JPH01129013A - Production of unsaturated polyester-imide resin - Google Patents
Production of unsaturated polyester-imide resinInfo
- Publication number
- JPH01129013A JPH01129013A JP28776687A JP28776687A JPH01129013A JP H01129013 A JPH01129013 A JP H01129013A JP 28776687 A JP28776687 A JP 28776687A JP 28776687 A JP28776687 A JP 28776687A JP H01129013 A JPH01129013 A JP H01129013A
- Authority
- JP
- Japan
- Prior art keywords
- resin
- unsaturated
- unsaturated polyester
- heat resistance
- dicarboxylic 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.)
- Pending
Links
- 229920005989 resin Polymers 0.000 title claims abstract description 41
- 239000011347 resin Substances 0.000 title claims abstract description 41
- 229920003055 poly(ester-imide) Polymers 0.000 title claims abstract description 20
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 150000005846 sugar alcohols Polymers 0.000 claims abstract description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- 229920006337 unsaturated polyester resin Polymers 0.000 claims description 2
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 claims 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract description 17
- 150000001991 dicarboxylic acids Chemical class 0.000 abstract description 7
- 238000005470 impregnation Methods 0.000 abstract description 6
- FUTZQQLJVHTGLP-UHFFFAOYSA-N 2-(2-hydroxyethyl)-3a,4,5,7a-tetrahydroisoindole-1,3-dione Chemical compound C1CC=CC2C(=O)N(CCO)C(=O)C21 FUTZQQLJVHTGLP-UHFFFAOYSA-N 0.000 abstract description 5
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 abstract description 4
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 abstract description 4
- 239000000853 adhesive Substances 0.000 abstract description 2
- 230000001070 adhesive effect Effects 0.000 abstract description 2
- 238000001035 drying Methods 0.000 description 7
- 239000002966 varnish Substances 0.000 description 6
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 3
- 238000007605 air drying Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000010526 radical polymerization reaction Methods 0.000 description 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 238000009413 insulation Methods 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- -1 maleic anhydride Chemical class 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 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
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- JHPBZFOKBAGZBL-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylprop-2-enoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)=C JHPBZFOKBAGZBL-UHFFFAOYSA-N 0.000 description 1
- ROLAGNYPWIVYTG-UHFFFAOYSA-N 1,2-bis(4-methoxyphenyl)ethanamine;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1CC(N)C1=CC=C(OC)C=C1 ROLAGNYPWIVYTG-UHFFFAOYSA-N 0.000 description 1
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 239000004641 Diallyl-phthalate Substances 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- NBICYCZLCAMSBG-UHFFFAOYSA-L [Co+2].CCCCCC=CC([O-])=O.CCCCCC=CC([O-])=O Chemical compound [Co+2].CCCCCC=CC([O-])=O.CCCCCC=CC([O-])=O NBICYCZLCAMSBG-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- CZBZUDVBLSSABA-UHFFFAOYSA-N butylated hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- MZZUATUOLXMCEY-UHFFFAOYSA-N cobalt manganese Chemical compound [Mn].[Co] MZZUATUOLXMCEY-UHFFFAOYSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- IFDVQVHZEKPUSC-UHFFFAOYSA-N cyclohex-3-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCC=CC1C(O)=O IFDVQVHZEKPUSC-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- SGGOJYZMTYGPCH-UHFFFAOYSA-L manganese(2+);naphthalene-2-carboxylate Chemical compound [Mn+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 SGGOJYZMTYGPCH-UHFFFAOYSA-L 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 239000002990 reinforced plastic Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 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
- 230000004580 weight loss Effects 0.000 description 1
Landscapes
- Macromonomer-Based Addition Polymer (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
この発明は、耐熱性および空気乾燥性に優れた不飽和ポ
リエステルイミド樹脂の製法に関するものである。DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to a method for producing an unsaturated polyesterimide resin having excellent heat resistance and air drying properties.
従来から不飽和ポリエステルイミド樹脂は希釈モノマー
、添加剤の添加によりフェス化されコイル含浸用等の用
途に用いられるものであり、ラジカル重合により樹脂の
硬化反応が進行する。しかし、このラジカル重合は空気
中の酸素による重合阻止作用を受けるため、空気と接す
る樹脂表面に未重合物が残りべたつきを生じることとな
る。したがって、コイル含浸等に用いられ、空気に接触
した状態で硬化が行われる不飽和ポリエステルイミド樹
脂ワニスには、オクテン酸コバルト、ナフテン酸マンガ
ン等の金属塩を添加、含有させることで樹脂表面のべた
つきの改善がなされている。Conventionally, unsaturated polyesterimide resins have been made into a face by adding diluent monomers and additives and used for applications such as coil impregnation, and the curing reaction of the resin proceeds by radical polymerization. However, since this radical polymerization is inhibited by oxygen in the air, unpolymerized substances remain on the resin surface that comes into contact with the air, resulting in stickiness. Therefore, unsaturated polyesterimide resin varnish used for coil impregnation etc. and cured in contact with air is coated with metal salts such as cobalt octenoate and manganese naphthenate to prevent the resin surface from becoming sticky. Improvements have been made.
