CA2503217A1 - Use of hyperbranched polymers comprising urethane and/or urea groups for modifying surfaces - Google Patents
Use of hyperbranched polymers comprising urethane and/or urea groups for modifying surfaces Download PDFInfo
- Publication number
- CA2503217A1 CA2503217A1 CA 2503217 CA2503217A CA2503217A1 CA 2503217 A1 CA2503217 A1 CA 2503217A1 CA 2503217 CA2503217 CA 2503217 CA 2503217 A CA2503217 A CA 2503217A CA 2503217 A1 CA2503217 A1 CA 2503217A1
- Authority
- CA
- Canada
- Prior art keywords
- groups
- polymers
- compounds
- hyperbranched
- substrate
- 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.)
- Abandoned
Links
- 229920000587 hyperbranched polymer Polymers 0.000 title claims abstract description 57
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 title claims abstract description 27
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 title claims abstract description 25
- 239000000758 substrate Substances 0.000 claims abstract description 39
- 238000000034 method Methods 0.000 claims abstract description 28
- 150000001875 compounds Chemical class 0.000 claims description 53
- 239000000203 mixture Substances 0.000 claims description 43
- 238000006243 chemical reaction Methods 0.000 claims description 34
- 125000000524 functional group Chemical group 0.000 claims description 23
- 239000000463 material Substances 0.000 claims description 14
- 230000008569 process Effects 0.000 claims description 14
- 239000004753 textile Substances 0.000 claims description 13
- 230000000295 complement effect Effects 0.000 claims description 10
- 229920002994 synthetic fiber Polymers 0.000 claims description 9
- 238000007259 addition reaction Methods 0.000 claims description 8
- 238000006482 condensation reaction Methods 0.000 claims description 7
- 239000012209 synthetic fiber Substances 0.000 claims description 6
- 239000002985 plastic film Substances 0.000 claims description 4
- 229920006255 plastic film Polymers 0.000 claims description 4
- 125000001165 hydrophobic group Chemical group 0.000 claims description 3
- 238000010137 moulding (plastic) Methods 0.000 claims description 2
- 229920000642 polymer Polymers 0.000 abstract description 81
- -1 polypropylene Polymers 0.000 description 75
- 239000004814 polyurethane Substances 0.000 description 42
- 229920002635 polyurethane Polymers 0.000 description 40
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 38
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 33
- 229920001577 copolymer Polymers 0.000 description 32
- 229920002396 Polyurea Polymers 0.000 description 26
- 239000004743 Polypropylene Substances 0.000 description 25
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 17
- 230000002209 hydrophobic effect Effects 0.000 description 16
- 239000012948 isocyanate Substances 0.000 description 15
- 239000007788 liquid Substances 0.000 description 15
- 239000000178 monomer Substances 0.000 description 15
- 229920000728 polyester Polymers 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- 239000004952 Polyamide Substances 0.000 description 14
- 150000001412 amines Chemical class 0.000 description 14
- 150000002513 isocyanates Chemical class 0.000 description 14
- 229920002647 polyamide Polymers 0.000 description 14
- 239000005056 polyisocyanate Substances 0.000 description 13
- 229920001228 polyisocyanate Polymers 0.000 description 13
- 229920001155 polypropylene Polymers 0.000 description 13
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 12
- 239000004698 Polyethylene Substances 0.000 description 11
- 230000004048 modification Effects 0.000 description 11
- 238000012986 modification Methods 0.000 description 11
- 239000004745 nonwoven fabric Substances 0.000 description 11
- 229920000573 polyethylene Polymers 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 150000001298 alcohols Chemical class 0.000 description 10
- 239000004800 polyvinyl chloride Substances 0.000 description 10
- 229920000915 polyvinyl chloride Polymers 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- 238000000576 coating method Methods 0.000 description 9
- 229920001684 low density polyethylene Polymers 0.000 description 9
