JP5827862B2 - Method for producing flame retardant plate comprising methacrylic resin composition - Google Patents
Method for producing flame retardant plate comprising methacrylic resin composition Download PDFInfo
- Publication number
- JP5827862B2 JP5827862B2 JP2011223794A JP2011223794A JP5827862B2 JP 5827862 B2 JP5827862 B2 JP 5827862B2 JP 2011223794 A JP2011223794 A JP 2011223794A JP 2011223794 A JP2011223794 A JP 2011223794A JP 5827862 B2 JP5827862 B2 JP 5827862B2
- Authority
- JP
- Japan
- Prior art keywords
- mol
- resin composition
- flame
- methacrylic resin
- phosphonic acid
- 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.)
- Active
Links
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Description
本発明は、照明材料、光学材料、看板、ディスプレイ、建築材料、装飾材料等に好適に用いられるメタクリル樹脂組成物からなる難燃板の製造方法に関する。
The present invention relates to a method for producing a flame retardant plate comprising a methacrylic resin composition suitably used for lighting materials, optical materials, signboards, displays, building materials, decorative materials, and the like.
難燃性を有するメタクリル樹脂組成物として、特許文献１〜３には、非ハロゲン系リン酸エステルを含有するメタクリル樹脂組成物が記載されている。
すなわち、非ハロゲン系リン酸エステルとして、具体的には、以下のものが使用されている。
特許文献１：２−メタクリロイロキシ−１−メチルエチル ホスフェート、２−メタクリロイロキシエチルホスフェート、ビス（２−メタクリロイロキシエチル） ホスフェート、２−アクリロイロキシエチルホスフェート、ビス（２−アクリロイロキシエチル） ホスフェート
特許文献２：トリメチルホスフェート、トリエチルホスフェート
特許文献３：２−メタクリロイロキシエチル アシッドホスフェート
As methacrylic resin compositions having flame retardancy, Patent Documents 1 to 3 describe methacrylic resin compositions containing non-halogen phosphates.
Specifically, the following are used as non-halogen phosphates.
Patent Document 1: 2-methacryloyloxy-1-methylethyl phosphate, 2-methacryloyloxyethyl phosphate, bis (2-methacryloyloxyethyl) phosphate, 2-acryloyloxyethyl phosphate, bis (2-acryloyloxy) Ethyl) Phosphate Patent Document 2: Trimethyl phosphate, Triethyl phosphate Patent Document 3: 2-Methacryloyloxyethyl acid phosphate
しかしながら、上記従来のメタクリル樹脂組成物は、難燃性および耐熱性の両立という点で、必ずしも満足のいくものではなかった。
そこで、本発明の課題は、難燃性を有し、かつ耐熱性に優れるメタクリル樹脂組成物からなる難燃板の製造方法を提供することである。
However, the conventional methacrylic resin composition is not always satisfactory in terms of both flame retardancy and heat resistance.
Then, the subject of this invention is providing the manufacturing method of the flame retardant board which consists of a methacryl resin composition which has a flame retardance and is excellent in heat resistance.
本発明者らは、上記課題を解決すべく鋭意研究を重ねた結果、本発明を完成するに至った。すなわち、本発明は、難燃板を製造する方法であって、メタクリル酸メチルと、下記式（１）で示されるホスホン酸エステルとからなり、
メタクリル酸メチル及び上記ホスホン酸エステルの総量を１００モル％として、メタクリル酸メチルが８０〜９９モル％であり、上記ホスホン酸エステルが１〜２０モル％である単量体混合物、及びラジカル重合開始剤を含む重合性混合物をキャスト重合させる構成からなる。
この方法において、単量体混合物に含まれるメタクリル酸メチルは８５〜９５モル％、そして上記ホスホン酸エステルは５〜１５モル％とすることができる。また、式（１）におけるＲ2 はメチル基であるのが好ましく、Ｒ1 はメチレン基であるのが好ましい。
As a result of intensive studies to solve the above problems, the present inventors have completed the present invention. That is, the present invention provides a method of producing a flame燃板, Ri Do from the methyl methacrylate, the phosphonic acid ester represented by the following formula (1),
Monomer mixture in which the total amount of methyl methacrylate and the phosphonic acid ester is 100 mol%, the methyl methacrylate is 80 to 99 mol%, and the phosphonic acid ester is 1 to 20 mol%, and a radical polymerization initiator It consists of the structure which cast-polymerizes the polymeric mixture containing this .
