KR102453940B1 - Method for producing an epoxy resin composition using an anhydride curing agent - Google Patents
Method for producing an epoxy resin composition using an anhydride curing agent Download PDFInfo
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- KR102453940B1 KR102453940B1 KR1020210180869A KR20210180869A KR102453940B1 KR 102453940 B1 KR102453940 B1 KR 102453940B1 KR 1020210180869 A KR1020210180869 A KR 1020210180869A KR 20210180869 A KR20210180869 A KR 20210180869A KR 102453940 B1 KR102453940 B1 KR 102453940B1
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates 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
- C08G59/18—Macromolecules 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
- C08G59/40—Macromolecules 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
- C08G59/50—Amines
- C08G59/56—Amines together with other curing agents
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates 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
- C08G59/18—Macromolecules 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
- C08G59/40—Macromolecules 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
- C08G59/42—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates 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
- C08G59/18—Macromolecules 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
- C08G59/40—Macromolecules 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
- C08G59/50—Amines
- C08G59/5046—Amines heterocyclic
- C08G59/5053—Amines heterocyclic containing only nitrogen as a heteroatom
- C08G59/5073—Amines heterocyclic containing only nitrogen as a heteroatom having two nitrogen atoms in the ring
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Abstract
Description
본 발명은 무수물 경화 에폭시 조성물의 제조를 위해 촉진제로서 이미다졸 염을 이용한 제조방법에 관한 것으로, 더욱 상세하게는 고온에서의 반응성을 유지하도록 본 발명에 따른 1,2-Dimethyl-1H-이미다졸을 카르복실산 화합물과 혼합한 염을 촉진제로 사용하고 무수물을 경화제로 사용하여 에폭시 수지 조성물을 제조하는 방법을 개시한다.The present invention relates to a manufacturing method using an imidazole salt as an accelerator for the preparation of an anhydride-cured epoxy composition, and more particularly, 1,2-Dimethyl-1H-imidazole according to the present invention to maintain reactivity at high temperature. Disclosed is a method for preparing an epoxy resin composition using a salt mixed with a carboxylic acid compound as an accelerator and an anhydride as a curing agent.
에폭시 수지를 위한 경화제로서, 공지되어 있는 무수물은 일반적으로 에폭시 수지와 혼합할 때 허용가능한 점도 및 반응성을 가진다. 무수물을 사용하여 경화된 에폭시 수지는 일반적으로 높은 온도 안정성, 우수한 방사선 안정성 뿐만 아니라 그의 유리 전이 온도 초과에서의 유용한 물리적 및 전기적 특성을 나타낸다.As curing agents for epoxy resins, known anhydrides generally have acceptable viscosity and reactivity when mixed with epoxy resins. Epoxy resins cured with anhydrides generally exhibit high temperature stability, good radiation stability, as well as useful physical and electrical properties above their glass transition temperature.
무수물과 에폭시 수지의 반응은, 예를 들어, 경화 시간 및 온도, 촉진제의 사용여부 및 유형, 수지 내 히드록실기의 양, 무수물 대 에폭시의 비율 등 다수의 인자에 좌우된다. 무수물은 전형적으로 촉진제의 부재 하에서는 에폭시기와 반응이 어렵다.The reaction of the anhydride with the epoxy resin depends on a number of factors, including, for example, the curing time and temperature, the presence and type of accelerator used, the amount of hydroxyl groups in the resin, and the ratio of anhydride to epoxy. Anhydrides are typically difficult to react with epoxy groups in the absence of an accelerator.
전형적인 상업용 에폭시수지/무수물 조성물은 무수물 촉진제를 사용한다. 이들은 산성 또는 염기성 화합물이다. 산은 에테르화에 유리한 반면, 염기는 에스테르화에 유리하다. 최적의 무수물/에폭시 비 및 수지의 경화된 특성은 사용된 촉진제에 의해 결정된다. 3급 아민이 무수물 촉진제로서 통상적으로 사용된다.A typical commercial epoxy resin/anhydride composition uses an anhydride accelerator. These are acidic or basic compounds. Acids favor etherification, while bases favor esterification. The optimum anhydride/epoxy ratio and cured properties of the resin are determined by the accelerator used. Tertiary amines are commonly used as anhydride promoters.
