US20210230395A1 - Solid polymeric articles having hydrophobic compounds intermixed therein - Google Patents
Solid polymeric articles having hydrophobic compounds intermixed therein Download PDFInfo
- Publication number
- US20210230395A1 US20210230395A1 US17/228,835 US202117228835A US2021230395A1 US 20210230395 A1 US20210230395 A1 US 20210230395A1 US 202117228835 A US202117228835 A US 202117228835A US 2021230395 A1 US2021230395 A1 US 2021230395A1
- Authority
- US
- United States
- Prior art keywords
- copolymers
- polymeric article
- independently
- fluorinated
- poly
- 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
- 150000001875 compounds Chemical class 0.000 title claims abstract description 72
- 230000002209 hydrophobic effect Effects 0.000 title claims abstract description 53
- 239000007787 solid Substances 0.000 title claims abstract description 39
- 239000000203 mixture Substances 0.000 claims abstract description 68
- 229920000642 polymer Polymers 0.000 claims abstract description 46
- 230000000694 effects Effects 0.000 claims abstract description 29
- -1 poly(acrylic acid) Polymers 0.000 claims description 73
- 125000000217 alkyl group Chemical group 0.000 claims description 28
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 26
- 239000003795 chemical substances by application Substances 0.000 claims description 20
- 230000005661 hydrophobic surface Effects 0.000 claims description 14
- 229920000058 polyacrylate Polymers 0.000 claims description 14
- 150000001298 alcohols Chemical class 0.000 claims description 9
- 239000007788 liquid Substances 0.000 claims description 8
- 239000002952 polymeric resin Substances 0.000 claims description 8
- 239000004793 Polystyrene Substances 0.000 claims description 7
- 229920002223 polystyrene Polymers 0.000 claims description 7
- 229920003002 synthetic resin Polymers 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 6
- 229920000728 polyester Polymers 0.000 claims description 6
- 229920000193 polymethacrylate Polymers 0.000 claims description 6
- 150000003673 urethanes Chemical class 0.000 claims description 6
- 229920002319 Poly(methyl acrylate) Polymers 0.000 claims description 5
- 239000004952 Polyamide Substances 0.000 claims description 5
- 229920002125 Sokalan® Polymers 0.000 claims description 5
- 229920003229 poly(methyl methacrylate) Polymers 0.000 claims description 5
- 229920002647 polyamide Polymers 0.000 claims description 5
- 229920001610 polycaprolactone Polymers 0.000 claims description 5
- 239000004417 polycarbonate Substances 0.000 claims description 5
- 229920000515 polycarbonate Polymers 0.000 claims description 5
- 239000004926 polymethyl methacrylate Substances 0.000 claims description 5
- 229920001296 polysiloxane Polymers 0.000 claims description 5
- 229920000915 polyvinyl chloride Polymers 0.000 claims description 5
- 239000004800 polyvinyl chloride Substances 0.000 claims description 5
- 230000009969 flowable effect Effects 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 229920002803 thermoplastic polyurethane Polymers 0.000 claims description 4
- 229920005992 thermoplastic resin Polymers 0.000 claims description 4
- 229920006125 amorphous polymer Polymers 0.000 claims description 3
- 229920001973 fluoroelastomer Polymers 0.000 claims description 3
- 229920005989 resin Polymers 0.000 claims description 3
- 239000011347 resin Substances 0.000 claims description 3
- 229920002725 thermoplastic elastomer Polymers 0.000 claims description 3
- 239000004634 thermosetting polymer Substances 0.000 claims description 3
- 125000000129 anionic group Chemical group 0.000 claims description 2
- 125000002091 cationic group Chemical group 0.000 claims description 2
- 238000000465 moulding Methods 0.000 claims description 2
- 125000002467 phosphate group Chemical class [H]OP(=O)(O[H])O[*] 0.000 claims description 2
- 238000007711 solidification Methods 0.000 claims description 2
- 230000008023 solidification Effects 0.000 claims description 2
- 238000009987 spinning Methods 0.000 claims description 2
- 238000003856 thermoforming Methods 0.000 claims description 2
- 239000001993 wax Chemical class 0.000 claims description 2
- 229920001971 elastomer Polymers 0.000 claims 2
- 239000000806 elastomer Substances 0.000 claims 2
- 239000004632 polycaprolactone Substances 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 4
- 125000004122 cyclic group Chemical group 0.000 abstract description 3
- 125000001165 hydrophobic group Chemical group 0.000 abstract 1
- 239000002253 acid Substances 0.000 description 13
- 239000000758 substrate Substances 0.000 description 12
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 11
- 238000012360 testing method Methods 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 239000000463 material Substances 0.000 description 10
- 229920000136 polysorbate Polymers 0.000 description 9
- IJCWFDPJFXGQBN-RYNSOKOISA-N [(2R)-2-[(2R,3R,4S)-4-hydroxy-3-octadecanoyloxyoxolan-2-yl]-2-octadecanoyloxyethyl] octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCCCCCCCCCCCC)[C@H]1OC[C@H](O)[C@H]1OC(=O)CCCCCCCCCCCCCCCCC IJCWFDPJFXGQBN-RYNSOKOISA-N 0.000 description 8
- 0 *OC.*OCC(O*)C1CCC(C(C*O)O*)O1 Chemical compound *OC.*OCC(O*)C1CCC(C(C*O)O*)O1 0.000 description 7
- 229920002313 fluoropolymer Polymers 0.000 description 7
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical class C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 6
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 6
- 239000000654 additive Substances 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- 229940068965 polysorbates Drugs 0.000 description 6
- 150000001720 carbohydrates Chemical class 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 229930195729 fatty acid Natural products 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- 150000004665 fatty acids Chemical class 0.000 description 5
- 239000000835 fiber Substances 0.000 description 5
- 239000012530 fluid Substances 0.000 description 5
- 150000002596 lactones Chemical class 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 5
- 239000001589 sorbitan tristearate Substances 0.000 description 5
- 229960004129 sorbitan tristearate Drugs 0.000 description 5
- 235000011078 sorbitan tristearate Nutrition 0.000 description 5
- 238000010998 test method Methods 0.000 description 5
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 4
- JLIDVCMBCGBIEY-UHFFFAOYSA-N 1-penten-3-one Chemical compound CCC(=O)C=C JLIDVCMBCGBIEY-UHFFFAOYSA-N 0.000 description 4
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 4
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 4
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 4
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 4
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 4
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 4
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 4
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 4
- 239000005871 repellent Substances 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
- 239000004698 Polyethylene Substances 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 235000016213 coffee Nutrition 0.000 description 3
- 235000013353 coffee beverage Nutrition 0.000 description 3
- 230000006835 compression Effects 0.000 description 3
- 238000007906 compression Methods 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 239000002285 corn oil Substances 0.000 description 3
- 235000005687 corn oil Nutrition 0.000 description 3
- 150000001993 dienes Chemical class 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000013538 functional additive Substances 0.000 description 3
- 235000019674 grape juice Nutrition 0.000 description 3
- 235000008960 ketchup Nutrition 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 3
- 239000004810 polytetrafluoroethylene Substances 0.000 description 3
- 239000002689 soil Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 150000005846 sugar alcohols Chemical class 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 229920001169 thermoplastic Polymers 0.000 description 3
- LIFLRQVHKGGNSG-UHFFFAOYSA-N 2,3-dichlorobuta-1,3-diene Chemical compound ClC(=C)C(Cl)=C LIFLRQVHKGGNSG-UHFFFAOYSA-N 0.000 description 2
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 2
- SJWKGDGUQTWDRV-UHFFFAOYSA-N 2-Propenyl heptanoate Chemical compound CCCCCCC(=O)OCC=C SJWKGDGUQTWDRV-UHFFFAOYSA-N 0.000 description 2
- RCSBILYQLVXLJG-UHFFFAOYSA-N 2-Propenyl hexanoate Chemical compound CCCCCC(=O)OCC=C RCSBILYQLVXLJG-UHFFFAOYSA-N 0.000 description 2
- PZGMUSDNQDCNAG-UHFFFAOYSA-N 2-Propenyl octanoate Chemical compound CCCCCCCC(=O)OCC=C PZGMUSDNQDCNAG-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- 235000021357 Behenic acid Nutrition 0.000 description 2
- 241000219198 Brassica Species 0.000 description 2
- 235000003351 Brassica cretica Nutrition 0.000 description 2
- 235000003343 Brassica rupestris Nutrition 0.000 description 2
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 2
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 2
- WQZGKKKJIJFFOK-WHZQZERISA-N D-aldose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-WHZQZERISA-N 0.000 description 2
- WQZGKKKJIJFFOK-IVMDWMLBSA-N D-allopyranose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@H](O)[C@@H]1O WQZGKKKJIJFFOK-IVMDWMLBSA-N 0.000 description 2
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 description 2
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- 229920010499 Hytrel® 3078 Polymers 0.000 description 2
- KLDXJTOLSGUMSJ-JGWLITMVSA-N Isosorbide Chemical compound O[C@@H]1CO[C@@H]2[C@@H](O)CO[C@@H]21 KLDXJTOLSGUMSJ-JGWLITMVSA-N 0.000 description 2
- WQZGKKKJIJFFOK-VSOAQEOCSA-N L-altropyranose Chemical compound OC[C@@H]1OC(O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-VSOAQEOCSA-N 0.000 description 2
- 239000005639 Lauric acid Substances 0.000 description 2
- 235000021353 Lignoceric acid Nutrition 0.000 description 2
- CQXMAMUUWHYSIY-UHFFFAOYSA-N Lignoceric acid Natural products CCCCCCCCCCCCCCCCCCCCCCCC(=O)OCCC1=CC=C(O)C=C1 CQXMAMUUWHYSIY-UHFFFAOYSA-N 0.000 description 2
- CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 description 2
- 235000021314 Palmitic acid Nutrition 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
- 150000003926 acrylamides Chemical class 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 2
- 229940116226 behenic acid Drugs 0.000 description 2
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 2
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 2
- INLLPKCGLOXCIV-UHFFFAOYSA-N bromoethene Chemical compound BrC=C INLLPKCGLOXCIV-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 description 2
- 239000000571 coke Substances 0.000 description 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- GLVVKKSPKXTQRB-UHFFFAOYSA-N ethenyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OC=C GLVVKKSPKXTQRB-UHFFFAOYSA-N 0.000 description 2
- AFSIMBWBBOJPJG-UHFFFAOYSA-N ethenyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC=C AFSIMBWBBOJPJG-UHFFFAOYSA-N 0.000 description 2
- QBDADGJLZNIRFQ-UHFFFAOYSA-N ethenyl octanoate Chemical compound CCCCCCCC(=O)OC=C QBDADGJLZNIRFQ-UHFFFAOYSA-N 0.000 description 2
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 2
- FARYTWBWLZAXNK-WAYWQWQTSA-N ethyl (z)-3-(methylamino)but-2-enoate Chemical compound CCOC(=O)\C=C(\C)NC FARYTWBWLZAXNK-WAYWQWQTSA-N 0.000 description 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical compound FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 description 2
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 2
- PBZROIMXDZTJDF-UHFFFAOYSA-N hepta-1,6-dien-4-one Chemical compound C=CCC(=O)CC=C PBZROIMXDZTJDF-UHFFFAOYSA-N 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- 229960002479 isosorbide Drugs 0.000 description 2
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 235000010460 mustard Nutrition 0.000 description 2
- DNTMQTKDNSEIFO-UHFFFAOYSA-N n-(hydroxymethyl)-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NCO DNTMQTKDNSEIFO-UHFFFAOYSA-N 0.000 description 2
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- FSAJWMJJORKPKS-UHFFFAOYSA-N octadecyl prop-2-enoate Chemical class CCCCCCCCCCCCCCCCCCOC(=O)C=C FSAJWMJJORKPKS-UHFFFAOYSA-N 0.000 description 2
- 229960002446 octanoic acid Drugs 0.000 description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 2
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical compound [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 0.000 description 2
- 229920000098 polyolefin Polymers 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 229950008882 polysorbate Drugs 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 230000002940 repellent Effects 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- 239000004416 thermosoftening plastic Substances 0.000 description 2
- 229920001567 vinyl ester resin Polymers 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- FUSUHKVFWTUUBE-UHFFFAOYSA-N vinyl methyl ketone Natural products CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- MCHWWJLLPNDHGL-KVTDHHQDSA-N (2r,3s,4s,5r)-2,5-bis(hydroxymethyl)oxolane-3,4-diol Chemical compound OC[C@H]1O[C@H](CO)[C@@H](O)[C@@H]1O MCHWWJLLPNDHGL-KVTDHHQDSA-N 0.000 description 1
- MCHWWJLLPNDHGL-JGWLITMVSA-N (2s,3s,4s,5r)-2,5-bis(hydroxymethyl)oxolane-3,4-diol Chemical compound OC[C@H]1O[C@@H](CO)[C@@H](O)[C@@H]1O MCHWWJLLPNDHGL-JGWLITMVSA-N 0.000 description 1
