JP2000015389A - Binder composition for carbon dioxide curing - Google Patents
Binder composition for carbon dioxide curingInfo
- Publication number
- JP2000015389A JP2000015389A JP10182160A JP18216098A JP2000015389A JP 2000015389 A JP2000015389 A JP 2000015389A JP 10182160 A JP10182160 A JP 10182160A JP 18216098 A JP18216098 A JP 18216098A JP 2000015389 A JP2000015389 A JP 2000015389A
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- JP
- Japan
- Prior art keywords
- carbon dioxide
- urea
- weight
- parts
- phenolic resin
- Prior art date
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Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明は、炭酸ガスを硬化剤
として鋳型を造型する際に用いる炭酸ガス硬化用粘結剤
組成物、及びこれを含有する炭酸ガス硬化用鋳型組成物
に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a binder composition for curing carbon dioxide, which is used when a mold is formed using carbon dioxide as a curing agent, and a mold composition for curing carbon dioxide containing the same.
【０００２】[0002]
【従来の技術】鋳型の製造に用いる粘結剤として、安全
性に優れた炭酸ガスで硬化しうる有機粘結剤が注目され
ている。2. Description of the Related Art As a binder used for producing a mold, an organic binder which is excellent in safety and can be cured with carbon dioxide has been receiving attention.
【０００３】炭酸ガスで硬化しうる有機粘結剤は、例え
ば特公平４−76947号公報や特許第2723376号公報に開示
されている。またこうした粘結剤の鋳型強度改善とし
て、特開平４−147743号公報、特開平５−320477号公
報、特開平５−93127号公報、及び特開平８−206775号
公報は、グリコールエーテル類、ピロリドン化合物等を
粘結剤樹脂の添加剤として用いることを開示している。
しかしこれら添加剤を配合した粘結剤は、鋳型強度改善
が不十分であり、鋳型の表面安定性が悪く、さらに添加
前よりも樹脂粘度が高くなり混練ムラが発生しがちであ
り、またポンプ等で自動供給する時の定量性が悪い。[0003] Organic binders curable by carbon dioxide are disclosed, for example, in Japanese Patent Publication No. 4-76947 and Japanese Patent No. 2723376. As for the improvement of the mold strength of such a binder, JP-A-4-147743, JP-A-5-320477, JP-A-5-93127 and JP-A-8-206775 disclose glycol ethers and pyrrolidone. It discloses that a compound or the like is used as an additive for a binder resin.
However, binders containing these additives do not sufficiently improve the strength of the mold, have poor surface stability of the mold, have a higher resin viscosity than before the addition, and tend to cause uneven kneading. Poor quantification when automatic supply is performed.
【０００４】[0004]
【発明が解決しようとする課題】本発明は、高い鋳型強
度を維持しつつ鋳型の表面安定性を改善し、粘結剤組成
物の粘度上昇を抑制できる粘結剤の提供を目的とする。SUMMARY OF THE INVENTION An object of the present invention is to provide a binder capable of improving the surface stability of a mold while maintaining high mold strength and suppressing an increase in viscosity of the binder composition.
【０００５】[0005]
【課題を解決するための手段】本発明は、炭酸ガス硬化
用水溶性フェノール系樹脂と、環状尿素化合物を含有す
る粘結剤である。The present invention relates to a binder containing a water-soluble phenolic resin for curing carbon dioxide and a cyclic urea compound.
【０００６】[0006]
【発明の実施の形態】本発明の炭酸ガス硬化用水溶性フ
ェノール系樹脂は、アルカリ性レゾールフェノール系樹
脂水溶液と、オキシアニオン化合物と、好ましくは鋳型
強度を向上させる他の添加剤とから構成される。DESCRIPTION OF THE PREFERRED EMBODIMENTS The water-soluble phenolic resin for curing carbon dioxide of the present invention comprises an aqueous solution of an alkaline resole phenolic resin, an oxyanion compound, and preferably other additives for improving the strength of the mold.
