EP0733085A1 - Peroxide-crosslinkable, low-hardness, fluorine rubber composition - Google Patents
Peroxide-crosslinkable, low-hardness, fluorine rubber compositionInfo
- Publication number
- EP0733085A1 EP0733085A1 EP95904842A EP95904842A EP0733085A1 EP 0733085 A1 EP0733085 A1 EP 0733085A1 EP 95904842 A EP95904842 A EP 95904842A EP 95904842 A EP95904842 A EP 95904842A EP 0733085 A1 EP0733085 A1 EP 0733085A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- weight
- fluoroelastomer
- parts
- peroxide
- hardness
- 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.)
- Withdrawn
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0025—Crosslinking or vulcanising agents; including accelerators
Definitions
- the present invention relates to a novel vulcanization composition containing a fluoroelastomer. More specifically, the present invention is directed to a peroxide-vulcanizable fluoroelastomer composition which permits achievement of low hardness and excellent chemical resistance. BACKGROUND OF THE INVENTION
- Fluoroelastomers have excellent heat resistance and oil resistance. Therefore, they are used for O-rings, gaskets, oil seals, diaphragms, hoses, rolls, sheet materials, and the like in a variety of industrial fields, such as those involving automobiles, ships, aircraft, and hydraulic devices; the chemical industry and general appliances industry; and pollution-related fields.
- Peroxide-vulcanizable fluoroelastomer products have exceptional acid and chemical resistance and are used for office equipment, in the fields of medical drugs and medical treatment, and in food product-related applications. Peroxide-vulcanized fluoroelastomer products having a low degree of hardness are desirable for applications which require acid or chemical resistance as well as good sealing properties with low tightening force in glass or plastic vessels. However, there are no examples of any such products which are satisfactory in terms of practical performance with a hardness of 50 or less.
- the present invention is a peroxide-vulcanizable fluoroelastomer composition which allows a molded article with a hardness of 50 or less to be obtained, which composition comprises a) a peroxide-vulcanizable bromine-containing fluoroelastomer or iodine-containing fluoroelastomer, said fluoroelastomer having i) at least 20% by weight of a fraction having molecular weight of no more than 50,000, and ii) no more than 1% by weight of a fraction having molecular weight of 1,000,000 or more; b) 0.1 to 5 parts by weight of an organic peroxide per 100 parts by weight of a); and c) 0.1 to 5 parts by weight of a poly functional co-crosslinker per 100 parts by weight of a).
- the present invention provides a peroxide-vulcanizable fluoroelastomer composition which permits a molded article with a hardness of 50 or less to be obtained without impairing the kneading workability and without sacrificing the heat resistance, oil resistance, acid resistance, and chemical resistance which are characteristic of conventional peroxide-vulcanizable fluoroelastomers.
- component a) of the present invention examples include binary copolymers having interpolymerized units of vinylidene fluoride (VDF) and hexafluoropropylene (HFP), or ternary copolymers having interpolymerized units of VDF, HFP, and tetrafluoroethylene (TFE), either of which copolymers contain bromine and/or iodine in the polymer chain or polymer terminals.
- VDF vinylidene fluoride
- HFP hexafluoropropylene
- TFE tetrafluoroethylene
- binary and ternary refer to principal constituent monomers which do not include interpolymerized units of bromine-containing or iodine-containing monomers.
- Component b) of the present invention is an organic peroxide that produces peroxide radicals at the vulcanization temperature, for example, t-butyl cumyl peroxide, dicumyl peroxide, 2,5-dimethyl-2,5- di-(t-butylperoxy) hexane, and 2,5-dimethyl-2,5-2,5-di-(t-butylperoxy) hexane-3.
- Component c) is a polyfunctional co-crosslinker.
- Examples of component c) of the present invention include triallylcyanurate, triallylisocyanurate, and trimethallylisocyanurate.
- the ratio in which component b) is used is 0.1 to 5 parts by weight, and preferably 0.3 to 3 parts by weight, per 100 parts by weight of component a) of the present invention.
- Component c) is used in a ratio of 0.1 to 5 parts by weight, and preferably 0.3 to 3 parts by weight per 100 parts by weight of component a).
- Use of less than 0.1 weight part of component b) does not permit the necessary degree of crosslinking to be achieved, whereas an amount in excess of 5 parts by weight does not permit a hardness of 50 or less to be achieved.
- Use of less than 0.1 parts by weight of component c) does not allow the necessary degree of crosslinking to be achieved, whereas an amount in excess of 5 weight parts makes it difficult to achieve a hardness of 50 or less.
- the molecular weight distribution of component a) is stipulated within the aforementioned range because less than 20% by weight of the M50 fraction does not allow a hardness of 50 or less to be achieved. Similarly, more than 1% by weight of the Ml 000 fraction also does not allow a hardness of 50 or less to be achieved.
- Other components such as carbon black, Austin black, graphite, silica, clay, diatomaceous earth, talc, calcium carbonate, calcium silicate, calcium sulfate, fatty acid calcium, fatty acid amides, low molecular weight polyethylene, silicone oil, silicone grease, metal soap, stearic acid, fatty amines, titanium oxide, red iron oxide, and other such fillers, working adjuvants, plasticizers, coloring agents, and the like can be blended as needed into the fluoroelastomer composition of the present invention.
- Acid-absorbers such as magnesium oxide, zinc oxide, calcium oxide, and calcium hydroxide, may also be added.
- Methods for vulcanizing the fluoroelastomer composition thus obtained include methods in which the material is kneaded using an open-type mixing roll or closed-type kneading roll (such as a Banbury mixer or a pressure kneader), and the material is then introduced into a heated mold and compressed to effect primary vulcanization, followed by secondary vulcanization.
- an open-type mixing roll or closed-type kneading roll such as a Banbury mixer or a pressure kneader
- the conditions for the primary vulcanization include a temperature of 120° to 200°C, a time of 1 to 80 minutes, and a pressure of 20 to 150 kg/cm 2
- the conditions for the secondary vulcanization include a temperature of 120° to 250°C, and a time of 0 to 48 hours.
- Other vulcanization means which can be used include methods in which a preform is fashioned by injection or extrusion or the like, followed by vulcanization, or methods in which one or more ketones, ethers, or the like are used as media to prepare a solution or dispersion, which is then used to coat the surface of paper, fiber, film, sheets, plates, tubes, pipes, tanks, large-scale containers, or other molded articles, followed by vulcanization.
- Liquid chromatograph model LC-3A (Shimadzu Seisakusho) Columns: KF-80 M (two) & KF-800 P (precolumn) (Showa Denko) Detector: ERC-7510 S (Elmer Optical)
- Polymer serving as standard for molecular weight detection lines various types of monodisperse polystyrene (Toyo Soda) Concentration: 0.1 wt%
- Fluoroelastomer FR-6150 (100 parts by weight, 34% by weignt M50 fraction and 0% Ml 000 fraction) manufactured by Asahi Chemical Industry (64.4 mol% VDF, 18.2 mol% HFP, 17.4 mol% TFE, 68.0 wt% F content, and 5200 ppm I content) was wound on an open-type mixing roll. Carbon black (3 parts by weight, Thermax N-990 from Cancarb), 1 part by weight lead oxide (Litharge No.
- Example 2 Vulcanized molded material was prepared in the same manner as in Example 1 except that the amount of Perhexa 2,5 B used was 1 part by weight and the amount of TAIC used was 2 parts by weight. The various tests were conducted, and the results are shown in Table 1.
- Example 3 Vulcanized molded material was prepared in the same manner as in Example 1 except that the amount of Perhexa 2,5 B used was 1.5 parts by weight and the amount of TAIC used was 3 parts by weight. The various tests were conducted, and the results are shown in Table 1.
- Comparative Example 1 Vulcanized molded material was prepared in the same manner as in Example 1 except that the FR-6150 was replaced by FR-6350 (containing 13% M50 and 0% M1000) by Asahi Chemical Industry (64.4 mol% VDF, 18.2 mol % HFP, 17.4 mol % TFE, 68.0% F content, and 3000 ppm I content). The various tests were conducted. The results are shown in Table 1.
- Comparative Example 2 Vulcanized molded material was prepared in the same manner as in Example 1 except that the FR-6150 was replaced by G-902 (containing 21% M50 and 1.5% Ml 000) by Daikin Industries (54.7 mol% VDF, 23.6 mol% HFP, 21.7 mol% TFE, 69.7% F content, and 2200 ppm I content). The various tests were conducted. The results are shown in Table 1.
- Vulcanizability (g). 160°C Optimal time (min) 10.8 11.0 11.5 12.5 11.8
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP30657493A JPH07196878A (ja) | 1993-12-07 | 1993-12-07 | パーオキサイド架橋可能な低硬度フッ素ゴム加硫組成物 |
JP306574/93 | 1993-12-07 | ||
PCT/US1994/014093 WO1995015995A1 (en) | 1993-12-07 | 1994-12-06 | Peroxide-crosslinkable, low-hardness, fluorine rubber composition |
Publications (1)
Publication Number | Publication Date |
---|---|
EP0733085A1 true EP0733085A1 (en) | 1996-09-25 |
Family
ID=17958702
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP95904842A Withdrawn EP0733085A1 (en) | 1993-12-07 | 1994-12-06 | Peroxide-crosslinkable, low-hardness, fluorine rubber composition |
Country Status (3)
Country | Link |
---|---|
EP (1) | EP0733085A1 (it) |
JP (1) | JPH07196878A (it) |
WO (1) | WO1995015995A1 (it) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2805705A1 (en) | 2013-05-23 | 2014-11-26 | IP Gesellschaft für Management mbH | Packaging with one or more administration units comprising a sodium salt of (R)-3-[6-amino-pyridin-3-yl]-2-(1-cyclohexyl-1 H-imidazol-4-yl)-propionic acid |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR100501991B1 (ko) * | 1997-04-15 | 2005-07-18 | 다이낑 고오교 가부시키가이샤 | 불소고무 가황용 조성물 및 불소고무 성형품 |
EP1227134B1 (en) * | 1999-08-31 | 2006-10-04 | Daikin Industries, Ltd. | Polymer composition crosslinkable with ultraviolet |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BR8902092A (pt) * | 1988-05-06 | 1989-12-05 | Du Pont | Composicao de fluorelastomero |
CA2103677A1 (en) * | 1992-05-11 | 1993-11-12 | Michio Kasahara | Fluorine-containing elastomer composition and molded articles made therefrom |
-
1993
- 1993-12-07 JP JP30657493A patent/JPH07196878A/ja active Pending
-
1994
- 1994-12-06 EP EP95904842A patent/EP0733085A1/en not_active Withdrawn
- 1994-12-06 WO PCT/US1994/014093 patent/WO1995015995A1/en not_active Application Discontinuation
Non-Patent Citations (1)
Title |
---|
See references of WO9515995A1 * |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2805705A1 (en) | 2013-05-23 | 2014-11-26 | IP Gesellschaft für Management mbH | Packaging with one or more administration units comprising a sodium salt of (R)-3-[6-amino-pyridin-3-yl]-2-(1-cyclohexyl-1 H-imidazol-4-yl)-propionic acid |
EP3184095A1 (en) | 2013-05-23 | 2017-06-28 | IP Gesellschaft für Management mbH | Administration units comprising polymorph 1 of 2-(2-methylamino-pyrimidin-4-yl]-1h-indole-5-carboxylic acid [(s)-1-carbamoyl-2-(phenyl-pyrimidin-2-yl-amino)-ethyl]-amide |
Also Published As
Publication number | Publication date |
---|---|
WO1995015995A1 (en) | 1995-06-15 |
JPH07196878A (ja) | 1995-08-01 |
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Legal Events
Date | Code | Title | Description |
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PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
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17P | Request for examination filed |
Effective date: 19960515 |
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AK | Designated contracting states |
Kind code of ref document: A1 Designated state(s): DE FR GB IT |
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17Q | First examination report despatched |
Effective date: 19970723 |
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STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE APPLICATION HAS BEEN WITHDRAWN |
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18W | Application withdrawn |
Withdrawal date: 19971126 |