EP3818092A1 - Verfahren zur herstellung einer polyurethan-dispersion mit verringerter schaumbildung - Google Patents
Verfahren zur herstellung einer polyurethan-dispersion mit verringerter schaumbildungInfo
- Publication number
- EP3818092A1 EP3818092A1 EP19733815.5A EP19733815A EP3818092A1 EP 3818092 A1 EP3818092 A1 EP 3818092A1 EP 19733815 A EP19733815 A EP 19733815A EP 3818092 A1 EP3818092 A1 EP 3818092A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- isocyanate
- water
- acid
- mass
- alcohol
- 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.)
- Pending
Links
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- 238000004519 manufacturing process Methods 0.000 title claims abstract description 9
- 230000015572 biosynthetic process Effects 0.000 title description 6
- 239000006260 foam Substances 0.000 title description 6
- 239000000203 mixture Substances 0.000 claims abstract description 26
- 150000001875 compounds Chemical class 0.000 claims abstract description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000002904 solvent Substances 0.000 claims abstract description 20
- 238000006243 chemical reaction Methods 0.000 claims abstract description 16
- 239000007791 liquid phase Substances 0.000 claims abstract description 8
- 239000007788 liquid Substances 0.000 claims abstract description 6
- 238000009835 boiling Methods 0.000 claims abstract description 4
- 229920005862 polyol Polymers 0.000 claims description 39
- 150000003077 polyols Chemical class 0.000 claims description 39
- 238000000034 method Methods 0.000 claims description 17
- 239000005056 polyisocyanate Substances 0.000 claims description 12
- 229920001228 polyisocyanate Polymers 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- 125000000129 anionic group Chemical group 0.000 claims description 10
- 229920002635 polyurethane Polymers 0.000 claims description 8
- 239000004814 polyurethane Substances 0.000 claims description 8
- 125000002091 cationic group Chemical group 0.000 claims description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
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- 229920000570 polyether Polymers 0.000 description 22
- 239000004721 Polyphenylene oxide Substances 0.000 description 16
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 14
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 14
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 12
- -1 araliphatic Chemical group 0.000 description 11
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 10
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 9
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 9
- 229940117969 neopentyl glycol Drugs 0.000 description 9
- 229920005906 polyester polyol Polymers 0.000 description 9
- PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 description 8
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 8
- 150000002009 diols Chemical class 0.000 description 8
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 8
- 229920000515 polycarbonate Polymers 0.000 description 8
- 239000004417 polycarbonate Substances 0.000 description 8
- 239000001361 adipic acid Substances 0.000 description 7
- 235000011037 adipic acid Nutrition 0.000 description 7
- 125000001931 aliphatic group Chemical group 0.000 description 7
- 239000006185 dispersion Substances 0.000 description 7
- 238000004821 distillation Methods 0.000 description 7
- 229920000728 polyester Polymers 0.000 description 7
- 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 6
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 6
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 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
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 6
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 5
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 5
- 238000005187 foaming Methods 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 4
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 4
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 4
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 4
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 4
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 4
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 4
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 4
- 235000013772 propylene glycol Nutrition 0.000 description 4
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 4
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 4
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- IBVAQQYNSHJXBV-UHFFFAOYSA-N adipic acid dihydrazide Chemical compound NNC(=O)CCCCC(=O)NN IBVAQQYNSHJXBV-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- XEVRDFDBXJMZFG-UHFFFAOYSA-N carbonyl dihydrazine Chemical compound NNC(=O)NN XEVRDFDBXJMZFG-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 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
- 125000005442 diisocyanate group Chemical group 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 3
- 229920000058 polyacrylate Polymers 0.000 description 3
- 229920001451 polypropylene glycol Polymers 0.000 description 3
- 150000003141 primary amines Chemical class 0.000 description 3
- 235000019260 propionic acid Nutrition 0.000 description 3
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 3
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 3
- VYMPLPIFKRHAAC-UHFFFAOYSA-N 1,2-ethanedithiol Chemical compound SCCS VYMPLPIFKRHAAC-UHFFFAOYSA-N 0.000 description 2
- 229940058015 1,3-butylene glycol Drugs 0.000 description 2
- SRZXCOWFGPICGA-UHFFFAOYSA-N 1,6-Hexanedithiol Chemical compound SCCCCCCS SRZXCOWFGPICGA-UHFFFAOYSA-N 0.000 description 2
- CXUAEBDTJFKMBV-UHFFFAOYSA-N 1-(chloromethyl)-2,3,4,5,6-pentamethylbenzene Chemical compound CC1=C(C)C(C)=C(CCl)C(C)=C1C CXUAEBDTJFKMBV-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
- 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 description 2
- WVQHODUGKTXKQF-UHFFFAOYSA-N 2-ethyl-2-methylhexane-1,1-diol Chemical compound CCCCC(C)(CC)C(O)O WVQHODUGKTXKQF-UHFFFAOYSA-N 0.000 description 2
- GHPVDCPCKSNJDR-UHFFFAOYSA-N 2-hydroxydecanoic acid Chemical compound CCCCCCCCC(O)C(O)=O GHPVDCPCKSNJDR-UHFFFAOYSA-N 0.000 description 2
