WO1982001708A1 - (meth)acryloyl fluoride-containing polymer and dental material containing the same - Google Patents

(meth)acryloyl fluoride-containing polymer and dental material containing the same Download PDF

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Publication number
WO1982001708A1
WO1982001708A1 PCT/JP1981/000337 JP8100337W WO8201708A1 WO 1982001708 A1 WO1982001708 A1 WO 1982001708A1 JP 8100337 W JP8100337 W JP 8100337W WO 8201708 A1 WO8201708 A1 WO 8201708A1
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WO
WIPO (PCT)
Prior art keywords
meta
polymer
acrylic acid
dental
dental material
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.)
Ceased
Application number
PCT/JP1981/000337
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English (en)
French (fr)
Japanese (ja)
Inventor
Eiichi Masuhara
Yoshio Imai
Yoshinori Kadoma
Mitsuru Ueda
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Individual
Original Assignee
Individual
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 Individual filed Critical Individual
Priority to DE19813152516 priority Critical patent/DE3152516A1/de
Publication of WO1982001708A1 publication Critical patent/WO1982001708A1/ja
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F20/00Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
    • C08F20/02Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K6/00Preparations for dentistry
    • A61K6/80Preparations for artificial teeth, for filling teeth or for capping teeth
    • A61K6/884Preparations for artificial teeth, for filling teeth or for capping teeth comprising natural or synthetic resins
    • A61K6/887Compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds

Definitions

  • the present invention relates to a (meth) acrylic acid fluoride component-containing polymer and its use, and more particularly, to a (meth) acrylic acid fluorinated phenololeide.
  • (meth) acrylic acid referred to herein is either itself or part of a large group, even if it is part of a larger group. Includes acrylic acid and methacrylic acid.
  • alkyl as used in the specification may or may not be a radical of any kind, even if it is one of the larger radicals.
  • the polymer according to the present invention is a material having a high molecular weight / synthetic resin material, and has a material that gradually releases fluorine ion in water.
  • _O PI _ — — Can be used for a variety of applications, but most
  • non-fluorinated compounds such as sodium fluoride are combined.
  • This fluorine compound has the drawback that it elutes in a short period of time, and thereafter the mechanical properties of the resin itself are significantly reduced.
  • Another object of the present invention is to provide a material that releases fluorine ion gradually over a long period of time and that is used in the oral cavity; .
  • is also to provide a material containing the above-mentioned oblique.
  • R represents H or CH 3 .
  • R represents H or CH 3 ]
  • R represents H or CH 3 , and R represents a C 8 -low alkyl group].
  • Radical polymerization can be carried out in the presence of a solvent. In the absence or presence of an appropriate initiator, for example, peroxidized laurol, dementia benzoinole, etc. By adding a substance that easily produces free radicals such as lonitrile and adding polymerization conditions], the polymerization that can be easily performed is usually carried out under normal pressure. 40 to 80 "C” !! can be reacted for 48 hours, preferably 2 to 5 hours. b Control of the reaction and the acquisition of the product, which is a thermoplastic resin, were established in the production of (meta) acrylic polymer. Just follow the technician.
  • Monomers for producing the above-mentioned homopolymers and copolymers include (meta) acrylic drums of the following formula.
  • R represents H or CH 3 .
  • the C the A Le key Le group [ ⁇ C 8 tables Wa 3 a are included.
  • the ⁇ Honoré key Honoré group ⁇ c 8, main Ji Le, E Chinore, Buchinore, I This includes, but is not limited to, sobutinole, pentinole, n-hexinole, n-heminole, and n-octinole.
  • the material of the invention emits fluorine in water
  • OVPI-' ⁇ WiFO — Shows that the properties of the polymer represented by the above formula are — C (O) — The F portion is slowly hydrolyzed to — C (0) -OH. It is understood that HF is liberated
  • the total amount of the released fluorine ion is, as the proportion of the monomer containing CC 0) -F in the formula of ⁇ is larger, the larger the proportion of the unit is, that is, -C
  • the emission muck is higher when the m / n ratio is larger.
  • the release rate may change temporally, and when the ratio of mn is maximum (100,000), the time is When the ratio of m ⁇ n is small (10 no 90), there is an annoyance. In the meantime, there should be a mono-to-quantity ratio with a nearly constant release rate.
  • Units are at least 10 mol%, preferably between 20 and
  • O PI a One. This is due to the fact that at less than 10%, the release of fluorine ions is slow and the total release is small.
  • the molecular weight of the polymer is preferably from 1,500 to 250,000, and more preferably from 50,000 to 150,000.
  • No. Copolymers are usually random copolymers in random form
  • the rate of release of fluorine ions depends on the rate of formation of the material of the present invention (monomer ratio conditions, molecular weight, etc.).
  • the state of use that is, whether the film is to be used or powdered, how thick the film is, what is the particle size of the powder), and more. It largely differs depending on the mode of combination with the components of the pond to be combined (the kind and composition ratio of other components). Of course, it depends on how sensitive it is to water. Therefore, in each case, we need to find the optimal writhing. That 's a little'
  • the fluorine ion sustained-release material of the present invention is said to have been the end of the development], and it is suitable as a material that can be strengthened by fluoridation of the tooth.
  • it has great application to various types of therapeutic agents and treatments in the dental field as described below.
  • It may be irradiated with ultraviolet light or visible light, and polymerized.
  • FIGS. 1, 2, 3 and 4 all show the results obtained by performing a fluorine dissolution test on an example of the fluorine ion sustained stopper material of the present invention. It is a graph. In the figure, the horizontal axis represents time, and the curve represents the amount of eluted fluorine (dots) and integral eluted fluorine per unit.
  • Elemental analysis Direct (Actual measurement%) C: 59.19, ⁇ : 7.30,
  • Example 41-methacrylic acid is obtained in the same manner as in Example 2. ⁇ Dissolve Fluoride 2.87 7 and Methacryl® 2.16 ⁇ ? In Benzene 5 and add azovisi sobutylonitrinole After adding 25 ⁇ and sealing, polymerization was carried out in a constant temperature water bath at 60 C for 150 minutes. After pouring the contents into an ether, a 0.84 ⁇ polymer was obtained. The total yield was 17.8% polymer. Light content 49.4% Elemental analysis Revision C: 57.03. ⁇ : 6.70, F: 9.9
  • a methacrylic acid full-length guide 2.5 ⁇ and a methacrylonitrile methinolate 2.5 ⁇ are placed in a polymerization glass sealed tube having an inner volume of 1 and azovis. After dissolving with isobutyronitrile phosphorus 4 and substituting with nitrogen gas, the mixture was polymerized in a constant temperature water at 60 C for 4 ⁇ hours and further at 65 C for 6 hours.
  • Example 6 using a mixture of methacryloyl phthalate 1.5 and methyl methacrylate 3,9- as monomer to be polymerized The same polymerization operation was performed. From the round bar of the piece, a rounded sample of 87 ⁇ and 17.7 in thickness was cut out and subjected to a dissolution test. Yugo is the first
  • the fluorine ion sustained-release polymer obtained in Example 3 was mechanically pulverized to obtain a powder having a particle size of 2 ⁇ 0 to 350.
  • the following composition was added to the base to produce a dental sealant.
  • a paste obtained by mixing the above mixed powder 70 ⁇ and a comonomer solution 50 ' was used as a dental filler. After 8 minutes of curing, white cured 3 ⁇ 4 was obtained.
  • a dental cement having a composition including the polymer of Example 3 was prototyped.
  • Hardener hn Full boran ⁇ Dani3 ⁇ 4J9 In addition to the hardener solution, it was mixed with powder to form a solid, wrapped in cellophane, and cured at room temperature, with a curing time of 12 minutes. Colorless and transparent cured
  • a 7 -lm film was prepared from the obtained polymer in the same manner as in Example 5, and a test piece of 30 x 14 N was immersed in 10 si of evaporating water. When the mixture was left standing, elution of fluorine ion at 0 to 18% / day was observed.

