WO2005095467A1 - Terpolymere acrylate/methacrylate desodorise et procede de desodorisation correspondant - Google Patents

Terpolymere acrylate/methacrylate desodorise et procede de desodorisation correspondant Download PDF

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Publication number
WO2005095467A1
WO2005095467A1 PCT/JP2005/006386 JP2005006386W WO2005095467A1 WO 2005095467 A1 WO2005095467 A1 WO 2005095467A1 JP 2005006386 W JP2005006386 W JP 2005006386W WO 2005095467 A1 WO2005095467 A1 WO 2005095467A1
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WO
WIPO (PCT)
Prior art keywords
terpolymer
methacrylate
lower alkyl
acrylate
water
Prior art date
Application number
PCT/JP2005/006386
Other languages
English (en)
Japanese (ja)
Inventor
Katsumi Shimizu
Hisayuki Saito
Atsushi Itou
Original Assignee
Kobayashi Pharmaceutical Co., Ltd.
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 Kobayashi Pharmaceutical Co., Ltd. filed Critical Kobayashi Pharmaceutical Co., Ltd.
Publication of WO2005095467A1 publication Critical patent/WO2005095467A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K6/00—Preparations for dentistry
    • A61K6/80—Preparations for artificial teeth, for filling teeth or for capping teeth
    • A61K6/884—Preparations for artificial teeth, for filling teeth or for capping teeth comprising natural or synthetic resins
    • A61K6/887—Compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds

Definitions

  • the present invention relates to a deodorized atalylate Z-metharylate terpolymer and a method for deodorizing the same.
  • Athalylate Z-metharylate-based terpolymer for example, Eudragit (registered trademark) has a property of dissolving at a predetermined pH, and is therefore widely used as a coating agent for enteric pharmaceutical preparations (Patent Document 1, 2).
  • the atalylate Z-metharylate terpolymer has the effect of promoting the exfoliation of denture backing agents (denture stabilizing agents for stabilizing dentures into the oral mucosa and mucosal preparations) from the oral mucosa.
  • denture backing agents denture stabilizing agents for stabilizing dentures into the oral mucosa and mucosal preparations
  • it is also used as a peelability improver for denture lining agents (Patent Document 3).
  • an atalylate Z-metharylate-based terpolymer such as Eudragit (registered trademark)
  • Eudragit registered trademark
  • Patent Document 1 JP 2001-31591
  • Patent Document 2 JP 2004-35518
  • Patent Document 3 Japanese Patent Publication No. 7-42210
  • An object of the present invention is to reduce the odor peculiar to the atalylate Z-metharylate-based terpolymer and to improve the usability.
  • the present invention provides the following terpolymer deodorizing method, a deodorized terpolymer, and a denture lining agent containing the terpolymer.
  • Item 1 A terpolymer comprising lower alkyl acrylate, lower alkyl methacrylate and methacrylated trimethylammo-dimethylethyl, which is characterized by washing with water. Deodorizing method.
  • Item 2 The method according to Item 1, wherein the terpolymer is granular.
  • Item 3 The method according to Item 1 or 2, wherein washing is performed by stirring the terpolymer in water and separating a supernatant.
  • Item 4 A ternary copolymer comprising deodorized lower alkyl acrylate, lower alkyl methacrylate, and trimethylammonium-dimethyl ester methacrylate, which can be obtained by any method of Items 1 to 3. Coalescing.
  • Item 5 A terpolymer having substantially no unpleasant odor, comprising lower alkyl acrylate, lower alkyl methacrylate, and trimethylammonium-dimethylethyl methacrylate.
  • Item 6 A denture lining agent comprising the terpolymer of Item 4 or 5.
  • Ternary copolymers comprising lower alkyl acrylate, lower alkyl methacrylate and methacrylate trimethylammo-dimethylene which are the objects of deodorization of the present invention (hereinafter, simply referred to as ⁇ terpolymer '') (May be described) is a copolymer which also has three kinds of monomer powers of (1) lower alkyl acrylate, (2) lower alkyl methacrylate, and (3) trimethylammonium-dimethylethyl methacrylate.
  • lower alkyl acrylate examples include methyl acrylate, ethyl acrylate, n-propyl acrylate, isopropyl acrylate, n-butyl acrylate, isobutyl acrylate, sec-butyl acrylate, and t-butyl acrylate.
  • Preferred are methyl acrylate and ethyl acrylate, and more preferred is ethyl acrylate.
  • Lower alkyl methacrylate includes methyl methacrylate, ethyl methacrylate, N-propyl methacrylate, isopropyl methacrylate, n-butyl methacrylate, isobutyl methacrylate, sec-butyl methacrylate, t-butyl methacrylate, preferably methyl methacrylate, methacrylic Ethyl, more preferably methyl methacrylate, is an example.
  • the most preferred terpolymer of the present invention is a terpolymer of ethyl acrylate, methyl methacrylate, and methacrylic acid trimethylammo-dimethylethyl, and the terpolymer is Rohm Pharma Co., Ltd. It is commercially available from (Rohm Pharma GmbH) as Eudragit RS®.
  • the terpolymer of the present invention can be used in the form of powder, fine granules or granules, and fine granules or granules are preferred, and granules are particularly preferable. If the particle size of the terpolymer is too small, the copolymer is easily dispersed in water, and the copolymer is lost when the supernatant is removed. Further, when water after washing is removed by filtration, if the size of the terpolymer particles is too small, filtration becomes difficult due to clogging.
  • the average particle size of the granular terpolymer is from 0.1 to: LOmm, preferably from 0.3 to 5 mm, more preferably from 0.5 to 5 mm, particularly preferably from 1 to 5 mm.
  • LOmm preferably from 0.3 to 5 mm, more preferably from 0.5 to 5 mm, particularly preferably from 1 to 5 mm.
  • the particle diameter is in such a range, the operation of filtering or removing the supernatant can be easily performed, and the loss of the ternary copolymer can be minimized. If the particle size of the terpolymer is too small, dust may be scattered in the air, causing not only loss of the copolymer, but also pollution of the working environment and problems such as poor working environment.
  • the odor substances present in the particles can be efficiently eluted into the washing water, and the washed terpolymer can be retained in the oral cavity for a long time like a denture lining agent. Even for applications, odor substances can be removed to the extent that little or no odor is noticeable.
  • Washing water is generally used in an amount of about 2 to 10 parts by weight, preferably about 2 to 5 parts by weight, based on 1 part by weight of the terpolymer before deodorization.
  • the temperature at the time of water washing is about 5 to 60 ° C, preferably about 10 to 50 ° C, and the time of treatment in water depends on the amount of water used, the treatment temperature, the particle size of the terpolymer, etc. It is usually about 1 minute to 48 hours, preferably about 8 hours to 24 hours. Washing with water may be carried out by adding a terpolymer to water and leaving it to stand, but it is usually carried out by stirring, shaking or ultrasonic waves. Tap water can be used as the water, but distilled water, ion-exchanged water, purified water, or the like may be used. Stirring can be performed by, for example, a homomixer, a dispar mixer, or the like.
  • the terpolymer may be pulverized at the same time as the stirring to adjust the average particle size to the above-mentioned appropriate value. Therefore, if the average particle diameter after the deodorization treatment falls within the above range, the average particle diameter of the terpolymer before the deodorization treatment may be larger (for example, more than 10 mm).
  • Washing may be performed only once or may be repeated two or more times.
  • water containing an odorous substance derived from the terpolymer can be removed by decanting the supernatant by suction with a pump or the like, or may be removed by filtration.
  • a wire mesh can be used.
  • deodorized terpolymers are used as denture backing agents (denture stabilizing agents and mucosal conditioners that stabilize dentures on the oral mucosa) as an exfoliation enhancer that promotes exfoliation from the oral mucosa.
  • the terpolymer containing water is subjected to the next production step to produce a lining material for dentures that is substantially not odorous.
  • the loss of the terpolymer by washing is usually 0.2% by weight or less, preferably 0.1% by weight or less, and the variation in loss is small.
  • the loss of the terpolymer due to washing is about 0.5% by weight on average, and there is a maximum loss of 1% by weight.
  • the odor of the terpolymer can be evaluated, for example, by dissolving the copolymer in a solvent such as ethanol and removing the solvent, and then the odor of the residue is evaluated by a human sensory test by a panelist or the like.
  • the odor of the terpolymer can be efficiently removed by a simple operation of washing with water, and the loss of the terpolymer during washing with water can be reduced.
  • the terpolymer deodorized according to the present invention is blended with a backing agent for dentures, however, since the odor does not matter, the terpolymer deodorized according to the present invention is suitable as a peelability improving agent for a denture backing agent.
  • a terpolymer of ethyl acrylate “methyl methacrylate” trimethylammonium-dimethyl methacrylate (Eudragit RS 100 (registered trademark), manufactured by Rohm Pharma Co., Ltd .; average particle diameter 2 mm 11 parts by weight were dispersed in 40 parts by weight of purified water, stirred at 50 ° C. for 20 minutes, allowed to stand still, and the supernatant was carefully removed with an air pump equipped with a filter.
  • a powdery terpolymer (Eudragit RS PO (registered trademark), manufactured by Rohm Pharma Co., Ltd .; particle size 2.75 m to 704 m) is used. Except that, a deodorized copolymer was obtained in the same manner as above.
  • Example 1 the deodorized Eudragit RS obtained in Example 1 as a backing agent for dentures. It was confirmed that odor was hardly noticeable even when it was blended as a peelability improver and kept in the mouth for 24 hours.