【０００７】アルカリ性レゾールフェノール系樹脂水溶
液は、フェノール類を大量のアルカリ性物質の存在下、
水中でアルデヒド類と反応させることによって得ること
ができる。フェノール類は、フェノール化合物及びビス
フェノール化合物から選ばれる１種、又は２種以上の混
合物又は共縮合樹脂でも良い。フェノール化合物として
は、フェノール、クレゾール、レゾルシノール、3,5-キ
シレノール、ノボラックフェノール、その他の置換フェ
ノール等が挙げられ、ビスフェノール化合物としては、
ビスフェノールＡ、ビスフェノールＦ、ビスフェノール
Ｓ等が挙げられる。アルデヒド類としては、ホルムアル
デヒド、アセトアルデヒド、フルフラール等及びその混
合物が挙げられる。アルデヒド類はフェノール系に対し
て1.0〜6.0倍モルが良く、好ましくは1.1〜5.5倍モルが
よい。An aqueous solution of an alkaline resole phenolic resin is prepared by converting phenols in the presence of a large amount of an alkaline substance.
It can be obtained by reacting with aldehydes in water. The phenols may be one kind selected from a phenol compound and a bisphenol compound, or a mixture of two or more kinds or a co-condensation resin. Examples of the phenol compound include phenol, cresol, resorcinol, 3,5-xylenol, novolak phenol, and other substituted phenols.As the bisphenol compound,
Bisphenol A, bisphenol F, bisphenol S and the like can be mentioned. Aldehydes include formaldehyde, acetaldehyde, furfural and the like and mixtures thereof. The aldehyde is preferably 1.0 to 6.0 moles, more preferably 1.1 to 5.5 moles, based on the phenol.
【０００８】アルカリ性物質としては、アルカリ金属水
酸化物をフェノール類に対して0.01〜6.0倍モル、好ま
しくは0.1〜5.0倍モル用いるのが良好である。アルカリ
金属水酸化物としては好ましくは水酸化ナトリウム、水
酸化カリウム、水酸化リチウム及びこれらの混合物であ
り、水酸化カリウムが最も好ましい。As the alkaline substance, it is preferable to use an alkali metal hydroxide in an amount of 0.01 to 6.0 times, preferably 0.1 to 5.0 times, the mole of the phenol. Preferred alkali metal hydroxides are sodium hydroxide, potassium hydroxide, lithium hydroxide and mixtures thereof, with potassium hydroxide being most preferred.
【０００９】反応条件は目的とする分子量に応じ適宜決
めればよいが、25〜90重量％水溶液として25℃の粘度が
10〜300mPa・Sとするのが好ましく、そのためには25〜9
0重量％の反応液を50〜100℃で0.5〜10時間反応させれ
ばよい。The reaction conditions may be appropriately determined according to the desired molecular weight.
It is preferably set to 10 to 300 mPa · S, for which 25 to 9
The reaction solution of 0% by weight may be reacted at 50 to 100 ° C. for 0.5 to 10 hours.
【００１０】オキシアニオン化合物は、硼砂や硼酸等の
硼酸化合物であり、有機炭酸ガス硬化法に不可欠であ
る。これは、オキシアニオン化合物が炭酸ガスを吸収し
てはじめてアイオノマーを形成し、水溶性フェノール系
樹脂を高分子化すると考えられるためである。硼酸や四
硼酸ナトリウム10水和物（硼砂）、四硼酸カリウム10水
和物、メタ硼酸ナトリウム、五硼酸ナトリウム、五硼酸
カリウム等の硼酸塩が好ましい。オキシアニオン化合物
のアルカリ性レゾールフェノール系樹脂水溶液100重量
部に対する添加量は、鋳型の硬化速度及び強度の点から
0.1〜30重量部、好ましくは３〜15重量部が良好であ
る。他のオキシアニオン化合物としては、アルミン酸
塩、スズ酸塩等が挙げられる。The oxyanion compound is a boric acid compound such as borax or boric acid, and is indispensable for the organic carbon dioxide curing method. This is because it is considered that the ionomer is formed only after the oxyanion compound absorbs carbon dioxide, and the water-soluble phenolic resin is polymerized. Borates such as boric acid, sodium tetraborate decahydrate (borax), potassium tetraborate decahydrate, sodium metaborate, sodium pentaborate and potassium pentaborate are preferred. The amount of the oxyanion compound added to 100 parts by weight of the aqueous solution of the alkaline resole phenolic resin is determined based on the curing speed and strength of the mold.
