CA2325732A1 - Process for producing paintable polymeric articles - Google Patents
Process for producing paintable polymeric articles Download PDFInfo
- Publication number
- CA2325732A1 CA2325732A1 CA002325732A CA2325732A CA2325732A1 CA 2325732 A1 CA2325732 A1 CA 2325732A1 CA 002325732 A CA002325732 A CA 002325732A CA 2325732 A CA2325732 A CA 2325732A CA 2325732 A1 CA2325732 A1 CA 2325732A1
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- Prior art keywords
- acid
- group
- polymeric material
- oxidizing agent
- mixtures
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- 238000000034 method Methods 0.000 title claims abstract 24
- 239000000203 mixture Substances 0.000 claims abstract 32
- 239000000463 material Substances 0.000 claims abstract 25
- 239000007800 oxidant agent Substances 0.000 claims abstract 24
- 239000000758 substrate Substances 0.000 claims abstract 18
- 239000003795 chemical substances by application Substances 0.000 claims abstract 14
- 150000002927 oxygen compounds Chemical class 0.000 claims abstract 4
- 230000000593 degrading effect Effects 0.000 claims abstract 3
- 125000000524 functional group Chemical group 0.000 claims abstract 3
- 239000000126 substance Substances 0.000 claims abstract 3
- -1 alkali metal salts Chemical class 0.000 claims 29
- 150000004677 hydrates Chemical class 0.000 claims 14
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 13
- 230000003213 activating effect Effects 0.000 claims 11
- 239000002253 acid Chemical class 0.000 claims 10
- 150000001735 carboxylic acids Chemical class 0.000 claims 10
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 6
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims 6
- 239000003513 alkali Substances 0.000 claims 5
- 229910052783 alkali metal Inorganic materials 0.000 claims 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 5
- QYHFIVBSNOWOCQ-UHFFFAOYSA-N selenic acid Chemical class O[Se](O)(=O)=O QYHFIVBSNOWOCQ-UHFFFAOYSA-N 0.000 claims 5
- 238000006243 chemical reaction Methods 0.000 claims 4
- 239000000543 intermediate Substances 0.000 claims 4
- 238000000465 moulding Methods 0.000 claims 4
- 229920000728 polyester Polymers 0.000 claims 4
- 150000003458 sulfonic acid derivatives Chemical class 0.000 claims 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical class OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims 3
- 239000004952 Polyamide Substances 0.000 claims 3
- 150000008064 anhydrides Chemical class 0.000 claims 3
- 239000007864 aqueous solution Substances 0.000 claims 3
- 229910052796 boron Inorganic materials 0.000 claims 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 3
- 229910052794 bromium Inorganic materials 0.000 claims 3
- XTEGARKTQYYJKE-UHFFFAOYSA-N chloric acid Chemical compound OCl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-N 0.000 claims 3
- 229940005991 chloric acid Drugs 0.000 claims 3
- 239000000460 chlorine Substances 0.000 claims 3
- 229910052801 chlorine Inorganic materials 0.000 claims 3
- CUILPNURFADTPE-UHFFFAOYSA-N hypobromous acid Chemical compound BrO CUILPNURFADTPE-UHFFFAOYSA-N 0.000 claims 3
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- 229920002647 polyamide Polymers 0.000 claims 3
- 239000007787 solid Substances 0.000 claims 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 2
- 229920001634 Copolyester Polymers 0.000 claims 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims 2
- 239000004698 Polyethylene Substances 0.000 claims 2
- 239000004743 Polypropylene Substances 0.000 claims 2
- 150000001342 alkaline earth metals Chemical class 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 2
- SXDBWCPKPHAZSM-UHFFFAOYSA-N bromic acid Chemical compound OBr(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-N 0.000 claims 2
- 150000001991 dicarboxylic acids Chemical class 0.000 claims 2
- QFWPJPIVLCBXFJ-UHFFFAOYSA-N glymidine Chemical compound N1=CC(OCCOC)=CN=C1NS(=O)(=O)C1=CC=CC=C1 QFWPJPIVLCBXFJ-UHFFFAOYSA-N 0.000 claims 2