- WXUAQHNMJWJLTG-UHFFFAOYSA-N 2-methylbutanedioic acid Chemical compound OC(=O)C(C)CC(O)=O WXUAQHNMJWJLTG-UHFFFAOYSA-N 0.000 description 2
- VYZKQGGPNIFCLD-UHFFFAOYSA-N 3,3-dimethylhexane-2,2-diol Chemical compound CCCC(C)(C)C(C)(O)O VYZKQGGPNIFCLD-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- DZIHTWJGPDVSGE-UHFFFAOYSA-N 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1CC1CCC(N)CC1 DZIHTWJGPDVSGE-UHFFFAOYSA-N 0.000 description 2
- CDBAMNGURPMUTG-UHFFFAOYSA-N 4-[2-(4-hydroxycyclohexyl)propan-2-yl]cyclohexan-1-ol Chemical compound C1CC(O)CCC1C(C)(C)C1CCC(O)CC1 CDBAMNGURPMUTG-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
- PJWWRFATQTVXHA-UHFFFAOYSA-N Cyclohexylaminopropanesulfonic acid Chemical compound OS(=O)(=O)CCCNC1CCCCC1 PJWWRFATQTVXHA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
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- 239000005058 Isophorone diisocyanate Substances 0.000 description 2
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- 239000000654 additive Substances 0.000 description 2
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- 125000002947 alkylene group Chemical group 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
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- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- 235000019437 butane-1,3-diol Nutrition 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
- 150000007942 carboxylates Chemical class 0.000 description 2
- PMMYEEVYMWASQN-IMJSIDKUSA-N cis-4-Hydroxy-L-proline Chemical compound O[C@@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-IMJSIDKUSA-N 0.000 description 2
- PDXRQENMIVHKPI-UHFFFAOYSA-N cyclohexane-1,1-diol Chemical compound OC1(O)CCCCC1 PDXRQENMIVHKPI-UHFFFAOYSA-N 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- 239000012975 dibutyltin dilaurate Substances 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
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- 229940028356 diethylene glycol monobutyl ether Drugs 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- SWRGUMCEJHQWEE-UHFFFAOYSA-N ethanedihydrazide Chemical compound NNC(=O)C(=O)NN SWRGUMCEJHQWEE-UHFFFAOYSA-N 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
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- 150000008040 ionic compounds Chemical class 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-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
- 150000002596 lactones Chemical class 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 150000002763 monocarboxylic acids Chemical class 0.000 description 2
- QHJABUZHRJTCAR-UHFFFAOYSA-N n'-methylpropane-1,3-diamine Chemical compound CNCCCN QHJABUZHRJTCAR-UHFFFAOYSA-N 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 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
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920000768 polyamine Polymers 0.000 description 2
- 229920003226 polyurethane urea Polymers 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
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- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical class CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- FHHJDRFHHWUPDG-UHFFFAOYSA-N peroxysulfuric acid Chemical class OOS(O)(=O)=O FHHJDRFHHWUPDG-UHFFFAOYSA-N 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- ZJLMKPKYJBQJNH-UHFFFAOYSA-N propane-1,3-dithiol Chemical compound SCCCS ZJLMKPKYJBQJNH-UHFFFAOYSA-N 0.000 description 1
- ZNZJJSYHZBXQSM-UHFFFAOYSA-N propane-2,2-diamine Chemical compound CC(C)(N)N ZNZJJSYHZBXQSM-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229960003080 taurine Drugs 0.000 description 1
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 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 1
- 238000005829 trimerization reaction Methods 0.000 description 1
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C08G18/48—Polyethers
- C08G18/4833—Polyethers containing oxyethylene units
- C08G18/4837—Polyethers containing oxyethylene units and other oxyalkylene units
- C08G18/485—Polyethers containing oxyethylene units and other oxyalkylene units containing mixed oxyethylene-oxypropylene or oxyethylene-higher oxyalkylene end groups
-
- 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
- C08G18/08—Processes
- C08G18/0838—Manufacture of polymers in the presence of non-reactive compounds
- C08G18/0842—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents
- C08G18/0861—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents in the presence of a dispersing phase for the polymers or a phase dispersed in the polymers
- C08G18/0866—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents in the presence of a dispersing phase for the polymers or a phase dispersed in the polymers the dispersing or dispersed phase being an aqueous medium
-
- 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
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
- C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
-
- 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
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3225—Polyamines
- C08G18/3234—Polyamines cycloaliphatic
-
- 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
- C08G18/4009—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
-
- 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
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4236—Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic groups
- C08G18/4238—Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic groups derived from dicarboxylic acids and dialcohols
-
- 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
- C08G18/75—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
Definitions
- the present invention relates to a method for producing a polyurethane dispersion, comprising the steps: I) providing isocyanate-functional prepolymers A) in a liquid phase comprising a solvent which is miscible with water and which has a lower boiling point than water and II) adding from NCO-reactive compounds to the isocyanate-functional prepolymers from step I), so that a reaction with the prepolymers occurs at least partially; wherein the liquid phase in step I) further comprises water and / or after step II) water is added to the mixture obtained after step II).
