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WO2003104182A1 - 2-alkoxyalkyl-2-adamantyl (meth)acrylate and method for preparing same - Google Patents

2-alkoxyalkyl-2-adamantyl (meth)acrylate and method for preparing same Download PDF

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Publication number
WO2003104182A1
WO2003104182A1 PCT/KR2003/001151 KR0301151W WO03104182A1 WO 2003104182 A1 WO2003104182 A1 WO 2003104182A1 KR 0301151 W KR0301151 W KR 0301151W WO 03104182 A1 WO03104182 A1 WO 03104182A1
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Prior art keywords
alkoxyalkyl
adamantyl
meth
acrylate
adamantanol
Prior art date
Application number
PCT/KR2003/001151
Other languages
French (fr)
Inventor
Eun Hyoung Bae
Young Bae Song
Dong Ju Oh
Original Assignee
Enf Technology Co., Ltd.
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Publication date
Application filed by Enf Technology Co., Ltd. filed Critical Enf Technology Co., Ltd.
Priority to AU2003232680A priority Critical patent/AU2003232680A1/en
Publication of WO2003104182A1 publication Critical patent/WO2003104182A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
    • C07C69/533—Monocarboxylic acid esters having only one carbon-to-carbon double bond
    • C07C69/54—Acrylic acid esters; Methacrylic acid esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/14—Preparation of carboxylic acid esters from carboxylic acid halides
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
    • G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
    • G03F7/0397—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition the macromolecular compound having an alicyclic moiety in a side chain
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/56—Ring systems containing bridged rings
    • C07C2603/58—Ring systems containing bridged rings containing three rings
    • C07C2603/70—Ring systems containing bridged rings containing three rings containing only six-membered rings
    • C07C2603/74—Adamantanes

Definitions

  • the present invention relates to a novel adamantane derivative, 2- alkoxyalkyl-2-adamantyl (meth)acrylate, and a method for preparing same.
  • Adamantane derivatives having a vinyl substituent have been used in the production of photocurable resins having excellent optical and mechanical properties suitable for applications in such fields as adhesive, printing ink, photosensitive resin, and optical fiber coat.
  • Japanese Laid-open Patent Publication No. Hei9-73173 discloses 2-adamantyl (meth)acrylate useful for the production of chemical amplification resist; and European Laid-open Patent Publication No. 1 000 924 Al, an acid-sensitive polymer having adamantyl moieties which has sufficiently high etching resistance for providing a finer line pattern.
  • Adamantyl derivatives have also been used as drug intermediates.
  • 6,127,415 discloses apoptosis-inducing adamantyl derivatives and their usage as antitumor agents; and Korean Laid-open Patent Publication No. 1997-42511, a pharmaceutical composition comprising an adamantyl derivative which is active against dermatological diseases.
  • adamantane derivative which is useful as a monomer for the production of a photocurable resin or as a drug intermediate. It is another object of the present invention to provide a method for preparing the adamantine derivative.
  • FIG. 1 an FT-IR spectrum of 2-(4-methoxybutyl)-2-adamantanol produced in Example 1 of the present invention
  • FIG. 2 an NMR spectrum of 2-(4-methoxybutyl)-2-adamantyl acrylate produced in Example 1 of the present invention.
