WO2016163675A1 - Résine époxy modifiée dérivée d'huile extraite de coque de noix de cajou, composition de résine époxy comprenant cette résine, et procédé de production associé - Google Patents

Résine époxy modifiée dérivée d'huile extraite de coque de noix de cajou, composition de résine époxy comprenant cette résine, et procédé de production associé Download PDF

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Publication number
WO2016163675A1
WO2016163675A1 PCT/KR2016/003168 KR2016003168W WO2016163675A1 WO 2016163675 A1 WO2016163675 A1 WO 2016163675A1 KR 2016003168 W KR2016003168 W KR 2016003168W WO 2016163675 A1 WO2016163675 A1 WO 2016163675A1
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WO
WIPO (PCT)
Prior art keywords
epoxy resin
epoxy
acid
modified epoxy
cashew nut
Prior art date
Application number
PCT/KR2016/003168
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English (en)
Korean (ko)
Inventor
김재원
임경진
심선우
Original Assignee
국도화학 주식회사
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Application filed by 국도화학 주식회사 filed Critical 국도화학 주식회사
Priority to CN201680015422.3A priority Critical patent/CN107428912A/zh
Publication of WO2016163675A1 publication Critical patent/WO2016163675A1/fr

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Classifications

    • 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
    • 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
    • C08G59/62—Alcohols or phenols
    • 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
    • C08G59/02—Polycondensates containing more than one epoxy group per molecule
    • C08G59/04—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof
    • C08G59/06—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof of polyhydric phenols
    • C08G59/08—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof of polyhydric phenols from phenol-aldehyde condensates
    • 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
    • C08G59/4223—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof aromatic
    • 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
    • C08G59/4284—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof together with other curing agents
    • 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
    • C08G59/68—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 catalysts used
    • C08G59/688—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 catalysts used containing phosphorus

Definitions

  • the present invention relates to a cashew nut shell extract oil derivative-modified epoxy resin, a cashew nut shell extract oil derivative-modified epoxy resin comprising the cashew nut shell extract oil derivative-modified epoxy resin, and a preparation method thereof.
  • a cashew nut shell extract oil derivative modified epoxy resin having excellent rust resistance, chemical resistance and low viscosity and a cashew nut shell extract oil derivative modified epoxy resin composition comprising the cashew nut shell extract oil derivative modified epoxy resin and their It relates to a manufacturing method.
  • epoxy resins are known to have excellent mechanical and chemical properties compared to other types of resins. Due to the above characteristics, it is applied to ships, civil engineering, construction, electricity, electronic materials, and composite materials, and is widely used as a material for preventing corrosion of steel sheets.
  • the epoxy resin used in the medium method is applied as a coat and top to prevent corrosion of the iron plate excellent in adhesion and water resistance, and the demand is increasing.
  • the existing cardanol-modified epoxy resin has a disadvantage of rust resistance and chemical resistance.
  • the present invention has been made in view of the above point, and an object of the present invention is to provide an epoxy resin having low viscosity characteristics, overcoming the rust resistance and chemical resistance which is the limitation of the existing cardanol-modified epoxy resin.
  • Another object of the present invention is to provide an epoxy resin composition comprising the epoxy resin described above.
  • the present invention provides a cashew nut shell extract oil derivative-modified epoxy resin represented by the following general formula (1) modified with an aromatic dicarboxylic acid and aliphatic dicarboxylic acid.
  • X is cardanol or epoxide
  • Y is phthalic acid (Phthalic aicd), isophthalic acid (Tephthalic acid), terephthalic acid (Diereic acid), aromatic dicarboxylic acid, oxalic acid (Oxalic aicd), malonic acid (Malonic aicd), succinic acid ( succinic acid, glutaric acid, or cadol,
  • N is an integer of 0 to 30.
  • Y is particularly phthalic acid
  • X may be cardanol
  • the present invention includes an epoxy resin composition
  • the composition includes 10 to 50% by weight of a solvent capable of diluting it in 50 to 90% by weight of the epoxy resin of Formula 1.
  • Xylene is exemplified as the diluting solvent.
  • the method for preparing an epoxy resin having excellent rust resistance and chemical resistance and low viscosity may include: i) bisphenol A epoxy, bisphenol F epoxy, bisphenol A epoxy, bisphenol A epoxy, bisphenol M epoxy, phenol novolac epoxy, 20 to 84% by weight of at least one epoxy resin selected from the group consisting of cresol novolac epoxy, BP novolac epoxy, rubber modified epoxy, fatty acid modified epoxy, urethane modified epoxy and silane modified epoxy, cashew nut shell oil (CNSL, cashew nut) shell liquid derivatives 5-30% by weight, aromatic and / or aliphatic dicarboxylic acids 5-30% by weight, and tertiary phosphine, tertiary ammonium salt, tetra ammonium salt And quaternary phosphonium salts. Mixing the falcons with remainder;
  • the CNSL derivative may be cardol or / and cardanol, preferably cardanol.
  • aromatic dicarboxylic acid may be phthalic acid.
  • the epoxy resin prepared above is characterized in that the number average molecular weight of 400 to 6,000.
  • the epoxy equivalent of the prepared epoxy resin is characterized in that 300 to 3,000.
  • Epoxy resin composition of the present invention is not only excellent in adhesion, but also excellent in chemical resistance by appropriately introducing aromatic and aliphatic compounds into the molecule compared to the conventional CNSL derivative, typically an epoxy resin compound modified with cardanol. And low viscosity is very easy.
  • CNSL derivative-modified epoxy resin according to the present invention has improved corrosion resistance and chemical resistance and low viscosity characteristics compared to the conventional cardanol modified epoxy resin, it can be used as the subject of the heavy-duty resin which requires these physical properties.
  • the present invention provides a cashew nut shell extract oil derivative-modified epoxy resin represented by the following formula (1).
  • X is cardanol or epoxide
  • Y is phthalic acid (Phthalic aicd), isophthalic acid (Tephthalic acid), terephthalic acid (Diereic acid), aromatic dicarboxylic acid, oxalic acid (Oxalic aicd), malonic acid (Malonic aicd), succinic acid ( succinic acid, glutaric acid or cadol,
  • n is an integer of 0 to 30.
  • Cardanol or epoxide may be bonded to both sides of the epoxy resin terminal, or may be bonded to only one side.
  • the structural unit may exist in various forms in the whole resin.
  • the epoxy resin prepared according to the present invention preferably has an epoxy equivalent of 300 to 3,000 g / eq, more preferably 300 to 2,000 g / eq. If the epoxy equivalent is less than 300 g / eq, the physical performance of the cured coating film is not sufficiently exhibited. If the epoxy equivalent is more than 3,000 g / eq, the viscosity is too high, making it difficult to high-solidize.
  • the production method of the epoxy resin of the present invention is i) bisphenol A epoxy, bisphenol F epoxy, bisphenol A epoxy, bisphenol A epoxy, bisphenol M epoxy, phenol novolac epoxy, cresol novolac epoxy, BP novolac epoxy, 20 to 84% by weight of at least one epoxy resin selected from the group consisting of rubber-modified epoxy, fatty acid-modified epoxy, urethane-modified epoxy and silane-modified epoxy, 5 to 30% by weight of cashew nut shell liquid (CNSL) derivatives, Mixing step of mixing 5 to 30% by weight of aromatic and / or aliphatic dicarboxylic acid ii) Step of forming the epoxy resin solution having excellent anti-rusting and chemical resistance and low viscosity by heating the mixed composition to 110 to 200 °C And iii) cooling and diluting the resin solution.
