JPS59109508A - Low-odor resin composition - Google Patents

Low-odor resin composition

Info

Publication number
JPS59109508A
JPS59109508A JP21890082A JP21890082A JPS59109508A JP S59109508 A JPS59109508 A JP S59109508A JP 21890082 A JP21890082 A JP 21890082A JP 21890082 A JP21890082 A JP 21890082A JP S59109508 A JPS59109508 A JP S59109508A
Authority
JP
Japan
Prior art keywords
resin composition
low
unsaturated polyester
methacrylic acid
odor
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.)
Pending
Application number
JP21890082A
Other languages
Japanese (ja)
Inventor
Hideo Nakamoto
中本 英夫
Shiruyoshi Matsumoto
松本 鶴義
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Mitsubishi Rayon Co Ltd
Original Assignee
Mitsubishi Rayon 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 Mitsubishi Rayon Co Ltd filed Critical Mitsubishi Rayon Co Ltd
Priority to JP21890082A priority Critical patent/JPS59109508A/en
Publication of JPS59109508A publication Critical patent/JPS59109508A/en
Pending legal-status Critical Current

Links

Landscapes

  • Macromonomer-Based Addition Polymer (AREA)

Abstract

PURPOSE:To low-odor unsaturated polyester resin composition, prepared by using a dimethyl ester of a dimerized methacrylic acid as a crosslinking monomer component. CONSTITUTION:An unsaturated polyester resin body (e.g., ''Yupika 8542'', a product of Nippon Yupika Co., Ltd.) is mixed with a dimethyl ester of dimerized methacrylic acid of the formula, and about 0.5-10wt%, based on the resin composition, curing agent, preferably, an organic peroxide whose 10hr half-life decomposition temperature is above 90 deg.C, e.g., t-butyl perbenzoate.

Description

【発明の詳細な説明】 本発明は、低臭気性の不飽和ポリエステル系樹脂組成物
に関する。
DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a low odor unsaturated polyester resin composition.

従来、不飽和ポリエステル樹脂は機械的特性。Traditionally, unsaturated polyester resins have poor mechanical properties.

電気的特性、耐熱性2作業性、安価などの特性を生かし
て繊維強化プラスチック、塗料、接着剤、電気部品など
の分野で多量に使用されてきた。
It has been used in large quantities in fields such as fiber-reinforced plastics, paints, adhesives, and electrical parts due to its electrical properties, heat resistance, workability, and low cost.

不飽和ポリエステル樹脂は主としてボディおよび架橋性
単量体からなり、一般に架橋性単量体が20〜60重量
%含まれている。従来、特性的または経済的な観点から
使用されている架橋性単量体としてはスチレンがほとん
どである。
The unsaturated polyester resin mainly consists of a body and a crosslinkable monomer, and generally contains 20 to 60% by weight of the crosslinkable monomer. Conventionally, most of the crosslinking monomers used from the viewpoint of properties or economy are styrene.

このスチレンは揮散しやすく、硬化時にフェスの20〜
40!景チが揮発して刺激臭を発生するため、作業者や
地域住民に不快臭を与え、健康管理上問題となり法規制
が行なわれるようになった。
This styrene is easy to volatilize, and when it hardens, it
40! The chlorine evaporates and produces a pungent odor, which gives off an unpleasant odor to workers and local residents, posing a health management problem that has led to legislation being put in place.

本発明者らはかかる事情に鑑みてスチレンに代るべき低
臭気性の架橋性単量体について鋭意検討した結果、従来
のビニル樹脂に代る新しい樹脂を見出した。
In view of the above circumstances, the present inventors conducted intensive studies on low-odor crosslinking monomers that could replace styrene, and as a result, discovered a new resin that could replace conventional vinyl resins.

本発明は、(1)不飽和ポリエステル樹脂ボディ、(2
)メタクリル酸2量体ジメチルエステル、(3)硬化剤
を含有してなる低臭気性の不飽和ポリエステル樹脂組成
物に関する。
The present invention comprises (1) an unsaturated polyester resin body, (2)
) methacrylic acid dimer dimethyl ester; and (3) a curing agent.

本発明を実施する際に用いる不飽和ポリエステル樹脂ボ
ディは、・一般に使用されているボディが用いられ、工
業的に生産されているアルコ−ル成分、酸成分、必要に
より変性剤を縮合反応することにより得られるもので、
特に限定されたものではない。
The unsaturated polyester resin body used in carrying out the present invention is a commonly used body, which is prepared by condensation reaction with an industrially produced alcohol component, acid component, and optionally a modifier. It is obtained by
It is not particularly limited.

