JP4786131B2 - 2,4,6−トリアニリノ−p−(カルボ−2’−エチルヘキシル−1’−オキシ)−1,3,5−トリアジンの互変異性体の調製方法 - Google Patents
2,4,6−トリアニリノ−p−(カルボ−2’−エチルヘキシル−1’−オキシ)−1,3,5−トリアジンの互変異性体の調製方法 Download PDFInfo
- Publication number
- JP4786131B2 JP4786131B2 JP2003572968A JP2003572968A JP4786131B2 JP 4786131 B2 JP4786131 B2 JP 4786131B2 JP 2003572968 A JP2003572968 A JP 2003572968A JP 2003572968 A JP2003572968 A JP 2003572968A JP 4786131 B2 JP4786131 B2 JP 4786131B2
- Authority
- JP
- Japan
- Prior art keywords
- carbon atoms
- total
- aliphatic
- triazine
- ethylhexyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
Images
Classifications
-
- 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
- C07D251/26—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 only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/54—Three nitrogen atoms
-
- 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
- C07D251/26—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 only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/54—Three nitrogen atoms
- C07D251/70—Other substituted melamines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cosmetics (AREA)
- Plural Heterocyclic Compounds (AREA)
Description
エタノールからの再結晶による互変異性体Iの調製
250 kgのs-トリクロロトリアジン (1.36 kmolに相当) を、溶媒としてのキシレン中で1025 kgのp-アミノ安息香酸2-エチルヘキシル (4.11 kmolに相当) と反応させて、2,4,6-トリアニリノ-p-(カルボ-2'-エチルヘキシル-1'-オキシ)-1,3,5-トリアジン互変異性体混合物を得た。
酢酸エチルからの再結晶による互変異性体Iの調製
実施例1と同様に、用いた互変異性体混合物に基づいて、400重量%の酢酸エチルを使用して再結晶を行った。互変異性体として純粋な生成物が58%の収率で得られた。
実施例1と同様に、それぞれの場合にエチルヘキサノール(実施例3)、シクロヘキサノール(実施例4)、安息香酸メチル(実施例5)、テトラメチレンスルホン(実施例6)、炭酸ジメチル(実施例7)、メチルエチルケトン(実施例8)、アセトニトリル(実施例9)、およびアセトン(実施例10)、ならびに90重量%のエタノール/10重量%のキシレンの混合溶媒(実施例11)、および90重量%の酢酸エチル/10重量%のキシレンの混合溶媒(実施例12)を用いて再結晶を行った。
石油スピリットからの再結晶
特許明細書(1)に従って、調製により得られた互変異性体混合物を、120〜130℃の沸騰範囲を有する石油スピリットから再結晶した。
化粧品用オイルに溶解した互変異性体Iの溶液の貯蔵安定性
互変異性体として純粋な化合物Iを、それぞれC8-C10-ヤシ脂肪酸トリグリセリド(オイル100 gあたりの溶解度5.8 g)およびセチルステアリル2-エチルへキサノエート(オイル100 gあたりの溶解度1.0 g)に溶解した。両方の溶液とも2日経過後になおも透明であった。
Claims (3)
- 2,4,6-トリアニリノ-p-(カルボ-2'-エチルヘキシル-1'-オキシ)-1,3,5-トリアジンの互変異性体I:
- 2〜4個の炭素原子を有する脂肪族アルコール、合計3〜6個の炭素原子を有する脂肪族カルボン酸アルキルエステル、またはこれらの混合溶媒中で結晶化を実施する、請求項1に記載の方法。
- エタノール、酢酸エチル、またはこれらの混合溶媒中で結晶化を実施する、請求項1または2に記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10208840A DE10208840A1 (de) | 2002-03-01 | 2002-03-01 | Verfahren zur Herstellung einer tautomeren Form von 2,4,6-Trianilino-p-(carbo-2'-ethylhexyl-1'-oxy)-1,3,5-triazin |
DE10208840.3 | 2002-03-01 | ||
PCT/EP2003/001931 WO2003074499A1 (de) | 2002-03-01 | 2003-02-26 | Verfahren zur herstellung einer tautomeren form (i) von 2, 4, 6-trianilino-p- (carbo-2'-ethylhexyl-1'-oxy)-1, 3, 5-triazin |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2005526747A JP2005526747A (ja) | 2005-09-08 |
JP4786131B2 true JP4786131B2 (ja) | 2011-10-05 |
Family
ID=27762520
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2003572968A Expired - Lifetime JP4786131B2 (ja) | 2002-03-01 | 2003-02-26 | 2,4,6−トリアニリノ−p−(カルボ−2’−エチルヘキシル−1’−オキシ)−1,3,5−トリアジンの互変異性体の調製方法 |
Country Status (14)
Country | Link |
---|---|
US (1) | US7074922B2 (ja) |
EP (1) | EP1483250B1 (ja) |
JP (1) | JP4786131B2 (ja) |
KR (1) | KR100959721B1 (ja) |
CN (1) | CN1324016C (ja) |
AT (1) | ATE466001T1 (ja) |
AU (1) | AU2003210356A1 (ja) |
BR (2) | BR0307455A (ja) |
DE (2) | DE10208840A1 (ja) |
ES (1) | ES2343406T3 (ja) |
IL (1) | IL163112A (ja) |
MX (1) | MXPA04007479A (ja) |
WO (1) | WO2003074499A1 (ja) |
