3-2] 일액형 에폭시 접착제 조성물의 제조[Example 3-2] Preparation of one-component epoxy adhesive composition
일액형 에폭시 접착제 조성물용 에폭시로 국도화학 YD 128을 준비하였다. 에폭시 접착제용 첨가제로 실시예 2에 따른 제2 에폭시 접착제용 첨가제를 준비하였다. 폴리머로 Huntsman DY-965을 준비하였다. 에폭시, 제2 에폭시 접착제용 첨가제 및 폴리머는 60:30:10의 중량비로 준비하였다.Kukdo Chemical YD 128 was prepared as an epoxy for a one-component epoxy adhesive composition. As an additive for epoxy adhesive, a second additive for epoxy adhesive according to Example 2 was prepared. Huntsman DY-965 was prepared as a polymer. Epoxy, the additive for the second epoxy adhesive, and the polymer were prepared in a weight ratio of 60:30:10.
별도의 첨가제로 실리카 및 실란을 준비하였다. 촉매로 Evonik dicyandiamide(DICY)를 준비하였다. 실리카는 5 phr, 실란은 1 phr, 촉매는 2.5 phr 첨가하였다. 상기 반응물을 혼합하여 본 발명의 실시예에 따른 일액형 에폭시 접착제 조성물을 제조하였다.Silica and silane were prepared as separate additives. Evonik dicyandiamide (DICY) was prepared as a catalyst. 5 phr of silica, 1 phr of silane, and 2.5 phr of catalyst were added. The reactants were mixed to prepare a one-component epoxy adhesive composition according to an embodiment of the present invention.
[실시예 3-3] 일액형 에폭시 접착제 조성물의 제조[Example 3-3] Preparation of one-component epoxy adhesive composition
일액형 에폭시 접착제 조성물용 에폭시로 국도화학 YD 128을 준비하였다. 에폭시 접착제용 첨가제로 실시예 1 및 2에 따른 제1 및 제2 에폭시 접착제용 첨가제를 모두 준비하였다. 폴리머로 Huntsman DY-965을 준비하였다. 에폭시, 제1 에폭시 접착제용 첨가제, 제2 에폭시 접착제용 첨가제 및 폴리머는 30:30:30:10의 중량비로 준비하였다.Kukdo Chemical YD 128 was prepared as an epoxy for a one-component epoxy adhesive composition. As additives for epoxy adhesives, the first and second additives for epoxy adhesives according to Examples 1 and 2 were both prepared. Huntsman DY-965 was prepared as a polymer. Epoxy, the additive for the first epoxy adhesive, the additive for the second epoxy adhesive, and the polymer were prepared in a weight ratio of 30:30:30:10.
별도의 첨가제로 실리카 및 실란을 준비하였다. 촉매로 Evonik dicyandiamide(DICY)를 준비하였다. 실리카는 5 phr, 실란은 1 phr, 촉매는 2.5 phr 첨가하였다. 상기 반응물을 혼합하여 본 발명의 실시예에 따른 일액형 에폭시 접착제 조성물을 제조하였다.Silica and silane were prepared as separate additives. Evonik dicyandiamide (DICY) was prepared as a catalyst. 5 phr of silica, 1 phr of silane, and 2.5 phr of catalyst were added. The reactants were mixed to prepare a one-component epoxy adhesive composition according to an embodiment of the present invention.
[실시예 3-4] 일액형 에폭시 접착제 조성물의 제조[Example 3-4] Preparation of one-component epoxy adhesive composition