- 150000004820 halides Chemical class 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 238000001746 injection moulding Methods 0.000 claims 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 2
- 229910017604 nitric acid Inorganic materials 0.000 claims 2
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 claims 2
- 229920000573 polyethylene Polymers 0.000 claims 2
- 229920000642 polymer Polymers 0.000 claims 2
- 229920001155 polypropylene Polymers 0.000 claims 2
- 229920001296 polysiloxane Polymers 0.000 claims 2
- 238000005507 spraying Methods 0.000 claims 2
- 229920002725 thermoplastic elastomer Polymers 0.000 claims 2
- VSKJLJHPAFKHBX-UHFFFAOYSA-N 2-methylbuta-1,3-diene;styrene Chemical compound CC(=C)C=C.C=CC1=CC=CC=C1.C=CC1=CC=CC=C1 VSKJLJHPAFKHBX-UHFFFAOYSA-N 0.000 claims 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- ZKQDCIXGCQPQNV-UHFFFAOYSA-N Calcium hypochlorite Chemical compound [Ca+2].Cl[O-].Cl[O-] ZKQDCIXGCQPQNV-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 229920000877 Melamine resin Polymers 0.000 claims 1
- 229920002319 Poly(methyl acrylate) Polymers 0.000 claims 1
- 229920002367 Polyisobutene Polymers 0.000 claims 1
- 239000004793 Polystyrene Substances 0.000 claims 1
- 229920001756 Polyvinyl chloride acetate Polymers 0.000 claims 1
- 239000005708 Sodium hypochlorite Substances 0.000 claims 1
- 229920001807 Urea-formaldehyde Polymers 0.000 claims 1
- 229960000583 acetic acid Drugs 0.000 claims 1
- 239000000853 adhesive Substances 0.000 claims 1
- 230000001070 adhesive effect Effects 0.000 claims 1
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 239000004327 boric acid Substances 0.000 claims 1
- FACXGONDLDSNOE-UHFFFAOYSA-N buta-1,3-diene;styrene Chemical compound C=CC=C.C=CC1=CC=CC=C1.C=CC1=CC=CC=C1 FACXGONDLDSNOE-UHFFFAOYSA-N 0.000 claims 1
- XGKYJLTXGVQMSF-UHFFFAOYSA-N calcium dihypochlorite tetrahydrate Chemical compound O.O.O.O.[Ca++].[O-]Cl.[O-]Cl XGKYJLTXGVQMSF-UHFFFAOYSA-N 0.000 claims 1
- 235000013877 carbamide Nutrition 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 229920002678 cellulose Polymers 0.000 claims 1
- 235000010980 cellulose Nutrition 0.000 claims 1
- 239000007806 chemical reaction intermediate Substances 0.000 claims 1
- 238000009833 condensation Methods 0.000 claims 1
- 230000005494 condensation Effects 0.000 claims 1
- 229920001577 copolymer Polymers 0.000 claims 1
- 238000000354 decomposition reaction Methods 0.000 claims 1
- 150000002170 ethers Chemical class 0.000 claims 1
- IVJISJACKSSFGE-UHFFFAOYSA-N formaldehyde;1,3,5-triazine-2,4,6-triamine Chemical class O=C.NC1=NC(N)=NC(N)=N1 IVJISJACKSSFGE-UHFFFAOYSA-N 0.000 claims 1
- 235000019253 formic acid Nutrition 0.000 claims 1
- 239000012362 glacial acetic acid Substances 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 239000011630 iodine Substances 0.000 claims 1
- 229920001778 nylon Polymers 0.000 claims 1
- 235000006408 oxalic acid Nutrition 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 claims 1
- 229920002239 polyacrylonitrile Polymers 0.000 claims 1
- 229920001707 polybutylene terephthalate Polymers 0.000 claims 1
- 239000004417 polycarbonate Substances 0.000 claims 1
- 229920000515 polycarbonate Polymers 0.000 claims 1
- 229920006149 polyester-amide block copolymer Polymers 0.000 claims 1
- 229920000570 polyether Polymers 0.000 claims 1
- 229920000139 polyethylene terephthalate Polymers 0.000 claims 1
- 239000005020 polyethylene terephthalate Substances 0.000 claims 1
- 229920001195 polyisoprene Polymers 0.000 claims 1
- 239000004926 polymethyl methacrylate Substances 0.000 claims 1
- 229920000098 polyolefin Polymers 0.000 claims 1
- 229920006324 polyoxymethylene Polymers 0.000 claims 1
- 229920002223 polystyrene Polymers 0.000 claims 1
- 229920001021 polysulfide Polymers 0.000 claims 1
- 239000005077 polysulfide Substances 0.000 claims 1
