CA2839776A1 - Polyurethane urea dispersions - Google Patents
Polyurethane urea dispersions Download PDFInfo
- Publication number
- CA2839776A1 CA2839776A1 CA2839776A CA2839776A CA2839776A1 CA 2839776 A1 CA2839776 A1 CA 2839776A1 CA 2839776 A CA2839776 A CA 2839776A CA 2839776 A CA2839776 A CA 2839776A CA 2839776 A1 CA2839776 A1 CA 2839776A1
- Authority
- CA
- Canada
- Prior art keywords
- polyurethane urea
- functionality
- aqueous polyurethane
- mol
- dispersion according
- 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
- 239000006185 dispersion Substances 0.000 title claims abstract description 52
- 229920003226 polyurethane urea Polymers 0.000 title claims abstract description 33
- 229920005906 polyester polyol Polymers 0.000 claims abstract description 27
- 150000001875 compounds Chemical class 0.000 claims description 32
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 25
- 239000003795 chemical substances by application Substances 0.000 claims description 23
- 239000005056 polyisocyanate Substances 0.000 claims description 16
- 229920001228 polyisocyanate Polymers 0.000 claims description 16
- 238000000576 coating method Methods 0.000 claims description 13
- 125000003010 ionic group Chemical group 0.000 claims description 13
- 239000001384 succinic acid Substances 0.000 claims description 13
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 11
- 230000003472 neutralizing effect Effects 0.000 claims description 11
- 229920000642 polymer Polymers 0.000 claims description 11
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 10
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 239000011248 coating agent Substances 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- 125000001931 aliphatic group Chemical group 0.000 claims description 8
- 239000000123 paper Substances 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 claims description 6
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims description 6
- 230000009477 glass transition Effects 0.000 claims description 6
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 claims description 6
- 229920000768 polyamine Polymers 0.000 claims description 6
- 229920000166 polytrimethylene carbonate Polymers 0.000 claims description 6
- 239000004753 textile Substances 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 238000005259 measurement Methods 0.000 claims description 4
- 239000000758 substrate Substances 0.000 claims description 4
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 3
- 239000003365 glass fiber Substances 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 239000010985 leather Substances 0.000 claims description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 3
- 235000013772 propylene glycol Nutrition 0.000 claims description 3
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 claims description 3
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 claims description 2
- QWGRWMMWNDWRQN-UHFFFAOYSA-N 2-methylpropane-1,3-diol Chemical compound OCC(C)CO QWGRWMMWNDWRQN-UHFFFAOYSA-N 0.000 claims description 2
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 claims description 2
- OWBTYPJTUOEWEK-UHFFFAOYSA-N butane-2,3-diol Chemical compound CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 claims description 2
- FOTKYAAJKYLFFN-UHFFFAOYSA-N decane-1,10-diol Chemical compound OCCCCCCCCCCO FOTKYAAJKYLFFN-UHFFFAOYSA-N 0.000 claims description 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 claims description 2
- 229910002804 graphite Inorganic materials 0.000 claims description 2
- 239000010439 graphite Substances 0.000 claims description 2
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 claims description 2
- 229920003023 plastic Polymers 0.000 claims description 2
