JP3837574B2 - Clay molding production method and clay molding composition - Google Patents
Clay molding production method and clay molding composition Download PDFInfo
- Publication number
- JP3837574B2 JP3837574B2 JP2004095750A JP2004095750A JP3837574B2 JP 3837574 B2 JP3837574 B2 JP 3837574B2 JP 2004095750 A JP2004095750 A JP 2004095750A JP 2004095750 A JP2004095750 A JP 2004095750A JP 3837574 B2 JP3837574 B2 JP 3837574B2
- Authority
- JP
- Japan
- Prior art keywords
- clay
- carboxyl group
- epoxy compound
- group
- lignin
- 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 - Lifetime
Links
- 239000004927 clay Substances 0.000 title claims description 36
- 239000000203 mixture Substances 0.000 title claims description 36
- 238000000465 moulding Methods 0.000 title claims description 12
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 50
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 48
- 229920005610 lignin Polymers 0.000 claims description 30
- 239000004593 Epoxy Substances 0.000 claims description 25
- -1 saccharide compounds Chemical class 0.000 claims description 25
- 239000000126 substance Substances 0.000 claims description 23
- 125000001931 aliphatic group Chemical group 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 12
- 150000005846 sugar alcohols Polymers 0.000 claims description 11
- 239000007809 chemical reaction catalyst Substances 0.000 claims description 8
- 230000003796 beauty Effects 0.000 claims description 5
- 238000005507 spraying Methods 0.000 claims description 2
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- 239000000047 product Substances 0.000 description 33
- 239000000243 solution Substances 0.000 description 24
- 239000003822 epoxy resin Substances 0.000 description 23
- 229920000647 polyepoxide Polymers 0.000 description 23
- 229920005862 polyol Polymers 0.000 description 19
- 150000003077 polyols Chemical class 0.000 description 18
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 17
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 16
- 239000003054 catalyst Substances 0.000 description 15
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- 238000005886 esterification reaction Methods 0.000 description 12
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- 238000002329 infrared spectrum Methods 0.000 description 4
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Description
本発明は粘土成形物の製造方法及び粘土成型用組成物に関するものである。 The present invention relates to a method for producing a clay molded product and a composition for clay molding.
粘土は可塑性や粘着性を有することから、成形用材料として広く用いられている。この粘土を用いて成形物を得る方法としては、粘土に水を加えてペースト状とし、これを所定の形状に成形した後、乾燥硬化する方法が用いられている。
しかし、このような方法では、その成型後の乾燥硬化に時間がかる上に、成形物の強度が不十分である等の問題を有した。
Clay is widely used as a molding material because it has plasticity and adhesiveness. As a method for obtaining a molded product using this clay, a method is used in which water is added to clay to form a paste, which is molded into a predetermined shape and then dried and cured.
However, such a method has problems such as long time for drying and curing after the molding and insufficient strength of the molded product.
本発明は、形成後の乾燥硬化が容易でかつ成形物強度にすぐれた粘土成形物の製造方法及び粘土成形用組成物を提供することをその課題とする。 It is an object of the present invention to provide a method for producing a clay molded product that is easy to dry and harden after formation and has excellent molded product strength, and a composition for clay molding.
本発明によれば、以下に示す方法及び組成物が提供される。 According to the present invention, the following methods and compositions are provided.
（１）（ｉ）カルボキシル基含有糖化合物及び／又はカルボキシル基含有リグニン物質、（ii）多価エポキシ化合物、（iii）多価アルコール及び（iv）粘土からなり、該粘土を少なくとも４０重量％含有する混合物を成形した後、該成形物表面に該エポキシ化合物硬化反応用触媒溶液をスプレーすることを特徴とする粘土成形物の製造方法。
（２）（ｉ）カルボキシル基含有糖化合物及び／又はカルボキシル基含有リグニン物質、（ii）多価エポキシ化合物、（iii）該エポキシ化合物硬化反応用触媒、（iv）多価アルコール及び（v）粘土からなり、該粘土を少なくとも４０重量％含有する混合物を成形し、硬化させることを特徴とする粘土成形物の製造方法。
（３）該多価エポキシ化合物が、脂肪族系エポキシ化合物である（１）又は（２）に記載の方法。
（４）（ｉ）カルボキシル基含有糖化合物及び／又はカルボキシル基含有リグニン物質、（ii）多価エポキシ化合物、（iii）該エポキシ化合物硬化反応用触媒、（iv）多価アルコール及び（v）粘土からなることを特徴とする粘土成形用組成物。
（５）該多価エポキシ化合物が、脂肪族系エポキシ化合物である（４）に記載の組成物。
(1) (i) carboxyl group-containing saccharide compounds Mono及 beauty / or carboxyl group-containing lignin substance, (ii) a polyvalent epoxy compound, consists (iii) polyhydric alcohol and (iv) clay, at least a clay A method for producing a clay molded article, comprising molding a mixture containing 40% by weight and then spraying the catalyst solution for curing the epoxy compound on the surface of the molded article.
(2) (i) carboxyl group-containing saccharide compounds Mono及 beauty / or carboxyl group-containing lignin substance, (ii) a polyvalent epoxy compound, (iii) the epoxy compound curing reaction catalyst, (iv) a polyhydric alcohol and ( v) A method for producing a clay molded product comprising molding a clay comprising at least 40% by weight and curing the mixture.
