JPH1192654A - Aqueous polyurethane resin composition - Google Patents
Aqueous polyurethane resin compositionInfo
- Publication number
- JPH1192654A JPH1192654A JP9257231A JP25723197A JPH1192654A JP H1192654 A JPH1192654 A JP H1192654A JP 9257231 A JP9257231 A JP 9257231A JP 25723197 A JP25723197 A JP 25723197A JP H1192654 A JPH1192654 A JP H1192654A
- Authority
- JP
- Japan
- Prior art keywords
- polyurethane resin
- polyol
- aqueous polyurethane
- resin composition
- acid
- 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
Links
- 229920005749 polyurethane resin Polymers 0.000 title claims abstract description 58
- 239000011342 resin composition Substances 0.000 title claims description 20
- 229920005862 polyol Polymers 0.000 claims abstract description 52
- 150000003077 polyols Chemical class 0.000 claims abstract description 52
- -1 ether ester compound Chemical class 0.000 claims abstract description 37
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 19
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 17
- 125000003118 aryl group Chemical group 0.000 claims abstract description 15
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 9
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 8
- 239000007787 solid Substances 0.000 claims abstract description 8
- 230000003472 neutralizing effect Effects 0.000 claims abstract description 6
- 229920005989 resin Polymers 0.000 claims abstract description 4
- 239000011347 resin Substances 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 11
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 26
- 239000006185 dispersion Substances 0.000 abstract description 13
- 238000003860 storage Methods 0.000 abstract description 11
- 239000004753 textile Substances 0.000 abstract description 9
- 230000000704 physical effect Effects 0.000 abstract description 8
- 239000000203 mixture Substances 0.000 abstract description 5
- 229920005906 polyester polyol Polymers 0.000 abstract description 5
- 125000000217 alkyl group Chemical group 0.000 abstract description 3
- 125000002947 alkylene group Chemical group 0.000 abstract description 3
- 239000000463 material Substances 0.000 abstract description 3
- 125000000732 arylene group Chemical group 0.000 abstract description 2
- 230000001877 deodorizing effect Effects 0.000 abstract description 2
- 238000013329 compounding Methods 0.000 abstract 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- 239000000047 product Substances 0.000 description 13
- 239000000835 fiber Substances 0.000 description 11
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 9
- 239000004014 plasticizer Substances 0.000 description 9
- 239000004094 surface-active agent Substances 0.000 description 9
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 8
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical class CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 7
- 239000004721 Polyphenylene oxide Substances 0.000 description 6
- 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 6
- 238000000576 coating method Methods 0.000 description 6
- 235000014113 dietary fatty acids Nutrition 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000000194 fatty acid Substances 0.000 description 6
- 229930195729 fatty acid Natural products 0.000 description 6
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-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
- 229920000570 polyether Polymers 0.000 description 6
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 4
- PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 description 4
- 239000004970 Chain extender Substances 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 239000001361 adipic acid Substances 0.000 description 4
- 235000011037 adipic acid Nutrition 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 239000005058 Isophorone diisocyanate Substances 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 3
- 230000002411 adverse Effects 0.000 description 3
- 125000000129 anionic group Chemical group 0.000 description 3
- 230000000844 anti-bacterial effect Effects 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 125000002091 cationic group Chemical group 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 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 3
- 239000003973 paint Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229960004418 trolamine Drugs 0.000 description 3
- 229940058015 1,3-butylene glycol Drugs 0.000 description 2
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 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
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- 150000005215 alkyl ethers Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 2
- 239000003945 anionic surfactant Substances 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 2