이들 통상적인 아민은 벤질디메틸아민 (BDMA) 및 트리스(디메틸아미노-메틸)페놀, 트리에틸렌 디아민 (TEDA), N,N'-디메틸피페라진 및 2-(디메틸아미노메틸)페놀을 포함한다.These common amines include benzyldimethylamine (BDMA) and tris(dimethylamino-methyl)phenol, triethylene diamine (TEDA), N,N'-dimethylpiperazine and 2-(dimethylaminomethyl)phenol.
무수물 및 디시안디아미드를 사용하여 경화되는 에폭시 수지 조성물을 위한 촉진제로서 N-히드록시에틸 피페리딘 및 피페라지닐 화합물을 사용하는 것이 개시되어 있고, 니트릴 기와 함께 에테르 결합을 지니는 4급 암모늄 염이 마이크로웨이브 조사 하에 무수물 경화되는 에폭시 수지를 위한 촉진제로서 사용되었다는 것이 또한 개시되어 있으며, 고체 금속 아세틸아세토네이트가 경화제로서 사용될 수도 있다. 그러나, 이들 고체 금속 아세틸아세토네이트는 무수물에 의한 에폭시 수지의 효율적인 경화를 유발하도록 적절하게 분산될 수 없다는 단점을 갖는다. The use of N-hydroxyethyl piperidine and piperazinyl compounds as accelerators for epoxy resin compositions cured using anhydride and dicyandiamide is disclosed, wherein quaternary ammonium salts having ether linkages with nitrile groups are It is also disclosed that it has been used as an accelerator for epoxy resins that are anhydride cured under microwave irradiation, and solid metal acetylacetonates may also be used as curing agents. However, these solid metal acetylacetonates have the disadvantage that they cannot be adequately dispersed to cause efficient curing of the epoxy resin by the anhydride.
국내공개특허제2019-0035904호는 화합물은 1-메틸이미다졸, 2-메틸이미다졸, 2-에틸-4-메틸이미다졸, 2-이미다졸-1-일-숙신산 에스테르, 1-시아노에틸-2-운데실이미다졸륨 트리멜리테이트, 그의 에폭시-이미다졸 부가물, 및 그의 조합으로 이루어진 군으로부터 선택한 화합물을 사용하고 있지만 점도가 높아 가공성이 어려운 단점이 있다.Korean Patent Publication No. 2019-0035904 discloses that the compounds are 1-methylimidazole, 2-methylimidazole, 2-ethyl-4-methylimidazole, 2-imidazol-1-yl-succinic acid ester, 1- Although a compound selected from the group consisting of cyanoethyl-2-undecylimidazolium trimellitate, its epoxy-imidazole adduct, and combinations thereof is used, it has a disadvantage in that processability is difficult due to high viscosity.
특히 저반응성 에폭시 수지와의 우수한 고온 반응성과 함께, 물질의 낭비 및 혼합 시스템의 수고로움을 최소화함으로써 원료 비용에서의 상당한 절감을 제공하기 위한 개선된 잠재성을 갖는 에폭시 경화제, 뿐만 아니라 바람직한 물리적 특성을 갖는 경화된 에폭시 수지 조성물이 요구되고 있다.An epoxy curing agent with improved potential to provide significant savings in raw material costs by minimizing waste of material and laboriousness of mixing systems, along with excellent high temperature reactivity, particularly with low-reactivity epoxy resins, as well as desirable physical properties. A cured epoxy resin composition having
본 발명은 상기한 종래의 문제를 해결코자 제공하는 것으로, 급속 고온 경화, 예를 들어, 약 110℃ 내지 약 150℃의 온도에서 약 2시간의 기간 동안의 경화를 제공하는 이미다졸 염을 제공함으로써, 통상적인 무수물 촉진제와 연관된 문제를 해결한다. 본 발명에 따른 이미다졸 염 첨가제는 잠재성 경화제로서 기능하며, 주위 온도에서 무수물 경화제 및 에폭시 수지와 혼합되어 있을 때 저장 안정성을 연장시킬 뿐만 아니라 상승된 경화 온도로 가열될 때 급속 경화를 가능하게 한다. 추가로, 본 발명의 이미다졸 염은 사이클 시간을 단축시키며, 이에 의해 경화된 에폭시 수지 구성요소를 제조할 때 증가된 처리량을 제공할 수 있다.SUMMARY OF THE INVENTION The present invention provides an solution to the above conventional problems by providing an imidazole salt that provides rapid high temperature curing, for example, curing at a temperature of about 110° C. to about 150° C. for a period of about 2 hours. , solves the problems associated with conventional anhydride accelerators. The imidazole salt additive according to the present invention functions as a latent curing agent and enables rapid curing when heated to elevated curing temperatures as well as extending storage stability when mixed with an anhydride curing agent and epoxy resin at ambient temperature. . Additionally, the imidazole salts of the present invention can shorten cycle times, thereby providing increased throughput when preparing cured epoxy resin components.