(3) The method according to (1) or (2), wherein the polyvalent epoxy compound is an aliphatic epoxy compound.
(4) (i) carboxyl group-containing saccharide compounds and / or carboxyl group-containing lignin substance, (ii) a polyvalent epoxy compound, (iii) the epoxy compound curing reaction catalyst, (iv) a polyhydric alcohol and ( v) A clay molding composition comprising clay.
(5) The composition according to (4), wherein the polyvalent epoxy compound is an aliphatic epoxy compound.
本発明によれば、強度にすぐれた粘土成形物を容易かつ効率よく製造することができる。しかも、本発明の粘土成形物は、生分解性にすぐれた糖化合物及び／又はリグニン物質を含むことから、自然環境に廃棄したときに崩壊を生じるものである。 According to the present invention, it is possible to easily and efficiently produce a clay molded article having excellent strength. Moreover, since the clay molded article of the present invention contains a sugar compound and / or lignin substance excellent in biodegradability, it will collapse when discarded in the natural environment.
本発明で用いるカルボキシル基含有糖化合物において、該糖化合物としては、従来公知の各種の可溶性のものが用いられる。このようなものには、単糖、少糖、多糖、糖アルコール等が包含され、ポリオールに可溶性のものであれば任意のものが用いられる。このような糖化合物には、例えば、糖蜜、廃糖蜜、グルコース、ガラクトース、キシロース、乳糖、マンノース、タロース、ラムノース、アラビノース、グルコシルマンノース、リキソース、アロース、アルトロース、グロース、イドース、リボース、エリトロース、トレオース、プシコース、フルクトース、ソルボース、タガトース、ペンツロース、テトロース、スクロース、マルトース、イソマルトース、セロビオース、ラクトース、トレハロース、コウジビオース、ソホロース、ニゲロース、ラミナリビオース、イソマルトース、ゲンチオビオース、メリビオース、ブランテオビオース、ツラノース、ビシアノース、アガロビオース、シラビオース、ルチノース、プリメプロース、キシロビオース、ロジメナビオース、エリトリトール、メソエリトリトール、マルチトール、ラクチトール、Ｄ−トレイトール、Ｄ−アラビニトール、リビトール、キシリトール、ソルビトール、ガラクチトール、Ｄ−マンニトール、アリトール、高級アルジトール等の他、デンプン、デキストラン、マンナン、ペクチン、ペクチン酸、アルギン酸、キトサン等が挙げられる。 In the carboxyl group-containing sugar compound used in the present onset bright, as the sugar compound, conventionally known various soluble it is used. Such substances include monosaccharides, oligosaccharides, polysaccharides, sugar alcohols, and the like, and any are usable as long as they are soluble in polyol. Such sugar compounds include, for example, molasses, molasses, glucose, galactose, xylose, lactose, mannose, talose, rhamnose, arabinose, glucosyl mannose, lyxose, allose, altrose, gulose, idose, ribose, erythrose, threose , Psicose, fructose, sorbose, tagatose, pentulose, tetrose, sucrose, maltose, isomaltose, cellobiose, lactose, trehalose, kojibiose, sophorose, nigerose, laminaribiose, isomaltose, gentiobiose, melibiose, blanteobiose, Vicianose, agarobiose, sylabiose, rutinose, primeproose, xylobiose, rosigenaviose, erythritol Mesoerythritol, maltitol, lactitol, D-threitol, D-arabinitol, ribitol, xylitol, sorbitol, galactitol, D-mannitol, allitol, higher alditol, etc., starch, dextran, mannan, pectin, pectic acid, alginic acid , Chitosan and the like.
本発明で用いるカルボキシル基含有リグニン物質において、該リグニン物質には、リグニン及びその変性体が包含される。このリグニン物質は、木材や竹、ワラ等から分離されたもので、フェニルプロパンを骨格とする構成単位体が縮合して形成された分子量が８００〜１００００の重合体であり、従来公知の物質である。このものは、通常、粉体状で取扱われている。 In the carboxyl group-containing lignin substance used in the present invention, the lignin substance includes lignin and modified products thereof. This lignin substance is a polymer having a molecular weight of 800 to 10,000 formed by condensation of structural units having phenylpropane as a skeleton, separated from wood, bamboo, straw, etc., and is a conventionally known substance. is there. The thing is, usually, are'll handling in powder form.
本発明においては、前記カルボキシル基を含有する糖化合物及びリグニン物質（以下、これらを単にカルボキシル基含有物とも言う）は、多価アルコール（ポリオール）に溶解させて溶液状で用いられる。本発明で用いるポリオールは分子中にヒドロキシル基を少なくとも２つ含有する液状化合物であり、このようなものとしては、例えば、エチレングレコール、ジニチレングリコール、１．４−ブタンジオール、１．６−ヘキサンジオール、ネオベンチルグリコール、トリメチロールブロパン、グリセリン、トリエタノールアミン、ソルビトール等の低分子量ポリオール：ポリエチレングリコール、ポリプロピレングリコール、ポリテトラメチレングリコール、エチレンオキシド／プロピレンオキシド共重合体等のポリエーテルポリオール：ポリカプロラクトン、ポリ−β−メチル−δ−プチロラクトン、ジオールと二塩基酸からのポリエステル等が挙げられる。その他、水酸基含有液状ポリブタジエン、ポリカーボネートジオール、アクリルポリオール等が挙げられる。 In the present invention, the saccharide compound containing carboxy group and the lignin substance (hereinafter also simply referred to as carboxy group-containing product) are dissolved in a polyhydric alcohol (polyol) and used in the form of a solution. The polyol used in the present invention is a liquid compound containing at least two hydroxyl groups in the molecule, and examples thereof include ethylene glycol, diethylene glycol, 1.4-butanediol, 1.6- Low molecular weight polyols such as hexanediol, neoventyl glycol, trimethylol bropan, glycerin, triethanolamine, sorbitol: polyether polyols such as polyethylene glycol, polypropylene glycol, polytetramethylene glycol, ethylene oxide / propylene oxide copolymer: Examples include polycaprolactone, poly-β-methyl-δ-ptyrolactone, polyesters from diols and dibasic acids, and the like. Other examples include hydroxyl group-containing liquid polybutadiene, polycarbonate diol, and acrylic polyol.
本発明で用いる多価エポキシ化合物は、分子中に少なくとも２つのエポキシ基を有するものであり、エポキシ樹脂として用いられているものを一般的に用いることができる。このようなエポキシ化合物としては、常温で固体状又は液体状を示す従来公知の各種のものが用いられる。このようなものとしては、例えば、アルキレングリコール型エポキシ樹脂、ビスフェノールＡ型エポキシ樹脂、ビスフェノールＦ型エポキシ樹脂等のジグリシジルエーテル型エポキシ樹脂；フェノールノボラック型エポキシ樹脂、クレゾールノボラック型エポキシ樹脂等のノボラック型エポキシ樹脂；グリシジルエステル型エポキシ樹脂；グリシジルアミン型エポキシ樹脂；線状脂肪族型エポキシ樹脂；油脂変性エポキシ樹脂；複素環型エポキシ樹脂等があげられる。
本発明においては、生分解性の点から、その骨格構造が脂肪族構造のもの（アルキレン基やアルケニレン基等を有するもの）の使用が好ましい。このような脂肪族系エポキシ樹脂としては、アルキレングリコール型エポキシ樹脂、脂肪族系グリシジルエーテル型エポキシ樹脂、脂肪族系グリシジルエステル型エポキシ樹脂、脂肪族系グリシジルアミン型エポキシ樹脂、脂肪族系油脂変性エポキシ樹脂等が挙げられる。
The polyvalent epoxy compound used in the present invention has at least two epoxy groups in the molecule, and those used as epoxy resins can be generally used. As such an epoxy compound, various conventionally known compounds that are solid or liquid at room temperature are used. Examples of such a resin include diglycidyl ether type epoxy resins such as alkylene glycol type epoxy resins, bisphenol A type epoxy resins, and bisphenol F type epoxy resins; novolak types such as phenol novolac type epoxy resins and cresol novolak type epoxy resins. Examples thereof include epoxy resins; glycidyl ester type epoxy resins; glycidyl amine type epoxy resins; linear aliphatic type epoxy resins;
In the present invention, in view of biodegradability, it is preferable to use an aliphatic structure (having an alkylene group, an alkenylene group or the like). Examples of such aliphatic epoxy resins include alkylene glycol type epoxy resins, aliphatic glycidyl ether type epoxy resins, aliphatic glycidyl ester type epoxy resins, aliphatic glycidyl amine type epoxy resins, and aliphatic oil-modified epoxy resins. Examples thereof include resins.
カルボキシル基含有糖化合物及び／又はリグニン化合物は、糖化合物及び／又リグニン化合物にカルボキシル基を導入することによって製造される。この場合のカルボキシル基導入方法としては、糖化合物又はリグニン物質のヒドロキシ（ＯＨ）基に対し、多価カルボン酸無水物をエステル化反応させる方法（特開２００２−２８４７９１）を用いることができる。 Carboxyl group-containing saccharide compounds and / or lignin compounds are prepared by introducing a carboxyl group into the sugar compound and / or lignin compounds. As a method for introducing a carboxyl group in this case, a method of subjecting a hydroxy (OH) group of a sugar compound or a lignin substance to an esterification reaction with a polyvalent carboxylic acid anhydride (Japanese Patent Laid-Open No. 2002-284791) can be used.
前記多価カルボン酸無水物には、２〜６価、好ましくは２〜４価のカルボン酸無水物が包含されるが、好ましくは２価カルボン酸無水物が用いられる。このような多価カルボン酸無水物は、従来公知の物質であり、例えば、次の一般式（１）で表わすことができる。
本発明においては、生分解性の点から、脂肪族系多価カルボン酸無水物の使用が好ましい。
The polyvalent carboxylic acid anhydride includes divalent to hexavalent, preferably divalent to tetravalent carboxylic acid anhydrides, and divalent carboxylic acid anhydrides are preferably used. Such a polyvalent carboxylic acid anhydride is a conventionally known substance and can be represented by, for example, the following general formula (1).