  • At least one catalyst selected from the group consisting of tertiary phosphine, tertiary ammonium salt, tetra ammonium salt and quaternary phosphonium salt as a catalyst is used.
  • Ethyltriphenylphosphonium Iodide (ETPPI) catalyst which is a quaternary phosphonium salt, is preferably used.
  • the epoxy resin is a bisphenol A epoxy resin known to have excellent chemical performance, and phthalic acid is used as the dicarboxylic acid.
  • the CNSL derivative is cardanol
  • the epoxy resin is BPA
  • the dicarboxylic acid is phthalic acid.
  • the bisphenol-A epoxy resin known to be excellent in chemical performance can be used.
  • Such bisphenol A epoxy resin is represented by the following formula (2).
  • n is from 0 to 12.
  • Specific examples of the epoxy resins include YD-128, YD-011, YD-014, YD-017, and YD-019 (above, trade names of Kukdo Chemical), and other companies having similar characteristics (Dow, Momentive).
  • the product can also be used and can be easily obtained on the market.
  • CNSL derivative In order to prepare the CNSL derivative-modified epoxy resin according to the present invention, the CNSL derivative must be reacted with the epoxy resin.
  • Representative component of CNSL derivative is cardanol whose structural formula is represented by the following Chemical Formula 3.
  • Cardanol is one of the main components of CNSL (cashew nut shell liquid), which is a phenolic structure containing unsaturated groups and a by-product generated in large quantities during the production and processing of cashew nuts. It basically has a phenolic hydroxyl group, so it is used to react with the epoxy resin.
  • reaction of the epoxide with the phenolic hydroxy group can be partially reacted at a high temperature, but the catalyst is used for commercially efficient production.
  • the reaction temperature is run at approximately 110 to 200 °C. Due to the unsaturated group such as cardanol and PtBP, it is easy to lower the viscosity, so that a special solvent is not used, but if necessary, an aromatic solvent such as xylene can be used to more easily decrease the viscosity.
  • the reaction between the epoxy resin and cardanol is preferably performed for about 2 to 6 hours.
  • the content of the epoxy resin added during the reaction is preferably 20 to 84% by weight. More preferably, it is 70 to 80 weight%.
  • the content of the epoxy resin in the reaction is less than 20% by weight, the chemical resistance is not sufficient, whereas if the content of the epoxy resin exceeds 84% by weight, the adhesion, water repellency is lowered, and the high solidification and low embrittlement action becomes difficult.
  • the content of phthalic acid added during the reaction is preferably 5 to 30% by weight. If the content of phthalic acid is less than 5% by weight, the chemical resistance is not sufficient, whereas if the content of the phthalic acid is more than 30% by weight, a phenomenon of increasing the viscosity of the resin occurs, making it difficult to lower the viscosity and high solidification of the epoxy resin.
  • the cardanol-modified epoxy resin produced by the reaction has a structural formula represented by the following formula (4).
  • X is cardanol or epoxide
  • Y is phthalic acid (Phthalic aicd)
  • n is an integer of 0 to 30.
  • Cardanol may be bonded to both sides of the epoxy resin terminal, or may be bonded to only one side.
  • the structural unit may exist in various forms in the whole resin.
  • the epoxy resin prepared according to the present invention preferably has an epoxy equivalent of 300 to 3,000 g / eq, more preferably 300 to 2,000 g / eq. If the epoxy equivalent is less than 300 g / eq, the physical performance of the cured coating film is not sufficiently exhibited. If the epoxy equivalent is more than 3,000 g / eq, the viscosity is too high, making it difficult to high-solidize.
  • the prepared number average molecular weight of Formula 1 has 400 to 6,000. If the number average molecular weight of the resin is less than 400, the defect of the cured coating film appears. If the number average molecular weight of the resin is 6,000 or more, the hardness is high and the adhesion is poor and the content of the epoxy resin is high, so that high solidification and low embrittlement are difficult.
  • the cardanol-modified epoxy resin composition is prepared by diluting the cardanol-modified epoxy resin with a diluting solvent.
  • Xylene is preferred as the diluent solvent.
  • the cardanol-modified epoxy resin composition includes 50 to 90% by weight of the cardanol-modified epoxy resin and 10 to 50% by weight of the dilution solvent.
  • the epoxy resin of this invention which has the characteristic value of the viscosity (25 degreeC) 88,000 CPS and epoxy equivalent 829 g / eq was obtained.
  • the epoxy resin of this invention which has the characteristic value of viscosity (25 degreeC) 4409 CPS and epoxy equivalent 453 g / eq was obtained.
  • the impact resistance test results of Table 2 were evaluated based on ASTM D 2794, and the improved impact resistance was confirmed as compared with the existing bisphenol A type epoxy resin (YD-011X75 manufactured by Kukdo Chemical).
  • the flex resistance test results were evaluated based on ISO 1520, and improved flex resistance results were obtained compared to the existing bisphenol A-type epoxy resin (YD-136X80 manufactured by Kukdo Chemical).
  • Table 3 was evaluated based on the ASTM D 714 test method, the result of confirming the water resistance and corrosion resistance after 14 days immersed in a 70 °C autoclave specimen. Compared with the existing bisphenol A type epoxy resin (YD-011X75, YD-136X80 manufactured by Kukdo Chemical Co., Ltd.), water resistance and corrosion resistance were improved.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Epoxy Resins (AREA)
  • Emergency Medicine (AREA)
  • General Chemical & Material Sciences (AREA)
  • Paints Or Removers (AREA)