  • FIG. 3 an NMR spectrum of 2-(4-methoxybutyl)-2-adamantyl methacrylate produced in Example 2 of the present invention.
  • 2-alkoxyalkyl-2-adamantyl (meth)acrylate represented by the following formula I:
  • R 1 9 wherein, is hydrogen, C w alkyl or C 3 . 8 cycloalkyl; R is hydrogen or methyl; and n is an integer.
  • R 1 is methyl and n is an integer in the range of 1 to 4.
  • the inventive 2-adamantyl (meth)acrylate is useful as a resist material suitable for short-wave exposure source (ArF excimer laser) since it is an acid- sensitive compound containing an alkali-soluble group protected with an alicyclic hydrocarbon group.
  • a method of preparing the compound of formula I comprising: a) reacting 2-adamantanone with a Grignard reagent of formula R 1 0(CH 2 ) n MgX to obtain a 2-alkoxyalkyl-2-adamantanol, the alkoxyalkyl being R 1 0(CH 2 ) n -; and b) reacting the 2-alkoxyalkyl-2-adamantanol with (meth)acryloyl chloride to obtain 2-alkoxyalkyl-2-adamantyl (meth)acrylate, wherein X is chlorine or bromine.
  • step b) is performed in the presence of a basic reagent.
  • the method of preparing the compound may further comprise a step of reacting alkoxyalkyl halide with magnesium to obtain alkoxyalkyl Grignard reagent before step a).
  • a separation process may be performed after each step is completed.
  • the separation process may be performed after all steps are performed in situ. Accordingly, synthesized Grignard reagent may be employed in step a) without further separation.
  • an alkoxyalkyl halide is reacted with magnesium to synthesize an alkoxyalkyl magnesium halide (an alkoxyalkyl reagent):
  • O' XT X (1)
  • R 1 is hydrogen, C ⁇ alkyl or C 3 . 8 cycloalkyl; X is Cl or Br; and n is an integer.
  • reaction scheme (2) adamantanone and the alkoxyalkyl Grignard reagent are reacted, to synthesize a 2-alkoxyalkyl-2-adamantanol:
  • R 1 and n are the same as defined above.
  • R 1 , R 2 and n are the same as defined above.
  • the alkoxyalkyl Grignard reagent is employed preferably in an amount ranging from 1.2 to 2.0 equivalents based on the amount of 2-adamantanone, and (meth)acryloyl chloride is employed preferably in an amount ranging from 1.2 to 2.0 mole per mole of 2-alkoxyalkyl-2-adamantanol.
  • the basic reagent that may be used in the present invention is a tertiary amine such as triethyl amine or pyridine and is employed in an amount ranging from 1.4 to 2.2 mole per mole of 2-alkoxyalkyl-2-adamantanol.
  • the reaction for synthesizing 2-alkoxyalkyl-2-adamantanol is performed at a temperature ranging from -20 to 0°C, for a period ranging from 2 to 3 hours; and the reaction for synthesizing 2-alkoxyal-kyl-2-adamantyl (meth)acrylate, at a temperature ranging from -20 to 0 °C , for a period ranging from 2 to 15 hours.
  • the present invention is described in more detail below by referring to the following Examples, and the Examples are given for the purpose of illustration only, and are not intended to limit the scope of the invention.
  • 2-Alkoxyalkyl-2-adamantyl (meth)acrylate according to the present invention can be used for various applications e.g. as a monomer of a photocurable resin, a drug intermediate and the like. Also, the inventive method for preparing 2-alkoxyalkyl-2-adamantyl (meth)acrylate is simple, a high yield process suitable for commercial-scale production.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • General Physics & Mathematics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