- 239000004033 plastic Substances 0.000 claims description 2
- GHLKSLMMWAKNBM-UHFFFAOYSA-N dodecane-1,12-diol Chemical compound OCCCCCCCCCCCCO GHLKSLMMWAKNBM-UHFFFAOYSA-N 0.000 claims 2
- SXFJDZNJHVPHPH-UHFFFAOYSA-N 3-methylpentane-1,5-diol Chemical compound OCCC(C)CCO SXFJDZNJHVPHPH-UHFFFAOYSA-N 0.000 claims 1
- 239000008199 coating composition Substances 0.000 abstract description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 63
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 16
- 238000000034 method Methods 0.000 description 16
- 150000002148 esters Chemical class 0.000 description 15
- -1 for example Substances 0.000 description 15
- 239000000203 mixture Substances 0.000 description 15
- 229920005862 polyol Polymers 0.000 description 15
- 150000003077 polyols Chemical class 0.000 description 15
- 238000002360 preparation method Methods 0.000 description 14
- 239000004814 polyurethane Substances 0.000 description 13
- 238000003756 stirring Methods 0.000 description 12
- 229920002635 polyurethane Polymers 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- 229960005137 succinic acid Drugs 0.000 description 11
- 239000005058 Isophorone diisocyanate Substances 0.000 description 10
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 10
- 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 10
- 239000000047 product Substances 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 229920000728 polyester Polymers 0.000 description 9
- 229920000570 polyether Polymers 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 8
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000002245 particle Substances 0.000 description 8
- 239000004721 Polyphenylene oxide Substances 0.000 description 7
- 230000008569 process Effects 0.000 description 7
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
- 229920002396 Polyurea Polymers 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 125000003277 amino group Chemical group 0.000 description 5
- 125000000129 anionic group Chemical group 0.000 description 5
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 5
- 150000002009 diols Chemical class 0.000 description 5
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 5
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 5
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 4
- 229920001730 Moisture cure polyurethane Polymers 0.000 description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 230000009471 action Effects 0.000 description 4
- 239000001361 adipic acid Substances 0.000 description 4
- 229960000250 adipic acid Drugs 0.000 description 4
- 235000011037 adipic acid Nutrition 0.000 description 4
- 125000002091 cationic group Chemical group 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 229920000058 polyacrylate Polymers 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 239000012855 volatile organic compound Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 230000015572 biosynthetic process Effects 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
- 239000000470 constituent Substances 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 3
- 150000008040 ionic compounds Chemical class 0.000 description 3
- 238000006386 neutralization reaction Methods 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- 229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 description 2
- PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 description 2
- IVGRSQBDVIJNDA-UHFFFAOYSA-N 2-(2-aminoethylamino)ethanesulfonic acid Chemical compound NCCNCCS(O)(=O)=O IVGRSQBDVIJNDA-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 239000001099 ammonium carbonate Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- 150000007942 carboxylates Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 229960002887 deanol Drugs 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- 239000012975 dibutyltin dilaurate Substances 0.000 description 2