In this method, Rume methacrylic acid methyl contained in the monomer mixture is 85 to 95 mol%, and the phosphonate ester may be a 5 to 15 mol%. Further, it is preferable R 2 which in formula (1) is a methyl group, R 1 is preferably a methylene group.
本発明によれば、メタクリル酸メチルと、特定のホスホン酸エステルとからなる単量体混合物を共重合させるので、難燃性を有し、かつ耐熱性に優れるメタクリル樹脂組成物からなる難燃板を製造することができ、この難燃板は、照明材料、光学材料、看板、ディスプレイ、建築材料、装飾材料等に好適に用いられる。
According to the present invention, a methyl methacrylate, Runode was a monomer mixture consisting of a specific phosphonate copolycondensates engaged, flame consisting methacrylic resin composition excellent in flame retardancy have, and heat resistance A fuel plate can be manufactured , and this flame retardant plate is suitably used for lighting materials, optical materials, signboards, displays, building materials, decorative materials, and the like.
本発明では、メタクリル酸メチルと、特定のホスホン酸エステルとからなる単量体混合物をキャスト重合して、難燃板を製造する。
In the present invention, a methyl methacrylate, a monomer mixture consisting of a specific phosphonate cast polymerization, produce flame燃板.
本発明におけるホスホン酸エステルは、下記式（１）で示される。
式中、Ｒ1は炭素数１〜５のアルキレン基を表し、Ｒ2は炭素数１〜６のアルキル基を表す。なかでも、上記式（１）中、Ｒ1としてはメチレン基が好ましく、Ｒ2としてはメチル基、エチル基が好ましく、メチル基がより好ましい。また、前記ホスホン酸エステルは、必要に応じてそれらの１種または２種以上用いてもよい。
The phosphonic acid ester in the present invention is represented by the following formula (1).
In the formula, R 1 represents an alkylene group having 1 to 5 carbon atoms, and R 2 represents an alkyl group having 1 to 6 carbon atoms. Among them, in the above formula (1), R 1 is preferably a methylene group, R 2 is preferably a methyl group or an ethyl group, and more preferably a methyl group. Moreover, you may use the said phosphonic acid ester 1 type, or 2 or more types as needed.
上記式（１）で示されるホスホン酸エステルの市販品としては、例えば、SPECIFIC POLYMERS社製の「MAPC1 ME」、「MAPC1 ET」などが挙げられる。 Examples of commercially available phosphonic acid esters represented by the above formula (1) include “MAPC1 ME” and “MAPC1 ET” manufactured by SPECIFIC POLYMERS.
単量体混合物に含まれるメタクリル酸メチル及びホスホン酸エステルの各含有量は、メタクリル酸メチル及びホスホン酸エステルの総量を１００モル％として、メタクリル酸メチルが８０〜９９モル％であり、ホスホン酸エステルが１〜２０モル％である。好ましくはメタクリル酸メチルが８５〜９５モル％であり、ホスホン酸エステルが５〜１５モル％である。メタクリル酸メチル及びホスホン酸エステルの各含有量が上記範囲であれば、得られる難燃板に優れた難燃性および耐熱性を付与することができる。
Each content of the monomer mixture of methyl methacrylate and phosphonic acid esters contained in the total amount of methyl methacrylate and phosphonic acid esters as 100 mol%, methyl main methacrylic acid is 80 to 99 mol%, phosphonic acid ester Ru 1 to 20 mol% der. Good Mashiku is methyl methacrylate 85 to 95 mol%, phosphonic acid ester is 5 to 15 mol%. If each content of methyl methacrylate and phosphonic acid ester is the said range, the flame retardance and heat resistance which were excellent in the obtained flame-resistant board can be provided.