In the present invention, it is preferable to use an aliphatic polycarboxylic acid anhydride from the viewpoint of biodegradability.
糖化合物又はリグニン物質にカルボキシル基を導入するための第１の方法では、先ず、糖化合物及／又はリグニン物質（以下糖化合物等とも言う）とポリオールとを混合し、糖化合物及び／又はリグニン物質を溶解状で含むポリオール溶液を調製する。この場合、糖化合物等の使用割合は、ポリオール１重量部に対して０．１〜１０重量部、好ましくは０．５〜５重量部の割合である。糖化合物等の使用割合が多すぎると、ポリオールに均一に溶解させるのが困難になり、均一なポリオール溶液が得られなくなる。 In the first method for introducing a carboxyl group into a sugar compound or lignin substance, first, the sugar compound and / or lignin substance (hereinafter also referred to as sugar compound or the like) and a polyol are mixed, and the sugar compound and / or lignin substance are mixed. Is prepared in a dissolved state. In this case, the ratio of the sugar compound used is 0.1 to 10 parts by weight, preferably 0.5 to 5 parts by weight, based on 1 part by weight of the polyol. When the ratio of the sugar compound or the like is too large, it becomes difficult to uniformly dissolve in the polyol, and a uniform polyol solution cannot be obtained.
次に、前記糖化合物等を溶解状態で含むポリオール溶液に多価カルボン酸無水物を混合し、エステル化反応させる。この場合、反応混合物中に触媒を存在させることが好ましい。この場合の触媒としては、従来公知のエステル化反応触媒を用いることができる。反応温度は３０〜１５０℃、好ましくは５０〜１００℃であり、反応応力は、常圧又は減圧が採用される。 Next, a polyvalent carboxylic acid anhydride is mixed with a polyol solution containing the sugar compound and the like in a dissolved state, and an esterification reaction is performed. In this case, it is preferred that a catalyst is present in the reaction mixture. As the catalyst in this case, a conventionally known esterification reaction catalyst can be used. The reaction temperature is 30 to 150 ° C., preferably 50 to 100 ° C., and normal pressure or reduced pressure is adopted as the reaction stress.
前記糖化合物等に対する多価カルボン酸無水物のエステル化反応は、次式で表わすことができる。
前記反応式からわかるように、ポリオール溶液に含まれるヒドロキシル基（即ち、糖化合物等に含まれるヒドロキシル基とポリオールに含まれるヒドロキシル基を合計した量のヒドロキシル基）１モルに対して、多価カルボン酸無水物１モルが反応するときには、遊離カルボキシル基（−ＣＯＯＨ）１モルを含有するエステル化反応生成物が得られる。反応生成物中に含まれる遊離カルボキシル基の割合は、使用する多価カルボン酸無水物の量で調節することができる。本発明の場合、多価カルボン酸無水物の使用割合は、ポリオール溶液中に含まれる全遊離ヒドロキシル基（−ＯＨ基）の当量数に対して、１つのカルボン酸無水物基を２当量と換算して、１．６〜４倍当量、好ましくは２〜３倍当量である。エステル化反応生成物は、常温において液状又は固体状のものである。 As can be seen from the above reaction formula, the polyvalent carboxylic acid is contained in 1 mol of the hydroxyl group contained in the polyol solution (that is, the total amount of hydroxyl groups contained in the sugar compound and the hydroxyl group contained in the polyol). When 1 mole of acid anhydride is reacted, an esterification reaction product containing 1 mole of free carboxyl group (—COOH) is obtained. The ratio of the free carboxyl group contained in the reaction product can be adjusted by the amount of polyvalent carboxylic anhydride used. In the case of the present invention, the usage ratio of the polyvalent carboxylic acid anhydride is calculated by converting one carboxylic acid anhydride group to 2 equivalents with respect to the equivalent number of all free hydroxyl groups (—OH groups) contained in the polyol solution. Then, it is 1.6 to 4 times equivalent, preferably 2 to 3 times equivalent. The esterification reaction product is liquid or solid at normal temperature.
カルボキシル基含有糖化合物及び／又はリグニン物質を製造する第２の方法では、先ず、糖化合物及び／又はリグニン物質とポリオールとを混合し、糖化合物等を溶解状態で含有するポリオール溶液を作る。この場合、糖化合物等の使用割合は、ポリオール１重量部に対して０．１〜１０重量部、好ましくは０．５〜５重量部の割合である。 In the second method of producing the carboxyl group-containing sugar compound and / or lignin material, firstly, a sugar compound and / or mixing the lignin material and the polyol to produce a polyol solution containing a sugar compound such as in solution. In this case, the ratio of the sugar compound used is 0.1 to 10 parts by weight, preferably 0.5 to 5 parts by weight, based on 1 part by weight of the polyol.