- MCHWWJLLPNDHGL-UNTFVMJOSA-N (2s,3s,4s,5s)-2,5-bis(hydroxymethyl)oxolane-3,4-diol Chemical compound OC[C@@H]1O[C@@H](CO)[C@@H](O)[C@@H]1O MCHWWJLLPNDHGL-UNTFVMJOSA-N 0.000 description 1
- RBNPOMFGQQGHHO-UHFFFAOYSA-N -2,3-Dihydroxypropanoic acid Natural products OCC(O)C(O)=O RBNPOMFGQQGHHO-UHFFFAOYSA-N 0.000 description 1
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 1
- 229940084778 1,4-sorbitan Drugs 0.000 description 1
- MSWZFWKMSRAUBD-GASJEMHNSA-N 2-amino-2-deoxy-D-galactopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@H](O)[C@@H]1O MSWZFWKMSRAUBD-GASJEMHNSA-N 0.000 description 1
- MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 235000016795 Cola Nutrition 0.000 description 1
- 235000011824 Cola pachycarpa Nutrition 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- WQZGKKKJIJFFOK-CBPJZXOFSA-N D-Gulose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@H](O)[C@H]1O WQZGKKKJIJFFOK-CBPJZXOFSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- PHOQVHQSTUBQQK-SQOUGZDYSA-N D-glucono-1,5-lactone Chemical compound OC[C@H]1OC(=O)[C@H](O)[C@@H](O)[C@@H]1O PHOQVHQSTUBQQK-SQOUGZDYSA-N 0.000 description 1
- HSNZZMHEPUFJNZ-QMTIVRBISA-N D-keto-manno-heptulose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)C(=O)CO HSNZZMHEPUFJNZ-QMTIVRBISA-N 0.000 description 1
- QXKAIJAYHKCRRA-UHFFFAOYSA-N D-lyxonic acid Natural products OCC(O)C(O)C(O)C(O)=O QXKAIJAYHKCRRA-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- 229930091371 Fructose Natural products 0.000 description 1
- 239000005715 Fructose Substances 0.000 description 1
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
- SQUHHTBVTRBESD-UHFFFAOYSA-N Hexa-Ac-myo-Inositol Natural products CC(=O)OC1C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C1OC(C)=O SQUHHTBVTRBESD-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-YIDFTEPTSA-N IDOSE Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@H](O)[C@H]1O WQZGKKKJIJFFOK-YIDFTEPTSA-N 0.000 description 1
- 208000007976 Ketosis Diseases 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- 229920002302 Nylon 6,6 Polymers 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004772 Sontara Substances 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 229920006243 acrylic copolymer Polymers 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 150000001323 aldoses Chemical class 0.000 description 1
- ZOJBYZNEUISWFT-UHFFFAOYSA-N allyl isothiocyanate Chemical compound C=CCN=C=S ZOJBYZNEUISWFT-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 description 1
- SRBFZHDQGSBBOR-STGXQOJASA-N alpha-D-lyxopyranose Chemical compound O[C@@H]1CO[C@H](O)[C@@H](O)[C@H]1O SRBFZHDQGSBBOR-STGXQOJASA-N 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 125000006162 fluoroaliphatic group Chemical group 0.000 description 1
- 229930182830 galactose Natural products 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229960002442 glucosamine Drugs 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002386 heptoses Chemical class 0.000 description 1
- 150000002402 hexoses Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 1
- CDAISMWEOUEBRE-GPIVLXJGSA-N inositol Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H]1O CDAISMWEOUEBRE-GPIVLXJGSA-N 0.000 description 1
- 229960000367 inositol Drugs 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 150000002584 ketoses Chemical class 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000001151 other effect Effects 0.000 description 1
- 125000006353 oxyethylene group Chemical group 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 150000002972 pentoses Chemical class 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 229920000747 poly(lactic acid) Polymers 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 239000004626 polylactic acid Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920005606 polypropylene copolymer Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 229960002920 sorbitol Drugs 0.000 description 1
- 238000007655 standard test method Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000037072 sun protection Effects 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 150000003538 tetroses Chemical class 0.000 description 1
- 229920006346 thermoplastic polyester elastomer Polymers 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 230000037303 wrinkles Effects 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/15—Heterocyclic compounds having oxygen in the ring
- C08K5/151—Heterocyclic compounds having oxygen in the ring having one oxygen atom in the ring
- C08K5/1535—Five-membered rings
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C45/00—Injection moulding, i.e. forcing the required volume of moulding material through a nozzle into a closed mould; Apparatus therefor
- B29C45/0001—Injection moulding, i.e. forcing the required volume of moulding material through a nozzle into a closed mould; Apparatus therefor characterised by the choice of material
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C45/00—Injection moulding, i.e. forcing the required volume of moulding material through a nozzle into a closed mould; Apparatus therefor
- B29C45/14—Injection moulding, i.e. forcing the required volume of moulding material through a nozzle into a closed mould; Apparatus therefor incorporating preformed parts or layers, e.g. injection moulding around inserts or for coating articles
- B29C45/14549—Coating rod-like, wire-like or belt-like articles
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C45/00—Injection moulding, i.e. forcing the required volume of moulding material through a nozzle into a closed mould; Apparatus therefor
- B29C45/14—Injection moulding, i.e. forcing the required volume of moulding material through a nozzle into a closed mould; Apparatus therefor incorporating preformed parts or layers, e.g. injection moulding around inserts or for coating articles
- B29C45/14639—Injection moulding, i.e. forcing the required volume of moulding material through a nozzle into a closed mould; Apparatus therefor incorporating preformed parts or layers, e.g. injection moulding around inserts or for coating articles for obtaining an insulating effect, e.g. for electrical components
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/06—Ethers; Acetals; Ketals; Ortho-esters
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B3/00—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties
- H01B3/18—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances
- H01B3/30—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B7/00—Insulated conductors or cables characterised by their form
- H01B7/02—Disposition of insulation
- H01B7/0275—Disposition of insulation comprising one or more extruded layers of insulation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29K—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR MOULDS, REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS
- B29K2067/00—Use of polyesters or derivatives thereof, as moulding material
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29K—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR MOULDS, REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS
- B29K2105/00—Condition, form or state of moulded material or of the material to be shaped
- B29K2105/0005—Condition, form or state of moulded material or of the material to be shaped containing compounding ingredients
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29K—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR MOULDS, REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS
- B29K2705/00—Use of metals, their alloys or their compounds, for preformed parts, e.g. for inserts
- B29K2705/08—Transition metals
- B29K2705/10—Copper
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29K—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR MOULDS, REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS
- B29K2995/00—Properties of moulding materials, reinforcements, fillers, preformed parts or moulds
- B29K2995/0037—Other properties
- B29K2995/0093—Other properties hydrophobic
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29L—INDEXING SCHEME ASSOCIATED WITH SUBCLASS B29C, RELATING TO PARTICULAR ARTICLES
- B29L2031/00—Other particular articles
- B29L2031/34—Electrical apparatus, e.g. sparking plugs or parts thereof
- B29L2031/3462—Cables
Definitions
- Hydrophobic cyclic sugar alcohols are employed as polymer resin additives to provide repellency surface effects to the finished solid articles.
- compositions are known to be useful as treating agents to provide surface effects to substrates.
- Surface effects include repellency to moisture, soil and stain resistance, and other effects which are particularly useful for hard or fibrous substrates such as fibers, fabrics, textiles, carpets, paper, leather, stone and tile, glass, metal, and other such substrates.
- Many such treating agents are partially fluorinated polymers or copolymers.
- Fluorinated polymer compositions having utility as fibrous substrate treating agents generally contain pendant perfluoroalkyl groups of three or more carbon atoms, which provide oil- and water-repellency when the compositions are applied to fibrous substrate surfaces.
- the perfluoroalkyl groups are generally attached by various connecting groups to polymerizable groups not containing fluorine.
- the resulting monomer is then generally copolymerized with other monomers which confer additional favorable properties to the substrates.
- Various specialized monomers may be incorporated to impart improved cross-linking, latex stability and substantivity. Since each ingredient may impart some potentially undesirable properties in addition to its desirable ones, the specific combination is directed to the desired use.
- These polymers are generally marketed as aqueous emulsions for easy application to the fibrous substrates.
- Jariwala et al. (U.S. Pat. No. 5,228,157) discloses fluorochemical compounds for use as treating agents or polymer melt additives for the purposes of providing oil-, water-, or stain repellency to shaped articles such as fibers.
- the present invention relates to a three-dimensional solid polymeric article having surface effects comprising a polymer composition and 0.1 to 20% by weight of a hydrophobic compound, based on the total weight of the solid polymeric article, where the hydrophobic compound is intermixed throughout the polymer composition and throughout three-dimensional solid polymeric article; where the hydrophobic compound is selected from a cyclic sugar alcohol which is substituted with at least two R 1 , —C(O)R 1 , —(CH 2 CH 2 O) n (CH(CH 3 )CH 2 O) m R 2 , —(CH 2 CH 2 O) n (CH(CH 3 )CH 2 O) m C(O)R 1 , or mixtures thereof; where the cyclic sugar alcohol is selected from a saccharide, reduced sugar, aminosaccharide, aldonic acid, or aldonic acid lactone; wherein each n is independently 0 to 20; each m is independently 0 to 20; m+n is greater than 0; each R
- the invention further relates to a method of imparting a surface effect to a polymeric article comprising contacting a flowable or liquid polymer composition with 0.1% by weight to 20% by weight of a hydrophobic compound, based on the total weight of the polymer composition, to form a treated polymer composition, and allowing or causing the polymer composition to solidify to form a treated polymeric article, where the treatment composition comprises a hydrophobic compound selected from a cyclic sugar alcohol which is substituted with at least two R 1 , —C(O)R 1 , —(CH 2 CH 2 O) n (CH(CH 3 )CH 2 O) m R 2 , —(CH 2 CH 2 O) n (CH(CH 3 )CH 2 O) m C(O)R 1 , or mixtures thereof; where the cyclic sugar alcohol is selected from a saccharide, reduced sugar, aminosaccharide, aldonic acid, or aldonic acid lactone; wherein each n is independently 0 to 20; each
- the present invention provides three-dimensional solid polymeric articles having improved water repellency, oil or stain repellency, and/or other hydrophobic surface effects.
- the treated articles provide enhanced performance and durability compared to traditional non-fluorinated commercially available treatment agents.
- the hydrophobic compound additives of the present invention can be derived from bio-sourced materials.
- the present invention relates to a three-dimensional solid polymeric article having surface effects comprising a polymer composition and 0.1 to 20% by weight of a hydrophobic compound, based on the total weight of the solid polymeric article, where the hydrophobic compound is intermixed throughout the polymer composition and throughout three-dimensional solid polymeric article; where the hydrophobic compound is selected from a cyclic sugar alcohol which is substituted with at least two R 1 , —C(O)R 1 , —(CH 2 CH 2 O) n (CH(CH 3 )CH 2 O) m R 2 , —(CH 2 CH 2 O) n (CH(CH 3 )CH 2 O) m C(O)R 1 , or mixtures thereof; where the cyclic sugar alcohol is selected from a saccharide, reduced sugar, aminosaccharide, aldonic acid, or aldonic acid lactone; wherein each n is independently 0 to 20; each m is independently 0 to 20; m+n is greater than 0; each R
- —(CH 2 CH 2 O)— represents oxyethylene groups (EO) and —(CH(CH 3 )CH 2 O)— represents oxypropylene groups (PO).
- EO oxyethylene groups
- PO oxypropylene groups
- These compounds can contain only EO groups, only PO groups, or mixtures thereof.
- PEG-PPG-PEG polyethylene glycol-polypropylene glycol-polyethylene glycol
- n+m is 1 to 20; in another embodiment, n+m is 1 to 15; and in a third embodiment, n+m is 1 to 12.