尚、メタクリル樹脂組成物には、必要に応じて、離型剤、重合調節剤、紫外線吸収剤、光拡散剤、着色剤、補強剤、充填剤、安定剤、酸化防止剤、帯電防止剤等の各種添加剤を、１種または２種以上含有させてもよい。例えば、光拡散剤を含有するメタクリル樹脂組成物は、看板やディスプレイの前面板に利用できる拡散板や乳半板として好適である。光拡散剤の種類は限定されることなく、有機系もしくは無機系の微粒子が用いられ、有機系微粒子としては、例えば、ポリスチレン架橋粒子、ポリメタクリルスチレン（ＭＳ）架橋粒子、アクリル系架橋粒子などが挙げられ、無機系微粒子としては、例えば、酸化チタン、硫酸バリウム、酸化ケイ素などが挙げられる。 The methacrylic resin composition includes a release agent, a polymerization regulator, an ultraviolet absorber, a light diffusing agent, a colorant, a reinforcing agent, a filler, a stabilizer, an antioxidant, an antistatic agent, and the like as necessary. These various additives may be contained alone or in combination of two or more. For example, a methacrylic resin composition containing a light diffusing agent is suitable as a diffusion plate or milk half plate that can be used for a front plate of a signboard or a display. The type of the light diffusing agent is not limited, and organic or inorganic fine particles are used. Examples of the organic fine particles include polystyrene crosslinked particles, polymethacrylstyrene (MS) crosslinked particles, and acrylic crosslinked particles. Examples of the inorganic fine particles include titanium oxide, barium sulfate, and silicon oxide.
（製造方法）
次に、本発明の難燃板の製造方法について説明する。
本発明の製造方法は、上記単量体混合物とラジカル重合開始剤を含む重合性混合物をキャスト重合させることで、難燃性を有し、かつ耐熱性に優れるメタクリル樹脂組成物からなる難燃板を製造する方法である。
(Production method)
Next, the manufacturing method of the flame-retardant board of this invention is demonstrated .
The production method of the present invention comprises a flame retardant plate comprising a methacrylic resin composition having flame retardancy and excellent heat resistance by cast polymerization of a polymerizable mixture containing the monomer mixture and a radical polymerization initiator. It is a method of manufacturing.
ラジカル重合開始剤としては、例えば、２，２'−アゾビス（イソブチロニトリル）、２，２'−アゾビス（２，４−ジメチルバレロニトリル）などのアゾ化合物；ベンゾイルパーオキサイド、ラウロイルパーオキサイドなどの過酸化物などが挙げられ、必要に応じてそれらの２種以上を用いてもよく、必要に応じて、アミン類などの促進剤と併用してもよい。
ラジカル重合開始剤の添加量は、単量体混合物に対して、通常、０．０１〜１重量部、好ましくは０．０１〜０．５重量部である。
Examples of radical polymerization initiators include azo compounds such as 2,2′-azobis (isobutyronitrile) and 2,2′-azobis (2,4-dimethylvaleronitrile); benzoyl peroxide, lauroyl peroxide, and the like. Two or more of them may be used if necessary, and may be used in combination with an accelerator such as amines if necessary.
The addition amount of the radical polymerization initiator is usually 0.01 to 1 part by weight, preferably 0.01 to 0.5 part by weight with respect to the monomer mixture.
この重合反応の温度は、通常、使用するラジカル重合開始剤の種類等によって、常温〜１５０℃の範囲で適宜設定され、また、必要に応じて多段階の温度条件で重合を行ってもよい。 The temperature of this polymerization reaction is usually appropriately set in the range of room temperature to 150 ° C. depending on the type of radical polymerization initiator to be used and the like, and the polymerization may be performed under multi-stage temperature conditions as necessary.
重合性混合物の重合方法としては、例えば、キャスト重合（注型重合）などの塊状重合；懸濁重合；乳化重合；分散重合などが挙げられるが、本発明では特に、得られるメタクリル樹脂組成物を板状にして使用するので、良好な外観となる点や、大きなサイズの板や厚い板などの生産性の点で、キャスト重合を採用する。
The polymerization method of the polymerizable mixture, if example embodiment, the cast polymerization (casting polymerization) bulk polymerization and the like; suspension; emulsion polymerization; Although such dispersion polymerization Ru. In particular, the resulting methacrylic resin composition in the present invention since use by objects on the plate, and that a good appearance, in terms of productivity, such as large size of the plate or thick plate, employing a casting polymerization.