次に、前記のようにして得られた混合物に、多価カルボン酸無水物を添加混合し、エステル化反応を行わせる。反応温度は、３０〜１５０℃、好ましくは５０〜１００℃であり、圧力は常圧又は減圧が採用される。多価カルボン酸無水物の使用割合は、ポリオール、糖化合物等に含まれる全ヒドロキシル基の当量数に対し、その多価カルボン酸無水物のカルボキシル基当量数で、１．６〜４倍当量、好ましくは２〜３倍当量である。 Next, a polycarboxylic acid anhydride is added and mixed to the mixture obtained as described above, and an esterification reaction is performed. The reaction temperature is 30 to 150 ° C., preferably 50 to 100 ° C., and normal pressure or reduced pressure is adopted as the pressure. The use ratio of the polyvalent carboxylic acid anhydride is 1.6 to 4 times the equivalent number of carboxyl group equivalents of the polyvalent carboxylic acid anhydride, with respect to the equivalent number of all hydroxyl groups contained in the polyol, sugar compound, etc. Preferably it is 2-3 times equivalent.
このようにして得られるエステル化反応生成物は、遊離カルボキシル基を含む固体状又は固液混合物である。反応性生物中に含まれる遊離カルボキシル基の割合は、使用する多価カルボン酸無水物の量で調節することができる。本発明の場合、多価カルボン酸無水物の使用割合は、反応原料中に含まれる全遊離ヒドロキシル基（−ＯＨ基）の当量数に対して、１つのカルボン酸無水物基を２当量と換算して、１．６〜４倍当量、好ましくは２〜３倍当量である。エステル化反応生成物は、常温において液状又は固体状のものである。 The esterification reaction product thus obtained is a solid or solid-liquid mixture containing a free carboxyl group. The ratio of the free carboxyl group contained in the reactive organism can be adjusted by the amount of polyvalent carboxylic anhydride used. In the case of the present invention, the usage ratio of the polyvalent carboxylic acid anhydride is calculated by converting one carboxylic acid anhydride group to 2 equivalents with respect to the equivalent number of all free hydroxyl groups (—OH groups) contained in the reaction raw material. Then, it is 1.6 to 4 times equivalent, preferably 2 to 3 times equivalent. The esterification reaction product is liquid or solid at normal temperature.
カルボキシル基含リグニン物質は、リグニンを軽度に酸化することによっても得ることができる。このようなリグニンの酸化方法は公知のものである。 Carboxyl group-containing lignin material may also be obtained by oxidizing lightly lignin. Such lignin oxidation methods are known.
本発明による前記糖化合物及びリグニン物質は、その分子中に生分解性生成分を含有し、生分解性にすぐれたものであり、生分解性反応原料として各種の用途に適用することができる。 The sugar compounds and lignin substances according to the invention contains a biodegradable product fraction in the molecule, which has excellent biodegradability, it can be applied to various applications as a biodegradable reactants .
前記した多価エポキシ化合物とカルボキシル基を含有物からなる組成物（エポキシ樹脂組成物）には、必要に応じ、各種の補助成分、例えば、硬化促進剤、充填剤、着色剤、難燃剤、離型剤等を配合することができる。硬化促進剤としては、慣用のもの、例えば、イミダゾール化合物、ジアザビシクロウンデセン及びそのフェノール塩、トリフェニルホスフィン、三級アミン、アミンアダクト潜在性硬化促進剤、ジシアンジアミド等が用いられる。充填剤としては、アルミナ、シリカ、マグネシア、三酸化アンチモン、炭酸マグネシウム、炭酸カルシウム、マイカ、クレイなどが挙げられる。 In the composition comprising the polyvalent epoxy compound and the carboxyl group (epoxy resin composition), various auxiliary components, for example, a curing accelerator, a filler, a colorant, a flame retardant, a release agent are used as necessary. Molding agents and the like can be blended. As a hardening accelerator, a conventional thing, for example, an imidazole compound, diazabicycloundecene and its phenol salt, a triphenylphosphine, a tertiary amine, an amine adduct latent hardening accelerator, dicyandiamide, etc. are used. Examples of the filler include alumina, silica, magnesia, antimony trioxide, magnesium carbonate, calcium carbonate, mica, and clay.
エポキシ樹脂組成物におけるカルボキシル基含有物の配合量は、そのエポキシ樹脂のエポキシ基当量数の０．８〜２倍当量、好ましくは１〜１．５倍当量である。 The compounding quantity of the carboxyl group-containing material in the epoxy resin composition is 0.8 to 2 times equivalent, preferably 1 to 1.5 times equivalent to the number of epoxy group equivalents of the epoxy resin.
前記エポキシ樹脂組成物は、そのカルボキシル基含有物が硬化剤として作用し、これを加熱することにより、カルボキシル基含有物とエポキシ樹脂とが反応し、カルボキシル基含有物を架橋剤とする硬化物を得ることができる。この硬化物は、その構造中に生分解性のカルボキシル基含有物部分を有することから、その部分から生分解性を生じる微生物崩壊性のものである。 In the epoxy resin composition, the carboxyl group-containing product acts as a curing agent, and by heating this, the carboxyl group-containing product reacts with the epoxy resin, and the cured product having the carboxyl group-containing product as a crosslinking agent is obtained. Obtainable. Since this cured product has a biodegradable carboxyl group-containing part in its structure, it is microbially degradable and produces biodegradability from that part.
