JPH0427940B2 - - Google Patents
Info
- Publication number
- JPH0427940B2 JPH0427940B2 JP18166684A JP18166684A JPH0427940B2 JP H0427940 B2 JPH0427940 B2 JP H0427940B2 JP 18166684 A JP18166684 A JP 18166684A JP 18166684 A JP18166684 A JP 18166684A JP H0427940 B2 JPH0427940 B2 JP H0427940B2
- Authority
- JP
- Japan
- Prior art keywords
- vinyl chloride
- chloride resin
- ethylene
- alcohol copolymer
- silicone rubber
- 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
Links
- 229920005989 resin Polymers 0.000 claims description 59
- 239000011347 resin Substances 0.000 claims description 59
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims description 56
- 229920000219 Ethylene vinyl alcohol Polymers 0.000 claims description 33
- 229920002379 silicone rubber Polymers 0.000 claims description 33
- 239000004945 silicone rubber Substances 0.000 claims description 20
- 239000004944 Liquid Silicone Rubber Substances 0.000 claims description 13
- 238000012644 addition polymerization Methods 0.000 claims description 13
- 239000003381 stabilizer Substances 0.000 claims description 13
- -1 polysiloxane Polymers 0.000 claims description 12
- 229910052751 metal Inorganic materials 0.000 claims description 11
- 239000002184 metal Substances 0.000 claims description 11
- 229920006136 organohydrogenpolysiloxane Polymers 0.000 claims description 8
- 229920001577 copolymer Polymers 0.000 claims description 7
- 238000010438 heat treatment Methods 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- 229920001296 polysiloxane Polymers 0.000 claims description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
- 238000000576 coating method Methods 0.000 claims description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 3
- 229910052791 calcium Inorganic materials 0.000 claims description 3
- 239000011575 calcium Substances 0.000 claims description 3
- 229910052725 zinc Inorganic materials 0.000 claims description 3
- 239000011701 zinc Substances 0.000 claims description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 2
- 239000011248 coating agent Substances 0.000 claims description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims 1
- 229910052782 aluminium Inorganic materials 0.000 claims 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims 1
- 229910052788 barium Inorganic materials 0.000 claims 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims 1
- 229910052749 magnesium Inorganic materials 0.000 claims 1
- 239000011777 magnesium Substances 0.000 claims 1
- 239000004014 plasticizer Substances 0.000 description 23
- 238000007792 addition Methods 0.000 description 11
- 239000000243 solution Substances 0.000 description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- 239000008280 blood Substances 0.000 description 9
- 210000004369 blood Anatomy 0.000 description 9
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 8
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 8
- 238000010828 elution Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 230000002785 anti-thrombosis Effects 0.000 description 6
- 230000004888 barrier function Effects 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 239000005038 ethylene vinyl acetate Substances 0.000 description 5
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 5
- 239000012153 distilled water Substances 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- 239000003549 soybean oil Substances 0.000 description 4
- 235000012424 soybean oil Nutrition 0.000 description 4
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 229910001882 dioxygen Inorganic materials 0.000 description 3
- 238000001802 infusion Methods 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 239000003125 aqueous solvent Substances 0.000 description 2
- 239000013060 biological fluid Substances 0.000 description 2
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 2
- 235000013539 calcium stearate Nutrition 0.000 description 2
- 239000008116 calcium stearate Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- UQLDLKMNUJERMK-UHFFFAOYSA-L di(octadecanoyloxy)lead Chemical compound [Pb+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O UQLDLKMNUJERMK-UHFFFAOYSA-L 0.000 description 2