2-Alkoxyalkyl-2-adamantyl (meth)acrylate and a method for preparing same are provided.

Description

2-ALKOXYALKYL-2-ADAMANTYL (METH)ACRYLATE AND METHOD FOR PREPARING SAME
Field of the Invention
The present invention relates to a novel adamantane derivative, 2- alkoxyalkyl-2-adamantyl (meth)acrylate, and a method for preparing same.
Background of the Invention
Adamantane derivatives having a vinyl substituent have been used in the production of photocurable resins having excellent optical and mechanical properties suitable for applications in such fields as adhesive, printing ink, photosensitive resin, and optical fiber coat. For example, Japanese Laid-open Patent Publication No. Hei9-73173 discloses 2-adamantyl (meth)acrylate useful for the production of chemical amplification resist; and European Laid-open Patent Publication No. 1 000 924 Al, an acid-sensitive polymer having adamantyl moieties which has sufficiently high etching resistance for providing a finer line pattern. Adamantyl derivatives have also been used as drug intermediates. For example, US. patent No. 6,127,415 discloses apoptosis-inducing adamantyl derivatives and their usage as antitumor agents; and Korean Laid-open Patent Publication No. 1997-42511, a pharmaceutical composition comprising an adamantyl derivative which is active against dermatological diseases.
Summary of the Invention
Accordingly, it is an object of the present invention to provide a novel adamantane derivative which is useful as a monomer for the production of a photocurable resin or as a drug intermediate. It is another object of the present invention to provide a method for preparing the adamantine derivative.
Brief Description of the Drawings
The above and other objects and features of the present invention will become apparent from the following description of the invention taken in conjunction with the following accompanying drawings, which respectively show: FIG. 1 : an FT-IR spectrum of 2-(4-methoxybutyl)-2-adamantanol produced in Example 1 of the present invention;
FIG. 2 : an NMR spectrum of 2-(4-methoxybutyl)-2-adamantyl acrylate produced in Example 1 of the present invention; and
FIG. 3 : an NMR spectrum of 2-(4-methoxybutyl)-2-adamantyl methacrylate produced in Example 2 of the present invention.
Detailed Description of the Invention
In accordance with one aspect of the present invention, there is provided 2-alkoxyalkyl-2-adamantyl (meth)acrylate represented by the following formula I:
Figure imgf000003_0001
1 9 wherein, is hydrogen, Cw alkyl or C3.8 cycloalkyl; R is hydrogen or methyl; and n is an integer. Preferably, R1 is methyl and n is an integer in the range of 1 to 4.
The inventive 2-adamantyl (meth)acrylate is useful as a resist material suitable for short-wave exposure source (ArF excimer laser) since it is an acid- sensitive compound containing an alkali-soluble group protected with an alicyclic hydrocarbon group.
In accordance with another aspect of the present, there is provided a method of preparing the compound of formula I comprising: a) reacting 2-adamantanone with a Grignard reagent of formula R10(CH2)nMgX to obtain a 2-alkoxyalkyl-2-adamantanol, the alkoxyalkyl being R10(CH2)n-; and b) reacting the 2-alkoxyalkyl-2-adamantanol with (meth)acryloyl chloride to obtain 2-alkoxyalkyl-2-adamantyl (meth)acrylate, wherein X is chlorine or bromine.
Preferably, step b) is performed in the presence of a basic reagent. In accordance with a preferred embodiment of the present invention, the method of preparing the compound may further comprise a step of reacting alkoxyalkyl halide with magnesium to obtain alkoxyalkyl Grignard reagent before step a).
In the preparation method of the compound according to the present invention, a separation process may be performed after each step is completed.
However, the separation process may be performed after all steps are performed in situ. Accordingly, synthesized Grignard reagent may be employed in step a) without further separation.
A process for producing 2-alkoxyalkyl-2-adamantyl (meth)acrylate according to the present invention will now be described in detail.
As shown in reaction scheme (1), an alkoxyalkyl halide is reacted with magnesium to synthesize an alkoxyalkyl magnesium halide (an alkoxyalkyl reagent): R1 >(CH2)nX + Mg R\ ■ (CH2)nMg. O' XT X (1)
wherein, R1 is hydrogen, Cμ alkyl or C3.8 cycloalkyl; X is Cl or Br; and n is an integer.
Next, as shown in reaction scheme (2), adamantanone and the alkoxyalkyl Grignard reagent are reacted, to synthesize a 2-alkoxyalkyl-2-adamantanol:
wherein, R1 and n are the same as defined above.
Finally, as shown in reaction scheme (3), the 2-alkoxyalkyl-2- adamantanol is reacted with acryloyl or methacryloyl chloride to obtain 2- alkoxyalkyl-2-adamantyl (meth)acrylate:
Figure imgf000005_0002
wherein, R1, R2 and n are the same as defined above.
The alkoxyalkyl Grignard reagent is employed preferably in an amount ranging from 1.2 to 2.0 equivalents based on the amount of 2-adamantanone, and (meth)acryloyl chloride is employed preferably in an amount ranging from 1.2 to 2.0 mole per mole of 2-alkoxyalkyl-2-adamantanol.
Preferably, the basic reagent that may be used in the present invention is a tertiary amine such as triethyl amine or pyridine and is employed in an amount ranging from 1.4 to 2.2 mole per mole of 2-alkoxyalkyl-2-adamantanol. In accordance with a preferred embodiment of the present invention, the reaction for synthesizing 2-alkoxyalkyl-2-adamantanol is performed at a temperature ranging from -20 to 0°C, for a period ranging from 2 to 3 hours; and the reaction for synthesizing 2-alkoxyal-kyl-2-adamantyl (meth)acrylate, at a temperature ranging from -20 to 0 °C , for a period ranging from 2 to 15 hours. The present invention is described in more detail below by referring to the following Examples, and the Examples are given for the purpose of illustration only, and are not intended to limit the scope of the invention.
Example 1: Preparation of 2-(4-methoxybutyl -2-adamantyl acrylate
A. Synthesis of 4-methoxybutyl magnesium chloride (4-methoxybutyl Grignard reagent)
52 g of 4-methoxy-l-butanol (0.5 mol) and 40 g of pyridine (0.5 mol) were placed into a 1 liter three-necked flask and then cooled to 0°C . Thionyl chloride (119 g, 1.0 mol) was added slowly thereto using a dropping funnel. The mixture was refluxed for about 1 hour, after poured into water to destroy completion of the reaction, excess thionyl chloride extracted with 300 ml of methylene chloride. Then, the organic layer was washed with 5% sodium hydroxide and dried over magnesium sulfate to obtain 4-methoxybutyl chloride (yield: 80%).
26.7 g of magnesium turnings (1.1 mol) was dispersed in 500ml of anhydrous THF, and then, a small amount of iodine and a drop of 4- methoxybutyl chloride were added thereto, followed by heating up to 40 °C to activate magnesium. After the color of the solution changed from brown to colorless, the mixture was cooled and then 108.57 g of the 4-methoxybutyl chloride (1.0 mol) was added slowly thereto. After completion of the addition, the reaction mixture was warmed, and refluxed for about 1 hour to obtain a 4- methoxybutylmagnesium chloride solution.
B. Synthesis of 2-(4-methoxybutyl)-2-adamantanol
The 4-methoxybutylmagnesium chloride solution obtained in step A in an amount corresponding to 1.0 mole of 4-methoxybutyl chloride was placed in a 1 liter flask using a cannular and cooled to 0°C . 120.17 g of 2-adamantanone (0.8 mol) was added slowly thereto using a dropping funnel, and stirred at room temperature for about 12 hours. After completion of the reaction, excess THF was removed using a rotary evaporator, the resulting residue was poured into water, the solution was neutralized with dilute sulfuric acid, extracted using diethyl ether, and dried over magnesium sulfate. The crude product was re- crystallized from n-hexane-methylene chloride to obtain 2-(4-methoxybutyl)-2- adamantanol (yield: 80 %).
FT-IR (KBr; cm 1): 3431, 2902, 1449.5, 1112.5, 941.5, 611.
C. Synthesis of 2-(4-methoxybutyl)-2-adamantyl acrylate
44.87 g of the 2-(4-methoxybutyl)-2-adamantanol (0.2 mol) obtained in step B and 32.38 g of triethylamine (0.32 mol) were dissolved in 300 ml of THF and then 25.34 g of acryloyl chloride (0.28 mol) was added slowly thereto using a dropping funnel. Then, the reaction was stirred at room temperature for about 12 hours.
After completion of the reaction, excess THF was removed using a rotary evaporator, and the resulting mixture was poured into water. The solution was neutralized with dilute sulfuric acid, extracted using diethyl ether, and the ether layer was dried over magnesium sulfate. After removing diethyl ether, the crude product was vacuum distilled to obtain 2-(4-methoxybutyl)-2- adamantyl acrylate (yield: 80%). 1H-NMR (CDC13; ppm): 6.25(1H, d), 6.1(1H, dd), 5.9(1H, d), 3.3(2H, t), 3.2(3H, S), 2.3-1.2(m).
Example 2: Preparation of 2-(4-methoxybutyl)-2-adamantyl methacrylate
The title compound was prepared in the same manner as in Example 1, except that 29.27 g of methacryloyl chloride (0.28 mol) was used instead of 25.34 g of acryloyl chloride (yield: 85%).
H-NMR (CDC13; ppm): 6.1(1H, d), 5.5(1H, d), 3.3(2H, t), 3.2(3H, S), 2.3-1.2(m).
2-Alkoxyalkyl-2-adamantyl (meth)acrylate according to the present invention can be used for various applications e.g. as a monomer of a photocurable resin, a drug intermediate and the like. Also, the inventive method for preparing 2-alkoxyalkyl-2-adamantyl (meth)acrylate is simple, a high yield process suitable for commercial-scale production.
While the invention has been described with respect to the above specific embodiments, it should be recognized that various modifications and changes may be made to the invention by those skilled in the art which also fall within the scope of the invention as defined by the appended claims.