ZA (1) | ZA200407892B (ja) |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8508688B2 (en) * | 2009-02-12 | 2013-08-13 | Panasonic Corporation | Illuminating lens, lighting device, surface light source, and liquid-crystal display apparatus |
ITMI20122009A1 (it) * | 2012-11-27 | 2014-05-28 | 3V Sigma Spa | Forma solida amorfa stabile di un derivato triazinico e relativo procedimento per la sua produzione |
ITMI20130357A1 (it) | 2013-03-08 | 2014-09-09 | 3V Sigma Spa | Forma cristallina di un derivato triazinico e relativo procedimento per la sua produzione |
US10449135B2 (en) | 2014-04-09 | 2019-10-22 | Basf Se | Solublizing agents for UV filters in cosmetic formulations |
JP2017517489A (ja) | 2014-04-11 | 2017-06-29 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | 化粧品紫外線吸収体の混合物 |
CN105061345B (zh) * | 2015-08-05 | 2017-11-10 | 宜都市华阳化工有限责任公司 | 一种紫外线吸收剂乙基己基三嗪酮的合成方法 |
IT201600080304A1 (it) | 2016-07-29 | 2018-01-29 | 3V Sigma Spa | Composizioni cosmetiche di filtri uv |
IT201600080301A1 (it) | 2016-07-29 | 2018-01-29 | 3V Sigma Spa | Nuovi composti triazinici come agenti fotostabilizzanti |
IT201800006038A1 (it) | 2018-06-05 | 2019-12-05 | Agenti fotoprotettori di elevata efficacia | |
CN115677604A (zh) * | 2021-07-21 | 2023-02-03 | 马鞍山科思化学有限公司 | 一种防晒剂辛基三嗪酮的纯化方法 |
IT202200006299A1 (it) | 2022-03-30 | 2023-09-30 | 3V Sigma S P A | Processo di preparazione di forme tautomeriche di filtri solari |
WO2024046956A1 (en) | 2022-08-29 | 2024-03-07 | Basf Se | Improved process for preparing s-triazine derivatives |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS58157774A (ja) * | 1982-02-23 | 1983-09-19 | バスフ アクチエンゲゼルシヤフト | s−トリアジン誘導体及びその光保護剤としての使用 |
JPS61271281A (ja) * | 1985-05-24 | 1986-12-01 | バスフ アクチェン ゲゼルシャフト | S−トリアジン誘導体の製法 |
-
2002
- 2002-03-01 DE DE10208840A patent/DE10208840A1/de not_active Withdrawn
-
2003
- 2003-02-26 AU AU2003210356A patent/AU2003210356A1/en not_active Abandoned
- 2003-02-26 JP JP2003572968A patent/JP4786131B2/ja not_active Expired - Lifetime
- 2003-02-26 AT AT03743330T patent/ATE466001T1/de active
- 2003-02-26 WO PCT/EP2003/001931 patent/WO2003074499A1/de active Application Filing
- 2003-02-26 MX MXPA04007479A patent/MXPA04007479A/es not_active Application Discontinuation
- 2003-02-26 ES ES03743330T patent/ES2343406T3/es not_active Expired - Lifetime
- 2003-02-26 KR KR1020047013544A patent/KR100959721B1/ko active IP Right Grant
- 2003-02-26 US US10/503,305 patent/US7074922B2/en not_active Expired - Lifetime
- 2003-02-26 EP EP03743330A patent/EP1483250B1/de not_active Expired - Lifetime
- 2003-02-26 CN CNB038050757A patent/CN1324016C/zh not_active Expired - Lifetime
- 2003-02-26 DE DE50312664T patent/DE50312664D1/de not_active Expired - Lifetime
- 2003-02-26 BR BR0307455-2A patent/BR0307455A/pt active IP Right Grant
- 2003-02-26 BR BRPI0307455A patent/BRPI0307455B1/pt unknown
-
2004
- 2004-07-20 IL IL163112A patent/IL163112A/en active IP Right Grant
- 2004-09-30 ZA ZA200407892A patent/ZA200407892B/en unknown
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS58157774A (ja) * | 1982-02-23 | 1983-09-19 | バスフ アクチエンゲゼルシヤフト | s−トリアジン誘導体及びその光保護剤としての使用 |
JPS61271281A (ja) * | 1985-05-24 | 1986-12-01 | バスフ アクチェン ゲゼルシャフト | S−トリアジン誘導体の製法 |
Also Published As
Publication number | Publication date |
---|---|
KR20040093083A (ko) | 2004-11-04 |
JP2005526747A (ja) | 2005-09-08 |
EP1483250B1 (de) | 2010-04-28 |
