JPH0412145B2 - - Google Patents
Info
- Publication number
- JPH0412145B2 JPH0412145B2 JP59165455A JP16545584A JPH0412145B2 JP H0412145 B2 JPH0412145 B2 JP H0412145B2 JP 59165455 A JP59165455 A JP 59165455A JP 16545584 A JP16545584 A JP 16545584A JP H0412145 B2 JPH0412145 B2 JP H0412145B2
- Authority
- JP
- Japan
- Prior art keywords
- guide wire
- medical tube
- functional group
- reactive functional
- tube guide
- 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
- 239000000463 material Substances 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 3
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 2
- 229920002401 polyacrylamide Polymers 0.000 claims description 2
- 125000000524 functional group Chemical group 0.000 claims 10
- 239000000126 substance Substances 0.000 claims 9
- 239000011247 coating layer Substances 0.000 claims 7
- 229920003169 water-soluble polymer Polymers 0.000 claims 6
- 239000010410 layer Substances 0.000 claims 5
- 239000002861 polymer material Substances 0.000 claims 5
- 150000001875 compounds Chemical class 0.000 claims 4
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims 2
- 229920003174 cellulose-based polymer Polymers 0.000 claims 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 150000003863 ammonium salts Chemical class 0.000 claims 1
- UPBDXRPQPOWRKR-UHFFFAOYSA-N furan-2,5-dione;methoxyethene Chemical compound COC=C.O=C1OC(=O)C=C1 UPBDXRPQPOWRKR-UHFFFAOYSA-N 0.000 claims 1
- 238000003780 insertion Methods 0.000 claims 1
- 230000037431 insertion Effects 0.000 claims 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 claims 1
- 159000000000 sodium salts Chemical class 0.000 claims 1
- 239000000243 solution Substances 0.000 description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 229920000915 polyvinyl chloride Polymers 0.000 description 3
- 239000004800 polyvinyl chloride Substances 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 238000007654 immersion Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000004006 olive oil Substances 0.000 description 2
- 235000008390 olive oil Nutrition 0.000 description 2
- 229920006122 polyamide resin Polymers 0.000 description 2
- 229920005749 polyurethane resin Polymers 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 230000001953 sensory effect Effects 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 1
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 1
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- -1 and (5) non-coated Substances 0.000 description 1
- 238000002583 angiography Methods 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 238000002586 coronary angiography Methods 0.000 description 1
- 229920001903 high density polyethylene Polymers 0.000 description 1
- 239000004700 high-density polyethylene Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 229920001684 low density polyethylene Polymers 0.000 description 1
- 239000004702 low-density polyethylene Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 229920002246 poly[2-(dimethylamino)ethyl methacrylate] polymer Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920006316 polyvinylpyrrolidine Polymers 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Description
DAEM（Ｎ，Ｎ−ジメチルアミノエチルメタク
リレート）40c.c.、シクロヘキサン10c.c.、
AIBN0.5gを混合し、紫外線を２時間照射して
PDAEM（ポリーＮ，Ｎ−ジメチルアミノエチル
メタクリレート）を合成し、50℃で24時間真空乾
燥した。
PDAEM2g、臭化エチル1.4c.c.、THF18.2c.c.を
よく攪拌して混合した後、オーブン中55℃で２時
