JPH023413A - Production of solid epoxy resin - Google Patents
Production of solid epoxy resinInfo
- Publication number
- JPH023413A JPH023413A JP1016079A JP1607989A JPH023413A JP H023413 A JPH023413 A JP H023413A JP 1016079 A JP1016079 A JP 1016079A JP 1607989 A JP1607989 A JP 1607989A JP H023413 A JPH023413 A JP H023413A
- Authority
- JP
- Japan
- Prior art keywords
- epoxy resin
- acid
- molecular weight
- anhydride
- ethylene
- 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
- 239000003822 epoxy resin Substances 0.000 title claims abstract description 21
- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 21
- 239000007787 solid Substances 0.000 title claims abstract description 5
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 15
- 239000002253 acid Substances 0.000 claims abstract description 10
- 238000010438 heat treatment Methods 0.000 claims abstract description 10
- 239000004593 Epoxy Substances 0.000 claims abstract description 8
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 claims abstract description 8
- 239000003054 catalyst Substances 0.000 claims abstract description 6
- -1 polyethylene terephthalate Polymers 0.000 claims abstract description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims abstract description 3
- 150000003512 tertiary amines Chemical class 0.000 claims abstract description 3
- 125000005207 tetraalkylammonium group Chemical group 0.000 claims abstract description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 15
- 239000005977 Ethylene Substances 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 8
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 6
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 claims description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 5
- 125000003700 epoxy group Chemical group 0.000 claims description 5
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 4
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 3
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims description 2
- 239000001361 adipic acid Substances 0.000 claims description 2
- 235000011037 adipic acid Nutrition 0.000 claims description 2
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims description 2
- RWYFURDDADFSHT-RBBHPAOJSA-N diane Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1.C1=C(Cl)C2=CC(=O)[C@@H]3CC3[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(C)=O)(OC(=O)C)[C@@]1(C)CC2 RWYFURDDADFSHT-RBBHPAOJSA-N 0.000 claims description 2
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 claims 1
- 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 claims 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 claims 1
- 229940014800 succinic anhydride Drugs 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 abstract description 3
- 229920000139 polyethylene terephthalate Polymers 0.000 abstract 2
- 239000005020 polyethylene terephthalate Substances 0.000 abstract 2
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 4
- 150000001991 dicarboxylic acids Chemical class 0.000 description 3
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 2
- KUBDPQJOLOUJRM-UHFFFAOYSA-N 2-(chloromethyl)oxirane;4-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound ClCC1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 KUBDPQJOLOUJRM-UHFFFAOYSA-N 0.000 description 1
- 240000008669 Hedera helix Species 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 229920003232 aliphatic polyester Polymers 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000004132 cross linking Methods 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
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 239000007858 starting material Substances 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/02—Polycondensates containing more than one epoxy group per molecule
- C08G59/12—Polycondensates containing more than one epoxy group per molecule of polycarboxylic acids with epihalohydrins or precursors thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Epoxy Resins (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Paints Or Removers (AREA)
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明の目的は低分子量のエポキシ樹脂の鎖長を長くす
ることにより中分子顔および高・分子間の固体エポキシ
樹脂を製造することである。Detailed Description of the Invention (Industrial Field of Application) The purpose of the present invention is to produce medium-molecular and high-molecular solid epoxy resins by increasing the chain length of low-molecular-weight epoxy resins. .
（従来の技術）
エポキシ樹脂の分子量を増加させる方法としては、ジフ
ェノールやグリコール、アミン、ジカルボン酸のような
、活性水素原子を持つ二官能化合物との反応の結果とし
て低分子量および中分子ｍのエポキシ樹脂の鎖長を長く
する方法が知られている。ジカルボン酸の他に、分子鎖
の両端にカルボキシル基を有する１、４−ブチレングリ
コールとセバシン酸のポリエステルのような脂肪続ポリ
エルテルジカルボン酸が、この目的のために用いらレタ
（Ｂａｔｚｅｒ Ｉｌ、、 Ｌｅｈｓｅ Ｆ、、 ５ｃ
ｈｎ＋ｉｄ Ｒ，：Ａｎｇｅｗ、 Ｈａｋｒｏｎ＋ｏ１
．Ｃｈｅｍ、 ２９／３０．３８８／１９７３／；にｒ
ｅｉｂｉｃｈ Ｕ、、 Ｓｃｈｍｉｄ Ｈ，： Ｐｒｏ
ｇｒ、 ＣＣｏ１１ｏｉｄＰｏｌｙ、Ｓｃｉ、６２．１
０６．１９７７ ＞。(Prior art) A method for increasing the molecular weight of epoxy resins is to increase the molecular weight of low and medium molecular weight m as a result of reaction with bifunctional compounds having active hydrogen atoms, such as diphenols, glycols, amines, and dicarboxylic acids. A method of increasing the chain length of epoxy resin is known. Besides dicarboxylic acids, aliphatic polyester dicarboxylic acids such as polyesters of 1,4-butylene glycol and sebacic acid, which have carboxyl groups at both ends of the molecular chain, have been used for this purpose. Lehse F,, 5c
hn+id R, :Angew, Hakron+o1
．． Chem, 29/30.388/1973/;
eibich U, Schmid H: Pro
gr, CCo11oidPoly, Sci, 62.1
06.1977>.