- BMRWNKZVCUKKSR-UHFFFAOYSA-N butane-1,2-diol Chemical compound CCC(O)CO BMRWNKZVCUKKSR-UHFFFAOYSA-N 0.000 description 2
- 235000019437 butane-1,3-diol Nutrition 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
- 239000003093 cationic surfactant Substances 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 239000002781 deodorant agent Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- CKFGINPQOCXMAZ-UHFFFAOYSA-N methanediol Chemical compound OCO CKFGINPQOCXMAZ-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 239000002736 nonionic surfactant Substances 0.000 description 2
- 239000003960 organic solvent Substances 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
- 229920000573 polyethylene Polymers 0.000 description 2
- 229920000193 polymethacrylate Polymers 0.000 description 2
- 150000007519 polyprotic acids Polymers 0.000 description 2
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 229920002994 synthetic fiber Polymers 0.000 description 2
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- ICLYJLBTOGPLMC-KVVVOXFISA-N (z)-octadec-9-enoate;tris(2-hydroxyethyl)azanium Chemical compound OCCN(CCO)CCO.CCCCCCCC\C=C/CCCCCCCC(O)=O ICLYJLBTOGPLMC-KVVVOXFISA-N 0.000 description 1
- NNOZGCICXAYKLW-UHFFFAOYSA-N 1,2-bis(2-isocyanatopropan-2-yl)benzene Chemical compound O=C=NC(C)(C)C1=CC=CC=C1C(C)(C)N=C=O NNOZGCICXAYKLW-UHFFFAOYSA-N 0.000 description 1
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 1
- MTZUIIAIAKMWLI-UHFFFAOYSA-N 1,2-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC=C1N=C=O MTZUIIAIAKMWLI-UHFFFAOYSA-N 0.000 description 1
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 description 1
- CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-UHFFFAOYSA-N 0.000 description 1
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 1
- XDRLAGOBLZATBG-UHFFFAOYSA-N 1-phenylpenta-1,4-dien-3-one Chemical compound C=CC(=O)C=CC1=CC=CC=C1 XDRLAGOBLZATBG-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
- UHAMPPWFPNXLIU-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)pentanoic acid Chemical compound CCCC(CO)(CO)C(O)=O UHAMPPWFPNXLIU-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- GVNHOISKXMSMPX-UHFFFAOYSA-N 2-[butyl(2-hydroxyethyl)amino]ethanol Chemical compound CCCCN(CCO)CCO GVNHOISKXMSMPX-UHFFFAOYSA-N 0.000 description 1
- JOMNTHCQHJPVAZ-UHFFFAOYSA-N 2-methylpiperazine Chemical compound CC1CNCCN1 JOMNTHCQHJPVAZ-UHFFFAOYSA-N 0.000 description 1
- QZWKEPYTBWZJJA-UHFFFAOYSA-N 3,3'-Dimethoxybenzidine-4,4'-diisocyanate Chemical compound C1=C(N=C=O)C(OC)=CC(C=2C=C(OC)C(N=C=O)=CC=2)=C1 QZWKEPYTBWZJJA-UHFFFAOYSA-N 0.000 description 1
- 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 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- JVERADGGGBYHNP-UHFFFAOYSA-N 5-phenylbenzene-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)C(C(=O)O)=CC(C=2C=CC=CC=2)=C1C(O)=O JVERADGGGBYHNP-UHFFFAOYSA-N 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 1
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 1
- 229920000049 Carbon (fiber) Polymers 0.000 description 1
- 239000004803 Di-2ethylhexylphthalate Substances 0.000 description 1
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 229920001214 Polysorbate 60 Polymers 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 239000002174 Styrene-butadiene Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical compound OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 1
- SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical compound CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- GKXVJHDEWHKBFH-UHFFFAOYSA-N [2-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC=C1CN GKXVJHDEWHKBFH-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- IBVAQQYNSHJXBV-UHFFFAOYSA-N adipic acid dihydrazide Chemical compound NNC(=O)CCCCC(=O)NN IBVAQQYNSHJXBV-UHFFFAOYSA-N 0.000 description 1
- 238000007754 air knife coating Methods 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910052936 alkali metal sulfate Inorganic materials 0.000 description 1
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- BTBJBAZGXNKLQC-UHFFFAOYSA-N ammonium lauryl sulfate Chemical compound [NH4+].CCCCCCCCCCCCOS([O-])(=O)=O BTBJBAZGXNKLQC-UHFFFAOYSA-N 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000002280 amphoteric surfactant Substances 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- WPKYZIPODULRBM-UHFFFAOYSA-N azane;prop-2-enoic acid Chemical compound N.OC(=O)C=C WPKYZIPODULRBM-UHFFFAOYSA-N 0.000 description 1
- 238000007611 bar coating method Methods 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- IKWQWOFXRCUIFT-UHFFFAOYSA-N benzene-1,2-dicarbohydrazide Chemical compound NNC(=O)C1=CC=CC=C1C(=O)NN IKWQWOFXRCUIFT-UHFFFAOYSA-N 0.000 description 1