間放置したところ、四級化PDAEMの白色沈殿物
が生じた。この沈殿物を、50℃で12時間真空乾燥
した。
四級化PDAEMの８％DMF溶液１体積とPVC
のTHF、DMF溶液（１：１）１体積を混合し、
四級化PDAEMのPVCドープ液を作製した。
このドープ液に、直径0.87mm、長さ100cmのス
テンレス棒を１分間浸漬してドープ液をコート
し、オーブン中にて60℃で２時間乾燥した。
このドープ液コートステンレス棒を、ポリアク
リルアミドのアニオン型（MA−3000−6H）の
0.25％水溶液に１時間浸漬し、その後60℃で２時
間乾燥し、表面潤滑性付与カテーテルガイドワイ
ヤー(1)を得た。
7Fr血管造影用カテーテル内に生理食塩水でぬ
らしたガイドワイヤー(1)を挿入し、操作したとこ
ろ、摺動抵抗が非常に低く、良好であつた。
〔本発明例２〕
ポリエチレングリコール（MW＝1000）10g、
ペンタエリスリトール4g、トルエンジイソシア
ネート16gを反応させ、末端イソシアネート基を
有するポリウレタン樹脂を合成した。
３cm×５cm×0.4tmmに成形したナイロン６製シ
ートを、前記ポリウレタン樹脂でコートした後、
ポリビニルピロリドン（Ｋ−90、平均分子量36
万、GAF社製）の５％クロロホルム溶液中に浸
漬、乾燥し、ポリビニルポロリドンがイオン結合
で基材に担持された試料片(2)を得た。
〔比較例〕
３cm×５cm×0.4tmmで、軟質ポリ塩化ビニル製
の、表面が(3)グリセリンコート、(4)オリーブ油コ
ート、(5)ノンコートである試料片と、同サイズの
(6)低密度ポリエチレン、(7)高密度ポリエチレン、
(8)四フツ化エチレンの試料片を準備した。
これらについて、摩擦抵抗試験、持続性試験を
下記の如く行なつた。結果は表−１および第４図
に示した。
〔摩擦抵抗試験〕
第３図に示すように、試料片３１を傾斜板３２
上に固定し、その上に底面にポリアミド樹脂製シ
ート３３を貼り付けた重さ約100gの鉄製円柱形
状のおもり３４をのせ、傾斜板３２の傾斜角θを
徐々に増大させていつた時、おもり３４が摺動し
始める角度θを求め、μ＝tanθとして摩擦係数を
求めた。また、摩擦係数が0.05未満を優、0.05〜
0.10を良、0.10〜1.00を可、1.00超を不可として
示した。
なお、(3)グリセリンコートおよび(4)オリーブ油
コートについては、コート液にポリ塩化ビニルシ
ートを浸漬し、液が滴下しない程度に振り切つて
試料片を得た。
また、本発明例(1)については、前記したよう
に、カテーテル内を摺動させて官能評価した。
〔持続性試験−摩擦係数の経時変化〕
試料片を１の水中に浸漬し、500〜600rpmに
て攪拌した。水中から取出した試料片について、
第３図に示したような試験方法によつて摩擦係数
を求め、試料片の水中への浸漬時間と摩擦係数と
の関係を調べた。
また、本発明例(1)については、ガイドワイヤー
を同様に水中に浸漬し、水中から取出した後にカ
テーテル内を摺動させて官能評価した。
DAEM (N,N-dimethylaminoethyl methacrylate) 40 c.c., cyclohexane 10 c.c.,
Mix 0.5g of AIBN and irradiate it with ultraviolet light for 2 hours.
PDAEM (poly N,N-dimethylaminoethyl methacrylate) was synthesized and vacuum-dried at 50°C for 24 hours. After thoroughly stirring and mixing 2 g of PDAEM, 1.4 cc of ethyl bromide, and 18.2 c.c. of THF, the mixture was left in an oven at 55°C for 2 hours, resulting in the formation of a white precipitate of quaternized PDAEM. This precipitate was vacuum dried at 50°C for 12 hours. 1 volume of 8% DMF solution of quaternized PDAEM and PVC
Mix 1 volume of THF, DMF solution (1:1),
A PVC dope solution of quaternized PDAEM was prepared. A stainless steel rod with a diameter of 0.87 mm and a length of 100 cm was immersed in this dope solution for 1 minute to coat it with the dope solution, and then dried in an oven at 60° C. for 2 hours. This dope solution coated stainless steel rod was made of polyacrylamide anion type (MA-3000-6H).
It was immersed in a 0.25% aqueous solution for 1 hour and then dried at 60°C for 2 hours to obtain a catheter guidewire (1) with surface lubricity. When the guide wire (1) wetted with physiological saline was inserted into the 7Fr angiography catheter and manipulated, the sliding resistance was very low and good. [Example 2 of the present invention] 10 g of polyethylene glycol (MW = 1000),
4 g of pentaerythritol and 16 g of toluene diisocyanate were reacted to synthesize a polyurethane resin having terminal isocyanate groups. After coating a nylon 6 sheet formed into a size of 3 cm x 5 cm x 0.4 t mm with the polyurethane resin,
Polyvinylpyrrolidone (K-90, average molecular weight 36
The specimen was immersed in a 5% chloroform solution (manufactured by GAF) and dried to obtain a sample piece (2) in which polyvinylporolidone was supported on the base material through ionic bonding. [Comparative example] A sample piece of 3 cm x 5 cm x 0.4 t mm made of soft polyvinyl chloride with a surface coated with (3) glycerin, (4) coated with olive oil, and (5) non-coated, and a sample piece of the same size.