このように形成した１ボキシ樹脂を架橋した後、ゴム状
生成物が得られる。After crosslinking the 1-boxy resin thus formed, a rubbery product is obtained.
（解決しようとする課題を解決するための手段）現在、
次のことが判明した。即ち、機械的に耐久性のガラス状
被覆剤を得るために適するエポキシ樹脂は、酸価６０〜
４００ＩｔｇＫＯＨ／９の末端カルボキシル基を有する
エチレンポリテレフタレートと、エポキシｆｊ６０．１
８〜０．５５モル／１００ｇの低分子針あるいは中分子
量のエポキシ樹脂とを、触媒を添加し、カルボキシル基
対エポキシ基のモル比を１．５〜３．０にして、生成物
の酸価が５４ＫＯＨ／９未満とするために１２０〜１８
０℃で加熱することにより得られるのである。(Means for solving the problem to be solved)Currently,
The following was discovered. That is, epoxy resins suitable for obtaining mechanically durable glassy coatings have an acid value of 60 to 60.
Ethylene polyterephthalate with terminal carboxyl groups of 400ItgKOH/9 and epoxy fj60.1
8 to 0.55 mol/100 g of low molecular weight needles or medium molecular weight epoxy resin are added with a catalyst to adjust the molar ratio of carboxyl groups to epoxy groups to 1.5 to 3.0 to increase the acid value of the product. 120 to 18 to make it less than 54KOH/9
It can be obtained by heating at 0°C.
開始成分として、二つの方法のうちの一つにより高分子
量エチレンポリテレフタレートから得られる、カルボキ
シル基を有するニブ・レンボリテレフタレートを用いた
。As starting component, carboxyl-containing nib lemboriterephthalate obtained from high molecular weight ethylene polyterephthalate by one of two methods was used.
これらの方法のうちの一つは、高分子かエチレンボリテ
レフタレ−１・を、ジカルボン酸、特にアジピン酸、セ
バシン酸あるいはイソフタル酸と加熱することからなる
。One of these methods consists of heating the polymer ethylene boriterephthalate-1 with a dicarboxylic acid, especially adipic acid, sebacic acid or isophthalic acid.
もう一つの方法に従えば、高分子量エチレンポリテレフ
タレートをグリコールとともに加熱し、次に得られたエ
チレンオリゴテレフタレ−１−をジカルボン酸環状無水
物、特にコハク酸、テトラハイドロフタル酸、ヘキサハ
イドロフタル酸、マレイン酸、あるいはフタル酸の無水
物とともに加熱する。According to another method, high molecular weight ethylene polyterephthalate is heated with glycol and then the resulting ethylene oligoterephthalate is treated with a dicarboxylic acid cyclic anhydride, especially succinic acid, tetrahydrophthalic acid, hexahydrophthalic acid, etc. Heat with acid, maleic or phthalic anhydride.
また、これとは異なった方法で得られる末端カルボキシ
ル基を有するエチレンポリテレフタレートを使用するこ
とも可能である。その、異なった方法とは、低分子針の
出発物質から得る方法であり、例えば、ジメチルテレフ
タレートをｔル過剰のグリコールとともに加熱し、そし
て次にジカルボン酸あるいはジカルボン無水物と加熱す
る方法である。It is also possible to use ethylene polyterephthalate having terminal carboxyl groups obtained by a different method. A different method is to obtain small molecular needle starting materials, such as heating dimethyl terephthalate with an excess of glycol and then heating with a dicarboxylic acid or dicarboxylic anhydride.