しかしながら、上記コバルトマンガン等の金属塩は樹脂
硬化物の酸化劣化を促進するため、コイル含浸等の絶縁
用途に関しては耐熱絶縁寿命が短くなり、また、他の用
途では熱劣化により機械強度が急激に低下するという問
題が生じている。However, metal salts such as cobalt manganese accelerate the oxidative deterioration of cured resin products, which shortens the life of heat-resistant insulation for insulation applications such as coil impregnation, and in other applications, mechanical strength rapidly decreases due to thermal deterioration. The problem is that it is decreasing.
この発明は、このような事情に鑑みなされたもので、そ
れ自身が、耐熱性および樹脂表面の乾燥性に優れている
不飽和ポリエステルイミド樹脂を得る方法の提供をその
目的とする。The present invention was made in view of the above circumstances, and an object of the present invention is to provide a method for obtaining an unsaturated polyesterimide resin which itself has excellent heat resistance and drying properties on the resin surface.
上記の目的を達成するために、この発明の不飽和ポリエ
ステルイミド樹脂の製法は、不飽和二価カルボン酸と、
多価アルコールと、一価アルコールと、場合により飽和
二価カルボン酸とを反応させて不飽和ポリエステル系樹
脂を製造する方法であって、上記一価アルコールとして
、２−テトラヒドロフタルイミドエタノールを主成分と
するものを用いるという構成をとる。In order to achieve the above object, the method for producing an unsaturated polyesterimide resin of the present invention uses an unsaturated dihydric carboxylic acid,
A method for producing an unsaturated polyester resin by reacting a polyhydric alcohol, a monohydric alcohol, and optionally a saturated dihydric carboxylic acid, the method comprising 2-tetrahydrophthalimideethanol as the main component as the monohydric alcohol. The structure is to use what is possible.
すなわち、本発明者らは、不飽和ポリエステルイミド樹
脂に耐熱性および空気乾燥性を付与するために研究を重
ねた結果、テトラヒドロフタル酸とグリコールとの単純
な脱水縮合により良好な樹脂表面の乾燥性が得られるよ
うになることを突き止めた。しかし、このようにしても
耐熱性を有する樹脂を得ることができなかった。そこで
、さらに、研究を重ねた結果、不飽和二価カルボン酸と
、多価アルコールと、２−テトラヒドロフタルイミドエ
タノールを主成分とする上記特殊な一価アルコールと、
場合により飽和二価カルボン酸を用いると、樹脂表面の
乾燥性の向上と同時に樹脂の耐熱性が大幅に改善される
ことを見いだしこの発明に到達した。That is, as a result of repeated research in order to impart heat resistance and air drying properties to unsaturated polyesterimide resins, the present inventors have found that a simple dehydration condensation of tetrahydrophthalic acid and glycol provides good drying properties on the resin surface. It was found that the following results can be obtained. However, even with this method, it was not possible to obtain a resin having heat resistance. Therefore, as a result of further research, the above-mentioned special monohydric alcohol whose main components are unsaturated dihydric carboxylic acid, polyhydric alcohol, and 2-tetrahydrophthalimidoethanol,
The inventors have discovered that when a saturated dihydric carboxylic acid is used in some cases, the drying properties of the resin surface and the heat resistance of the resin are significantly improved, and the present invention has been achieved.
この発明に係る不飽和ポリエステルイミド樹脂は、不飽
和二価カルボン酸（ａ）、多価アルコール（ｂ）、２−
テトラヒドロフタルイミドエタノールを主成分とする一
価アルコール（ｃ）、さら、に場合により飽和二価カル
ボン酸（ｄ）を用いて得られる。The unsaturated polyesterimide resin according to the present invention includes an unsaturated dicarboxylic acid (a), a polyhydric alcohol (b), a 2-
Tetrahydrophthalimide is obtained by using a monohydric alcohol (c) containing ethanol as a main component, and optionally a saturated dihydric carboxylic acid (d).
