US3634125A - Method of coating iron or titanium containing substrate with poly(arylene sulfide) - Google Patents
Method of coating iron or titanium containing substrate with poly(arylene sulfide) Download PDFInfo
- Publication number
- US3634125A US3634125A US752767A US3634125DA US3634125A US 3634125 A US3634125 A US 3634125A US 752767 A US752767 A US 752767A US 3634125D A US3634125D A US 3634125DA US 3634125 A US3634125 A US 3634125A
- Authority
- US
- United States
- Prior art keywords
- poly
- process according
- arylene sulfide
- substrate
- coating
- 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 - Lifetime
Links
- -1 poly(arylene sulfide Chemical compound 0.000 title claims abstract description 54
- 239000000758 substrate Substances 0.000 title claims abstract description 32
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 title claims abstract description 18
- 239000010936 titanium Substances 0.000 title claims abstract description 18
- 229910052719 titanium Inorganic materials 0.000 title claims abstract description 18
- 238000000034 method Methods 0.000 title claims description 29
- 238000000576 coating method Methods 0.000 title claims description 25
- 239000011248 coating agent Substances 0.000 title claims description 22
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 title abstract description 30
- 229910052742 iron Inorganic materials 0.000 title abstract description 15
- 239000000203 mixture Substances 0.000 claims abstract description 14
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 31
- 229910000831 Steel Inorganic materials 0.000 claims description 12
- 239000010959 steel Substances 0.000 claims description 12
- 229920000069 polyphenylene sulfide Polymers 0.000 claims description 11
- 238000011282 treatment Methods 0.000 claims description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
- 239000001301 oxygen Substances 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 238000010438 heat treatment Methods 0.000 claims description 8
- 239000008199 coating composition Substances 0.000 claims description 7
- 239000007789 gas Substances 0.000 claims description 7
- 239000003085 diluting agent Substances 0.000 claims description 6
- 239000002002 slurry Substances 0.000 claims description 4
- 239000000956 alloy Substances 0.000 abstract description 6
- 229910045601 alloy Inorganic materials 0.000 abstract description 6
- 239000004408 titanium dioxide Substances 0.000 description 11
- 229910052751 metal Inorganic materials 0.000 description 10
- 239000002184 metal Substances 0.000 description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 4
- 238000004140 cleaning Methods 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 238000009863 impact test Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 3
- 210000002268 wool Anatomy 0.000 description 3
- JTPNRXUCIXHOKM-UHFFFAOYSA-N 1-chloronaphthalene Chemical compound C1=CC=C2C(Cl)=CC=CC2=C1 JTPNRXUCIXHOKM-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 101100264195 Caenorhabditis elegans app-1 gene Proteins 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000006255 coating slurry Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 238000005238 degreasing Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- FBSAITBEAPNWJG-UHFFFAOYSA-N dimethyl phthalate Natural products CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 description 1
- 229960001826 dimethylphthalate Drugs 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 238000009499 grossing Methods 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 229910000398 iron phosphate Inorganic materials 0.000 description 1
- WBJZTOZJJYAKHQ-UHFFFAOYSA-K iron(3+) phosphate Chemical compound [Fe+3].[O-]P([O-])([O-])=O WBJZTOZJJYAKHQ-UHFFFAOYSA-K 0.000 description 1
- 230000007775 late Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000003345 natural gas Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- LRXTYHSAJDENHV-UHFFFAOYSA-H zinc phosphate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LRXTYHSAJDENHV-UHFFFAOYSA-H 0.000 description 1
- 229910000165 zinc phosphate Inorganic materials 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
- 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
Definitions
- a substrate of iron or titanium or an alloy containing iron and/or titanium is pretreated at a temperature of about 650 F. or higher, and thereafter coated with a composition comprising a poly(ary1ene sulfide).
- This invention relates to improved methods of applying poly(arylene sulfide) coatings. In a more specific aspect, it re lates to heattreating iron ortitanium containing substrates prior to coating with poly(arylene sulfide) compositions such as poly(phenylene sulfide).