- the polymer When producing low-solvent polyurethane dispersions according to the acetone process, the polymer is first dissolved in acetone and is then dispersed in water. The acetone is then removed by distillation in vacuo. This often results in large amounts of foam, which means that the distillation speed must be significantly reduced. This lowers the space-time yield of the system.
- defoamers the chemical basis of which is often hydrophobic mineral oils or silicone oils, can only partially suppress foam formation.
- the presence of defoamers in many products is undesirable. For example, flow problems caused by defoamers can occur in paints.
- DE 27 08 442 A1 relates to a process for the preparation of modified aqueous plastic dispersions, organic diisocyanates which are liquid at room temperature in polyurethane-containing, non-sedimented, aqueous plastic dispersions, optionally with simultaneous presence of the isocyanate polyaddition reactions and / or the dimerization of isocyanate groups and / or the carbodiimidization of isocyanate groups and / or the trimerization of isocyanate group-accelerating catalysts, with mixing at a temperature at which there is no visible foaming, the stated temperature condition is maintained after addition of the diisocyanate until at least 50% of the Isocyanate groups of the diisocyanate introduced have reacted and, if appropriate, the reaction is subsequently brought to an end by heating to temperatures of up to 100 ° C.
- the object of the present invention is to provide a method for producing a polyurethane dispersion in which less foaming occurs during the distillation of organic solvents.
- a method for producing a polyurethane dispersion comprises the steps:
- step II adding NCO-reactive compounds to the isocyanate-functional prepolymers from step I), so that at least partially a reaction with the prepolymers occurs; wherein the liquid phase in step I) further comprises water and / or after step II) water is added to the mixture obtained after step II).
- a pressure pl is applied over the liquid mixture with the isocyanate-functional prepolymers A), pl being less than the local atmospheric pressure at that time and the pressure pl being chosen so that in step II ) ⁇ 50% by mass (preferably> 0% by mass to ⁇ 40% by mass, more preferably> 0.1% by mass to ⁇ 30% by mass, more preferably> 1% by mass to ⁇ 10% by mass) the water-miscible solvent originally present is distilled off.
- foam formation is less when a conventional process is modified so that the chain extension step takes place after a vacuum is applied.
- the majority of the organic solvent does not yet distill off, which can be regulated by suitable values of vacuum and temperature. Due to the reduced tendency to foam, the subsequent distillation can be carried out more quickly, so that the yields of the production plants can be increased.
- the prepolymer A) can have an average NCO functionality of> 1.2 to ⁇ 3.
- the polyisocyanate or the polyisocyanates are used in a stoichiometric excess to produce them, so that the prepolymer has terminal isocyanate groups.
- Particularly suitable solvents for the prepolymer are wholly or partly miscible with water in the temperature range from 20 ° C. to 120 ° C. and are not, or only, are isocyanate groups not very reactive and can optionally be removed by distillation after the dispersion has been prepared.
- solvents it is also possible to use other water-immiscible or poorly miscible solvents which are not or only slightly reactive towards isocyanate groups.
- Solvent mixtures of several solvents which meet the aforementioned conditions are also suitable for the preparation of the dispersions according to the invention.
- Preferred solvents are acetone, butanone, tetrahydrofuran, ethyl acetate, butyl acetate and / or dimethyl carbonate. Acetone is very particularly preferred.
- the isocyanate-functional prepolymers A) are obtainable from the reaction of
- Suitable polyisocyanates Al are aromatic, araliphatic, aliphatic or cycloaliphatic polyisocyanates. Mixtures of such polyisocyanates can also be used.
- Preferred polyisocyanates are selected from the group consisting of butylene diisocyanate, hexamethylene diisocyanate (HDI), 1,5-pentamethylene diisocyanate, isophorone diisocyanate (IPDI), 2,2,4 and / or 2,4,4-trimethylhexamethylene diisocyanate, the isomeric bis (4,4 '- Isocyanatocyclohexyl) methanes or their mixtures of any isomer content, isocyanatomethyl-l, 8-octane diisocyanate, 1,4-cyclohexylene diisocyanate, 1,4-phenylene diisocyanate, 2,4- and / or 2,6-tolylene diisocyanate, 1,5-naphthylene di
- Suitable monomeric polyols A2) are, for example, short-chain, ie containing 2 to 20 carbon atoms, aliphatic, araliphatic or cycloaliphatic polyols.
- diols are ethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, dipropylene glycol, tripropylene glycol, 1,2-propanediol, 1,3-propanediol, 1,4-butanediol, neopentylglycol, 2-ethyl-2-butylpropanediol, trimethylpentanediol, positionally isomeric diethyloctanediole , 1,3-butylene glycol, cyclohexanediol, 1,4-cyclohexanedimethanol, 1,6-hexanediol, 1,2- and 1,4-cyclohexanediol, hydrogenated bis
- triols 1,4- Butanediol, 1,4-cyclohexanedimethanol and 1,6-hexanediol.
- suitable triols are trimethylolethane, trimethylolpropane or glycerol, trimethylolpropane is preferred.
- the polymeric polyols A2) are compounds which in turn are composed of monomers and which, in addition to the mostly terminal isocyanate-reactive end groups, have further functional groups along the main chain.
- Suitable higher molecular weight polyols are polyester polyols, polyacrylate polyols, polyurethane polyols, polycarbonate polyols, polyether polyols, polyester polyacrylate polyols,
- Polyurethane polyacrylate polyols polyurethane polyester polyols, polyurethane polyether polyols, polyurethane polycarbonate polyols and polyester polycarbonate polyols, polyether polyamines and polyamidopolyamines, polyester polyols, polyether polyols and polycarbonate polyols are particularly preferred, and polyester polyols are particularly preferred.
- the suitable polyester polyols are often composed of one or more aliphatic and / or aromatic and / or araliphatic dicarboxylic acids with one or more aliphatic and / or aromatic and / or araliphatic diols and are produced via a polycondensation process.
- polyester polyols are the known polycondensates of di- and, if appropriate, tri, - and tetraoies and di- and, if appropriate, tri- and tetra) carboxylic acids or hydroxycarboxylic acids or lactones.
- the corresponding polycarboxylic acid anhydrides or corresponding polycarboxylic acid esters of lower alcohols can also be used to prepare the polyesters.
- diols examples include ethylene glycol, butylene glycol, diethylene glycol, triethylene glycol, polyalkylene glycols such as polyethylene glycol, also 1,2-propanediol, 1,3-propanediol, butanediol (1,3), butanediol (1,4,), hexanediol (1,6) and isomers, neopentylglycol or hydroxypivalic acid neopenthylglycol esters, the latter three Vcrhi n-dungcii being preferred.
- polyalkylene glycols such as polyethylene glycol, also 1,2-propanediol, 1,3-propanediol, butanediol (1,3), butanediol (1,4,), hexanediol (1,6) and isomers, neopentylglycol or hydroxypivalic acid neopenthylglycol
- polyols with a functionality of 3 can optionally be used, for example trimethylolpropane, glycerol, erythritol, pentaerythritol, triemethylolbenzene or trishydroxyethyl isocyanurate.
- Suitable dicarboxylic acids are phthalic acid, isophthalic acid, terephthalic acid, tetrahydrophthalic acid, hexahydrophthalic acid, cyclohexanedicarboxylic acid, adipic acid, azelaic acid, sebacic acid, glutaric acid, tetrachlorophthalic acid, maleic acid, fumaric acid, itaconic acid, malonic acid, suberic acid, 2-methyl succinic acid, succinic acid, 3,3-diethylglutaric acid, 2,2 -Dimethylsuccinic acid preferred.
- Anhydrides of these acids are also useful if they exist.
- the anhydrides are therefore represented by the term "acid” includes.
- Monocarboxylic acids such as benzoic acid and hexane carboxylic acid are also preferably used, provided that the average functionality of the polyol is 5- 2.
- Saturated aliphatic or aromatic acids are preferred, such as adipic acid or isophthalic acid.
- Trimellitic acid may be mentioned here as a polycarboxylic acid which may also be used in smaller amounts.
- Hydroxycarboxylic acids which are suitable as reactants in the production of a polyester polyol having terminal hydroxyl groups are, for example, hydroxycaproic acid, hydroxybutyric acid, hydroxydecanoic acid, hydroxystearic acid and the like.
- Useful lactones include e-caprolactone, butyrolactone and homologues.
- Polyester polyols based on butanediol and / or neopentyl glycol and / or hexanediol and / or ethylene glycol and / or diethylene glycol with adipic acid and / or phthalic acid and / or isophthalic acid are preferred.
- Polyester polyols based on butanediol and / or neopentyl glycol and / or hexanediol with adipic acid and / or phthalic acid are particularly preferred.
- polyether polyols are the polyadducts of styrene oxides, ethylene oxide, propylene oxide, tetrahydrofuran, butylene oxide, epichlorohydrin, and their mixed addition and graft products, and those obtained by condensation of polyhydric alcohols or mixtures thereof and the polyether polyols obtained by alkoxylation of polyhydric alcohols, amines and amino alcohols ,
- Suitable hydroxy-functional polyethers have OH functionalities from 1.5 to 6.0, preferably 1.8 to 3.0, OH numbers from 50 to 700, preferably from 100 to 600 mg KOH / g solid and molecular weights Mn from 106 to 4 000 g / mol, preferably from 200 to 3500, such as Alkoxylation products of hydroxy-functional starter molecules such as ethylene glycol, propylene glycol, butanediol, hexanediol, trimethylolpropane, glycerol, pentaerythritol, sorbitol or mixtures of these and also other hydroxy-functional compounds with propylene oxide or butylene oxide.