실시예 3-3과 동일한 방법으로 일액형 에폭시 접착제 조성물을 제조하되, 에폭시, 제1 에폭시 접착제용 첨가제, 제2 에폭시 접착제용 첨가제 및 폴리머는 20:40:30:10의 중량비로 준비하였다.A one-component epoxy adhesive composition was prepared in the same manner as in Example 3-3, but the epoxy, the first epoxy adhesive additive, the second epoxy adhesive additive, and the polymer were prepared in a weight ratio of 20:40:30:10.
[실시예 3-5] 일액형 에폭시 접착제 조성물의 제조[Example 3-5] Preparation of one-component epoxy adhesive composition
실시예 3-3과 동일한 방법으로 일액형 에폭시 접착제 조성물을 제조하되, 에폭시, 제1 에폭시 접착제용 첨가제, 제2 에폭시 접착제용 첨가제 및 폴리머는 20:30:40:10의 중량비로 준비하였다.A one-component epoxy adhesive composition was prepared in the same manner as in Example 3-3, but the epoxy, the first epoxy adhesive additive, the second epoxy adhesive additive, and the polymer were prepared in a weight ratio of 20:30:40:10.
[실시예 3-6] 일액형 에폭시 접착제 조성물의 제조[Example 3-6] Preparation of one-component epoxy adhesive composition
실시예 3-3과 동일한 방법으로 일액형 에폭시 접착제 조성물을 제조하되, 에폭시, 제1 에폭시 접착제용 첨가제, 제2 에폭시 접착제용 첨가제 및 폴리머는 10:40:40:10의 중량비로 준비하였다.A one-component epoxy adhesive composition was prepared in the same manner as in Example 3-3, but the epoxy, the first epoxy adhesive additive, the second epoxy adhesive additive, and the polymer were prepared in a weight ratio of 10:40:40:10.
[비교예 1] 첨가제가 없는 일액형 에폭시 접착제 조성물의 제조[Comparative Example 1] Preparation of additive-free one-component epoxy adhesive composition
일액형 에폭시 접착제 조성물용 에폭시로 국도화학 YD 128을 준비하였다. 폴리머로 Huntsman DY-965을 준비하였다. 에폭시 및 폴리머는 90:10의 중량비로 준비하였다.Kukdo Chemical YD 128 was prepared as an epoxy for a one-component epoxy adhesive composition. Huntsman DY-965 was prepared as a polymer. Epoxy and polymer were prepared in a weight ratio of 90:10.
별도의 첨가제로 실리카 및 실란을 준비하였다. 촉매로 Evonik dicyandiamide(DICY)를 준비하였다. 실리카는 5 phr, 실란은 1 phr, 촉매는 2.5 phr 첨가하였다. 상기 반응물을 혼합하여 본 발명의 비교예에 따른 일액형 에폭시 접착제 조성물을 제조하였다.Silica and silane were prepared as separate additives. Evonik dicyandiamide (DICY) was prepared as a catalyst. 5 phr of silica, 1 phr of silane, and 2.5 phr of catalyst were added. The reactants were mixed to prepare a one-component epoxy adhesive composition according to a comparative example of the present invention.
상기 실시예 3-1 내지 3-6 및 비교예 1에 따라 제조된 일액형 에폭시 접착제 조성물의 조성을 요약하면 하기 표 1과 같다.The composition of the one-component epoxy adhesive composition prepared according to Examples 3-1 to 3-6 and Comparative Example 1 is summarized in Table 1 below.
실시 3-1Implementation 3-1 실시 3-2Implementation 3-2 실시 3-3Implementation 3-3 실시 3-4Implementation 3-4 실시 3-5Implementation 3-5 실시 3-6Implementation 3-6 비교 1Compare 1
에폭시epoxy 6060 6060 3030 2020 2020 1010 9090
제1 첨가제1st additive 3030 -- 3030 4040 3030 4040 --
제2 첨가제2nd additive -- 3030 3030 3030 4040 4040 --