- Po1y(arylene sulfides) such as poly(phenylene sulfide) are well known in the art for their high-temperature stability. While it is generally regarded in the art that these polymers can be adhered to metallic substrates, poly(arylene sulfide) coated articles have not yet achieved significant commercial success. It has been found that, while poly(arylene sulfides) do adhere to metal substrates as broadly alleged in the prior art, the metals which would be of greatest commercial significance if coated with a poly(arylene sulfide), such as steel, titanium. and. alloys containing iron and/or titanium, form a very weak bond to the poly(arylene sulfide).
- a poly(arylene sulfide) such as steel, titanium. and. alloys containing iron and/or titanium
- iron or titanium containing substrates are pretreated at a temperature of about 650 F. or higher prior to application of a coating of a poly(arylene sulfide).
- Any poly(arylene sulfide) can be used in the practice of this invention. Suitable polymers are disclosed, for instance, in Edmonds et al., U.S. Pat. No. 3,354,l29, Nov. 21, I967. The presently preferred polymer is poly(phenylene sulfide).
- poly(arylene sulfide) is meant to include not only homopolymers but also arylene sulfide copolymers, terpolymers, and the like.
- Suitable poly(arylene sulfides) of this invention are those having inherent viscosities in chloronaphthalene at 206 C. of at least 0.1, preferably between 0.1 and 0.3, more preferably between 0.13 and 0.23.
- iron as used herein is meant to include steel and any alloy containing iron as a major constituent.
- the instant invention is applicable to steel substrates, titanium substrates, and substrates of alloys containing a major proportion of iron and/or titanium.
- the high-temperature pretreating step for the substrate can be carried out by any means known to the art, such as in an oven or in a flame, preferably a gas oxygen flame.
- the treatment can be carried out at any temperature between about 650 F. and the temperature at which the particular metal in question begins to deform or soften.
- temperatures of 675-800 are used for the oven treatment.
- the flame treatment is done with a gas oxygen flame having a temperature of about l,8l5 C. (natural gas plus oxygen gives a flame of about 2,930 C. and can also be used), and is continued until the metal begins to turn bluish.
- this pretreating step is carried out in the presence of an oxygencontaining gas such as air.
- This pretreating step can take from 1 second to 5 hours. Generally, if oven treating is being utilized, the time will vary from about l5 to 90 minutes depending on the temperature.
- This time will vary greatly depending on the intensity of the flame, but generally will be within the range of l to 5 minutes.
- the poly(arylene sulfide) coating composition contains titanium dioxide. Any titanium dioxide can be used. The presently preferred form is the rutile form.
- the titanium dioxide can be present in an amount within the range of 0.5 to 50 weight percent based on the weight of the solids, that is, the weight of the poly(arylene sulfide) and the titanium dioxide. More preferably, the concentration of titanium dioxide will be within the range of 10 to 35 weight percent.
- the coating is preferably applied in the form ofa slurry of the poly(arylene sulfide) and titanium dioxide in an inert diluent.
- any low-boiling liquid can be used as the diluent.
- Preferred materials include ethylene glycol, methyl alcohol, water, and toluene, width ethylene glycol being the most preferred diluent.
- Certain high-boiling materials such as chlorinated biphenyl and dimethyl phthalate have been found to be less satisfactory.
- the coating slurries can be applied by any conventional means such as spraying, smoothing with a doctor blade, and the like.
- the compositions can be blended with conventional additives such as stabilizers, sofcontinued until a color change is noted in the metal, for inteners, extenders, other polymers, other pigments, specific curing agents, and the like.
- the solvent is first evaporated off, and then at about 500 F.. the polymer melts and fuses together into a continuous coating.
- cross-linking agents can be added, it is preferred to allow the cross-linking to take place without specific additives for that purpose.
- the exact nature of the cross-linking reaction is not known, but is is known that it occurs much faster in the presence of air or oxygen than in an inert atmosphere.
- the curing is done in air at a temperature of S50800 F., preferably 650-750 F., the preferred time within the range of 1 minute to 5 hours, preferably 15 minutes to 2 hours.
- EXAMPLE I A slurry of 60 grams of poly(phenylene sulfide) and 20 grams of rutile titanium dioxide in I grams of ethylene glycol was stirred in a Waring blender for IS minutes.
- the poly(phenylene sulfide) was an uncross-linked product having an inherent viscosity in chloronaphthalene of 0.2 at 206 C. (In runs 1 and 3, the titanium dioxide was omitted from the formulation).
- Steel panels measuring 3X6 inches were coated with this formulation; three separate coats were applied, the composition being cured at about 700 F. for about one-half hour after each coating. The following sequential steps were carried out on said steel panels. All of the steel panels were first cleaned by wiping with acetone.
- control panel was then coated directly, while in runs l and 2 the panel was pretreated at 700 F. in an oven under air atmosphere and run 3 was flame treated for 2 minutes prior to coating. All of the pretreated panels were cooled prior to applying the coating. The results were as follows:
- Gardner Laboratories Reverse Impact Tester This equipment comprises a rounded tip which rests above the sample on the reverse side from the coating. A ram is raised a calibrated distance and dropped against the tip which then impinges on the back side ofthe coated slab. The side opposite that which comes in contact with the tip, that is, the side having the coating, is examined for cracks and loosencss ofthe coating.
- EXAMPLE ll The following conventional cleaning techniques were employed on steel panels in lieu ofthe high-temperature pretreatment, and the panels were thereafter coated and otherwise treated in a manner similar to that in example I. All of the following treatments resulted in either no improvement in adhesion or else detracted from the quality of the bond.
- Zinc phosphate (Panels dipped in a solution of 300 grams, 85 percent l-l PO and 250 grams Zn ,(PO,) in 1,200 grams deionized water.
- EXAMPLE III A formulation similar to that of example I was applied to titanium coupons. One group of the coupons has been pretreated in a gas oxygen flame until the metal turned blue. The other was simply degreased with a solvent. The coating was then cut with a knife blade in the area to be tested. The coating on the laminate with the substrate which has been pretreated in a flame passed the 160 in.-lb. reverse impact test which was the limit of the machine and the coatings on the coupons which had not received the flame treatment failed this test at I60 in.-lb.
- EXAMPLE IV Aluminum coupons were coated with a formulation similar to that of example I. One group of the aluminum coupons was given a high-temperature pretreatment and the other was not. In both instances, the metal failed in the reverse impact test with the bonds still intact.
- Example IV shows that no improvement is effected by heat treatment of aluminum, as evidenced by the reverse impact test.
- a coating process comprising the following sequential steps: pretreating a substrate selected from the group consisting ofiron, titanium, and alloys containing a major proportion of at least one of iron and titanium, which substrate exhibits a weak bond to poly(arylene sulfide), by heating said substrate to a temperature of at least 650 F.; cooling said substrate; and thereafter applying to said pretreated substrate a coating composition comprising said poly(arylene sulfide).
- a process according to claim 1 wherein said pretreatment comprises flame treatment.
- a process according to claim I wherein said pretreatment comprises flame treating with a gas oxygen flame until said substrate turns bluish.
- said coating composition contains 0.5 to 50 weight percent TiO based on the total weight ofthe poly(arylene sulfide) and TiO 6.
- said poly(arylene sulfide) is poly(phenylene sulfide).
- poly(arylene sulfide) is poly(phenylene sulfide)
- said process comprising in addition heating said composition, after said composition has been applied to said substrate, at a temperature within the range of550 to 800 F. to evaporate said diluent and fuse said poly(arylene sulfide) into a continuous coating.
- poly(phenylene sulfide) contains between 0.5 and 50 weight percent Tit] based on the total weight of the poly( arylene sulfide) and TiO 10.