본 발명에 따라 상기 목적을 이루기 위한 수단으로서, 하기 단계를 포함하는 경화된 에폭시 수지 생성물을 제조하는 방법을 제공한다.According to the present invention, as a means for achieving the above object, there is provided a method for producing a cured epoxy resin product comprising the following steps.
본 발명에 따라 무수물 기재 에폭시 수지 조성물을 위한 촉진제로서 사용하기 위한 이미다졸의 카르복실산 염을 제공한다. 본 발명의, 특정 이미다졸의 카르복실산 염은 잠재성 무수물 촉진제이며, 50℃ 초과의 개시 온도로 가열될 때 에폭시 수지 경화를 가능하게 한다. 본 발명에 따른 이미다졸 염은 약 50 내지 약 200℃ 범위의 개시 온도를 갖는 에폭시 수지 조성물을 수득하는데 사용될 수 있다. According to the present invention there is provided a carboxylic acid salt of imidazole for use as a promoter for anhydride-based epoxy resin compositions. The carboxylic acid salts of certain imidazoles of the present invention are latent anhydride promoters and allow curing of epoxy resins when heated to an onset temperature above 50°C. The imidazole salts according to the present invention can be used to obtain epoxy resin compositions having an onset temperature in the range of about 50 to about 200 °C.
본 발명에 따라, 상기 이미디졸 염은 1,2-Dimethyl-1H-이미다졸을 카르복실산 화합물과 혼합하여 제조한다.According to the present invention, the imidazole salt is prepared by mixing 1,2-Dimethyl-1H-imidazole with a carboxylic acid compound.
본 발명에 따라, 이미다졸 염 첨가제, 무수물 경화제 및 에폭시 수지로부터 제조된 에폭시 조성물은 코팅 배합물 기술분야의 통상의 기술자에게 널리 공지된 매우 다양한 성분, 예컨대 용매, 충전제, 안료, 안료 분산제, 레올로지 개질제, 요변성제, 유동 및 레벨링 보조제, 탈포제 등과 함께 배합할 수 있다.According to the present invention, an epoxy composition prepared from an imidazole salt additive, an anhydride curing agent and an epoxy resin can be prepared from a wide variety of components well known to those skilled in the art of coating formulations, such as solvents, fillers, pigments, pigment dispersants, rheology modifiers. , thixotropic agents, flow and leveling aids, defoaming agents, and the like.
실시예를 통해 본 발명을 상세히 설명하기로 한다. 본 발명에 따른 이미다졸 염은 에폭시 경화제 배합물을 수득하기 위해 적합한 무수물 경화제와 조합한다. 이미다졸 염 및 무수물 경화제는 임의의 적합한 방법, 예컨대 혼합, 1종의 다른 종으로의 펌핑, 1종의 다른 종으로의 진공 전달에 의해 및 주위 또는 압력 조건, 예를 들어, 약 0.1 Torr 내지 약 10 Torr의 압력하에 조합될 수 있다. 적합한 무수물 경화제의 예는 선형 중합체성 무수물, 예컨대 폴리세바스산 및 폴리아젤라산 무수물; 지환족 무수물, 예컨대 메틸테트라히드로프탈산 무수물, 테트라히드로 프탈산 무수물, 메틸 나드산 무수물, 헥사히드로 프탈산 무수물 및 메틸헥사히드로 프탈산 무수물; 단순 지환족 무수물, 예컨대 숙신산 무수물, 치환된 숙신산 무수물, 시트르산 무수물, 말레산 무수물 및 말레산 무수물의 특수한 부가물, 도데실 숙신산 무수물, 말레산 무수물 비닐 및 말레산 무수물의 스티렌 공중합체, 다중-고리 지환 족 무수물 및 방향족 무수물, 예컨대 프탈산 무수물 및 트리멜리트산 무수물을 포함하나 이에 제한되지는 않는다. 적합한 무수물 촉진제의 예는 또한 이무수물, 예컨대 피로멜리트산 이무수물 (PMDA) 및 3,3', 4,4'-벤조페논-테트라카르복실산 이무수물 (BTDA)을 포함한다. 이미다졸 염은 경화제 100부당 약 1 내지 약 40부, 약 1 내지 약 20부; 및 일부 경우에는 약 1 내지 약 10부의 비로 무수물 경화제와 조합될 수 있다. 