本発明の第2成分であるメタクリル酸2量体ジメチルエ
ステルは、メタクリル酸メチルの合成時に副生するもの
で、次式に示す化学構造を有している。
Methacrylic acid dimer dimethyl ester, which is the second component of the present invention, is a by-product during the synthesis of methyl methacrylate, and has the chemical structure shown in the following formula.

CH。CH.

このメタクリル酸2量体ジメチルエステルは常圧におけ
る沸点が235℃と高く、はとんど無臭に近い架橋性単
量体である。
This methacrylic acid dimer dimethyl ester has a high boiling point of 235° C. at normal pressure, and is a crosslinkable monomer that is almost odorless.

本発明の第三の成分である硬化剤としては有機過酸化物
、たとえばベンゾイルパーオキサイド、アセチルパーオ
キサイドなどのアシルバーオキサイド、ターシャリブチ
ルパーオキサイド。
The curing agent, which is the third component of the present invention, is an organic peroxide, such as asyl oxide such as benzoyl peroxide or acetyl peroxide, or tert-butyl peroxide.

キュメンヒドロキシパーオキサイドなどのヒドロパーオ
キサイド、メチルエチルケトンパーオキサイド、シクロ
ヘキサノ/パーオキサイドなどのケトンパーオキサイド
、ジターシャリブチルパー7キサイド、ジクミルパーオ
キサイドなどのジアルキルパーオキサイド、ターシャリ
ブチルパーベンゾエート、ターシャリブチルバーオキシ
アセテートなどのオキシパーオキサイドなどを用いるの
が望ましい。
Hydroperoxides such as cumene hydroxy peroxide, ketone peroxides such as methyl ethyl ketone peroxide, cyclohexano/peroxide, dialkyl peroxides such as ditertiary butyl per7oxide, dicumyl peroxide, tertiary butyl perbenzoate, tertiary butyl peroxide, etc. It is desirable to use oxyperoxide such as butyl peroxyacetate.

前記メタクリル酸2量体ジメチルエステルは他のビニル
モノマーと比較して単独重合性ならびに共重合性が若干
低いため、前記有機過酸化物のなかでもとくにその半減
期10時間を得るための分解温度が90℃以上であるも
のが好適であり、完全硬化に要する時間が短縮される。
Since the methacrylic acid dimer dimethyl ester has slightly lower homopolymerizability and copolymerizability than other vinyl monomers, the decomposition temperature for obtaining a half-life of 10 hours is particularly high among the organic peroxides. A temperature of 90° C. or higher is preferable, and the time required for complete curing is shortened.

該硬化剤の添加量は、一般的に樹脂組成物に対して0.
5〜10重量係、好ましくは1〜5重量係の範囲である
The amount of the curing agent added to the resin composition is generally 0.
It ranges from 5 to 10 parts by weight, preferably from 1 to 5 parts by weight.

本発明の樹脂組成物には、耐熱性向上を目的として多官
能(メタ)アクリレート類や低収縮を狙いとする熱可塑
性樹脂、たとえば飽和ポリエステル樹脂、アクリル樹脂
、ビニル樹脂などや充填剤、たとえばシリカ、タルク、
炭酸カルシウム、アスベスト、ガラス繊維、木粉および
着色剤などを必要に応じて添加できる。
The resin composition of the present invention contains polyfunctional (meth)acrylates for the purpose of improving heat resistance, thermoplastic resins for low shrinkage such as saturated polyester resins, acrylic resins, vinyl resins, etc., and fillers such as silica. ,talc,
Calcium carbonate, asbestos, glass fiber, wood flour, coloring agents, etc. can be added as necessary.

次に本発明を実施例および比較例により説明するが、本
発明はこれらにより限定されるものではない。
Next, the present invention will be explained with reference to Examples and Comparative Examples, but the present invention is not limited thereto.

実施例1 イソフタル酸系不飽和ポリエステル樹脂、ユビカ■85
42(日本ユビカKK製、不飽和ポリエステル樹脂ボデ
ィ)100F、メタクリル酸2量体ジメチルエステル3
57’、ターシャリブチルパーベンゾエート5Pを混合
して樹脂組成物を得た。
Example 1 Isophthalic acid-based unsaturated polyester resin, Yubika ■85
42 (manufactured by Nippon Yubika KK, unsaturated polyester resin body) 100F, methacrylic acid dimer dimethyl ester 3
57' and tert-butyl perbenzoate 5P were mixed to obtain a resin composition.

比較例1 実施例1で、メタクリル酸2−1it体ジメチルエステ
ルの代りにスチレンを用いる他は全り実施例1と同じ方
法で樹脂組成物を得た。
Comparative Example 1 A resin composition was obtained in the same manner as in Example 1, except that styrene was used instead of methacrylic acid 2-1 it dimethyl ester.