폴리머polymer 1010 1010 1010 1010 1010 1010 1010
실리카silica 5 phr5 phr 5 phr5 phr 5 phr5 phr 5 phr5 phr 5 phr5 phr 5 phr5 phr 5 phr5 phr
실란Silane 1 phr1 phr 1 phr1 phr 1 phr1 phr 1 phr1 phr 1 phr1 phr 1 phr1 phr 1 phr1 phr
촉매catalyst 2.5 phr2.5 phr 2.5 phr2.5 phr 2.5 phr2.5 phr 2.5 phr2.5 phr 2.5 phr2.5 phr 2.5 phr2.5 phr 2.5 phr2.5 phr
[실험예 1] 이종 접착 전단 강도의 측정[Experimental Example 1] Measurement of heterogeneous adhesive shear strength
이종 접착 전단 강도 측정을 위해 SUS 및 HDPE의 시험편을 준비하였다. 각 시험편은 100 mm × 25 mm의 크기로 준비되었다. 양 시험편은 길이 방향으로 12.7 mm 가 겹치도록 배치되어, 겹친 부분에 실시예 3-1 내지 3-6 및 비교예 1에 따른 에폭시 접착제 조성물을 0.2 mm 두께로 도포하였다. 양 시험편은 압력 지그를 사용하여 25 kgf/cm2의 압력을 가하고, 200 내지 220도에서 30분 간 경화하였다.Test pieces of SUS and HDPE were prepared for the measurement of heterogeneous adhesive shear strength. Each specimen was prepared with a size of 100 mm × 25 mm. Both test pieces were arranged to overlap each other by 12.7 mm in the longitudinal direction, and the epoxy adhesive composition according to Examples 3-1 to 3-6 and Comparative Example 1 was applied to the overlapping portion to a thickness of 0.2 mm. Both test pieces were cured at 200 to 220 degrees for 30 minutes by applying a pressure of 25 kgf/cm 2 using a pressure jig.
Figure PCTKR2022016780-appb-img-000029
Figure PCTKR2022016780-appb-img-000029
상기와 같이 준비된 시험편을 UTM에 장착 후 ASTM D 1002 규격대로 분당 10 mm의 속도로 전단 강도를 실험하였다. 상기 실험 결과는 하기 표 2와 같다.After mounting the test piece prepared as described above in the UTM, shear strength was tested at a speed of 10 mm per minute according to ASTM D 1002 standard. The experimental results are shown in Table 2 below.
실시 3-1Implementation 3-1 실시 3-2Implementation 3-2 실시 3-3Implementation 3-3 실시 3-4Implementation 3-4 실시 3-5Implementation 3-5 실시 3-6Implementation 3-6 비교 1Compare 1
에폭시epoxy 6060 6060 3030 2020 2020 1010 9090
제1 첨가제1st additive 3030 -- 3030 4040 3030 4040 --
제2 첨가제2nd additive -- 3030 3030 3030 4040 4040 --
폴리머polymer 1010 1010 1010 1010 1010 1010 1010
실리카silica 5 phr5 phr 5 phr5 phr 5 phr5 phr 5 phr5 phr 5 phr5 phr 5 phr5 phr 5 phr5 phr
실란Silane 1 phr1 phr 1 phr1 phr 1 phr1 phr 1 phr1 phr 1 phr1 phr 1 phr1 phr 1 phr1 phr
촉매catalyst 2.5 phr2.5 phr 2.5 phr2.5 phr 2.5 phr2.5 phr 2.5 phr2.5 phr 2.5 phr2.5 phr 2.5 phr2.5 phr 2.5 phr2.5 phr
전단강도shear strength
(MPa)(MPa)
5.35.3 6.46.4 7.57.5 7.47.4 8.28.2 7.77.7 2.32.3