- the cyclic alcohol is selected from a saccharide, reduced sugar, aminosaccharide, aldonic acid, or aldonic acid lactone. Mixtures of these compounds may also be used.
- the hydrophobic compounds are substituted with at least two —R 1 ; —C(O)R 1 ; —(CH 2 CH 2 O) n (CH(CH 3 )CH 2 O) m R 2 ; —(CH 2 CH 2 O) n (CH(CH 3 )CH 2 O) m C(O)R 1 ; or mixtures thereof. Such a substitution lends hydrophobic character to the monomer, and to the polymer molecules.
- the hydrophobic compound is substituted with at least three —R 1 ; —C(O)R 1 ; —(CH 2 CH 2 O) n (CH(CH 3 )CH 2 O) m R 2 ; —(CH 2 CH 2 O) n (CH(CH 3 )CH 2 O) m C(O)R 1 ; or mixtures thereof.
- These substituted compounds can be made by the reaction of a sugar alcohol with at least one fatty acid or alkoxylated fatty acid, such as by esterification of a fatty acid.
- sugar alcohols include but are not limited to aldoses and ketoses such as those compounds derived from tetroses, pentoses, hexoses, and heptoses.
- Suitable fatty acids include, but are not limited to, caprylic acid, capric acid, lauric acid, mysteric acid, palmitic acid, stearic acid, arachidic acid, behenic acid, lignoceric acid, alkoxylated versions of these acids, and mixtures thereof.
- R 1 is a linear or branched alkyl group having 11 to 29 carbons, and in another embodiment, R 1 is a linear or branched alkyl group having 17 to 21 carbons.
- R 2 is a linear or branched alkyl group having 12 to 30 carbons, in another embodiment, R 2 is a linear or branched alkyl group having 18 to 30 carbons, and in another embodiment, R 2 is a linear or branched alkyl group having 18 to 22 carbons.
- the fatty acid or long-chain alcohol substitution of the cyclic sugar alcohols has a melting point of at least ⁇ 59° C. In another embodiment, it has a melting point of at least 0° C., and in a third embodiment, it has a melting point of at least 40° C.
- hydrophobic compound is selected from Formula (Ia):
- each R is independently H; —R 1 ; —C(O)R 1 ; —(CH 2 CH 2 O) n (CH(CH 3 )CH 2 O) m R 2 ; or —(CH 2 CH 2 O) n (CH(CH 3 )CH 2 O) m C(O)R 1 ; each n is independently 0 to 20; each m is independently 0 to 20; m+n is greater than 0; r is 1 to 3; a is 0 or 1; p is independently 0 to 2; provided that a is 0 when r is 3; each R 1 is independently a linear or branched alkyl group having 5 to 29 carbons; and each R 2 is independently H, or a linear or branched alkyl group having 6 to 30 carbons; provided at least one R is H and at least two R groups are a —R 1 ; —C(O)R 1 ; —(CH 2 CH 2 O) n (CH(CH 3 )CH 2 O
- hydrophobic compound is Formula (Ia)
- any suitable substituted reduced sugar alcohol may be employed, including esters of 1,4-sorbitan, esters of 2,5-sorbitan, and esters of 3,6-sorbitan.
- the hydrophobic compound is selected from Formula (a) to be Formula (Ia′):
- R is further limited to H; —R 1 ; or —C(O)R 1 and at least two R groups are C(O)R 1 or R 1 .
- Compounds used to form residues of Formula (Ia′), having at least one of R is H and at least one R is selected from —C(O)R 1 are commonly known as alkyl sorbitans. These sorbitans can be di-substituted or tri-substituted with —C(O)R 1 .
- sorbitans such as SPAN
- sorbitans contain a mixture of the various sorbitans ranging from where each R is H (un-substituted), and sorbitans where each R is —C(O)R 1 (fully substituted); wherein R 1 is a linear or branched alkyl group having 5 to 29 carbons; and mixtures of various substitutions thereof.
- the commercially available sorbitans may also include amounts of sorbitol, isosorbide, or other intermediates or byproducts.
- R 1 is C(O)R 1
- R 1 is a linear branched alkyl group having 5 to 29 carbons.
- R 1 is a linear or branched alkyl group having 7 to 21 carbons
- R 1 is a linear or branched alkyl group having 11 to 21 carbons.
- Preferred compounds used to form these residues include di- and tri-substituted sorbitans derived from caprylic acid, capric acid, lauric acid, mysteric acid, palmitic acid, stearic acid, arachidic acid, behenic acid, lignoceric acid, and mixtures thereof.
- Particularly preferred compounds include di- and tri-substituted sorbitan stearates or sorbitan behenins.
- a compound of Formula (Ia) is employed, wherein at least two R groups are independently —(CH 2 CH 2 O) n (CH(CH 3 )CH 2 O) m R 2 or —(CH 2 CH 2 O) n (CH(CH 3 )CH 2 O) m C(O)R 1 .
- polysorbates contain a mixture of the various polysorbates ranging from where each R 2 is H (unsubstituted), and polysorbates where each R 1 is a linear or branched alkyl group having 5 to 29 carbons (fully substituted); and mixtures of various substitutions thereof.
- examples of compounds of Formula (Ia) include polysorbates such as polysorbate tristearate and polysorbate monostearate.
- Reagents may include mixtures of compounds having various values for R, R 1 , and R 2 , and may also include mixtures of compounds where R 1 comprises at least one unsaturated bond with compounds where R 1 is fully saturated.
- Compounds of Formula (Ia) can all be bio-based derived.
- bio-based derived it is meant that at least 10% of the material can be produced from non-crude oil sources, such as plants, other vegetation, and tallow.
- the hydrophobic compound is from about 10% to 100% bio-based derived.
- hydrophobic compound is from about 35% to 100% bio-based derived.
- hydrophobic compound is from about 50% to 100% bio-based derived.
- hydrophobic compound is from about 75% to 100% bio-based derived.
- hydrophobic compound is 100% bio-based derived.
- the average OH value of the hydrophobic compounds can range from just greater than 0 to about 230. In one embodiment, the average OH value is from about 10 to about 175, and in another embodiment, the average OH value is from about 25 to about 140.
- the three-dimensional solid polymeric article comprises 0.1 to 20% by weight of the hydrophobic compound, based on the total weight of the solid polymeric article.
- the article comprises 1 to 10% by weight of the hydrophobic compound; and in a third aspect, 1 to 5% by weight of the hydrophobic compound based on the total solids weight of the solid polymeric article.
- the polymer composition used to form the three-dimensional solid polymeric article may further comprise aqueous or organic solvents, additional polymer resins, pigments, functional additives, surfactants, and hydrophobic surface effect agents.
- the polymer composition used to form the body of the polymeric article may be any polymer resin which forms a solid material at room temperature, including but not limited to thermoplastic resins, thermoset resins, elastomeric resins, or amorphous polymers.
- Such polymer resins are synthetic. These include polyamide, polyester, polyepoxide, polystyrene, styrene copolymer, polyolefin, polyolefin copolymer, thermoplastic urethane, fluoroelastomers, polyfluoroolefins, acrylic polymers and copolymers, silicone, polyesters, and polycarbonate.
- the thermoplastic resins may be melted and shaped as desired.
- polyamides include linear polyamide such as nylons (nylon-6 or nylon-66), polystyrene and polystyrene copolymers including ABS polymers, polyethylene and polyethylene copolymers, polypropylene and polypropylene copolymers, thermoplastic urethanes, poly(acrylic acid), poly(methyl methacrylate), poly(methyl acrylate), polymethacrylate, polyacrylate, polyesters including thermoplastic polyesters, polyethylene terephthalate, polypropylene terephthalate, and polybutylene terephalate, polyvinyl chloride, polycaprolactones, polylactic acid, and copolymers of any of the preceding polymers.
- linear polyamide such as nylons (nylon-6 or nylon-66), polystyrene and polystyrene copolymers including ABS polymers, polyethylene and polyethylene copolymers, polypropylene and polypropylene copolymers, thermoplastic urethanes, poly(acrylic acid), poly(
- thermoplastic includes thermoplastic elastomers as well.
- the polymer composition may be present in the three-dimensional solid polymeric article in an amount of 60 to 99.9% by weight; in a second aspect, 60 to 99% by weight; and in a third aspect, 75 to 99% by weight, based on the total weight of the solid polymeric article.
- the balance of the three-dimensional article composition comprises additives including but not limited to pigments, viscosity modifiers, dyes, and other functional additives.
- the polymer composition contains no liquid carrier, including water or solvent. In another aspect, the polymer composition contains no more than 5% of a liquid carrier.
- the three-dimensional solid polymeric article further comprises a hydrophobic surface effect agent to provide further surface effects to the solid polymeric article.
- three-dimensional solid polymeric article comprises 0.1 to 20% by weight of the hydrophobic surface effect agent, based on the total weight of the solid polymeric article.
- the article comprises 1 to 10% by weight of the hydrophobic surface effect agent; and in a third aspect, 1 to 5% by weight of the hydrophobic surface effect agent based on the total solids weight of the solid polymeric article.
- Hydrophobic surface effect agents provide surface effects such as shrinkage control, wrinkle free, permanent press, moisture control, softness, strength, anti-slip, anti-static, anti-snag, anti-pill, stain repellency, stain release, soil repellency, soil release, water repellency, oil repellency, odor control, antimicrobial, sun protection, and similar effects.
- such materials can be in the form of non-fluorinated or fluorinated cationic acrylic polymers, non-fluorinated or fluorinated anionic acrylic polymers, non-fluorinated or fluorinated nonionic acrylic polymers, partially fluorinated urethanes, fluorinated ethoxylates, fluorinated alcohols, fluorinated phosphate acids, non-fluorinated urethanes, silicones, waxes, or mixtures thereof.
- fluorinated polymers to provide repellency properties to the surface of treated articles.
- fluorochemical compounds or polymers containing one or more fluoroaliphatic groups designated here as R f groups
- R f groups fluoroaliphatic groups
- the R f groups contain at least 3 carbon atoms, preferably 3 to 20 carbon atoms, more preferably 4 to 12 carbon atoms, and most preferably about 4 to about 6 carbon atoms.
- the R f groups may contain straight or branched chain or cyclic fluorinated alkylene groups or combinations thereof.
- the terminal portion of the R f groups is preferably a perfluorinated aliphatic group of the formula C n F 2n+1 wherein n is from about 3 to about 20.
- fluorinated polymer treating agents are CAPSTONE and ZONYL available from The Chemours Company, Wilmington, Del.; ASAHI GARD from Asahi Glass Company, Ltd., Tokyo, Japan; UNIDYNE from Daikin America, Inc., Orangeburg, N.Y.; SCOTCHGARD from 3M Company, St. Paul, Minn.; and NANO TEX from Nanotex, Emeryville, Calif.
- fluorinated polymers examples include R f -containing polyurethanes and poly(meth)acrylates.
- copolymers of fluorochemical (meth)acrylate monomers with a co-polymerizable monovinyl compound or a conjugated diene include alkyl (meth)acrylates, vinyl esters of aliphatic acids, styrene and alkyl styrene, vinyl halides, vinylidene halides, alkyl esters, vinyl alkyl ketones, and acrylamides.
- the conjugated dienes are preferably 1,3-butadienes.
- Representative compounds within the preceding classes include the methyl, propyl, butyl, 2-hydroxypropyl, 2-hydroxyethyl, isoamyl, 2-ethylhexyl, octyl, decyl, lauryl, cetyl, and octadecyl acrylates and methacrylates; vinyl acetate, vinyl propionate, vinyl caprylate, vinyl laurate, vinyl stearate, styrene, alpha methyl styrene, p-methylstyene, vinyl fluoride, vinyl chloride, vinyl bromide, vinylidene fluoride, vinylidene chloride, allyl heptanoate, allyl acetate, allyl caprylate, allyl caproate, vinyl methyl ketone, vinyl ethyl ketone, 1,3-butadiene, 2-chloro-1,3-butadiene, 2,3-dichloro-1,3-butad
- Hydrophobic non-fluorinated acrylic polymers include copolymers of monovinyl compounds, including alkyl (meth)acrylates, vinyl esters of aliphatic acids, styrene and alkyl styrene, vinyl halides, vinylidene halides, alkyl esters, vinyl alkyl ketones, and acrylamides.