Landscapes

  • Health & Medical Sciences (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Plastic & Reconstructive Surgery (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Dental Preparations (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Disinfection, Sterilisation Or Deodorisation Of Air (AREA)

Abstract

[PROBLEMES] Réduire la caractéristique d’odeur d’un terpolymère acrylate/méthacrylate pour ainsi permettre au terpolymère d’améliorer la sensation d’utilisation. [MOYENS POUR RESOUDRE LES PROBLEMES] Le procédé de désodorisation est caractérisé en ce qu’on lave un terpolymère comprenant des unités dérivées d’un acrylate d’alkyle inférieur, d’un méthacrylate d’alkyle inférieur et d’un chlorure de méthacrylate de triméthylammoniuméthyle, avec de l’eau pour désodoriser le terpolymère.
PCT/JP2005/006386 2004-03-31 2005-03-31 Terpolymere acrylate/methacrylate desodorise et procede de desodorisation correspondant WO2005095467A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2004107659A JP4756827B2 (ja) 2004-03-31 2004-03-31 脱臭されたアクリレート／メタクリレート系三元共重合体及びその脱臭方法
JP2004-107659 2004-03-31

Publications (1)

Publication Number Publication Date
WO2005095467A1 true WO2005095467A1 (fr) 2005-10-13

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PCT/JP2005/006386 WO2005095467A1 (fr) 2004-03-31 2005-03-31 Terpolymere acrylate/methacrylate desodorise et procede de desodorisation correspondant

Country Status (2)

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JP (1) JP4756827B2 (fr)
WO (1) WO2005095467A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008028003A2 (fr) 2006-09-01 2008-03-06 Smithkline Beecham Corporation Composition de soins de prothèses dentaires
CN110105487A (zh) * 2018-03-09 2019-08-09 广州茂丰药业有限公司 含季铵基（甲基）丙烯酸酯共聚物的溶液聚合制备方法

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB0525864D0 (en) * 2005-12-20 2006-02-01 Novartis Ag Organic compounds

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0648912A (ja) * 1992-07-31 1994-02-22 Mitsubishi Rayon Co Ltd 低臭・低刺激性歯科用材料
JPH06157641A (ja) * 1992-11-17 1994-06-07 Nippon Zeon Co Ltd アクリレート系重合体粒子の未反応単量体除去方法
JPH0742210B2 (ja) * 1988-11-04 1995-05-10 小林製薬株式会社 義歯用裏装剤
JPH11322836A (ja) * 1998-05-18 1999-11-26 Sekisui Plastics Co Ltd （メタ）アクリル酸エステル系樹脂粒子中の残存単量体の低減方法およびそれにより得られる（メタ）アクリル酸エステル系樹脂粒子

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5046446B2 (ja) * 2001-08-02 2012-10-10 電気化学工業株式会社 共重合樹脂及びその製造方法

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0742210B2 (ja) * 1988-11-04 1995-05-10 小林製薬株式会社 義歯用裏装剤
JPH0648912A (ja) * 1992-07-31 1994-02-22 Mitsubishi Rayon Co Ltd 低臭・低刺激性歯科用材料
JPH06157641A (ja) * 1992-11-17 1994-06-07 Nippon Zeon Co Ltd アクリレート系重合体粒子の未反応単量体除去方法
JPH11322836A (ja) * 1998-05-18 1999-11-26 Sekisui Plastics Co Ltd （メタ）アクリル酸エステル系樹脂粒子中の残存単量体の低減方法およびそれにより得られる（メタ）アクリル酸エステル系樹脂粒子

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008028003A2 (fr) 2006-09-01 2008-03-06 Smithkline Beecham Corporation Composition de soins de prothèses dentaires
EP2056787A2 (fr) * 2006-09-01 2009-05-13 SmithKline Beecham Corporation Composition de soins de prothèses dentaires
EP2056787A4 (fr) * 2006-09-01 2013-01-02 Glaxosmithkline Llc Composition de soins de prothèses dentaires
CN110105487A (zh) * 2018-03-09 2019-08-09 广州茂丰药业有限公司 含季铵基（甲基）丙烯酸酯共聚物的溶液聚合制备方法
CN110105487B (zh) * 2018-03-09 2021-07-30 广州茂丰药业有限公司 含季铵基(甲基)丙烯酸酯共聚物的溶液聚合制备方法

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Publication number Publication date
JP4756827B2 (ja) 2011-08-24
JP2005290213A (ja) 2005-10-20

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