キャスト重合としては、例えば、上記重合性混合物をセルに注入して重合させるセルキャスト法、対向配置された一対のステンレス製エンドレスベルトを用いる連続キャスト法などが挙げられる。
セルキャスト法に用いられるセルは、例えば、２枚のガラス板と軟質塩化ビニルチューブなどのシール材から構成され、そのセルの空隙の間隔は所望の厚さのメタクリル樹脂組成物が得られるように適宜調整され、一般的には１〜３０ｍｍである。
Examples of the cast polymerization include a cell casting method in which the polymerizable mixture is injected into a cell for polymerization, and a continuous casting method using a pair of stainless endless belts arranged opposite to each other.
The cell used in the cell casting method is composed of, for example, a sealing material such as two glass plates and a soft vinyl chloride tube, and the space between the cells is such that a methacrylic resin composition having a desired thickness can be obtained. It adjusts suitably and generally is 1-30 mm.
このようにして、良好な難燃性に加え、優れた耐熱性を有するメタクリル樹脂組成物からなる難燃板が得られる。
この難燃板は、例えば、照明材料、光学材料、看板、ディスプレイ、建築材料、装飾材料等に利用することができ、特に、ガソリンスタンドなどの可燃性物質を取り扱う場所において、その店名や商品価格等を表示する看板等；高速道路や幹線道路等に設置される透明な遮音板；鉄道高架に設置される防風パネル等に好適に用いられる。なお、このメタクリル樹脂組成物からなる難燃板を、遮音板などの透明性が必要とされる用途に使用する場合、その好ましい全光線透過率は８０％以上であり、より好ましくは９０％以上である。
In this way, a flame retardant plate made of a methacrylic resin composition having excellent heat resistance in addition to good flame resistance is obtained.
This flame retardant plate can be used for lighting materials, optical materials, signboards, displays, building materials, decorative materials, etc., especially in places that handle flammable substances such as gas stations, the store names and product prices. It is suitably used for signboards that display etc .; transparent sound insulation boards installed on highways, main roads, etc .; windproof panels installed on railway overpasses, etc. In addition, when using the flame-retardant board which consists of this methacrylic resin composition for the use where transparency is required, such as a sound insulation board, the preferable total light transmittance is 80% or more, More preferably, it is 90% or more. It is.
以下、本発明の実施例を示すが、本発明はこれらによって限定されるものではない。なお、メタクリル樹脂組成物の難燃性試験、耐熱性試験および全光線透過率測定は、下記の方法で行った。 Examples of the present invention will be described below, but the present invention is not limited thereto. In addition, the flame retardance test of the methacrylic resin composition, the heat resistance test, and the total light transmittance measurement were performed by the following method.
（難燃性試験）
JIS K 6911-1979の耐燃性試験A法に準拠して、3個1組のサンプルにて不燃性、自消性、可燃性の判定を行った。尚、サンプルのうち3個とも不燃性の場合には「◎」、サンプルのうち3個とも自消性の場合には「○」、サンプルのうち3個とも可燃性の場合には「×」を示した。
（耐熱性試験）
JIS K 7191-2に準拠して、80℃の熱風循環炉中で16時間アニールしたサンプルの荷重たわみ温度（℃）を測定した。
（全光線透過率測定）
透過率計（（株）村上色彩技術研究所製の「HR-100」）を用い、JIS K7361-1に準拠して、全光線透過率Ttを測定した。この数値が大きいほど、光線の透過が大きい、つまり透明性が高いことを示す。
(Flame retardancy test)
In accordance with JIS K 6911-1979 flame resistance test method A, non-flammability, self-extinguishability, and flammability were determined using a set of three samples. If all three of the samples are nonflammable, “◎”, if all three of the samples are self-extinguishing, “○”, if all three of the samples are flammable, “×”. showed that.