上記不飽和二価カルボン酸としては、無水マレイン酸、
フマル酸等があげられ、このような不飽和二価カルボン
酸の使用量は、樹脂成分〔（ａ）〜（ｄ）の仕込み時の
合計量〕に対して１５〜５０重量％（以下「％」と略す
）の範囲内に設定することが好ましい。The unsaturated dicarboxylic acids mentioned above include maleic anhydride,
Examples include fumaric acid, and the amount of such unsaturated dicarboxylic acids used is 15 to 50% by weight (hereinafter referred to as "%") based on the resin component [total amount at the time of preparation of (a) to (d)]. It is preferable to set it within the range of .
上記多価アルコールとしては、エチレングリコール、ジ
エチレングリコール、プロピレングリコール、ジプロピ
レングリコールおよびネオペンチルグリコール等が用い
られる。これら多価アルコールの使用量は、樹脂成分に
対して１０〜５０％の範囲内に設定することが効果の点
で好ましい。As the polyhydric alcohol, ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol, neopentyl glycol, etc. are used. From the viewpoint of effectiveness, it is preferable that the amount of these polyhydric alcohols used is set within the range of 10 to 50% based on the resin component.
また、上記一価アルコールとしては、下記の構造式で示
される２−テトラヒドロフタルイミドエタノールを主成
分とするものが用いられる。なお、この発明において、
主成分とするとは、全体が主成分のみで構成されている
場合も含める趣旨である。Further, as the above-mentioned monohydric alcohol, one whose main component is 2-tetrahydrophthalimideethanol represented by the following structural formula is used. In addition, in this invention,
The term "main component" is intended to include cases where the entire component is composed only of the main component.
このような２−テトラヒドロフタルイミドエタノールの
含有量は、添加される全アルコールの１０〜７０モル％
、好ましくは２５〜５０モル％の範囲内に設定すること
が好結果をもたらす。すなわち、１０モル％を下回ると
樹脂の耐熱性および空気乾燥性が不充分となり、７０モ
ル％を上回ると樹脂硬化物の強度が低下する傾向がみら
れるからである。The content of such 2-tetrahydrophthalimide ethanol is 10 to 70 mol% of the total alcohol added.
, preferably within the range of 25 to 50 mol %, yields good results. That is, if it is less than 10 mol %, the heat resistance and air drying properties of the resin will be insufficient, and if it exceeds 70 mol %, the strength of the cured resin product will tend to decrease.
さらに、場合により飽和二価カルボン酸として、フタル
酸、イソフタル酸、テレフタル酸、アジピン酸およびテ
トラヒドロ無水フタル酸等が、樹脂に対する柔軟性付与
物として、上記樹脂成分に対して０〜２５％の範囲内で
用いられる。Furthermore, in some cases, saturated dihydric carboxylic acids such as phthalic acid, isophthalic acid, terephthalic acid, adipic acid, and tetrahydrophthalic anhydride may be used as flexibility imparters to the resin in a range of 0 to 25% based on the resin component. used within.
このような不飽和ポリエステルイミド樹脂の製造は、例
えばつぎのようにして行うことができる。すなわち、テ
トラヒドロ無水フタル酸とモノエタノールアミンを反応
させて２−テトラヒドロフタルイミドエタノールからな
る一価アルコールをつくる。つぎに、これに、エチレン
グリコール等の多価アルコールと無水マレイン酸等の不
飽和二価カルボン酸および必要により重合防止剤を添加
し加熱反応させて不飽和ポリエステルイミド樹脂をつく
るということにより行われる。このようにして得られた
樹脂に希釈モノマーを加えて、低粘度化することにより
不飽和ポリエステルイミド樹脂フェスが製造される。Such an unsaturated polyesterimide resin can be produced, for example, as follows. That is, a monohydric alcohol consisting of 2-tetrahydrophthalimidoethanol is produced by reacting tetrahydrophthalic anhydride with monoethanolamine. Next, a polyhydric alcohol such as ethylene glycol, an unsaturated dicarboxylic acid such as maleic anhydride, and, if necessary, a polymerization inhibitor are added to this, and the reaction is heated to produce an unsaturated polyesterimide resin. . An unsaturated polyesterimide resin face is produced by adding a diluent monomer to the resin thus obtained to lower the viscosity.
なお、上記重合防止剤として、ハイドロキノン、ブチル
ヒドキシアニソールおよびベンゾキノン等が用いられる
。Note that hydroquinone, butylhydroxyanisole, benzoquinone, and the like are used as the polymerization inhibitor.