0.1 to 30 parts by weight, preferably 3 to 15 parts by weight are good. Other oxyanion compounds include aluminates, stannates and the like.
【００１１】鋳型強度を向上させる目的で、例えばγ−
アミノプロピルトリエトキシシランやγ-（2-アミノエ
チル）アミノプロピルトリメトキシシラン、γ-グリシ
ドキシプロピルトリエトキシシラン等のシランカップリ
ング剤を使用することができる。これらは混練砂中に添
加して用いてもよいが、粘結剤組成物と併用するのが好
ましい。その添加量はアルカリ性レゾールフェノール系
樹脂水溶液100重量部に対し0.01〜10重量部、好ましく
は0.1〜5.0重量部が良い。For the purpose of improving the mold strength, for example, γ-
Silane coupling agents such as aminopropyltriethoxysilane, γ- (2-aminoethyl) aminopropyltrimethoxysilane, and γ-glycidoxypropyltriethoxysilane can be used. These may be added to the kneading sand and used, but are preferably used in combination with the binder composition. The addition amount is 0.01 to 10 parts by weight, preferably 0.1 to 5.0 parts by weight based on 100 parts by weight of the aqueous solution of the alkaline resole phenolic resin.
【００１２】本発明では、環状尿素化合物が、炭酸ガス
硬化用水溶性フェノール系樹脂に添加される。好ましい
環状尿素化合物は次式により表される。In the present invention, a cyclic urea compound is added to a water-soluble phenolic resin for curing carbon dioxide. Preferred cyclic urea compounds are represented by the following formula:
【００１３】[0013]
【化２】 Embedded image
【００１４】（R1，R2：水素原子、水酸基、メチル基又
はメチロール基 R3：メチレン基又はイソプロピリデン基 R4：メチレン基又はカルボニル基 Ｘ：酸素原子又は硫黄原子 ｎ：０又は１） 好ましい具体的な環状尿素化合物はエチレン尿素、エチ
レンチオ尿素、プロピレン尿素、N,N'-ジメチルエチレ
ン尿素、N,N'-ジヒドロキシエチレン尿素、ジメチロー
ルエチレン尿素、アセトニル尿素、グリコリル尿素であ
り、エチレン尿素、N,N'-ジメチルエチレン尿素が特に
好ましい。(R 1 , R 2 : hydrogen atom, hydroxyl group, methyl group or methylol group R 3 : methylene group or isopropylidene group R 4 : methylene group or carbonyl group X: oxygen atom or sulfur atom n: 0 or 1) Preferred specific cyclic urea compounds are ethylene urea, ethylene thiourea, propylene urea, N, N'-dimethylethylene urea, N, N'-dihydroxyethylene urea, dimethylol ethylene urea, acetonylurea, glycolyl urea, and ethylene urea. And N, N'-dimethylethylene urea are particularly preferred.