본 개시내용에 따른 에폭시 경화제는 에폭시의 당량당 약 0.8 내지 약 1.1 당량, 약 1.0 내지 약 1.0 및 일부 경우에는 약 0.95 내지 약 1.05 당량의 무수물 경화제를 함유할 수 있다.The present invention will be described in detail by way of Examples. The imidazole salt according to the invention is combined with a suitable anhydride curing agent to obtain an epoxy curing agent formulation. The imidazole salt and anhydride curing agent can be prepared by any suitable method, such as mixing, pumping to one other species, transferring vacuum to one other species, and under ambient or pressure conditions, e.g., from about 0.1 Torr to about 0.1 Torr. It can be combined under a pressure of 10 Torr. Examples of suitable anhydride curing agents include linear polymeric anhydrides such as polysebacic acid and polyazelaic anhydride; alicyclic anhydrides such as methyltetrahydrophthalic anhydride, tetrahydrophthalic anhydride, methyl nadic anhydride, hexahydrophthalic anhydride and methylhexahydrophthalic anhydride; Simple cycloaliphatic anhydrides such as succinic anhydride, substituted succinic anhydride, citric anhydride, maleic anhydride and special adducts of maleic anhydride, dodecyl succinic anhydride, styrene copolymer of maleic anhydride vinyl and maleic anhydride, multi-ring alicyclic and aromatic anhydrides such as phthalic anhydride and trimellitic anhydride. Examples of suitable anhydride accelerators also include dianhydrides such as pyromellitic dianhydride (PMDA) and 3,3', 4,4'-benzophenone-tetracarboxylic dianhydride (BTDA). The imidazole salt may be present in an amount of from about 1 to about 40 parts, from about 1 to about 20 parts per 100 parts curing agent; and in some cases from about 1 to about 10 parts of the anhydride curing agent. Epoxy curing agents according to the present disclosure may contain from about 0.8 to about 1.1 equivalents, from about 1.0 to about 1.0 and in some cases from about 0.95 to about 1.05 equivalents of anhydride curing agent per equivalent of epoxy.
상기 본 발명에 따라 사용하는 1,2-디메틸-1H-이미다졸은 밀도가 0.99g/cm3, 녹는점 20 ~ 40℃, 및 끓는점 205℃의 물성을 가지고 있기 때문에 이미다졸 염을 생성하는데 적합하다.Since the 1,2-dimethyl-1H-imidazole used according to the present invention has physical properties of a density of 0.99 g/cm 3 , a melting point of 20 to 40° C., and a boiling point of 205° C., it is suitable for producing an imidazole salt. .
1,2-디메틸-1H-이미다졸 (1 몰)을 자기 교반기 및 질소 유입구 및 열전쌍이 장착된 3구 둥근 바닥 플라스크에 충전하였다. 아세트산 (1 몰)을, 온도가 25-35℃에서 유지되도록 서서히 첨가하였다. 첨가가 완료되면, 혼합물을 실온으로 냉각시키고, 상용성 및 승온 반응성 연구에 사용하였다.1,2-Dimethyl-1H-imidazole (1 mole) was charged to a three necked round bottom flask equipped with a magnetic stirrer and nitrogen inlet and thermocouple. Acetic acid (1 mole) was added slowly such that the temperature was maintained at 25-35°C. Upon completion of the addition, the mixture was cooled to room temperature and used for compatibility and elevated temperature reactivity studies.
본 발명에 따라, 1,2-디메틸-1H-이미다졸 염 촉진제, 무수물 경화제 및 에폭시 조성물의 열적거동을 조사한 결과 에폭시 조성물내에서 무수물 촉진재로서 활성을 나타내었다.According to the present invention, the thermal behavior of the 1,2-dimethyl-1H-imidazole salt accelerator, the anhydride curing agent and the epoxy composition was investigated, and as a result, they showed activity as an anhydride accelerator in the epoxy composition.