- ZFMQKOWCDKKBIF-UHFFFAOYSA-N bis(3,5-difluorophenyl)phosphane Chemical compound FC1=CC(F)=CC(PC=2C=C(F)C=C(F)C=2)=C1 ZFMQKOWCDKKBIF-UHFFFAOYSA-N 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 235000010338 boric acid Nutrition 0.000 description 1
- DQXBYHZEEUGOBF-UHFFFAOYSA-N but-3-enoic acid;ethene Chemical compound C=C.OC(=O)CC=C DQXBYHZEEUGOBF-UHFFFAOYSA-N 0.000 description 1
- NTXGQCSETZTARF-UHFFFAOYSA-N buta-1,3-diene;prop-2-enenitrile Chemical compound C=CC=C.C=CC#N NTXGQCSETZTARF-UHFFFAOYSA-N 0.000 description 1
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 1
- HCOMFAYPHBFMKU-UHFFFAOYSA-N butanedihydrazide Chemical compound NNC(=O)CCC(=O)NN HCOMFAYPHBFMKU-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000009120 camo Nutrition 0.000 description 1
- 239000004917 carbon fiber Substances 0.000 description 1
- 235000005607 chanvre indien Nutrition 0.000 description 1
- 239000008119 colloidal silica Substances 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 229940125773 compound 10 Drugs 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 150000003983 crown ethers Chemical class 0.000 description 1
- OYOFUEDXAMRQBB-UHFFFAOYSA-N cyclohexylmethanediamine Chemical compound NC(N)C1CCCCC1 OYOFUEDXAMRQBB-UHFFFAOYSA-N 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical compound C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-UHFFFAOYSA-N 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000007606 doctor blade method Methods 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000005108 dry cleaning Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- QTBWAKWPKYZSRL-UHFFFAOYSA-N ethenol;phenol Chemical group OC=C.OC1=CC=CC=C1 QTBWAKWPKYZSRL-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000005038 ethylene vinyl acetate Substances 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 235000019256 formaldehyde Nutrition 0.000 description 1
- NVVZQXQBYZPMLJ-UHFFFAOYSA-N formaldehyde;naphthalene-1-sulfonic acid Chemical compound O=C.C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 NVVZQXQBYZPMLJ-UHFFFAOYSA-N 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 238000007756 gravure coating Methods 0.000 description 1
- 239000011487 hemp Substances 0.000 description 1
- NKUJQQWJJANFIN-UHFFFAOYSA-N hepta-1,4,6-trien-3-one Chemical compound C=CC=CC(=O)C=C NKUJQQWJJANFIN-UHFFFAOYSA-N 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000007602 hot air drying Methods 0.000 description 1
- 235000011167 hydrochloric acid Nutrition 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000012784 inorganic fiber Substances 0.000 description 1
- 229920000554 ionomer Polymers 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000002960 margaryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000006353 oxyethylene group Chemical group 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 239000002530 phenolic antioxidant Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical compound OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920001610 polycaprolactone Polymers 0.000 description 1
- 239000004632 polycaprolactone Substances 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920003225 polyurethane elastomer Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- ONQDVAFWWYYXHM-UHFFFAOYSA-M potassium lauryl sulfate Chemical compound [K+].CCCCCCCCCCCCOS([O-])(=O)=O ONQDVAFWWYYXHM-UHFFFAOYSA-M 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 238000007763 reverse roll coating Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 229940077386 sodium benzenesulfonate Drugs 0.000 description 1
- BTURAGWYSMTVOW-UHFFFAOYSA-M sodium dodecanoate Chemical compound [Na+].CCCCCCCCCCCC([O-])=O BTURAGWYSMTVOW-UHFFFAOYSA-M 0.000 description 1
- 229940082004 sodium laurate Drugs 0.000 description 1
- MZSDGDXXBZSFTG-UHFFFAOYSA-M sodium;benzenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=CC=CC=C1 MZSDGDXXBZSFTG-UHFFFAOYSA-M 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011115 styrene butadiene Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 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
- VOZKAJLKRJDJLL-UHFFFAOYSA-N tolylenediamine group Chemical group CC1=C(C=C(C=C1)N)N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940117013 triethanolamine oleate Drugs 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Landscapes
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明は、水系ポリウレタン
樹脂組成物に関し、詳しくは、特定のエーテルエステル
化合物を配合してなる、水分散物の保存安定性および硬
化物物性に優れた水系ポリウレタン樹脂組成物に関す
る。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an aqueous polyurethane resin composition, and more particularly, to an aqueous polyurethane resin composition containing a specific ether ester compound and having excellent storage stability and physical properties of a cured product of an aqueous dispersion. About things.