Claims

What is claimed is :
1. A compound of formula I:
Figure imgf000009_0001
wherein, R1 is hydrogen, C^ alkyl or C3.8 cycloalkyl; R2 is hydrogen or methyl; and n is an integer.
2. The compound of claim 1 , wherein n is an integer in the range of 1 to 4.
3. A method of preparing the compound of claim 1 , comprising:
a) reacting 2-adamantanone with a Grignard reagent of formula R10(CH2)nMgX to obtain a 2-alkoxyalkyl-2-adamantanol, the alkoxyalkyl being R10(CH2)n-; and b) reacting the 2-alkoxyalkyl-2-adamantanol with (meth)acryloyl chloride to obtain 2-alkoxyalkyl-2-adamantyl (meth)acrylate, wherein X is chlorine or bromine.
4. The method of claim 3, wherein step b) is performed in the presence of a basic reagent.
5. The method of claim 3, wherein in step a) 2-alkoxyalkyl-2-adamantanol is 2-(4-methoxybutyl)-2-adamantanol.
PCT/KR2003/001151 2002-06-11 2003-06-11 2-alkoxyalkyl-2-adamantyl (meth)acrylate and method for preparing same WO2003104182A1 (en)

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Cited By (5)

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Publication number Priority date Publication date Assignee Title
WO2006002691A1 (en) * 2004-07-07 2006-01-12 Lundbeck Pharmaceuticals Italy S.P.A. Process for the synthesis and purification of (4-methoxybutyl) (4-trifluoromethylphenyl)methanone
JP2006063061A (en) * 2004-03-10 2006-03-09 Idemitsu Kosan Co Ltd Adamantane derivative and method for producing the same
EP1876209A1 (en) * 2006-07-03 2008-01-09 FUJIFILM Corporation Ink composition, inkjet recording method, printed material, and process for producing lithographic printing plate
EP1712542A4 (en) * 2004-02-05 2008-01-16 Idemitsu Kosan Co ADAMANTAN DERIVATIVES AND METHOD FOR THE PRODUCTION THEREOF
US8128746B2 (en) 2006-09-14 2012-03-06 Fujifilm Corporation Ink composition, ink jet recording method, method for producing planographic printing plate, and planographic printing plate

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CN111056945A (en) * 2019-12-25 2020-04-24 上海博栋化学科技有限公司 Photoresist resin monomer synthesized from spiro [5.5] undecane-3, 9-dione and synthesis method thereof

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EP1020767A1 (en) * 1999-01-18 2000-07-19 Sumitomo Chemical Company, Limited Chemical amplification type positive resist composition
US6222061B1 (en) * 2000-02-19 2001-04-24 Chem Search Corp. 2-alkyl-2-adamantyl 5-norbornene-2-carboxylates and method of producing the same
KR20010081855A (en) * 2000-02-19 2001-08-29 김동석 Producing method for 2-alkyl-2-adamantyl (meth)acrylates
EP1127870A1 (en) * 2000-02-26 2001-08-29 Shipley Company LLC Novel monomers, polymers, methods of synthesis thereof and photoresist compositions

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US6013416A (en) * 1995-06-28 2000-01-11 Fujitsu Limited Chemically amplified resist compositions and process for the formation of resist patterns
EP1020767A1 (en) * 1999-01-18 2000-07-19 Sumitomo Chemical Company, Limited Chemical amplification type positive resist composition
US6222061B1 (en) * 2000-02-19 2001-04-24 Chem Search Corp. 2-alkyl-2-adamantyl 5-norbornene-2-carboxylates and method of producing the same
KR20010081855A (en) * 2000-02-19 2001-08-29 김동석 Producing method for 2-alkyl-2-adamantyl (meth)acrylates
EP1127870A1 (en) * 2000-02-26 2001-08-29 Shipley Company LLC Novel monomers, polymers, methods of synthesis thereof and photoresist compositions

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1712542A4 (en) * 2004-02-05 2008-01-16 Idemitsu Kosan Co ADAMANTAN DERIVATIVES AND METHOD FOR THE PRODUCTION THEREOF
US7528279B2 (en) 2004-02-05 2009-05-05 Idemitsu Kosan Co., Ltd. Adamantane derivatives and process for producing the same
JP2006063061A (en) * 2004-03-10 2006-03-09 Idemitsu Kosan Co Ltd Adamantane derivative and method for producing the same
WO2006002691A1 (en) * 2004-07-07 2006-01-12 Lundbeck Pharmaceuticals Italy S.P.A. Process for the synthesis and purification of (4-methoxybutyl) (4-trifluoromethylphenyl)methanone
EP1876209A1 (en) * 2006-07-03 2008-01-09 FUJIFILM Corporation Ink composition, inkjet recording method, printed material, and process for producing lithographic printing plate
EP1975213A1 (en) * 2006-07-03 2008-10-01 FUJIFILM Corporation Ink composition, injet recording method, printed material, and process for producing lithographic printing plate
US7553605B2 (en) 2006-07-03 2009-06-30 Fujifilm Corporation Ink composition, inkjet recording method, printed material, and process for producing lithographic printing plate
US8128746B2 (en) 2006-09-14 2012-03-06 Fujifilm Corporation Ink composition, ink jet recording method, method for producing planographic printing plate, and planographic printing plate

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