표 2의 비교예 1 및 실시예 3-1, 3-2를 참조하면, 본 발명의 실시예 1에 따른 제1 에폭시 접착제용 첨가제 또는 본 발명의 실시예 2에 따른 제2 에폭시 접착제용 첨가제 중 하나가 첨가된 일액형 에폭시 접착제 조성물은 2배 이상의 이종 소재 접착 강도를 가짐을 확인할 수 있다.표 2의 실시예3-1 내지 3-5를 참조하면, 본 발명의 실시예 1에 따른 제1 에폭시 접착제용 첨가제 및 본 발명의 실시예 2에 따른 제2 에폭시 접착제용 첨가제가 모두 첨가된 일액형 에폭시 접착제 조성물은 상기 본 발명의 실시예 1에 따른 제1 에폭시 접착제용 첨가제 또는 본 발명의 실시예 2에 따른 제2 에폭시 접착제용 첨가제 중 하나가 첨가된 일액형 에폭시 접착제 조성물보다도 다소 강한 이종 소재 접착 강도를 가짐을 확인할 수 있다.Referring to Comparative Example 1 and Examples 3-1 and 3-2 of Table 2, among the first epoxy adhesive additive according to Example 1 of the present invention or the second epoxy adhesive additive according to Example 2 of the present invention It can be seen that the one-component epoxy adhesive composition to which one is added has two or more times the bonding strength of different materials. Referring to Examples 3-1 to 3-5 in Table 2, the first The one-component epoxy adhesive composition to which both the additive for epoxy adhesive and the additive for second epoxy adhesive according to Example 2 of the present invention are added is the first additive for epoxy adhesive according to Example 1 of the present invention or the embodiment of the present invention. It can be seen that the adhesive strength of the second epoxy adhesive according to 2 is somewhat stronger than that of the one-component epoxy adhesive composition to which one of the additives for epoxy adhesive is added.
한편, 표 2의 실시예 3-6을 참조하면, 본 발명의 실시예 1에 따른 제1 에폭시 접착제용 첨가제 및 본 발명의 실시예 2에 따른 제2 에폭시 접착제용 첨가제가 일정 수준 이상의 함량을 가지는 경우, 이종 소재 접착 강도가 다시 다소 감소함을 확인할 수 있다. 이는 본 발명의 실시예에 따른 에폭시 접착제용 첨가제가 소수성을 가지는 소재 접착에 기여하나, 함량이 일정 수준 이상 증가하는 경우 극성을 가지는 소재에 대한 접착 강도가 감소하기 때문이다.On the other hand, referring to Examples 3-6 of Table 2, the first epoxy adhesive additive according to Example 1 of the present invention and the second epoxy adhesive additive according to Example 2 of the present invention have a content of a certain level or more In this case, it can be confirmed that the adhesive strength of the different materials is slightly reduced again. This is because the additive for epoxy adhesive according to the embodiment of the present invention contributes to the adhesion of materials having hydrophobicity, but the adhesive strength to materials having polarity decreases when the content increases above a certain level.
상기에서는 본 발명의 바람직한 실시예를 참조하여 설명하였지만, 해당 기술 분야의 숙련된 당업자는 하기의 특허 청구 범위에 기재된 본 발명의 사상 및 영역으로부터 벗어나지 않는 범위 내에서 본 발명을 다양하게 수정 및 변경시킬 수 있음을 이해할 수 있을 것이다.Although the above has been described with reference to preferred embodiments of the present invention, those skilled in the art can variously modify and change the present invention without departing from the spirit and scope of the present invention described in the claims below. You will understand that you can.