末端カルボキシル基を右するエチレンポリテレフタレー
トをエポキシ樹脂とともに加熱している間に、カルボキ
シル基の反応が実際に完了するまで、エステル結合と第
二アルコールの形成を伴なって、カルボキシル基がエポ
キシ基に付加するのがＩｉ！２３１１された。While heating the ethylene polyterephthalate with the terminal carboxyl groups together with the epoxy resin, the carboxyl groups convert into epoxy groups with the formation of an ester bond and a secondary alcohol until the reaction of the carboxyl groups is actually completed. Ii to add! 2311 was done.
過剰のエポキシ基は未反応のまま残り、こうして１９だ
生成物はエポキシ樹脂型のものであり、典型的なエポキ
シ樹脂硬化剤によって硬化させることができる。Excess epoxy groups remain unreacted and thus the product is of the epoxy resin type and can be cured by typical epoxy resin curing agents.
本発明に従う方法において、有利には、カルボキシル基
とエポキシ基の反応の触媒を使用し、特に塩化リチウム
、第三アミン、テトラアルキルアンモニウムあるいは塩
化ベンジルトリアルキルアンモニウムが好ましい。In the process according to the invention, catalysts for the reaction of carboxyl groups with epoxy groups are advantageously used, in particular lithium chloride, tertiary amines, tetraalkylammonium or benzyltrialkylammonium chloride.
例１． 重量比が４８：５２の高分子量エチレンポリテ
レフタレートとイソフタル酸を、２６０℃で加熱し、酸
価が１７５１１！ＦＫＯＨ／ｇの生成物を１ｑた。次に
、得られた末端カルボキシル基を有するエチレンポリプ
レフタレート１００ｇを、エポキシ１ｌＩｉｏ、２５モ
ル／１００ｇのジアンエポキシ樹脂エビジアン２ （Ｅ
ｐｉｄｉａｎ ２ ＞ ２５０ｇと共に０．１ｇのベン
ジルジメチルアミンを添加して加熱した。酸価が１．５
ｓｙＫＯＨ／ｇ、エポキシ価が０．１０モル／１００ｇ
および軟化点が１２５℃のエポキシ樹脂が得られるまで
１６０℃で加熱した。Example 1. High molecular weight ethylene polyterephthalate and isophthalic acid in a weight ratio of 48:52 were heated at 260°C, and the acid value was 17,511! 1 q of FKOH/g product was obtained. Next, 100 g of the obtained ethylene polyprephthalate having a terminal carboxyl group was mixed with epoxy 1lIio, 25 mol/100 g of diane epoxy resin Evidian 2 (E
Added 0.1 g of benzyldimethylamine along with pidian 2 > 250 g and heated. Acid value is 1.5
syKOH/g, epoxy value is 0.10 mol/100g
and heated at 160°C until an epoxy resin with a softening point of 125°C was obtained.
例２．゛ ２３５℃において、高分子ｆｌｌチレンボリ
テレフタレート１０００ｇとジエヂレングリコール１７
５ｇを加熱し、均一な・液体を得た。次に、温度を２０
０℃にまで下げ、１６２ｇの無水マレイン酸を添加し、
そしてＷＩ価が９６１ＲｇＫＯｌ−１／Ｊとなるまで全
体をこの温度で加熱した。温度を１４０℃に下げた襖、
塩化リチウムｏ、ｏｉｇおよびエポキシ価０．５モル／
１００９のエポキシ樹１１１１ｔ’シアン５ （Ｅｐｉ
ｄｉａｎ ５ ）の８７５ｇを加え、次に、酸価２．３
＃Ｉ！ＦＫＯＨ／ｇ、エポキシ価０．１０モルフ１００
ｇおよび軟化魚８７℃のエポキシ樹脂が冑られるまで仝
休をこの温度で加熱した。Example 2.゛ At 235°C, 1000 g of polymeric full ethylene polyterephthalate and 17 dielene glycol
5g was heated to obtain a homogeneous liquid. Next, increase the temperature to 20
The temperature was lowered to 0°C and 162g of maleic anhydride was added.
The whole was then heated at this temperature until the WI value became 961 RgKOl-1/J. Fusuma with a temperature lowered to 140℃,
Lithium chloride o, oig and epoxy value 0.5 mol/
1009 Epoxy Tree 1111t'Cyan 5 (Epi
dian 5) was added, and then the acid value was 2.3.
#I! FKOH/g, epoxy value 0.10 morph 100
The mixture was heated at this temperature until the epoxy resin at 87°C was melted.
