WO2002000406A1 - Procede de production d'articles moules de silicone - Google Patents

Procede de production d'articles moules de silicone Download PDF

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Publication number
WO2002000406A1
WO2002000406A1 PCT/JP2001/005188 JP0105188W WO0200406A1 WO 2002000406 A1 WO2002000406 A1 WO 2002000406A1 JP 0105188 W JP0105188 W JP 0105188W WO 0200406 A1 WO0200406 A1 WO 0200406A1
Authority
WO
WIPO (PCT)
Prior art keywords
component
silicone
raw material
mixture
components
Prior art date
Application number
PCT/JP2001/005188
Other languages
English (en)
Japanese (ja)
Inventor
Akihiko Sano
Hiroo Maeda
Toshihiko Sugie
Original Assignee
Sumitomo Pharmaceuticals Company, Limited
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Sumitomo Pharmaceuticals Company, Limited filed Critical Sumitomo Pharmaceuticals Company, Limited
Priority to AU2001264314A priority Critical patent/AU2001264314A1/en
Publication of WO2002000406A1 publication Critical patent/WO2002000406A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
    • A61K9/0024—Solid, semi-solid or solidifying implants, which are implanted or injected in body tissue
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C48/00—Extrusion moulding, i.e. expressing the moulding material through a die or nozzle which imparts the desired form; Apparatus therefor
    • B29C48/16—Articles comprising two or more components, e.g. co-extruded layers
    • B29C48/18—Articles comprising two or more components, e.g. co-extruded layers the components being layers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/24—Crosslinking, e.g. vulcanising, of macromolecules
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C48/00—Extrusion moulding, i.e. expressing the moulding material through a die or nozzle which imparts the desired form; Apparatus therefor
    • B29C48/03—Extrusion moulding, i.e. expressing the moulding material through a die or nozzle which imparts the desired form; Apparatus therefor characterised by the shape of the extruded material at extrusion
    • B29C48/06—Rod-shaped
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2383/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen, or carbon only; Derivatives of such polymers
    • C08J2383/04—Polysiloxanes

Definitions

  • the present invention relates to a method for producing a molded product of silicone.
  • Moldings made of silicone are used in a wide variety of applications in a wide range of industrial fields, including electricity, electronics, architectural civil engineering, transportation equipment, the chemical industry, paper, textiles, food, and pharmaceuticals.
  • a two-component silicone rubber based on an addition-type curing reaction has been developed for a silicone composition (hereinafter referred to as a raw material silicone) used as a raw material for the production of a silicone molded product.
  • the curing reaction of the raw material silicone is classified into condensation-type curing and addition-type curing. It has useful characteristics such as being free from by-products and capable of promoting curing by heat.
  • the curing reaction is started by mixing the two components of the raw material silicone.
  • addition-type two-component silicone rubber for example, SILASTIC (registered trademark) Medical Grade ETR Elastomer is known, and a kit comprising two components of Part A and Part B is available. Provided. Examination of molded articles using such an addition-type two-component raw material silicone has been conducted. Specifically, for example, a long-term sustained-release preparation of a fat-soluble drug using silicone as a carrier (International Publication (WO) No. 00 / 159,199) has been proposed.
  • WO International Publication
  • Part A and Part B One component and the other component (each component will be referred to as Part A and Part B hereinafter) of a two-component silicone raw material of a mold, and a solid consisting of a fat-soluble drug and a water-soluble substance simultaneously mixed and molded.
  • Part A and Part B One component and the other component (each component will be referred to as Part A and Part B hereinafter) of a two-component silicone raw material of a mold, and a solid consisting of a fat-soluble drug and a water-soluble substance simultaneously mixed and molded.
  • Japanese Patent Application Laid-Open Publication No. 187,974 / 1995 proposes a controlled-release drug formulation, in which the raw material silicone part A and the drug, and the raw material silicone part B and the drug are separately mixed.
  • a method for producing a preparation by mixing and molding the respective mixtures is exemplified. In this production method, curing starts when a mixture of one part of each raw material silicone and the drug and a mixture of the other part and the drug are mixed, and one part of the raw material silicone and the drug are mixed. May be able to be stored if it is in the form of a mixture.
  • the problem to be solved by the present invention is to establish a mass production method which is not restricted by the curing reaction of the raw material silicon in the production of molded silicone products.
  • the present inventors have conducted intensive studies to solve the above problems, and as a result, have found that In the production of silicone moldings made of raw silicone, a large amount of silicone moldings that are not subject to manufacturing restrictions due to the curing reaction of the raw silicone by devising methods of mixing and molding the two components that make up the raw silicone. I found a production method. In addition, in the production of a silicone molded product composed of an addition-type two-component raw material silicone and an additive component, a method of mixing and molding the addition-type two-component raw material silicone and the additional component is devised. We have found a method for mass-producing silicone molded articles containing additional components that are not subject to manufacturing restrictions due to the curing reaction of the silicone. That is, the present invention relates to the following.
  • a method of producing a silicone molded product using an addition type two-component raw material silicone in which one component and the other component of the original silicone are continuously supplied to a mixing device. Mixing and subsequent molding are performed continuously.
  • [2] A method for producing a silicone molded product using an addition type two-component raw material silicone, wherein one component of the raw material silicone, the other component, and each of the additional components are continuously mixed.
  • One or more additional components are mixed in advance with both components of the addition-type two-component raw material silicone, and a mixture of one component of the premixed raw material silicone and the additional component is added.
  • the method according to [3], wherein the composition and content of the additional components in the mixture are the same as the composition and content of the additional components in the mixture of the other components and the additional components of the raw material silicone previously mixed.
  • the content of the additive component in the mixture of one of the pre-mixed raw material silicone and the additive component and the content of the additive component in the mixture of the other component of the pre-mixed raw silicone and the additive component The method according to [4], wherein the content of one of the components is 90% to 110% of the content of the other component when compared with the content of the additional component.
  • the silicone molded product is a medical preparation for human or animal use [2]
  • the raw material silicone used as a raw material in the present invention may be an addition type two-component raw material silicone, and is appropriately selected depending on the use of a silicone molded product and a molding method.
  • the addition type raw material silicone include (1) an organopolysiloxane containing a functional group having an aliphatic unsaturated bond, and (2) a hydrogen organopolysiloxane (a relatively low-molecular-weight organopolysiloxane having a Si—H bond in a molecule).
  • (1) to (4) are cured by crosslinking by a hydrosilylation reaction, (1) is a main ingredient, (2) is a crosslinking agent, (3) is a curing catalyst,
  • two-component raw material silicone two types are prepared by appropriately combining and blending them (these two types of mixture are referred to as two-component raw material silicones).
  • the blending of each of the two components here (each corresponding to Part A and Part B) is designed such that the hardening reaction starts when the two components are mixed.
  • the characteristics of the additional mold are that the surface and the inside of the molded product are uniformly cured, so-called deep-curing property, that there is essentially no by-product during curing, and that it can be cured in a short time by heating. With advantages such as. Also, by selecting the types and amounts of the above (3) and (4), curing conditions such as desired time and temperature can be set.
  • the raw material when using an existing raw material silicone, the raw material can be used. It must be used within certain conditions specific to silicone.
  • examples of commercially available addition-type two-component raw material silicone include Dow Corning's SILASTIC (registered trademark).
  • SILASTIC registered trademark
  • Additives are to be included in the silicone moldings to be manufactured.
  • examples include those that improve the function of silicone moldings, those that prevent deterioration, and those that exert their functions when released from silicone moldings. Is done.
  • the additive component may be a liquid, a solid, or an oil as long as it does not extremely inhibit the curing of the silicone so that molding cannot be performed, and does not have such a content that molding is impossible.
  • examples of compounds that inhibit curing include amines and nitric oxide compounds. Care must be exercised when adding them as additional components.
  • the additive component contained in the silicone molded product may be one kind or two or more kinds.
  • the additive to be mixed with Part A and the additive to be mixed with Part B may have the same composition or different compositions.
  • the preferred method is appropriately determined according to the composition of the additive component in the silicone molded product to be produced.
  • the amount of the additional components in Part A and the amount of the additional components in Part B may be within a range that allows molding and processing. Even if the deviation is zero, it is also included in the scope of the manufacturing method of this effort.
  • part A and part B, or part A, part B and additive components, or a mixture of part A and additive components and a mixture of part B and additive components are continuously supplied to a mixing device.
  • mixing and subsequent molding are performed continuously.
  • a method of continuously feeding a fixed amount of Part A and a fixed amount of Part B to a mixing device, mixing the raw material silicone components fed in, and taking out the mixture at a constant speed. can give.
  • a certain amount of Part A, a certain amount of Part B, and a certain amount of additive components were continuously fed into a mixing device and fed.
  • each raw material silicone component and additive component are mixed, and the mixture is taken out at a constant speed.
  • a mixing method in the production of a silicone molded article containing an additional component a fixed amount of a mixture of Part A and the additional component (hereinafter, referred to as mixture A) and a mixture of Part B and the additional component (hereinafter, referred to as “mixture A”)
  • Mixing B) A method of feeding each mixture to a mixing device, mixing the fed mixtures, and taking out the mixture at a constant speed.
  • the fixed amount of the mixture A and the fixed amount of the mixture B may be the same amount or may be different amounts, but the fixed amount of the mixture A and the fixed amount of the mixture B sent to the mixing apparatus are different. Variations in the ratio during the manufacturing process generally have an adverse effect on the uniformity of the silicone molding.
  • the present inventors further supply one component and the other component of the addition-type two-component raw material silicone and each of the additional components to a mixing device continuously, and perform mixing and subsequent molding. In continuous operation, one or more additional components are mixed in advance with both components of the addition-type two-component raw material silicone, and one component of the pre-mixed raw material silicone is mixed with one component.
  • silicone molded products that require strict uniformity of the content of added components such as pharmaceuticals are a major problem in process control.
  • the method of the present invention is an effective solution to this problem.
  • the composition and content uniformity of each additive component in the silicone molded product are affected by slight fluctuations in the supply amounts of the mixture A and the mixture B to the mixing device.
  • This is a very excellent manufacturing method in terms of process control.
  • mixture A and mixture B do not cure until they are mixed, so they can be mixed for a sufficient amount of time, and sampling has been performed to confirm the uniformity of mixture for each of mixture A and mixture B.
  • It is also a very easy to control process in that the process of mixing, molding and curing of mixture A and mixture B can be performed after that.
  • composition and content of the additional component in the mixture of one component of the pre-mixed raw material silicone and the additional component (corresponding to the above mixture A), and the other component and the additional component of the pre-mixed raw material silicone If the composition and content of the additional components in the mixture (corresponding to the above mixture B) are the same, specific examples of the addition of the components are, for example, for each of the additional components, the content in the mixture A and the mixture.
  • one content is 90% to 110%, preferably 95% to 105%, more preferably 98% to 10% with respect to the other content. 2%.
  • the term “additional components having the same composition and content” or “for each of the added components” means that all the components are included.
  • the components which do not essentially affect the quality of the silicone molded product do not need to be “the same in composition and content”, and do not need to be within the above-mentioned content range.
  • the silicone molded product is a medical preparation
  • the contents of the mixture A and the mixture B within the above range do not essentially affect the content or release of the preparation.
  • Components that do not affect the content or release of the preparation include, for example, components for adjusting the curing rate and drug stabilizers. If such components are present in small amounts (e.g.
  • the resulting mixture comprising Part A and Part B, or the mixture comprising Part A, Part B and additional components, is then continuously molded into a molded product.
  • the molding method uses standard methods such as compression molding, transfer molding, injection molding, and extrusion molding. More molded.
  • a twin-screw extruder is an example of an apparatus that continuously mixes raw silicone parts A and B, or parts A and B and added components, or mixture A and mixture B.
  • TEX series and Lavoulder manufactured by Nippon Steel Works Co., Ltd., CO NVER TWIN—BT series manufactured by Plastic Engineering Laboratory are commercially available, and such devices can be used.
  • a twin-screw is rotated in a cylinder, and the input material input from the upstream material input port is sent out downstream while being mixed by the rotating screw. The raw material is discharged from the downstream outlet in a completely mixed state.
  • the die is the die part of the extruder where the material is extruded and the shape of the extruded material is formed
  • the extruder of the twin-screw extruder is extruded. Molding can also be performed using pressure.
  • the raw material silicone used as the raw material is an addition-type two-component raw material silicone, and basically, the mixing process of the two components and the temperature and time after the mixing affect the curing rate. For this reason, the mixing process of Part A and Part B, or Part A, Part B and additive ingredients, or Mixture A and Mixture B
  • the temperature during the mixing process is preferably 60 ° C or less, and more preferably room temperature (45 ° C or less). It is.
  • the time allowed from mixing to molding depends on the mixing temperature and should be shorter at higher temperatures, but should be shorter than one hour, preferably within 30 minutes, and more preferably within a few minutes.
  • SILASTIC registered trademark Medical Grade ETR Elastomer Q7—4750 is an example.
  • the mixture is molded within 80 minutes at 80 ° C. However, at 20 ° C, about 3 hours are allowed. The molded product obtained by the above molding is then cured.
  • the temperature and time for curing depend on the properties of the raw material silicone used and the physical properties (such as stability) of the added components.
  • SILASTIC registered trademark
  • Medical Grade ETR Elastomer Q 7-4 Preference for 750, for example, 1 16 ° C for 10 minutes, or 50 ° C for 1 week after mixing Part A and Part B.
  • the silicone molded product or the silicone molded product containing the additive component is not particularly limited as long as it can be produced by the production method of the present invention.
  • it may be a medical preparation for human or animal use, a base material for an external preparation, an external preparation sheet for releasing a pharmaceutically acceptable physiologically active substance as an additional component, an injection, an implant in a living body.
  • the present invention can be used for the production of a silicone molded product containing an additive component.
  • the selection of the additive component is made according to the silicone molded product containing the additive component to be produced.
  • pharmaceutical preparations include pharmaceutically acceptable physiologically active substances and pharmaceutical additives, and pharmaceutically acceptable physiologically active substances and pharmaceuticals that are used in vivo in medical devices. It may be an additive.
  • the pharmaceutically acceptable bioactive substance here may be not only a substance having a direct therapeutic effect but also a substance showing a bioactivity or a substance which assists or induces a bioactivity.
  • Proteinaceous substances, genes, vaccines and adjuvants thereof are examples of pharmaceutically acceptable bioactive substances.
  • it can be used as a display component for safety at night in automobile and bicycle parts by using a fluorescent substance or a dye as an additive component.
  • silicone moldings containing additional components include: A columnar inner layer containing a certain pharmaceutically acceptable physiologically active substance in a silicone carrier, and a formulation in which the inner layer is covered with an outer layer made of silicone, and both ends of the inner layer are open so as to be in direct contact with the external environment.
  • the following is an example of the manufacturing method for a concentric preparation. This concentric product uses two twin-screw extruders, and the two devices are used at the discharge / exit portion of each device to produce a concentric product die (a material is extruded and the shape of the extruded material is extruded).
  • the mixture that forms the inner layer and the mixture that forms the outer layer are extruded from separate twin-screw extruders and are formed so as to be concentrically formed. It can be manufactured by assembling and using the equipment system connected by (). That is, a mixture of Part A and the additive component and a mixture of Part B and the additive component are prepared, and are continuously charged from the material input port of the twin-screw extruder. On the other hand, Part A and Part B are continuously fed from the raw material inlet of the other twin screw extruder.
  • FIG. 1 is a diagram showing one embodiment of the production method of the present invention.
  • Example 1 is provided to further clarify the present invention, but the scope of the present invention is not limited to these examples.
  • Example 1 is provided to further clarify the present invention, but the scope of the present invention is not limited to these examples.
  • 500 g of ivermectin powder, 334 g of sodium desoxycholate powder and 166 g of sucrose powder are mixed vigorously with a mixer to obtain a drug mixed powder as an additional component.
  • 500 g of half of 100 g of the obtained additive component and (SI LAST IC, registered trademark) Medical Grade ETR Elastomer Q 7-47 50 Part A 1 166 g is mixed with a pressurized kneader to obtain Part A containing additional ingredients.
  • 500 g of the added ingredient and SI LASTIC (registered trademark) Medical Grade ETR Elastomer Q 7-4750 Part B 1166 g are mixed with a pressurized kneader to remove the Part B containing the added ingredient. Get. Confirm the contents of ivermectin, sodium desoxyconoleate, and sucrose in the obtained Part A and Part: B.
  • Part A containing the additive obtained by the above method was loaded into one of the input devices at the two material input ports provided in the twin-screw extruder, and obtained by the above method into the other input device.
  • Load Part B containing the additional ingredients was loaded into one of the input devices at the two material input ports provided in the twin-screw extruder, and obtained by the above method into the other input device.
  • Load Part B containing the additional ingredients is started in conjunction with each other.
  • a series of mixing and extruding is performed, and the extruded rod is conveyed by a conveyor.
  • the outlet is made circular with a diameter of 2.9 mm, the operation is performed at an extrusion speed of 1 m / min, and a rod of 420 m is obtained in 7 hours.
  • the jaws conveyed by the conveyor are cut by a cutting machine every 1 m, heat-treated in a constant temperature machine at 50 ° C for 1 week, cured, and then cut by a cutting machine every 30 mm.
  • Example 2 '
  • a twin-screw extruder (for inner layer) loaded with part A containing the additional ingredients and part B containing the additional ingredients, as well as a silastic (SI LAST IC®) medical grade ETR Elastomer Q7— 4750 Part A 2000 g and Part B 2 ⁇ Twin screw extruder loaded with 00 g (for outer layer)
  • the mixture (components from the twin-screw extruder for the inner layer) is contained in the inner layer. (Component from the extruder) is placed in the outer layer. Then, the screws of the two twin-screw extruders, the four feeding devices, and the conveyer for the feeder adjacent to the die are started in conjunction with each other to perform a series of mixing and extrusion.
  • the inside diameter of the nozzle of the die at the discharge port was a circle with a diameter of 2.9 mm
  • the extrusion speed was lm / min
  • each of the inner layer twin screw extruder and the outer layer twin screw extruder was used.
  • the operation is performed so that the discharge of the mixture becomes 7: 3, and the operation is stopped when the parts A and B containing the added components are no longer loaded into the twin-screw extruder for the inner layer. .
  • the rod conveyed by the conveyor is cut by a cutting machine every 1 m, heat-treated by a constant temperature machine at 50 ° C for 1 week, cured, and then cut by a cutting machine every 30 mm to form a column.
  • the raw material silicone or raw material silicone was added to the raw material.
  • the production method of the present invention characterized in that each of the components is continuously supplied to a mixing apparatus, and mixing and subsequent molding are continuously performed, is continuously performed without restrictions due to curing of the raw material silicone. Therefore, it is possible to mass-produce long-term mixed-synthesis type production.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Medicinal Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Mechanical Engineering (AREA)
  • Dermatology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Processing And Handling Of Plastics And Other Materials For Molding In General (AREA)

Abstract

L'invention porte sur un procédé de production d'articles moulés de silicone utilisant un additif au composant de silicone, et selon lequel le composant de silicone et l'autre composant alimentent en continu un mélangeur, puis sont mélangés en continu, puis sont moulés, ce qui permet une production massive d'articles moulés de silicone exempte des restrictions dues à la réaction de durcissement du silicone.
PCT/JP2001/005188 2000-06-26 2001-06-18 Procede de production d'articles moules de silicone WO2002000406A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2001264314A AU2001264314A1 (en) 2000-06-26 2001-06-18 Production method for silicone molded product

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2000-190585 2000-06-26
JP2000190585 2000-06-26

Publications (1)

Publication Number Publication Date
WO2002000406A1 true WO2002000406A1 (fr) 2002-01-03

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PCT/JP2001/005188 WO2002000406A1 (fr) 2000-06-26 2001-06-18 Procede de production d'articles moules de silicone

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1449565A1 (fr) 2003-02-21 2004-08-25 Honeywell Normalair-Garrett (Holdings) Limited Méthode de test
CN112877028A (zh) * 2021-01-14 2021-06-01 江西欧普特实业有限公司 一种加成型有机硅灌封胶及其制备方法

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6078920A (ja) * 1983-10-04 1985-05-04 Nippon Kayaku Co Ltd シリコンゴム製剤
JPS6129521A (ja) * 1984-07-19 1986-02-10 Toshiba Silicone Co Ltd シリコ−ンゴム成形体とその製造方法
US4783289A (en) * 1986-04-01 1988-11-08 Toray Silicone Co., Ltd. Process for molding silicone rubber compositions
US5371162A (en) * 1992-07-09 1994-12-06 Minnesota Mining And Manufacturing Company Storage-stable silicone composition

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6078920A (ja) * 1983-10-04 1985-05-04 Nippon Kayaku Co Ltd シリコンゴム製剤
JPS6129521A (ja) * 1984-07-19 1986-02-10 Toshiba Silicone Co Ltd シリコ−ンゴム成形体とその製造方法
US4783289A (en) * 1986-04-01 1988-11-08 Toray Silicone Co., Ltd. Process for molding silicone rubber compositions
US5371162A (en) * 1992-07-09 1994-12-06 Minnesota Mining And Manufacturing Company Storage-stable silicone composition

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1449565A1 (fr) 2003-02-21 2004-08-25 Honeywell Normalair-Garrett (Holdings) Limited Méthode de test
CN112877028A (zh) * 2021-01-14 2021-06-01 江西欧普特实业有限公司 一种加成型有机硅灌封胶及其制备方法

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