또한, 실시예 1에 기재된 절차에 따라 제조된 여러 이미다졸 염을 작업 시간 (잠재성)에 대해 25℃에서의 작업 시간을 브룩필드 점도계에 의해 측정하였다. 시간에 따른 점도를 기록하고, 10 및 100 Pa.s까지의 시간을 작업 시간에 대한 척도로서 사용하였다. 이에 따른 조사결과 일반적인 경우보다 본 발명에 따른 이미다졸 염은 더 긴 작업 시간을 제공하였다.In addition, the working time at 25° C. with respect to the working time (latency) of several imidazole salts prepared according to the procedure described in Example 1 was measured by means of a Brookfield viscometer. Viscosity over time was recorded and times up to 10 and 100 Pa.s were used as a measure for working time. As a result of the investigation, the imidazole salt according to the present invention provided a longer working time than the general case.
또한, 500 ml 용기에 상기 본 발명에 따라 제조된 이미다졸 염을 무수물 혼합물과 균일한 혼합물이 수득될 때까지 혼합하여 얻은 수득물의 시각적 외관을 분석한 결과 우수한 상용성을 나타내었다.In addition, as a result of analyzing the visual appearance of the obtained product by mixing the imidazole salt prepared according to the present invention in a 500 ml container with the anhydride mixture until a homogeneous mixture was obtained, excellent compatibility was shown.
아울러, 본 발명의 이미다졸 염은 에폭시 수지와 함께 상당히 더 긴 작업 시간을 제공하며, 여전히 충분한 승온 반응성을 제공하였다.In addition, the imidazole salts of the present invention provide significantly longer working times with epoxy resins and still provide sufficient temperature reactivity.
Claims (5)
경화 촉진제로서 이미다졸 염을 준비하는 단계;
경화제로서 무수물을 준비하는 단계; 및
상기 이미다졸 염을 무수물 100중량부당 1 내지 40중량부 비율로 혼합하고, 이렇게 배합한 혼합 경화제를 에폭시 수지와 중량비로 0.9 내지 1.1의 비율로 혼합하는 단계를 포함하며,
상기 경화촉진제 이미다졸 염은 1,2-디메틸-1H-이미다졸을 카르복실산 화합물을 혼합하여 이루어지는 무수물 경화제를 이용한 에폭시 수지 조성물의 제조방법.
In the method for producing an epoxy resin composition using an anhydride curing agent,
preparing an imidazole salt as a curing accelerator;
preparing an anhydride as a curing agent; and
Mixing the imidazole salt in a ratio of 1 to 40 parts by weight per 100 parts by weight of anhydride, and mixing the mixed curing agent thus blended with an epoxy resin in a ratio of 0.9 to 1.1 by weight,
The curing accelerator imidazole salt is a method for producing an epoxy resin composition using an anhydride curing agent obtained by mixing 1,2-dimethyl-1H-imidazole with a carboxylic acid compound.
무수물 경화제가 폴리세바스산 및 폴리아젤라산 무수물; 메틸테트라히드로프탈산 무수물, 테트라히드로 프탈산 무수물, 메틸 나드산 무수물, 헥사히드로 프탈산 무수물 및 메틸헥사히드로 프탈산 무수물; 숙신산 무수물, 치환된 숙신산 무수물, 시트르산 무수물, 말레산 무수물, 말레산 무수물의 부가물, 도데실 숙신산 무수물, 말레산 무수물 비닐 및 말레산 무수물의 스티렌 공중합체, 다중-고리 지환족 무수물, 프탈산 무수물, 트리멜리트산 무수물, 및 그의 조합으로 이루어진 군으로부터 선택된 적어도 1종의 구성원을 포함하는 무수물 경화제를 이용한 에폭시 수지 조성물의 제조방법.
3. The method of claim 2,
Anhydride curing agents include polysebacic acid and polyazelaic anhydride; methyltetrahydrophthalic anhydride, tetrahydrophthalic anhydride, methyl nadic anhydride, hexahydrophthalic anhydride and methylhexahydrophthalic anhydride; succinic anhydride, substituted succinic anhydride, citric anhydride, maleic anhydride, adduct of maleic anhydride, dodecyl succinic anhydride, styrene copolymer of maleic anhydride vinyl and maleic anhydride, polycyclic alicyclic anhydride, phthalic anhydride, A method for producing an epoxy resin composition using an anhydride curing agent comprising at least one member selected from the group consisting of trimellitic anhydride, and combinations thereof.
상기 경화제와 에폭시 수지의 혼합반응은 50 내지 200 ℃에서 이루어지는 무수물 경화제를 이용한 에폭시 수지 조성물의 제조방법.
3. The method of claim 2,
The mixing reaction of the curing agent and the epoxy resin is a method for producing an epoxy resin composition using an anhydride curing agent made at 50 to 200 ℃.
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