- 239000004702 low-density polyethylene Substances 0.000 description 9
- 229920002857 polybutadiene Polymers 0.000 description 9
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 9
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
- 239000005062 Polybutadiene Substances 0.000 description 8
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- 239000000412 dendrimer Substances 0.000 description 8
- 229920000736 dendritic polymer Polymers 0.000 description 8
- 238000001035 drying Methods 0.000 description 8
- 239000000835 fiber Substances 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- 238000010521 absorption reaction Methods 0.000 description 7
- XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 description 7
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 229920001971 elastomer Polymers 0.000 description 7
- 239000004744 fabric Substances 0.000 description 7
- 229920003023 plastic Polymers 0.000 description 7
- 239000004033 plastic Substances 0.000 description 7
- 238000006116 polymerization reaction Methods 0.000 description 7
- 229920006324 polyoxymethylene Polymers 0.000 description 7
- 230000009257 reactivity Effects 0.000 description 7
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 235000014113 dietary fatty acids Nutrition 0.000 description 6
- 239000000194 fatty acid Substances 0.000 description 6
- 229930195729 fatty acid Natural products 0.000 description 6
- 150000004665 fatty acids Chemical class 0.000 description 6
- 238000000465 moulding Methods 0.000 description 6
- 239000000123 paper Substances 0.000 description 6
- 229920002239 polyacrylonitrile Polymers 0.000 description 6
- 229920000098 polyolefin Polymers 0.000 description 6
- 229920002554 vinyl polymer Polymers 0.000 description 6
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 5
- 229920002302 Nylon 6,6 Polymers 0.000 description 5
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 5
- 239000000853 adhesive Substances 0.000 description 5
- 230000001070 adhesive effect Effects 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 150000001993 dienes Chemical class 0.000 description 5
- 125000005442 diisocyanate group Chemical group 0.000 description 5
- 239000000806 elastomer Substances 0.000 description 5
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 5
- 229920001903 high density polyethylene Polymers 0.000 description 5
- 239000004700 high-density polyethylene Substances 0.000 description 5
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 5
- 239000004417 polycarbonate Substances 0.000 description 5
- 229920001451 polypropylene glycol Polymers 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 230000002194 synthesizing effect Effects 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 4
- 229920002943 EPDM rubber Polymers 0.000 description 4
- 239000005058 Isophorone diisocyanate Substances 0.000 description 4
- 229920000877 Melamine resin Polymers 0.000 description 4
- 229920002292 Nylon 6 Polymers 0.000 description 4
- 239000004721 Polyphenylene oxide Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 150000008064 anhydrides Chemical class 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 239000004922 lacquer Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 4
- 229920002285 poly(styrene-co-acrylonitrile) Polymers 0.000 description 4
- 229920005862 polyol Polymers 0.000 description 4
- 150000003077 polyols Chemical class 0.000 description 4
- 229920006380 polyphenylene oxide Polymers 0.000 description 4
- 239000004810 polytetrafluoroethylene Substances 0.000 description 4
- 229940058401 polytetrafluoroethylene Drugs 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- 229920001169 thermoplastic Polymers 0.000 description 4
- 239000004416 thermosoftening plastic Substances 0.000 description 4
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- 239000002023 wood Substances 0.000 description 4
- FJLUATLTXUNBOT-UHFFFAOYSA-N 1-Hexadecylamine Chemical compound CCCCCCCCCCCCCCCCN FJLUATLTXUNBOT-UHFFFAOYSA-N 0.000 description 3
- PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 239000012975 dibutyltin dilaurate Substances 0.000 description 3
- 150000001991 dicarboxylic acids Chemical class 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 229920006242 ethylene acrylic acid copolymer Polymers 0.000 description 3
- 239000006260 foam Substances 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 230000005661 hydrophobic surface Effects 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 150000005673 monoalkenes Chemical class 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000003973 paint Substances 0.000 description 3
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 3
- 229920000768 polyamine Polymers 0.000 description 3
- 229920001707 polybutylene terephthalate Polymers 0.000 description 3
- 229920000570 polyether Polymers 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 3
- 125000006239 protecting group Chemical group 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 238000007789 sealing Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 239000013638 trimer Substances 0.000 description 3
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 3
- PCHXZXKMYCGVFA-UHFFFAOYSA-N 1,3-diazetidine-2,4-dione Chemical compound O=C1NC(=O)N1 PCHXZXKMYCGVFA-UHFFFAOYSA-N 0.000 description 2
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- ZDHCZVWCTKTBRY-UHFFFAOYSA-N 12-hydroxylauric acid Chemical compound OCCCCCCCCCCCC(O)=O ZDHCZVWCTKTBRY-UHFFFAOYSA-N 0.000 description 2
- DETXZQGDWUJKMO-UHFFFAOYSA-N 2-hydroxymethanesulfonic acid Chemical compound OCS(O)(=O)=O DETXZQGDWUJKMO-UHFFFAOYSA-N 0.000 description 2
- RDFQSFOGKVZWKF-UHFFFAOYSA-N 3-hydroxy-2,2-dimethylpropanoic acid Chemical compound OCC(C)(C)C(O)=O RDFQSFOGKVZWKF-UHFFFAOYSA-N 0.000 description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- 229920001634 Copolyester Polymers 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical class C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- 229920010126 Linear Low Density Polyethylene (LLDPE) Polymers 0.000 description 2
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 2
- OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 2
- 239000004435 Oxo alcohol Substances 0.000 description 2
- 229920007019 PC/ABS Polymers 0.000 description 2
- 229920002367 Polyisobutene Polymers 0.000 description 2
- 240000005319 Sedum acre Species 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 229920001807 Urea-formaldehyde Polymers 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 229920000800 acrylic rubber Polymers 0.000 description 2
- 229920002877 acrylic styrene acrylonitrile Polymers 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 229920000180 alkyd Polymers 0.000 description 2
- 239000002168 alkylating agent Substances 0.000 description 2
- 229940100198 alkylating agent Drugs 0.000 description 2
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000001414 amino alcohols Chemical class 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 150000005840 aryl radicals Chemical class 0.000 description 2
- HIFVAOIJYDXIJG-UHFFFAOYSA-N benzylbenzene;isocyanic acid Chemical class N=C=O.N=C=O.C=1C=CC=CC=1CC1=CC=CC=C1 HIFVAOIJYDXIJG-UHFFFAOYSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 2
- 229920001400 block copolymer Polymers 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 description 2
- 150000001718 carbodiimides Chemical class 0.000 description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
- 125000002843 carboxylic acid group Chemical group 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 229920006037 cross link polymer Polymers 0.000 description 2
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 150000002118 epoxides Chemical class 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 238000007306 functionalization reaction Methods 0.000 description 2
- 239000004746 geotextile Substances 0.000 description 2
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 2
- GOQYKNQRPGWPLP-UHFFFAOYSA-N heptadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 150000002433 hydrophilic molecules Chemical class 0.000 description 2
- 230000005660 hydrophilic surface Effects 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 229920000554 ionomer Polymers 0.000 description 2
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 2
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 229920000126 latex Polymers 0.000 description 2
- 239000010985 leather Substances 0.000 description 2
- 229920000092 linear low density polyethylene Polymers 0.000 description 2
- 239000004707 linear low-density polyethylene Substances 0.000 description 2
- 230000005923 long-lasting effect Effects 0.000 description 2
- 229920001179 medium density polyethylene Polymers 0.000 description 2
- 239000004701 medium-density polyethylene Substances 0.000 description 2
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 239000003607 modifier Substances 0.000 description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
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Classifications
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- 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
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- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2323/00—Characterised by the use of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Derivatives of such polymers
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- C08J2323/10—Homopolymers or copolymers of propene
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
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- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
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Landscapes
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- Life Sciences & Earth Sciences (AREA)
- Manufacturing & Machinery (AREA)
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2002149841 DE10249841A1 (de) | 2002-10-25 | 2002-10-25 | Verwendung von hyperverzweigten Polymeren, die Urethan- und/oder Harnstoffgruppen aufweisen, zur Modifizierung von Oberflächen |
| DE10249841.5 | 2002-10-25 | ||
| PCT/EP2003/011824 WO2004037881A1 (de) | 2002-10-25 | 2003-10-24 | Verwendung von hyperverzweigten polymeren, die urethan- und/oder harnstoffgruppen aufweisen, zur modifizierung von oberflächen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2503217A1 true CA2503217A1 (en) | 2004-05-06 |
Family
ID=32103026
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA 2503217 Abandoned CA2503217A1 (en) | 2002-10-25 | 2003-10-24 | Use of hyperbranched polymers comprising urethane and/or urea groups for modifying surfaces |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US20060035091A1 (https=) |
| EP (1) | EP1558660A1 (https=) |
| JP (1) | JP2006503947A (https=) |
| AU (1) | AU2003289852A1 (https=) |
| BR (1) | BR0315557A (https=) |
| CA (1) | CA2503217A1 (https=) |
| DE (1) | DE10249841A1 (https=) |
| MX (1) | MXPA05003910A (https=) |
| WO (1) | WO2004037881A1 (https=) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI279226B (en) * | 2004-07-20 | 2007-04-21 | Schoeller Textil Ag | Dressings which can be applied several times to textile fibres and textile fabrics |
| TW200615424A (en) * | 2004-07-20 | 2006-05-16 | Schoeller Textil Ag | Finishings for textile fibres and babrics to give hydrophobic oleophobic and self-cleaning surfaces |
| US20090041813A1 (en) | 2005-02-21 | 2009-02-12 | Basf Aktiengesellschaft | Active substance composition comprising at least one nitrogen atom-containing, hyperbranched polymer |
| EP1950250A4 (en) * | 2005-10-25 | 2012-01-04 | Kyusyu University | POLYMER STRUCTURE WITH MODIFIED SURFACE AND / OR BORDER AREA AND METHOD OF MANUFACTURING THEREOF |
| WO2007074790A1 (ja) * | 2005-12-26 | 2007-07-05 | Nisshinbo Industries, Inc. | ポリオレフィン・ポリエステル系フィルム |
| JP5328370B2 (ja) * | 2006-01-17 | 2013-10-30 | ビーエーエスエフ ソシエタス・ヨーロピア | 木質材料においてホルムアルデヒド放散を減少させるための方法 |
| CN101405661A (zh) * | 2006-03-22 | 2009-04-08 | 巴斯夫欧洲公司 | 涂覆有支化聚氨酯并用于电子照相印花法的基质 |
| DE102006055763B4 (de) * | 2006-11-21 | 2011-06-22 | Militz, Detlef, 15366 | Verfahren zur Metallisierung von Polyester, metallisierter Polyester und dessen Verwendung |
| JP5430396B2 (ja) * | 2007-04-25 | 2014-02-26 | 日産化学工業株式会社 | 表面改質されたポリマー構造体の製造方法 |
| RU2012126318A (ru) * | 2009-11-27 | 2014-01-10 | Басф Се | Дендритная полимочевина для солюбилизации труднорастворимых действующих веществ |
| JP5670815B2 (ja) * | 2011-04-21 | 2015-02-18 | 花王株式会社 | 衣料用処理剤組成物 |
| JP6277591B2 (ja) * | 2013-03-18 | 2018-02-14 | 東レ株式会社 | シート状物およびその製造方法 |
| JP2015214693A (ja) * | 2014-04-25 | 2015-12-03 | ミドリ安全株式会社 | 耐久性に優れた防曇性コーティング被覆物品 |
| SG10201902820UA (en) * | 2014-10-10 | 2019-04-29 | Nipsea Tech Pte Ltd | A polymer composition and preparation method thereof |
| NL2017429B1 (en) * | 2016-09-07 | 2018-03-27 | Van Wijhe Verf B V | Antimicrobial surfactants and water borne coatings comprising the same. |
| US11118003B2 (en) | 2017-11-15 | 2021-09-14 | Board Of Trustees Of Michigan State University | Omniphobic polyurethane compositions, related articles, and related methods |
| WO2020142578A1 (en) * | 2019-01-02 | 2020-07-09 | Board Of Trustees Of Michigan State University | Self-healing, self-cleaning omniphobic composition, related articles and related methods |
| WO2020160089A1 (en) | 2019-01-31 | 2020-08-06 | Board Of Trustees Of Michigan State University | Self-healing laminate composition, related articles and related methods |
| WO2020180760A1 (en) * | 2019-03-05 | 2020-09-10 | Board Of Trustees Of Michigan State University | Omniphobic polyurethane compositions, related articles, and related methods |
| CN114854253B (zh) * | 2022-06-02 | 2023-02-07 | 江苏利信新型建筑模板有限公司 | 一种覆膜建筑铝合金模板及其制备方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE9200564L (sv) * | 1992-02-26 | 1993-03-15 | Perstorp Ab | Dendritisk makromolekyl av polyestertyp, foerfarande foer framstaellning daerav samt anvaendning daerav |
| DE19524045A1 (de) * | 1995-07-01 | 1997-01-02 | Basf Ag | Hochfunktionalisierte Polyurethane |
| US5798418A (en) * | 1995-07-31 | 1998-08-25 | Fmc Corporation | Star polymers from mixed initiators |
| US5936055A (en) * | 1997-02-19 | 1999-08-10 | The Dow Chemical Company | Acid functionalized polyurethane adducts |
| DE19904444A1 (de) * | 1999-02-04 | 2000-08-10 | Basf Ag | Dendrimere und hochverzweigte Polyurethane |
| SK5132003A3 (en) * | 2000-10-31 | 2003-09-11 | Basf Ag | Use of hyperbranched polyurethanes for producing printing inks |
| BR0114934A (pt) * | 2000-10-31 | 2004-01-06 | Basf Drucksysteme Gmbh | Tinta de impressão lìquida para a impressão flexográfica ou de gravura, verniz de impressão para o revestimento de meios de impressão não impressos ou para o recobrimento de meios de impressão impressos, e, uso de polìmeros hiperramificados |
| DE10056183A1 (de) * | 2000-11-13 | 2002-05-29 | Basf Ag | Hochverzweigte Polymere zur Antiknitterausrüstung von cellulosehaltigen Textilien |
| DE10109803A1 (de) * | 2001-03-01 | 2002-09-05 | Basf Ag | Verwendung von anionischen Polymeren, die Urethan- und/oder Harnstoffgruppen aufweisen, zur Modifizierung von Oberflächen |
| DE10203058A1 (de) * | 2002-01-26 | 2003-07-31 | Bayer Ag | Dentritisch modifizierte Polyurethane |
-
2002
- 2002-10-25 DE DE2002149841 patent/DE10249841A1/de not_active Withdrawn
-
2003
- 2003-10-24 CA CA 2503217 patent/CA2503217A1/en not_active Abandoned
- 2003-10-24 BR BR0315557-9A patent/BR0315557A/pt not_active IP Right Cessation
- 2003-10-24 JP JP2004545978A patent/JP2006503947A/ja active Pending
- 2003-10-24 MX MXPA05003910A patent/MXPA05003910A/es unknown
- 2003-10-24 US US10/532,247 patent/US20060035091A1/en not_active Abandoned
- 2003-10-24 EP EP03782180A patent/EP1558660A1/de not_active Withdrawn
- 2003-10-24 AU AU2003289852A patent/AU2003289852A1/en not_active Abandoned
- 2003-10-24 WO PCT/EP2003/011824 patent/WO2004037881A1/de not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| EP1558660A1 (de) | 2005-08-03 |
| US20060035091A1 (en) | 2006-02-16 |
| WO2004037881A1 (de) | 2004-05-06 |
| BR0315557A (pt) | 2005-08-23 |
| AU2003289852A1 (en) | 2004-05-13 |
| MXPA05003910A (es) | 2005-06-17 |
| JP2006503947A (ja) | 2006-02-02 |
| DE10249841A1 (de) | 2004-05-13 |
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| Date | Code | Title | Description |
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| EEER | Examination request | ||
| FZDE | Discontinued |