KR101877251B1 - The Preparation Method of UV absorbers - Google Patents

The Preparation Method of UV absorbers Download PDF

Info

Publication number
KR101877251B1
KR101877251B1 KR1020160111739A KR20160111739A KR101877251B1 KR 101877251 B1 KR101877251 B1 KR 101877251B1 KR 1020160111739 A KR1020160111739 A KR 1020160111739A KR 20160111739 A KR20160111739 A KR 20160111739A KR 101877251 B1 KR101877251 B1 KR 101877251B1
Authority
KR
South Korea
Prior art keywords
methoxyphenyl
reaction
triazin
methanol
equivalents
Prior art date
Application number
KR1020160111739A
Other languages
Korean (ko)
Other versions
KR20180024829A (en
Inventor
김용호
이원목
김창일
엄경섭
우상국
Original Assignee
아크로마코리아 주식회사
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 아크로마코리아 주식회사 filed Critical 아크로마코리아 주식회사
Priority to KR1020160111739A priority Critical patent/KR101877251B1/en
Publication of KR20180024829A publication Critical patent/KR20180024829A/en
Application granted granted Critical
Publication of KR101877251B1 publication Critical patent/KR101877251B1/en

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C257/00—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines
    • C07C257/10—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines
    • C07C257/18—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines having carbon atoms of amidino groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C255/53—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and hydroxy groups bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C255/54—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and etherified hydroxy groups bound to the carbon skeleton
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

본 발명은 하기 식의 2-(4-(2-에톡시페닐)-6-(4-메톡시페닐)-1,3,5-트리아진-2-일)페놀을 포함하는 신규의 UV 흡수제에 관한 것이다:

Figure 112016084927517-pat00012

상기 식에서 R은 알킬 그룹이다. The present invention relates to novel UV absorbers comprising 2- (4- (2-ethoxyphenyl) -6- (4-methoxyphenyl) -1,3,5-triazin- Lt; / RTI >
Figure 112016084927517-pat00012

Wherein R is an alkyl group.

Description

고에너지 흡수성 UV 흡수제의 제조방법{The Preparation Method of UV absorbers} BACKGROUND OF THE INVENTION 1. Field of the Invention [0001] The present invention relates to a UV absorber,

본 발명은 고에너지 흡수성 UV 흡수제의 제조방법에 관한 것으로, 특히 차세대 고에너지 흡수성 UV 흡수제로 알려진 2-(4-(2-알콕시페닐)-6-(4-메톡시페닐)-1,3,5-트리아진-2-일)페놀의 제조방법에 관한 것이다. The present invention relates to a process for the preparation of high energy absorbing UV absorbers and more particularly to a process for the preparation of 2- (4- (2-alkoxyphenyl) -6- (4-methoxyphenyl) 5-triazin-2-yl) phenol.

하기에 도시된 S-트리아진은 고에너지 흡수성 UV 흡수제로 알려져 있고, 이 화합물은 중간체로서 o-히드록시 벤즈아미딘을 이용하게 된다. S-triazine, shown below, is known as a high energy absorbing UV absorber, which uses o -hydroxybenzamidine as an intermediate.

Figure 112016084927517-pat00001
Figure 112016084927517-pat00001

이러한 벤즈아미딘류의 제조방법으로는 벤조니트릴로부터 염화수소 가스를 이용하여 알킬 벤즈아미데이트를 제조하고, 이것을 암모니아 가스와 반응시켜 벤즈아미딘을 제조하는 방법이 있다. As a method for producing such benzamidines, there is a method of producing benzamidine by preparing alkylbenzamidate from benzonitrile using hydrogen chloride gas and reacting it with ammonia gas.

Figure 112016084927517-pat00002
Figure 112016084927517-pat00002

또한, 벤조니트릴과 NH2OH를 반응시켜 벤즈아미드옥심을 제조하고 여기에 수소가스를 사용하여 벤즈아미딘을 제조하는 방법이 있다. Further, there is a method of preparing benzamide oxime by reacting benzonitrile with NH 2 OH, and preparing benzamidine using hydrogen gas.