また、上記希釈モノマーとしては、スチレン。Further, the diluent monomer is styrene.
ビニルトルエン、ジアリルフタレート、ジアリルイソフ
タレート、アクリルエステルおよびメタクリルエステル
等が用いられる。そして、上記希釈モノマーの添加量は
、得られた不飽和ポリエステルイミド樹脂に対して５０
〜１５０％の範囲内に設定するのが好ましい。Vinyl toluene, diallyl phthalate, diallyl isophthalate, acrylic ester, methacrylic ester, etc. are used. The amount of the diluent monomer added was 50% based on the obtained unsaturated polyesterimide resin.
It is preferable to set it within the range of ~150%.
以上のように、この発明により得られる不飽和ポリエス
テルイミド樹脂は、樹脂中に２−テトラヒドロフタルイ
ミドエタノールから誘導される構造部分を有するため、
表面乾燥性および耐熱性に優れている。したがって、電
気機器のコイル含浸用の用途のみならず、積層板１強化
プラスチック（ＦＲＰ）および接着剤等の用途に適し、
かつ、優れた表面乾燥性を有するためにコイル含浸およ
び接着等の工程の時間短縮を実現できる。As described above, since the unsaturated polyesterimide resin obtained by the present invention has a structural part derived from 2-tetrahydrophthalimideethanol in the resin,
Excellent surface drying and heat resistance. Therefore, it is suitable not only for coil impregnation of electrical equipment, but also for applications such as laminate 1 reinforced plastic (FRP) and adhesives.
In addition, since it has excellent surface drying properties, it is possible to shorten the time required for processes such as coil impregnation and adhesion.
つぎに、実施例について比較例と併せて説明する。Next, examples will be described together with comparative examples.
〔実施例１〕
精留管、温度調節器、撹拌機および加熱装置付きの四つ
ロフラスコ（容積Ｉｆ）にテトラヒドロ無水フタル酸０
．５モル、モノエタノールアミン０゜５モルを仕込み、
２００°Ｃまで徐々に加熱した後、冷却し、２−テトラ
ヒドロフタルイミドエタノールヲ得た。これに、エチレ
ングリコール０．８５モル、無水マレイン酸１モル、ハ
イドロキノン３００ｐｐｍを加え、窒素ガス雰囲気下１
９０°Ｃまで加熱し、そのまま６時間反応させ、酸価１
８の不飽和ポリエステルイミド樹脂を得た。つぎに、上
記樹脂５０重量部（以下「部」と略す）に対してスチレ
ン５０部を加え希釈して樹脂溶液粘度０．６ポイズの不
飽和ポリエステルイミド樹脂ワニスを得た。[Example 1] Tetrahydrophthalic anhydride (0) was placed in a four-loaf flask (volume If) equipped with a rectifying tube, a temperature controller, a stirrer, and a heating device.
．． Prepare 5 moles of monoethanolamine and 0.5 moles of monoethanolamine.
After gradually heating to 200°C, the mixture was cooled to obtain 2-tetrahydrophthalimideethanol. To this, 0.85 mol of ethylene glycol, 1 mol of maleic anhydride, and 300 ppm of hydroquinone were added, and 1 mol of ethylene glycol was added under a nitrogen gas atmosphere.
Heated to 90°C and allowed to react for 6 hours until the acid value reached 1.
An unsaturated polyesterimide resin No. 8 was obtained. Next, 50 parts by weight (hereinafter abbreviated as "parts") of the resin was diluted by adding 50 parts of styrene to obtain an unsaturated polyesterimide resin varnish having a resin solution viscosity of 0.6 poise.
〔実施例２〜６、比較例１〜３〕
各成分原料を後記の第１表に示す割合の成分原料に代え
た。それ以外は実施例１と同様にして不飽和ポリエステ
ルイミド樹脂ワニスを得た。[Examples 2 to 6, Comparative Examples 1 to 3] Each component raw material was replaced with component raw materials in the proportions shown in Table 1 below. An unsaturated polyesterimide resin varnish was obtained in the same manner as in Example 1 except for the above.