【００１５】これらの環状尿素化合物は、粘結剤組成物
中に配合添加して用いられるが、炭酸ガス硬化用水溶性
フェノール系樹脂の合成段階で添加しても良い。また砂
を混練する際に、炭酸ガス硬化用水溶性フェノール系樹
脂と環状尿素化合物を別々に用いても良い。環状尿素化
合物は、低級アルコールや多価アルコール、アセトン、
エステル化合物等を用いた溶剤溶液又は分散液で用いる
こともできる。添加量は本発明の目的を効率よく達成す
るために炭酸ガス硬化用水溶性フェノール系樹脂100重
量部に対して0.1〜30重量部が好ましく、さらに好まし
くは１〜20重量部である。These cyclic urea compounds are used by being added to the binder composition, but may be added at the stage of synthesizing the water-soluble phenolic resin for curing carbon dioxide. When kneading the sand, a water-soluble phenolic resin for curing carbon dioxide and a cyclic urea compound may be used separately. Cyclic urea compounds include lower alcohols, polyhydric alcohols, acetone,
A solvent solution or a dispersion using an ester compound or the like can also be used. The addition amount is preferably 0.1 to 30 parts by weight, more preferably 1 to 20 parts by weight, based on 100 parts by weight of the water-soluble phenolic resin for curing carbon dioxide in order to efficiently achieve the object of the present invention.
【００１６】本発明の炭酸ガス硬化用粘結剤組成物の固
形分（粘結剤組成物２ｇを105℃で３時間乾燥）は、鋳
物砂との均一な混練により優れた鋳型強度を得るため好
ましくは30〜90重量％、さらに好ましくは40〜85重量％
である。The solid content (2 g of the binder composition dried at 105 ° C. for 3 hours) of the binder composition for curing carbon dioxide of the present invention is used to obtain excellent mold strength by uniform kneading with molding sand. Preferably 30 to 90% by weight, more preferably 40 to 85% by weight
It is.
【００１７】本発明の粘結剤組成物を用いて鋳型造型す
る場合、耐火性粒状材料と本発明の粘結剤組成物とをミ
キサー等で混練し、ガス硬化用鋳型模型に混練砂を充填
した後、炭酸ガスを通気して鋳型を造型することができ
る。ミキサーを用いて混練する場合、適度なガス発生量
で優れた品質の鋳物を得るために、耐火性粒状材料100
重量部に対し、本発明の粘結剤組成物を好ましくは0.1
〜15重量部、更に好ましくは0.5〜５重量部用いる。炭
酸ガスの使用量は、鋳型の未硬化を防ぐと共に鋳型の生
産性を維持するために、耐火性粒状材料100重量部に対
して0.01〜30重量部、好ましくは0.1〜15重量部であ
る。なお、炭酸ガスは減圧置換硬化法によって通気させ
てもよい。In the case of molding using the binder composition of the present invention, the refractory granular material and the binder composition of the present invention are kneaded with a mixer or the like, and the kneading sand is filled in a gas curing mold model. After that, carbon dioxide gas is ventilated to form a mold. When kneading using a mixer, a refractory granular material 100
The binder composition of the present invention is preferably 0.1 parts by weight.
To 15 parts by weight, more preferably 0.5 to 5 parts by weight. The amount of carbon dioxide used is 0.01 to 30 parts by weight, preferably 0.1 to 15 parts by weight, based on 100 parts by weight of the refractory granular material in order to prevent uncuring of the mold and maintain the productivity of the mold. The carbon dioxide gas may be aerated by a reduced pressure substitution hardening method.
【００１８】また、混練砂を得る方法として、炭酸ガス
硬化用水溶性フェノール系樹脂と、環状尿素化合物をそ
れぞれ準備しておき、耐火性粒状材料にこれらを別々に
添加し混練することもできる。この時の添加量は、耐火
性粒状材料100重量部に対し、炭酸ガス硬化用水溶性フ
ェノール系樹脂を0.1〜10重量部、環状尿素化合物を0.0
01〜５重量部とするのが好ましく、得られた混練砂を使
用し前述したようにして鋳型を造型することができる。
なお、混練ムラを抑制する意味で、前述の粘結剤組成物
を用いるのが好ましい。As a method of obtaining kneaded sand, a water-soluble phenolic resin for curing carbon dioxide and a cyclic urea compound may be prepared in advance, and these may be separately added to the refractory granular material and kneaded. At this time, the addition amount is 0.1 to 10 parts by weight of the water-soluble phenolic resin for carbon dioxide curing and 0.0 to 0.09 parts by weight of the cyclic urea compound based on 100 parts by weight of the refractory granular material.