- substrate is steel.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Application Of Or Painting With Fluid Materials (AREA)
- Paints Or Removers (AREA)
- Laminated Bodies (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US75276768A | 1968-08-15 | 1968-08-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3634125A true US3634125A (en) | 1972-01-11 |
Family
ID=25027747
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US752767A Expired - Lifetime US3634125A (en) | 1968-08-15 | 1968-08-15 | Method of coating iron or titanium containing substrate with poly(arylene sulfide) |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3634125A (enrdf_load_stackoverflow) |
| JP (1) | JPS5142133B1 (enrdf_load_stackoverflow) |
| DE (1) | DE1941140C3 (enrdf_load_stackoverflow) |
| GB (1) | GB1269920A (enrdf_load_stackoverflow) |
Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3928661A (en) * | 1973-06-01 | 1975-12-23 | Phillips Petroleum Co | Selective coating of a substrate with poly(arylene sulfide) |
| US3930078A (en) * | 1973-11-29 | 1975-12-30 | Phillips Petroleum Co | Coating with arylene sulfide polymer containing compounds to enhance cure |
| US3931419A (en) * | 1973-11-29 | 1976-01-06 | Phillips Petroleum Company | Coating with arylene sulfide polymer cured with the aid of certain compounds |
| US3964582A (en) * | 1974-07-26 | 1976-06-22 | Wallace-Murray Corporation | Fan drive hydraulic coupling |
| US3979543A (en) * | 1973-06-13 | 1976-09-07 | Phillips Petroleum Company | Article having a poly(arylene sulfide) coating and method of producing |
| US4011121A (en) * | 1975-04-30 | 1977-03-08 | Phillips Petroleum Company | Adhesive bonding of poly(arylene sulfide) surfaces |
| US4075388A (en) * | 1975-04-30 | 1978-02-21 | Phillips Petroleum Company | Adhesive bonding of poly(arylene sulfide) surfaces |
| US4212922A (en) * | 1978-10-02 | 1980-07-15 | Phillips Petroleum Company | Poly(arylene sulfide) resin coating |
| US4237039A (en) * | 1978-12-18 | 1980-12-02 | Phillips Petroleum Company | Salts of arylalkanoic acids as corrosion inhibitors for poly(arylene sulfide)s |
| US4247598A (en) * | 1979-05-29 | 1981-01-27 | Phillips Petroleum Company | Applying powder arylene sulfide polymer coatings to substrates |
| US4355059A (en) * | 1981-04-24 | 1982-10-19 | Phillips Petroleum Company | Poly(arylene sulfide) composition containing a polyolefin |
| US4835051A (en) * | 1987-02-24 | 1989-05-30 | Phillips Petroleum Company | Coatings of arylene sulfide polymers |
| US4904502A (en) * | 1987-02-24 | 1990-02-27 | Phillips Petroleum Company | Coatings of arylene sulfide polymers |
| US5015686A (en) * | 1987-02-24 | 1991-05-14 | Phillips Petroleum Company | Coatings of arylene sulfide polymers |
| US5272185A (en) * | 1990-10-26 | 1993-12-21 | The Furukawa Electric Co., Ltd. | Polyphenylenesulfide composition for powder coating |
| US20030175421A1 (en) * | 2002-03-13 | 2003-09-18 | Delphi Technologies, Inc. | Process for reducing contaminants on surfaces of die cast components |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5493188U (enrdf_load_stackoverflow) * | 1977-12-14 | 1979-07-02 | ||
| JPS6287589U (enrdf_load_stackoverflow) * | 1985-11-22 | 1987-06-04 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3297630A (en) * | 1963-09-25 | 1967-01-10 | Thiokol Chemical Corp | Stabilized polysulfide polymer based compositions containing organo-metallic tin compounds |
| US3354129A (en) * | 1963-11-27 | 1967-11-21 | Phillips Petroleum Co | Production of polymers from aromatic compounds |
| US3408342A (en) * | 1965-08-31 | 1968-10-29 | Phillips Petroleum Co | Stabilized poly(arylene sulfides |