Claims (15)

  1. 하기 화학식(Ⅰ)을 가지는,Having the following formula (I),
    에폭시 접착제용 첨가제:Additives for Epoxy Adhesives:
    Figure PCTKR2022016780-appb-img-000030
    (Ⅰ)
    Figure PCTKR2022016780-appb-img-000030
    (Ⅰ)
    여기서,here,
    X는 폴리에테르(polyether) 작용기이고,X is a polyether functional group,
    Y는 폴리부타디엔(polybutadiene) 작용기이며,Y is a polybutadiene functional group,
    Z는 사슬형, 분지된 사슬형 탄화수소 및 하나 이상의 방향족 고리를 포함하는 탄화수소 중 하나 이상으로 선택되는 작용기이고,Z is a functional group selected from one or more of chain-like, branched-chain hydrocarbons and hydrocarbons containing one or more aromatic rings;
    n은 1 내지 100의 정수이다.n is an integer from 1 to 100;
  2. 제1항에 있어서,According to claim 1,
    상기 X는 하기 화학식(Ⅱ)를 가지는 작용기인,Wherein X is a functional group having the following formula (II),
    에폭시 접착제용 첨가제:Additives for Epoxy Adhesives:
    Figure PCTKR2022016780-appb-img-000031
    (Ⅱ)
    Figure PCTKR2022016780-appb-img-000031
    (II)
    여기서,here,
    r은 1 내지 100의 정수이고,r is an integer from 1 to 100;
    s는 1 내지 100의 정수이며,s is an integer from 1 to 100,
    r은 s보다 크다.r is greater than s.
  3. 제1항에 있어서,According to claim 1,
    상기 Z는 하기 화학식(Ⅲ)을 가지는 작용기 및 하기 화학식(Ⅳ)을 가지는 작용기 중 하나 이상으로 선택되는 작용기인,Wherein Z is a functional group selected from at least one of a functional group having the following formula (III) and a functional group having the following formula (IV),
    에폭시 접착제용 첨가제:Additives for Epoxy Adhesives:
    Figure PCTKR2022016780-appb-img-000032
    (Ⅲ)
    Figure PCTKR2022016780-appb-img-000032
    (III)
    Figure PCTKR2022016780-appb-img-000033
    (Ⅳ)
    Figure PCTKR2022016780-appb-img-000033
    (IV)
    여기서,here,
    q는 1 내지 100의 정수이다.q is an integer from 1 to 100;
  4. 제3항에 있어서,According to claim 3,
    상기 화학식(Ⅲ)을 가지는 작용기 및 상기 화학식(Ⅳ)을 가지는 작용기의 중량비는 2:8 내지 4:6인 것을 특징으로 하는,Characterized in that the weight ratio of the functional group having the formula (III) and the functional group having the formula (IV) is 2:8 to 4:6,
    에폭시 접착제용 첨가제.Additives for epoxy adhesives.
  5. 제1항에 있어서,According to claim 1,
    상기 에폭시 접착제용 첨가제는,The additive for the epoxy adhesive,
    하기 화학식(Ⅴ)을 가지는 화합물, 하기 화학식(Ⅵ)을 가지는 화합물, 하기 화학식(Ⅶ)을 가지는 화합물 및 하기 화학식(ⅤⅢ)을 가지는 화합물을 반응하여 수득되는 것을 특징으로 하는,Characterized in that it is obtained by reacting a compound having the following formula (V), a compound having the following formula (VI), a compound having the following formula (VII), and a compound having the following formula (VIII),
    에폭시 접착제용 첨가제:Additives for Epoxy Adhesives:
    Figure PCTKR2022016780-appb-img-000034
    (Ⅴ)
    Figure PCTKR2022016780-appb-img-000034
    (V)
    Figure PCTKR2022016780-appb-img-000035
    (Ⅵ)
    Figure PCTKR2022016780-appb-img-000035
    (VI)
    Figure PCTKR2022016780-appb-img-000036
    (Ⅶ)
    Figure PCTKR2022016780-appb-img-000036
    (VII)
    Figure PCTKR2022016780-appb-img-000037
    (ⅤⅢ)
    Figure PCTKR2022016780-appb-img-000037
