WO1986004596A1 - Fluorocarbon polymers possessing filler materials - Google Patents
Fluorocarbon polymers possessing filler materials Download PDFInfo
- Publication number
- WO1986004596A1 WO1986004596A1 PCT/DE1986/000029 DE8600029W WO8604596A1 WO 1986004596 A1 WO1986004596 A1 WO 1986004596A1 DE 8600029 W DE8600029 W DE 8600029W WO 8604596 A1 WO8604596 A1 WO 8604596A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- polymers
- titanate
- fluorocarbon polymers
- fluorocarbon
- filler materials
- Prior art date
Links
- 229920002313 fluoropolymer Polymers 0.000 title claims abstract description 18
- 239000000945 filler Substances 0.000 title claims abstract description 11
- 239000000463 material Substances 0.000 title abstract description 17
- 229920000642 polymer Polymers 0.000 claims abstract description 18
- 229920001577 copolymer Polymers 0.000 claims abstract description 5
- 229920001169 thermoplastic Polymers 0.000 claims abstract description 3
- 239000004416 thermosoftening plastic Substances 0.000 claims abstract description 3
- 239000006260 foam Substances 0.000 abstract description 2
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 230000008018 melting Effects 0.000 abstract 1
- 238000002844 melting Methods 0.000 abstract 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 17
- 239000000155 melt Substances 0.000 description 10
- -1 hexafluoroethylene Chemical class 0.000 description 9
- 229920000840 ethylene tetrafluoroethylene copolymer Polymers 0.000 description 8
- 239000004033 plastic Substances 0.000 description 7
- 229920003023 plastic Polymers 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 4
- 239000003365 glass fiber Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000004604 Blowing Agent Substances 0.000 description 3
- 239000004812 Fluorinated ethylene propylene Substances 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000001125 extrusion Methods 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000001746 injection moulding Methods 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 229920009441 perflouroethylene propylene Polymers 0.000 description 3
- 229920001780 ECTFE Polymers 0.000 description 2
- 229920001774 Perfluoroether Chemical class 0.000 description 2
- UMHKOAYRTRADAT-UHFFFAOYSA-N [hydroxy(octoxy)phosphoryl] octyl hydrogen phosphate Chemical compound CCCCCCCCOP(O)(=O)OP(O)(=O)OCCCCCCCC UMHKOAYRTRADAT-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000013329 compounding Methods 0.000 description 2
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 2
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000002557 mineral fiber Substances 0.000 description 2
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- KTXWGMUMDPYXNN-UHFFFAOYSA-N 2-ethylhexan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCCC(CC)C[O-].CCCCC(CC)C[O-].CCCCC(CC)C[O-].CCCCC(CC)C[O-] KTXWGMUMDPYXNN-UHFFFAOYSA-N 0.000 description 1
- 239000004156 Azodicarbonamide Substances 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 239000002033 PVDF binder Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- KOEFSMLBFZGZLD-UHFFFAOYSA-L [bis(2-ethylhexoxy)-oxidophosphaniumyl] dihydrogen phosphate [bis(2-ethylhexoxy)-oxidophosphaniumyl] phosphate ethane-1,2-diolate titanium(4+) Chemical compound [Ti+4].[O-]CC[O-].CCCCC(CC)CO[P+]([O-])(OCC(CC)CCCC)OP(O)(O)=O.CCCCC(CC)CO[P+]([O-])(OCC(CC)CCCC)OP([O-])([O-])=O KOEFSMLBFZGZLD-UHFFFAOYSA-L 0.000 description 1
- GUIYQMUJNFJGAD-UHFFFAOYSA-L [butoxy(methoxy)phosphoryl] phosphate;ethane-1,2-diolate;hydron;titanium(4+) Chemical compound [H+].[H+].[Ti+4].[O-]CC[O-].CCCCOP(=O)(OC)OP([O-])([O-])=O.CCCCOP(=O)(OC)OP([O-])([O-])=O GUIYQMUJNFJGAD-UHFFFAOYSA-L 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- XOZUGNYVDXMRKW-AATRIKPKSA-N azodicarbonamide Chemical compound NC(=O)\N=N\C(N)=O XOZUGNYVDXMRKW-AATRIKPKSA-N 0.000 description 1
- 235000019399 azodicarbonamide Nutrition 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 238000010382 chemical cross-linking Methods 0.000 description 1
- HTDKEJXHILZNPP-UHFFFAOYSA-N dioctyl hydrogen phosphate Chemical compound CCCCCCCCOP(O)(=O)OCCCCCCCC HTDKEJXHILZNPP-UHFFFAOYSA-N 0.000 description 1
- XMQYIPNJVLNWOE-UHFFFAOYSA-N dioctyl hydrogen phosphite Chemical compound CCCCCCCCOP(O)OCCCCCCCC XMQYIPNJVLNWOE-UHFFFAOYSA-N 0.000 description 1
- VTIXMGZYGRZMAW-UHFFFAOYSA-N ditridecyl hydrogen phosphite Chemical compound CCCCCCCCCCCCCOP(O)OCCCCCCCCCCCCC VTIXMGZYGRZMAW-UHFFFAOYSA-N 0.000 description 1
- XHWQYYPUYFYELO-UHFFFAOYSA-N ditridecyl phosphite Chemical compound CCCCCCCCCCCCCOP([O-])OCCCCCCCCCCCCC XHWQYYPUYFYELO-UHFFFAOYSA-N 0.000 description 1
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000004428 fluoroalkoxy group Chemical group 0.000 description 1
- XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical compound FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 238000009533 lab test Methods 0.000 description 1
- 238000011545 laboratory measurement Methods 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- MCCIMQKMMBVWHO-UHFFFAOYSA-N octadecanoic acid;titanium Chemical compound [Ti].CCCCCCCCCCCCCCCCCC(O)=O.CCCCCCCCCCCCCCCCCC(O)=O.CCCCCCCCCCCCCCCCCC(O)=O.CCCCCCCCCCCCCCCCCC(O)=O MCCIMQKMMBVWHO-UHFFFAOYSA-N 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920005574 polyvinylidene vinyl fluoride Polymers 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical group [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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
- C08K5/04—Oxygen-containing compounds
- C08K5/05—Alcohols; Metal alcoholates
- C08K5/057—Metal alcoholates
Definitions
- the present invention relates to fluorocarbon polymers which contain organic titanates as fillers.
- Fluorocarbon polymers are being used to an increasing extent as materials with desired, selectively adjustable properties.
- fluorocarbon polymers can be simple polyfluorocarbons such as e.g. polymerized fluoroolefins or fluoroalkoxy polymers, copolymers such as e.g. Copolymers of fluorinated ethylene / propylene monomers or terpolymers or also block polymers such as e.g. those which consist of a polyfluorocarbon soft segment and a polyfluorocarbon hard segment which are bonded to one another by polymerisation.
- Such fluorocarbon polymers often also contain inorganic or organic fillers in order to influence the mechanical and / or electrical properties of the plastics.
- inorganic or organic fillers in order to influence the mechanical and / or electrical properties of the plastics.
- the use of such fillers has the disadvantage that other important properties of the plastics are adversely affected. For example, it has been found that the melt viscosity of the polyfluorocarbons is generally increased to such an extent by the addition of fillers that the plastics are difficult or impossible to extrude at all.
- the aim of the present invention is therefore fluorocarbon polymers which correspond in their mechanical and electrical properties to fluorocarbon polymers, but which have a lower melt viscosity than these. That goal will achieved according to the invention with polyfluorocarbons which contain organic titanates as fillers.
- JP-OS 58 16 9572 dated March 29, 1982 describes the production of water-repellent layers for clothing, in particular sports clothing, which can consist of fluorine-containing polymers with the addition of N-butyl titanate or 2-ethylhexyl titanate in combination with tripropoxy titanium stearate.
- the fluorocarbon polymers to which fillers in the form of organic titanates are added according to the invention can be any polyfluorocarbon plastics. examples for this are
- fluorinated olefins such as hexafluoroethylene, perfluoroalkoxy compounds, fluorinated vinyl or vinylidene compounds or other fluorocarbon monomers
- Block polymers e.g. Terblock polymers which can also consist of segments with completely different physical properties, for example a so-called soft segment and a so-called hard segment, which are connected to one another by chemical crosslinking;
- Block polymers mechanically blended with simple polyfluorocarbon compounds
- Polyfluorocarbon plastics that are or have been foamed using a blowing agent, as well as other fluorocarbon plastics.
- the organic titanates to be used according to the invention can be selected from a large number of titanates.
- suitable titanate compound classes are:
- alkoxy compounds such as neoalkoxytriisostearoyl titanate, isopropyltriisostearyl titanate, methacryldiisostearoyl titanate, di (cumylphenylate) oxyacetate;
- sulfonyl compounds such as dodecylbenzenesulfonyl titanate, tridodecylbenzenesulfonyl titanate;
- Phosphorus compounds such as tri (dioctylphosphato) titanate, tri (dioctyl pyrophosphate) titanate, tetraisopropyl di (dioctylphophito) titanate, tetraoctyloxititanium di- (ditridecylphosphite), tetra (2,2-diallyloxymethyl) -1,1-butoxytitanium -di (di-tridecyl phosphite),
- Chelate compounds other than those already mentioned above, such as tri (N-ethylamino-ethylamino) titanate;
- Quaternary titanates such as acrylic functional amines.
- organic titanates according to the invention lowers the melt viscosity of the fluorocarbon polymers, in particular those crosslinked with conventional fillers, to the extent that a melt extrusion is made possible.
- the melt viscosity is reduced to 1/6 of the original value, so that the material obtained can be easily extruded even if thin wall thicknesses are to be achieved.
- fluorocarbon polymers with inorganic additives are those with mineral fibers. These mineral fibers consist for example. Caicium aluminosilakates, are about 3 mm long and are contained in the plastic in an amount of about 25 wt .-%. By adding neoalkoxy-tri (N-ethylamino-ethylamino) titanate, the melt viscosity is reduced to about 1/5 of the original value, so that this material is suitable for injection molding even in very thin sections and sections.
- titanate additive according to the invention is that the elongation and tensile strength of the end product are often also increased.
- the titanate additives according to the invention can also be used for foamed fluorocarbon polymers.
- poly (ethylene tetrafluoro ethylene) (EFTE) using a blowing agent such as magnesium carbonate, azodicarbonamide, P-toluenesulfonyl compounds or the like. be foamed.
- EFTE poly (ethylene tetrafluoro ethylene)
- a blowing agent such as magnesium carbonate, azodicarbonamide, P-toluenesulfonyl compounds or the like.
- isopropyl tri (N-ethylamino-ethylamino) titanate not only achieves such a low melt viscosity that the material can be extruded, but it is additionally achieved that the size of the cells in the foam becomes smaller and the cells are distributed more evenly in the foamed material.
- the end product has much better mechanical and electrical properties than that without the addition of titanate.
- Fluorinated polyethylene / propylene is mixed with super conductive carbon black.
- This material will. e.g. used for EMI shielding, for low-noise coaxial cables or for heating cables with or without temperature control.
- carbon black has the consequence that the melt viscosity is increased in such a way that melt extrusion is difficult or impossible at all.
- melt viscosity is reduced so significantly that melt extrusion is possible without difficulty.
- ETFE 80 parts by weight of ETFE are mixed with 20 parts by weight of glass fibers in a drum.
- the mixture is then extruded at 290 ° C. in an extruder (compounding). All parts of the extruder that come into contact with the mixture consist of a metal that is not attacked by the mixture. Stainless steel, for example, is unsuitable for this. Hostalloy, for example, is suitable.
- the material obtained through compounding leaves the extruder in the form of an endless rod. This is cooled in a water bath and then cut into short pieces. In injection molding machines (or extruders), this material is again heated to about 290 ° C and injected into metal molds.
- Comparative example 2 is repeated with the difference that 0.5% by weight of neoalkoxytriisostearoyl titanate is added to the mixture of 80% ETFE and 20% glass fibers according to the invention. After thorough mixing in the drum, this material is extruded at 290 ° C. and cooled well in water and then cut into pieces. Laboratory tests show that by adding the organic titanate the melt viscosity to about 2.5 g / 10 min. has dropped.
- This material is heated to the thermoplastic temperature of 290 ° C in extruders or injection molding machines. Thanks to the low viscosity, the surface of the melt castings becomes smooth. The material flows well into the molds and also fills small and narrow parts of the mold; Cavities do not arise.
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19853502994 DE3502994A1 (de) | 1985-01-30 | 1985-01-30 | Mit fuellstoffen versehene fluor-kohlenstoff-polymere |
| DEP3502994.3 | 1985-01-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1986004596A1 true WO1986004596A1 (en) | 1986-08-14 |
Family
ID=6261101
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/DE1986/000029 WO1986004596A1 (en) | 1985-01-30 | 1986-01-29 | Fluorocarbon polymers possessing filler materials |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JPS62501849A (enrdf_load_stackoverflow) |
| DE (1) | DE3502994A1 (enrdf_load_stackoverflow) |
| WO (1) | WO1986004596A1 (enrdf_load_stackoverflow) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008079393A1 (en) * | 2006-12-21 | 2008-07-03 | E. I. Du Pont De Nemours And Company | Electrode binder compositions and electrodes for lithium ion batteries and electric double layer capacitors |
| CN108485138A (zh) * | 2018-05-03 | 2018-09-04 | 泰州市亚星塑业有限公司 | 一种聚四氟乙烯薄膜配方及其制法 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1525418A (en) * | 1975-05-15 | 1978-09-20 | Kenrich Petrochemicals | Alkoxy titanate salts |
| US4424294A (en) * | 1981-07-15 | 1984-01-03 | Standard Oil Company, (Indiana) | Injection moldable amide-imide polymers and copolymers containing titanates |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1033638A (en) * | 1963-09-09 | 1966-06-22 | Du Pont | Polytetrafluoroethylene moulding powders and their preparation |
-
1985
- 1985-01-30 DE DE19853502994 patent/DE3502994A1/de not_active Ceased
-
1986
- 1986-01-29 WO PCT/DE1986/000029 patent/WO1986004596A1/de unknown
- 1986-01-29 JP JP61500804A patent/JPS62501849A/ja active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1525418A (en) * | 1975-05-15 | 1978-09-20 | Kenrich Petrochemicals | Alkoxy titanate salts |
| US4424294A (en) * | 1981-07-15 | 1984-01-03 | Standard Oil Company, (Indiana) | Injection moldable amide-imide polymers and copolymers containing titanates |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0115528B2 (enrdf_load_stackoverflow) | 1989-03-17 |
| JPS62501849A (ja) | 1987-07-23 |
| DE3502994A1 (de) | 1986-07-31 |
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