Figure 112016084927517-pat00003
Figure 112016084927517-pat00003

그러나, 이러한 방법들은 가스를 사용하여 위험 부담이 크고 장치 비용이 많이 드는 단점이 있었다. However, these methods have a disadvantage in that the use of gas causes a large risk and a high cost of the apparatus.

또, 상기의 S-트리아진 외에 더욱 높은 고에너지 흡수성의 차세대 UV 흡수제에 대한 요구가 지속적으로 있어왔다.In addition to the above-mentioned S-triazine, there has been a continuing need for a next generation UV absorber with higher energy absorption.

Chem. Pharm. Bull. 63, 33-37 (2015)Chem. Pharm. Bull. 63, 33-37 (2015) Chem. Eur. J. 2010, 16, 3510-3523Chem. Eur. J. 2010, 16, 3510-3523

따라서, 본 발명의 목적은 본 발명의 다른 목적은 신규의 차세대 UV 흡수제인 2-(4-(2-알콕시페닐)-6-(4-메톡시페닐)-1,3,5-트리아진-2-일)페놀을 포함하는 UV 흡수제를 제공하는 것이다. It is therefore an object of the present invention to provide a novel next generation UV absorber, 2- (4- (2-alkoxyphenyl) -6- (4-methoxyphenyl) -1,3,5-triazine- 2-yl) phenol. ≪ / RTI >

본 발명의 다른 목적은 알콕시 벤즈아미딘을 2-(4-메톡시-페닐)-벤조[e][1,3]옥사진-4-온과 반응시키는 것을 특징으로 하는 2-(4-(2-알콕시페닐)-6-(4-메톡시페닐)-1,3,5-트리아진-2-일)페놀의 제조방법을 제공하는 것이다. Another object of the present invention is to provide a process for the preparation of 2- (4- ((4-methoxy-phenyl) -benzo [ Alkoxyphenyl) -6- (4-methoxyphenyl) -1,3,5-triazin-2-yl) phenol.

상기 본 발명의 목적은 하기 식의 2-(4-(2-알콕시페닐)-6-(4-메톡시페닐)-1,3,5-트리아진-2-일)페놀을 포함하는 UV 흡수제에 의해 달성된다: The object of the present invention is to provide a UV absorber comprising 2- (4- (2-alkoxyphenyl) -6- (4-methoxyphenyl) -1,3,5-triazin- Lt; / RTI >

Figure 112016084927517-pat00004
Figure 112016084927517-pat00004

상기 식에서 R은 알킬 그룹이다. Wherein R is an alkyl group.

상기 본 발명의 목적은 또한 2-알콕시 벤즈아미딘을 2-(4-메톡시-페닐)-벤조[e][1,3]옥사진-4-온과 반응시키는 것을 특징으로 하는 2-(4-(2-알콕시페닐)-6-(4-메톡시페닐)-1,3,5-트리아진-2-일)페놀의 제조방법에 의해 달성된다. It is also an object of the present invention to provide a process for preparing 2- (4-methoxy-phenyl) -benzo [e] [1,3] oxazin- 4- (2-alkoxyphenyl) -6- (4-methoxyphenyl) -1,3,5-triazin-2-yl) phenol.

본 발명의 신규의 UV 흡수제는 높은 에너지 흡수성을 나타낸다. The novel UV absorbers of the present invention exhibit high energy absorbency.

도 1은 본 발명의 실시 예의 UV 흡수제의 UV 흡수 데이터BRIEF DESCRIPTION OF THE DRAWINGS Figure 1 shows UV absorption data

본 발명의 신규의 UV 흡수제의 원료인 2-알콕시 벤즈아미딘은 예를 들어 다음과 같은 방법으로 제조할 수 있다. The 2-alkoxybenzamidine which is a raw material of the novel UV absorber of the present invention can be produced, for example, by the following method.

우선 다음 반응식과 같이 2-알콕시 벤조니트릴을 아실클로라이드, 바람직하게는 아세틸 클로라이드 및 메탄올과 반응시켜 메틸 2-알콕시벤즈이미데이트를 제조하는 단계이다. 반응 온도는 15~25℃가 바람직하고, 반응시간은 18~48시간이 바람직하다. 2-알콕시 벤조니트릴과 반응하는 아세틸 클로라이드 및 메탄올은 각각 8당량, 12당량이 바람직하다. Alkoxybenzonitrile is reacted with an acyl chloride, preferably acetyl chloride and methanol, to prepare methyl 2-alkoxybenzimidate as follows. The reaction temperature is preferably 15 to 25 占 폚, and the reaction time is preferably 18 to 48 hours. Acetyl chloride and methanol reacting with 2-alkoxybenzonitrile are preferably 8 equivalents and 12 equivalents, respectively.