- 150000008117 polysulfides Polymers 0.000 claims 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 claims 1
- 239000004810 polytetrafluoroethylene Substances 0.000 claims 1
- 229920002635 polyurethane Polymers 0.000 claims 1
- 239000004814 polyurethane Substances 0.000 claims 1
- 239000004800 polyvinyl chloride Substances 0.000 claims 1
- 229920000915 polyvinyl chloride Polymers 0.000 claims 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 claims 1
- 239000007921 spray Substances 0.000 claims 1
- 229920000468 styrene butadiene styrene block copolymer Polymers 0.000 claims 1
- 239000000725 suspension Substances 0.000 claims 1
- 150000003672 ureas Chemical class 0.000 claims 1
- 239000000052 vinegar Substances 0.000 claims 1
- 235000021419 vinegar Nutrition 0.000 claims 1
- 239000012190 activator Substances 0.000 abstract 2
- 125000002843 carboxylic acid group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/06—Oxidation
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- Chemical & Material Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Treatments Of Macromolecular Shaped Articles (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
A method for improving surface adhesion characteristics of a polymeric substrate and/or virgin polymeric material in which the portion of the surface of the polymeric substrate and/or virgin polymeric material to be treated is contacted with a composition containing at least one oxidizing agent. The oxidizing agent in the composition is present in a kinetically degrading state capable of producing at least one chemical intermediate which is reactive with the polymeric substrate/virgin polymeric material. Contact between the composition containing the oxidizing agent and the polymeric substrate/virgin polymeric material is maintained for an interval sufficient to produce or modify functional groups in the polymeric substrate/virgin polymeric material. The oxidizing agent of choice is a halogenated bivalent oxygen compound. The oxidizing agent is activated by an activator agent containing at least one carboxylic acid group or derivative thereof. The activator agent may be present in the composition upon initial contact with the polymeric substrate/virgin polymeric material, or may be added to the composition subsequent to initial contact with the polymeric substrate/virgin polymeric material.
Claims (20)
1. A method for improving adhesion characteristics of a polymeric material, comprising the steps of:
contacting the polymeric material with a composition containing at least one oxidizing agent, said oxidizing agent present in a kinetically degrading state which produces at least one chemical intermediate reactive with the polymeric substrate in a controlled reaction mechanism; and maintaining contact between the polymeric material and the composition for an interval sufficient to impart functional groups derived from said oxidizing agent into the polymeric material;
wherein said oxidizing agent is a bivalent oxygen compound selected from the group consisting of oxycompounds of chlorine, oxycompounds of bromine, oxycompounds of iodine, oxycompounds of boron, oxycompounds of nitrogen and mixtures thereof.
contacting the polymeric material with a composition containing at least one oxidizing agent, said oxidizing agent present in a kinetically degrading state which produces at least one chemical intermediate reactive with the polymeric substrate in a controlled reaction mechanism; and maintaining contact between the polymeric material and the composition for an interval sufficient to impart functional groups derived from said oxidizing agent into the polymeric material;
wherein said oxidizing agent is a bivalent oxygen compound selected from the group consisting of oxycompounds of chlorine, oxycompounds of bromine, oxycompounds of iodine, oxycompounds of boron, oxycompounds of nitrogen and mixtures thereof.