| US3451848A (en) * | 1966-03-31 | 1969-06-24 | Standard Oil Co | Method of coating magnet wire with a polytrimellitamide |
-
1968
- 1968-08-15 US US752767A patent/US3634125A/en not_active Expired - Lifetime
-
1969
- 1969-08-13 DE DE1941140A patent/DE1941140C3/de not_active Expired
- 1969-08-14 GB GB50486/71A patent/GB1269920A/en not_active Expired
-
1974
- 1974-03-14 JP JP49029580A patent/JPS5142133B1/ja active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3297630A (en) * | 1963-09-25 | 1967-01-10 | Thiokol Chemical Corp | Stabilized polysulfide polymer based compositions containing organo-metallic tin compounds |
| US3354129A (en) * | 1963-11-27 | 1967-11-21 | Phillips Petroleum Co | Production of polymers from aromatic compounds |
| US3408342A (en) * | 1965-08-31 | 1968-10-29 | Phillips Petroleum Co | Stabilized poly(arylene sulfides |
| US3451848A (en) * | 1966-03-31 | 1969-06-24 | Standard Oil Co | Method of coating magnet wire with a polytrimellitamide |
Non-Patent Citations (2)
| Title |
|---|
| Gregory et al., Heat Treatment of Steel, N.Y., Pitman, 1958, p. 28, 32, 353, 216 and 217. TS320G72, 1958 * |
| McClintick et al., Physical Metallurgy and Heat Treatment of Titanium Alloys, Niles, Ohio, Mallory-Sharon, 1955, p. 26. TN799TSM21 * |
Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3928661A (en) * | 1973-06-01 | 1975-12-23 | Phillips Petroleum Co | Selective coating of a substrate with poly(arylene sulfide) |
| US3979543A (en) * | 1973-06-13 | 1976-09-07 | Phillips Petroleum Company | Article having a poly(arylene sulfide) coating and method of producing |
| US3930078A (en) * | 1973-11-29 | 1975-12-30 | Phillips Petroleum Co | Coating with arylene sulfide polymer containing compounds to enhance cure |
| US3931419A (en) * | 1973-11-29 | 1976-01-06 | Phillips Petroleum Company | Coating with arylene sulfide polymer cured with the aid of certain compounds |
| US3964582A (en) * | 1974-07-26 | 1976-06-22 | Wallace-Murray Corporation | Fan drive hydraulic coupling |
| US4011121A (en) * | 1975-04-30 | 1977-03-08 | Phillips Petroleum Company | Adhesive bonding of poly(arylene sulfide) surfaces |
| US4075388A (en) * | 1975-04-30 | 1978-02-21 | Phillips Petroleum Company | Adhesive bonding of poly(arylene sulfide) surfaces |
| US4212922A (en) * | 1978-10-02 | 1980-07-15 | Phillips Petroleum Company | Poly(arylene sulfide) resin coating |
| US4237039A (en) * | 1978-12-18 | 1980-12-02 | Phillips Petroleum Company | Salts of arylalkanoic acids as corrosion inhibitors for poly(arylene sulfide)s |
| US4247598A (en) * | 1979-05-29 | 1981-01-27 | Phillips Petroleum Company | Applying powder arylene sulfide polymer coatings to substrates |
| US4355059A (en) * | 1981-04-24 | 1982-10-19 | Phillips Petroleum Company | Poly(arylene sulfide) composition containing a polyolefin |
| US4835051A (en) * | 1987-02-24 | 1989-05-30 | Phillips Petroleum Company | Coatings of arylene sulfide polymers |
| US4904502A (en) * | 1987-02-24 | 1990-02-27 | Phillips Petroleum Company | Coatings of arylene sulfide polymers |
| US5015686A (en) * | 1987-02-24 | 1991-05-14 | Phillips Petroleum Company | Coatings of arylene sulfide polymers |
| US5272185A (en) * | 1990-10-26 | 1993-12-21 | The Furukawa Electric Co., Ltd. | Polyphenylenesulfide composition for powder coating |
| US20030175421A1 (en) * | 2002-03-13 | 2003-09-18 | Delphi Technologies, Inc. | Process for reducing contaminants on surfaces of die cast components |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1269920A (en) | 1972-04-06 |
| DE1941140B2 (de) | 1974-02-28 |
| DE1941140A1 (de) | 1970-02-26 |
| JPS5142133B1 (enrdf_load_stackoverflow) | 1976-11-13 |
| DE1941140C3 (de) | 1974-10-10 |
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