Figure 112016084927517-pat00005
Figure 112016084927517-pat00005

상기 식에서 R은 알킬 그룹이다. Wherein R is an alkyl group.

두 번째 단계는 다음 반응식과 같이 메틸 2-알콕시벤즈이미데이트를 염화암모늄과 반응시켜 2-알콕시 벤즈아미딘을 제조하는 것이다. 이 반응 역시 용매로는 메탄올, 에탄올 등의 알코올류가 바람직하고 메탄이 특히 바람직하다. 반응 온도는 50℃ 이상 메탄올 용매의 환류 온도로 하여 환류시키면서 반응시키는 경우 100%에 가까운 것이 전환율과 90% 이상의 수율을 얻을 수 있어 바람직하다. 메틸 2-알콕시벤즈이미데이트에 사용하는 염화암모늄의 양은 3당량 정도가 바람직하고, 용매의 양은 0.1M 내외로 충분하다. The second step is to react methyl 2-alkoxybenzimidate with ammonium chloride as shown in the following reaction scheme to prepare 2-alkoxybenzamidine. The reaction is also preferably an alcohol such as methanol or ethanol, particularly preferably methane. When the reaction is carried out while refluxing at a temperature of 50 ° C or higher and a reflux temperature of the methanol solvent, it is preferable that the reaction temperature is close to 100% and the conversion rate and the yield of 90% or more can be obtained. The amount of ammonium chloride used in the methyl 2-alkoxybenzimidate is preferably about 3 equivalents, and the amount of the solvent is preferably about 0.1M or so.

Figure 112016084927517-pat00006
Figure 112016084927517-pat00006

상기 식에서 R은 알킬 그룹이다.Wherein R is an alkyl group.

또, 2-알콕시 벤즈아미딘을 제조하는 다른 방법으로는 2-알콕시벤조니트릴을 NH2OH와 반응시켜 2-알콕시벤즈아미드 옥심을 제조하고, 2-알콕시벤즈아미드 옥심에 염화암모늄과 아연을 부가하여 2-알콕시벤즈아미딘을 제조하는 방법이 있다. Another method for producing 2-alkoxybenzamidine is to react a 2-alkoxybenzonitrile with NH 2 OH to prepare a 2-alkoxybenzamide oxime, and adding ammonium chloride and zinc to the 2-alkoxybenzamide oxime To prepare a 2-alkoxybenzamidine.

Figure 112016084927517-pat00007
Figure 112016084927517-pat00007

상기 식에서 R은 알킬 그룹이다.Wherein R is an alkyl group.

이 방법의 첫 번째 단계는 다음 반응식과 같이 2-알콕시 벤조니트릴을 NH2OH와 반응시켜 2-알콕시벤즈아미드 옥심을 제조하는 단계이다. NH2OH은 NH2OH·HCl 형태로 사용되며, 탄산나트륨과 용매가 사용되는데, 용매로는 메탄올, 에탄올, 이소프로필 알콜 등의 알코올류가 바람직하고 특히 메탄올이 바람직하다. 반응 온도는 용매의 환류 온도로 하여 환류시키면서 반응시키는 것이 바람직하다. 제조된 2-알콕시벤즈아미드 옥심은 여과하고 에탄올로 세정하는 것이 바람직하다. 2-알콕시벤조니트릴에 부가되는 NH2OH·HCl과 탄산나트륨의 당량은 각각 2~4당량, 1~2당량이 바람직하며, 알코올 용매는 1~1.16M의 양으로 사용되는 것이 바람직하다. The first step of this process is to react the 2-alkoxybenzonitrile with NH 2 OH to produce a 2-alkoxybenzamide oxime as shown in the following reaction scheme. NH 2 OH is used in the form of NH 2 OH · HCl, and sodium carbonate and a solvent are used. As the solvent, alcohols such as methanol, ethanol and isopropyl alcohol are preferable, and methanol is particularly preferable. The reaction is preferably carried out while refluxing to the reflux temperature of the solvent. The 2-alkoxybenzamide oxime thus prepared is preferably filtered and washed with ethanol. The equivalents of NH 2 OH · HCl and sodium carbonate added to 2-alkoxybenzonitrile are preferably 2 to 4 equivalents and 1 to 2 equivalents, respectively, and the alcohol solvent is preferably used in an amount of 1 to 1.16M.

Figure 112016084927517-pat00008
Figure 112016084927517-pat00008

상기 식에서 R은 알킬 그룹이다.Wherein R is an alkyl group.

두 번째 단계는 다음 반응식과 같이 2-알콕시벤즈아미드 옥심을 염화암모늄, 아연과 반응시키는 것이다. 이 반응 역시 용매로는 메탄올, 에탄올 등의 알코올류가 바람직하고 메탄올과 에탄올의 혼합 용매가 특히 바람직하다. 반응 온도는 용매의 환류 온도로 하여 환류시키면서 반응시키는 것이 바람직하다. 2-알콕시벤즈아미드 옥심과 반응하는 아연과 염화암모늄의 당량은 각각 1~4당량, 4~8당량이 바람직하다. 용매의 양은 0.1~0.7M 범위가 바람직하고, 메탄올과 에탄올 혼합 용매를 사용하는 경우 메탄올:에탄올의 비는 1.5:1이 바람직하다. The second step is to react the 2-alkoxybenzamide oxime with ammonium chloride, zinc, as shown in the following reaction scheme. The reaction is also preferably an alcohol such as methanol or ethanol, or a mixed solvent of methanol and ethanol is particularly preferable. The reaction is preferably carried out while refluxing to the reflux temperature of the solvent. The equivalents of zinc and ammonium chloride reacting with the 2-alkoxybenzamide oxime are preferably 1 to 4 equivalents and 4 to 8 equivalents, respectively. The amount of the solvent is preferably in the range of 0.1 to 0.7 M, and when the mixed solvent of methanol and ethanol is used, the ratio of methanol: ethanol is preferably 1.5: 1.

Figure 112016084927517-pat00009
Figure 112016084927517-pat00009

상기 식에서 R은 알킬 그룹이다.Wherein R is an alkyl group.

2-알콕시 벤즈아미딘을 2-(4-메톡시-페닐)-벤조[e][1,3]옥사진-4-온과 반응시켜 2-(4-(2-알콕시페닐)-6-(4-메톡시페닐)-1,3,5-트리아진-2-일)페놀을 제조할 수 있다. Alkoxybenzamidine is reacted with 2- (4-methoxy-phenyl) -benzo [e] [1,3] oxazin-4- (4-methoxyphenyl) -1,3,5-triazin-2-yl) phenol.

이러한 알콕시 벤즈아미딘은, 바람직하게는 예를 들어 2-에톡시 벤즈아미딘이고, 2-에톡시 벤즈아미딘을 이용하여 2-(4-메톡시-페닐)-벤조[e][1,3]옥사진-4-온과 반응시켜 차세대 UV 흡수제인 (2-(4-(2-에톡시페닐)-6-(4-메톡시페닐)-1,3,5-트리아진-2-일)페놀을 합성할 수 있다. Such alkoxybenzamidines are preferably, for example, 2-ethoxybenzamidine and 2- (4-methoxy-phenyl) -benzo [e] [1, 3] oxazin-4-one to give the next generation UV absorber, 2- (4- (2-ethoxyphenyl) -6- (4- methoxyphenyl) A) phenol can be synthesized.

이하 실시 예를 통해 본 발명을 더욱 상세하게 설명한다. Hereinafter, the present invention will be described in more detail with reference to examples.