(Heat resistance test)
In accordance with JIS K 7191-2, the deflection temperature under load (° C.) of a sample annealed for 16 hours in a hot air circulating furnace at 80 ° C. was measured.
(Total light transmittance measurement)
Using a transmittance meter (“HR-100” manufactured by Murakami Color Research Laboratory Co., Ltd.), the total light transmittance Tt was measured in accordance with JIS K7361-1. The larger this value, the greater the light transmission, that is, the higher the transparency.
＜実施例１＞
（メタクリレート系樹脂板の製造）
メタクリル酸メチル 90mol%とジメチル（メタクリロイロキシメチル）ホスホネート （DMMMP，SPECIFIC POLYMERS社製の「MAPC1 ME」(P/N:SP-41-003)）10mol%の単量体混合物100重量部、2,2'-アゾビスイソブチロニトリル（AIBN:ラジカル重合開始剤)0.08重量部、ジ(2-エチルヘキシル)スルホコハク酸ナトリウム (離型剤)0.1重量部、1-メチル-4-イソプロピリデン-1-シクロヘキセン (重合調節剤)0.01重量部および2-(2-ヒドロキシ-5-メチルフェニル)ベンゾトリアゾール (紫外線吸収剤)0.01重量部を混合して得られた重合性混合物を真空脱気した。
次いで、厚さ10mm、300mm四方のガラス同士を対向させ、その両方の面の間に3mm用の軟質塩化ビニル製ガスケット（シール材）を挟み込んで形成されたセルの中空部に、重合性混合物を注入し、室温から72℃まで3時間かけて重合硬化させた後、72℃から120℃まで1時間かけて熱処理し、3mm厚の板状のメタクリル樹脂組成物を得た。
得られたメタクリル樹脂組成物の難燃性、荷重たわみ温度および全光線透過率の測定結果を表1に示す。
<Example 1>
(Manufacture of methacrylate resin plates)
90 parts by weight of methyl methacrylate and 100 parts by weight of monomer mixture of dimethyl (methacryloyloxymethyl) phosphonate (DMMMP, SPECIFIC POLYMERS "MAPC1 ME" (P / N: SP-41-003)) 10 mol% , 2'-Azobisisobutyronitrile (AIBN: radical polymerization initiator) 0.08 parts by weight, sodium di (2-ethylhexyl) sulfosuccinate (release agent) 0.1 parts by weight, 1-methyl-4-isopropylidene-1 A polymerizable mixture obtained by mixing 0.01 part by weight of -cyclohexene (polymerization regulator) and 0.01 part by weight of 2- (2-hydroxy-5-methylphenyl) benzotriazole (ultraviolet absorber) was vacuum degassed.
Next, the polymerizable mixture is placed in the hollow portion of the cell formed by sandwiching a 3mm soft vinyl chloride gasket (sealing material) between both faces of 10mm thick and 300mm square glass. The mixture was injected and polymerized and cured from room temperature to 72 ° C. over 3 hours, and then heat treated from 72 ° C. to 120 ° C. over 1 hour to obtain a plate-like methacrylic resin composition having a thickness of 3 mm.
Table 1 shows the measurement results of flame retardancy, deflection temperature under load, and total light transmittance of the obtained methacrylic resin composition.
＜実施例２＞
ジメチル（メタクリロイロキシメチル）ホスホネート（DMMMP）10mol%に代えて、ジエチル（メタクリロイロキシメチル）ホスホネート（DEMMP，SPECIFIC POLYMERS社製の「MAPC1 ET」(P/N:SP-41-006)）10mol%とした以外は、実施例１に準じて3mm厚の板状のメタクリル樹脂組成物を得た。
得られたメタクリル樹脂組成物の難燃性、荷重たわみ温度および全光線透過率の測定結果を表１に示す。
<Example 2>
10 mol% of dimethyl (methacryloyloxymethyl) phosphonate (DMMMP) instead of 10 mol of diethyl (methacryloyloxymethyl) phosphonate (DEMMP, SPECIFIC POLYMERS “MAPC1 ET” (P / N: SP-41-006)) A plate-like methacrylic resin composition having a thickness of 3 mm was obtained in the same manner as in Example 1 except that the content was%.
Table 1 shows the measurement results of flame retardancy, deflection temperature under load, and total light transmittance of the obtained methacrylic resin composition.
＜比較例１＞
ジメチル（メタクリロイロキシメチル）ホスホネート（DMMMP）10mol%に代えて、ジエチル−ｐ−ビニルベンジルホスホネート(DEBP，片山化学工業（株）製の「S-2」) 10mol%とした以外は、実施例１に準じて3mm厚の板状のメタクリル樹脂組成物を得た。
得られたメタクリル樹脂組成物の難燃性、荷重たわみ温度および全光線透過率の測定結果を表１に示す。
<Comparative Example 1>
Example except that dimethyl (methacryloyloxymethyl) phosphonate (DMMMP) 10 mol% was replaced with 10 mol% diethyl-p-vinylbenzylphosphonate (DEBP, “S-2” manufactured by Katayama Chemical Co., Ltd.) According to 1, a plate-like methacrylic resin composition having a thickness of 3 mm was obtained.
Table 1 shows the measurement results of flame retardancy, deflection temperature under load, and total light transmittance of the obtained methacrylic resin composition.
＜比較例２＞
ジメチル（メタクリロイロキシメチル）ホスホネート（DMMMP）10mol%に代えて、ジフェニルビニルホスホネート(DEVBP，片山化学工業（株）製の「APO-12」) 10mol%とした以外は、実施例１に準じて3mm厚の板状のメタクリル樹脂組成物を得た。
得られたメタクリル樹脂組成物の難燃性、荷重たわみ温度および全光線透過率の測定結果を表１に示す。
<Comparative Example 2>
Except that 10 mol% of dimethyl (methacryloyloxymethyl) phosphonate (DMMMP) was used, diphenylvinylphosphonate (DEVBP, “APO-12” manufactured by Katayama Chemical Co., Ltd.) was changed to 10 mol%. A plate-like methacrylic resin composition having a thickness of 3 mm was obtained.
Table 1 shows the measurement results of flame retardancy, deflection temperature under load, and total light transmittance of the obtained methacrylic resin composition.
Claims (4)
メタクリル酸メチル及び前記ホスホン酸エステルの総量を１００モル％として、メタクリル酸メチルが８０〜９９モル％であり、前記ホスホン酸エステルが１〜２０モル％である単量体混合物、及びラジカル重合開始剤を含む重合性混合物をキャスト重合させることを特徴とする難燃板の製造方法。 And methyl methacrylate, Ri Do and a phosphonic acid ester represented by the following formula (1),
Monomer mixture in which the total amount of methyl methacrylate and the phosphonic acid ester is 100 mol%, methyl methacrylate is 80 to 99 mol%, and the phosphonic acid ester is 1 to 20 mol%, and a radical polymerization initiator A method for producing a flame retardant plate, comprising cast polymerizing a polymerizable mixture containing
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2011223794A JP5827862B2 (en) | 2011-10-11 | 2011-10-11 | Method for producing flame retardant plate comprising methacrylic resin composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2011223794A JP5827862B2 (en) | 2011-10-11 | 2011-10-11 | Method for producing flame retardant plate comprising methacrylic resin composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2013082814A JP2013082814A (en) | 2013-05-09 |
| JP5827862B2 true JP5827862B2 (en) | 2015-12-02 |
Family
ID=48528332
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011223794A Active JP5827862B2 (en) | 2011-10-11 | 2011-10-11 | Method for producing flame retardant plate comprising methacrylic resin composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP5827862B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11879042B2 (en) | 2021-08-02 | 2024-01-23 | B/E Aerospace, Inc. | Fire resistant thermoplastic-based resin for fiber-reinforced composites |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI585144B (en) * | 2014-10-21 | 2017-06-01 | Mitsubishi Rayon Co | (Meth) acrylic resin composition and a resin molded product |
| JP6929293B2 (en) * | 2016-09-30 | 2021-09-01 | 株式会社クラレ | Copolymer composition having a phosphonate group |
| US11505694B2 (en) * | 2018-03-08 | 2022-11-22 | Tdk Corporation | Resin composition, resin cured product and resin substrate |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63117056A (en) * | 1986-11-05 | 1988-05-21 | Mitsubishi Rayon Co Ltd | Flame-retardant acrylic resin composition and production thereof |
| CN1355829A (en) * | 1999-06-11 | 2002-06-26 | 阿托芬纳股份公司 | Method for protecting metals against corrosion and non-polluting reactive composition therefor |
| US20060142520A1 (en) * | 2004-12-27 | 2006-06-29 | 3M Innovative Properties Company | Hole transport layers for organic electroluminescent devices |
| JP2007297451A (en) * | 2006-04-28 | 2007-11-15 | Sumitomo Chemical Co Ltd | Methacrylic resin composition |
| KR20110077881A (en) * | 2009-12-30 | 2011-07-07 | 제일모직주식회사 | Phosphorus acrylic copolymer resin excellent in transparency and flame retardancy and its composition |
-
2011
- 2011-10-11 JP JP2011223794A patent/JP5827862B2/en active Active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11879042B2 (en) | 2021-08-02 | 2024-01-23 | B/E Aerospace, Inc. | Fire resistant thermoplastic-based resin for fiber-reinforced composites |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2013082814A (en) | 2013-05-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| TWI691516B (en) | Copolymer and formed product | |
| JP6805494B2 (en) | (Meta) Acrylic resin composition and resin molded product | |
| JP5827862B2 (en) | Method for producing flame retardant plate comprising methacrylic resin composition | |
| JP2011046835A (en) | Methacrylic resin composition | |
| KR102145085B1 (en) | Copolymer and molded body | |
| JP6213131B2 (en) | Methacrylic resin composition, method for producing the same, and resin molded body | |
| JP5515209B2 (en) | Methacrylic resin composition and method for producing methacrylic resin composition | |
| TWI644928B (en) | (Meth)acrylic resin composition, resin molded body, resin Method for producing laminated body and (meth)acrylic resin composition | |
| JP6790436B2 (en) | Method for Producing (Meta) Acrylic Resin Composition, Resin Mold, and (Meta) Acrylic Resin Composition | |
| JP2018154763A (en) | (meth)acrylic resin composition and resin molding | |
| JP6809496B2 (en) | (Meta) Acrylic resin composition, resin molded product, lighting cover and lighting sign | |
| WO2013161267A1 (en) | Methacrylic resin composition | |
| JPH11152341A (en) | Flame-retardant methacrylic resin plate, its production, and sound-isolating panel | |
| JPH06100712A (en) | Flame retardant acrylic resin sheet | |
| WO2022202743A1 (en) | Monomer mixture, resin composition, resin molded article, panel for aquariums, illuminated sign, building component, method for producing resin composition, and method for manufacturing resin cast board | |
| JP7298654B2 (en) | (Meth)acrylic resin composition and resin molding | |
| WO2023249036A1 (en) | Resin composition, resin molded body, and method for producing same | |
| JP2011046799A (en) | Methacrylic resin composition | |
| JPS63113063A (en) | Flame-retardant acrylic resin composition and production thereof | |
| JPS5943046A (en) | Flame-retardant acrylic resin composition and production thereof | |
| JP2001261738A (en) | Methacrylate based resin excellent in crystal clarity and weatherability and production method of the same | |
| JP2008260880A (en) | Method for manufacturing methacrylic resin plate |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20140716 |
|
| A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20150116 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20150120 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20150318 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20151006 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20151019 |
|
| R150 | Certificate of patent or registration of utility model |
Ref document number: 5827862 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| RD04 | Notification of resignation of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: R3D04 |
|
| R157 | Certificate of patent or utility model (correction) |
Free format text: JAPANESE INTERMEDIATE CODE: R157 |
|
| S531 | Written request for registration of change of domicile |
Free format text: JAPANESE INTERMEDIATE CODE: R313531 |
|
| R350 | Written notification of registration of transfer |
Free format text: JAPANESE INTERMEDIATE CODE: R350 |