（余 白 ）
以上の実施例および比較例によって得られた不飽和ポリ
エステルイミド樹脂ワニス１００部に対して、ｔ−ブチ
ルパーベンゾエート１部を添加し、０．３Ｘ５０Ｘ１８
０ｍｍの鉄板に上記ワニスを塗布した後、１５０°Ｃ×
１５分硬化を行い表面乾燥性を評価した。また、底面６
０ｍａ＋φのガラスシャーレに上記ワニス３ｇを取り、
１５０°Ｃ×２０時間硬化を行った後、２５０°Ｃの熱
風乾燥機中に４０日間放置した後の重量減少率を測定し
、加熱減量として後記の第２表に、上記表面乾燥性と併
せて示した。(Margin) 1 part of t-butyl perbenzoate was added to 100 parts of the unsaturated polyesterimide resin varnish obtained in the above Examples and Comparative Examples, and 0.3X50X18
After applying the above varnish to a 0mm steel plate, heat at 150°C
Curing was performed for 15 minutes and surface drying properties were evaluated. Also, the bottom surface 6
Take 3g of the above varnish in a 0ma+φ glass petri dish,
After curing at 150°C for 20 hours, the weight loss rate was measured after being left in a hot air dryer at 250°C for 40 days. It was shown.
（以下余白）
第２表から、実施倒置は比較装置に比べて低粘度で加熱
減量が低いことから耐熱性に優れ、また、表面乾燥性に
も優れていることがわかる。(The following is a blank space) From Table 2, it can be seen that the practical inversion has a lower viscosity and lower heating loss than the comparative device, and therefore has excellent heat resistance and also excellent surface drying properties.
特許出願人 日東電気工業株式会社 代理人 弁理士 西 藤 征 彦Patent applicant: Nitto Electric Industry Co., Ltd. Agent: Patent attorney Yukihiko Nishifuji
Claims (1)
価アルコールと、場合により飽和二価カルボン酸とを反
応させて不飽和ポリエステル系樹脂を製造する方法であ
つて、上記一価アルコールとして、２−テトラヒドロフ
タルイミドエタノールを主成分とするものを用いること
を特徴とする不飽和ポリエステルイミド樹脂の製法。(1) A method for producing an unsaturated polyester resin by reacting an unsaturated dicarboxylic acid, a polyhydric alcohol, a monohydric alcohol, and optionally a saturated dihydric carboxylic acid, the method comprising: 1. A method for producing an unsaturated polyesterimide resin, characterized in that the main component thereof is 2-tetrahydrophthalimide ethanol.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP28776687A JPH01129013A (en) | 1987-11-12 | 1987-11-12 | Production of unsaturated polyester-imide resin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP28776687A JPH01129013A (en) | 1987-11-12 | 1987-11-12 | Production of unsaturated polyester-imide resin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH01129013A true JPH01129013A (en) | 1989-05-22 |
Family
ID=17721478
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP28776687A Pending JPH01129013A (en) | 1987-11-12 | 1987-11-12 | Production of unsaturated polyester-imide resin |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH01129013A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008071360A1 (en) * | 2006-12-15 | 2008-06-19 | Cray Valley S.A. | Unsaturated polyester resins functionalised by unsaturated cycloaliphatic imides for coating and moulding compositions |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5189592A (en) * | 1974-12-21 | 1976-08-05 | Kokasei tainetsuseifuhowahoriesuterujushinoseiho | |
| JPS53127594A (en) * | 1977-04-13 | 1978-11-07 | Mitsubishi Electric Corp | Production of unsaturated polyester resin |
| JPS56129217A (en) * | 1980-03-14 | 1981-10-09 | Mitsubishi Electric Corp | Curable resin composition |
| JPS56129218A (en) * | 1980-03-14 | 1981-10-09 | Mitsubishi Electric Corp | Curable resin composition |
-
1987
- 1987-11-12 JP JP28776687A patent/JPH01129013A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5189592A (en) * | 1974-12-21 | 1976-08-05 | Kokasei tainetsuseifuhowahoriesuterujushinoseiho | |
| JPS53127594A (en) * | 1977-04-13 | 1978-11-07 | Mitsubishi Electric Corp | Production of unsaturated polyester resin |
| JPS56129217A (en) * | 1980-03-14 | 1981-10-09 | Mitsubishi Electric Corp | Curable resin composition |
| JPS56129218A (en) * | 1980-03-14 | 1981-10-09 | Mitsubishi Electric Corp | Curable resin composition |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008071360A1 (en) * | 2006-12-15 | 2008-06-19 | Cray Valley S.A. | Unsaturated polyester resins functionalised by unsaturated cycloaliphatic imides for coating and moulding compositions |
| FR2910012A1 (en) * | 2006-12-15 | 2008-06-20 | Cray Valley S A Sa | UNSATURATED POLYESTERS RESINS FUNCTIONALIZED BY UNSATURATED CYCLOALIPHATIC IMIDES, FOR COATINGS AND MOLDING COMPOSITIONS |
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