실시 예 1 Example 1

2-(4-(2-에톡시페닐)-6-(4-메톡시페닐)-1,3,5-트리아진-2-일)페놀의 합성 Synthesis of 2- (4- (2-ethoxyphenyl) -6- (4-methoxyphenyl) -1,3,5-triazin-2-yl) phenol

Figure 112016084927517-pat00010
Figure 112016084927517-pat00010

1L 4-구 둥근 바닥 플라스크에 크실렌 30mL와 p-아니솔일 클로라이드 37g(0.22mol, 2.0당량), 살리실아미드 15g(0.11mol)을 가하고 140±2℃로 승온하고 5시간 유지하여 2-(4-메톡시-페닐)-벤조[e][1,3]옥사진-4-온 화합물 합성하였고 반응완료는 HPLC를 통하여 확인하였다. 이 반응 결과물의 온도를 60℃ 이하로 냉각한 후,( 80℃ 이하에서 굳는 현상 발생) MeOH 350mL를 빠른 속도로 가하고 30℃이하의 온도에서 생성된 옥사진 화합물의 분산되도록 충분히 교반하였다,(약 1시간) (0.22 mol, 2.0 equivalents) of p-anisole chloride and 15 g (0.11 mol) of salicylamide were added to a 1 L four-necked round bottom flask, and the temperature was raised to 140 ± 2 ° C. and maintained for 5 hours to obtain 2- -Methoxy-phenyl) -benzo [e] [1,3] oxazin-4-one were synthesized and the completion of the reaction was confirmed by HPLC. After the temperature of the reaction product was cooled to 60 ° C or lower, 350 ml of MeOH was added at a rapid rate (hardening occurred at 80 ° C or lower), and sufficiently stirred to disperse the oxazine compound produced at a temperature of 30 ° C or lower 1 hours)

덩어리가 없이 분산된 반응물에 2-에톡시 벤즈아미딘 하이드로클로라이드를 살리실아미드와 같은 몰 수인 22.0g을 투입하여 30분간 더 교반한 후, 98% NaOH 11g(0.28mol, 2.5 eq.)를 가하였다. 이 반응 혼합물의 온도를 63±2℃에서 2시간 동안 반응한 후, 실온까지 냉각하였다. 여과 및 수세 과정을 거쳐 밝고 연한 노란색의 2-(4-(2-에톡시페닐)-6-(4-메톡시페닐)-1,3,5-트리아진-2-일)페놀 화합물 26.3g(수율 60%) 얻었다. UV 흡수 데이터를 도 1에 게시하였다. 22.0 g of the same molar amount as that of salicylamide was added to the reaction mixture dispersed without agglomeration, stirred for 30 minutes, and then 11 g (0.28 mol, 2.5 eq.) Of 98% NaOH was added thereto Respectively. The reaction mixture was allowed to react at 63 ± 2 ° C for 2 hours and then cooled to room temperature. Filtered and washed to obtain 26.3 g of 2- (4- (2-ethoxyphenyl) -6- (4-methoxyphenyl) -1,3,5-triazin-2-yl) (Yield: 60%). UV absorbance data are shown in Fig.

순도(HPLC로 확인) : 99.4% Purity (confirmed by HPLC): 99.4%

1H NMR(300MHz, CDCl3) δ = 8.73(d, 1H), 8.64(t, 2H), 7.62(t, 1H), 7.61(t, 1H), 7.58(t, 1H), 7.50(t, 1H), 7.09(d, 1H), 7.06(d 1H), 7.03(d, 1H), 7.02(d 1H), 3.94(s, 3H) 1 H NMR (300MHz, CDCl 3 ) δ = 8.73 (d, 1H), 8.64 (t, 2H), 7.62 (t, 1H), 7.61 (t, 1H), 7.58 (t, 1H), 7.50 (t, 7.09 (d, IH), 7.09 (d, IH), 7.09 (d,

FT-IR(Neat) : 3500(OH), 2964, 2924, 2870(CH), 1606(C=C), 1506, 1230(CO) cm-1 FT-IR (Neat): 3500 (OH), 2964, 2924, 2870 (CH), 1606 (C = C), 1506, 1230 (CO) cm -1

Claims (4)

삭제delete 삭제delete 2-알콕시 벤즈아미딘을 2-(4-메톡시-페닐)-벤조[e][1,3]옥사진-4-온과 반응시키는 것을 특징으로 하는 2-(4-(2-알콕시페닐)-6-(4-메톡시페닐)-1,3,5-트리아진-2-일)페놀의 제조방법.
2- (4- (2-alkoxyphenyl) -benzo [e] [1,3] oxazin-4-one characterized in that 2-alkoxybenzamidine is reacted with 2- ) -6- (4-methoxyphenyl) -1,3,5-triazin-2-yl) phenol.
제3항에 있어서, 2-알콕시 벤즈아미딘은 2-에톡시 벤즈아미딘인 것을 특징으로 하는 2-(4-(2-에톡시페닐)-6-(4-메톡시페닐)-1,3,5-트리아진-2-일)페놀의 제조방법.



4. The compound according to claim 3, wherein the 2-alkoxybenzamidine is 2- (4- (2-ethoxyphenyl) -6- (4-methoxyphenyl) 3,5-triazin-2-yl) phenol.



KR1020160111739A 2016-08-31 2016-08-31 The Preparation Method of UV absorbers KR101877251B1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
KR1020160111739A KR101877251B1 (en) 2016-08-31 2016-08-31 The Preparation Method of UV absorbers

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
KR1020160111739A KR101877251B1 (en) 2016-08-31 2016-08-31 The Preparation Method of UV absorbers

Publications (2)

Publication Number Publication Date
KR20180024829A KR20180024829A (en) 2018-03-08
KR101877251B1 true KR101877251B1 (en) 2018-07-11

Family

ID=61725851

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1020160111739A KR101877251B1 (en) 2016-08-31 2016-08-31 The Preparation Method of UV absorbers

Country Status (1)

Country Link
KR (1) KR101877251B1 (en)

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2303548A (en) * 1995-07-22 1997-02-26 Ciba Geigy Ag Solutions of UV absorbing 1,3,5 triazines

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2303548A (en) * 1995-07-22 1997-02-26 Ciba Geigy Ag Solutions of UV absorbing 1,3,5 triazines

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
영국 특허공고 제2303548호(1997.02.26.) 1부. *

Also Published As

Publication number Publication date
KR20180024829A (en) 2018-03-08

Similar Documents

Publication Publication Date Title
AU2018250429B2 (en) Method for preparing azoxystrobin
EP1873151B1 (en) Improved process for producing moxonidine
KR101877251B1 (en) The Preparation Method of UV absorbers
CN113072436A (en) Preparation method of benzyl aryl ether
EP3199526A1 (en) Intermediate for use in synthesizing paroxetine, preparation method for the intermediate, and uses thereof
CN113549051A (en) Synthesis method of bisamide insecticide
KR101569571B1 (en) Method for synthesis of organic carbonates
JP6224529B2 (en) Method for producing polyhydroxyurethane
KR101363595B1 (en) Products from Reactions of Hydrazine Derivatives with Carbon Dioxide
CN113185469B (en) Method for modifying photoregulated diaryl dihydrophenazine
KR20180024824A (en) The Preparation Method of UV absorbers and intermediates thereof
CN115108912A (en) Strongly alkaline ionic liquid catalyzed CO 2 Method for synthesizing dimethyl carbonate catalyst
KR20180024823A (en) The Preparation Method of UV absorber intermediates
KR101529507B1 (en) Di(aminoguanidium) 4,4',5,5'-tetranitro-2,2'-biimidazole, and preparation method thereof
CN105153039A (en) Preparation method for rosuvastatin calcium intermediate impurity
KR100744824B1 (en) Synthetic method of dialkylcarbonates
KR101716255B1 (en) Method for producing 4,6-dialkoxy-2-cyanomethylpyrimidine and synthetic intermediate thereof
JP2007091743A (en) Method for coupling benzyl amine with haloaromatic compound
KR101585030B1 (en) Preparing method of hydrizide compounds
CN106916103B (en) Preparation method of 2-phenylquinoline compound
KR101483445B1 (en) Producing method of nitrogen-containing organic compound
JP7434783B2 (en) Method for producing N-methylisocyanuric acid
KR101496681B1 (en) N-substituted 3, 3- dinitroazetidine energetic plasticizer and preparation method thereof
CN101343213B (en) Allyl ether series compound and preparation thereof
CN108586369B (en) Process for producing phenyltriazine compound and process for producing phenylpyridine compound

Legal Events

Date Code Title Description
A201 Request for examination
E902 Notification of reason for refusal
E701 Decision to grant or registration of patent right
GRNT Written decision to grant