    (ⅤⅢ)
    여기서,here,
    q는 1 내지 100의 정수이고,q is an integer from 1 to 100;
    r은 1 내지 100의 정수이며,r is an integer from 1 to 100;
    s는 1 내지 100의 정수이다.s is an integer from 1 to 100.
  6. 제5항에 있어서,According to claim 5,
    상기 화학식(Ⅴ)을 가지는 화합물과 상기 화학식(Ⅵ)을 가지는 화합물의 중량비는 2:8 내지 4:6인 것을 특징으로 하는,Characterized in that the weight ratio of the compound having the formula (V) and the compound having the formula (VI) is 2:8 to 4:6,
    에폭시 접착제용 첨가제.Additives for epoxy adhesives.
  7. 제6항에 있어서,According to claim 6,
    상기 에폭시 접착제용 첨가제 총 중량에 대하여,With respect to the total weight of the additive for the epoxy adhesive,
    상기 화학식(Ⅴ)을 가지는 화합물과 상기 화학식(Ⅵ)을 가지는 화합물의 총 중량은 60 내지 80 중량% 이고,The total weight of the compound having formula (V) and the compound having formula (VI) is 60 to 80% by weight,
    상기 화학식(Ⅶ)을 가지는 화합물의 중량은 25 내지 35 중량% 이며,The weight of the compound having formula (VII) is 25 to 35% by weight,
    상기 화학식(ⅤⅢ)을 가지는 화합물의 중량은 2 내지 5 중량% 인 것을 특징으로 하는,Characterized in that the weight of the compound having the formula (VIII) is 2 to 5% by weight,
    에폭시 접착제용 첨가제.Additives for epoxy adhesives.
  8. 하기 화학식(Ⅸ)를 가지는,Having the following formula (IX),
    에폭시 접착제용 첨가제:Additives for Epoxy Adhesives:
    Figure PCTKR2022016780-appb-img-000038
    (Ⅸ)
    Figure PCTKR2022016780-appb-img-000038
    (Ⅸ)
    여기서,here,
    Y'는 폴리에틸렌(polyethylene) 작용기이며,Y' is a polyethylene functional group,
    Z는 사슬형, 분지된 사슬형 탄화수소 및 하나 이상의 방향족 고리를 포함하는 탄화수소 중 하나 이상으로 선택되는 작용기이고,Z is a functional group selected from one or more of chain-like, branched-chain hydrocarbons and hydrocarbons containing one or more aromatic rings;
    n'은 1 내지 100의 정수이다.n' is an integer from 1 to 100;
  9. 제8항에 있어서,According to claim 8,
    상기 Z는 하기 화학식(Ⅲ)을 가지는 작용기 및 하기 화학식(Ⅳ)을 가지는 작용기 중 하나 이상으로 선택되는 작용기인,Wherein Z is a functional group selected from at least one of a functional group having the following formula (III) and a functional group having the following formula (IV),
    에폭시 접착제용 첨가제:Additives for Epoxy Adhesives:
    Figure PCTKR2022016780-appb-img-000039
    (Ⅲ)
    Figure PCTKR2022016780-appb-img-000039
    (III)
    Figure PCTKR2022016780-appb-img-000040
    (Ⅳ)
    Figure PCTKR2022016780-appb-img-000040
    (IV)
    여기서,here,
    q는 1 내지 100의 정수이다.q is an integer from 1 to 100;
  10. 제9항에 있어서,According to claim 9,
    상기 화학식(Ⅲ)을 가지는 작용기 및 상기 화학식(Ⅳ)을 가지는 작용기의 중량비는 2:8 내지 4:6인 것을 특징으로 하는,Characterized in that the weight ratio of the functional group having the formula (III) and the functional group having the formula (IV) is 2:8 to 4:6,
    에폭시 접착제용 첨가제.Additives for epoxy adhesives.
  11. 제8항에 있어서,According to claim 8,
    상기 에폭시 접착제용 첨가제는,The additive for the epoxy adhesive,
    하기 화학식(Ⅴ)을 가지는 화합물, 하기 화학식(Ⅵ)을 가지는 화합물 및 하기 화학식(Ⅹ)을 반응하여 수득되는 것을 특징으로 하는,Characterized in that it is obtained by reacting a compound having the following formula (V), a compound having the following formula (VI) and the following formula (X),
