AU2007277156A1 - Polytrimethylene ether-based polyurethane ionomers - Google Patents
Polytrimethylene ether-based polyurethane ionomers Download PDFInfo
- Publication number
- AU2007277156A1 AU2007277156A1 AU2007277156A AU2007277156A AU2007277156A1 AU 2007277156 A1 AU2007277156 A1 AU 2007277156A1 AU 2007277156 A AU2007277156 A AU 2007277156A AU 2007277156 A AU2007277156 A AU 2007277156A AU 2007277156 A1 AU2007277156 A1 AU 2007277156A1
- Authority
- AU
- Australia
- Prior art keywords
- polyurethane
- ionic
- groups
- less
- polytrimethylene ether
- 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
- 229920002635 polyurethane Polymers 0.000 title claims description 134
- 239000004814 polyurethane Substances 0.000 title claims description 134
- -1 Polytrimethylene Polymers 0.000 title claims description 81
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title claims description 60
- 229920000554 ionomer Polymers 0.000 title claims description 11
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 71
- 239000006185 dispersion Substances 0.000 claims description 53
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims description 45
- 239000000203 mixture Substances 0.000 claims description 45
- 229920000166 polytrimethylene carbonate Polymers 0.000 claims description 45
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 claims description 43
- 229940035437 1,3-propanediol Drugs 0.000 claims description 43
- 238000000034 method Methods 0.000 claims description 43
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 43
- 150000002009 diols Chemical class 0.000 claims description 38
- 239000012948 isocyanate Substances 0.000 claims description 35
- 150000003077 polyols Chemical class 0.000 claims description 35
- 229920005862 polyol Polymers 0.000 claims description 34
- 239000000376 reactant Substances 0.000 claims description 31
- 150000001875 compounds Chemical class 0.000 claims description 29
- 150000002513 isocyanates Chemical class 0.000 claims description 29
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 28
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 23
- 125000003010 ionic group Chemical group 0.000 claims description 19
- 125000005442 diisocyanate group Chemical group 0.000 claims description 18
- 239000005056 polyisocyanate Substances 0.000 claims description 14
- 229920001228 polyisocyanate Polymers 0.000 claims description 14
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical group C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 claims description 13
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- 230000003472 neutralizing effect Effects 0.000 claims description 10
- 239000004615 ingredient Substances 0.000 claims description 9
- 239000003960 organic solvent Substances 0.000 claims description 9
- 125000000129 anionic group Chemical group 0.000 claims description 8
- 229920001730 Moisture cure polyurethane Polymers 0.000 claims description 6
- 239000012736 aqueous medium Substances 0.000 claims description 6
- 239000007795 chemical reaction product Substances 0.000 claims description 5
- 238000002835 absorbance Methods 0.000 claims description 3
- 238000010521 absorption reaction Methods 0.000 claims description 3
- 238000004817 gas chromatography Methods 0.000 claims description 3
- 239000012535 impurity Substances 0.000 claims description 3
- 150000002894 organic compounds Chemical class 0.000 claims description 3
- 150000002978 peroxides Chemical class 0.000 claims description 3
- 210000000988 bone and bone Anatomy 0.000 claims description 2
- 230000002844 continuous effect Effects 0.000 claims description 2
- 239000000306 component Substances 0.000 description 42
- 239000002253 acid Substances 0.000 description 31
- 229920000642 polymer Polymers 0.000 description 31
- 238000006243 chemical reaction Methods 0.000 description 28
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 20