Abstract

La présente invention concerne : une résine époxy modifiée dérivée d'huile extraite de coque de noix de cajou qui présente des propriétés anticorrosion et une résistance aux produits chimiques qui sont remarquables, et qui est capable d'abaisser la viscosité ; une composition de résine époxy modifiée dérivée d'huile extraite de coque de noix de cajou comprenant la résine époxy modifiée dérivée d'huile extraite de coque de noix de cajou ; et un procédé de production associé.
PCT/KR2016/003168 2015-04-06 2016-03-29 Résine époxy modifiée dérivée d'huile extraite de coque de noix de cajou, composition de résine époxy comprenant cette résine, et procédé de production associé WO2016163675A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201680015422.3A CN107428912A (zh) 2015-04-06 2016-03-29 腰果壳提取油衍生物改性环氧树脂、包含其的环氧树脂组合物及其制备方法

Applications Claiming Priority (2)

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KR1020150048188A KR101717974B1 (ko) 2015-04-06 2015-04-06 카슈너트껍질 추출오일 유도체 변성 에폭시 수지, 이를 포함하는 에폭시 수지 조성물 및 이의 제조방법
KR10-2015-0048188 2015-04-06

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WO2016163675A1 true WO2016163675A1 (fr) 2016-10-13

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113683752A (zh) * 2021-10-14 2021-11-23 山东天茂新材料科技股份有限公司 一种高韧性环氧树脂的制备方法
CN113956612A (zh) * 2021-09-22 2022-01-21 广东华彩复合材料有限公司 一种风电叶片用手糊环氧树脂复合材料
CN116041670A (zh) * 2022-12-20 2023-05-02 江苏扬农锦湖化工有限公司 一种酸改性环氧树脂及其制备方法和应用
CN116120871A (zh) * 2023-01-10 2023-05-16 安徽牛元新材料有限公司 一种清味弹性干挂胶及其制备方法

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JPH10218973A (ja) * 1997-02-05 1998-08-18 Asahi Chem Ind Co Ltd カルドール構造を有する新規エポキシ樹脂
JP2001139810A (ja) * 1999-11-19 2001-05-22 Yokohama Rubber Co Ltd:The 硬化型組成物
KR100559055B1 (ko) * 2004-12-30 2006-03-10 주식회사 디피아이 카다놀 변성 에폭시 수지 조성물
KR100829071B1 (ko) * 2006-12-27 2008-05-19 (주)디피아이 홀딩스 에폭시 수지, 이를 포함하는 에폭시 수지 조성물, 도료조성물 및 이를 이용한 도막의 형성 방법
KR20140143408A (ko) * 2012-03-20 2014-12-16 다우 글로벌 테크놀로지스 엘엘씨 고 고형분 코팅에 사용되는 개질된 에폭시 수지 조성물

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113956612A (zh) * 2021-09-22 2022-01-21 广东华彩复合材料有限公司 一种风电叶片用手糊环氧树脂复合材料
CN113956612B (zh) * 2021-09-22 2024-01-09 山西宇德新材料科技有限公司 一种风电叶片用手糊环氧树脂复合材料
CN113683752A (zh) * 2021-10-14 2021-11-23 山东天茂新材料科技股份有限公司 一种高韧性环氧树脂的制备方法
CN116041670A (zh) * 2022-12-20 2023-05-02 江苏扬农锦湖化工有限公司 一种酸改性环氧树脂及其制备方法和应用
CN116120871A (zh) * 2023-01-10 2023-05-16 安徽牛元新材料有限公司 一种清味弹性干挂胶及其制备方法

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CN107428912A (zh) 2017-12-01
KR20160119892A (ko) 2016-10-17

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