JP3362140B2 - Method for producing urethane foam with antibacterial, antifungal, deodorant and deodorant functions - Google Patents
Method for producing urethane foam with antibacterial, antifungal, deodorant and deodorant functionsInfo
- Publication number
- JP3362140B2 JP3362140B2 JP30046292A JP30046292A JP3362140B2 JP 3362140 B2 JP3362140 B2 JP 3362140B2 JP 30046292 A JP30046292 A JP 30046292A JP 30046292 A JP30046292 A JP 30046292A JP 3362140 B2 JP3362140 B2 JP 3362140B2
- Authority
- JP
- Japan
- Prior art keywords
- deodorant
- antibacterial
- antifungal
- agent
- antifungal agent
- 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
Landscapes
- Polyurethanes Or Polyureas (AREA)
- Footwear And Its Accessory, Manufacturing Method And Apparatuses (AREA)
- Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
【発明の詳細な説明】
【０００１】
【産業上の利用分野】本発明は、発泡ウレタンの製造方
法に関する。詳しくは、抗菌・抗カビ・防臭・消臭効果
が長期間持続する機能をもった発泡ウレタンの製造方法
に関する。
【０００２】
【従来の技術と問題点】発泡ウレタンに抗菌機能または
消臭機能のいずれか一つを付加した製品はあるが、抗菌
・抗カビ・防臭・消臭の多機能をバランスよくもった製
品は見当たらない。従来の抗菌性を持ったスポンジ製品
では、抗菌ゼオライトや抗菌セラミックなど金属イオン
を結合した無機質の薬剤を多く使用している。しかし、
金属イオンが一部の細菌に対して抗菌性を発現するには
水分の作用を受けることが必要となるため、発泡ウレタ
ンの用途によっては抗菌効果が見られないことが多い。
また、有機系の抗菌剤を試行してみると、ウレタンの発
泡性は極端に低下し、または阻害したり、発泡時の反応
熱によって分解したり、原料であるポリオールとの相溶
性が悪いなどの問題があり実用性に欠けている点が多
い。一方、消臭効果を持った製品は、活性炭やゼオライ
トなど多孔質物質を配合して、臭気成分を吸着すること
で、消臭性を出しているものが多い。しかし、吸着能力
に限界があり、効果の持続性がないなどの欠点がある。
また、有機系消臭剤としては植物からの抽出物がある
が、水溶性のため使用できなかったり、発泡時の反応熱
によって変色、分解があるなど解決すべき問題点を多く
残している。
【０００３】
【課題を解決するための手段】本発明は、抗菌・抗カビ
性能や防臭消臭性能に優れている有機系薬剤を使用し
て、抗菌・抗カビ・防臭・消臭効果のある発泡ウレタン
を製造する方法を提供するものであって、発泡弾性等の
構造上の特性維持と抗菌消臭効果等を合せもつ発泡ウレ
タンの製造を目的とするものである。発泡ウレタン原料
に特殊処理した有機系薬剤を配合して発泡することを基
本的特徴とするものである。
【０００４】ここに本発明は、微粉末化した抗菌抗カビ
剤と、微粉末化した消臭剤を、発泡材原料ポリオールに
配合し、発泡剤、整泡剤、触媒を併用して同時発泡する
ことを特徴とする抗菌・抗カビ・防臭・消臭機能を持っ
た発泡ウレタンの製造方法である。
【０００５】抗菌抗カビ剤は、２ーメトキシカルボニル
アミノーベンズイミダゾールまたは２ーメチルカルボニ
ルアミノーベンズイミダゾールなどのイミダゾール系抗
カビ剤とカルバメイト又はフタルイミド系抗菌剤をエタ
ノールで一度溶液化し、乾燥し微粉末化して使用する。
この微粉末化した抗菌抗カビ剤を使用し、発泡前の原料
ポリオールに混合しておき、同時発泡させることによ
り、発泡性の阻害を低下する事ができる。
【０００６】消臭剤は、フラボノイドまたはカテキンな
どの植物抽出消臭剤をサイクロデキストリン包接溶液と
してから、ポリオールに対して安定な無機系多孔質物質
であるシリカまたはゼオライトなどに含浸吸着させて乾
燥し微粉末化して使用する。サイクロデキストリンに包
接することによって、消臭剤の耐熱性を上げ、消臭効果
の持続性を持たせる事ができる。
【０００７】
【実施例】次に本発明の製造方法の一実施例について説
明する。次は、本発明方法で製造する発泡ウレタンの材
料成分を示すものである。
ポリオール成分 ポリオール 100.0 重量部
発泡剤（水） 2.9 〃
整泡剤 1.3 〃
金属系触媒 0.2 〃
アミン系触媒 0.6 〃
消臭剤 4.5 〃
抗菌抗カビ剤 0.75 〃
イソシアネート成分 イソシアネート 40.0 重量部
この実施例は、上記に示す重量部で材料を準備したもの
である。実施例では、整泡剤・金属系触媒・アミン系触
媒は、公知慣用のものを用いている。なお触媒には、若
干のノウハウがある。この製造方法は、第一に抗菌抗カ
ビ剤の微粉末化工程・消臭剤の微粉末化工程がある。抗
菌抗カビ剤は、抗カビ剤として２ーメトキシカルボニル
アミノーベンズイミダゾールと、抗菌剤としてカルバメ
イトをエタノールで溶液化した後、乾燥し、微粉末化し
ている。抗菌抗カビ剤は、２ーメチルカルボニルアミノ
ーベンズイミダゾールなどのイミダゾール系抗カビ剤や
