JPH0470321B2 - - Google Patents
Info
- Publication number
- JPH0470321B2 JPH0470321B2 JP29717786A JP29717786A JPH0470321B2 JP H0470321 B2 JPH0470321 B2 JP H0470321B2 JP 29717786 A JP29717786 A JP 29717786A JP 29717786 A JP29717786 A JP 29717786A JP H0470321 B2 JPH0470321 B2 JP H0470321B2
- Authority
- JP
- Japan
- Prior art keywords
- resin
- diallyl phthalate
- meth
- unsaturated polyester
- laminates
- 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
Links
- 229920005989 resin Polymers 0.000 claims description 27
- 239000011347 resin Substances 0.000 claims description 27
- 239000004641 Diallyl-phthalate Substances 0.000 claims description 16
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 claims description 16
- 229920006337 unsaturated polyester resin Polymers 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 10
- 229920000193 polymethacrylate Polymers 0.000 claims description 10
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 7
- 239000011342 resin composition Substances 0.000 claims description 6
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 3
- -1 methacryloyl groups Chemical group 0.000 claims description 3
- 229920000058 polyacrylate Polymers 0.000 claims description 3
- 239000000600 sorbitol Substances 0.000 claims description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- 235000019504 cigarettes Nutrition 0.000 description 5
- 239000000123 paper Substances 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000002655 kraft paper Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 229920001187 thermosetting polymer Polymers 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 239000004640 Melamine resin Substances 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 125000004386 diacrylate group Chemical group 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000011120 plywood Substances 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000003856 thermoforming Methods 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
- C23C22/00—Chemical surface treatment of metallic material by reaction of the surface with a reactive liquid, leaving reaction products of surface material in the coating, e.g. conversion coatings, passivation of metals
- C23C22/05—Chemical surface treatment of metallic material by reaction of the surface with a reactive liquid, leaving reaction products of surface material in the coating, e.g. conversion coatings, passivation of metals using aqueous solutions
- C23C22/06—Chemical surface treatment of metallic material by reaction of the surface with a reactive liquid, leaving reaction products of surface material in the coating, e.g. conversion coatings, passivation of metals using aqueous solutions using aqueous acidic solutions with pH less than 6
- C23C22/07—Chemical surface treatment of metallic material by reaction of the surface with a reactive liquid, leaving reaction products of surface material in the coating, e.g. conversion coatings, passivation of metals using aqueous solutions using aqueous acidic solutions with pH less than 6 containing phosphates
- C23C22/08—Orthophosphates
- C23C22/18—Orthophosphates containing manganese cations
- C23C22/182—Orthophosphates containing manganese cations containing also zinc cations
- C23C22/184—Orthophosphates containing manganese cations containing also zinc cations containing also nickel cations
Description
（発明の技術分野）
本発明は、硬化物特性が改善されあ熱硬化性樹
脂積層板用樹脂組成物に関する。
（従来技術）
熱硬化性樹脂積層板、特にジアリルフタレート
樹脂積層板は、優れた成形性、ポストフオーム加
工性を有しており、また物理的、化学的特性にも
優れた積層板として知られ、中でも化粧板は落着
いた風合いをもつ材料として好評を博している。
しかし、ジアリルフタレート樹脂積層板は、硬度
及び耐シガレツト性等の耐熱性の点でメラミン樹
脂積層板より劣つており、特にデスク、カウンタ
ー等に代表される天板への使用に際して難点があ
つた。また不飽和ポリエステル樹脂積層板におい
ても同様な問題があつた。
（発明の目的）
本発明は、上記の如き欠点がなく表面特性の改
善されたジアリルフタレート樹脂もしくは不飽和
ポリエステル樹脂積層板用として好適な樹脂組成
物を提供することを目的とする。
（発明の構成）
本発明は、ジアリルフタレート樹脂又は不飽和
ポリエステル樹脂あるいはこれらの混合樹脂に、
分子内にアクリロイル基又はメタアクリロイル基
を３個以上有するソルビツトのポリアクリレート
又はポリメタアクリレートあるいはこれらの混合
物を混合したことを特徴とする硬化物特性が改善
された積層板用樹脂組成物である。
本発明におけるジアリルフタレート樹脂とは、
既に知られているオルソ、イソ又はテレージアリ
ルフタレートプレポリマーの単独またはこれらの
混合物もしくはこれらの変性プレポリマー等のジ
アリルフタレート系プレポリマーをいう。また不
飽和ポリエステル樹脂は通常知られている常温で
液体状のものもしくは固体状のものが用いられ
る。不飽和ポリエステル樹脂単独使用の場合には
固体状のものが作業性の点で好ましい。混合樹脂
として用いる場合、両者の混合比は任意でよい
が、ジアリルフタレート樹脂の特徴を生かした積
層板とする場合にはジアリルフタレート樹脂が樹
脂中少なくとも20重量％必要である。
本発明に用いられるソルビツトのポリアクリレ
ート又はポリメタアクリレート（以下両者を総称
してポリ（メタ）アクリレートという）として
は、分子内にアクリロイル基又はメタアクリロイ
ル基（以下両者を総称して（メタ）アクリロイル
基という）を３個以上最高６個有するポリ（メ
タ）アクリレートの単独もしくは混合物が用いら
れる。（メタ）アクリロイル基が２個以下のジ又
はモノ（メタ）アクリレートではジアリルフタレ
ート樹脂もしくは不飽和ポリエステル樹脂との相
溶性が充分でなく、目的とする効果が得られな
い。
本発明において、ソルビツトのポリ（メタ）ア
クリレートの配合量はジアリルフタレート樹脂又
は不飽和ポリエステル樹脂あるいはこれらの混合
樹脂100重量部に対して５〜70重量部、好ましく
は10〜50重量部の範囲が適当である。５重量部未
満では本発明の目的とする表面特性の改善効果が
充分に得られず、また70重量部を超えると硬化物
が固くなりすぎて脆くなつたり、加工時樹脂がベ
トついて作業性に問題を生ずることになる。
本発明の組成物には、通常知られるジアリルフ
タレート樹脂又は不飽和ポリエステル樹脂の硬化
剤が添加される。また必要に応じて他種の反応性
モノマーや該技術分野に通常用いられる添加剤、
例えば内部離型剤、充填剤、難燃剤、重合禁止
剤、顔料等を添加することができる。
本発明組成物を用いて積層板を製造するには、
適当な溶剤、例えばアセトン、トルエン、メチル
エチルケトン等の有機溶剤に組成物を溶解させて
樹脂液を調製し、これを基材に用途に応じて適量
含浸せしめて乾燥後、合板やパーチクルボード、
あるいは通常の樹脂を含浸せしめたクラフト紙を
コアとして積層加熱成形することによつて達成さ
れる。また本発明組成物を含浸せしめた基材を加
熱硬化させた後、アルミニウム板等の金属板に接
着剤を用いて積層することもできる。
上記含浸用基材としては、印刷紙、織布、不織
布、木質単板等がある。加熱成形条件は、従来知
られるジアリルフタレート樹脂又は不飽和ポリエ
ステル樹脂の成形条件でよく、通常100〜160℃、
１〜60Kg／cm2、１〜60分間で充分である。
（発明の効果）
本発明のソルビツトのポリ（メタ）アクリレー
トを含む組成物を用いた積層板は、該ポリ（メ
タ）アクリレートがモノもしくはジ（メタ）アク
リレートである場合あるいは該ポリ（メタ）アク
リレートを含まない従来のジアリルフタレート樹
脂もしくは不飽和ポリエステル樹脂を用いた積層
板と較べて引き掻き硬度及び耐シガレツト性等の
表面特性が飛躍的に向上しており、従来使用困難
とされていた天板用にも使用可能となつたもので
ある。
（実施例）
実施例１〜３ 比較例１〜３
表１に示される樹脂組成物をベタ印刷された坪
量100ｇ／m2の印刷紙に含浸させ、乾燥後樹脂付
着量130ｇ／m2の含浸紙を得た。
別に通常のジアリルフタレート樹脂を含浸させ
たクラフト紙（総坪量240ｇ／m2、内樹脂付着量
100ｇ／m2）２枚を用意し、その２枚重ねの上に
上記含浸紙を重ね、ツヤ有り鏡面板を用いて130
℃、30Kg／cm2でプレスし、挿入20分後に水冷して
積層板を得た。
上記積層板の表面引き掻き硬度及び耐シガレツ
ト性を測定しその結果を表１に示した。
表面引き掻き硬度：JAS規格Ａ試験による10点平
均値、深さ（μ）。
耐シガレツト性：火付きタバコを２分間放置後メ
タノールで清拭した後の表面状態の観察。
評価 （２点による平均）
○ 変色殆んどなし
× 焼けによる着色あり
なお、比較例２は本発明に用いられるポリ（メ
タ）アクリレートとは異なるアクリロイル基が１
個のモノアクリレートの例であり、このものは樹
脂組成物が混ざり合わず成形ができなかつた。ま
た比較例３はアクリロイル基が２個のジアクリレ
ートを使用した例である。
(Technical Field of the Invention) The present invention relates to a resin composition for a thermosetting resin laminate, which has improved cured product properties. (Prior art) Thermosetting resin laminates, especially diallyl phthalate resin laminates, have excellent moldability and post-form processability, and are also known as laminates with excellent physical and chemical properties. Among them, decorative boards are popular as materials with a calm texture.
However, diallylphthalate resin laminates are inferior to melamine resin laminates in terms of hardness and heat resistance such as cigarette resistance, and are particularly difficult to use for top plates such as desks and counters. Similar problems also occurred in unsaturated polyester resin laminates. (Objective of the Invention) An object of the present invention is to provide a resin composition suitable for use in diallyl phthalate resin or unsaturated polyester resin laminates, which does not have the above-mentioned drawbacks and has improved surface properties. (Structure of the Invention) The present invention provides a diallylphthalate resin, an unsaturated polyester resin, or a mixed resin thereof,
A resin composition for laminates with improved properties of a cured product, characterized in that it contains a sorbitol polyacrylate or polymethacrylate having three or more acryloyl or methacryloyl groups in the molecule, or a mixture thereof. The diallyl phthalate resin in the present invention is
It refers to a diallyl phthalate prepolymer such as already known ortho, iso, or theresa diallyl phthalate prepolymers alone, a mixture thereof, or a modified prepolymer thereof. Further, as the unsaturated polyester resin, those which are generally known to be liquid or solid at room temperature are used. When an unsaturated polyester resin is used alone, a solid one is preferred from the viewpoint of workability. When used as a mixed resin, the mixing ratio of the two may be arbitrary, but when producing a laminate that takes advantage of the characteristics of the diallyl phthalate resin, the diallyl phthalate resin needs to be at least 20% by weight in the resin. The sorbit polyacrylate or polymethacrylate (hereinafter both collectively referred to as poly(meth)acrylate) used in the present invention has an acryloyl group or methacryloyl group (hereinafter both collectively referred to as (meth)acryloyl group) in the molecule. Poly(meth)acrylates having 3 or more and up to 6 groups (referred to as groups) may be used alone or in mixtures. Di- or mono(meth)acrylates having two or less (meth)acryloyl groups do not have sufficient compatibility with diallyl phthalate resins or unsaturated polyester resins, and the desired effect cannot be obtained. In the present invention, the blending amount of poly(meth)acrylate in sorbit ranges from 5 to 70 parts by weight, preferably from 10 to 50 parts by weight, based on 100 parts by weight of diallylphthalate resin, unsaturated polyester resin, or mixed resin thereof. Appropriate. If it is less than 5 parts by weight, the desired effect of improving the surface properties of the present invention cannot be obtained, and if it exceeds 70 parts by weight, the cured product may become too hard and brittle, or the resin may become sticky during processing, resulting in poor workability. This will cause problems. A commonly known curing agent for diallyl phthalate resin or unsaturated polyester resin is added to the composition of the present invention. In addition, if necessary, other reactive monomers and additives commonly used in the technical field,
For example, internal mold release agents, fillers, flame retardants, polymerization inhibitors, pigments, etc. can be added. To produce a laminate using the composition of the present invention,
A resin solution is prepared by dissolving the composition in an appropriate solvent, such as an organic solvent such as acetone, toluene, or methyl ethyl ketone.The resin solution is impregnated into a base material in an appropriate amount depending on the purpose, and after drying, it can be used for plywood, particle board, etc.
Alternatively, it can be achieved by laminating and thermoforming a core made of kraft paper impregnated with a common resin. Furthermore, after the base material impregnated with the composition of the present invention is heated and cured, it can be laminated onto a metal plate such as an aluminum plate using an adhesive. Examples of the substrate for impregnation include printed paper, woven fabric, nonwoven fabric, and wood veneer. The hot molding conditions may be the conventional molding conditions for diallyl phthalate resin or unsaturated polyester resin, usually 100 to 160°C,
1 to 60 kg/cm 2 for 1 to 60 minutes is sufficient. (Effects of the Invention) A laminate using a composition containing poly(meth)acrylate of sorbitol of the present invention can be used when the poly(meth)acrylate is mono- or di(meth)acrylate, or when the poly(meth)acrylate is mono- or di(meth)acrylate. Surface properties such as scratch hardness and cigarette resistance are dramatically improved compared to conventional laminates using diallyl phthalate resin or unsaturated polyester resin, which do not contain carbon dioxide, making it a top plate that was previously considered difficult to use. It is now possible to use it for various purposes. (Examples) Examples 1 to 3 Comparative Examples 1 to 3 The resin compositions shown in Table 1 were impregnated onto printed paper with a basis weight of 100 g/m 2 , and after drying, the resin coating amount was 130 g/m 2 . Impregnated paper was obtained. Separately, kraft paper impregnated with ordinary diallyl phthalate resin (total basis weight 240g/m 2 , inner resin adhesion amount)
Prepare two sheets (100g/m 2 ), layer the above impregnated paper on top of the two sheets, and use a glossy mirror plate to
It was pressed at 30Kg/cm 2 at 30°C and cooled with water 20 minutes after insertion to obtain a laminate. The surface scratch hardness and cigarette resistance of the above laminate were measured and the results are shown in Table 1. Surface scratch hardness: 10-point average value, depth (μ) according to JAS Standard A test. Cigarette resistance: Observation of the surface condition after a lit cigarette was left for 2 minutes and then wiped with methanol. Evaluation (average of 2 points) ○ Almost no discoloration × Coloring due to burning Comparative Example 2 has one acryloyl group different from the poly(meth)acrylate used in the present invention.
This is an example of a monoacrylate, in which the resin composition did not mix and could not be molded. Comparative Example 3 is an example in which a diacrylate having two acryloyl groups was used.
【表】
表(1)において註(1)〜(4)は以下のとおりである。
(1) メチルエチルケトン50重量％溶液粘度（30
℃）96.5cp、ヨウ素価56.7のプレポリマー
(2) マレイン酸１モル、フタル酸１モルとプロピ
レングリコール２モルよりなる酸価34.5の市販
ポリエステル樹脂
(3) 「DR−20S」大阪曹達社商品名
(4) 「カープレツクス」塩野義製薬社商品名[Table] Notes (1) to (4) in Table (1) are as follows. (1) Methyl ethyl ketone 50% by weight solution viscosity (30
℃) 96.5 cp, prepolymer with an iodine value of 56.7 (2) A commercially available polyester resin with an acid value of 34.5 consisting of 1 mole of maleic acid, 1 mole of phthalic acid and 2 moles of propylene glycol (3) "DR-20S" Osaka Soda Co., Ltd. trade name (4) “Carplex” Shionogi & Co., Ltd. product name
Claims (1)
テル樹脂あるいはこれらの混合樹脂に、分子内に
アクリロイル基又はメタアクリロイル基を３個以
上有するソルビツトのポリアクリレート又はポリ
メタアクリレートあるいはこれらの混合物を混合
したことを特徴とする硬化物特性が改善された積
層板用樹脂組成物。1. A polyacrylate or polymethacrylate of sorbitol having three or more acryloyl groups or methacryloyl groups in the molecule, or a mixture thereof, is mixed with a diallyl phthalate resin, an unsaturated polyester resin, or a mixed resin thereof. A resin composition for laminates with improved cured product properties.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP29717786A JPS63150312A (en) | 1986-12-12 | 1986-12-12 | Resin composition for laminate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP29717786A JPS63150312A (en) | 1986-12-12 | 1986-12-12 | Resin composition for laminate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63150312A JPS63150312A (en) | 1988-06-23 |
| JPH0470321B2 true JPH0470321B2 (en) | 1992-11-10 |
Family
ID=17843174
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP29717786A Granted JPS63150312A (en) | 1986-12-12 | 1986-12-12 | Resin composition for laminate |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63150312A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5335247B2 (en) * | 2007-01-17 | 2013-11-06 | クラレノリタケデンタル株式会社 | Hydrophilic polymerizable monomer-containing composition and dental primer |
| CN101663336B (en) * | 2007-03-20 | 2012-10-10 | 可乐丽则武齿科株式会社 | Polymerizable monomer, polymerizable composition and dental material |
-
1986
- 1986-12-12 JP JP29717786A patent/JPS63150312A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS63150312A (en) | 1988-06-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |