WO1981001409A1 - Coating of poly(arylene sulfide),fluoropolymer and aluminum flake - Google Patents
Coating of poly(arylene sulfide),fluoropolymer and aluminum flake Download PDFInfo
- Publication number
- WO1981001409A1 WO1981001409A1 PCT/US1979/000985 US7900985W WO8101409A1 WO 1981001409 A1 WO1981001409 A1 WO 1981001409A1 US 7900985 W US7900985 W US 7900985W WO 8101409 A1 WO8101409 A1 WO 8101409A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- coating composition
- poly
- fluoropolymer
- coating
- liquid carrier
- Prior art date
Links
- -1 poly(arylene sulfide Chemical compound 0.000 title claims abstract description 18
- 229920002313 fluoropolymer Polymers 0.000 title claims abstract description 15
- 239000004811 fluoropolymer Substances 0.000 title claims abstract description 15
- 229910052782 aluminium Inorganic materials 0.000 title claims abstract description 14
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 title claims abstract description 14
- 238000000576 coating method Methods 0.000 title claims abstract description 14
- 239000011248 coating agent Substances 0.000 title claims description 10
- 239000008199 coating composition Substances 0.000 claims abstract description 18
- 239000007788 liquid Substances 0.000 claims abstract description 11
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 16
- 229920000069 polyphenylene sulfide Polymers 0.000 claims description 11
- 229920005989 resin Polymers 0.000 claims description 11
- 239000011347 resin Substances 0.000 claims description 11
- 239000000178 monomer Substances 0.000 claims description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- 239000000049 pigment Substances 0.000 claims description 8
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 229920001343 polytetrafluoroethylene Polymers 0.000 claims description 6
- 239000004810 polytetrafluoroethylene Substances 0.000 claims description 6
- 239000004408 titanium dioxide Substances 0.000 claims description 6
- 229920001577 copolymer Polymers 0.000 claims description 5
- 239000000758 substrate Substances 0.000 claims description 5
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 claims description 5
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- 150000002430 hydrocarbons Chemical class 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 3
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical group FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 2
- 229920000642 polymer Polymers 0.000 description 9
- 239000004734 Polyphenylene sulfide Substances 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 229940058401 polytetrafluoroethylene Drugs 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 229920004890 Triton X-100 Polymers 0.000 description 3
- 239000013504 Triton X-100 Substances 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 229920013632 Ryton Polymers 0.000 description 2
- 239000004736 Ryton® Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000006231 channel black Substances 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- 229920006358 Fluon Polymers 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229910052977 alkali metal sulfide Chemical group 0.000 description 1
- VXAUWWUXCIMFIM-UHFFFAOYSA-M aluminum;oxygen(2-);hydroxide Chemical compound [OH-].[O-2].[Al+3] VXAUWWUXCIMFIM-UHFFFAOYSA-M 0.000 description 1
- ZCILODAAHLISPY-UHFFFAOYSA-N biphenyl ether Chemical group C1=C(CC=C)C(O)=CC(OC=2C(=CC(CC=C)=CC=2)O)=C1 ZCILODAAHLISPY-UHFFFAOYSA-N 0.000 description 1
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 1
- 239000001055 blue pigment Substances 0.000 description 1
- 235000008429 bread Nutrition 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 150000001923 cyclic compounds Chemical class 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 235000000396 iron Nutrition 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000002780 morpholines Chemical class 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 238000007761 roller coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 235000012773 waffles Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D127/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Coating compositions based on derivatives of such polymers
- C09D127/02—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Coating compositions based on derivatives of such polymers not modified by chemical after-treatment
- C09D127/12—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Coating compositions based on derivatives of such polymers not modified by chemical after-treatment containing fluorine atoms
- C09D127/18—Homopolymers or copolymers of tetrafluoroethene
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D181/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur, with or without nitrogen, oxygen, or carbon only; Coating compositions based on polysulfones; Coating compositions based on derivatives of such polymers
- C09D181/02—Polythioethers; Polythioether-ethers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L81/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur with or without nitrogen, oxygen or carbon only; Compositions of polysulfones; Compositions of derivatives of such polymers
- C08L81/02—Polythioethers; Polythioether-ethers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L81/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur with or without nitrogen, oxygen or carbon only; Compositions of polysulfones; Compositions of derivatives of such polymers
- C08L81/04—Polysulfides
Definitions
- This invention relates to non-stick coating compositions particularly useful on cookware.
- Poly (phenylene sulfide) resins are known for use in cookware coatings. Sometimes fluoropolymers and pigments, extenders or hardening agents such as titanium dioxide and aluminum dioxide are used.
- the present invention provides a coating composition comprising, in weight percentage ranges based on the solids content, about:
- the liquid carrier can be aqueous or organic.
- the poly(arylene sulfide) resin is preferably poly (phenylene sulfide) resin.
- the fluoropolymer is preferably polytetrafluoroethylene, but it can also be a perfluorinated copolymer of hexafluoropropylene and tetrafluoroethylene or a copolymer of tetrafluoroethylene and hydrocarbon ether monomers which have been completely substituted with fluorine atoms.
- the invention also comprises articles of cookware, such as bakeware, coated with such coating compositions and heated to remove the liquid carrier and more or less coalesce the coating.
- Aluminum flake can substantially increase the hardness at elevated temperatures of coating compositions of poly(arylene sulfide) resins and fluoropolymers, with optional titanium dioxide pigment.
- coating compositions have liquid carriers which are either aqueous or organic.
- Applicable arylene sulfide polymers include polymers of the type which are prepared as described in U.S. 3, 354 ,129. As disclosed in this patent, these polymers can be prepared by reacting a polyhalo-substituted cyclic compound containing unsaturation between adjacent ring atoms and an alkali metal sulfide in a polar organic compound. The resulting polymer contains the cyclic structure of the polyhalo-substituted compound coupled in repeating units through a sulfur atom.
- the polymers which are preferred for us e i n the coating procedure of this invention are those polymers having the repeating unit -R-S- where R is phenylene, biphenylene, naphthylene, biphenyl ether, or a lower alkyl substituted derivative thereof.
- R is phenylene, biphenylene, naphthylene, biphenyl ether, or a lower alkyl substituted derivative thereof.
- lower alkyl is meant alkyl groups having 1 to 6 carbon atoms such as methyl, ethyl, propyl, isobutyl, hexyl, and the like.
- the arylene sulfide polymers have melting temperatures within the range of about 205-483°C.
- the arylene sulfide polymer can be lightly cured, i.e., the molecular weight of the polymer can be increased by cross-linking or chain extension, e.g., by heating moderately, prior to application to the substrate.
- PPS polytetra fluoroethylene
- FEP hexafluoropropylene
- aqueous compositions preferably the aluminum flake has been reacted with phosphate ester or emulsified with fatty acid and neutralized to form a morpholine salt.
- Tipure R 900 TiO 2 pigment from Du Pont 4.24
- This premix is then mixed in the following proportions:
- the coating composition is applied to a substrate of any suitable material such as aluminum by suitable techniques such as spraying or roller coating.
- the coating is cured by heating 10 minutes at 400°C. This drives off the liquid carrier and coalesces into a desirable coating. Alternately, the coating can be cured at 370°C for 15 minutes, at 425°C for 5-7 minutes or under equivalent conditions .
- This premix is then mixed in the following proportions:
- Example 2 Two coating compositions were prepared and applied as in Example 1, differing in that one contained the aluminum flake of Example 1 while the other did not.
- the hardness of the two coatings was compared at elevated temperatures by the Erichsen technique described, inter alia, in the article by Weinmann entitled “Ein 14 Geratzzy Hartefug von Antrichen und to Schutz ⁇ berz ⁇ gen", published in Park und Lack, 68, No. 5, 323-326 (1962).
- the results in the following table demonstrate advantages of the invention.
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Paints Or Removers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PCT/US1979/000985 WO1981001409A1 (en) | 1979-11-16 | 1979-11-16 | Coating of poly(arylene sulfide),fluoropolymer and aluminum flake |
JP80501006A JPS56501566A (enrdf_load_stackoverflow) | 1979-11-16 | 1979-11-16 | |
US06/111,039 US4287112A (en) | 1979-11-16 | 1980-01-10 | Coating of poly(arylene sulfide), fluoropolymer and aluminum flake |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PCT/US1979/000985 WO1981001409A1 (en) | 1979-11-16 | 1979-11-16 | Coating of poly(arylene sulfide),fluoropolymer and aluminum flake |
WOUS79/00985 | 1979-11-16 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1981001409A1 true WO1981001409A1 (en) | 1981-05-28 |
Family
ID=22147786
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US1979/000985 WO1981001409A1 (en) | 1979-11-16 | 1979-11-16 | Coating of poly(arylene sulfide),fluoropolymer and aluminum flake |
Country Status (2)
Country | Link |
---|---|
JP (1) | JPS56501566A (enrdf_load_stackoverflow) |
WO (1) | WO1981001409A1 (enrdf_load_stackoverflow) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4914021A (en) * | 1988-03-04 | 1990-04-03 | New England Deaconess Hospital Corporation | Carcinoma orosomucoid-related antigen, a monoclonal antibody thereto, and their uses |
US9630206B2 (en) | 2005-05-12 | 2017-04-25 | Innovatech, Llc | Electrosurgical electrode and method of manufacturing same |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0627259B2 (ja) * | 1985-01-16 | 1994-04-13 | 大日本インキ化学工業株式会社 | 樹脂組成物 |
JP2769319B2 (ja) * | 1987-12-24 | 1998-06-25 | 東京シリコーン株式会社 | 複合体 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3622376A (en) * | 1968-08-15 | 1971-11-23 | Phillips Petroleum Co | TiO{11 {0 IN POLY(ARYLENE SULFIDE) FOR COATING COMPOSITION |
US3701665A (en) * | 1970-12-10 | 1972-10-31 | Phillips Petroleum Co | Reduction of sulfur extraction from poly(arylene sulfide) coated cookware |
US3993843A (en) * | 1973-03-13 | 1976-11-23 | E. I. Du Pont De Nemours And Company | Aqueous dispersion of aromatic polysulfone resin with perfluorocarbon resin, and coated articles |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5027787A (enrdf_load_stackoverflow) * | 1973-07-12 | 1975-03-22 | ||
JPS5718557B2 (enrdf_load_stackoverflow) * | 1973-11-13 | 1982-04-17 | ||
JPS5346862A (en) * | 1976-10-06 | 1978-04-26 | Tokyo Shibaura Electric Co | Rice cooking and cooking container |
JPS6010547B2 (ja) * | 1977-01-21 | 1985-03-18 | 積水化学工業株式会社 | ポリフエニレンサルフアイド組成物 |
-
1979
- 1979-11-16 JP JP80501006A patent/JPS56501566A/ja active Pending
- 1979-11-16 WO PCT/US1979/000985 patent/WO1981001409A1/en unknown
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3622376A (en) * | 1968-08-15 | 1971-11-23 | Phillips Petroleum Co | TiO{11 {0 IN POLY(ARYLENE SULFIDE) FOR COATING COMPOSITION |
US3701665A (en) * | 1970-12-10 | 1972-10-31 | Phillips Petroleum Co | Reduction of sulfur extraction from poly(arylene sulfide) coated cookware |
US3993843A (en) * | 1973-03-13 | 1976-11-23 | E. I. Du Pont De Nemours And Company | Aqueous dispersion of aromatic polysulfone resin with perfluorocarbon resin, and coated articles |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4914021A (en) * | 1988-03-04 | 1990-04-03 | New England Deaconess Hospital Corporation | Carcinoma orosomucoid-related antigen, a monoclonal antibody thereto, and their uses |
US9630206B2 (en) | 2005-05-12 | 2017-04-25 | Innovatech, Llc | Electrosurgical electrode and method of manufacturing same |
US10463420B2 (en) | 2005-05-12 | 2019-11-05 | Innovatech Llc | Electrosurgical electrode and method of manufacturing same |
US11246645B2 (en) | 2005-05-12 | 2022-02-15 | Innovatech, Llc | Electrosurgical electrode and method of manufacturing same |
Also Published As
Publication number | Publication date |
---|---|
JPS56501566A (enrdf_load_stackoverflow) | 1981-10-29 |
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