Claims (4)
分子量あるいは中分子量のエポキシ樹脂とともに加熱す
ることからなる固体エポキシ樹脂製造方法において、酸
価６０〜４００ｍｇＫＯＨ／ｇの末端カルボキシル基を
有するエチレンポリテレフタレートとエポキシ価０．１
３〜０．５５モル／１００ｇのジアンエポキシ樹脂とを
、可能であれば、触媒、特に塩化リチウム、第三アミン
、テトラアルキルアンモニウムまたは塩化ベンジルトリ
アルキルアンモニウムの存在下で生成物の酸価が５ｍｇ
ＫＯＨ／ｇ未満になるまで１２０〜１８０℃で加熱する
ことを特徴とする、前記方法。(1) A method for producing a solid epoxy resin comprising heating a dicarboxylic acid with a molar excess of a low or medium molecular weight epoxy resin in the presence of a catalyst, which has a terminal carboxyl group with an acid value of 60 to 400 mgKOH/g. Ethylene polyterephthalate and epoxy value 0.1
3 to 0.55 mol/100 g of diane epoxy resin, if possible in the presence of a catalyst, in particular lithium chloride, tertiary amine, tetraalkylammonium or benzyltrialkylammonium chloride, so that the acid number of the product is 5 mg.
The method described above, characterized in that it is heated at 120-180°C until it becomes less than KOH/g.
ルのエポキシ基を使用する、請求項（１）に記載の方法
。(2) The method according to claim (1), wherein 1.5 to 3.0 moles of epoxy group are used per mole of carboxyl group.
タレートとして、高分子量エチレンポリテレフタレート
とジカルボン酸、特にアジピン酸、セバシン酸あるいは
イソフタル酸とを加熱して得られる生成物を使用する、
請求項（１）または（２）に記載の方法。(3) As ethylene polyterephthalate having terminal carboxyl groups, a product obtained by heating high molecular weight ethylene polyterephthalate and a dicarboxylic acid, in particular adipic acid, sebacic acid or isophthalic acid, is used;
The method according to claim (1) or (2).
タレートとして、高分子量エレチンポリテレフタレート
とグリコールを加熱して得られるエチレンオリゴテレフ
タレートとジカルボン酸の環状無水物、特に、コハク酸
無水物、テトラヒドロフタル酸無水物、ヘキサヒドロフ
タル酸無水物、マレイン酸無水物、あるいはフタル酸無
水物とを加熱して得られる生成物を使用する、請求項（
１）または（２）に記載の方法。(4) As ethylene polyterephthalate having a terminal carboxyl group, ethylene oligoterephthalate obtained by heating high molecular weight elechin polyterephthalate and glycol and a cyclic anhydride of dicarboxylic acid, especially succinic anhydride and tetrahydrophthalic anhydride , hexahydrophthalic anhydride, maleic anhydride, or phthalic anhydride.
The method described in 1) or (2).
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL270298 | 1988-01-26 | ||
| PL1988270298A PL155390B1 (en) | 1988-01-26 | 1988-01-26 | Method of obtaining solid epoxy resins |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH023413A true JPH023413A (en) | 1990-01-09 |
Family
ID=20040305
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1016079A Pending JPH023413A (en) | 1988-01-26 | 1989-01-25 | Production of solid epoxy resin |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPH023413A (en) |
| DE (1) | DE3902311A1 (en) |
| IT (1) | IT1229497B (en) |
| NL (1) | NL8900174A (en) |
| PL (1) | PL155390B1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02274717A (en) * | 1989-03-13 | 1990-11-08 | General Electric Co <Ge> | Manufacture of polyester/polyepoxide composition having high melt viscosity |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CZ2021507A3 (en) * | 2021-11-04 | 2023-05-17 | Synpo, A.S. | Epoxy resins |
-
1988
- 1988-01-26 PL PL1988270298A patent/PL155390B1/en unknown
-
1989
- 1989-01-23 IT IT8919142A patent/IT1229497B/en active
- 1989-01-25 JP JP1016079A patent/JPH023413A/en active Pending
- 1989-01-25 NL NL8900174A patent/NL8900174A/en not_active Application Discontinuation
- 1989-01-26 DE DE3902311A patent/DE3902311A1/en not_active Withdrawn
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02274717A (en) * | 1989-03-13 | 1990-11-08 | General Electric Co <Ge> | Manufacture of polyester/polyepoxide composition having high melt viscosity |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3902311A1 (en) | 1989-08-03 |
| IT1229497B (en) | 1991-09-03 |
| NL8900174A (en) | 1989-08-16 |
| IT8919142A0 (en) | 1989-01-23 |
| PL270298A1 (en) | 1989-08-07 |
| PL155390B1 (en) | 1991-11-29 |
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