(6) low density polyethylene, (7) high density polyethylene,
(8) A sample piece of tetrafluoroethylene was prepared. These were subjected to a friction resistance test and a durability test as described below. The results are shown in Table 1 and Figure 4. [Frictional resistance test] As shown in FIG.
A cylindrical iron weight 34 weighing about 100 g with a polyamide resin sheet 33 attached to the bottom was placed on top of the weight, and when the inclination angle θ of the inclined plate 32 was gradually increased, the weight The angle θ at which 34 starts sliding was determined, and the coefficient of friction was determined by setting μ=tanθ. In addition, the friction coefficient is less than 0.05, excellent, 0.05~
0.10 was indicated as good, 0.10 to 1.00 as acceptable, and over 1.00 as poor. For (3) glycerin coating and (4) olive oil coating, sample pieces were obtained by immersing a polyvinyl chloride sheet in the coating solution and shaking it off to an extent that the solution would not drip. In addition, regarding the present invention example (1), the sensory evaluation was performed by sliding the catheter inside the catheter as described above. [Durability test - Change in friction coefficient over time] A sample piece was immersed in water of 1 and stirred at 500 to 600 rpm. Regarding the sample piece taken out of the water,
The friction coefficient was determined by the test method shown in FIG. 3, and the relationship between the immersion time of the sample piece in water and the friction coefficient was investigated. Furthermore, regarding Inventive Example (1), the guide wire was immersed in water in the same manner, and after being taken out from the water, it was slid inside the catheter for sensory evaluation.
【表】
表−１および第４図から明らかなように、比較
例は、もともと摩擦抵抗が大きいか、もしくは連
続水洗10分間程度で初期の潤滑性を失つてしまう
ものであつた。それにひきかえ、本発明例は、摩
擦抵抗が小さく、かつ、それが持続した。[Table] As is clear from Table 1 and FIG. 4, the comparative examples either had high frictional resistance or lost their initial lubricity after about 10 minutes of continuous water washing. In contrast, in the examples of the present invention, the frictional resistance was small and continued to be so.
第１図は冠動脈造影用カテーテルの側面図、第
２図は本発明の医療用チユーブガイドワイヤーの
側面図、第３図は摩擦係数を測定する方法を示す
図、第４図は試料の水中への浸漬時間と摩擦係数
との関係を示すグラフである。
符号の説明、１……カテーテル、２……ガイド
ワイヤー、３……被覆層、３１……試料片、３２
……傾斜板、３３……ポリアミド樹脂製シート、
３４……おもり。
Fig. 1 is a side view of a catheter for coronary angiography, Fig. 2 is a side view of a medical tube guide wire of the present invention, Fig. 3 is a diagram showing a method for measuring the coefficient of friction, and Fig. 4 is a diagram showing how a sample is immersed in water. It is a graph showing the relationship between immersion time and friction coefficient. Explanation of symbols, 1... Catheter, 2... Guide wire, 3... Covering layer, 31... Sample piece, 32
... Inclined plate, 33 ... Polyamide resin sheet,
34... Weight.
Claims (1)
体内へ導入または体内から抜去可能なガイドワイ
ヤーであつて、該ガイドワイヤーは、その最外層
として、ガイドワイヤーを構成する基材の少なく
とも表面に存在する反応性官能基とイオン結合し
た水溶性高分子物質またはその誘導体で構成され
る被覆層を有し、湿潤時に該被覆層が湿潤性を有
するように構成したことを特徴とする医療用チユ
ーブガイドワイヤー。 ２ 前記水溶性高分子物質またはその誘導体が、
セルロース系高分子物質、無水マレイン酸系高分
子物質またはアクリルアミド系高分子物質である
特許請求の範囲第１項に記載の医療用チユーブガ
イドワイヤー。 ３ 前記セルロース系高分子物質がカルボキシメ
チルセルロースのナトリウム塩である特許請求の
範囲第２項に記載の医療用チユーブガイドワイヤ
ー。 ４ 前記無水マレイン酸系高分子物質がメチルビ
ニルエーテル無水マレイン酸のナトリウム塩また
はアンモニウム塩である特許請求の範囲第２項に
記載の医療用チユーブガイドワイヤー。 ５ 前記アクリルアミド系高分子物質がポリアク
リルアミドの加水分解物または四級化物である特
許請求の範囲第２項に記載の医療用チユーブガイ
ドワイヤー。 ６ 前記基材の少なくとも表面に存在する反応性
官能基がイソシアネート基または四級アミノ基で
ある特許請求の範囲第１項に記載の医療用チユー
ブガイドワイヤー。 ７ 反応性官能基を有する化合物の溶液で医療用
チユーブガイドワイヤーを構成する基材を処理
し、該基材の少なくとも表面に反応性官能基が存
在するよう下地層を形成し、次いで水溶性高分子
物質またはその誘導体で処理して、該反応性官能
基と該水溶性高分子物質またはその誘導体とをイ
オン結合させ、該下地層上に水溶性高分子物質ま
たはその誘導体で構成される被覆層を形成し、湿
潤時に該被覆層が湿潤性を有するようにしたこと
を特徴とする医療用チユーブガイドワイヤーの製
造方法。 ８ 反応性官能基を有する化合物の溶液で医療用
チユーブガイドワイヤーを構成する基材を処理
し、該基材の少なくとも表面に反応性官能基が存
在するよう下地層を形成し、次いで水溶性高分子
物質またはその誘導体で処理して、該反応性官能
基と該水溶性高分子物質またはその誘導体とをイ
オン結合させ、該下地層上に水溶性高分子物質ま
たはその誘導体で構成される被覆層を形成し、こ
の後、水接触処理を行ない、湿潤時に該被覆層が
湿潤性を有するようにしたことを特徴とする医療
用チユーブガイドワイヤーの製造方法。[Claims] 1. Having an outer diameter that allows insertion into a medical tube,
A guidewire that can be introduced into or removed from the body, the outermost layer of which is a water-soluble polymer ionically bonded to a reactive functional group present on at least the surface of a base material constituting the guidewire. 1. A medical tube guide wire, comprising a coating layer made of a substance or a derivative thereof, and the coating layer is configured to have wettability when wetted. 2 The water-soluble polymer substance or its derivative is
The medical tube guide wire according to claim 1, which is a cellulose-based polymer material, a maleic anhydride-based polymer material, or an acrylamide-based polymer material. 3. The medical tube guide wire according to claim 2, wherein the cellulose-based polymer material is a sodium salt of carboxymethyl cellulose. 4. The medical tube guide wire according to claim 2, wherein the maleic anhydride-based polymeric substance is a sodium salt or ammonium salt of methyl vinyl ether maleic anhydride. 5. The medical tube guide wire according to claim 2, wherein the acrylamide-based polymer material is a hydrolyzate or a quaternized product of polyacrylamide. 6. The medical tube guide wire according to claim 1, wherein the reactive functional group present on at least the surface of the base material is an isocyanate group or a quaternary amino group. 7 Treat the base material constituting the medical tube guide wire with a solution of a compound having a reactive functional group, form a base layer so that the reactive functional group is present on at least the surface of the base material, and then treat the base material with a solution of a compound having a reactive functional group. A coating layer formed of the water-soluble polymer substance or its derivative on the base layer by treatment with a molecular substance or its derivative to cause ionic bonding between the reactive functional group and the water-soluble polymer substance or its derivative; 1. A method for manufacturing a medical tube guide wire, characterized in that the coating layer has wettability when wetted. 8 Treat the base material constituting the medical tube guide wire with a solution of a compound having a reactive functional group, form a base layer so that the reactive functional group is present on at least the surface of the base material, and then treat the base material with a solution of a compound having a reactive functional group. A coating layer formed of the water-soluble polymer substance or its derivative on the base layer by treatment with a molecular substance or its derivative to cause ionic bonding between the reactive functional group and the water-soluble polymer substance or its derivative; 1. A method for manufacturing a medical tube guide wire, comprising: forming a coating layer, and then performing a water contact treatment so that the coating layer has wettability when wetted.
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59165455A JPS6145775A (en) | 1984-08-07 | 1984-08-07 | Medical tube guide and its production |
| EP19850106929 EP0166998B1 (en) | 1984-06-04 | 1985-06-04 | Medical instrument and method for making |
| DE8585106929T DE3582754D1 (en) | 1984-06-04 | 1985-06-04 | MEDICAL TOOL AND PRODUCTION METHOD. |
| AU43278/85A AU566085B2 (en) | 1984-06-04 | 1985-06-04 | Medical instrument with surface treatment |
| US07/240,365 US4876126A (en) | 1984-06-04 | 1988-09-01 | Medical instrument and method for making |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59165455A JPS6145775A (en) | 1984-08-07 | 1984-08-07 | Medical tube guide and its production |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6145775A JPS6145775A (en) | 1986-03-05 |
| JPH0412145B2 true JPH0412145B2 (en) | 1992-03-03 |
Family
ID=15812742
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59165455A Granted JPS6145775A (en) | 1984-06-04 | 1984-08-07 | Medical tube guide and its production |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6145775A (en) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4884579A (en) * | 1988-04-18 | 1989-12-05 | Target Therapeutics | Catheter guide wire |
| JP2510644Y2 (en) * | 1988-10-19 | 1996-09-18 | オリンパス光学工業株式会社 | Insertion aid for endoscope |
| US5091205A (en) * | 1989-01-17 | 1992-02-25 | Union Carbide Chemicals & Plastics Technology Corporation | Hydrophilic lubricious coatings |
| JPH02131402U (en) * | 1989-04-04 | 1990-11-01 | ||
| CA2019063E (en) * | 1989-06-29 | 2000-01-04 | Brian L. Bates | Hydrophilically coated flexible wire guide |
| JPH03236854A (en) * | 1990-02-13 | 1991-10-22 | Hanako Medical Kk | Medical body-insertion tool having lubricating cover and manufacture thereof |
| JP2630066B2 (en) * | 1990-11-30 | 1997-07-16 | 三菱電機株式会社 | Erase method for nonvolatile semiconductor memory device |
| JP2744155B2 (en) * | 1991-10-28 | 1998-04-28 | 株式会社クリニカル・サプライ | Antithrombotic medical device having lubricity when wet and method for producing the same |
| EP0647701B1 (en) * | 1993-03-25 | 1999-10-06 | Asahi Denka Kogyo Kabushiki Kaisha | Refrigerator lubricant and refrigerant composition containing the same |
| JP2657290B2 (en) * | 1993-06-27 | 1997-09-24 | テルモ株式会社 | Guide wire for catheter |
| JP2006271860A (en) * | 2005-03-30 | 2006-10-12 | Japan Lifeline Co Ltd | Medical device and its manufacturing method |
| HUE026060T2 (en) * | 2006-02-01 | 2016-05-30 | Hollister Inc | Methods of applying a hydrophilic coating to a substrate, and substrates having a hydrophilic coating |
| CN101622020B (en) * | 2007-02-28 | 2015-07-01 | 帝斯曼知识产权资产管理有限公司 | Hydrophilic coating |
| BRPI0808118A2 (en) * | 2007-02-28 | 2014-06-17 | Dsm Ip Assets Bv | HYDROPHILIC COATING |
| WO2011074499A1 (en) * | 2009-12-15 | 2011-06-23 | テルモ株式会社 | Medical device and method for producing same |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01195863A (en) * | 1988-12-16 | 1989-08-07 | Terumo Corp | Medical instrument and manufacture thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2518653B2 (en) * | 1987-07-29 | 1996-07-24 | 日本カ−ボン株式会社 | Gasket for internal combustion engine |
-
1984
- 1984-08-07 JP JP59165455A patent/JPS6145775A/en active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01195863A (en) * | 1988-12-16 | 1989-08-07 | Terumo Corp | Medical instrument and manufacture thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6145775A (en) | 1986-03-05 |
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| LAPS | Cancellation because of no payment of annual fees |