    에폭시 접착제용 첨가제:Additives for Epoxy Adhesives:
    Figure PCTKR2022016780-appb-img-000041
    (Ⅴ)
    Figure PCTKR2022016780-appb-img-000041
    (V)
    Figure PCTKR2022016780-appb-img-000042
    (Ⅵ)
    Figure PCTKR2022016780-appb-img-000042
    (VI)
    Figure PCTKR2022016780-appb-img-000043
    (Ⅹ)
    Figure PCTKR2022016780-appb-img-000043
    (X)
    여기서,here,
    q는 1 내지 100의 정수이다.q is an integer from 1 to 100;
  12. 제11항에 있어서,According to claim 11,
    상기 화학식(Ⅴ)을 가지는 화합물과 상기 화학식(Ⅵ)을 가지는 화합물의 중량비는 2:8 내지 4:6인 것을 특징으로 하는,Characterized in that the weight ratio of the compound having the formula (V) and the compound having the formula (VI) is 2:8 to 4:6,
    에폭시 접착제용 첨가제.Additives for epoxy adhesives.
  13. 제12항에 있어서,According to claim 12,
    상기 에폭시 접착제용 첨가제 총 중량에 대하여,With respect to the total weight of the additive for the epoxy adhesive,
    상기 화학식(Ⅴ)을 가지는 화합물과 상기 화학식(Ⅵ)을 가지는 화합물의 총 중량은 60 내지 80 중량% 이고,The total weight of the compound having formula (V) and the compound having formula (VI) is 60 to 80% by weight,
    상기 화학식(Ⅹ)을 가지는 화합물의 중량은 20 내지 40 중량% 인 것을 특징으로 하는,Characterized in that the weight of the compound having formula (X) is 20 to 40% by weight,
    에폭시 접착제용 첨가제.Additives for epoxy adhesives.
  14. 제1항에 따른 에폭시 접착제용 첨가제 및 제8항에 따른 에폭시 접착제용 첨가제 중 하나 이상의 에폭시 접착제용 첨가제;an additive for an epoxy adhesive of at least one of the additive for an epoxy adhesive according to claim 1 and the additive for an epoxy adhesive according to claim 8;
    폴리프로필렌 글리콜(polypropylene glycol; PPG) 및 폴리테트라메틸렌에테르 글리콜(polytetramethyleneether glycol; PTMEG) 중 하나 이상의 폴리머; 및polymers of at least one of polypropylene glycol (PPG) and polytetramethyleneether glycol (PTMEG); and
    디사이안디아마이드(dicyandiamide; DICY) 및 이미다졸(imidazole) 중 하나 이상의 촉매;를 포함하는,At least one catalyst of dicyandiamide (DICY) and imidazole;
    일액형 에폭시 접착제 조성물.A one component epoxy adhesive composition.
  15. 제14항에 있어서,According to claim 14,
    상기 일액형 에폭시 접착제 조성물은 상기 에폭시 접착제용 첨가제를 포함하지 않는 일액형 에폭시 접착제 조성물에 비해 금속, 플라스틱 및 목재를 포함하는 군에서 각각 독립적으로 서로 다르게 선택되는 이종 재질의 접착 전단 강도가 높은 것을 특징으로 하는,The one-component epoxy adhesive composition has a high adhesive shear strength of different materials independently selected from the group including metal, plastic, and wood, compared to the one-component epoxy adhesive composition that does not contain the additive for epoxy adhesive. to do,
    일액형 에폭시 접착제 조성물.A one component epoxy adhesive composition.
PCT/KR2022/016780 2021-12-20 2022-10-31 Additive for epoxy adhesive and one-component epoxy adhesive composition comprising same WO2023120946A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR1020210182335A KR102576956B1 (en) 2021-12-20 2021-12-20 Epoxy adhesive additive and one-component epoxy adhesive composition comprising the same
KR10-2021-0182335 2021-12-20