- 229940028356 diethylene glycol monobutyl ether Drugs 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000012972 dimethylethanolamine Substances 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- 238000004945 emulsification Methods 0.000 description 2
- 125000001033 ether group Chemical group 0.000 description 2
- 238000012262 fermentative production Methods 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 238000006068 polycondensation reaction Methods 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- FGGPAWQCCGEWTJ-UHFFFAOYSA-M sodium;2,3-bis(sulfanyl)propane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)CC(S)CS FGGPAWQCCGEWTJ-UHFFFAOYSA-M 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 2
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 2
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- UNMJLQGKEDTEKJ-UHFFFAOYSA-N (3-ethyloxetan-3-yl)methanol Chemical compound CCC1(CO)COC1 UNMJLQGKEDTEKJ-UHFFFAOYSA-N 0.000 description 1
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- OOCCDEMITAIZTP-QPJJXVBHSA-N (E)-cinnamyl alcohol Chemical compound OC\C=C\C1=CC=CC=C1 OOCCDEMITAIZTP-QPJJXVBHSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- YOUHVVBPILYPKM-NSCUHMNNSA-N (e)-but-2-ene-1,1-diol Chemical compound C\C=C\C(O)O YOUHVVBPILYPKM-NSCUHMNNSA-N 0.000 description 1
- ORTVZLZNOYNASJ-UPHRSURJSA-N (z)-but-2-ene-1,4-diol Chemical compound OC\C=C/CO ORTVZLZNOYNASJ-UPHRSURJSA-N 0.000 description 1
- AZYRZNIYJDKRHO-UHFFFAOYSA-N 1,3-bis(2-isocyanatopropan-2-yl)benzene Chemical compound O=C=NC(C)(C)C1=CC=CC(C(C)(C)N=C=O)=C1 AZYRZNIYJDKRHO-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
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- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
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- C08G18/4238—Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic groups derived from dicarboxylic acids and dialcohols
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/721—Two or more polyisocyanates not provided for in one single group C08G18/73 - C08G18/80
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
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-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
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- C09D175/04—Polyurethanes
- C09D175/12—Polyurethanes from compounds containing nitrogen and active hydrogen, the nitrogen atom not being part of an isocyanate group
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Polyurethanes Or Polyureas (AREA)
- Paints Or Removers (AREA)
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| EP11160951 | 2011-04-04 | ||
| EP11160951.7 | 2011-04-04 | ||
| PCT/EP2012/055452 WO2012136521A1 (en) | 2011-04-04 | 2012-03-28 | Polyurethane urea dispersions |
Publications (1)
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| CA2839776A1 true CA2839776A1 (en) | 2012-10-11 |
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| CA2839776A Abandoned CA2839776A1 (en) | 2011-04-04 | 2012-03-28 | Polyurethane urea dispersions |
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| EP (1) | EP2694563B1 (enExample) |
| JP (1) | JP6140680B2 (enExample) |
| KR (1) | KR101917899B1 (enExample) |
| CN (1) | CN103703041B (enExample) |
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| ES (1) | ES2564276T3 (enExample) |
| TW (1) | TWI555800B (enExample) |
| WO (1) | WO2012136521A1 (enExample) |
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| GB201402585D0 (en) | 2014-02-14 | 2014-04-02 | Croda Int Plc | Polyurethane dispersions |
| CN104352359B (zh) * | 2014-10-13 | 2017-06-13 | 万华化学集团股份有限公司 | 一种基于水性聚氨酯分散体的可剥离面膜基质 |
| US20170335047A1 (en) | 2014-11-03 | 2017-11-23 | Basf Se | Polyurethane dispersions based on renewable raw materials |
| ES2646564T3 (es) * | 2014-11-17 | 2017-12-14 | Covestro Deutschland Ag | Poliuretanoureas para revestimientos de madera |
| EP3064519B1 (de) * | 2015-03-06 | 2018-12-19 | Covestro Deutschland AG | Wässrige Polyurethanharnstoff-Dispersion, enthaltend freie Säuregruppen |
| RU2746776C2 (ru) * | 2016-07-15 | 2021-04-20 | БАСФ Коатингс ГмбХ | Водное базовое покрытие и получение многослойных красочных систем посредством применения базового покрытия |
| JP7084911B2 (ja) * | 2016-07-28 | 2022-06-15 | コベストロ、ドイチュラント、アクチエンゲゼルシャフト | 低硬度のポリウレタン分散体 |
| EP4122967A1 (en) * | 2016-10-14 | 2023-01-25 | Asahi Kasei Kabushiki Kaisha | Polyisocyanate composition, blocked polyisocyanate composition, hydrophilic polyisocyanate composition, coating material composition, and coating film |
| US20210115278A1 (en) * | 2017-04-26 | 2021-04-22 | Dainichiseika Color & Chemicals Mfg. Co., Ltd. | Bio-based polyurethane resin, bio-based polyurethane resin solution, and printing ink |
| WO2019002263A1 (de) * | 2017-06-26 | 2019-01-03 | Basf Se | Thermoplastisches polyurethan |
| US20190040181A1 (en) * | 2017-08-02 | 2019-02-07 | Covestro Llc | One component polyurethane dispersion for vinyl windows |
| US11059935B2 (en) | 2017-08-02 | 2021-07-13 | Covestro Llc | One component polyurethane dispersion for vinyl windows and other substrates |
| EP3793625A1 (en) | 2018-05-16 | 2021-03-24 | SurModics, Inc. | High-pressure balloon catheters and methods |
| EP3636321A1 (en) * | 2018-10-10 | 2020-04-15 | Covestro Deutschland AG | Polyurethane urea dispersions at least partially originated from renewable sources and their production and uses |
| CN109749042B (zh) * | 2018-12-06 | 2021-03-30 | 杭州传化精细化工有限公司 | 一种磺酸型水性聚氨酯分散体的制备方法 |
| CN109679059B (zh) * | 2018-12-11 | 2021-07-23 | 万华化学集团股份有限公司 | 一种聚氨酯-聚脲水分散体及其制备方法与应用 |
| CN109836551B (zh) * | 2019-01-28 | 2021-12-10 | 上海鸿得聚氨酯有限公司 | 一种聚氨酯运动防护泡沫衬垫组合物及其制备方法 |
| JP7275467B2 (ja) * | 2019-05-28 | 2023-05-18 | 株式会社リコー | インク、インクの製造方法、印刷方法及び印刷装置 |
| FR3109583B1 (fr) * | 2020-04-28 | 2022-07-29 | Arkema France | Dispersion aqueuse de poly(ester-uréthane) ou de poly(ester-urée-uréthane) |
| US11530332B1 (en) * | 2022-07-12 | 2022-12-20 | Evoco Limited | Biobased aqueous polyurethane dispersions |
| CN116239754B (zh) * | 2023-01-03 | 2025-04-01 | 万华化学集团股份有限公司 | 一种聚氨酯或聚氨酯脲水分散体及其制备方法和应用 |
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| DE1495745C3 (de) * | 1963-09-19 | 1978-06-01 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung wäßriger, emulgatorfreier Polyurethan-Latices |
| DE2446440C3 (de) | 1974-09-28 | 1981-04-30 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von wäßrigen Dispersionen von Sulfonatgruppen aufweisenden Polyurethanen |
| DE2651506C2 (de) * | 1976-11-11 | 1986-04-30 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von in Wasser dispergierbaren Polyurethanen |
| JP2503982B2 (ja) * | 1986-07-07 | 1996-06-05 | 大日本インキ化学工業株式会社 | 変性ポリウレタン水分散液の製造方法 |
| DE4300087A1 (de) * | 1993-01-07 | 1994-07-14 | Henkel Kgaa | Blockcopolymere als Schaumregulatoren in Wasch- oder Reinigungsmitteln |
| GB9323603D0 (en) | 1993-11-16 | 1994-01-05 | Baxenden Chem | Low fogging polyester polyurethane foams |
| DE4406159A1 (de) * | 1994-02-25 | 1995-08-31 | Bayer Ag | Wäßrige Polyester-Polyurethan-Dispersionen und ihre Verwendung in Beschichtungsmitteln |
| DE19517185A1 (de) * | 1995-05-11 | 1996-11-14 | Bayer Ag | Biologisch abbaubare und kompostierbare Formkörper einschließlich Flächengebilden |
| US5616400A (en) * | 1995-11-20 | 1997-04-01 | Century International Adhesives & Coating Corporation | Cold seal adhesives, cold sealable films and packages formed therewith |
| KR0173522B1 (ko) * | 1995-12-20 | 1999-04-01 | 최근배 | 폴리우레탄 프리폴리머의 제조방법, 상기 프리폴리머로부터 제조되는 수용성 폴리우레탄 분산체의 제조방법 및 그의 용도 |
| DE19645663A1 (de) * | 1996-11-06 | 1998-05-07 | Bayer Ag | Biologisch abbaubare und kompostierbare Formkörper |
| US6017997A (en) | 1997-10-31 | 2000-01-25 | The B. F. Goodrich Company | Waterborne polyurethane having film properties comparable to rubber |
| DE19750186A1 (de) | 1997-11-13 | 1999-05-20 | Bayer Ag | Hydrophilierungsmittel, ein Verfahren zu dessen Herstellung sowie dessen Verwendung als Dispergator für wäßrige Polyurethan-Dispersionen |
| US6162863A (en) * | 1997-12-04 | 2000-12-19 | Henkel Kommanditgesellschaft Auf Aktien | Waterborne polyurethanes with urea-urethane linkages |
| DE10215474A1 (de) * | 2002-04-09 | 2003-10-23 | Degussa | Flexiblere Polyurethan-Pulverlacke mit mattem Erscheinungsbild |
| JP4180847B2 (ja) * | 2002-06-17 | 2008-11-12 | 大日精化工業株式会社 | 接着剤組成物 |
| DE10257217A1 (de) * | 2002-12-07 | 2004-06-24 | Degussa Ag | Pulverlackzusammensetzungen für Beschichtungen mit mattem Erscheinungsbild |
| JP4703143B2 (ja) * | 2004-07-09 | 2011-06-15 | 日立化成ポリマー株式会社 | 総揮発性有機化合物量の少ないポリエステルポリウレタン成形品の製造方法 |
| DE102004061103A1 (de) * | 2004-12-18 | 2006-06-22 | Bayer Materialscience Ag | Polymerdispersionen in Polyesterpolyolen |
| DE102005040130A1 (de) * | 2005-08-25 | 2007-03-01 | Bayer Materialscience Ag | Polyurethanpolyharnstoff-Dispersionen |
| DE102006054237A1 (de) * | 2006-11-17 | 2008-05-21 | Bayer Materialscience Ag | Polyurethan-modifizierte Alkydharzdispersionen |
| DE102007019184A1 (de) | 2007-04-20 | 2008-10-23 | Organo Balance Gmbh | Mikroorganismus zur Herstellung von Bernsteinsäure |
| EP2015014A1 (de) * | 2007-07-11 | 2009-01-14 | Bayer MaterialScience AG | Verfahren zur Trocknung von Schäumen aus wässrigen PUR-Dispersionen |
| CL2008003124A1 (es) * | 2007-11-07 | 2009-11-27 | Bayer Materialscience Ag | Dispersiones acuosas de poliuretano-urea acuosa de; poliol(es) difuncional (es) o funcionalidad superior, compuestos(s) monofuncional (es) con la menos 50% p/p de óxido de etileno, componente(s)di o poliiocianato; y mezcla de compuestos monoamina primarios y/o secundarios; procedimiento; uso; composición; y compuesto adhesivo. |
| DE102008009517A1 (de) * | 2008-02-15 | 2009-08-20 | Bayer Materialscience Ag | Dispersionsklebstoffe |
| DE102008014211A1 (de) | 2008-03-14 | 2009-09-17 | Bayer Materialscience Ag | Wässrige Dispersion aus anionisch modifizierten Polyurethanharnstoffen zur Beschichtung eines textilen Flächengebildes |
| JP5403478B2 (ja) * | 2008-06-13 | 2014-01-29 | 川崎化成工業株式会社 | ポリウレタンエラストマー |
| DE102008051727A1 (de) | 2008-10-17 | 2010-04-22 | Organo Balance Gmbh | Mikroorganismus zur Herstellung von Bernsteinsäure |
| CN101665675B (zh) * | 2009-09-22 | 2012-03-28 | 烟台华大化学工业有限公司 | 一种水性聚氨酯粘合剂及超细纤维合成革的制备方法 |
| KR20140005283A (ko) * | 2011-03-21 | 2014-01-14 | 바이엘 인텔렉쳐 프로퍼티 게엠베하 | 유기 공-용매가 필요하지 않은 수성 폴리에스테르-폴리우레탄 분산액 |
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Also Published As
| Publication number | Publication date |
|---|---|
| JP6140680B2 (ja) | 2017-05-31 |
| CN103703041B (zh) | 2016-04-13 |
| TWI555800B (zh) | 2016-11-01 |
| US20140249266A1 (en) | 2014-09-04 |
| EP2694563B1 (en) | 2016-01-20 |
| AU2012238859A1 (en) | 2013-10-24 |
| KR20140020987A (ko) | 2014-02-19 |
| ES2564276T3 (es) | 2016-03-21 |
| WO2012136521A1 (en) | 2012-10-11 |
| CN103703041A (zh) | 2014-04-02 |
| TW201302942A (zh) | 2013-01-16 |
| EP2694563A1 (en) | 2014-02-12 |
| KR101917899B1 (ko) | 2018-11-12 |
| JP2014516367A (ja) | 2014-07-10 |
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| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |
Effective date: 20170329 |