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KR920014787A - 2-(2',4'-디하이드록시페닐)-4,6-디아릴-s-트리아진의 제조방법 - Google Patents

2-(2',4'-디하이드록시페닐)-4,6-디아릴-s-트리아진의 제조방법 Download PDF

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Publication number
KR920014787A
KR920014787A KR1019920001264A KR920001264A KR920014787A KR 920014787 A KR920014787 A KR 920014787A KR 1019920001264 A KR1019920001264 A KR 1019920001264A KR 920001264 A KR920001264 A KR 920001264A KR 920014787 A KR920014787 A KR 920014787A
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South Korea
Prior art keywords
triazine
diaryl
hydroxy
formula
solvent
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KR1019920001264A
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KR100218819B1 (ko
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부르데스카 쿠르트
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베르너 발데그
시바-가이기 에이지
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
    • C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • B01J27/06—Halogens; Compounds thereof
    • B01J27/125—Halogens; Compounds thereof with scandium, yttrium, aluminium, gallium, indium or thallium

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

내용 없음

Description

2-(2',4'-디하이드록시페닐)-4,6-디아릴-S-트리아진의 제조방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (15)

  1. 일반식(2)의 2-하이드록시-4,6-디아릴-s-트리아진을 촉매량의 극성 용매의 존재하에 100내지 150℃ 온도범위에서 티오닐 클로라이드와 반응시키고, 계속하여 클로로-s-트리아진 중간체를 불활성 유기 용매의 존재하에 루이스 산을 사용하여 1,3-디하이드록시벤젠과 반응시킴을 포함하여, 일반식(1)의 2-(2',4'-디하이드록시페닐)-4,6-디아릴-s-트리아진을 제조하는 방법.
    상기식에서, 환 A는 할로겐, 하이드록시, 저급 알킬, 저급 알콕시 또는 저급 알콕시카보닐에 의해 추가로 치환될 수 있다.
  2. 제 1항에 있어서, 일반식(1) 및 (2)의 환 A가 추가로 치환되지 않는 방법.
  3. 제 1항 또는 제 2항에 있어서, 루이스 산이 무수 알루미늄 클로라이드인 방법.
  4. 제 1항 내지 제 3항 중의 어느 한 항에 있어서, 불활성 유기 용매가 톨루엔, 크실렌 및 크실렌 이성체들의 혼합물로 이루어진 그룹중에서 선택되는 방법.
  5. 제 1항 내지 제 4항 중의 어느 한 항에 있어서, 극성 용매가 디메틸 포름아미드인 방법.
  6. 제 1항 내지 제 5항 중의 어느 한 항에 있어서, 용매가 크실렌 이성체들의 혼합물 및 디메틸 포름아미드로 이루어진 그룹중에서 선택되는 방법.
  7. 제 1항 내지 제 5항 중의 어느 한 항에 있어서, 2-하이드록시-4,6-디페닐-s-트리아진을 촉매량의 디메틸포름아미드의 존재하에 티오닐 클로라이드와 반응시키고, 계속하여 클로로-s-트리아진 중간체를 톨루엔, 크실렌 또는 크실렌 이성체들의 혼합물의 존재하에 무수 알루미늄 클로라이드를 사용하여 1,3-디하이드록시벤젠과 반응시킴을 포함하는 방법.
  8. 다음 반응도식에 따라서, 벤즈아미딘 하이드로할라이드의 알칼리 수용액을 0 내지 80℃의 온도범위에서 알킬 포르메이트와 반응시켜 알킬 벤즈이미도일카바메이트를 수득하고, 생성된 유액에 불활성 유기 용매를 가한 다음, 알킬 벤즈이미도일카바메이트를 함유하는 유기상을 반응시켜 2-하이드록시-4,6-디아릴-s-트리아진을 수득함을 포함하여, 일반식(2)의 2-하이드록시-4,6-디아릴-s-트리아진을 제조하는 방법.
    상기식에서 Hal1및 Hal2는 할로겐이고, R은 C1-C4알킬이며, A는 일반식(2)에 대해 정의된 바와 같다.
  9. 제 8항에 있어서, 반응이 150 내지 200mbar의 감압하에서 수행되는 방법.
  10. 제 8항 또는 제 9항에 있어서, 벤즈아미딘 하이드로할라이드가 벤즈아미딘 하이드로클로라이드인 방법.
  11. 제 8항 내지 제 10항 중의 어느 한 항에 있어서, 포르메이트가 에틸 브로모포르메이트 또는 에틸 클로로포르메이트인 방법.
  12. 제 8항 내지 제 11항 중의 어느 한 항에 있어서, 벤즈아미딘 하이드로할라이드의 알칼리 용액이 수산화나트륨 용액인 방법.
  13. 제 8항 내지 제 12항중의 어느 한 항에 있어서, 불활성 유기 용매가 비점이 160 내지 250℃인 용매인 방법.
  14. 제 13항에 있어서, 용매가 o-디클로로벤젠, 니트로벤젠, 1,2,3-트리메틸벤젠, 26.5%의 디페닐과 73.5%의 디페닐 에테르의 혼합물 및 아니졸로 이루어진 그룹중에서 선택되는 방법.
  15. 벤즈아미딘 하이드로할라이드를 150 내지 200mbar의 감압하에서 알킬 포르메이트와 반응시켜 제 8항에 따르는 일반식(2)의 2-하이드록시-4,6-디아릴-s-트리아진을 수득하고, 이 중간체를 분리하지 않으면서 100 내지 150℃에서 촉매량의 극성 용매의 존재하에 티오닐 클로라이드와 반응시키며, 계속하여 클로로-s-트리아진 중간체를 불황성 유기 용매의 존재하에 루이스산을 사용하여 1,3-디하이드록시벤젠과 반응시켜 일반식(1)의 화합물을 수득함을 포함하여, 일반식(1)의 2-(2',4'-디하이드록시페닐)-4,6-디아릴-s-트리아진을 제조하는 방법.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019920001264A 1991-01-31 1992-01-29 2-(2',4'-디하이드록시페닐)-4,6-디아릴-에스-트리아진의 제조방법 KR100218819B1 (ko)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
CH29191 1991-01-31
CH291/91-7 1991-01-31
CH02788/91-4 1991-09-23
CH00291/91-7 1991-09-23
CH278891 1991-09-23
CH2788/91-4 1991-09-23