フタルイミド系抗菌剤を用いてもよい。抗菌抗カビ剤
は、抗菌効果とともに菌の発生を防止してその過程での
防臭効果もある。消臭剤は、フラボノイド（ゲスト）を
サイクロデキストリン（ホスト）包接溶液としてから、
ポリオールに対して安定な無機系多孔質物質であるシリ
カに含浸吸着させて乾燥し微粉末化して使用している。
なお前記と同様の無機系多孔質物質であるゼオライトな
どに吸着乾燥し、微粉末化してもよい。消臭剤はカテキ
ンなどの植物抽出消臭剤を同じ処理して微粉末化したも
のでも使用できる。次に、前記の微粉末化した抗菌抗カ
ビ剤と消臭剤を発泡材原料であるポリオールに混合し、
さらにイソシアネートを加える。発泡剤を混和し、整泡
剤、金属系触媒、アミン系触媒を添加し、発泡処理をお
こない、熱融着発泡ウレタンを製造するのである。
【０００８】第二に発泡体の製造に際しては、前記の微
粉末化した消臭剤と抗菌抗カビ剤を含むポリオール成分
と、イソシアネート成分の液温を15〜25℃、室内温度を
10〜30℃に保つ事が必要である。微粉末化した抗菌抗カ
ビ剤と消臭剤は、発泡材原料であるポリオールに混合し
し攪拌し、さらにイソシアネートを加え、このポリオー
ル成分とイソシアネート成分を電動攪拌機またはウレタ
ン発泡機によって十分に攪拌する。第三に、この混合物
に発泡剤（水）を混和し、整泡剤、金属系触媒、アミン
系触媒を添加し、混合物を所定の環境で発泡させる。そ
の後安定化のため、室温で約１日間静置する。このよう
に本発明方法は、抗菌抗カビ剤の微粉末化工程１・消臭
剤の微粉末化工程２、発泡材原料との混合工程３、発泡
工程４、で構成される。ポリオール成分に対する発泡
剤、整泡剤および触媒の添加量は発泡条件、求められる
製品条件によって随時変化させて、最適な成分量を設定
すれば良い。さらに、ポリオールとイソシアネートの混
合割合は、インデックスで表わすと80〜120 の範囲で設
定可能である。
【０００９】
【発明の効果】上記の方法で製造した発泡ウレタンの抗
菌防臭・抗カビ・消臭性能について確認試験を実施し
た。
【００１０】［抗菌性試験］
１ 試験法 AATCC TEST METHOD 100 法準用
AATCC TEST METHOD 90 法準用
２ 試験菌 Escherichia coli IF012734
（大腸菌）
Staphylococcus aureus IF012732 （黄色ぶどう球
菌）
Pseudomonas aeruginosa IF012689 （緑膿菌）
３ 試験結果
AATCC TEST METHOD 100 法
試 験 菌 減少率
Escherichia coli 99.5 ％
Staphylococcus aureus 100.0 〃
Pseudomonas aeruginosa 97.3 〃
AATCC TEST METHOD 90 法
試 験 菌 阻止帯幅
Escherichia coli 1.2 mm
Staphylococcus aureus 2.2 mm
Pseudomonas aeruginosa 0.0 mm
【００１１】［抗カビ性試験］
１ 試験法 JIS Z2911 準用
２ 試験菌および結果
Aspergillus niger ATCC6241 ３（試料上の菌
の発育なし）
Penicillium citrinum ATCC9849 ３（ 〃
）
Chaetomium globosum IFO6347 ３（ 〃
）
Fusarium nivale 05ー01050 ３（ 〃
）
Cladosporium herbarum 03ー05059 ３（ 〃
）
黒麹カビ 青カビ ケタマカビ 赤カビ 黒
カビ
【００１２】［消臭性能試験］
１ 試験法 ：厚さ３mmにスライスした発泡ウレタンを
10cm2 に裁断して試料とし、１Ｌのガラスコルベンに入
れる。別に濃度調整した臭気成分0.1ml を濾紙に含浸し
て、試料の入ったコルベンに入れてゴム栓で密栓し、40
℃の恒温器内に保持し、経時的に北川式ガス検知管でコ
ルベン内の気相中の臭気成分濃度を測定する。２ 臭気
成分と濃度変化
臭気成分 濃 度 ３０分後 １時間後 ２時間後
アンモニア 300ppm 3.5 0.0 0.0
硫化水素 100ppm 28.0 9.5 4.0
トリメチルアミン 100ppm 11.0 4.0 1.0
イソ吉草酸 25ppm 4.5 2.0 0.0
メチルメルカプタン 20ppm 12.0 7.0 5.0
【００１３】以上のように、本発明に係る抗菌・抗カビ
・防臭・消臭機能をもった発泡ウレタンの製造方法は、
発泡材の原料に、微粉末化した抗菌抗カビ防臭消臭の有
機系薬剤を混合し、発泡剤等を添加して発泡処理を行な
い発泡ウレタンを製造する方法であり、発泡性を低下さ
せずに強い抗菌効果と消臭効果を持続する発泡ウレタン
を得ることができたのである。この製造方法で得た発泡
ウレタンは、発泡弾性等の構造上の特性維持と抗菌消臭
効果等を合せもつ優れた製品となっている。この発泡素
材は、靴の中敷材・靴の内張り・ベッドパッドなど生活
素材として広く利用できる。Description: BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a method for producing urethane foam. More specifically, the present invention relates to a method for producing urethane foam having a function of maintaining antibacterial, antifungal, deodorant, and deodorant effects for a long period of time. 2. Description of the Related Art There is a product in which either an antibacterial function or a deodorant function is added to urethane foam, but it has a good balance of antibacterial, antifungal, deodorant and deodorant functions. Product not found. Conventional antimicrobial sponge products often use inorganic chemicals such as antimicrobial zeolites and antimicrobial ceramics that bind metal ions. But,