- hydroxy-functional starter molecules such as ethylene glycol, propylene glycol, butanediol, hexanediol, trimethylolpropane, glycerol, pentaerythritol, sorbitol or mixtures of these and also other
- Polypropylene oxide polyols and polytetramethylene oxide polyols with a molecular weight of 300 to 4000 g / mol are preferred.
- the particularly low molecular weight polyether polyols can be water-soluble with correspondingly high OH contents.
- water-insoluble polypropylene oxide polyols and polytetramethylene oxide polyols with a molecular weight of 500-3000 g / mol and mixtures thereof are particularly preferred.
- the polycarbonate polyols in question can be obtained by reacting carbonic acid derivatives, for example diphenyl carbonate, dimethyl carbonate or phosgene, with diols.
- diols are ethylene glycol, 1,2- and 1,3-propanediol, 1,3- and 1,4-butanediol, 1,6-hexanediol, 1,8-octanediol, neopentylglycol, 1,4-bishydroxymethylcyclohexane, 2-methyl-l, 3-propanediol, 2,2,4- Trimethylpentanediol-1,3, dipropylene glycol, polypropylene glycols, dibutylene glycol, polybutylene glycols, bisphenol A, tetrabromobisphenol A, but also lactone-modified diols in question.
- the diol component preferably contains 40 to 100% by weight of 1,6-hexanediol and / or hexanediol derivatives, preferably those which have ether or ester groups in addition to terminal OH groups, for example products which are obtained by reacting 1 mol of hexanediol with at least 1 mol, preferably 1 to 2 mol, of e-caprolactone or by etherification of hexanediol with itself to obtain di- or trihexylene glycol.
- Polyether polycarbonate polyols can also be used.
- Polycarbonate polyols based on dimethyl carbonate and hexanediol and / or butanediol and / or e-caprolactone are preferred. Polycarbonate polyols based on dimethyl carbonate and hexanediol and / or e-caprolactone are very particularly preferred. It is also possible that isocyanate-reactive cationic, potentially cationic, anionic or potentially anionic and / or nonionic hydrophilizing agents A4) are already added in the synthesis of the prepolymers. Details on the hydrophilizing agents A4) are given below in the text.
- isocyanate-reactive compounds A3) having molecular weights of 62 to 399 g / mol are added in step II).
- the degree of chain extension that is the equivalent ratio of NCO-reactive groups of the compounds used for chain extension and chain termination to free NCO groups of the prepolymer, is generally between 40 and 150%, preferably between 50 and 110%, particularly preferably between 60 and 100%.
- amines which have no ionic or ionogenic, such as anionically hydrophilizing groups preference is given to organic di- or polyamines such as, for example, 1,2-ethylenediamine, 1,2- and 1,3-diaminopropane, 1,4-diaminobutane, 1,6-diaminohexane, isophoronediamine, isomer mixture of 2.2, 4- and 2,4,4-trimethylhexamethylene diamine, 2-methylpentamethylene diamine, diethylene triamine, 4,4-diaminodicyclohexyl methane, hydrazine hydrate, and / or dimethylethylene diamine.
- 1,2-ethylenediamine 1,2- and 1,3-diaminopropane
- 1,4-diaminobutane 1,6-diaminohexane
- isophoronediamine isomer mixture of 2.2, 4- and 2,4,4-trimethylhexamethylene diamine, 2-methylpentamethylene di
- component A3 it is also possible to use compounds which, in addition to a primary amino group, also have secondary amino groups or, in addition to an amino group (primary or secondary), also have OH groups.
- primary / secondary amines such as diethanolamine, 3-amino-1-methylaminopropane, 3-amino-1-ethylaminopropane, 3-amino-1-cyclohexylamino propane, 3-amino-1-methylaminobutane, alkanolamines such as N-aminoethyl -ethanolamine, ethanolamine, 3-aminopropanol, neopentanolamine.
- Monofunctional isocyanate-reactive amine compounds can also be used as component A3) be used, such as methylamine, ethylamine, propylamine, butylamine, octylamine, laurylamine, stearylamine, isononyloxypropylamine, dimethylamine, diethylamine, dipropylamine, dibutylamine, N-methylaminopropylamine, diethyl (methyl) aminopropylamine, morpholine, piperidine, or suitable substituted derivatives thereof, Amidamines from diprimary amines and monocarboxylic acids, mono-ketim of diprimary amines, primary / tertiary amines, such as N, N-dimethylaminopropylamine.
- Dihydrazides such as adipic acid dihydrazide, oxalic acid dihydrazide, carbohydrazide and succinic acid dihydrazide are also suitable as component A3).
- Longer-chain, amino-functional compounds such as polyetheramines (“Jeffamines”) as component A3) are also suitable.
- component A3 1,2-ethylenediamine, bis (4-aminocyclohexyl) methane, 1,4-diaminobutane, isophoronediamine, ethanolamine, diethanolamine and diethylenetriamine.
- low molecular weight polyols can also be used.
- Suitable low molecular weight polyols are short chain, i.e. Aliphatic, araliphatic or cycloaliphatic compounds containing 2 to 20 carbon atoms.
- diols examples are ethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, dipropylene glycol, tripropylene glycol, 1,2-propanediol, 1,3-propanediol, 1,4-butanediol, neopentylglycol, 2-ethyl-2-butylpropanediol, trimethylpentanediol, positionally isomeric diethyloctanediole , 1,3-butylene glycol, cyclohexanediol, 1,4-cyclohexanedimethanol, 1,6-hexanediol, 1,2- and 1,4-cyclohexanediol, hydrogenated bisphenol A (2,2-bis (4-hydroxycyclohexyl) propane), 2 , 2-dimethyl-3-hydroxypropionic acid (2,2-dimethyl-3-hydroxypropyl ester).
- 1,4-Butanediol, 1,4-cyclohexanedimethanol and 1,6-hexanediol are preferred.
- suitable triols are trimethylolethane, trimethylolpropane or glycerol, trimethylolpropane is preferred.
- chain extenders A3) are dihydrazides such as oxalic acid dihydrazide, carbohydrazide and adipic acid dihydrazide, carbohydrazide and adipic acid dihydrazide are particularly preferred.
- suitable dithiols are 1,2-ethanedithiol, 1,3-propanedithiol, 1,4-butanedithiol and 1,6-hexanedithiol. 1,2-ethanedithiol and 1,6-hexanedithiol are particularly preferred.
- Diamines are preferably used as low molecular weight compounds A3).
- alcohol-functional compounds are preferably incorporated into the prepolymer via components A2).
- Components with isocyanate-reactive amino groups are preferably reacted in as component A3). If a building block contains both isocyanate-reactive amino groups and alcohol groups, it is preferably installed via component A3).
- step II) isocyanate-reactive cationic, potentially cationic, anionic or potentially anionic and / or nonionic hydrophilizing agents A4) are added.
- the degree of chain extension that is the equivalent ratio of NCO-reactive groups of the compounds used for chain extension and chain termination to free NCO groups of the prepolymer, is generally between 40 and 150%, preferably between 50 and 110%, particularly preferably between 60 and 100%.
- Dispersing compounds are those which contain, for example, sulfonium, ammonium, phosphonium, carboxylate, sulfonate, phosphonate groups or the groups which can be converted into the aforementioned groups by salt formation (potentially ionic groups ) or contain polyether groups and can be incorporated into the macromolecules by existing isocyanate-reactive groups.
- the neutralizing agents necessary for salt formation can be added either stoichiometrically or in deficit in relation to the salt-forming group.
- Organic bases such as tertiary amines or inorganic bases such as alkali metal hydroxides or ammonia are added to produce anionic groups.
- Tertiary amines such as triethylamine, triethanolamine or dimethylethanolamine are preferably used.
- Preferred suitable isocyanate-reactive groups are hydroxyl and amino groups.
- Suitable ionic or potentially ionic compounds are, for example, mono- and dihydroxycarboxylic acids, dihydrohxydicarboxylic acids, mono- and diaminocarboxylic acids, mono- and dihydroxysulfonic acids, mono- and diaminosulfonic acids as well as mono- and dihydroxyphosphonic acids or mono- and diaminophosphonic acids and their salts such as dimethylolpropivalic acid, dimethylolpropionic acid, dimethyl acid propionic acid, dimethylolpropionic acid, dimethyl acid propionic acid, dimethylolpropionic acid, dimethyl acid propionic acid, dimethylolpropionic acid, dimethylolpropionic acid, dimethylolpropionic acid, dimethylolpropionic acid and dimethylolpropionic acid, , N- (2-aminoethyl) alanine, 2- (2-aminoethylamino) ethanesulfonic acid, ethylenediamine
- the salt of cyclohexylaminopropanesulfonic acid (CAPS) from WO-A 01/88006 can also be used as an anionic hydrophilizing agent.
- Preferred ionic or potential ionic compounds are those which have carboxy or carboxylate and / or sulfonate groups and / or ammonium groups.
- Preferred compounds are polyether sulfonate, dimethlyol propionic acid, tartaric acid and Dimethylol butyric acid, particularly preferred are polyether sulfonate and dimethylol propionic acid.
- Suitable nonionic hydrophilizing compounds are e.g. Polyoxyalkylene ethers containing at least one hydroxyl or amino group. These polyethers contain from 30% by weight to 100% by weight of building blocks which are derived from ethylene oxide. Linear polyethers with a functionality between 1 and 3 are possible, but also compounds of the general formula:
- RI and R2 each independently represent a divalent aliphatic, cycloaliphatic or aromatic radical having 1 to 18 carbon atoms, which can be interrupted by oxygen and / or nitrogen atoms, and R3 represents an alkoxy-terminated polyethylene oxide radical.
- Compounds which have a nonionic hydrophilicity are, for example, monovalent polyalkylene oxide polyether alcohols having a statistical average of 5 to 70, preferably 7 to 55, ethylene oxide units per molecule, as are obtainable in a manner known per se by alkoxylation of suitable starter molecules.
- Suitable starter molecules are, for example, saturated monoalcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, sec-butanol, the isomers pentanoie, hexanoie, octanols and nonanols, n-decanol, n-dodecanol, n-tetradecanol, n -Hexadecanol, n-octadecanol, cyclohexanol, the isomeric methylcyclohexanols or hydroxymethylcyclohexane, 3 ethyl-3-hydroxymethyloxetane or tetrahydrofurfuryl alcohol, diethylene glycol monoalkyl ether such as, for example, diethylene glycol monobutyl ether, unsaturated alcohols such as allyl alcohol, phenyl alcohol,
- Alkylene oxides suitable for the alkoxylation reaction are, in particular, ethylene oxide and propylene oxide, which can be used in any order or as a mixture in the alkoxylation reaction can be used.
- the polyalkylene oxide polyether alcohols are either pure polyethylene oxide polyethers or mixed polyalkylene oxide polyethers, the alkylene oxide units of which at least 30 mol%, preferably at least 40 mol%, consist of ethylene oxide units.
- Preferred nonionic compounds are monofunctional mixed polyalkylene oxide polyethers which have at least 40 mol% of ethylene oxide and at most 60 mol% of propylene oxide units.
- Monohydroxy-functional alkoxypolyethylene glycols such as e.g. MPEG 750 (Dow Chemical) and LB 25 (Bayer) and dihydroxy-functional compounds with lateral polyethylene oxide units such as e.g. Ymer N 120 (Perstorp) or Tegomer D 3404.
- a particularly preferred prepolymer is made from a polyester composed of adipic acid, 1,6-hexanediol and neopentyl glycol and hexamethylene diisocyanate.
- the polyester preferably has a molecular weight of 1700 g / mol.
- a particularly preferred chain extension reagent is 2- (2-aminoethylamino) ethanesulfonic acid.
- the molar ratio for the preparation of prepolymer A) from NCO to isocyanate-reactive groups can vary from 1.05 to 4.00, preferably from 1.2 to 3.0, particularly preferably from 1.4 to 2.5.
- the prepolymers are prepared by placing the corresponding polyol or a mixture of different polyols in a reaction vessel and then adding the polyisocyanate or the mixture of polyisocyanates at elevated temperature. If mixtures of polyols and / or polyisocyanates are used, the individual reactants can also be added at different times in order to achieve a targeted structure of the prepolymer.
- the reaction can take place either in the melt or in suitable inert solvents such as acetone or butanone.
- the reaction temperature is between 50 ° C and 130 ° C and the reaction time is 1 h - 24 h.
- the urethanization reaction can be accelerated by using suitable catalysts.
- the catalysts known to the person skilled in the art such as, for. B. triethylamine, l, 4-diazabicyclo- [2,2,2] octane, tin dioctoate, dibutyltin dilaurate or bismuth dioctoate, which are initially introduced or added later. Dibutyltin dilaurate is preferred.
- the reaction is usually complete when the NCO content no longer changes, and the reaction is usually checked by titration.
- low-viscosity prepolymers are generally advantageous; if this has not been done during production, the prepolymer is dissolved in a suitable solvent.
- a suitable solvent Such systems are called low-viscosity prepolymers or prepolymer solutions denotes the viscosity at a shear rate of 40 s-1 ⁇ 104 mPas.
- the prepolymer solution preferably has a solids content of> 40% and acetone is preferred as the solvent.
- a preferred polyurethane dispersion to be prepared by the process according to the invention contains 9 to 60% by weight of a polyisocyanate compound, 35 to 90% by weight of an isocyanate-reactive polyol with a molecular weight> 500 g / mol, 0.5 to 5% by weight of an ionic or potentially ionic hydrophilizing agent and 0.5 to 10 wt .-% of a chain extension amine which has no hydrophilic groups.
- the polyurethane dispersion contains at least one additive selected from the group consisting of 0.1 to 25.0% by weight of a nonionic hydrophilizing agent, 0.1 to 15.0% by weight of a further polyol with one Molar mass ⁇ 500 g / mol and 0.1 to 3.0% by weight of other auxiliaries or additives, in particular emulsifiers, biocides, anti-aging agents.
- step II) comprises adding amino-functional anionic, potentially anionic and / or nonionic hydrophilizing agents to the isocyanate-functional prepolymers from step I).
- a pressure p2 is applied after step II) which is lower than the atmospheric pressure prevailing locally at the time, so that> 95% by mass of the water-miscible solvent originally present is distilled off and an aqueous polyurethane dispersion is obtained becomes.
- the process is carried out in such a way that defoamers are present in the polyurethane dispersion obtained in a proportion of ⁇ 1% by weight, based on the weight of the polyurethane.
- defoamers can be, for example, mineral oils or silicone oils.
- the absence of defoamers is preferred, with technically unavoidable impurities being included in the term “absence”.
- the pressure pl is> 10 mbar to ⁇ 800 mbar.
- Preferred pressures for pI are> 100 mbar to ⁇ 700 mbar, more preferably> 300 mbar to ⁇ 600 mbar.
- the pressure p2 is> 20 mbar to ⁇ 600 mbar.
- Preferred pressures for p2 are> 50 mbar to ⁇ 400 mbar, more preferably> 80 mbar to ⁇ 200 mbar.
- the liquid mixture with the isocyanate-functional prepolymers A) has one before and / or during the implementation of step II) Temperature T from> 10 ° C to ⁇ 70 ° C (preferably> 20 ° C to ⁇ 50 ° C).
- IPDI isophorone diisocyanate
- IPDA isophoronediamine
- Example according to the invention Preparation of a polyurethane-urea dispersion with a strong tendency to foaming when the chain extension step is carried out under vacuum
- IPDA isophoronediamine
- Solids content 30%; Particle size (LKS): 278 nm
- Viscosity ⁇ 50 mPas
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)
Abstract
Description
Claims
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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EP18181427.8A EP3590989A1 (de) | 2018-07-03 | 2018-07-03 | Verfahren zur herstellung einer polyurethan-dispersion mit verringerter schaumbildung |
PCT/EP2019/067657 WO2020007816A1 (de) | 2018-07-03 | 2019-07-02 | Verfahren zur herstellung einer polyurethan-dispersion mit verringerter schaumbildung |
Publications (1)
Publication Number | Publication Date |
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EP3818092A1 true EP3818092A1 (de) | 2021-05-12 |
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EP18181427.8A Ceased EP3590989A1 (de) | 2018-07-03 | 2018-07-03 | Verfahren zur herstellung einer polyurethan-dispersion mit verringerter schaumbildung |
EP19733815.5A Pending EP3818092A1 (de) | 2018-07-03 | 2019-07-02 | Verfahren zur herstellung einer polyurethan-dispersion mit verringerter schaumbildung |
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Application Number | Title | Priority Date | Filing Date |
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EP18181427.8A Ceased EP3590989A1 (de) | 2018-07-03 | 2018-07-03 | Verfahren zur herstellung einer polyurethan-dispersion mit verringerter schaumbildung |
Country Status (4)
Country | Link |
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US (1) | US20210230347A1 (de) |
EP (2) | EP3590989A1 (de) |
CN (1) | CN112513129B (de) |
WO (1) | WO2020007816A1 (de) |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2446440C3 (de) | 1974-09-28 | 1981-04-30 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von wäßrigen Dispersionen von Sulfonatgruppen aufweisenden Polyurethanen |
DE2708442C2 (de) * | 1977-02-26 | 1984-10-25 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von modifizierten wäßrigen Kunststoff-Dispersionen |
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 |
DE10024624A1 (de) | 2000-05-18 | 2001-11-22 | Bayer Ag | Modifizierte Polyisocyanate |
DE10127208A1 (de) * | 2001-06-05 | 2002-12-12 | Basf Ag | Polyurethanispersionen und deren Verwendung |
US9617453B2 (en) * | 2009-12-14 | 2017-04-11 | Air Products And Chemicals, Inc. | Solvent free aqueous polyurethane dispersions and methods of making and using the same |
EP2377895A1 (de) * | 2010-04-14 | 2011-10-19 | Bayer MaterialScience AG | Wässrige Polyurethanpolyharnstoff-Dispersionen |
EP2756020B1 (de) * | 2011-09-13 | 2020-08-19 | Covestro Deutschland AG | Wässrige polyurethandispersion für wasserdichte atmungsaktive beschichtungen |
CN107109113A (zh) * | 2014-08-11 | 2017-08-29 | 路博润先进材料公司 | 用于印刷、数字喷墨油墨和在织物上印刷的含水聚合物组合物 |
-
2018
- 2018-07-03 EP EP18181427.8A patent/EP3590989A1/de not_active Ceased
-
2019
- 2019-07-02 WO PCT/EP2019/067657 patent/WO2020007816A1/de unknown
- 2019-07-02 EP EP19733815.5A patent/EP3818092A1/de active Pending
- 2019-07-02 US US16/972,125 patent/US20210230347A1/en not_active Abandoned
- 2019-07-02 CN CN201980044380.XA patent/CN112513129B/zh active Active
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EP3590989A1 (de) | 2020-01-08 |
CN112513129A (zh) | 2021-03-16 |
US20210230347A1 (en) | 2021-07-29 |
WO2020007816A1 (de) | 2020-01-09 |
CN112513129B (zh) | 2022-12-27 |
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