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KR920014787A true KR920014787A (ko) 1992-08-25
KR100218819B1 KR100218819B1 (ko) 1999-09-01

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US (1) US5182389A (ko)
EP (1) EP0497734B1 (ko)
JP (1) JP3067878B2 (ko)
KR (1) KR100218819B1 (ko)
AT (1) ATE192743T1 (ko)
BR (1) BR9200303A (ko)
DE (1) DE59209837D1 (ko)
ES (1) ES2146208T3 (ko)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE59409434D1 (de) * 1993-10-15 2000-08-17 Ciba Sc Holding Ag Verfahren zur Herstellung von Hydroxyphenyl-1,3,5-Triazinen
JP3105778B2 (ja) * 1995-10-23 2000-11-06 大淀小松株式会社 カーペットクリーナー及びカーペットの清浄化方法
DE19543730A1 (de) * 1995-11-23 1997-05-28 Ciba Geigy Ag Bis-Resorcinyl-Triazine
GB2319523B (en) 1996-11-20 2000-11-08 Ciba Sc Holding Ag Hydroxyphenyltriazines
DE19735900A1 (de) * 1997-08-19 1999-02-25 Beiersdorf Ag Kosmetische oder dermatologische Lichtschutzmittel, welche gelöste Triazinderivate und polymere UV-Filtersubstanzen auf Siliconbasis enthalten
DE19735899A1 (de) * 1997-08-19 1999-02-25 Beiersdorf Ag Wirkstoffkombinationen aus einer oder mehreren grenzflächenaktiven Substanzen und oligomeren oder polymeren UV-Filtersubstanzen mit periodisch sich wiederholenden Si-0-Gruppen
DE19735901A1 (de) * 1997-08-19 1999-02-25 Beiersdorf Ag Kosmetische oder dermatologische Lichtschutzmittel, welche als Festkörper vorliegende UV-Filtersubstanzen und polymere UV-Filtersubstanzen auf Siliconbasis enthalten
JP2002524452A (ja) 1998-09-04 2002-08-06 サイテク・テクノロジー・コーポレーシヨン ２−（２，４−ジヒドロキシフェニル）もしくは２−（２，４−ジアルコキシフェニル）−４，６−ビスアリール−１，３，５−トリアジンの製造方法
TWI259182B (en) 1998-11-17 2006-08-01 Cytec Tech Corp Process for preparing triazines using a combination of Lewis acids with reaction promoters
US20050155163A1 (en) * 2004-01-21 2005-07-21 Griffin Bruce O. Dye mixtures
EP1820801B1 (en) 2004-12-10 2015-04-01 Pioneer Corporation Organic compound, charge-transporting material, and organic electroluminescent element
WO2010081625A2 (en) 2009-01-19 2010-07-22 Basf Se Organic black pigments and their preparation
CN106083751A (zh) * 2016-06-21 2016-11-09 三峡大学 一种均三嗪类紫外线吸收剂uv‑1577的制备方法
CN113260679A (zh) * 2019-01-08 2021-08-13 巴斯夫欧洲公司 制备三嗪中间体的方法和制备其uv吸收剂的方法
CN116178289B (zh) * 2022-12-26 2024-06-14 天津利安隆新材料股份有限公司 一种醚化合成三嗪化合物的方法

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US2691018A (en) * 1951-07-10 1954-10-05 American Cyanamid Co Process of chlorinating hydroxy triazines with thionyl chloride
EP0395938B1 (de) * 1989-04-21 1996-01-17 Ciba-Geigy Ag Verfahren zur Herstellung von 2-(2',4'-Dihydroxyphenyl)-4,6-diaryl-s-triazinen

Also Published As

Publication number Publication date
DE59209837D1 (de) 2000-06-15
EP0497734B1 (de) 2000-05-10
BR9200303A (pt) 1992-10-06
ATE192743T1 (de) 2000-05-15
JP3067878B2 (ja) 2000-07-24
JPH0570443A (ja) 1993-03-23
EP0497734A1 (de) 1992-08-05
US5182389A (en) 1993-01-26
ES2146208T3 (es) 2000-08-01
KR100218819B1 (ko) 1999-09-01

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