- 239000004205 dimethyl polysiloxane Substances 0.000 description 2
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 239000000944 linseed oil Substances 0.000 description 2
- 235000021388 linseed oil Nutrition 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 238000009832 plasma treatment Methods 0.000 description 2
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920001843 polymethylhydrosiloxane Polymers 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 2
- QMMJWQMCMRUYTG-UHFFFAOYSA-N 1,2,4,5-tetrachloro-3-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=C(Cl)C(Cl)=CC(Cl)=C1Cl QMMJWQMCMRUYTG-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 description 1
- 240000005578 Rivina humilis Species 0.000 description 1
- 229920002433 Vinyl chloride-vinyl acetate copolymer Polymers 0.000 description 1
- 229920006243 acrylic copolymer Polymers 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 230000010062 adhesion mechanism Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000002390 adhesive tape Substances 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- AGXUVMPSUKZYDT-UHFFFAOYSA-L barium(2+);octadecanoate Chemical compound [Ba+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O AGXUVMPSUKZYDT-UHFFFAOYSA-L 0.000 description 1
- ZFMQKOWCDKKBIF-UHFFFAOYSA-N bis(3,5-difluorophenyl)phosphane Chemical compound FC1=CC(F)=CC(PC=2C=C(F)C=C(F)C=2)=C1 ZFMQKOWCDKKBIF-UHFFFAOYSA-N 0.000 description 1
- 210000001124 body fluid Anatomy 0.000 description 1
- 239000010839 body fluid Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- KRGNPJFAKZHQPS-UHFFFAOYSA-N chloroethene;ethene Chemical group C=C.ClC=C KRGNPJFAKZHQPS-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 229920001038 ethylene copolymer Polymers 0.000 description 1
- 239000004715 ethylene vinyl alcohol Substances 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- RZXDTJIXPSCHCI-UHFFFAOYSA-N hexa-1,5-diene-2,5-diol Chemical compound OC(=C)CCC(O)=C RZXDTJIXPSCHCI-UHFFFAOYSA-N 0.000 description 1
- JYVHOGDBFNJNMR-UHFFFAOYSA-N hexane;hydrate Chemical compound O.CCCCCC JYVHOGDBFNJNMR-UHFFFAOYSA-N 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000001617 migratory effect Effects 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical class OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
- 150000003021 phthalic acid derivatives Chemical class 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000012779 reinforcing material Substances 0.000 description 1
- 238000004626 scanning electron microscopy Methods 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
Landscapes
- Laminated Bodies (AREA)
Description
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[Industrial Application Field] The present invention is directed to a soft vinyl chloride resin multilayer laminate and its production, which has extremely little elution of plasticizers and does not impair the original transparency, flexibility, etc. of the soft vinyl chloride resin. It is about the method. [Prior Art] Soft vinyl chloride resins with added plasticizers are widely used for various medical devices such as blood circuits, food packaging, etc. due to their excellent transparency, flexibility, and processability. However, it is known that when a soft vinyl chloride resin product containing a plasticizer etc. is brought into contact with an aqueous solvent such as water, blood, etc., the plasticizer etc. will be eluted. Various methods for preventing the elution of plasticizers have been studied in the past, for example,
There are plasma treatments as seen in publications such as
It is difficult to sufficiently treat the inner surface of a narrow tube, and there is also a concern that other performances such as antithrombotic properties may deteriorate due to plasma treatment. Additionally, multilayer laminates of soft vinyl chloride resins and polyurethane or EVA (ethylene-vinyl acetate copolymer) have been proposed, but at present they have not been able to sufficiently prevent plasticizer elution. Furthermore, when using a non-migratory plasticizer, such as a polyester plasticizer, there is a problem that a sufficient plasticizing effect cannot be obtained. [Purpose of the Invention] The present invention is based on various studies aimed at significantly reducing the elution of plasticizers, etc. from soft vinyl chloride resins, and obtaining molded products with excellent antithrombotic properties in the medical field. As a result, when an ethylene-vinyl alcohol copolymer with excellent oxygen gas barrier properties is combined with a soft vinyl chloride resin to form a multilayer laminate, almost no plasticizer can pass through, even when it comes into contact with an aqueous solvent or blood. I have learned that it is not allowed. This is the result of applying the knowledge that the present inventors previously disclosed in Japanese Patent Application No. 58-203699 etc. that addition polymerization type silicone compositions exhibit excellent adhesion to soft vinyl chloride resins. discovered that a soft vinyl chloride resin and an ethylene-vinyl alcohol copolymer could be bonded together using an addition-polymerized liquid silicone rubber, and conducted various studies to complete the present invention. The purpose is to significantly reduce or prevent the elution of plasticizers, etc., without impairing the transparency and flexibility of soft vinyl chloride resins, and to create products with excellent antithrombotic properties in the medical field. An object of the present invention is to provide a soft vinyl chloride resin multilayer laminate. [Structure of the Invention] That is, the present invention provides a flexible vinyl chloride resin multilayer laminate comprising at least three layers of a flexible vinyl chloride resin, an ethylene-vinyl alcohol copolymer, and an addition-polymerized silicone rubber. In particular, at least three layers constituting the laminate are soft vinyl chloride resin/addition silicone rubber/ethylene-vinyl alcohol copolymer, or soft vinyl chloride resin/addition silicone rubber/ethylene-vinyl alcohol. The present invention relates to a soft vinyl chloride resin multilayer laminate characterized in that a copolymer/addition polymer silicone rubber are laminated in this order, and a method for producing the same. In the present invention, the soft vinyl chloride resin refers to vinyl chloride homopolymer, vinyl chloride-ethylene copolymer, vinyl chloride-vinyl acetate copolymer, vinyl chloride-ethylene-vinyl acetate terpolymer, vinyl chloride -The main component is a copolymer mainly composed of vinyl chloride, such as an acrylic copolymer, a vinyl chloride-urethane copolymer, and a plasticizer, etc., which imparts flexibility to the copolymer. Examples of plasticizers include phthalate esters such as dioctyl phthalate, fatty acid esters such as aliphatic dibasic acid esters such as dioctyl adipate and dibutyl sebaciate, polyester plasticizers, epoxidized soybean oil, and epoxidized linseed oil. etc. are used. As mentioned above, many plasticizers can be used, but if a large amount of any of them is added, the adhesion to silicone rubber tends to weaken. Among these, there are phthalic acid esters, mainly dioctyl phthalate, and epoxidized soybean oil or epoxidized linseed oil, which can maintain relatively adhesive strength, and these are particularly preferred as plasticizers to be used. Furthermore, non-liquid polymers that give flexibility to vinyl chloride resin, such as urethane,
Additions such as EVA also fall into this category. Further, as stabilizers that impart heat resistance and thermal stability, in addition to metal soaps such as calcium stearate, zinc stearate, magnesium stearate, and lead stearate, organic metal stabilizers and inorganic metal stabilizers of the above metals, Ester stabilizers such as organotin stabilizers, organosilicone stabilizers, and butyl stearate can be used, but preferably metal soaps such as calcium stearate, zinc stearate, lead stearate, barium stearate, and the above Organometallic stabilizers and inorganic metal stabilizers of metals are preferred. The addition polymerization type silicone rubber in the present invention refers to a vinyl group-containing polysiloxane represented by the general formula (1), an organohydrogen polysiloxane represented by the general formula (2), and silica as a reinforcing material. It is a composition that can be solidified into an elastic body by addition polymerizing an inorganic composition with a platinum-based catalyst, and the organohydrogensiloxane unit represented by the general formula (2) is formed by the general formula (1). An organohydrogenpolysiloxane having two or more hydrogen atoms in one molecule is contained in an amount sufficient to provide hydrogen atoms directly bonded to silicon atoms at a ratio of 1 to 6 times the total vinyl groups shown in It is something that exists. [In the formula, R 1 to R 5 , R 7 to R 10 : Same or different monovalent hydrocarbon groups having 6 or less carbon atoms R 6 : Hydrogen group or same or different monovalent hydrocarbon groups having 3 or less carbon atoms Group m: Positive integer n: Integer from 2 to 100 l: Positive integer from 0 to 100] The ethylene-vinyl alcohol copolymer in the present invention is usually prepared by saponifying the ethylene-vinyl acetate copolymer. It is preferable to use a resin obtained by using a resin having a particularly high oxygen gas barrier property. It is generally known that the oxygen gas barrier properties of ethylene-vinyl alcohol copolymers deteriorate when they absorb moisture. This is based on the discovery that, surprisingly, the barrier properties against plasticizers such as or,
When adhering a pre-formed ethylene-vinyl alcohol copolymer and a soft vinyl chloride resin via an addition-polymerized liquid silicone rubber, the ethylene-vinyl alcohol copolymer may be used as is, but In order to bond the pre-cured addition polymer silicone rubber and the ethylene-vinyl alcohol copolymer, the ethylene-vinyl alcohol copolymer must contain at least 30 mol of organohydrogensiloxane units per 100 parts by weight of the resin. % or more of organohydrogenpolysiloxane in an amount of 0.01 to 5 parts by weight, preferably 0.1 to 2 parts by weight. If the amount of organohydrogenpolysiloxane added is less than 0.01 parts by weight, there will be no effect and adhesion will be difficult, and if it exceeds 5 parts by weight, transparency will be markedly reduced and the ethylene-vinyl alcohol copolymer will become a barrier to plasticizers. Sexuality decreases. There are two methods for producing the flexible vinyl chloride resin multilayer laminate in the present invention. The first method is to prepare a pre-formed soft vinyl chloride resin molded product (for example, a sheet) and a pre-formed ethylene-vinyl alcohol copolymer molded product (for example, a film), and then Addition-polymerizable liquid silicone rubber or its organic solvent solution is applied to the molded product by a coating method, a spray method, etc., and the other molded product is laminated on top of the molded product without introducing air, and then heated in a heating furnace. 40â to 130â depending on the temperature, preferably 80â
At a temperature of 5 minutes to 10 hours, preferably 10 to 120°C.
The layers are laminated and integrated over a period of minutes to 3 hours. Alternatively, a cured layer of addition polymerizable silicone rubber may be further provided on the surface of the ethylene-vinyl alcohol copolymer by a similar method. The second manufacturing method consists of a pre-molded soft vinyl chloride resin molded article (e.g. tube), an organic solvent solution of addition polymerized liquid silicone rubber, and an ethylene-vinyl alcohol copolymer to which organohydrogen polysiloxane is added. Prepare each organic solvent solution, apply it to the surface and heat it to 40â
After heating at 130°C for 5 minutes to 10 hours, and after curing, apply it thereon and dry under reduced pressure at 40°C to 100°C, or further apply on the surface of the ethylene-vinyl alcohol copolymer layer, 40âïœ130â
You can heat it for 5 minutes to 10 hours. The solvent used for the preparation of and is n-hexane, water and n-hexane.
- A mixed solvent of propyl alcohol can be used. Further, the coating method used is a dipping method, a spraying method, etc., but is not particularly limited. Since the multilayer laminate of the present invention is mainly intended for use in the medical field, the outermost layer, which comes into contact with infusions, body fluids such as blood, and living tissues, is an addition polymerization type with excellent antithrombotic properties. Either silicone rubber or ethylene-vinyl alcohol copolymer may be used, but if ethylene-vinyl alcohol copolymer is the outermost layer, it may easily cause cracks or absorb water depending on the application. Since it is easy to use, it is preferable to use addition polymerization type silicone rubber as the outermost layer in applications requiring elasticity. Therefore, when only one side is in contact with biological fluid or tissue, such as sheet-like multilayer laminates used for infusion bags, blood bags, etc., or tube-shaped multilayer laminates used for blood circuits, soft It is sufficient to laminate a soft vinyl chloride resin/addition polymer silicone rubber/ethylene-vinyl alcohol copolymer in this order on only one side of the vinyl chloride resin, and then laminate another layer of addition polymer silicone rubber if necessary. For applications that are inserted or indwelled into the body, such as catheters, and both sides are in contact with biological fluids or tissues, soft vinyl chloride resin/addition polymer silicone rubber/ Layering ethylene-vinyl alcohol copolymer in this order,
Addition polymerization type silicone rubber is further laminated as necessary. The thickness of each layer in the soft vinyl chloride resin multilayer laminate of the present invention is not particularly limited, but in view of strength, transparency, flexibility, price, etc., the soft vinyl chloride resin layer accounts for most of the thickness. The thickness of the ethylene-vinyl alcohol copolymer layer is desirably 1 Ό to 50 Ό, preferably 5 Ό to 10 Ό in order to provide a barrier effect against the plasticizer. Furthermore, the thickness of the addition-polymerized silicone rubber layer is to play a role in adhesion to the ethylene-vinyl alcohol copolymer or soft vinyl chloride resin, and to impart rubber-like elasticity to the multilayer laminate. 10Ό to 200Ό, preferably 30Ό to 100Ό
is suitable. The mechanism of adhesion between each layer of the multilayer laminate according to the present invention has basically already been disclosed in Japanese Patent Application No. 58-95689 and Tokugan No. 58-203699, but based on these findings, The adhesion mechanism between the soft vinyl chloride resin and the addition polymerization type liquid silicone rubber, and between the ethylene-vinyl alcohol copolymer and the addition polymerization type liquid silicone rubber is as shown in equation (3), respectively. It is presumed that the organohydrogensiloxy group contained in the organohydrogenpolysiloxane in the liquid silicone rubber undergoes an addition reaction with the unsaturated double bond in the soft vinyl chloride resin or ethylene-vinyl alcohol copolymer. (ã) Soft vinyl chloride resin or ethylene-
Unsaturated double bond in vinyl alcohol copolymer [Effect of the invention] The soft vinyl chloride resin multilayer laminate thus obtained has
Without compromising toughness, flexibility, or transparency, there is almost no elution of plasticizers, which was a drawback in the past, and the outermost layer has excellent antithrombotic properties, making it an ideal solution for infusions, especially in the medical field. It can be widely used in blood circuits, catheters, etc., and is extremely useful. The effects of the present invention will be explained below with reference to Examples. Example 1 Vinyl chloride resin (SX-DH manufactured by Sumitomo Chemical Co., Ltd.)
To 100 parts by weight, 40 parts by weight of dioctyl phthalate, 0.03 parts by weight of each of a calcium-based stabilizer and a zinc-based stabilizer in terms of metal weight, and 10 parts by weight of epoxidized soybean oil were added, and rolled at 190°C for 7 minutes. The mixture was kneaded and then press-molded at 200°C for 3 minutes to obtain a sheet with a thickness of 1 m/m. On the other hand, ethylene
A vinyl alcohol copolymer (EVAL F manufactured by Kurera Co., Ltd.) was molded using a 30 m/mÏ extruder to obtain a film with a thickness of 50 ÎŒm. The above soft vinyl chloride resin sheet was cut into 10 cm square pieces, and the viscosity at 25°C was shown on the surface.
18000CS, and 10 mol% of trimethylsiloxane units are added to 100 parts by weight of dimethylpolysiloxane, which has dimethylvinylsilyl groups at both ends of the molecular chain.
Polysiloxane 5 consisting of 40 mol% dimethylsiloxane units and 50 mol% methylhydrogen siloxane units
Part by weight, 20 parts by weight of silica, and 0.2 parts by weight of an isopropyl alcohol solution of chloroplatinic acid (platinum content: 1%) were added to add an addition polymerization type liquid silicone rubber to a thickness of 50ÎŒ using a spacer for coating. Then, the above Eval film (cut into 10 cm squares) was placed on top of it (this is referred to as multilayer laminate A), and the above addition-polymerizable liquid silicone rubber was placed on top of the Eval film. Each layer coated with a thickness of 50 ÎŒm (this will be referred to as multilayer laminate B) was placed in an oven and heated at 100°C for 90 minutes to form two types of soft vinyl chloride resin multilayer laminates A and B. Obtained. Each of these multilayer laminates was strongly adhesively integrated. These multilayer laminates and the above-mentioned soft vinyl chloride resin sheet (comparative example) were each cut to a size of 7 cmÏ, and the soft chloride resin sheet of evaluation sheet 4 was placed on the back of the lid 2 of a metal container as shown in Figure 1. Set the container body 1 so that the vinyl resin layer is on the lid side.
(Capacity: 500ml) Pour 100ml of distilled water and cover with a lid.
The material was vibrated in the direction of arrow A for a certain period of time at 3 Hz in a constant temperature bath at 40° C. to extract the plasticizer, etc. Thereafter, each extract was taken out, and the amount of dioctyl phthalate in the solution was measured by gas chromatography. The results were as shown in Table 1.
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ãŠèŠ³å¯ãããçµæã第ïŒè¡šã«ç€ºããã[Table] Furthermore, in order to examine the antithrombotic properties of the outermost surface of these multilayer laminates and the surface of the soft vinyl chloride resin sheet (comparative example), each sheet was cut into 5 m/m square pieces, and each sheet was cut with the evaluation side facing up. Attach it to the bottom of a 50m/mÏ glass flat tray with double-sided adhesive tape, and pour 5ml of fresh dog blood from above.
After incubating at â for 4 minutes, blood was gently washed away with distilled water, treated with 1% glutaraldehyde aqueous solution for 2 hours, further washed with distilled water, air-dried, and the surface of each specimen was subjected to scanning electron microscopy. Observed at. The results are shown in Table 2.
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ã¿ã¬ãŒãã¯æº¶åºããŠããªãã€ãã[Table] As described above, the flexible vinyl chloride resin multilayer laminate of the present invention not only exhibits extremely low elution of plasticizers but also extremely low platelet adhesion, making it a particularly useful material in the medical field. I understand that. Example 2 50 parts by weight of dioctyl phthalate per 100 parts by weight of vinyl chloride resin (700-D manufactured by Toyosotatsu Co., Ltd.)
A molding compound was prepared by adding 0.03 parts by weight of each of a calcium-based stabilizer and a zinc-based stabilizer in terms of metal weight, and 5 parts by weight of epoxidized soybean oil. , outer diameter
A tube of 7m/m was created. This tube was cut into a length of approximately 2 m. On the other hand, for 100 parts by weight of dimethylpolysiloxane, which has a viscosity of 16000 cs at 25°C and has dimethylvinylsilyl groups at both ends of the molecular chain, 12 mol% of trimethylsiloxane units, 40 mol% of dimethylsiloxane units, and methylhydrogen siloxane units
35% by weight of an addition polymerization type liquid silicone rubber prepared by adding 7 parts by weight of polysiloxane consisting of 48 mol%, 25 parts by weight of silica, and 0.3 parts by weight of an isopropyl alcohol solution of chloroplatinic acid (platinum content: 5%).
Prepare an n-hexane solution, connect the approximately 2m tube mentioned above to a suction pump, and gently suction it. When the suction reaches almost the entire inner surface of the tube, remove it from the suction pump, leave the tube vertically, and remove it from the tube. After air-drying the solution until it no longer dripped, it was heated in a vertical dryer at 110° C. for 90 minutes. After that, the tube was taken out and ethylene-vinyl alcohol copolymer (EVAL E manufactured by Kuraray Co., Ltd.) was added.
was dissolved in a solvent of distilled water: isopropyl alcohol: n-propyl alcohol = 1:1:1.
A weight percent solution was prepared, and the inner surface of the tube was coated in the same manner as described above, followed by drying at 70° C. for 3 hours in a vertical vacuum dryer. The thus obtained multilayer laminated tube and the uncoated soft vinyl chloride resin tube (comparative example) were each connected to a blood pump, and physiological saline (48°C, 300 ml) was added at a rate of 100 ml/min. After circulating for 5 hours to extract the plasticizer, etc.
Each extract was analyzed by gas chromatography, and the amount of eluted dioctyl phthalate was determined. The results are shown in Table 3, showing that almost no dioctyl phthalate was eluted from the multilayer laminated tube of the present invention.
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FIG. 1 is a diagram showing a container used in the elution test of dioctyl phthalate.
Claims (1)
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æ³ã[Scope of Claims] 1. A flexible vinyl chloride resin multilayer laminate, comprising at least three layers of a flexible vinyl chloride resin, an ethylene-vinyl alcohol copolymer, and an addition-polymerized silicone rubber. 2 At least three layers constituting the laminate are soft vinyl chloride resin/addition polymerization silicone rubber/ethylene-vinyl alcohol copolymer, or soft vinyl chloride resin/addition polymerization silicone rubber/
The flexible vinyl chloride resin multilayer laminate according to claim 1, characterized in that ethylene-vinyl alcohol copolymer/addition polymerization type silicone rubber are laminated in this order. 3. Claim 1 or 2, wherein the metal in the stabilizer added to the soft vinyl chloride resin is one or more of calcium, zinc, barium, magnesium, and aluminum. 2. The soft vinyl chloride resin multilayer laminate according to item 2. 4. Organohydrogen containing two or more hydrogen atoms in one molecule of the addition-polymerizable silicone rubber in an amount sufficient to provide 1 to 6 hydrogen atoms directly bonded to silicon atoms per vinyl group in the composition. The soft vinyl chloride resin multilayer laminate according to claim 1 or 2, characterized in that it contains polysiloxane. 5. A patent characterized in that the ethylene-vinyl alcohol copolymer contains 0.01 to 5 parts by weight of organohydrogenpolysiloxane having at least 30 mol% of organohydrogensiloxane units based on 100 parts by weight of the resin. Claim 1 or 2
The soft vinyl chloride resin multilayer laminate described in Section 3. 6 Apply addition polymerization type liquid silicone rubber to the surface of a pre-formed soft vinyl chloride resin molded product, and contact the surface with a pre-formed ethylene-vinyl alcohol copolymer molded product, or further apply the ethylene-vinyl alcohol copolymer molded product to the surface. A method for producing a flexible vinyl chloride resin multilayer laminate, which comprises applying an addition-polymerizable liquid silicone rubber to the surface of a vinyl alcohol copolymer and heating it at 40°C to 130°C for 5 minutes to 10 hours. 7. Prepare a pre-formed soft vinyl chloride resin molded article, an organic solvent solution of addition polymerized liquid silicone rubber, and an organic solvent solution of ethylene-vinyl alcohol copolymer added with organohydrogen polysiloxane, and Apply
After curing by heating at 40°C to 130°C for 5 minutes to 10 hours, coat the layer and dry under reduced pressure at 40°C to 100°C, or further coat the surface of the ethylene-vinyl alcohol copolymer layer. A method for producing a soft vinyl chloride resin multilayer laminate, which comprises coating and heating at 40°C to 130°C for 5 minutes to 10 hours.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP18166684A JPS6161851A (en) | 1984-09-01 | 1984-09-01 | Vinyl chloride group resin multilayer laminate and manufacture thereof |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP18166684A JPS6161851A (en) | 1984-09-01 | 1984-09-01 | Vinyl chloride group resin multilayer laminate and manufacture thereof |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS6161851A JPS6161851A (en) | 1986-03-29 |
JPH0427940B2 true JPH0427940B2 (en) | 1992-05-13 |
Family
ID=16104742
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP18166684A Granted JPS6161851A (en) | 1984-09-01 | 1984-09-01 | Vinyl chloride group resin multilayer laminate and manufacture thereof |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS6161851A (en) |
-
1984
- 1984-09-01 JP JP18166684A patent/JPS6161851A/en active Granted
Also Published As
Publication number | Publication date |
---|---|
JPS6161851A (en) | 1986-03-29 |
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