Publications (1)

Publication Number Publication Date
WO2023120946A1 true WO2023120946A1 (en) 2023-06-29

Family

ID=86902928

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2022/016780 WO2023120946A1 (en) 2021-12-20 2022-10-31 Additive for epoxy adhesive and one-component epoxy adhesive composition comprising same

Country Status (2)

Country Link
KR (1) KR102576956B1 (en)
WO (1) WO2023120946A1 (en)

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002235049A (en) * 2001-02-09 2002-08-23 Mitsubishi Plastics Ind Ltd Adhesive sheet, sheet for filler of solar cell and solar cell using the same
US20030187154A1 (en) * 2000-04-10 2003-10-02 Rainer Schoenfeld Impact-resistant epoxy resin compositions
KR101893690B1 (en) * 2017-05-12 2018-08-31 부산대학교 산학협력단 Additive using epoxy adhesive and composition for structural epoxy adhesive including the additive
KR20180124464A (en) * 2017-05-12 2018-11-21 부산대학교 산학협력단 Structural adhesive composition having high elongation and impact-resistance

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20030187154A1 (en) * 2000-04-10 2003-10-02 Rainer Schoenfeld Impact-resistant epoxy resin compositions
JP2002235049A (en) * 2001-02-09 2002-08-23 Mitsubishi Plastics Ind Ltd Adhesive sheet, sheet for filler of solar cell and solar cell using the same
KR101893690B1 (en) * 2017-05-12 2018-08-31 부산대학교 산학협력단 Additive using epoxy adhesive and composition for structural epoxy adhesive including the additive
KR20180124464A (en) * 2017-05-12 2018-11-21 부산대학교 산학협력단 Structural adhesive composition having high elongation and impact-resistance

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
HA THU HUONG, JANG JIN YOUNG, CHO YOUN BOK, JEONG HAN MO, KIM BYUNG KYU: "Maleic anhydride grafted polyethylene powder coated with epoxy resin: A novel reactive hot melt adhesive", JOURNAL OF APPLIED POLYMER SCIENCE, JOHN WILEY & SONS, INC., US, vol. 116, no. 1, 5 April 2010 (2010-04-05), US , pages 328 - 332, XP093074021, ISSN: 0021-8995, DOI: 10.1002/app.31576 *
LUO ZHU, CHEN WEILONG, JIN ZHONG, DONG FUPING, YANG LE, ZHENG QIANG: "Epoxy resin modified maleic anhydride-grafted-liquid polybutadiene on the properties of short aramid fiber reinforced natural rubber composite", POLYMER COMPOSITES, SOCIETY OF PLASTICS ENGINEERS, INC., US, vol. 39, no. S4, 1 December 2018 (2018-12-01), US , pages E2006 - E2015, XP093074016, ISSN: 0272-8397, DOI: 10.1002/pc.24397 *

Also Published As

Publication number Publication date
KR20230093582A (en) 2023-06-27
KR102576956B1 (en) 2023-09-08

Similar Documents

Publication Publication Date Title
CN107406741B (en) Semiconductor device and image sensor module
US5200494A (en) One-pack type epoxide composition
WO2017078449A1 (en) Two liquid type epoxy adhesive composition
WO2023120946A1 (en) Additive for epoxy adhesive and one-component epoxy adhesive composition comprising same
WO2019156326A1 (en) Solvent-free coating composition
WO2019208954A1 (en) Epoxy functional acrylate resin compound capable of uv and heat curing, method for preparing same, and curable resin composition
WO2022139338A1 (en) Electrical steel sheet, and electrical steel sheet laminate
WO2018208072A1 (en) Structural adhesive composition having high elongation and impact resistance
WO2010038943A2 (en) Resin composition for cation electrodeposition paint with excellent inner permeability, containing aromatic sulfonic acid and urethane functional rheology modifier
WO2021054513A1 (en) Method for producing polyimide powder, and polyimide powder produced thereby
WO2022025554A1 (en) Monoamine compound for synthesizing emulsifier
WO2023121073A1 (en) Gemini-type epoxy resin emulsifier and method for preparing same
WO2021118233A1 (en) Bismaleimide-derived epoxy compound containing polycyclic structure and preparation method therefor
EP1070733A1 (en) Method of synthesis of polyaminofunctional hydroxyurethane oligomers and hybride polymers formed therefrom
WO2017200339A1 (en) Epoxy compound, preparation method therefor, and epoxy composition using same
WO2022139332A1 (en) Adhesive coating composition for electrical steel sheet, electrical steel sheet laminate, and method for manufacturing same
WO2022139351A1 (en) Electrical steel sheet and laminate thereof
WO2022071713A1 (en) Resin composition
WO2020117009A1 (en) Polyurethane resin composition
WO2024136114A1 (en) Adhesive coating composition for electrical steel sheet, electrical steel sheet laminate, and method for manufacturing same
WO2021177586A1 (en) Primer composition for glass adhesive
WO2021015443A1 (en) Urethane adhesive composition
WO2022139328A1 (en) Adhesive coating composition for electrical steel sheet, electrical steel sheet laminate and manufacturing method therefor
WO2022173088A1 (en) Additive for epoxy adhesive, and structural epoxy adhesive composition comprising same
CN115637125B (en) Environment-friendly epoxy resin adhesive and preparation method thereof

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 22911584

Country of ref document: EP

Kind code of ref document: A1