Landscapes

  • Health & Medical Sciences (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Chemical & Material Sciences (AREA)
  • Epidemiology (AREA)
  • Animal Behavior & Ethology (AREA)
  • Organic Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • Plastic & Reconstructive Surgery (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Polymers & Plastics (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Cosmetics (AREA)
  • Dental Preparations (AREA)
  • Medicinal Preparation (AREA)
PCT/JP1981/000337 1980-11-19 1981-11-18 (meth)acryloyl fluoride-containing polymer and dental material containing the same Ceased WO1982001708A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DE19813152516 DE3152516A1 (de) 1980-11-19 1981-11-18 (meth)acryloyl fluoride-containing polymer and dental material containing the same

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP55162782A JPS5788106A (en) 1980-11-19 1980-11-19 Fluorine ion prolongably releasing material and dental material using it
JP80/162782801119 1980-11-19

Publications (1)

Publication Number Publication Date
WO1982001708A1 true WO1982001708A1 (en) 1982-05-27

Family

ID=15761101

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP1981/000337 Ceased WO1982001708A1 (en) 1980-11-19 1981-11-18 (meth)acryloyl fluoride-containing polymer and dental material containing the same

Country Status (2)

Country Link
JP (1) JPS5788106A (enExample)
WO (1) WO1982001708A1 (enExample)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114404658A (zh) * 2022-02-18 2022-04-29 中国科学技术大学先进技术研究院 骨水泥及其制备方法、骨科植入材料

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6212706A (ja) * 1985-03-18 1987-01-21 Kuraray Co Ltd フツ素イオン徐放性歯科用組成物
US5296513A (en) * 1988-12-21 1994-03-22 Mitsubishi Rayon Co., Ltd. Dental composition and process for producing dental polymeric shaped articles
JPH0497812U (enExample) * 1991-01-09 1992-08-25
CN105101934B (zh) 2013-03-26 2017-09-22 可乐丽则武齿科株式会社 牙科用固化性组合物

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
Macromolecular Chemistry and Physics, Vol. 182, No. 1, Page 273-7, 16. January 1981, Masuhara Elichi: "Controlled release of fluoride ions from methacryloyl fluoride-methyl methacrylate copolymers" *
Zstka (0044-4634) Zh. Strukt. Khim., Vol. 20, No. 6, Page 1030-7, 79 Glebova L.A.: "rotational isomerism and restrained internal rotation in a methacryloyl fluoride molecule" *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114404658A (zh) * 2022-02-18 2022-04-29 中国科学技术大学先进技术研究院 骨水泥及其制备方法、骨科植入材料

Also Published As

Publication number Publication date
JPH021164B2 (enExample) 1990-01-10
JPS5788106A (en) 1982-06-01

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