In order for metal ions to exhibit antibacterial properties against some bacteria, it is necessary to receive the action of moisture, so that antibacterial effects are often not seen depending on the use of urethane foam.
Also, when trying organic antibacterial agents, urethane foaming properties are extremely reduced or hindered, decomposed by reaction heat at the time of foaming, poor compatibility with polyol as raw material, etc. And there are many points that lack practicality. On the other hand, many products having a deodorizing effect have a deodorizing effect by admixing a porous substance such as activated carbon or zeolite and adsorbing odor components. However, there are drawbacks such as a limited adsorption capacity and no sustained effect.
As an organic deodorant, there is an extract from a plant, but it has many problems to be solved, such as being unusable due to its water solubility, and being discolored and decomposed due to reaction heat at the time of foaming. [0003] The present invention provides an antibacterial, antifungal, deodorant, and deodorizing effect by using an organic agent having excellent antibacterial, antifungal, and deodorant and deodorant properties. An object of the present invention is to provide a method for producing urethane foam, which is intended to produce urethane foam having both structural properties such as foam elasticity and an antibacterial deodorizing effect. It is a basic feature that foaming is carried out by blending a specially treated organic chemical with a foamed urethane raw material. [0004] Here, the present invention relates to a method of blending a micronized antibacterial and antifungal agent and a micronized deodorant into a foaming material raw material polyol and simultaneously using a foaming agent, a foam stabilizer and a catalyst to form a foam simultaneously. A method for producing urethane foam having antibacterial, antifungal, deodorant, and deodorant functions. [0005] An antibacterial antifungal agent is a solution of an imidazole antifungal agent such as 2-methoxycarbonylamino-benzimidazole or 2-methylcarbonylamino-benzimidazole and a carbamate or phthalimide antibacterial agent once in ethanol, dried and finely dried. Powdered and used.
By using this micronized antibacterial and antifungal agent, mixing it with the raw material polyol before foaming, and foaming simultaneously, the inhibition of foaming properties can be reduced. [0006] The deodorant is prepared by converting a plant-extracted deodorant such as flavonoid or catechin into a cyclodextrin inclusion solution and then impregnating and adsorbing it onto silica or zeolite, which is an inorganic porous substance that is stable to polyol, and drying. And then use it as fine powder. Inclusion with cyclodextrin can increase the heat resistance of the deodorant and provide a sustained deodorant effect. Next, an embodiment of the manufacturing method of the present invention will be described. The following shows the material components of the urethane foam produced by the method of the present invention. Polyol component Polyol 100.0 parts by weight Blowing agent (water) 2.9 泡 Foam stabilizer 1.3 〃 Metal catalyst 0.2 ア ミ ン Amine catalyst 0.6 〃 Deodorant 4.5 〃 Antibacterial antifungal agent 0.75 〃 Isocyanate component Isocyanate 40.0 parts by weight Materials were prepared in the above parts by weight. In Examples, known and commonly used foam stabilizers, metal catalysts, and amine catalysts are used. The catalyst has some know-how. This production method includes a first step of pulverizing an antibacterial antifungal agent and a step of pulverizing a deodorant. The antibacterial antifungal agent is prepared by forming a solution of 2-methoxycarbonylamino-benzimidazole as an antifungal agent and carbamate as an antibacterial agent with ethanol, followed by drying and pulverization. As the antibacterial antifungal agent, an imidazole antifungal agent such as 2-methylcarbonylamino-benzimidazole or a phthalimide antibacterial agent may be used. The antibacterial and antifungal agent has an antibacterial effect and also has a deodorizing effect in the process by preventing the occurrence of bacteria. The deodorant converts the flavonoid (guest) into a cyclodextrin (host) inclusion solution,
It is used after being impregnated and adsorbed on silica, which is an inorganic porous material that is stable to polyol, dried and pulverized.
In addition, it may be adsorbed and dried on zeolite or the like which is the same inorganic porous substance as described above, and may be pulverized. As the deodorant, those obtained by subjecting a plant extraction deodorant such as catechin to the same treatment and pulverizing the same can be used. Next, the micronized antibacterial antifungal agent and the deodorant were mixed with a polyol as a foam material raw material,
Further isocyanate is added. The foaming agent is mixed, a foam stabilizer, a metal-based catalyst, and an amine-based catalyst are added, and a foaming treatment is performed to produce a heat-sealed urethane foam. Second, when producing the foam, the liquid temperature of the above-mentioned finely divided polyol component containing the deodorant and the antibacterial and antifungal agent and the isocyanate component is 15 to 25 ° C.
It is necessary to keep it at 10-30 ° C. The micronized antibacterial and antifungal agent and the deodorant are mixed with the polyol as the foaming material and stirred, and isocyanate is further added. This polyol component and the isocyanate component are sufficiently stirred by an electric stirrer or a urethane foaming machine. . Third, a foaming agent (water) is mixed with the mixture, and a foam stabilizer, a metal catalyst, and an amine catalyst are added, and the mixture is foamed in a predetermined environment. Thereafter, it is allowed to stand at room temperature for about 1 day for stabilization. As described above, the method of the present invention is composed of the step of pulverizing the antibacterial and antifungal agent 1, the step of pulverizing the deodorant 2, the step of mixing with the foam material 3, and the step of foaming 4. The amount of the foaming agent, foam stabilizer and catalyst added to the polyol component may be changed as needed depending on the foaming conditions and the required product conditions, and the optimum component amounts may be set. Further, the mixing ratio of the polyol and the isocyanate can be set in the range of 80 to 120 in terms of an index. The confirmation test was carried out on the antibacterial / deodorant / antifungal / deodorant performance of the urethane foam produced by the above method. [Antibacterial test] 1 Test method AATCC TEST METHOD 100 Applicable method AATCC TEST METHOD 90 Applicable method 2 Test bacteria Escherichia coli IF012734
(Escherichia coli) Staphylococcus aureus IF012732 (Staphylococcus aureus) Pseudomonas aeruginosa IF012689 (Pseudomonas aeruginosa) 3 Test results AATCC TEST METHOD 100 Method Test bacteria reduction rate Escherichia coli 99.5% Staphylococcus aureus 100.0 〃 Pseudomonas aeruginosa 97.3 EST ATC 90 method Test Inhibitory band width Escherichia coli 1.2 mm Staphylococcus aureus 2.2 mm Pseudomonas aeruginosa 0.0 mm Penicillium citrinum ATCC9849 3 (〃
) Chaetomium globosum IFO6347 3 (〃
Fusarium nivale 05 ー 01050 3 （（
) Cladosporium herbarum 03 ー 05059 3 (〃
) Black mold Aspergillus blue mold Ketama fungus Red mold Black mold [Deodorizing performance test] 1 Test method: Urethane foam sliced to a thickness of 3 mm
The sample is cut into 10 cm 2 and placed in a 1 L glass corvene. Separate the filter paper with 0.1 ml of separately adjusted odor component, put it in a kolben containing the sample, and tightly close it with a rubber stopper.
Keep in a constant temperature oven at ℃ and measure the concentration of odor components in the gas phase inside the Kolben with the aid of a Kitagawa gas detector tube over time. 2 Odor component and concentration change Odor component concentration 30 minutes 1 hour 2 hours Ammonia 300 ppm 3.5 0.0 0.0 Hydrogen sulfide 100 ppm 28.0 9.5 4.0 Trimethylamine 100 ppm 11.0 4.0 1.0 Isovaleric acid 25 ppm 4.5 2.0 0.0 Methyl mercaptan 20 ppm 12.0 7.0 5.0 As described above, the method for producing the urethane foam having the antibacterial, antifungal, deodorant, and deodorant functions according to the present invention comprises:
This is a method of producing a foamed urethane by mixing a finely powdered antibacterial, antifungal, deodorant, and deodorizing organic agent into the raw material of the foaming material, adding a foaming agent, etc., and performing a foaming treatment, without reducing foamability. It is possible to obtain urethane foam which maintains a strong antibacterial effect and deodorant effect. The urethane foam obtained by this production method is an excellent product having both structural properties such as foam elasticity and an antibacterial deodorizing effect. This foam material can be widely used as a living material such as insole materials for shoes, lining of shoes, and bed pads.
【図面の簡単な説明】
【図１】本発明に係る抗菌・抗カビ・防臭・消臭機能を
持った発泡ウレタンの製造方法の工程図。
【符号の説明】
１ 抗菌抗カビ剤の微粉末化工程
２ 消臭剤の微粉末化工程
３ 発泡材原料との混合工程
４ 発泡工程BRIEF DESCRIPTION OF THE DRAWINGS FIG. 1 is a process diagram of a method for producing a urethane foam having antibacterial, antifungal, deodorant, and deodorant functions according to the present invention. [Description of Signs] 1 Micronizing step of antibacterial and antifungal agent 2 Micronizing step of deodorant 3 Mixing step with foam material 4 Foaming step
───────────────────────────────────────────────────── フロントページの続き (56)参考文献 特開 平２−47140（ＪＰ，Ａ) 特開 昭60−217247（ＪＰ，Ａ) 特開 平３−231964（ＪＰ，Ａ) 特開 平３−9950（ＪＰ，Ａ) 特開 昭62−241932（ＪＰ，Ａ) 特開 平１−311168（ＪＰ，Ａ) 特開 平１−161053（ＪＰ，Ａ) 特開 昭62−35016（ＪＰ，Ａ) (58)調査した分野(Int.Cl.7，ＤＢ名) C08G 18/00 - 18/87 C08L 75/04 - 75/12 ────────────────────────────────────────────────── ─── Continuation of the front page (56) References JP-A-2-47140 (JP, A) JP-A-60-217247 (JP, A) JP-A-3-231964 (JP, A) JP-A-3-231 9950 (JP, A) JP-A-62-241932 (JP, A) JP-A-1-3111168 (JP, A) JP-A-1-161053 (JP, A) JP-A-62-135016 (JP, A) (58) Field surveyed (Int. Cl. 7 , DB name) C08G 18/00-18/87 C08L 75/04-75/12
Claims (1)
化した消臭剤を、原料ポリオールに配合し、発泡剤、整
泡剤、触媒を併用して同時発泡して発泡ウレタンを得る
発泡ウレタンの製造方法であって、前記微粉末化した抗
菌抗カビ剤が、２ーメトキシカルボニルアミノーベンズ
イミダゾールまたは２ーメチルカルボニルアミノーベン
ズイミダゾールなどのイミダゾール系抗カビ剤とカルバ
メイト又はフタルイミド系抗菌剤をエタノールで一度溶
液化し、これを乾燥し微粉末化した有機系抗菌抗カビ剤
であり、前記微粉末化した消臭剤が、フラボノイドまた
はカテキンなどの植物抽出消臭剤をサイクロデキストリ
ン包接溶液としてから、無機系多孔質物質であるシリカ
またはゼオライトなどに含浸吸着させ、乾燥し微粉末化
した有機系消臭剤であることを特徴とする抗菌・抗カビ
・防臭・消臭機能をもった発泡ウレタンの製造方法。(57) [Claims] [Claim 1] A micronized antibacterial and antifungal agent and a micronized deodorant are blended into a raw material polyol, and a foaming agent, a foam stabilizer, and a catalyst are used in combination. A foamed urethane foamed simultaneously to obtain a foamed urethane, wherein the micronized antibacterial antifungal agent is an imidazole-based agent such as 2-methoxycarbonylamino-benzimidazole or 2-methylcarbonylamino-benzimidazole. An antifungal agent and a carbamate or phthalimide-based antibacterial agent are once dissolved in ethanol, dried, and finely powdered to form an organic antibacterial antifungal agent, wherein the finely powdered deodorant is a plant such as a flavonoid or catechin. Extractive deodorant is converted into cyclodextrin clathrate solution, impregnated and adsorbed on inorganic porous material such as silica or zeolite, dried and fine powder Method for producing a urethane foam having antifungal deodorant deodorant function, characterized in that the organic-based deodorant.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP30046292A JP3362140B2 (en) | 1992-10-13 | 1992-10-13 | Method for producing urethane foam with antibacterial, antifungal, deodorant and deodorant functions |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP30046292A JP3362140B2 (en) | 1992-10-13 | 1992-10-13 | Method for producing urethane foam with antibacterial, antifungal, deodorant and deodorant functions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH06122746A JPH06122746A (en) | 1994-05-06 |
| JP3362140B2 true JP3362140B2 (en) | 2003-01-07 |
Family
ID=17885088
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP30046292A Expired - Lifetime JP3362140B2 (en) | 1992-10-13 | 1992-10-13 | Method for producing urethane foam with antibacterial, antifungal, deodorant and deodorant functions |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3362140B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105615134A (en) * | 2016-03-15 | 2016-06-01 | 崔仕生 | Sterilization shoe pad |
| CN105708046A (en) * | 2016-03-15 | 2016-06-29 | 崔仕生 | Preparation method of sterilization insole |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20000005592A (en) * | 1998-06-02 | 2000-01-25 | 김권 | Polymer composition comprising natural stabilizer |
| JP3843410B2 (en) * | 2000-08-28 | 2006-11-08 | イージェイ株式会社 | Antibacterial cold insulation material |
| JP2005154533A (en) * | 2003-11-25 | 2005-06-16 | Nippon Polyurethane Ind Co Ltd | Method for producing flexible polyurethane foam |
| JP4676973B2 (en) * | 2007-07-26 | 2011-04-27 | 稲畑産業株式会社 | Grip tape |
| JP5279285B2 (en) * | 2008-01-30 | 2013-09-04 | 株式会社イノアックコーポレーション | Deodorant polyurethane foam |
| JP5232600B2 (en) * | 2008-10-29 | 2013-07-10 | ベック株式会社 | Polyol composition |
-
1992
- 1992-10-13 JP JP30046292A patent/JP3362140B2/en not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105615134A (en) * | 2016-03-15 | 2016-06-01 | 崔仕生 | Sterilization shoe pad |
| CN105708046A (en) * | 2016-03-15 | 2016-06-29 | 崔仕生 | Preparation method of sterilization insole |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH06122746A (en) | 1994-05-06 |
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