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 19
- 229920003009 polyurethane dispersion Polymers 0.000 description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- 239000004970 Chain extender Substances 0.000 description 18
- 238000004132 cross linking Methods 0.000 description 18
- 239000007787 solid Substances 0.000 description 18
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 17
- 229920000768 polyamine Polymers 0.000 description 17
- 230000008569 process Effects 0.000 description 17
- 239000002904 solvent Substances 0.000 description 17
- 241000196324 Embryophyta Species 0.000 description 16
- 238000007792 addition Methods 0.000 description 15
- 229910052799 carbon Inorganic materials 0.000 description 15
- 239000002245 particle Substances 0.000 description 15
- 150000001412 amines Chemical class 0.000 description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 13
- 238000002360 preparation method Methods 0.000 description 13
- 239000000463 material Substances 0.000 description 12
- 238000002156 mixing Methods 0.000 description 11
- 229920000728 polyester Polymers 0.000 description 11
- 150000007513 acids Chemical class 0.000 description 10
- 239000007858 starting material Substances 0.000 description 10
- 125000001931 aliphatic group Chemical group 0.000 description 9
- 229920000570 polyether Polymers 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 8
- PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 description 7
- 239000005058 Isophorone diisocyanate Substances 0.000 description 7
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 7
- 150000001298 alcohols Chemical class 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 7
- 125000002091 cationic group Chemical group 0.000 description 7
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 7
- 238000006386 neutralization reaction Methods 0.000 description 7
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 description 7
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000004721 Polyphenylene oxide Substances 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 229940022682 acetone Drugs 0.000 description 6
- 125000003277 amino group Chemical group 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 230000007613 environmental effect Effects 0.000 description 6
- 235000011187 glycerol Nutrition 0.000 description 6
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- 229920000515 polycarbonate Polymers 0.000 description 6
- 239000004417 polycarbonate Substances 0.000 description 6
- 229920001223 polyethylene glycol Polymers 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000004094 surface-active agent Substances 0.000 description 6
- IBZKBSXREAQDTO-UHFFFAOYSA-N 2-methoxy-n-(2-methoxyethyl)ethanamine Chemical compound COCCNCCOC IBZKBSXREAQDTO-UHFFFAOYSA-N 0.000 description 5
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 5
- 239000002202 Polyethylene glycol Substances 0.000 description 5
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- 229910002092 carbon dioxide Inorganic materials 0.000 description 5
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 150000003512 tertiary amines Chemical class 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 150000007942 carboxylates Chemical group 0.000 description 4
- 238000006473 carboxylation reaction Methods 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 230000000295 complement effect Effects 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 230000000875 corresponding effect Effects 0.000 description 4
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 4
- 239000012975 dibutyltin dilaurate Substances 0.000 description 4
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 239000002803 fossil fuel Substances 0.000 description 4
- 150000002334 glycols Chemical class 0.000 description 4
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 230000000243 photosynthetic effect Effects 0.000 description 4
- 229920005906 polyester polyol Polymers 0.000 description 4
- 229920000193 polymethacrylate Polymers 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 3
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- 239000001569 carbon dioxide Substances 0.000 description 3
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 150000004985 diamines Chemical class 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 238000006068 polycondensation reaction Methods 0.000 description 3
- 229920001451 polypropylene glycol Polymers 0.000 description 3
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- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 3
- 235000015112 vegetable and seed oil Nutrition 0.000 description 3
- 239000008158 vegetable oil Substances 0.000 description 3
- KMOUUZVZFBCRAM-UHFFFAOYSA-N 1,2,3,6-tetrahydrophthalic anhydride Chemical compound C1C=CCC2C(=O)OC(=O)C21 KMOUUZVZFBCRAM-UHFFFAOYSA-N 0.000 description 2
- ARXKVVRQIIOZGF-UHFFFAOYSA-N 1,2,4-butanetriol Chemical compound OCCC(O)CO ARXKVVRQIIOZGF-UHFFFAOYSA-N 0.000 description 2
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 2
- VZXPHDGHQXLXJC-UHFFFAOYSA-N 1,6-diisocyanato-5,6-dimethylheptane Chemical compound O=C=NC(C)(C)C(C)CCCCN=C=O VZXPHDGHQXLXJC-UHFFFAOYSA-N 0.000 description 2
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 2
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 2
- IBOFVQJTBBUKMU-UHFFFAOYSA-N 4,4'-methylene-bis-(2-chloroaniline) Chemical compound C1=C(Cl)C(N)=CC=C1CC1=CC=C(N)C(Cl)=C1 IBOFVQJTBBUKMU-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 241001550224 Apha Species 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 239000004971 Cross linker Substances 0.000 description 2
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical group CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/4009—Two or more macromolecular compounds not provided for in one single group of groups C08G18/42 - C08G18/64
- C08G18/4018—Mixtures of compounds of group C08G18/42 with compounds of group C08G18/48
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/63—Block or graft polymers obtained by polymerising compounds having carbon-to-carbon double bonds on to polymers
- C08G18/637—Block or graft polymers obtained by polymerising compounds having carbon-to-carbon double bonds on to polymers characterised by the in situ polymerisation of the compounds having carbon-to-carbon double bonds in a reaction mixture of saturated polymers and isocyanates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6625—Compounds of groups C08G18/42, C08G18/48, or C08G18/52 with compounds of group C08G18/34
-
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
- C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
- C08G18/752—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
- C08G18/753—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group
- C08G18/755—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7614—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring
- C08G18/7621—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring being toluene diisocyanate including isomer mixtures
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7614—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring
- C08G18/7628—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring containing at least one isocyanate or isothiocyanate group linked to the aromatic ring by means of an aliphatic group
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Dispersion Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Polyurethanes Or Polyureas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US83401406P | 2006-07-28 | 2006-07-28 | |
| US60/834,014 | 2006-07-28 | ||
| PCT/US2007/016874 WO2008013924A1 (en) | 2006-07-28 | 2007-07-27 | Polytrimethylene ether-based polyurethane ionomers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2007277156A1 true AU2007277156A1 (en) | 2008-01-31 |
Family
ID=38659652
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2007277156A Abandoned AU2007277156A1 (en) | 2006-07-28 | 2007-07-27 | Polytrimethylene ether-based polyurethane ionomers |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US20080039582A1 (enExample) |
| EP (1) | EP2046851A1 (enExample) |
| JP (1) | JP5399241B2 (enExample) |
| KR (1) | KR101433398B1 (enExample) |
| CN (1) | CN101495530A (enExample) |
| AU (1) | AU2007277156A1 (enExample) |
| BR (1) | BRPI0713813A2 (enExample) |
| CA (1) | CA2659031A1 (enExample) |
| MX (1) | MX2009000984A (enExample) |
| WO (1) | WO2008013924A1 (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US20120077929A1 (en) * | 2006-07-28 | 2012-03-29 | E. I. Du Pont De Nemours And Company | Polytrimethylene ether-based polyurethane ionomers |
| US20080175875A1 (en) * | 2006-09-25 | 2008-07-24 | Hari Babu Sunkara | Cosmetic compositions |
| US20090123688A1 (en) * | 2007-11-08 | 2009-05-14 | Miller Ray W | Moisture vapor permeable carpet underlay |
| US20100093927A1 (en) * | 2007-12-10 | 2010-04-15 | Roberts C Chad | Polyurethanes with Nonionic Hydrophilic Terminating Groups and Aqueous Dispersions Thereof |
| US20130022746A9 (en) * | 2007-12-10 | 2013-01-24 | Harry Joseph Spinelli | Aqueous inkjet inks with ionically stabilized dispersions and polyurethane ink additives |
| US9410010B2 (en) | 2007-12-10 | 2016-08-09 | E I Du Pont De Nemours And Company | Urea-terminated polyurethane dispersants |
| US20090259012A1 (en) * | 2007-12-10 | 2009-10-15 | Roberts C Chad | Urea-terminated ether polyurethanes and aqueous dispersions thereof |
| EP2285918B1 (en) * | 2008-05-23 | 2012-08-01 | E. I. du Pont de Nemours and Company | Inkjet ink with self dispersed pigments and polyurethane ink additives |
| US8759418B2 (en) * | 2008-05-23 | 2014-06-24 | E I Du Pont De Nemours And Company | Urea-terminated polyurethane dispersants |
| US20100055471A1 (en) * | 2008-09-02 | 2010-03-04 | Ppg Industries Ohio, Inc. | Waterborne polyurethane dispersion comprising biomass derived polyol and coatings comprising same |
| CN101412798B (zh) * | 2008-11-21 | 2011-08-10 | 优洁(亚洲)有限公司 | 软质聚氨酯低回弹泡沫及其制备方法 |
| US20110130218A1 (en) * | 2009-12-02 | 2011-06-02 | Murali Rajagopalan | Golf balls comprising polytrimethylene ether amine-based polyurea compositions |
| KR101518108B1 (ko) * | 2010-07-01 | 2015-05-06 | 주식회사 동성하이켐 | 스커프 저항성과 반발탄성이 우수한 골프공 용 친환경 열가소성 폴리우레탄 수지 조성물 및 그 제조방법 |
| US20130201250A1 (en) * | 2010-10-29 | 2013-08-08 | E I Du Pont De Nemours And Company | Polyurethane dispersants based on asymmetric branched trisubstituted isocyanate reactive compounds. |
| TW201221549A (en) | 2010-11-19 | 2012-06-01 | Du Pont | Blends comprising branched poly (trimethylene ether) polyols |
| WO2013090398A1 (en) * | 2011-12-12 | 2013-06-20 | U.S. Coatings Ip Co. Llc | Waterborne coating composition containing bio-resourced polytrimethylene ether polyol |
| DE102012219476A1 (de) * | 2012-10-24 | 2014-04-24 | Hilti Aktiengesellschaft | Harzmischung auf Vinylesterurethanharz-Basis und deren Verwendung |
| ES2745033T3 (es) * | 2013-02-18 | 2020-02-27 | Danimer Scient Llc | Composición adhesiva y método |
| WO2016159723A1 (ko) * | 2015-04-01 | 2016-10-06 | 주식회사 삼양사 | 폴리우레탄, 그 제조방법 및 용도 |
| NL2022275B1 (en) * | 2018-12-21 | 2020-07-15 | Stahl Int B V | Process to prepare halogen-free, flame-retardant aqueous polyurethane dispersions |
| JP7459626B2 (ja) * | 2020-04-02 | 2024-04-02 | artience株式会社 | 水性グラビアまたはフレキソインキ、およびその利用 |
| CN114181357A (zh) * | 2021-11-23 | 2022-03-15 | 黄山中泽新材料有限公司 | 一种生物基无溶剂水性聚氨酯乳液及制备印刷油墨的用途 |
| KR102828979B1 (ko) * | 2022-03-29 | 2025-07-04 | (주)건양 | 바이오폴리올을 이용한 수성 폴리우레탄 제조방법 |
| EP4269462A1 (en) * | 2022-04-26 | 2023-11-01 | Henkel AG & Co. KGaA | Two component (2k) acrylic composition comprising a thermoplastic polyurethane |
| CN115806652A (zh) * | 2022-12-14 | 2023-03-17 | 合肥安利聚氨酯新材料有限公司 | 一种低碳环保型聚氨酯树脂及其制备方法 |
| WO2025007874A1 (en) | 2023-07-04 | 2025-01-09 | Covestro Deutschland Ag | A solvent-free polyurethane dispersion based on polytrimethylene ether glycol |
| EP4509540A1 (en) | 2023-08-16 | 2025-02-19 | Covestro Deutschland AG | A solvent-free polyurethane dispersion based on polytrimethylene ether glycol |
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| US4108814A (en) * | 1974-09-28 | 1978-08-22 | Bayer Aktiengesellschaft | Aqueous polyurethane dispersions from solvent-free prepolymers using sulfonate diols |
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| US4701480A (en) * | 1985-09-23 | 1987-10-20 | Mobay Corporation | Stable, aqueous dispersions of polyurethane-ureas |
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| DE3926136A1 (de) * | 1989-08-08 | 1991-02-14 | Degussa | Verfahren zur herstellung von 1,3-propandiol |
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| DE4132663C2 (de) * | 1991-10-01 | 1993-10-14 | Degussa | Verfahren zum Herstellen von 1,3-Propandiol durch Hydrieren von Hydroxypropionaldehyd |
| DE4138982A1 (de) * | 1991-11-27 | 1993-06-03 | Degussa | Verfahren zur herstellung von 3-hydroxyalkanalen |
| DE4138981A1 (de) * | 1991-11-27 | 1993-06-03 | Degussa | Verfahren zur herstellung von 3-hydroxyalkanalen |
| DE4218282A1 (de) * | 1992-06-03 | 1993-12-09 | Degussa | Verfahren zur Herstellung von 1,3-Propandiol |
| DE4222708A1 (de) * | 1992-07-10 | 1994-01-13 | Degussa | Verfahren zur Herstellung von 1,3-Propandiol |
| DE4314111A1 (de) * | 1993-04-29 | 1994-11-03 | Goldschmidt Ag Th | alpha,omega-Polymethacrylatdiole, Verfahren zu ihrer Herstellung und deren Verwendung zur Herstellung von Polymeren, insbesondere Polyurethanen und Polyestern |
| US5554686A (en) * | 1993-08-20 | 1996-09-10 | Minnesota Mining And Manufacturing Company | Room temperature curable silane-terminated polyurethane dispersions |
| US5488383A (en) * | 1994-01-21 | 1996-01-30 | Lockheed Missiles & Space Co., Inc. | Method for accurizing mesh fabric reflector panels of a deployable reflector |
| DE4406547A1 (de) * | 1994-02-28 | 1995-08-31 | Herberts Gmbh | Wäßrige Polyurethanharzdispersion, deren Herstellung und hierzu geeignete Polyurethanmakromere, und ihre Verwendung in wäßrigen Überzugsmitteln |
| DE4413562A1 (de) * | 1994-04-19 | 1995-10-26 | Herberts Gmbh | Wäßrige Dispersion von Siloxanbrücken enthaltenden Polyurethanen, deren Herstellung und Verwendung in Überzugsmitteln |
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| US5576382A (en) * | 1996-05-05 | 1996-11-19 | Arco Chemical Technology, L.P. | Aqueous polyurethane dispersions based on polyether polyols of low monol content |
| DE19703383A1 (de) * | 1997-01-30 | 1998-08-06 | Degussa | Verfahren zur Herstellung von 1,3-Propandiol |
| DE19705470A1 (de) * | 1997-02-13 | 1998-08-27 | Goldschmidt Ag Th | Polymethacrylsäure-Polyalkylenoxid-Blockcopolymere, Verfahren zu ihrer Herstellung und ihre Verwendung als Dispergiermittel |
| US5962745A (en) * | 1997-02-14 | 1999-10-05 | E. I. Du Pont De Nemours And Company | Process for preparing 3-hydroxyalkanals |
| KR20010013907A (ko) * | 1997-06-18 | 2001-02-26 | 메리 이. 보울러 | 3-히드록시프로피온알데히드의 수소화에 의한1,3-프로판디올의 제조 방법 |
| DE59803538D1 (de) * | 1997-07-31 | 2002-05-02 | Basf Ag | Wässerige dispersionen enthaltend polyurethane mit carbodiimidgruppen |
| US6235948B1 (en) * | 1998-08-18 | 2001-05-22 | E. I. Du Pont De Nemours And Company | Process for the purification of 1,3-propanediol |
| AU5798199A (en) * | 1998-09-04 | 2000-03-27 | E.I. Du Pont De Nemours And Company | Two-stage process for the production of 1,3-propanediol by catalytic hydrogenation of 3-hydroxypropanal |
| US6331264B1 (en) * | 1999-03-31 | 2001-12-18 | E. I. Du Pont De Nemours And Company | Low emission polymer compositions |
| US6277289B1 (en) * | 1999-07-01 | 2001-08-21 | E. I. Du Pont De Nemours And Company | Treatment of aqueous aldehyde waste streams |
| US6342646B1 (en) * | 1999-07-30 | 2002-01-29 | E. I. Du Pont De Nemours And Company | Catalytic hydrogenation of 3-hydroxypropanal to 1,3-propanediol |
| EP1237835B1 (en) * | 1999-12-17 | 2006-09-20 | E.I. Du Pont De Nemours And Company | Continuous process for the preparation of polytrimethylene ether glycol |
| WO2001044348A1 (en) * | 1999-12-17 | 2001-06-21 | E.I. Du Pont De Nemours And Company | Production of polytrimethylene ether glycol and copolymers thereof |
| US6316586B1 (en) * | 2000-08-15 | 2001-11-13 | E. I. Du Pont De Nemours And Company | Copolyether composition and processes therefor and therewith |
| DE10122444A1 (de) * | 2001-05-09 | 2002-11-14 | Bayer Ag | Polyurethan-Polyharnstoff Dispersionen als Beschichtungsmittel |
| US6608168B1 (en) * | 2002-08-09 | 2003-08-19 | E. I. Du Pont De Nemours And Company | Polytrimethylene ether esters |
| US6946539B2 (en) * | 2002-08-09 | 2005-09-20 | E. I. Du Pont De Nemours And Company | Polyurethane and polyurethane-urea comprised of poly(trimethylene-ethylene ether) glycol soft segment |
| US6852823B2 (en) * | 2002-08-09 | 2005-02-08 | E. I. Du Pont De Nemours And Company | Polyurethane and polyurethane-urea elastomers from polytrimethylene ether glycol |
| US20040030095A1 (en) * | 2002-08-09 | 2004-02-12 | Sunkara Hari B. | Poly(trimethylene-ethylene ether) glycols |
| AU2004223820A1 (en) * | 2003-03-21 | 2004-10-07 | E. I. Du Pont De Nemours And Company | Polytrimethylene ether diol containing coating compositions |
| JP4908218B2 (ja) * | 2003-05-06 | 2012-04-04 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 生化学的に誘導された1,3−プロパンジオールの水素化 |
| US7084311B2 (en) * | 2003-05-06 | 2006-08-01 | E. I. Du Pont De Nemours And Company | Hydrogenation of chemically derived 1,3-propanediol |
| US7323539B2 (en) * | 2003-05-06 | 2008-01-29 | E. I. Du Pont De Nemours And Company | Polytrimethylene ether glycol and polytrimethylene ether ester with excellent quality |
| DE602004028359D1 (de) * | 2003-05-06 | 2010-09-09 | Du Pont | Reinigung von biologisch produziertem 1,3-propandiol |
| US7009082B2 (en) * | 2003-05-06 | 2006-03-07 | E.I. Du Pont De Nemours And Company | Removal of color bodies from polytrimethylene ether glycol polymers |
| US20050090599A1 (en) * | 2003-06-06 | 2005-04-28 | Spinelli Harry J. | Aqueous ionically stabilized dispersions |
| US20050182154A1 (en) * | 2004-01-21 | 2005-08-18 | Berge Charles T. | Inkjet inks containing crosslinked polyurethanes |
| US20070129524A1 (en) * | 2005-12-06 | 2007-06-07 | Sunkara Hari B | Thermoplastic polyurethanes comprising polytrimethylene ether soft segments |
-
2007
- 2007-07-24 US US11/782,098 patent/US20080039582A1/en not_active Abandoned
- 2007-07-27 EP EP07836277A patent/EP2046851A1/en not_active Withdrawn
- 2007-07-27 BR BRPI0713813-0A patent/BRPI0713813A2/pt not_active IP Right Cessation
- 2007-07-27 AU AU2007277156A patent/AU2007277156A1/en not_active Abandoned
- 2007-07-27 CN CNA2007800284444A patent/CN101495530A/zh active Pending
- 2007-07-27 KR KR1020097003624A patent/KR101433398B1/ko not_active Expired - Fee Related
- 2007-07-27 CA CA002659031A patent/CA2659031A1/en not_active Abandoned
- 2007-07-27 JP JP2009522805A patent/JP5399241B2/ja not_active Expired - Fee Related
- 2007-07-27 MX MX2009000984A patent/MX2009000984A/es unknown
- 2007-07-27 WO PCT/US2007/016874 patent/WO2008013924A1/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| CA2659031A1 (en) | 2008-01-31 |
| MX2009000984A (es) | 2009-02-04 |
| CN101495530A (zh) | 2009-07-29 |
| US20080039582A1 (en) | 2008-02-14 |
| EP2046851A1 (en) | 2009-04-15 |
| JP2009544834A (ja) | 2009-12-17 |
| KR101433398B1 (ko) | 2014-08-26 |
| JP5399241B2 (ja) | 2014-01-29 |
| BRPI0713813A2 (pt) | 2012-11-06 |
| KR20090045261A (ko) | 2009-05-07 |
| WO2008013924A1 (en) | 2008-01-31 |
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