2. The method of claim 1 wherein said bivalent oxygen compound is selected from the group consisting of:
oxycompounds of. chlorine selected from the group consisting of hypochlorous acid, alkali metal salts of hypochlorous acid and hydrates thereof, alkaline earth metal salts of hypochlorous acid and hydrates thereof, perchloric acid, alkali metal salts of perchloric acid and hydrates thereof, chloric acid, alkali metal salts of chloric acid and hydrates thereof, alkaline earth metal salts of chloric acid and hydrates thereof;
oxycompounds of bromine selected from the group consisting of hypobromous acid, alkali metal salts of hypobromous acid and hydrates thereof, alkaline earth metal salts of hypobromous acid and hydrates thereof, bromic acid, alkali and alkaline earth metal salts of bromic acid and hydrates thereof;
oxycompounds of iodine selected from the group consisting of iodic acid, alkali and alkaline earth metal salts of iodic acid and hydrates thereof, periodic acid, alkali and alkaline earth metal salts of periodic acid and hydrates thereof;
oxycompounds of boron selected from the group consisting of boric acid, alkaline earth and alkali metal salts and hydrates thereof, alkali perborates and hydrates thereof, alkaline earth metal perborates and hydrates thereof;
oxycompounds of nitrogen selected from the group consisting of nitric acid, alkali and alkaline earth metal salts of nitric acid and hydrates thereof;
and mixtures thereof.
oxycompounds of. chlorine selected from the group consisting of hypochlorous acid, alkali metal salts of hypochlorous acid and hydrates thereof, alkaline earth metal salts of hypochlorous acid and hydrates thereof, perchloric acid, alkali metal salts of perchloric acid and hydrates thereof, chloric acid, alkali metal salts of chloric acid and hydrates thereof, alkaline earth metal salts of chloric acid and hydrates thereof;
oxycompounds of bromine selected from the group consisting of hypobromous acid, alkali metal salts of hypobromous acid and hydrates thereof, alkaline earth metal salts of hypobromous acid and hydrates thereof, bromic acid, alkali and alkaline earth metal salts of bromic acid and hydrates thereof;
oxycompounds of iodine selected from the group consisting of iodic acid, alkali and alkaline earth metal salts of iodic acid and hydrates thereof, periodic acid, alkali and alkaline earth metal salts of periodic acid and hydrates thereof;
oxycompounds of boron selected from the group consisting of boric acid, alkaline earth and alkali metal salts and hydrates thereof, alkali perborates and hydrates thereof, alkaline earth metal perborates and hydrates thereof;
oxycompounds of nitrogen selected from the group consisting of nitric acid, alkali and alkaline earth metal salts of nitric acid and hydrates thereof;
and mixtures thereof.
3. The method of claim 1, further comprising the step of reacting said oxidizing agent with an activating agent which preferentially reacts with said oxidizing agent to produce said at least one intermediate reactive with the polymeric substrate, said activating agent selected from the group consisting of carboxylic acids, anhydride derivatives of carboxylic acids, acid halide derivatives of carboxylic acids, sulfonic acid derivatives of carboxylic acids, selenic acid derivatives of carboxylic acids, perchloric acid derivatives of carboxylic acid, boric acid derivatives of carboxylic acid, dicarboxylic acid, anhydride derivatives of dicarboxylic acid, acid halide derivatives of dicarboxylic acid, sulfonic acid derivatives of dicarboxylic acids, selenic acid derivatives of dicarboxylic acid, perchloric acid derivatives of dicarboxylic acid, boric acid derivatives of dicarboxylic acid, synthetic equivalents thereof, and mixtures thereof.
4. The method of claim 3 wherein the carboxylic acid has the general formula:
wherein x and y are integers between 0 and 20 inclusive, with the sum of x and y being an integer of 20 or less, wherein R is a functionality selected from the group consisting of substituted or unsubstituted aromatic hydrocarbon groups, branched or unbranched alkyl groups, the alkyl group having between 1 and 27 carbon atoms, and mixtures thereof, and wherein each variable R', R'', R''' and R'''' is a functionality selected from the group consisting of hydrogen, amines, hydroxyl, phenyl, phenol radicals, and mixtures thereof, each of the above-mentioned R variable functionalities being chosen independently of the other R variable functionalities, and wherein R'' may also be selected from the group consisting of anhydrides, halide salts, selenic acid salts, perchloric acid salts, boric acid salts, and mixtures thereof; and wherein the dicarboxylic acid has the general formula:
wherein x is an integer between 1 and 20 inclusive and R
and R' are functionalities selected from the group consisting of hydrogen, hydroxyl radicals, amines, phenyl radicals and mixtures thereof.
wherein x and y are integers between 0 and 20 inclusive, with the sum of x and y being an integer of 20 or less, wherein R is a functionality selected from the group consisting of substituted or unsubstituted aromatic hydrocarbon groups, branched or unbranched alkyl groups, the alkyl group having between 1 and 27 carbon atoms, and mixtures thereof, and wherein each variable R', R'', R''' and R'''' is a functionality selected from the group consisting of hydrogen, amines, hydroxyl, phenyl, phenol radicals, and mixtures thereof, each of the above-mentioned R variable functionalities being chosen independently of the other R variable functionalities, and wherein R'' may also be selected from the group consisting of anhydrides, halide salts, selenic acid salts, perchloric acid salts, boric acid salts, and mixtures thereof; and wherein the dicarboxylic acid has the general formula:
wherein x is an integer between 1 and 20 inclusive and R
and R' are functionalities selected from the group consisting of hydrogen, hydroxyl radicals, amines, phenyl radicals and mixtures thereof.
5. The method of claim 3 wherein said contacting step occurs at a temperature between about 20°C and a temperature at which decomposition of the polymeric material commences.
6. The method of claim 5 wherein the polymeric material is selected from the group consisting of:
addition polymers selected from the group consisting of polyethylene, polypropylene, polystyrene, polyisobutylene, polyvinyl chloride, polyacrylonitrile, polymethyl acrylate, polymethyl methacrylate, polytetrafluoroethylene, polyformaldehyde, polyacetaldehyde, polyisoprene, and mixtures thereof;
condensation polymers selected from the group consisting of polyamides, polyesters, polyurethanes, polysiloxanes, polyphenolformaldehydes, ureaformaldehydes, melamine formaldehydes, celluloses, polysulfides, polyacetates, polycarbonates, and mixtures thereof;
thermoplastic elastomers selected from the group consisting of styrene-isoprene-styrene, styrene-butadiene-styrene, copolyesters, copolyester ethers, silicone-polyamides, silicone-polyesters, silicone-polyolefins, silicone-styrenes, aromatic polyether-urethanes, alpha cellulose filled ureas, polyvinyl chloride-acetates, vinylbutyrals, and mixtures thereof;
co-polymers selected from the group consisting of polyester-polyethers, polyether-polysiloxanes, polysiloxane-polyamides, polyesteramides, copolyamides, nylons, and mixtures thereof; and mixtures thereof.
addition polymers selected from the group consisting of polyethylene, polypropylene, polystyrene, polyisobutylene, polyvinyl chloride, polyacrylonitrile, polymethyl acrylate, polymethyl methacrylate, polytetrafluoroethylene, polyformaldehyde, polyacetaldehyde, polyisoprene, and mixtures thereof;
condensation polymers selected from the group consisting of polyamides, polyesters, polyurethanes, polysiloxanes, polyphenolformaldehydes, ureaformaldehydes, melamine formaldehydes, celluloses, polysulfides, polyacetates, polycarbonates, and mixtures thereof;
thermoplastic elastomers selected from the group consisting of styrene-isoprene-styrene, styrene-butadiene-styrene, copolyesters, copolyester ethers, silicone-polyamides, silicone-polyesters, silicone-polyolefins, silicone-styrenes, aromatic polyether-urethanes, alpha cellulose filled ureas, polyvinyl chloride-acetates, vinylbutyrals, and mixtures thereof;
co-polymers selected from the group consisting of polyester-polyethers, polyether-polysiloxanes, polysiloxane-polyamides, polyesteramides, copolyamides, nylons, and mixtures thereof; and mixtures thereof.
7. The method of claim 6 wherein the polymeric material is selected from the group consisting of polyethylenes, polypropylenes, polyesters, thermoplastic elastomers, and mixtures thereof.
8. The method of claim 7 wherein the polymeric material is a polyester selected from the group consisting of polybutylene terephthalate, polyethylene terephthalate, and mixtures thereof.