本発明で用いるエポキシ化合物硬化反応用触媒としては、従来公知のもの、例えば、ジメチルベンジルアミン、ジメチルアニリン、２，４，６−トリス（ジメチルアミノメチル）フェノール、ジエチルベンジルアミン等のアミノ系触媒や２−エチルヘキサン酸すず（II）、ラウリン酸ジブチルすず、２−エチルヘキサン酸チタン（IV）等のすず及びチタン系触媒が用いられる。これらのものは、ポリオール溶液として用いられる。この場合、溶液中の触媒濃度は、０．０５〜５ｗｔ％、好ましくは０．１〜２ｗｔ％である。 Examples of the epoxy compound curing reaction catalyst used in the present invention include conventionally known ones such as amino catalysts such as dimethylbenzylamine, dimethylaniline, 2,4,6-tris (dimethylaminomethyl) phenol, and diethylbenzylamine. Tin and titanium-based catalysts such as tin 2-ethylhexanoate (II), dibutyltin laurate, titanium 2-ethylhexanoate (IV) and the like are used. These are used as a polyol solution. In this case, the catalyst concentration in the solution is 0.05 to 5 wt%, preferably 0.1 to 2 wt%.
本発明における粘土としては、従来公知の各種のもの、例えば、白とう土、カオリン、ベントナイト、木節粘土、ガイロメ粘土、タルク等が挙げられる。 Examples of the clay in the present invention include various conventionally known clays such as white clay, kaolin, bentonite, kibushi clay, gyrome clay, and talc.
本発明により粘土形成物を製造するには、先ず、カルボキシル基含有物、多価エポキシ化合物及び多価アルコールからなる液状のエポキシ樹脂組成物を作り、これに粘土を加え、均一に混練して混練物（混合物）とし、この混練物を人手や金型、押出機等の成形方法を用いて所定形状に形成する。 In order to produce a clay-formed product according to the present invention, first, a liquid epoxy resin composition comprising a carboxyl group-containing material, a polyvalent epoxy compound and a polyhydric alcohol is prepared, and clay is added thereto, and the mixture is uniformly kneaded and kneaded. The kneaded product is formed into a predetermined shape using a molding method such as manual labor, a mold, an extruder, or the like.
粘土の割合は、混練物が成形可能となる量であればよく、全混練物又は成形物中、少なくとも４０重量％、好ましくは５０〜８０重量％である。
溶媒である多価アルコールは、全混練物又は成形物中、５〜３０重量％、好ましくは１０〜２０重量％である。
The proportion of the clay may be an amount that enables the kneaded product to be molded, and is at least 40% by weight, preferably 50 to 80% by weight in the entire kneaded product or molded product.
The polyhydric alcohol as the solvent is 5 to 30% by weight, preferably 10 to 20% by weight, in the entire kneaded product or molded product.
次に、この成形物の表面に触媒溶液を塗布し、室温又は３０〜６０℃の加熱下に保持する。これによって、触媒溶液は成形物の表面から成形物中に浸透してエポキシ樹脂及びカルボキシル基含有物が硬化反応して、硬化した成形物が得られる。
また、本発明においては、エポキシ樹脂硬化反応用触媒は、スプレー溶液に含有される代わりに、液状にエポキシ樹脂組成物に含有させることもできる。
Next, a catalyst solution is apply | coated to the surface of this molded object, and it hold | maintains under room temperature or 30-60 degreeC heating. As a result, the catalyst solution penetrates into the molded product from the surface of the molded product, and the epoxy resin and the carboxyl group-containing product undergo a curing reaction to obtain a cured molded product.
In the present invention, the epoxy resin curing reaction catalyst can be contained in the epoxy resin composition in a liquid form instead of being contained in the spray solution.
成形物の形状は特に制約されず、容器状、中空体状、板状、ブロック状、柱状等の各種の形状であることができる。 The shape of the molded product is not particularly limited, and may be various shapes such as a container shape, a hollow body shape, a plate shape, a block shape, and a column shape.
次に、本発明を実施例によりさらに詳述する。 Next, the present invention will be described in further detail with reference to examples.
参考例１
アシドリシスリグニン０．５ｇを、エチレングリコール１．５５ｇに５０℃で溶解し、これに無水こはく酸６．３ｇおよびジメチルアニリン５滴を加えて８０℃で３時間攪拌した。得られたエステル化生成物（カルボキシル基含有物）（多価カルボン酸生成物）の赤外吸収スペクトルには、１７４０ｃｍ（エステル）および１８００ｃｍ付近（カルボン酸）にピークが認められた。
Reference example 1
0.5 g of acidolysis lignin was dissolved in 1.55 g of ethylene glycol at 50 ° C., 6.3 g of succinic anhydride and 5 drops of dimethylaniline were added thereto, and the mixture was stirred at 80 ° C. for 3 hours. In the infrared absorption spectrum of the obtained esterified product (carboxyl group-containing product) (polyvalent carboxylic acid product), peaks were observed at 1740 cm (ester) and around 1800 cm (carboxylic acid).
参考例２
参考例１において、アシドリシスリグニンのかわりにクラフトリグニンを用いて、同様にして多価カルボン酸を得た。その構造にはエステル基とカルボキシル基が含まれることを、ＩＲスペクトルにて確認した。
Reference example 2
In Reference Example 1, polyvalent carboxylic acid was obtained in the same manner using kraft lignin instead of acidolysis lignin. The IR spectrum confirmed that the structure contained an ester group and a carboxyl group.
参考例３
参考例１において、アシドリシスリグニンのかわりにグルコースを用いて、同様にして多価カルボン酸を得た。その構造にはエステル基とカルボキシル基が含まれることを、ＩＲスベクトルにて確認した。
Reference example 3
In Reference Example 1, polyvalent carboxylic acid was obtained in the same manner using glucose instead of acidolysis lignin. It was confirmed by IR vector that the structure contained an ester group and a carboxyl group.
参考例４
参考例１において、アシドリシスリグニンのかわりに、フルクトースを用いて、同様にして多価カルボン酸を得た。その構造にはエステル基とカルボキシル基が含まれることを、ＩＲスペクトルにて確認した。
Reference example 4
In Reference Example 1, a polyvalent carboxylic acid was obtained in the same manner using fructose instead of acidolysis lignin. The IR spectrum confirmed that the structure contained an ester group and a carboxyl group.
参考例５
参考例１において、アシドリシスリグニンのかわりにスクロースを用いて、同様にして多価カルボン酸を得た。その構造にはエステル基とカルボキシル基が含まれることを、IＲスペクトルにて確認した。
Reference Example 5
In Reference Example 1, a polyvalent carboxylic acid was obtained in the same manner using sucrose instead of acidolysis lignin. The IR spectrum confirmed that the structure contained an ester group and a carboxyl group.
参考例６
参考例１において、アシドリシスリグニンのかわりに糖蜜を用いて、同様にして多価カルボン酸を得た。その構造にはエステル基とカルボキシル基が含まれていることを、ＩＲスペクトルにて確認した。
Reference Example 6
In Reference Example 1, polyvalent carboxylic acid was obtained in the same manner using molasses instead of acidolysis lignin. It was confirmed by IR spectrum that the structure contained an ester group and a carboxyl group.
参考例７
リンターセルロース０．５ｇを水に浸せきさせた後、エチレングリコールで置換して、エチレングリコール１ｇとなるように混合し、これに無水こはく酸４．８ｇおよびジメチルアニリン５滴を加えて８０℃で３時間攪拌した。得られた多価カルボン酸生成物の赤外吸収スペクトルには、１７４０ｃｍ（エステル）および１８００ｃｍ付近（カルボン酸）にピークが認められた。
Reference Example 7
After soaking 0.5 g of lintercellulose in water, it was replaced with ethylene glycol and mixed to 1 g of ethylene glycol. To this was added 4.8 g of succinic anhydride and 5 drops of dimethylaniline, and the mixture was mixed at 80 ° C. Stir for hours. In the infrared absorption spectrum of the obtained polyvalent carboxylic acid product, peaks were observed at 1740 cm (ester) and around 1800 cm (carboxylic acid).
参考例８
参考例７において、リンターセルロースのかわりにデンプンを用い、同様にして多価カルボン酸を得た。
Reference Example 8
In Reference Example 7, starch was used instead of lintercellulose, and a polyvalent carboxylic acid was obtained in the same manner.
参考例９
参考例７において、リンターセルロースのかわりにキチンを用い、同様にして多価カルボン酸を得た。
Reference Example 9
In Reference Example 7, a polyvalent carboxylic acid was obtained in the same manner using chitin instead of lintercellulose.
参考例１０
参考例７において、リンターセルロースのかわりにキトサンを用い、同様にして多価カルボン酸を得た。
Reference Example 10
In Reference Example 7, polyvalent carboxylic acid was obtained in the same manner using chitosan instead of lintercellulose.
参考例１１
参考例７において、リンターセルロースのかわりに木粉を用い、同様にして多価カルボン酸を得た。
Reference Example 11
In Reference Example 7, wood powder was used in place of lintercellulose, and a polyvalent carboxylic acid was obtained in the same manner.
参考例１２
参考例７において、リンターセルロースのかわりにコーヒー豆からを用い、同様にして多価カルボン酸を得た。
Reference Example 12
In Reference Example 7, a polyvalent carboxylic acid was obtained in the same manner using coffee beans instead of lintercellulose.
参考例１３
参考例７において、リンターセルロースのかわりにバガスを用い、同様にして多価カルボン酸を得た。
Reference Example 13
In Reference Example 7, bagasse was used in place of lintercellulose, and a polyvalent carboxylic acid was obtained in the same manner.
実施例１
リグニンスルホン酸塩を軽度に酸化して得られる、カルボキシル基含有リグニンスルホン酸塩１０部をエチレングリコール１０部に溶解し、これにエチレングリコールグリシジルエーテル６．５部を加えて溶液を得た。この溶液に、白とう土５０部を加えてよく混合し、得られた混合物を板状に成形した。この成形体表面にアミン系触媒及びすず系触媒のエチレングリコール溶液を噴霧し、１日室温で放置し板状硬化体を得た。
Example 1
10 parts of a carboxyl group-containing lignin sulfonate obtained by lightly oxidizing lignin sulfonate was dissolved in 10 parts of ethylene glycol, and 6.5 parts of ethylene glycol glycidyl ether was added thereto to obtain a solution. To this solution, 50 parts of white clay was added and mixed well, and the resulting mixture was formed into a plate shape. An amine-based catalyst and an ethylene glycol solution of a tin-based catalyst were sprayed on the surface of the molded body, and left at room temperature for 1 day to obtain a plate-shaped cured body.
実施例２
リグニンスルホン酸塩を軽度に酸化して得られる、カルボキシル基含有リグニンスルホン酸塩１０部をエチレングリコール１０部に溶解し、これにエチレングリコールグリシジルエーテル６．５部を加えて溶液を得た。この溶液に、白とう土５０部及びアミン系触媒及びすず系触媒０．１部を加えてよく混合し、得られた混合物を板状に成形した。１日室温で放置し板状硬化体を得た。
Example 2
10 parts of a carboxyl group-containing lignin sulfonate obtained by lightly oxidizing lignin sulfonate was dissolved in 10 parts of ethylene glycol, and 6.5 parts of ethylene glycol glycidyl ether was added thereto to obtain a solution. To this solution, 50 parts of white clay and 0.1 part of amine-based catalyst and tin-based catalyst were added and mixed well, and the resulting mixture was formed into a plate shape. The plate-like cured body was obtained by leaving it at room temperature for 1 day.
実施例３
グルコース１０部及びエチレングリコール１０部の水酸基を無水コハク酸と反応させてエステルカルボン酸化した誘導体混合物を得た。この誘導体混合物１０部をエチレングリコール１０部に溶解し、これにエチレングリコールグリシジルエーテル１０部を加えて溶液を得た。この溶液に、白とう土５０部及びアミン系触媒及びすず系触媒０．１部を加えてよく混合し、得られた混合物を板状に成形し、１日室温で放置し板状硬化体を得た。
Example 3
A derivative mixture obtained by reacting 10 parts of glucose and 10 parts of ethylene glycol with succinic anhydride to undergo ester carboxyl oxidation was obtained. 10 parts of this derivative mixture was dissolved in 10 parts of ethylene glycol, and 10 parts of ethylene glycol glycidyl ether was added thereto to obtain a solution. To this solution, 50 parts of white clay and 0.1 part of an amine catalyst and tin catalyst are added and mixed well. The resulting mixture is formed into a plate shape and allowed to stand at room temperature for one day. Obtained.
実施例４
廃糖蜜１０部及びエチレングリコール１０部の水酸基を無水コハク酸と反応させてエステルカルボン酸化した誘導体混合物を得た。この誘導体混合物１０部をエチレングリコール１０部に溶解し、これにエチレングリコールグリシジルエーテル１０部を加えて溶液を得た。この溶液に、白とう土５０部及びアミン系触媒及びすず系触媒０．１部を加えてよく混合し、得られた混合物を板状に成形し、１日室温で放置し板状硬化体を得た。
Example 4
A derivative mixture obtained by reacting 10 parts of molasses and 10 parts of ethylene glycol with succinic anhydride to undergo ester carboxylation was obtained. 10 parts of this derivative mixture was dissolved in 10 parts of ethylene glycol, and 10 parts of ethylene glycol glycidyl ether was added thereto to obtain a solution. To this solution, 50 parts of white clay and 0.1 part of an amine catalyst and tin catalyst are added and mixed well. The resulting mixture is formed into a plate shape and allowed to stand at room temperature for one day. Obtained.
実施例５
クラフトリグニン１０部及びエチレングリコール１０部の水酸基を無水コハク酸と反応させてエステルカルボン酸化した誘導体混合物を得た。この誘導体混合物１０部をエチレングリコール１０部に溶解し、これにエチレングリコールグリシジルエーテル１０部を加えて溶液を得た。この溶液に、白とう土５０部及びアミン系触媒及びすず系触媒０．１部を加えてよく混合し、得られた混合物を板状に成形し、１日室温で放置し板状硬化体を得た。
Example 5
A derivative mixture obtained by reacting 10 parts of kraft lignin and 10 parts of ethylene glycol with succinic anhydride to undergo ester carboxylation was obtained. 10 parts of this derivative mixture was dissolved in 10 parts of ethylene glycol, and 10 parts of ethylene glycol glycidyl ether was added thereto to obtain a solution. To this solution, 50 parts of white clay and 0.1 part of an amine catalyst and tin catalyst are added and mixed well. The resulting mixture is formed into a plate shape and allowed to stand at room temperature for one day. Obtained.
実施例６
実施例１において、カルボキシル基含有物として参考例１で示したエステル化生成物を用いた以外は同様にして板状硬化体を得た。
Example 6
In Example 1, a plate-like cured body was obtained in the same manner except that the esterification product shown in Reference Example 1 was used as the carboxyl group-containing substance.
実施例７
実施例１において、カルボキシル基含有物として参考例４で示したエステル化生成物を用いた以外は同様にして板状硬化体を得た。
Example 7
In Example 1, a plate-like cured body was obtained in the same manner except that the esterification product shown in Reference Example 4 was used as the carboxyl group-containing substance.
実施例８
実施例１において、カルボキシル基含有物として参考例５で示したエステル化生成物を用いた以外は同様にして板状硬化体を得た。
Example 8
In Example 1, a plate-like cured body was obtained in the same manner except that the esterification product shown in Reference Example 5 was used as the carboxyl group-containing substance.
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