The amount is preferably from 01 to 5 parts by weight, and a mold can be formed using the obtained kneaded sand as described above.
In order to suppress uneven kneading, it is preferable to use the above-described binder composition.
【００１９】耐火性粒状材料としては、石英質を主成分
とする珪砂、クロマイト砂、ジルコン砂、オリビン砂、
アルミナ砂、ムライト砂、合成ムライト砂、アルミナボ
ールサンド等が挙げられる。また耐火性粒状材料は、新
砂、再生砂、或いはこれらの混合砂を用いることができ
る。Examples of the refractory granular material include quartz sand, chromite sand, zircon sand, olivine sand, and the like.
Examples include alumina sand, mullite sand, synthetic mullite sand, and alumina ball sand. As the refractory granular material, fresh sand, reclaimed sand, or a mixed sand thereof can be used.
【００２０】本発明の粘結剤組成物、鋳型組成物及び造
型方法で得られる鋳型は、アルミ鋳物のような非鉄合金
や鋳鋼及び鋳鉄鋳物の製造に用いることができ、鋳造に
関する用途に限定はない。The binder composition, the mold composition and the mold obtained by the molding method of the present invention can be used for the production of non-ferrous alloys such as aluminum castings, cast steels and cast iron castings. Absent.
【００２１】[0021]
【発明の効果】本発明の粘結剤組成物を用いると、高い
鋳型強度を維持しつつ鋳型の表面安定性を改善でき、粘
結剤組成物の粘度上昇を抑制することができる。By using the binder composition of the present invention, the surface stability of the mold can be improved while maintaining high mold strength, and the increase in viscosity of the binder composition can be suppressed.
【００２２】[0022]
【実施例】以下の実施例における混練や造型条件は、25
℃、60％ＲＨとした。 ［炭酸ガス硬化用水溶性フェノール樹脂水溶液の合成例
１〜４］表１に示すモル比のアルカリ化合物（Ａ）とフ
ェノール類（Ｐ）の溶液に70℃で、フェノール類に対し
て表１に示すモル比のアルデヒド化合物（Ｆ）を徐々に
加えた。80℃に昇温し、反応溶液中における水溶性フェ
ノール系樹脂水溶液の粘度が25℃で83mPa・sになるまで
反応を続けた。仕込み量に対して硼砂を８重量％、γ−
アミノプロピルトリエトキシシランを１重量％を加え、
樹脂水溶液を得た。EXAMPLES In the following examples, kneading and molding conditions were 25
° C and 60% RH. [Synthesis Examples 1 to 4 of aqueous phenol resin aqueous solution for curing carbon dioxide gas] A solution of an alkali compound (A) and a phenol (P) in a molar ratio shown in Table 1 is shown in Table 1 with respect to phenol at 70 ° C. The molar ratio of the aldehyde compound (F) was gradually added. The temperature was raised to 80 ° C., and the reaction was continued until the viscosity of the aqueous solution of the water-soluble phenolic resin in the reaction solution reached 83 mPa · s at 25 ° C. 8% by weight of borax, γ-
1% by weight of aminopropyltriethoxysilane is added,
A resin aqueous solution was obtained.
【００２３】[0023]
【表１】 [Table 1]
【００２４】実施例１〜14及び比較例１〜６ ［炭酸ガス硬化用粘結剤組成物の配合調整］合成例１〜
４で得られた樹脂溶液に、表２に示す添加剤を10重量％
添加配合し、炭酸ガス硬化用粘結剤組成物を調製した。 ［粘度上昇指数の測定］Ｂ型粘度計を用いて、添加剤を
配合する前と後の粘結剤組成物の25℃における粘度を測
定し、次式に従い算出した。 Examples 1 to 14 and Comparative Examples 1 to 6 [Adjustment of Formulation of Binder Composition for Curing Carbon Dioxide Gas]
10% by weight of the additives shown in Table 2 in the resin solution obtained in
By adding and blending, a binder composition for curing carbon dioxide gas was prepared. [Measurement of Viscosity Increase Index] The viscosity at 25 ° C. of the binder composition before and after compounding the additive was measured using a B-type viscometer, and calculated according to the following equation.