ATE466001T1 (de) | 2010-05-15 |
BR0307455A (pt) | 2004-11-09 |
KR100959721B1 (ko) | 2010-05-25 |
DE10208840A1 (de) | 2003-09-18 |
WO2003074499A1 (de) | 2003-09-12 |
ZA200407892B (en) | 2006-02-22 |
EP1483250A1 (de) | 2004-12-08 |
DE50312664D1 (de) | 2010-06-10 |
US7074922B2 (en) | 2006-07-11 |
ES2343406T3 (es) | 2010-07-30 |
BRPI0307455B1 (pt) | 2018-09-11 |
US20050143577A1 (en) | 2005-06-30 |
IL163112A (en) | 2011-03-31 |
AU2003210356A1 (en) | 2003-09-16 |
CN1639134A (zh) | 2005-07-13 |
CN1324016C (zh) | 2007-07-04 |
MXPA04007479A (es) | 2004-11-10 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP4786131B2 (ja) | 2,4,6−トリアニリノ−p−(カルボ−2’−エチルヘキシル−1’−オキシ)−1,3,5−トリアジンの互変異性体の調製方法 | |
EA003264B1 (ru) | КРИСТАЛЛИЧЕСКИЕ ФОРМЫ EtO2C-CH2-(R)Cgl-Aze-Pab-OH | |
ES2367390B1 (es) | Derivados de bis-resorcinil triazina como agentes protectores frente a la radiación uv. | |
BRPI0407358B1 (pt) | Composto, processos para a preparação do mesmo e para o combate a fungos danosos, e, agente fungicida | |
EP0949251B1 (de) | Diresorcinyltriazine als Lichtschutzmittel | |
KR101859249B1 (ko) | S-트리아진 화합물의 제조 방법 | |
Iohara et al. | Modification of drug crystallization by cyclodextrins in pre-formulation study | |
JP3836162B2 (ja) | ショ糖脂肪酸エステルの製造方法 | |
TW591018B (en) | Method of preserving quaternary ammonium salt | |
CN1073439A (zh) | 非晶形(喹啉-2-基甲氧基)吲哚 | |
EP0236646B1 (fr) | Nouveaux ortho-anisamides, leur procédé d'obtention et leurs applications thérapeutiques | |
EP0207287A2 (de) | Indolinderivate, Verfahren zu ihrer Herstellung und diese Indolinderivate enthaltende kosmetische Lichtschutzmittel | |
JPH11513402A (ja) | モルヒネ−6−グルクロニドの新しい結晶形態 | |
Chen et al. | Synthetic Triacid Triglycerides of Saturated Fatty Acids1, 2, 3 | |
US6684526B2 (en) | Process for removing trace solvent from a material | |
CN109796405A (zh) | 琥珀八氢氨吖啶多晶型及其制备方法 | |
JPS6041676B2 (ja) | S−2−(3−アミノプロピルアミノ)エチルジハイドロジエンホスホロチオエ−ト1水和結晶の新規製法 | |
JP2013213032A (ja) | (2rs)−1−ジメチルアミノ−3−{2−[2−(3−メトキシフェニル)エチル]フェノキシ}プロパン−2−イルコハク酸水素塩酸塩の工業的製造方法 | |
ITMI20122009A1 (it) | Forma solida amorfa stabile di un derivato triazinico e relativo procedimento per la sua produzione | |
JPH05503932A (ja) | 7―クロル―キノリン―8―カルボン酸の精製方法 | |
US5665334A (en) | Benzofuran derivatives and methods for their use as stabilizers and sunscreens against HIV radiations | |
EP0937716B1 (de) | Verfahren zur Herstellung von Phenyldichloro-1,3,5-triazinverbindungen | |
KR20230121829A (ko) | 결정질 디에틸아미노 하이드록시벤조일 헥실 벤조에이트를수득하는 방법 | |
AU2007278245A1 (en) | Use of aminophenylbenzotriazole derivatives for protecting human and animal skin and hair from the harmful effects of UV radiation and cosmetic compositions thereof | |
TW202413322A (zh) | 用於獲得結晶二乙胺基羥苯甲醯基苯甲酸己酯之方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20060221 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20091117 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20100217 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20100706 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20101004 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20110614 |
|
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20110713 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 4786131 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20140722 Year of fee payment: 3 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
EXPY | Cancellation because of completion of term |