- the conjugated dienes are preferably 1,3-butadienes.
- Representative compounds within the preceding classes include the methyl, propyl, butyl, 2-hydroxypropyl, 2-hydroxyethyl, isoamyl, 2-ethylhexyl, octyl, decyl, lauryl, cetyl, and octadecyl acrylates and methacrylates; vinyl acetate, vinyl propionate, vinyl caprylate, vinyl laurate, vinyl stearate, styrene, alpha methyl styrene, p-methylstyene, vinyl fluoride, vinyl chloride, vinyl bromide, vinylidene chloride, allyl heptanoate, allyl acetate, allyl caprylate, allyl caproate, vinyl methyl ketone, vinyl ethyl ketone, 1,3-butadiene, 2-chloro-1,3-butadiene, 2,3-dichloro-1,3-butadiene, isoprene,
- Hydrophobic non-fluorinated urethanes include, for example, urethanes synthesized by reacting an isocyanate compound with the hydrophobic compounds described above as an alcohol reagent. These compounds are described in US2014/0295724 and US2016/0090508.
- Hydrophobic non-fluorinated nonionic acrylic polymers include, for example, polymers made by polymerizing or copolymerizing an acrylic ester of the hydrophobic compounds described above. Such compounds are described in US2016/0090686.
- the hydrophobic surface effect agent can be a fluorinated alcohol which may be used to improve stain release properties of the end product. Any suitable fluorinated alcohol may be used. In one embodiment, the fluorinated alcohol has the formula
- R f is a C1 to C20 linear or branched perfluoroalkyl optionally interrupted by one, two or three ether oxygen atoms; x is 0 or 1; A is (CH 2 ) k , (CH 2 CF 2 ) m (CH 2 ) n , (CH 2 ) o SO 2 N(CH 3 )(CH 2 ) p , O(CF 2 ) 2 (CH 2 ) r , or OCHFCF 2 OE; Z is O, S, or NH; m is 1 to 4; k, n, o, p, and r are each independently 1 to 20; and E is a C2 to C20 linear or branched alkyl group optionally interrupted by oxygen, sulfur, or nitrogen atoms; a cyclic alkyl group, or a C6 to C10 aryl group.
- the fluorinated alcohol has Formula (II) where Z is O and where R f is a C1 to C20 perfluoroalkyl group optionally interrupted by CH 2 , CH 2 CH 2 , SO 2 N, CFH, S, or O; and A is a direct bond or a C 1 to C 6 alkylene group.
- R f and A may be linear or branched.
- the fluorinated alcohol is a telomer-based alcohol, where R f is a linear perfluoroalkyl group and A is CH 2 CH 2 .
- R f is a C 2 to C 6 linear or branched perfluoroalkyl group.
- fluorinated alcohols include but are not limited to R f OH, R f CH 2 CH 2 OH, R f SO 2 NHCH 2 CH 2 OH, R f CH 2 CH 2 SCH 2 CH 2 OH, R f CH 2 CH 2 CF 2 CF 2 CH 2 CH 2 OH, R f CH 2 CH 2 (CF 2 CF 2 CH 2 CH 2 ) 2 OH, R f CH 2 CF 2 CH 2 CH 2 OH, R f CH 2 CF 2 CH 2 CF 2 CH 2 CH 2 OH, R f OCF 2 CF 2 CH 2 CH 2 OH, R f CH 2 OCH 2 CH 2 OH, R f CHFCH 2 CH 2 OH, R f CH 2 O(CH 2 ) 6 OH, (CF 3 ) 2 CFCH 2 CH 2 OH, (CF 3 ) 2 CFCH 2 CH 2 CH 2 OH, R f CH 2 SO 2 NHCH 2 CH 2 OH, R f CH 2 CH 2 SO 2 N(
- the three-dimensional solid polymer articles of the present invention optionally further comprise additional components such as surfactants, pH adjusters, cross linkers, wetting agents, pigments, and other functional additives known by those skilled in the art.
- the invention further relates to a method of imparting a surface effect to a polymeric article comprising contacting a flowable or liquid polymer composition with 0.1% by weight to 20% by weight of a hydrophobic compound, based on the total weight of the polymer composition, to form a treated polymer composition, and allowing or causing the polymer composition to solidify to form a treated polymeric article, where the treatment composition comprises a hydrophobic compound selected from a cyclic sugar alcohol which is substituted with at least two R 1 , —C(O)R 1 , —(CH 2 CH 2 O) n (CH(CH 3 )CH 2 O) m R 2 , —(CH 2 CH 2 O) n (CH(CH 3 )CH 2 O) m C(O)R 1 , or mixtures thereof; where the cyclic sugar alcohol is selected from a saccharide, reduced sugar, aminosaccharide, aldonic acid, or aldonic acid lactone; wherein each n is independently 0 to 20; each
- the contacting step may occur by any conventional method, including standard mixing, with a molten polymer composition, with a flowable polymer composition, with a polymer composition dispersion, or with a polymer composition solution.
- the polymer composition having the hydrophobic compound intermixed may be solidified by any conventional method, including by drying, by cooling, or by causing to cool. Drying may be completed with or without heating. Solidification may occur before or after the formation and shaping of the three-dimensional article.
- the three-dimensional article is formed by any conventional method, including molding, extruding, or spinning a liquid polymer composition having the hydrophobic compound intermixed therein; by thermoforming sheets of the polymeric composition having the hydrophobic compound intermixed therein.
- thermoplastic polymer resin may be mixed with the hydrophobic compound while molten, may be extruded and shaped into, for example, fibers, and may be cooled to form the three-dimensional article.
- the solid three-dimensional polymeric articles are useful in applications including, but not limited to, moisture and grease-resistant packaging, release liners, multilayer constructions, oil- and water-repellent carpet fibers, oil- and water-repellent textile fibers, repellent medical non-woven fabrics, and repellent caulks and other filling sealers.
- Sorbitan tristearate is available from DuPont Nutrition & Health, Copenhagen, Denmark.
- HYTREL 3078 is a thermoplastic polyester elastomer copolymer commercially available from DuPont, Wilmington, Del.
- Water contact angle measurements are used to test for the migration of additive to the surface of the compression molded sheet samples. Testing is performed by a Ramo-Hart Standard Automated Goniometer Model 200 employing DROPimage standard software and equipped with an automated dispensing system, 250 ⁇ l syringe, and illuminated specimen stage assembly is used.
- the goniometer camera is connected through an interface to a computer, allowing the droplet to be visualized on a computer screen.
- the horizontal axis line and the cross line can both be independently adjusted on the computer screen using the software.
- the sample Prior to contact angle measurement, the sample is placed on the sample stage and the vertical vernier is adjusted to align the horizontal line (axis) of the eye piece coincident to the horizontal plane of the sample.
- the horizontal position of the stage relative to the eye piece is positioned so as to view one side of the test fluid droplet interface region at the sample interface.
- test fluid approximately one drop of test fluid is dispensed onto the sample using a 30 ⁇ L pipette tip and an automated dispensing system to displace a calibrated amount of the test fluid.
- Deionized water is used for water contact angle measurements.
- Horizontal and cross lines are adjusted via the software in case of the Model 200 after leveling the sample via stage adjustment, and the computer calculates the contact angle based upon modeling the drop appearance.
- the initial contact angle is the angle determined immediately after dispensing the test fluid to the sample surface. Initial contact angles above 30 degrees are indicators of effective oil repellency.
- the friction coefficient was measured according to ASTM D1894 “Standard Test Method for Static and Kinetic Coefficients of Friction of Plastic Film and Sheeting”.
- the sample is cut to a size of 250 mm ⁇ 130 mm and secured on the test plane.
- a second test piece is cut to 120 mm square if the specimen is defined as a film, and 63.5 mm square if defined as sheeting, and attached to the sled. Care is taken not to contaminate the test pieces by handling or foreign matter and condition according to ASTM D618.
- the sled is attached to the friction tester crosshead, and the driving mechanism is set to a speed of 150 ⁇ 30 mm/min (6.0 ⁇ 1.2 in./min).
- the initial maximum force reading is recorded, which is the static frictional force.
- the sliding is continued for another 130 mm.
- An average force reading is obtained for the kinetic friction. Five data sets are taken on separate samples.
- stains used to evaluate easy clean performance on untreated and treated shims, including grape juice, ketchup, corn oil, mustard, cola, coffee, and ink.
- the stains were applied in the same layout for each substrate, using a disposable pipette.
- the volume of the stains applied with a pipette was about 50 ⁇ L in order to keep the stain quantity and drop size consistent.
- the stains were left to dwell for about 15 hours.
- the liquid stains were vacuumed one at a time, wiping the end of the tubing to avoid contaminating different stains.
- the substrate was placed under a running faucet with warm water to remove some of the stains, and the substrate was wiped and dried with a SONTARA wipe.
- the samples were placed on the lab bench face up to dry for 4 hours.
- % ECF Percent Easy Clean Factor
- Pellets of HYTREL 3078 were dried at 130° F. and blended with sorbitan tristearate, which was in the form of a dry powder, to yield a blend of 2.5% by weight sorbitan tristearate (Example 1) and 5% by weight sorbitan tristearate (Example 2).
- the powder/pellet blends were fed to a Davis Standard 1.5′′ extruder operating at 25 rpm.
- the extruder had a length/diameter ratio of 24:1 and was equipped with a screw fitted with a Saxton mixer located at the end of the metering section in order to provide uniform temperature and dispersion of the additives within the melt.
- the compression ratio of the screw depth of the feed section to the depth of the metering section was approximately 3.2 to 1.
- the temperature profile for the extruder was kept at or below 410° F. (210° C.) to minimize any potential thermal degradation.
- Extrudate was processed on a wire-line to produce an insulation ⁇ 25 mil ( ⁇ 0.64 mm) in thickness on a 7 stranded 18 AWG bare copper conductor have a diameter of ⁇ 48 mils ( ⁇ 1.2 mm).
- the material was extruded onto wire at a speeds of ⁇ 60 to 65 ft/min via a tubing configuration consisting of a die have an inner diameter of 180 mils (4.6 mm) and a guider tip outer diameter of 90 mils (2.3 mm).
- the die and guider tip combinations yielded draw down ratios (cross-sectional area of the die area/cross-sectional area of the finished extrudate) of ⁇ 3.5.
- extrudate was collected to be utilized in post extrusion molding operations to create small flat sheets for testing.
- the resulting extrudates were dried overnight at 130° F. where they were compression molded into sheets approximately 6 inches ( ⁇ 152 mm) square with a thickness of ⁇ 30 mils ( ⁇ 0.76 mm).
- Approximately 16.5 to 17 grams of material was placed between two sheets of polytetrafluoroethylene (PTFE) within a picture frame shim used to achieve the desired dimensions.
- the stack consisting of the PTFE sheeting, shim, and material was placed between 2 metal plates and then transferred to a hot press with platens set to a temperature of 392° F. (200° C.).
- the pressure within the press was raised and maintained at ⁇ 5 lbs for a time period of 8 minutes. After this time period allowing the material to soften, the pressure was raised to 10 tons and released multiple times within a one minute period and then maintained at 10 tons for an additional minute allowing the material to flow and acquire the desired dimensions. The pressure was then released and the stack transferred to a water cooled press where the material was held for approximately 5 minutes under low pressure until the sample cooled for removal from the shims. The sheets were tested according to the test methods above.
- Example 1 was repeated, without the addition of sorbitan tristearate.
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Mechanical Engineering (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Materials Applied To Surfaces To Minimize Adherence Of Mist Or Water (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Description
- Hydrophobic cyclic sugar alcohols are employed as polymer resin additives to provide repellency surface effects to the finished solid articles.
- Various compositions are known to be useful as treating agents to provide surface effects to substrates. Surface effects include repellency to moisture, soil and stain resistance, and other effects which are particularly useful for hard or fibrous substrates such as fibers, fabrics, textiles, carpets, paper, leather, stone and tile, glass, metal, and other such substrates. Many such treating agents are partially fluorinated polymers or copolymers.
- Fluorinated polymer compositions having utility as fibrous substrate treating agents generally contain pendant perfluoroalkyl groups of three or more carbon atoms, which provide oil- and water-repellency when the compositions are applied to fibrous substrate surfaces. The perfluoroalkyl groups are generally attached by various connecting groups to polymerizable groups not containing fluorine. The resulting monomer is then generally copolymerized with other monomers which confer additional favorable properties to the substrates. Various specialized monomers may be incorporated to impart improved cross-linking, latex stability and substantivity. Since each ingredient may impart some potentially undesirable properties in addition to its desirable ones, the specific combination is directed to the desired use. These polymers are generally marketed as aqueous emulsions for easy application to the fibrous substrates.
- Various attempts have been made to increase the oil- and water-repellency imparted an article while reducing the amount of fluorinated polymer required, i.e., boost the efficiency or performance of the treating agent. One method is to incorporate blocked isocyanates or melamine resins. However, only limited amounts can be used because these ingredients tend to adversely affect the handle (the feel) of the fibrous substrate. Another approach employs use of various extender polymers. These are typically hydrocarbon polymers in aqueous emulsions, which are blended with the fluorinated polymer emulsion before application to the substrate.
- Jariwala et al. (U.S. Pat. No. 5,228,157) discloses fluorochemical compounds for use as treating agents or polymer melt additives for the purposes of providing oil-, water-, or stain repellency to shaped articles such as fibers.
- There is a need for surface effect compositions which provide hydrophobicity performance with improved fluorine efficiency in polymeric resin articles. The present invention provides such a composition.
- The present invention relates to a three-dimensional solid polymeric article having surface effects comprising a polymer composition and 0.1 to 20% by weight of a hydrophobic compound, based on the total weight of the solid polymeric article, where the hydrophobic compound is intermixed throughout the polymer composition and throughout three-dimensional solid polymeric article; where the hydrophobic compound is selected from a cyclic sugar alcohol which is substituted with at least two R1, —C(O)R1, —(CH2CH2O)n(CH(CH3)CH2O)mR2, —(CH2CH2O)n(CH(CH3)CH2O)mC(O)R1, or mixtures thereof; where the cyclic sugar alcohol is selected from a saccharide, reduced sugar, aminosaccharide, aldonic acid, or aldonic acid lactone; wherein each n is independently 0 to 20; each m is independently 0 to 20; m+n is greater than 0; each R1 is independently a linear or branched alkyl group having 5 to 29 carbons; and each R2 is independently H, a linear or branched alkyl group having 6 to 30 carbons.
- The invention further relates to a method of imparting a surface effect to a polymeric article comprising contacting a flowable or liquid polymer composition with 0.1% by weight to 20% by weight of a hydrophobic compound, based on the total weight of the polymer composition, to form a treated polymer composition, and allowing or causing the polymer composition to solidify to form a treated polymeric article, where the treatment composition comprises a hydrophobic compound selected from a cyclic sugar alcohol which is substituted with at least two R1, —C(O)R1, —(CH2CH2O)n(CH(CH3)CH2O)mR2, —(CH2CH2O)n(CH(CH3)CH2O)mC(O)R1, or mixtures thereof; where the cyclic sugar alcohol is selected from a saccharide, reduced sugar, aminosaccharide, aldonic acid, or aldonic acid lactone; wherein each n is independently 0 to 20; each m is independently 0 to 20; m+n is greater than 0; each R1 is independently a linear or branched alkyl group having 5 to 29 carbons; each R2 is independently H, a linear or branched alkyl group having 6 to 30 carbons.
- Trademarks are indicated herein by capitalization.
- The present invention provides three-dimensional solid polymeric articles having improved water repellency, oil or stain repellency, and/or other hydrophobic surface effects. The treated articles provide enhanced performance and durability compared to traditional non-fluorinated commercially available treatment agents. Furthermore, the hydrophobic compound additives of the present invention can be derived from bio-sourced materials.
- The present invention relates to a three-dimensional solid polymeric article having surface effects comprising a polymer composition and 0.1 to 20% by weight of a hydrophobic compound, based on the total weight of the solid polymeric article, where the hydrophobic compound is intermixed throughout the polymer composition and throughout three-dimensional solid polymeric article; where the hydrophobic compound is selected from a cyclic sugar alcohol which is substituted with at least two R1, —C(O)R1, —(CH2CH2O)n(CH(CH3)CH2O)mR2, —(CH2CH2O)n(CH(CH3)CH2O)mC(O)R1, or mixtures thereof; where the cyclic sugar alcohol is selected from a saccharide, reduced sugar, aminosaccharide, aldonic acid, or aldonic acid lactone; wherein each n is independently 0 to 20; each m is independently 0 to 20; m+n is greater than 0; each R1 is independently a linear or branched alkyl group having 5 to 29 carbons; and each R2 is independently H, a linear or branched alkyl group having 6 to 30 carbons. The —(CH2CH2O)— represents oxyethylene groups (EO) and —(CH(CH3)CH2O)— represents oxypropylene groups (PO). These compounds can contain only EO groups, only PO groups, or mixtures thereof. These compounds can also be present as a tri-block copolymer designated PEG-PPG-PEG (polyethylene glycol-polypropylene glycol-polyethylene glycol), for example. In one embodiment, n+m is 1 to 20; in another embodiment, n+m is 1 to 15; and in a third embodiment, n+m is 1 to 12.
- The cyclic alcohol is selected from a saccharide, reduced sugar, aminosaccharide, aldonic acid, or aldonic acid lactone. Mixtures of these compounds may also be used. The hydrophobic compounds are substituted with at least two —R1; —C(O)R1; —(CH2CH2O)n(CH(CH3)CH2O)mR2; —(CH2CH2O)n(CH(CH3)CH2O)mC(O)R1; or mixtures thereof. Such a substitution lends hydrophobic character to the monomer, and to the polymer molecules. In one embodiment, the hydrophobic compound is substituted with at least three —R1; —C(O)R1; —(CH2CH2O)n(CH(CH3)CH2O)mR2; —(CH2CH2O)n(CH(CH3)CH2O)mC(O)R1; or mixtures thereof.
- These substituted compounds can be made by the reaction of a sugar alcohol with at least one fatty acid or alkoxylated fatty acid, such as by esterification of a fatty acid. Examples of such sugar alcohols include but are not limited to aldoses and ketoses such as those compounds derived from tetroses, pentoses, hexoses, and heptoses. Specific examples include glucose, allose, altrose, mannose, xylose, lyxose, galactose, talose, fructose, 1,4-anhydro-D-glucitol, 2,5-anhydro-D-mannitol, 2,5-anhydro-L-iditol, sorbitan, mannoheptulose, glucopyranose, mannopyranose, talopyranose, allopyranose, altropyranose, idopyranose, gulopyranose, inositol, ascorbic acid, gluconic acid lactone, glyceric acid lactone, xylonic acid lactone, isosorbide, glucosamine, galactosamine, or mixtures thereof.
- Suitable fatty acids include, but are not limited to, caprylic acid, capric acid, lauric acid, mysteric acid, palmitic acid, stearic acid, arachidic acid, behenic acid, lignoceric acid, alkoxylated versions of these acids, and mixtures thereof.
- In one embodiment, R1 is a linear or branched alkyl group having 11 to 29 carbons, and in another embodiment, R1 is a linear or branched alkyl group having 17 to 21 carbons. In one embodiment, R2 is a linear or branched alkyl group having 12 to 30 carbons, in another embodiment, R2 is a linear or branched alkyl group having 18 to 30 carbons, and in another embodiment, R2 is a linear or branched alkyl group having 18 to 22 carbons. In one embodiment, the fatty acid or long-chain alcohol substitution of the cyclic sugar alcohols has a melting point of at least −59° C. In another embodiment, it has a melting point of at least 0° C., and in a third embodiment, it has a melting point of at least 40° C.
- In one embodiment, the hydrophobic compound is selected from Formula (Ia):
- wherein each R is independently H; —R1; —C(O)R1; —(CH2CH2O)n(CH(CH3)CH2O)mR2; or —(CH2CH2O)n(CH(CH3)CH2O)mC(O)R1; each n is independently 0 to 20; each m is independently 0 to 20; m+n is greater than 0; r is 1 to 3; a is 0 or 1; p is independently 0 to 2; provided that a is 0 when r is 3; each R1 is independently a linear or branched alkyl group having 5 to 29 carbons; and each R2 is independently H, or a linear or branched alkyl group having 6 to 30 carbons; provided at least one R is H and at least two R groups are a —R1; —C(O)R1; —(CH2CH2O)n(CH(CH3)CH2O)mR2; or
- (CH2CH2O)n(CH(CH3)CH2O)mC(O)R1.
- Where the hydrophobic compound is Formula (Ia), any suitable substituted reduced sugar alcohol may be employed, including esters of 1,4-sorbitan, esters of 2,5-sorbitan, and esters of 3,6-sorbitan. In one embodiment, the hydrophobic compound is selected from Formula (a) to be Formula (Ia′):
- wherein R is further limited to H; —R1; or —C(O)R1 and at least two R groups are C(O)R1 or R1. Compounds used to form residues of Formula (Ia′), having at least one of R is H and at least one R is selected from —C(O)R1, are commonly known as alkyl sorbitans. These sorbitans can be di-substituted or tri-substituted with —C(O)R1. It is known that commercially available sorbitans, such as SPAN, contain a mixture of the various sorbitans ranging from where each R is H (un-substituted), and sorbitans where each R is —C(O)R1 (fully substituted); wherein R1 is a linear or branched alkyl group having 5 to 29 carbons; and mixtures of various substitutions thereof. The commercially available sorbitans may also include amounts of sorbitol, isosorbide, or other intermediates or byproducts.
- In one embodiment, at least two R groups are C(O)R1, and R1 is a linear branched alkyl group having 5 to 29 carbons. In another embodiment, R1 is a linear or branched alkyl group having 7 to 21 carbons, and in a third embodiment, R1 is a linear or branched alkyl group having 11 to 21 carbons. Preferred compounds used to form these residues include di- and tri-substituted sorbitans derived from caprylic acid, capric acid, lauric acid, mysteric acid, palmitic acid, stearic acid, arachidic acid, behenic acid, lignoceric acid, and mixtures thereof. Particularly preferred compounds include di- and tri-substituted sorbitan stearates or sorbitan behenins.
- In one embodiment, a compound of Formula (Ia) is employed, wherein at least two R groups are independently —(CH2CH2O)n(CH(CH3)CH2O)mR2 or —(CH2CH2O)n(CH(CH3)CH2O)mC(O)R1. Compounds of Formula (Ia), wherein at least two R groups are —(CH2CH2O)n(CH(CH3)CH2O)mR2 or —(CH2CH2O)n(CH(CH3)CH2O)mC(O)R1, wherein each m is independently 0 to 20, each n is independently 0 to 20, and n+m is greater than 0 are known as polysorbates and are commercially available under the tradename TWEEN. These polysorbates can be di-substituted or tri-substituted with alkyl groups R1 or R2. It is known that commercially available polysorbates contain a mixture of the various polysorbates ranging from where each R2 is H (unsubstituted), and polysorbates where each R1 is a linear or branched alkyl group having 5 to 29 carbons (fully substituted); and mixtures of various substitutions thereof. Examples of compounds of Formula (Ia) include polysorbates such as polysorbate tristearate and polysorbate monostearate. Reagents may include mixtures of compounds having various values for R, R1, and R2, and may also include mixtures of compounds where R1 comprises at least one unsaturated bond with compounds where R1 is fully saturated.
- Compounds of Formula (Ia) can all be bio-based derived. By “bio-based derived”, it is meant that at least 10% of the material can be produced from non-crude oil sources, such as plants, other vegetation, and tallow. In one embodiment, the hydrophobic compound is from about 10% to 100% bio-based derived. In one embodiment, hydrophobic compound is from about 35% to 100% bio-based derived. In another embodiment, hydrophobic compound is from about 50% to 100% bio-based derived. In one embodiment, hydrophobic compound is from about 75% to 100% bio-based derived. In one embodiment, hydrophobic compound is 100% bio-based derived. The average OH value of the hydrophobic compounds can range from just greater than 0 to about 230. In one embodiment, the average OH value is from about 10 to about 175, and in another embodiment, the average OH value is from about 25 to about 140.
- The three-dimensional solid polymeric article comprises 0.1 to 20% by weight of the hydrophobic compound, based on the total weight of the solid polymeric article. In a second aspect, the article comprises 1 to 10% by weight of the hydrophobic compound; and in a third aspect, 1 to 5% by weight of the hydrophobic compound based on the total solids weight of the solid polymeric article. The polymer composition used to form the three-dimensional solid polymeric article may further comprise aqueous or organic solvents, additional polymer resins, pigments, functional additives, surfactants, and hydrophobic surface effect agents.
- The polymer composition used to form the body of the polymeric article may be any polymer resin which forms a solid material at room temperature, including but not limited to thermoplastic resins, thermoset resins, elastomeric resins, or amorphous polymers. Such polymer resins are synthetic. These include polyamide, polyester, polyepoxide, polystyrene, styrene copolymer, polyolefin, polyolefin copolymer, thermoplastic urethane, fluoroelastomers, polyfluoroolefins, acrylic polymers and copolymers, silicone, polyesters, and polycarbonate. The thermoplastic resins may be melted and shaped as desired. More specific polyamides include linear polyamide such as nylons (nylon-6 or nylon-66), polystyrene and polystyrene copolymers including ABS polymers, polyethylene and polyethylene copolymers, polypropylene and polypropylene copolymers, thermoplastic urethanes, poly(acrylic acid), poly(methyl methacrylate), poly(methyl acrylate), polymethacrylate, polyacrylate, polyesters including thermoplastic polyesters, polyethylene terephthalate, polypropylene terephthalate, and polybutylene terephalate, polyvinyl chloride, polycaprolactones, polylactic acid, and copolymers of any of the preceding polymers. The term “thermoplastic” includes thermoplastic elastomers as well. In one aspect, the polymer composition may be present in the three-dimensional solid polymeric article in an amount of 60 to 99.9% by weight; in a second aspect, 60 to 99% by weight; and in a third aspect, 75 to 99% by weight, based on the total weight of the solid polymeric article. The balance of the three-dimensional article composition comprises additives including but not limited to pigments, viscosity modifiers, dyes, and other functional additives. In one aspect, the polymer composition contains no liquid carrier, including water or solvent. In another aspect, the polymer composition contains no more than 5% of a liquid carrier.
- In one embodiment, the three-dimensional solid polymeric article further comprises a hydrophobic surface effect agent to provide further surface effects to the solid polymeric article. In this case, three-dimensional solid polymeric article comprises 0.1 to 20% by weight of the hydrophobic surface effect agent, based on the total weight of the solid polymeric article. In a second aspect, the article comprises 1 to 10% by weight of the hydrophobic surface effect agent; and in a third aspect, 1 to 5% by weight of the hydrophobic surface effect agent based on the total solids weight of the solid polymeric article. Hydrophobic surface effect agents provide surface effects such as shrinkage control, wrinkle free, permanent press, moisture control, softness, strength, anti-slip, anti-static, anti-snag, anti-pill, stain repellency, stain release, soil repellency, soil release, water repellency, oil repellency, odor control, antimicrobial, sun protection, and similar effects. In one aspect, such materials can be in the form of non-fluorinated or fluorinated cationic acrylic polymers, non-fluorinated or fluorinated anionic acrylic polymers, non-fluorinated or fluorinated nonionic acrylic polymers, partially fluorinated urethanes, fluorinated ethoxylates, fluorinated alcohols, fluorinated phosphate acids, non-fluorinated urethanes, silicones, waxes, or mixtures thereof.
- Superior properties, along with desirable properties of low yellowing and good durability, are imparted to articles by the combination of the hydrophobic compounds and hydrophobic surface effect agents within the solid polymeric articles. These combined blends may be, for example, contacted with the polymer composition in the form of a dispersion in water or other solvents.
- Of particular interest are fluorinated polymers to provide repellency properties to the surface of treated articles. These include fluorochemical compounds or polymers containing one or more fluoroaliphatic groups (designated here as Rf groups) which are fluorinated, stable, inert, and non-polar, preferably saturated, monovalent, and both oleophobic and hydrophobic. The Rf groups contain at least 3 carbon atoms, preferably 3 to 20 carbon atoms, more preferably 4 to 12 carbon atoms, and most preferably about 4 to about 6 carbon atoms. The Rf groups may contain straight or branched chain or cyclic fluorinated alkylene groups or combinations thereof. The terminal portion of the Rf groups is preferably a perfluorinated aliphatic group of the formula CnF2n+1 wherein n is from about 3 to about 20. Examples of fluorinated polymer treating agents are CAPSTONE and ZONYL available from The Chemours Company, Wilmington, Del.; ASAHI GARD from Asahi Glass Company, Ltd., Tokyo, Japan; UNIDYNE from Daikin America, Inc., Orangeburg, N.Y.; SCOTCHGARD from 3M Company, St. Paul, Minn.; and NANO TEX from Nanotex, Emeryville, Calif.
- Examples of such fluorinated polymers include Rf-containing polyurethanes and poly(meth)acrylates. Especially preferred are copolymers of fluorochemical (meth)acrylate monomers with a co-polymerizable monovinyl compound or a conjugated diene. The co-polymerizable monovinyl compounds include alkyl (meth)acrylates, vinyl esters of aliphatic acids, styrene and alkyl styrene, vinyl halides, vinylidene halides, alkyl esters, vinyl alkyl ketones, and acrylamides. The conjugated dienes are preferably 1,3-butadienes. Representative compounds within the preceding classes include the methyl, propyl, butyl, 2-hydroxypropyl, 2-hydroxyethyl, isoamyl, 2-ethylhexyl, octyl, decyl, lauryl, cetyl, and octadecyl acrylates and methacrylates; vinyl acetate, vinyl propionate, vinyl caprylate, vinyl laurate, vinyl stearate, styrene, alpha methyl styrene, p-methylstyene, vinyl fluoride, vinyl chloride, vinyl bromide, vinylidene fluoride, vinylidene chloride, allyl heptanoate, allyl acetate, allyl caprylate, allyl caproate, vinyl methyl ketone, vinyl ethyl ketone, 1,3-butadiene, 2-chloro-1,3-butadiene, 2,3-dichloro-1,3-butadiene, isoprene, N-methylolacrylamide, N-methylolmethacrylamide, glycidyl acrylate, glycidyl methacrylate, amine-terminated (meth)acrylates, and polyoxy(meth)acrylates.
- Hydrophobic non-fluorinated acrylic polymers include copolymers of monovinyl compounds, including alkyl (meth)acrylates, vinyl esters of aliphatic acids, styrene and alkyl styrene, vinyl halides, vinylidene halides, alkyl esters, vinyl alkyl ketones, and acrylamides. The conjugated dienes are preferably 1,3-butadienes. Representative compounds within the preceding classes include the methyl, propyl, butyl, 2-hydroxypropyl, 2-hydroxyethyl, isoamyl, 2-ethylhexyl, octyl, decyl, lauryl, cetyl, and octadecyl acrylates and methacrylates; vinyl acetate, vinyl propionate, vinyl caprylate, vinyl laurate, vinyl stearate, styrene, alpha methyl styrene, p-methylstyene, vinyl fluoride, vinyl chloride, vinyl bromide, vinylidene chloride, allyl heptanoate, allyl acetate, allyl caprylate, allyl caproate, vinyl methyl ketone, vinyl ethyl ketone, 1,3-butadiene, 2-chloro-1,3-butadiene, 2,3-dichloro-1,3-butadiene, isoprene, N-methylolacrylamide, N-methylolmethacrylamide, glycidyl acrylate, glycidyl methacrylate, amine-terminated (meth)acrylates, and polyoxy(meth)acrylates.
- Hydrophobic non-fluorinated urethanes include, for example, urethanes synthesized by reacting an isocyanate compound with the hydrophobic compounds described above as an alcohol reagent. These compounds are described in US2014/0295724 and US2016/0090508. Hydrophobic non-fluorinated nonionic acrylic polymers include, for example, polymers made by polymerizing or copolymerizing an acrylic ester of the hydrophobic compounds described above. Such compounds are described in US2016/0090686.
- In one embodiment the hydrophobic surface effect agent can be a fluorinated alcohol which may be used to improve stain release properties of the end product. Any suitable fluorinated alcohol may be used. In one embodiment, the fluorinated alcohol has the formula
-
Rf-Ax-Z—H (II) - wherein Rf is a C1 to C20 linear or branched perfluoroalkyl optionally interrupted by one, two or three ether oxygen atoms; x is 0 or 1; A is (CH2)k, (CH2CF2)m(CH2)n, (CH2)oSO2N(CH3)(CH2)p, O(CF2)2(CH2)r, or OCHFCF2OE; Z is O, S, or NH; m is 1 to 4; k, n, o, p, and r are each independently 1 to 20; and E is a C2 to C20 linear or branched alkyl group optionally interrupted by oxygen, sulfur, or nitrogen atoms; a cyclic alkyl group, or a C6 to C10 aryl group. In one embodiment, the fluorinated alcohol has Formula (II) where Z is O and where Rf is a C1 to C20 perfluoroalkyl group optionally interrupted by CH2, CH2CH2, SO2N, CFH, S, or O; and A is a direct bond or a C1 to C6 alkylene group. Rf and A may be linear or branched. In one aspect, the fluorinated alcohol is a telomer-based alcohol, where Rf is a linear perfluoroalkyl group and A is CH2CH2. In one aspect, Rf is a C2 to C6 linear or branched perfluoroalkyl group. Specific examples of fluorinated alcohols include but are not limited to RfOH, RfCH2CH2OH, RfSO2NHCH2CH2OH, RfCH2CH2SCH2CH2OH, RfCH2CH2CF2CF2CH2CH2OH, RfCH2CH2(CF2CF2CH2CH2)2OH, RfCH2CF2CH2CH2OH, RfCH2CF2CH2CF2CH2CH2OH, RfOCF2CF2CH2CH2OH, RfCH2OCH2CH2OH, RfCHFCH2CH2OH, RfCH2O(CH2)6OH, (CF3)2CFCH2CH2OH, (CF3)2CFCH2CH2 CH2OH, RfCH2CH2SO2NHCH2CH2OH, RfCH2CH2SO2N(CH3)CH2CH2OH, RfCH2CH2SO2N(CH2CH3)CH2CH2OH, R—(CF(CF3)CF2O)yCH2OH, CF2═CFOCF2CF(CF3)OCF2CF2CH2OH, or RfCH2OC2F4CH2OCH2CH2OH. Alkoylated compounds made from these alcohols are also useful as hydrophobic surface effect agents.
- The three-dimensional solid polymer articles of the present invention optionally further comprise additional components such as surfactants, pH adjusters, cross linkers, wetting agents, pigments, and other functional additives known by those skilled in the art.
- The invention further relates to a method of imparting a surface effect to a polymeric article comprising contacting a flowable or liquid polymer composition with 0.1% by weight to 20% by weight of a hydrophobic compound, based on the total weight of the polymer composition, to form a treated polymer composition, and allowing or causing the polymer composition to solidify to form a treated polymeric article, where the treatment composition comprises a hydrophobic compound selected from a cyclic sugar alcohol which is substituted with at least two R1, —C(O)R1, —(CH2CH2O)n(CH(CH3)CH2O)mR2, —(CH2CH2O)n(CH(CH3)CH2O)mC(O)R1, or mixtures thereof; where the cyclic sugar alcohol is selected from a saccharide, reduced sugar, aminosaccharide, aldonic acid, or aldonic acid lactone; wherein each n is independently 0 to 20; each m is independently 0 to 20; m+n is greater than 0; each R1 is independently a linear or branched alkyl group having 5 to 29 carbons; each R2 is independently H, a linear or branched alkyl group having 6 to 30 carbons.
- The contacting step may occur by any conventional method, including standard mixing, with a molten polymer composition, with a flowable polymer composition, with a polymer composition dispersion, or with a polymer composition solution. Following the contacting step, the polymer composition having the hydrophobic compound intermixed may be solidified by any conventional method, including by drying, by cooling, or by causing to cool. Drying may be completed with or without heating. Solidification may occur before or after the formation and shaping of the three-dimensional article. The three-dimensional article is formed by any conventional method, including molding, extruding, or spinning a liquid polymer composition having the hydrophobic compound intermixed therein; by thermoforming sheets of the polymeric composition having the hydrophobic compound intermixed therein. For example, a thermoplastic polymer resin may be mixed with the hydrophobic compound while molten, may be extruded and shaped into, for example, fibers, and may be cooled to form the three-dimensional article. The solid three-dimensional polymeric articles are useful in applications including, but not limited to, moisture and grease-resistant packaging, release liners, multilayer constructions, oil- and water-repellent carpet fibers, oil- and water-repellent textile fibers, repellent medical non-woven fabrics, and repellent caulks and other filling sealers.
- All solvents and reagents, unless otherwise indicated, were purchased from Sigma-Aldrich, St. Louis, Mo., and used directly as supplied.
- Sorbitan tristearate is available from DuPont Nutrition & Health, Copenhagen, Denmark.
- HYTREL 3078 is a thermoplastic polyester elastomer copolymer commercially available from DuPont, Wilmington, Del.
- Water contact angle measurements are used to test for the migration of additive to the surface of the compression molded sheet samples. Testing is performed by a Ramo-Hart Standard Automated Goniometer Model 200 employing DROPimage standard software and equipped with an automated dispensing system, 250 μl syringe, and illuminated specimen stage assembly is used. The goniometer camera is connected through an interface to a computer, allowing the droplet to be visualized on a computer screen. The horizontal axis line and the cross line can both be independently adjusted on the computer screen using the software.
- Prior to contact angle measurement, the sample is placed on the sample stage and the vertical vernier is adjusted to align the horizontal line (axis) of the eye piece coincident to the horizontal plane of the sample. The horizontal position of the stage relative to the eye piece is positioned so as to view one side of the test fluid droplet interface region at the sample interface.
- To determine the contact angle of the test fluid on the sample, approximately one drop of test fluid is dispensed onto the sample using a 30 μL pipette tip and an automated dispensing system to displace a calibrated amount of the test fluid. Deionized water is used for water contact angle measurements. Horizontal and cross lines are adjusted via the software in case of the Model 200 after leveling the sample via stage adjustment, and the computer calculates the contact angle based upon modeling the drop appearance. The initial contact angle is the angle determined immediately after dispensing the test fluid to the sample surface. Initial contact angles above 30 degrees are indicators of effective oil repellency.
- The friction coefficient was measured according to ASTM D1894 “Standard Test Method for Static and Kinetic Coefficients of Friction of Plastic Film and Sheeting”.
- The sample is cut to a size of 250 mm×130 mm and secured on the test plane. A second test piece is cut to 120 mm square if the specimen is defined as a film, and 63.5 mm square if defined as sheeting, and attached to the sled. Care is taken not to contaminate the test pieces by handling or foreign matter and condition according to ASTM D618.
- The sled is attached to the friction tester crosshead, and the driving mechanism is set to a speed of 150±30 mm/min (6.0±1.2 in./min). The initial maximum force reading is recorded, which is the static frictional force. The sliding is continued for another 130 mm. An average force reading is obtained for the kinetic friction. Five data sets are taken on separate samples. The mean coefficient of friction is calculated as μ=F/mg, where mg is the sled weight.
- There are seven stains used to evaluate easy clean performance on untreated and treated shims, including grape juice, ketchup, corn oil, mustard, cola, coffee, and ink. The stains were applied in the same layout for each substrate, using a disposable pipette. The volume of the stains applied with a pipette was about 50 μL in order to keep the stain quantity and drop size consistent. The stains were left to dwell for about 15 hours. Using an aspirator, the liquid stains were vacuumed one at a time, wiping the end of the tubing to avoid contaminating different stains.
- Once all of the solid and liquid stains were removed, the substrate was placed under a running faucet with warm water to remove some of the stains, and the substrate was wiped and dried with a SONTARA wipe. The samples were placed on the lab bench face up to dry for 4 hours.
- Rating Performance:
- After the tile is dry rate the stains on a score of 0-4.
- 0—No visible stain
- 1—Slight stain perceptible
- 2—Visible stain without clearly defined outline
- 3—Stain with a clearly defined outline but not very deep in color
- 4—Stain with a clearly defined outline, deep in color or stains that penetrated the tile.
- Percent Easy Clean Factor (% ECF) is calculated as % ECF=[(40−sum of scores)/40]*100%. A higher % ECF indicates better stain release.
- Pellets of HYTREL 3078 were dried at 130° F. and blended with sorbitan tristearate, which was in the form of a dry powder, to yield a blend of 2.5% by weight sorbitan tristearate (Example 1) and 5% by weight sorbitan tristearate (Example 2). The powder/pellet blends were fed to a Davis Standard 1.5″ extruder operating at 25 rpm. The extruder had a length/diameter ratio of 24:1 and was equipped with a screw fitted with a Saxton mixer located at the end of the metering section in order to provide uniform temperature and dispersion of the additives within the melt. The compression ratio of the screw (depth of the feed section to the depth of the metering section) was approximately 3.2 to 1. The temperature profile for the extruder was kept at or below 410° F. (210° C.) to minimize any potential thermal degradation.
- Extrudate was processed on a wire-line to produce an insulation ˜25 mil (˜0.64 mm) in thickness on a 7 stranded 18 AWG bare copper conductor have a diameter of ˜48 mils (˜1.2 mm). The material was extruded onto wire at a speeds of ˜60 to 65 ft/min via a tubing configuration consisting of a die have an inner diameter of 180 mils (4.6 mm) and a guider tip outer diameter of 90 mils (2.3 mm). The die and guider tip combinations yielded draw down ratios (cross-sectional area of the die area/cross-sectional area of the finished extrudate) of ˜3.5.
- Additionally, extrudate was collected to be utilized in post extrusion molding operations to create small flat sheets for testing. The resulting extrudates were dried overnight at 130° F. where they were compression molded into sheets approximately 6 inches (˜152 mm) square with a thickness of ˜30 mils (˜0.76 mm). Approximately 16.5 to 17 grams of material was placed between two sheets of polytetrafluoroethylene (PTFE) within a picture frame shim used to achieve the desired dimensions. The stack consisting of the PTFE sheeting, shim, and material was placed between 2 metal plates and then transferred to a hot press with platens set to a temperature of 392° F. (200° C.). The pressure within the press was raised and maintained at ˜5 lbs for a time period of 8 minutes. After this time period allowing the material to soften, the pressure was raised to 10 tons and released multiple times within a one minute period and then maintained at 10 tons for an additional minute allowing the material to flow and acquire the desired dimensions. The pressure was then released and the stack transferred to a water cooled press where the material was held for approximately 5 minutes under low pressure until the sample cooled for removal from the shims. The sheets were tested according to the test methods above.
- Example 1 was repeated, without the addition of sorbitan tristearate.
-
TABLE 1 Contact Angle and Friction Coefficient Measurement of Sheets Example Water Contact Angle Coefficient of Friction 1 134.75 0.314 2 136.00 0.383 A 116.43 0.479 -
TABLE 2 Stain Cleanability Ratings of Sheets Example A 1 2 Grape juice 1 0 0 ketchup 2 0 0 Corn oil 2 2 2 Mustard 4 4 3 Coke 0 0 0 Coffee 3 1 2 Ink 0 0 0 Average Rating 1.71 1.00 1.00 % ECF 66.67 80.56 80.56 -
TABLE 3 Stain Cleanability Ratings of Extruded Wire Example A 1 2 Grape juice 1 0 0 ketchup 2 0 0 Corn oil 2 2 2 Mustard 4 4 3 Coke 0 0 0 Coffee 3 1 2 Ink 0 0 0 Average Rating 1.71 1.00 1.00 % ECF 66.67 80.56 80.56
Claims (14)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US17/228,835 US20210230395A1 (en) | 2015-10-02 | 2021-04-13 | Solid polymeric articles having hydrophobic compounds intermixed therein |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201562236335P | 2015-10-02 | 2015-10-02 | |
PCT/US2016/054584 WO2017059157A1 (en) | 2015-10-02 | 2016-09-30 | Solid polymeric articles having hydrophobic compounds intermixed therein |
US201815764901A | 2018-03-30 | 2018-03-30 | |
US17/228,835 US20210230395A1 (en) | 2015-10-02 | 2021-04-13 | Solid polymeric articles having hydrophobic compounds intermixed therein |
Related Parent Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US15/764,901 Division US11008439B2 (en) | 2015-10-02 | 2016-09-30 | Solid polymeric articles having hydrophobic compounds intermixed therein |
PCT/US2016/054584 Division WO2017059157A1 (en) | 2015-10-02 | 2016-09-30 | Solid polymeric articles having hydrophobic compounds intermixed therein |
Publications (1)
Publication Number | Publication Date |
---|---|
US20210230395A1 true US20210230395A1 (en) | 2021-07-29 |
Family
ID=57211568
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US15/764,901 Active 2037-04-12 US11008439B2 (en) | 2015-10-02 | 2016-09-30 | Solid polymeric articles having hydrophobic compounds intermixed therein |
US17/228,835 Abandoned US20210230395A1 (en) | 2015-10-02 | 2021-04-13 | Solid polymeric articles having hydrophobic compounds intermixed therein |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US15/764,901 Active 2037-04-12 US11008439B2 (en) | 2015-10-02 | 2016-09-30 | Solid polymeric articles having hydrophobic compounds intermixed therein |
Country Status (8)
Country | Link |
---|---|
US (2) | US11008439B2 (en) |
EP (1) | EP3356460A1 (en) |
JP (2) | JP2018529825A (en) |
KR (2) | KR102307784B1 (en) |
CN (1) | CN108137856B (en) |
HK (1) | HK1251242A1 (en) |
TW (1) | TWI790986B (en) |
WO (1) | WO2017059157A1 (en) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP3356460A1 (en) * | 2015-10-02 | 2018-08-08 | The Chemours Company FC, LLC | Solid polymeric articles having hydrophobic compounds intermixed therein |
CN115461161A (en) | 2020-08-26 | 2022-12-09 | 株式会社Lg新能源 | Multi-slit die coating machine |
WO2022055886A1 (en) | 2020-09-09 | 2022-03-17 | The Chemours Company Fc, Llc | Silicone polyether polymer additives in coatings |
WO2024137465A1 (en) | 2022-12-19 | 2024-06-27 | Avient Corporation | Non-fluorinated hydrophobic thermoplastic compositions containing fatty acid ester and articles formed therefrom |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2000319479A (en) * | 1998-12-28 | 2000-11-21 | Taiyo Enbi Kk | Vinyl chloride polymer composition |
US20070287782A1 (en) * | 2006-06-08 | 2007-12-13 | Peter Frenkel | Polymeric component and its applications in rigid PVC |
US11008439B2 (en) * | 2015-10-02 | 2021-05-18 | The Chemours Company Fc, Llc | Solid polymeric articles having hydrophobic compounds intermixed therein |
Family Cites Families (57)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1049126A (en) | 1963-08-08 | 1966-11-23 | Witco Chemical Corp | Improvements in or relating to foamed plastics |
US3427265A (en) | 1965-11-09 | 1969-02-11 | Du Pont | Composition of matter containing wax and a resinous copolymer of ethylene |
US5228157A (en) | 1989-05-18 | 1993-07-20 | Advanced Sleep Products | Soft-sided mattress with integral foam hook construction |
JP2863021B2 (en) | 1990-07-27 | 1999-03-03 | ポリプラスチックス株式会社 | Polybutylene terephthalate resin composition |
JP2863022B2 (en) * | 1990-08-14 | 1999-03-03 | ポリプラスチックス株式会社 | Polyester resin composition |
JPH04218650A (en) | 1990-12-18 | 1992-08-10 | Kawasaki Steel Corp | Hot dip metal coating method |
JP3059816B2 (en) * | 1992-03-14 | 2000-07-04 | 鐘紡株式会社 | Anti-scale adhesive polypropylene resin composition |
JP3299788B2 (en) * | 1992-10-23 | 2002-07-08 | 住友大阪セメント株式会社 | Antibacterial and antifungal resin products |
DE4303556C1 (en) | 1993-02-08 | 1994-10-27 | Bayer Ag | Hard polyurethanes or polyurethane foams |
DE4315841A1 (en) | 1993-05-12 | 1994-11-17 | Bayer Ag | Hard hyrophobic polyurethanes |
US6150020A (en) | 1993-09-23 | 2000-11-21 | Bba Nonwovens Simpsonville, Inc. | Articles exhibiting improved hydrophobicity |
IT1274003B (en) | 1994-05-06 | 1997-07-14 | Coim Spa | PREPARATION OF RIGID POLYURETHANE FOAMS WITH THE USE OF POLYESTER POLYESTERS |
JPH08198997A (en) * | 1995-01-26 | 1996-08-06 | Dainippon Ink & Chem Inc | Foaming beads of vinyl resin |
JPH1036664A (en) * | 1996-07-30 | 1998-02-10 | Mitsubishi Eng Plast Kk | Vibration-fused hollow molding of polyamide resin |
EP1464677B2 (en) | 1996-10-24 | 2016-10-12 | Corning Incorporated | Method for producing low binding surfaces |
JP3857779B2 (en) * | 1997-05-12 | 2006-12-13 | クラリアント インターナショナル リミテッド | Agricultural synthetic resin film with excellent anti-fogging and anti-fogging properties |
EP1170319A1 (en) | 2000-07-03 | 2002-01-09 | Unichema Chemie B.V. | Block copolyester |
US6630528B2 (en) | 2000-08-10 | 2003-10-07 | E. I. Du Pont De Nemours And Company | Antistatic ionomer blend |
US6858290B2 (en) | 2002-05-29 | 2005-02-22 | 3M Innovative Properties Company | Fluid repellent microporous materials |
JP2004209696A (en) * | 2002-12-27 | 2004-07-29 | Shin Etsu Polymer Co Ltd | Stretched film for packaging food |
JP2004250508A (en) | 2003-02-19 | 2004-09-09 | Minoru Hishinuma | Reinforcing material-containing polyurethane foam |
WO2005012429A1 (en) | 2003-07-31 | 2005-02-10 | Dainippon Ink And Chemicals, Inc. | Polyurethane resin formed product and method for production thereof |
JP2005152603A (en) * | 2003-10-31 | 2005-06-16 | Toto Ltd | Resin molding for toilet seat device such as toilet seat and toilet seat lid |
WO2005061571A1 (en) | 2003-12-24 | 2005-07-07 | Nippon Polyurethane Industry Co., Ltd. | Process for producing soft polyurethane foam, process for producing conductive soft polyurethane foam, conductive roll and process for producing the same |
EP1842877A4 (en) * | 2005-01-18 | 2010-12-29 | Toho Chem Ind Co Ltd | Biodegradable polyester resin composition |
US20070004864A1 (en) * | 2005-06-24 | 2007-01-04 | University Of Florida Research Foundation | Method to enhance impact strength properties of melt processed polypropylene resins |
KR100635996B1 (en) | 2005-08-25 | 2006-10-18 | 현대모비스 주식회사 | Composition for aqueous coating for plastic interior in automobile |
US7943296B2 (en) | 2005-12-09 | 2011-05-17 | Oregon Health & Science University | Methods of screening using a natriuretic peptide receptor |
JP2009523921A (en) | 2006-01-17 | 2009-06-25 | インターフェース バイオロジクス,インコーポレーテッド | Alcohol- and water-repellent nonwovens |
PL1984415T3 (en) | 2006-02-15 | 2011-04-29 | Stepan Co | Compatibilizing surfactants for polyurethane polyols and resins |
EP1911781A1 (en) | 2006-10-12 | 2008-04-16 | Arizona Chemical Company | Oil absorbing foam |
JP2009051881A (en) * | 2007-08-24 | 2009-03-12 | Toho Chem Ind Co Ltd | Non-dropping property-imparting composition |
JP5298516B2 (en) * | 2007-12-06 | 2013-09-25 | パナソニック株式会社 | Antifouling resin composition and home appliance housing or toilet seat using antifouling resin composition |
KR101291839B1 (en) | 2009-02-06 | 2013-07-31 | 더 프록터 앤드 갬블 캄파니 | Foundation compositions comprising water repelling silicone elastomer powders |
US8026188B2 (en) | 2009-06-25 | 2011-09-27 | Techmer Pm, Llc | Hydrophobic additive for use with fabric, fiber, and film |
US20120010307A1 (en) | 2010-07-07 | 2012-01-12 | Lifoam Industries | Expandable Beads of a Compostable or Biobased Thermoplastic Polymer |
WO2012020826A1 (en) | 2010-08-11 | 2012-02-16 | 株式会社ブリヂストン | Rubber composition, method for preventing discoloration of rubber composition, and tire |
JP5731768B2 (en) | 2010-08-11 | 2015-06-10 | 株式会社ブリヂストン | Rubber composition and tire |
US9321897B2 (en) | 2011-10-26 | 2016-04-26 | Japan Polypropylene Corporation | Thermoplastic resin composition and toilet components made therefrom |
JP5936953B2 (en) | 2011-12-12 | 2016-06-22 | 第一工業製薬株式会社 | Polylactic acid resin composition and resin molded body thereof |
JP6087636B2 (en) | 2012-07-30 | 2017-03-01 | ダンロップスポーツ株式会社 | Golf ball resin composition and golf ball |
KR101422918B1 (en) | 2012-09-05 | 2014-07-23 | 삼성전기주식회사 | Super hydrophobic membrane and manufacturing method thereof |
DE102012215881A1 (en) * | 2012-09-07 | 2014-03-13 | Wacker Chemie Ag | Porous membranes of crosslinkable silicone compositions |
DE102013201825A1 (en) | 2013-02-05 | 2014-08-07 | Evonik Industries Ag | Composition for use in the manufacture of polyurethane systems |
WO2014136842A1 (en) | 2013-03-06 | 2014-09-12 | 新日本理化株式会社 | Diacetal-containing composition, polyolefin resin composition, and resin molded article |
US10138392B2 (en) | 2013-03-29 | 2018-11-27 | The Chemours Company Fc, Llc | Non-fluorinated urethane based coatings |
US20140296386A1 (en) * | 2013-03-29 | 2014-10-02 | Toray Resin Company | Thermoplastic polyester resin composition and molded article thereof |
US9260605B2 (en) * | 2013-03-29 | 2016-02-16 | The Chemours Company Fc, Llc | Urethane based extenders for surface effect compositions |
DE102013207117A1 (en) | 2013-04-19 | 2014-10-23 | Evonik Industries Ag | PUR foam with coarsened cell structure |
US9550911B2 (en) | 2013-08-21 | 2017-01-24 | The United States of America as represented by the Administrtor of the National Aeronautics and Space Administration | Fluorinated alkyl ether epoxy resin compositions and applications thereof |
US20150080518A1 (en) * | 2013-09-16 | 2015-03-19 | Sabic Innovative Plastics Ip B.V. | Fiber reinforced thermoplastic resin compositions |
CN103642200B (en) | 2013-12-20 | 2016-01-06 | 山东美瑞新材料有限公司 | A kind of foamed thermoplastic polyurethane bead and preparation method thereof |
CN103804889B (en) | 2014-02-18 | 2016-01-27 | 山东美瑞新材料有限公司 | A kind of foamed thermoplastic polyurethane particle and its preparation method and application |
KR102470190B1 (en) | 2014-09-26 | 2022-11-24 | 더 케무어스 컴퍼니 에프씨, 엘엘씨 | Non-fluorinated monomers and polymers for surface effect compositions |
KR20220165837A (en) | 2014-09-26 | 2022-12-15 | 더 케무어스 컴퍼니 에프씨, 엘엘씨 | Non-fluorinated urethane based coatings |
WO2018232968A1 (en) | 2017-06-20 | 2018-12-27 | 唐靖 | Thermoplastic polyester elastomer foaming precursor, foam and preparation methods therefor |
CN107400350B (en) | 2017-06-30 | 2020-02-21 | 南京工业大学 | High-water-absorptivity and high-water-retention polyurethane foam and preparation method thereof |
-
2016
- 2016-09-30 EP EP16788590.4A patent/EP3356460A1/en not_active Withdrawn
- 2016-09-30 WO PCT/US2016/054584 patent/WO2017059157A1/en active Application Filing
- 2016-09-30 JP JP2018516746A patent/JP2018529825A/en active Pending
- 2016-09-30 KR KR1020207025995A patent/KR102307784B1/en active IP Right Grant
- 2016-09-30 US US15/764,901 patent/US11008439B2/en active Active
- 2016-09-30 CN CN201680059135.2A patent/CN108137856B/en active Active
- 2016-09-30 KR KR1020187011944A patent/KR102156595B1/en active IP Right Grant
- 2016-10-03 TW TW105131882A patent/TWI790986B/en active
-
2018
- 2018-08-16 HK HK18110514.6A patent/HK1251242A1/en unknown
-
2021
- 2021-02-19 JP JP2021025416A patent/JP2021088720A/en active Pending
- 2021-04-13 US US17/228,835 patent/US20210230395A1/en not_active Abandoned
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2000319479A (en) * | 1998-12-28 | 2000-11-21 | Taiyo Enbi Kk | Vinyl chloride polymer composition |
US20070287782A1 (en) * | 2006-06-08 | 2007-12-13 | Peter Frenkel | Polymeric component and its applications in rigid PVC |
US11008439B2 (en) * | 2015-10-02 | 2021-05-18 | The Chemours Company Fc, Llc | Solid polymeric articles having hydrophobic compounds intermixed therein |
Non-Patent Citations (1)
Title |
---|
English Machine Translation of JP 2000-319479 (Year: 2000) * |
Also Published As
Publication number | Publication date |
---|---|
US11008439B2 (en) | 2021-05-18 |
KR102307784B1 (en) | 2021-10-05 |
CN108137856B (en) | 2021-05-04 |
KR102156595B1 (en) | 2020-09-16 |
HK1251242A1 (en) | 2019-01-25 |
JP2018529825A (en) | 2018-10-11 |
KR20180059885A (en) | 2018-06-05 |
WO2017059157A1 (en) | 2017-04-06 |
KR20200108112A (en) | 2020-09-16 |
TW201731936A (en) | 2017-09-16 |
EP3356460A1 (en) | 2018-08-08 |
US20180282514A1 (en) | 2018-10-04 |
TWI790986B (en) | 2023-02-01 |
JP2021088720A (en) | 2021-06-10 |
CN108137856A (en) | 2018-06-08 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US20210230395A1 (en) | Solid polymeric articles having hydrophobic compounds intermixed therein | |
EP3197963B1 (en) | Non-fluorinated monomers and polymers for surface effect compositions | |
US20180282571A1 (en) | Hydrophobic compound extenders in surface effect coatings | |
EP2039718A2 (en) | Quickly coagulating softener preparations | |
JP6659740B2 (en) | Plasticizer composition | |
EP2723749B1 (en) | Dianhydrohexitol diesters of 2-ethylheptanoic acid | |
EP3356474B1 (en) | Coatings incorporating hydrophobic compounds | |
EP2404962B1 (en) | Softener preparations with good gelling characteristics | |
JP7066107B2 (en) | Polyvinyl chloride resin composition | |
DE102008000465A1 (en) | Polymer blends containing polyorganosiloxane-polyurea copolymers | |
KR101679654B1 (en) | Plasticizers for resin compositions and resin compositions including the same | |
KR100560290B1 (en) | Polyvinyl Chloride Resin Composition for Environment-Friendly Wrap Film | |
CN110494460A (en) | Polymer composition | |
JP2021095482A (en) | Methacrylic resin composition, molding, and vehicle member | |
US20190256729A1 (en) | Coatings incorporating non-fluorinated cleanability additives | |
JP2599904B2 (en) | Chlorine-containing resin molded product | |
US20180320309A1 (en) | Carpet with hydrophobic surface finish | |
JP2023054874A (en) | plastic eraser | |
EP3699229A1 (en) | Powder slush-molded article of vinyl chloride-based resin composition and laminate | |
WO2013026917A1 (en) | Polyalkylene glycol-di-p-toluates and -benzoates, method for the production thereof and their use |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
STPP | Information on status: patent application and granting procedure in general |
Free format text: APPLICATION DISPATCHED FROM PREEXAM, NOT YET DOCKETED |
|
STPP | Information on status: patent application and granting procedure in general |
Free format text: DOCKETED NEW CASE - READY FOR EXAMINATION |
|
AS | Assignment |
Owner name: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT, NEW YORK Free format text: SECURITY INTEREST;ASSIGNOR:THE CHEMOURS COMPANY FC, LLC;REEL/FRAME:059552/0001 Effective date: 20220301 |
|
STPP | Information on status: patent application and granting procedure in general |
Free format text: NON FINAL ACTION MAILED |
|
STPP | Information on status: patent application and granting procedure in general |
Free format text: RESPONSE TO NON-FINAL OFFICE ACTION ENTERED AND FORWARDED TO EXAMINER |
|
STPP | Information on status: patent application and granting procedure in general |
Free format text: FINAL REJECTION MAILED |
|
STCB | Information on status: application discontinuation |
Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION |