JP2011523672A - ポリカーボネートポリオールに基づくポリウレタン−ポリウレア分散体 - Google Patents
ポリカーボネートポリオールに基づくポリウレタン−ポリウレア分散体 Download PDFInfo
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- JP2011523672A JP2011523672A JP2011511632A JP2011511632A JP2011523672A JP 2011523672 A JP2011523672 A JP 2011523672A JP 2011511632 A JP2011511632 A JP 2011511632A JP 2011511632 A JP2011511632 A JP 2011511632A JP 2011523672 A JP2011523672 A JP 2011523672A
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- Prior art keywords
- isocyanate
- group
- polyurethane
- compounds
- dispersion
- 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.)
- Granted
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- 239000006185 dispersion Substances 0.000 title claims abstract description 55
- 229920005862 polyol Polymers 0.000 title claims abstract description 19
- 229920002396 Polyurea Polymers 0.000 title claims abstract description 16
- 239000004417 polycarbonate Substances 0.000 title claims description 15
- 229920000515 polycarbonate Polymers 0.000 title claims description 15
- 150000003077 polyols Chemical class 0.000 title claims description 15
- 238000000576 coating method Methods 0.000 claims abstract description 17
- 239000011248 coating agent Substances 0.000 claims abstract description 11
- 239000000463 material Substances 0.000 claims abstract description 11
- 238000004519 manufacturing process Methods 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 26
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 18
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 15
- 239000005056 polyisocyanate Substances 0.000 claims description 14
- 229920001228 polyisocyanate Polymers 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- -1 polytetramethylene Polymers 0.000 claims description 13
- 239000000758 substrate Substances 0.000 claims description 12
- 125000003277 amino group Chemical group 0.000 claims description 11
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 11
- 150000002433 hydrophilic molecules Chemical class 0.000 claims description 7
- 239000010985 leather Substances 0.000 claims description 7
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 5
- 239000004753 textile Substances 0.000 claims description 5
- 239000012948 isocyanate Substances 0.000 claims description 4
- 150000002513 isocyanates Chemical class 0.000 claims description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical group NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 3
- 239000004202 carbamide Substances 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- 239000004814 polyurethane Substances 0.000 description 22
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 239000002904 solvent Substances 0.000 description 11
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 8
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 8
- 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 7
- 150000002009 diols Chemical class 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 5
- 230000014759 maintenance of location Effects 0.000 description 5
- 229920000570 polyether Polymers 0.000 description 5
- 229920001730 Moisture cure polyurethane Polymers 0.000 description 4
- 239000004721 Polyphenylene oxide Substances 0.000 description 4
- 125000000129 anionic group Chemical class 0.000 description 4
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 4
- 230000003301 hydrolyzing effect Effects 0.000 description 4
- 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 4
- 229920002635 polyurethane Polymers 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 239000005058 Isophorone diisocyanate Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 238000006243 chemical reaction Methods 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
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 3
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 3
- 230000003472 neutralizing effect Effects 0.000 description 3
- 229920003009 polyurethane dispersion Polymers 0.000 description 3
- 150000003141 primary amines Chemical class 0.000 description 3
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 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
- 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
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 description 2
- NNLRDVBAHRQMHK-UHFFFAOYSA-N 3-(2-aminoethylamino)propanoic acid Chemical compound NCCNCCC(O)=O NNLRDVBAHRQMHK-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 229920000049 Carbon (fiber) Polymers 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
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-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
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 239000004917 carbon fiber Substances 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- 125000005442 diisocyanate group Chemical group 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000003365 glass fiber Substances 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- 150000008040 ionic compounds Chemical class 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- QHJABUZHRJTCAR-UHFFFAOYSA-N n'-methylpropane-1,3-diamine Chemical compound CNCCCN QHJABUZHRJTCAR-UHFFFAOYSA-N 0.000 description 2
- GNVRJGIVDSQCOP-UHFFFAOYSA-N n-ethyl-n-methylethanamine Chemical compound CCN(C)CC GNVRJGIVDSQCOP-UHFFFAOYSA-N 0.000 description 2
- ISRXMEYARGEVIU-UHFFFAOYSA-N n-methyl-n-propan-2-ylpropan-2-amine Chemical compound CC(C)N(C)C(C)C ISRXMEYARGEVIU-UHFFFAOYSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 2
- 125000005270 trialkylamine group Chemical group 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
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- 239000002759 woven fabric Substances 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
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
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- 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
- ZWVMLYRJXORSEP-UHFFFAOYSA-N 1,2,6-Hexanetriol Chemical compound OCCCCC(O)CO ZWVMLYRJXORSEP-UHFFFAOYSA-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
- RTTZISZSHSCFRH-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC(CN=C=O)=C1 RTTZISZSHSCFRH-UHFFFAOYSA-N 0.000 description 1
- 229940058015 1,3-butylene glycol Drugs 0.000 description 1
- AGJCSCSSMFRMFQ-UHFFFAOYSA-N 1,4-bis(2-isocyanatopropan-2-yl)benzene Chemical compound O=C=NC(C)(C)C1=CC=C(C(C)(C)N=C=O)C=C1 AGJCSCSSMFRMFQ-UHFFFAOYSA-N 0.000 description 1
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 description 1
- 150000000190 1,4-diols Chemical class 0.000 description 1
- HKKRLTYNFQKROE-UHFFFAOYSA-N 1-hydroxybutyl 6-hydroxyhexanoate Chemical compound CCCC(O)OC(=O)CCCCCO HKKRLTYNFQKROE-UHFFFAOYSA-N 0.000 description 1
- ZOKREBLWJYZZLL-UHFFFAOYSA-N 1-n-methylbutane-1,3-diamine Chemical compound CNCCC(C)N ZOKREBLWJYZZLL-UHFFFAOYSA-N 0.000 description 1
- JVYDLYGCSIHCMR-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)butanoic acid Chemical compound CCC(CO)(CO)C(O)=O JVYDLYGCSIHCMR-UHFFFAOYSA-N 0.000 description 1
- DPQHRXRAZHNGRU-UHFFFAOYSA-N 2,4,4-trimethylhexane-1,6-diamine Chemical compound NCC(C)CC(C)(C)CCN DPQHRXRAZHNGRU-UHFFFAOYSA-N 0.000 description 1
- IVGRSQBDVIJNDA-UHFFFAOYSA-N 2-(2-aminoethylamino)ethanesulfonic acid Chemical compound NCCNCCS(O)(=O)=O IVGRSQBDVIJNDA-UHFFFAOYSA-N 0.000 description 1
- CTNICFBTUIFPOE-UHFFFAOYSA-N 2-(4-hydroxyphenoxy)ethane-1,1-diol Chemical compound OC(O)COC1=CC=C(O)C=C1 CTNICFBTUIFPOE-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- JZUHIOJYCPIVLQ-UHFFFAOYSA-N 2-methylpentane-1,5-diamine Chemical compound NCC(C)CCCN JZUHIOJYCPIVLQ-UHFFFAOYSA-N 0.000 description 1
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- UENRXLSRMCSUSN-UHFFFAOYSA-N 3,5-diaminobenzoic acid Chemical compound NC1=CC(N)=CC(C(O)=O)=C1 UENRXLSRMCSUSN-UHFFFAOYSA-N 0.000 description 1
- HYEOYFUOERFWIX-UHFFFAOYSA-N 3-(7-methyloctoxy)propan-1-amine Chemical compound CC(C)CCCCCCOCCCN HYEOYFUOERFWIX-UHFFFAOYSA-N 0.000 description 1
- FNVOFDGAASRDQY-UHFFFAOYSA-N 3-amino-2,2-dimethylpropan-1-ol Chemical compound NCC(C)(C)CO FNVOFDGAASRDQY-UHFFFAOYSA-N 0.000 description 1
- UDZFEGOYTOHDHK-UHFFFAOYSA-N 3-ethyl-1-N-methylpentane-1,3-diamine Chemical compound CCC(N)(CC)CCNC UDZFEGOYTOHDHK-UHFFFAOYSA-N 0.000 description 1
- RDFQSFOGKVZWKF-UHFFFAOYSA-N 3-hydroxy-2,2-dimethylpropanoic acid Chemical compound OCC(C)(C)C(O)=O RDFQSFOGKVZWKF-UHFFFAOYSA-N 0.000 description 1
- CCTFMNIEFHGTDU-UHFFFAOYSA-N 3-methoxypropyl acetate Chemical compound COCCCOC(C)=O CCTFMNIEFHGTDU-UHFFFAOYSA-N 0.000 description 1
- NXQWWXHHRBLONY-UHFFFAOYSA-N 4-(isocyanatomethyl)octane Chemical compound CCCCC(CCC)CN=C=O NXQWWXHHRBLONY-UHFFFAOYSA-N 0.000 description 1
- DZIHTWJGPDVSGE-UHFFFAOYSA-N 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1CC1CCC(N)CC1 DZIHTWJGPDVSGE-UHFFFAOYSA-N 0.000 description 1
- 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 1
- PJMDLNIAGSYXLA-UHFFFAOYSA-N 6-iminooxadiazine-4,5-dione Chemical compound N=C1ON=NC(=O)C1=O PJMDLNIAGSYXLA-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- ZHESOIPTRUDICE-UHFFFAOYSA-N CCCCCCCCC.N=C=O.N=C=O.N=C=O Chemical compound CCCCCCCCC.N=C=O.N=C=O.N=C=O ZHESOIPTRUDICE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004970 Chain extender Substances 0.000 description 1
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Classifications
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- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
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- C08J3/03—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in aqueous media
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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
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- C08G18/0828—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups containing sulfonate groups or groups forming them
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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
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- 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
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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
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- C08G18/2805—Compounds having only one group containing active hydrogen
- C08G18/2815—Monohydroxy compounds
- C08G18/283—Compounds containing ether groups, e.g. oxyalkylated monohydroxy compounds
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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
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- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/44—Polycarbonates
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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
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- C08G18/722—Combination of two or more aliphatic and/or cycloaliphatic polyisocyanates
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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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Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
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Abstract
Description
I.1)1以上のポリイソシアネート、
I.2)1000〜3000g/molの数平均分子量を有し、18〜56mgKOH/gのヒドロキシル価および1.8〜2.2のOH官能価を有する1以上のポリカーボネートポリオール、
I.3)62〜400g/molの分子量を有し、合計2以上のヒドロキシル基および/またはアミノ基を有する1以上の化合物、
I.4)必要に応じて、ヒドロキシル基またはアミノ基を有する1以上の化合物、
I.5)1以上のイソシアネート反応性のイオン的または潜在的イオン的に親水性化する化合物、および
I.6)必要に応じて、1以上のイソシアネート反応性の非イオン的に親水性化する化合物
を含み、ポリオール成分I.2)が、成分I.2)の合計重量を基準として60重量%〜100重量%のポリテトラメチレングリコール系ポリカーボネートポリオールを含有し、但し、該ポリカーボネートポリオールは、ポリテトラメチレングリコールポリオールに基づかない、ポリウレタン−ポリウレア水性分散体を提供する。
I.1)1以上のポリイソシアネート、
I.2)1000〜3000g/molの数平均分子量を有し、18〜56mgKOH/gのヒドロキシル価および1.8〜2.2のOH官能価を有する1以上のポリカーボネートポリオール、
I.3)62〜400g/molの分子量を有し、合計2以上のヒドロキシル基および/またはアミノ基を有する1以上の化合物、
I.4)必要に応じて、ヒドロキシル基またはアミノ基を有する1以上の化合物、
I.5)1以上のイソシアネート反応性のイオン的または潜在的イオン的に親水性化する化合物、
I.6)必要に応じて、1以上のイソシアネート反応性の非イオン的に親水性化する化合物
を反応させて、ウレア基不含イソシアネート官能性プレポリマーを調製する工程であって、イソシアネート反応性基に対するイソシアネート基のモル比が1.0〜3.5である工程、
b)該反応生成物を水中に分散する工程、および
c)水中での分散前、分散中または分散後に、残存するイソシアネート基をアミノ官能性鎖延長または連鎖停止する工程であって、前記プレポリマーの遊離イソシアネート基に対する鎖延長のために用いる化合物のイソシアネート反応性基の当量比が40%〜150%の間である工程
を含む、本発明のポリウレタンポリウレア水性分散体の製造方法を提供する。
H−Y’−X−Y−R (I)
〔式中、
Rは、1〜12個の炭素原子を有する1価炭化水素基、好ましくは1〜4個の炭素原子を有する未置換アルキル基であり、
Xは、少なくとも40%、好ましくは少なくとも65%の程度のエチレンオキシド単位に構成され得、およびエチレンオキシド単位に加えてプロピレンオキシド、ブチレンオキシドまたはスチレンオキシド単位から構成され得る(後述の単位は、好ましくはプロピレンオキシド単位である)、5〜90個、好ましくは20〜70個の鎖構成要素(chain members)を有するポリアルキレンオキシドであり、および
Y/Y’は、酸素であるか、または−NR’−であり、R’は、定義においてRまたは水素に相当する〕
で示される化合物である。
279.2gのDesmophen C−2200および14.9gのPolyether LB 25の混合物を、35.6gのDesmodur Iおよび26.9gのDesmodur Hと70℃で組み合わせ、105℃に加熱し、4.13%の一定のNCO値(理論値が4.18%である)が得られるまで105℃で撹拌した。該プレポリマーを631.7gのアセトンにより105℃で溶解し、20分間撹拌した。1.1gのヒドラジン水和物、6.8gのジアミノスルホネートおよび25gの水の混合物を42℃で6分間にわたり添加し、10分間撹拌した。12.7gのIPDAおよび63.6gの水の混合物を40℃で15分以内に添加し、10分間撹拌した。278.6gの水を40℃で15分以内に添加し、5分間、2.8gのIrganox 1010および2.8gのTinuvin 765の添加前に混合した。該混合物を10分間、アセトンを蒸留する前に混合した。最終分散体を50ミクロンフィルターによりろ過した。
Impranil DLU(Bayer AG、レーバークーゼン)のような、固形分60%および以下の物理特性を有するアニオン性脂肪族C4ポリエーテルポリカーボネートポリウレタン分散体:100%での弾性率=350psi、引張強度=3500psi、23℃での粘度(AFAM 2008/105、0304−00 D法に従う4mmカップ)<90秒。
Impranil DLN(Bayer AG、レーバークーゼン)のような、固形分40%および以下の物理特性を有するアニオン性脂肪族ポリエステルポリウレタン分散体:100%での弾性率=300psi、引張強度=2900psi、23℃での粘度(AFAM 2008/105、0304−00 D法に従う4mmカップ)<70秒。
上記の表に示された結果に基づいて、100%ポリカーボネートに基づく分散体は、市販の分散体、例えばImpranil DLUおよびImpranil DLN等よりも向上した加水分解安定性および保色性(ナイロン型編織布について)を示すと言うことができる。Impranil DLUは、C4ポリエーテルポリカーボネートジオールを用いて調製され、非常に良好な加水分解安定性を示すが、ナイロン型編織布についての保色性が低い。Impranil DLNは、ポリエステルジオールを用いて調製され、低い加水分解安定性および低い保色性を有する。
Claims (7)
- 以下の合成成分:
I.1)1以上のポリイソシアネート、
I.2)1000〜3000g/molの数平均分子量を有し、18〜56mgKOH/gのヒドロキシル価および1.8〜2.2のOH官能価を有する1以上のポリカーボネートポリオール、
I.3)62〜400g/molの分子量を有し、合計2以上のヒドロキシル基および/またはアミノ基を有する1以上の化合物、
I.4)必要に応じて、ヒドロキシル基またはアミノ基を有する1以上の化合物、
I.5)1以上のイソシアネート反応性のイオン的または潜在的イオン的に親水性化する化合物、および
I.6)必要に応じて、1以上のイソシアネート反応性の非イオン的に親水性化する化合物
を含むポリウレタン−ポリウレア水性分散体であって、該分散体は、前記合成成分の合計重量を基準として60重量%〜90重量%の成分I.2)を含有し、但し、前記ポリカーボネートポリオールは、ポリテトラメチレングリコールポリオールに基づかない、ポリウレタン−ポリウレア水性分散体。 - 成分I.1)5重量%〜40重量%、成分I.2)の合計60重量%〜90重量%、化合物I.3)およびI.4)の合計0.5重量%〜20重量%、成分I.5)0.1重量%〜5重量および成分I.6)0重量%〜20重量%を含み、I.5)およびI.6)の合計が0.1重量%〜25重量%の間であり、全ての成分の合計が100重量%となる、請求項1に記載のポリウレタン−ポリウレア水性分散体。
- I.1)1以上のポリイソシアネート、
I.2)1000〜3000g/molの数平均分子量を有し、18〜56mgKOH/gのヒドロキシル価および1.8〜2.2のOH官能価を有する1以上のポリカーボネートポリオール、
I.3)62〜400g/molの分子量を有し、合計2以上のヒドロキシル基および/またはアミノ基を有する1以上の化合物、
I.4)必要に応じて、ヒドロキシル基またはアミノ基を有する1以上の化合物、
I.5)1以上のイソシアネート反応性のイオン的または潜在的イオン的に親水性化する化合物、
I.6)必要に応じて、1以上のイソシアネート反応性の非イオン的に親水性化する化合物
を反応させて、ウレア基不含イソシアネート官能性プレポリマーを調製する工程であって、イソシアネート反応性基に対するイソシアネート基のモル比が1.0〜3.5である工程、
b)該反応生成物を水中に分散する工程、および
c)水中での分散前、分散中または分散後に、残存するイソシアネート基をアミノ官能性鎖延長または連鎖停止する工程であって、前記プレポリマーの遊離イソシアネート基に対する鎖延長のために用いる化合物のイソシアネート反応性基の当量比が、40%〜150%の間である工程
を含む、請求項1に記載のポリウレタン−ポリウレア水性分散体の製造方法。 - 請求項1に記載のポリウレタン−ポリウレア分散体を含む被覆材料。
- 請求項4に記載の被覆材料を基材に塗布する工程を含む、被覆基材の製造方法。
- 基材は、繊維製品および皮革からなる群から選択される、請求項5に記載の方法。
- 請求項4に記載の被覆材料で被覆された基材。
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WO2012069414A1 (en) * | 2010-11-25 | 2012-05-31 | Bayer Materialscience Ag | Polyurethane resin with high carbonate group content |
PT3164437T (pt) * | 2014-07-02 | 2020-12-04 | Akzo Nobel Coatings Int Bv | Composições de revestimento de dois componentes e revestimentos fabricados à partir das mesmas para a melhoria da resistência à erosão |
CN104327696A (zh) * | 2014-10-21 | 2015-02-04 | 上海东方雨虹防水技术有限责任公司 | 一种聚碳酸酯多元醇型喷涂聚脲弹性体涂料及制备方法 |
EP3239202B1 (en) * | 2014-12-26 | 2022-08-31 | Asahi Kasei Kabushiki Kaisha | Polyisocyanate composition and method for producing the same, blocked polyisocyanate composition and method for producing the same, resin composition and hardened material |
EP3825338A1 (en) | 2019-11-20 | 2021-05-26 | Covestro Intellectual Property GmbH & Co. KG | Polyurethane-urea dispersions based on polycarbonate-polyols as coating compositions |
CN113773732B (zh) * | 2021-09-10 | 2022-05-17 | 苏州己申隆新材料科技有限公司 | 一种风电叶片用防覆冰超滑聚脲涂层及其制备方法和应用 |
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