【０００２】[0002]
【従来の技術及び発明が解決しようとする課題】塗料、
接着剤、バインダー、コーティング剤、繊維などの処理
剤あるいは各種仕上げ加工剤などの分野においてポリウ
レタン樹脂が用いられているが、斯る分野においても、
環境問題や人体への悪影響を考え、有機溶剤の使用が制
限されてきており、有機溶剤をほとんど含まない水系ポ
リウレタン樹脂への移行が進行し、その使用量も増加し
ている。BACKGROUND OF THE INVENTION Paints,
Adhesives, binders, coating agents, polyurethane resins are used in the field of treating agents such as fibers or various finishing agents, but also in such fields,
Considering environmental problems and adverse effects on the human body, the use of organic solvents has been restricted, and the transition to aqueous polyurethane resins containing almost no organic solvents has progressed, and the amount of use has increased.
【０００３】この水系ポリウレタン樹脂は、一般に、末
端にイソシアネート基を有するプレポリマーを、低分子
量の鎖延長剤および必要に応じて界面活性剤を含有する
水中に加えることによって鎖延長（高分子量化）と水分
散を同時に行わせて製造されるため、ポリマー主鎖に多
量のウレタン結合またはウレア結合を有することとな
り、その構造が剛直化し伸びが小さくなる欠点があっ
た。また、乾燥後に残存する界面活性剤は乾燥塗膜の物
性に悪影響を及ぼすことが多いため、界面活性剤の使用
量を低減したりあるいは界面活性剤を使用しなくとも水
分散性または水溶性を付与するために、分子中にカルボ
キシル基またはスルホン酸基を有するポリオールまたは
分子中に塩基性基を有するポリオールを用いて構造中に
親水性基を導入することも行われているが、この場合に
は、用いられるこれらのポリオールが低分子量の化合物
であるため、上記の欠点がより顕著に現れる。[0003] This aqueous polyurethane resin is generally subjected to chain extension (higher molecular weight) by adding a prepolymer having an isocyanate group at a terminal to water containing a low molecular weight chain extender and, if necessary, a surfactant. And water dispersion at the same time, the polymer has a large amount of urethane bonds or urea bonds in the main chain of the polymer. In addition, since the surfactant remaining after drying often adversely affects the physical properties of the dried coating film, the amount of the surfactant used can be reduced or the water dispersibility or water solubility can be reduced without using a surfactant. In order to impart, a hydrophilic group is introduced into the structure using a polyol having a carboxyl group or a sulfonic acid group in the molecule or a polyol having a basic group in the molecule. However, since these polyols used are low molecular weight compounds, the above-mentioned drawbacks appear more remarkably.
【０００４】また、繊維処理剤として水系ポリウレタン
樹脂を使用した場合にも、上記の欠点によって風合いが
不良となることが多かった。[0004] Also, when an aqueous polyurethane resin is used as a fiber treatment agent, the above-mentioned drawbacks often result in poor texture.
【０００５】これまで、ポリウレタン樹脂に可塑剤を配
合して柔軟性を付与することが行われており、例えば、
特開平７−２６１３７号公報にはジオクチルフタレー
ト、ジオクチルアジペート等のエステル系可塑剤、ポリ
オキシエチレンアルキルエーテル等のポリエーテル系可
塑剤、プロピレングリコールモノメチルエーテルアセテ
ート等の低分子量エーテルエステル系可塑剤を配合した
ポリウレタンエラストマーが記載されている。しかしな
がら、水系ポリウレタン樹脂にこれらの可塑剤を配合し
ても物性の改善効果が不十分で、また、クリーニングを
繰り返した場合にその効果が失われてしまうばかりでな
く、水系ポリウレタン樹脂の保存安定性が低下する欠点
もあり、実用上満足できるものではなかった。Heretofore, it has been practiced to add a plasticizer to a polyurethane resin to impart flexibility.
JP-A-7-26137 discloses an ester plasticizer such as dioctyl phthalate and dioctyl adipate, a polyether plasticizer such as polyoxyethylene alkyl ether, and a low molecular weight ether ester plasticizer such as propylene glycol monomethyl ether acetate. Described polyurethane elastomers. However, even if these plasticizers are added to the water-based polyurethane resin, the effect of improving the physical properties is insufficient, and the effect is not only lost when cleaning is repeated, but also the storage stability of the water-based polyurethane resin is reduced. However, it was not satisfactory in practical use.