【００２５】[0025]
【数１】 (Equation 1)
【００２６】［鋳型強度の測定］砂温25℃の三河R6号珪
砂1.5kgに、表２に示す粘結剤組成物をそれぞれ45ｇ添
加し、バッチミキサーで１分間混練し、50mmφ×50mmｈ
のテストピース８個取りのガス硬化用木型に充填後、ガ
ス温度30℃、通気量20リットル／分、ガス圧力0.2MPaで
炭酸ガスを30秒間通気した。その後、直ちにテストピー
スを抜型し、24時間放置後の抗圧力（鋳型強度）と表面
安定性を測定した。表面安定性はテストピースを網目16
80μmの篩上で120秒間振とうし、次式に従い算出した。
これらの結果を表２に示す。[Measurement of mold strength] To 1.5 kg of Mikawa R6 silica sand at a sand temperature of 25 ° C, 45 g of each of the binder compositions shown in Table 2 were added and kneaded for 1 minute with a batch mixer to obtain 50 mmφ × 50 mmh.
After the test piece was filled in a gas-curing wooden mold having eight test pieces, carbon dioxide gas was passed for 30 seconds at a gas temperature of 30 ° C., a flow rate of 20 L / min, and a gas pressure of 0.2 MPa. Then, the test piece was immediately removed from the mold, and the pressure resistance (mold strength) and the surface stability after standing for 24 hours were measured. Surface stability mesh test piece 16
The mixture was shaken on an 80 μm sieve for 120 seconds and calculated according to the following equation.
Table 2 shows the results.
【００２７】[0027]
【数２】 (Equation 2)
【００２８】[0028]
【表２】 [Table 2]
【００２９】実施例15〜19及び比較例７ 合成例１〜４で得られた粘結剤に表３に示す量と種類の
環状尿素化合物を配合し、鋳型強度と表面安定性を上記
と同様にして測定した。 Examples 15 to 19 and Comparative Example 7 The binders obtained in Synthesis Examples 1 to 4 were mixed with the amounts and types of cyclic urea compounds shown in Table 3, and the mold strength and surface stability were the same as described above. Was measured.
【００３０】[0030]
【表３】 [Table 3]
【００３１】実施例20〜25及び比較例８〜11 合成例１〜４で得られた粘結剤組成物2.7重量部と表４
に示す添加剤0.3重量部をそれぞれ準備しておき、国産
珪砂７号100重量部にミキサーで混練し、24時間後の抗
圧力及びその混練砂の樹脂混練ムラを評価した。 Examples 20 to 25 and Comparative Examples 8 to 11 2.7 parts by weight of the binder composition obtained in Synthesis Examples 1 to 4 and Table 4
Was prepared and kneaded with 100 parts by weight of domestic quartz sand No. 7 using a mixer, and after 24 hours, the coercive pressure and the resin kneading unevenness of the kneaded sand were evaluated.
【００３２】[0032]
【表４】 [Table 4]
Claims (5)
と、環状尿素化合物を含有する炭酸ガス硬化用粘結剤組
成物。1. A binder composition for curing carbon dioxide, comprising a water-soluble phenolic resin for curing carbon dioxide and a cyclic urea compound.
ノール系樹脂100重量部に対して0.1〜30重量部含有され
る、請求項１の炭酸ガス硬化用粘結剤組成物。2. The binder composition according to claim 1, wherein the cyclic urea compound is contained in an amount of 0.1 to 30 parts by weight based on 100 parts by weight of the water-soluble phenolic resin.
基 R3：メチレン基又はイソプロピリデン基 R4：メチレン基又はカルボニル基 Ｘ：酸素原子又は硫黄原子 ｎ：０又は１）で表される、請求項１又は２の炭酸ガス
硬化用粘結剤組成物。3. The cyclic urea compound represented by the following formula: (R 1 , R 2 : hydrogen atom, hydroxyl group, methyl group or methylol group R 3 : methylene group or isopropylidene group R 4 : methylene group or carbonyl group X: oxygen atom or sulfur atom n: 0 or 1) The binder composition for curing carbon dioxide gas according to claim 1 or 2.
求項１から３の何れか１の炭酸ガス硬化用粘結剤組成物
を0.1〜15重量部含有させてなる炭酸ガス硬化用鋳型組
成物。4. A mold for curing carbon dioxide containing 0.1 to 15 parts by weight of the binder composition for curing carbon dioxide according to claim 1 with respect to 100 parts by weight of the refractory granular material. Composition.
酸ガス硬化用水溶性フェノール系樹脂を0.1〜10重量
部、環状尿素化合物を0.001〜５重量部含有する炭酸ガ
ス硬化用鋳型組成物。5. A mold composition for curing carbon dioxide, comprising 0.1 to 10 parts by weight of a water-soluble phenolic resin for curing carbon dioxide and 0.001 to 5 parts by weight of a cyclic urea compound based on 100 parts by weight of the refractory granular material.
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| JP18216098A JP3933794B2 (en) | 1998-06-29 | 1998-06-29 | Binder composition for carbon dioxide gas curing |
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|---|---|---|---|
| JP18216098A JP3933794B2 (en) | 1998-06-29 | 1998-06-29 | Binder composition for carbon dioxide gas curing |
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Cited By (5)
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|---|---|---|---|---|
| JP2006289396A (en) * | 2005-04-07 | 2006-10-26 | Kao Corp | Method for manufacturing mold |
| JP2009013298A (en) * | 2007-07-05 | 2009-01-22 | Showa Highpolymer Co Ltd | Process for producing water soluble resol resin |
| US7947766B2 (en) | 2003-06-06 | 2011-05-24 | The Procter & Gamble Company | Crosslinking systems for hydroxyl polymers |
| US9017586B2 (en) | 2004-04-29 | 2015-04-28 | The Procter & Gamble Company | Polymeric structures and method for making same |
| WO2023149338A1 (en) * | 2022-02-02 | 2023-08-10 | 花王株式会社 | Binder composition for forming mold |
-
1998
- 1998-06-29 JP JP18216098A patent/JP3933794B2/en not_active Expired - Fee Related
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7947766B2 (en) | 2003-06-06 | 2011-05-24 | The Procter & Gamble Company | Crosslinking systems for hydroxyl polymers |
| US7960453B2 (en) | 2003-06-06 | 2011-06-14 | The Procter & Gamble Company | Crosslinking systems for hydroxyl polymers |
| US8088843B2 (en) | 2003-06-06 | 2012-01-03 | The Procter & Gamble Company | Crosslinking systems for hydroxyl polymers |
| US8129449B2 (en) | 2003-06-06 | 2012-03-06 | The Procter & Gabmle Company | Crosslinking systems for hydroxyl polymers |
| US9340657B2 (en) | 2003-06-06 | 2016-05-17 | The Procter & Gamble Company | Crosslinking systems for hydroxyl polymers |
| US9017586B2 (en) | 2004-04-29 | 2015-04-28 | The Procter & Gamble Company | Polymeric structures and method for making same |
| JP2006289396A (en) * | 2005-04-07 | 2006-10-26 | Kao Corp | Method for manufacturing mold |
| JP4615350B2 (en) * | 2005-04-07 | 2011-01-19 | 花王株式会社 | Mold manufacturing method |
| JP2009013298A (en) * | 2007-07-05 | 2009-01-22 | Showa Highpolymer Co Ltd | Process for producing water soluble resol resin |
| WO2023149338A1 (en) * | 2022-02-02 | 2023-08-10 | 花王株式会社 | Binder composition for forming mold |
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