実施例1および比較例1で得た樹脂組成物をガラス成型
器に流し込み、140℃で4時間加熱せしめた。この注
型物から切り出した試験片について、ガラス転移温度9
曲げ強度2曲げ弾性率、伸度ならびに硬化前の樹脂組成
物の揮発性測定結果を表−1に示す。
The resin compositions obtained in Example 1 and Comparative Example 1 were poured into a glass molder and heated at 140° C. for 4 hours. The glass transition temperature of the test piece cut from this cast material was 9
Table 1 shows the measurement results of bending strength 2, bending modulus, elongation, and volatility of the resin composition before curing.

上記の結果かられかるように、本発明になる樹脂組成物
は、スチレン使用の不飽和ポリエステル樹脂と比べ、硬
化物のガラス転移温度1曲げ強度および曲げ弾性率が若
干劣るものの、伸度が大きく、かつ極めて揮発性分が少
なく、硬化時においても低臭気性であるといつ物像を有
している。
As can be seen from the above results, the resin composition of the present invention has a slightly inferior glass transition temperature 1 bending strength and bending elastic modulus of the cured product compared to unsaturated polyester resin using styrene, but has a large elongation. It also has an extremely low volatile content and low odor even when cured.

表  −1 * 60φ金属シヤーレに樹脂組成物10!を入れ、5
0℃で4時間加熱後の重置変化を求めた。
Table-1 *Resin composition 10 on 60φ metal shear plate! and 5
The superposition change after heating at 0° C. for 4 hours was determined.

実施例2 =ビヵ■8542 □oot12,7リヤ酸2量体ジメ
チ酸二量体ジメチルエストリメチロールプロパントリメ
タクリレート15部、ターシャリプチルパーぺ/シェー
ド6部を混合攪拌して樹脂組成物を得た。次いで該組成
物を140℃で4時間加熱して硬化させたところ、ガラ
ス転移温度が130℃の硬化物が得られた。この硬化物
は実施例1におけると同様極めて揮発性成分が少なく、
硬化時においても臭気の発生は殆んどなかった。
Example 2 = Vika ■ 8542 □oot 12,7 phosphoric acid dimer dimethic acid dimer 15 parts of dimethyl estrimethylol propane trimethacrylate and 6 parts of tertiary butyl perpe/shade were mixed and stirred to form a resin composition. Obtained. Next, the composition was cured by heating at 140°C for 4 hours, and a cured product with a glass transition temperature of 130°C was obtained. This cured product has very few volatile components as in Example 1,
Almost no odor was generated even during curing.

Claims (1)

【特許請求の範囲】 1、  (IJ不飽和ポリエステル樹脂ボディ、(2j
メタクリル酸2を体ジメチルエステル、(3)硬化剤を
含有してなる低臭気性の樹脂組成物。 2、硬化剤が半減期10時間を得るための分解温度が9
0℃以上である有機過酸化物である特許請求の範囲第1
項記載の樹脂組成物。
[Claims] 1. (IJ unsaturated polyester resin body, (2j
A low-odor resin composition comprising dimethyl ester of methacrylic acid 2 and (3) a curing agent. 2. The decomposition temperature for the curing agent to obtain a half-life of 10 hours is 9
Claim 1, which is an organic peroxide having a temperature of 0°C or higher
The resin composition described in .
JP21890082A 1982-12-14 1982-12-14 Low-odor resin composition Pending JPS59109508A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP21890082A JPS59109508A (en) 1982-12-14 1982-12-14 Low-odor resin composition

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP21890082A JPS59109508A (en) 1982-12-14 1982-12-14 Low-odor resin composition

Publications (1)

Publication Number Publication Date
JPS59109508A true JPS59109508A (en) 1984-06-25

Family

ID=16727067

Family Applications (1)

Application Number Title Priority Date Filing Date
JP21890082A Pending JPS59109508A (en) 1982-12-14 1982-12-14 Low-odor resin composition

Country Status (1)

Country Link
JP (1) JPS59109508A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0413290A2 (en) * 1989-08-14 1991-02-20 Mitsubishi Rayon Co., Ltd Material for dentistry
JP2010242065A (en) * 2009-03-17 2010-10-28 Mitsubishi Rayon Co Ltd Non-petroleum-based thermoplastic resin composition and molding

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0413290A2 (en) * 1989-08-14 1991-02-20 Mitsubishi Rayon Co., Ltd Material for dentistry
JP2010242065A (en) * 2009-03-17 2010-10-28 Mitsubishi Rayon Co Ltd Non-petroleum-based thermoplastic resin composition and molding

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