9. The method of claim 3 wherein said reacting step in which said oxidizing agent is reacted with said activating agent occurs in at least one of: an aqueous environment; an anhydrous environment; and a vaporous environment.
10. The method of claim 9 wherein the reaction between said oxidizing agent and said activating agent occurs at a rate essentially equal to reaction between said polymeric substrate and the reaction intermediate.
11. The method of claim 3 wherein the oxidizing agent is maintained in an aqueous solution at a concentration between about 0.25% and 25% by volume, and wherein the activating agent is maintained in said aqueous solution at a concentration between about 0.01%
and 5.00% by volume.
and 5.00% by volume.
12. The method of claim 1 wherein the polymeric material is a virgin polymeric material.
13. The method of claim 1 wherein the contacting step is carried out by spraying the composition onto at least one of a virgin polymeric material and a polymeric substrate with a heated spray gun.
14. The method of claim 1 wherein the composition is flash heated to form a reactive vapor, and the contacting step is carried out by exposing a polymeric substrate to the vapor for a period of time sufficient to render the substrate adhesive.
15. The method of claim 3 wherein the oxidizing agent and the activating agent are each in solid form, and wherein the method further comprises the step of placing the solid agents at the mouth of an injection molding press, wherein the contacting step occurs during molding of a virgin polymeric material into a polymeric substrate.
16. The method of claim 3 wherein the composition takes the form of at least one of: the oxidizing agent and the activating agent are each in solid form held in a suspension; and the oxidizing agent and the activating agent are in an aqueous solution; and wherein the method further comprises the step of spraying the composition onto the inner core of a tool of an injection molding press, wherein the contacting step occurs during molding of a virgin polymeric material into a polymeric substrate.
17. The method of claim 3 wherein the composition is flash heated to form a reactive vapor, and wherein the vapor is forced into a molding tool substantially immediately before closing the tool, wherein the contacting step occurs during molding of a virgin polymeric material into a polymeric substrate.
18. The method of claim 3 wherein the activating agent is selected from the group consisting of acetic anhydride, glacial acetic acid, vinegar, oxalic acid, formic acid, and mixtures thereof.
19. The method of claim 3 wherein the oxidizing agent is selected from the group consisting of sodium hypochlorite, calcium hypochlorite, calcium hypochlorite tetrahydrate, and mixtures thereof.
20. A method for improving adhesion characteristics of a polymeric material, comprising the steps of:
contacting the polymeric material with a composition containing at least one oxidizing agent, said oxidizing agent present in a kinetically degrading state which produces at least one chemical intermediate reactive with the polymeric substrate in a controlled reaction mechanism;
maintaining contact between the polymeric material and the composition for an interval sufficient to impart functional groups derived from said oxidizing agent into the polymeric material; and reacting said oxidizing agent with an activating agent which preferentially reacts with said oxidizing agent to produce said at least one intermediate reactive with the polymeric substrate;
wherein said oxidizing agent is a bivalent oxygen compound selected from the group consisting of oxycompounds of chlorine, oxycompounds of bromine, oxycompounds of iodine, oxycompounds of boron, oxycompounds of nitrogen and mixtures thereof;
and wherein said activating agent is selected from the group consisting of carboxylic acids, anhydride derivatives of carboxylic acids, acid halide derivatives of carboxylic acids, sulfonic acid derivatives of carboxylic acids, selenic acid derivatives of carboxylic acids, perchloric acid derivatives of carboxylic acid, boric acid derivatives of carboxylic acid, dicarboxylic acid, anhydride derivatives of dicarboxylic acid, acid halide derivatives of dicarboxylic acid, sulfonic acid derivatives of dicarboxylic acids, selenic acid derivatives of dicarboxylic acid, perchloric acid derivatives of dicarboxylic acid, boric acid derivatives of dicarboxylic acid, synthetic equivalents thereof, and mixtures thereof.
contacting the polymeric material with a composition containing at least one oxidizing agent, said oxidizing agent present in a kinetically degrading state which produces at least one chemical intermediate reactive with the polymeric substrate in a controlled reaction mechanism;
maintaining contact between the polymeric material and the composition for an interval sufficient to impart functional groups derived from said oxidizing agent into the polymeric material; and reacting said oxidizing agent with an activating agent which preferentially reacts with said oxidizing agent to produce said at least one intermediate reactive with the polymeric substrate;
wherein said oxidizing agent is a bivalent oxygen compound selected from the group consisting of oxycompounds of chlorine, oxycompounds of bromine, oxycompounds of iodine, oxycompounds of boron, oxycompounds of nitrogen and mixtures thereof;
and wherein said activating agent is selected from the group consisting of carboxylic acids, anhydride derivatives of carboxylic acids, acid halide derivatives of carboxylic acids, sulfonic acid derivatives of carboxylic acids, selenic acid derivatives of carboxylic acids, perchloric acid derivatives of carboxylic acid, boric acid derivatives of carboxylic acid, dicarboxylic acid, anhydride derivatives of dicarboxylic acid, acid halide derivatives of dicarboxylic acid, sulfonic acid derivatives of dicarboxylic acids, selenic acid derivatives of dicarboxylic acid, perchloric acid derivatives of dicarboxylic acid, boric acid derivatives of dicarboxylic acid, synthetic equivalents thereof, and mixtures thereof.
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/048,609 US6077913A (en) | 1998-03-26 | 1998-03-26 | Process for producing paintable polymeric articles |
| US09/048,609 | 1998-03-26 | ||
| US09/196,608 | 1998-11-03 | ||
| US09/196,608 US6100343A (en) | 1998-11-03 | 1998-11-03 | Process for producing paintable polymeric articles |
| PCT/US1999/006270 WO1999048933A1 (en) | 1998-03-26 | 1999-03-24 | Process for producing paintable polymeric articles |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2325732A1 true CA2325732A1 (en) | 1999-09-30 |
| CA2325732C CA2325732C (en) | 2011-01-11 |
Family
ID=26726320
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2325732A Expired - Fee Related CA2325732C (en) | 1998-03-26 | 1999-03-24 | Process for producing paintable polymeric articles |
Country Status (3)
| Country | Link |
|---|---|
| AU (1) | AU3198199A (en) |
| CA (1) | CA2325732C (en) |
| WO (1) | WO1999048933A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7022291B1 (en) * | 2002-03-22 | 2006-04-04 | Beholz Lars G | Apparatus for treating polymeric material to improve surface adhesion |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6125252B2 (en) * | 2012-02-10 | 2017-05-10 | 東洋ゴム工業株式会社 | Modified polymer production method and diene polymer |
| JP6125283B2 (en) * | 2013-03-07 | 2017-05-10 | 東洋ゴム工業株式会社 | Modified polymer production method and diene polymer |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2118580C3 (en) * | 1970-07-15 | 1974-11-21 | Nautschno-Issledowatel'skij Institut Resinowoj Promyschlennosti, Moskau | Improving the adhesiveness of surfaces of polymer plastics |
| US5053256A (en) * | 1988-11-03 | 1991-10-01 | Hercules Incorporated | Sodium hypochlorite surface treatment to improve the adhesion of paints to polydicyclopentadiene |
| US5232604A (en) * | 1990-01-31 | 1993-08-03 | Modar, Inc. | Process for the oxidation of materials in water at supercritical temperatures utilizing reaction rate enhancers |
| US5670582A (en) * | 1996-07-24 | 1997-09-23 | Exxon Chemical Patents Inc. | Process for halogenation of isomonoolefin/para-alkylstyrene copolymers |
-
1999
- 1999-03-24 AU AU31981/99A patent/AU3198199A/en not_active Abandoned
- 1999-03-24 WO PCT/US1999/006270 patent/WO1999048933A1/en active Application Filing
- 1999-03-24 CA CA2325732A patent/CA2325732C/en not_active Expired - Fee Related
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7022291B1 (en) * | 2002-03-22 | 2006-04-04 | Beholz Lars G | Apparatus for treating polymeric material to improve surface adhesion |
Also Published As
| Publication number | Publication date |
|---|---|
| AU3198199A (en) | 1999-10-18 |
| CA2325732C (en) | 2011-01-11 |
| WO1999048933A1 (en) | 1999-09-30 |
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