【０００６】従って、本発明の目的は、水分散物の保存
安定性および硬化物物性に優れ、特に繊維製品の処理剤
として用いた場合において風合いがよく、消臭性、抗菌
性および耐洗濯性に優れた繊維製品を提供することが可
能な水系ポリウレタン樹脂組成物を提供することにあ
る。Accordingly, an object of the present invention is to provide an aqueous dispersion having excellent storage stability and physical properties of a cured product, especially when used as a treating agent for textile products, and having a good texture, deodorant properties, antibacterial properties and washing resistance. It is an object of the present invention to provide a water-based polyurethane resin composition capable of providing excellent fiber products.
【０００７】[0007]
【課題を解決するための手段】本発明者等は、種々検討
を重ねた結果、水系ポリウレタン樹脂に特定のエーテル
エステル化合物を配合することによって、上記目的が達
成されることを見出し、本発明に到達した。As a result of various studies, the present inventors have found that the above objects can be achieved by blending a specific ether ester compound with an aqueous polyurethane resin. Reached.
【０００８】即ち、本発明は、水系ウレタン樹脂に下記
一般式（Ｉ−１）〜（Ｉ−４）で表されるエーテルエス
テル化合物を配合してなる水系ポリウレタン樹脂組成物
を提供するものである。That is, the present invention provides an aqueous polyurethane resin composition comprising an aqueous urethane resin and ether ester compounds represented by the following general formulas (I-1) to (I-4). .
【０００９】[0009]
【化２】 Embedded image
【００１０】[0010]
【発明の実施の形態】以下、本発明の水系ポリウレタン
樹脂組成物について詳述する。BEST MODE FOR CARRYING OUT THE INVENTION Hereinafter, the water-based polyurethane resin composition of the present invention will be described in detail.
【００１１】本発明において用いられる水系ポリウレタ
ン樹脂は、例えば、（1)界面活性剤を用いて強制乳化す
る方法、（2)オキシエチレン骨格を導入して自己乳化性
を付与する方法あるいは（3)分子中にカチオン性基また
はアニオン性基を導入してこれを中和する方法などによ
り得られるものである。The aqueous polyurethane resin used in the present invention may be prepared, for example, by (1) a method of forcibly emulsifying using a surfactant, (2) a method of imparting self-emulsifying properties by introducing an oxyethylene skeleton, or (3) It is obtained by a method of introducing a cationic group or anionic group into a molecule and neutralizing the same.
【００１２】これらの中でも特に(3)の方法により得ら
れるものが、特に硬化物の風合いおよび耐水性などの物
性が優れ、かつ、水分散物の保存安定性が優れるため好
ましく、具体的には、有機ポリイソシアネート（Ａ）、
ポリオール（Ｂ）および分子中にカルボキシル基または
スルホン酸基を有するポリオールまたは分子中に塩基性
基を有するポリオール（Ｃ）を、反応に不活性で水との
親和性の大きい溶媒中でウレタン化反応させてプレポリ
マーとし、次いで、プレポリマーを中和、鎖延長し、水
を加えて水性ウレタン樹脂とすることによって製造され
る。Among these, those obtained by the method (3) are particularly preferable because the cured product has excellent physical properties such as texture and water resistance and also has excellent storage stability of an aqueous dispersion. , An organic polyisocyanate (A),
Urethane-forming reaction of the polyol (B) and the polyol having a carboxyl group or a sulfonic acid group in the molecule or the polyol (C) having a basic group in the molecule in a solvent inert to the reaction and having a high affinity for water. It is manufactured by making it into a prepolymer, then neutralizing and chain-extending the prepolymer, and adding water to obtain an aqueous urethane resin.
【００１３】水系ポリウレタン樹脂を製造するために使
用される上記有機ポリイソシアネート（Ａ）としては、
脂肪族、脂環式および芳香族ポリイソシアネートがあげ
られ、具体的には、２，４−トリレンジイソシアネー
ト、２，６−トリレンジイソシアネート、４，４−ジフ
ェニルメタンジイソシアネート、フェニレンジイソシア
ネート、キシリレンジイソシアネート、テトラメチルキ
シリレンジイソシアネート、テトラメチレンジイソシア
ネート、ヘキサメチレンジイソシアネート、リジンジイ
ソシアネートエステル、１，４−シクロヘキシレンジイ
ソシアネート、４，４’−ジシクロヘキシルメタンジイ
ソシアネート、３，３’−ジメトキシ−４，４’−ビフ
ェニレンジイソシアネート、１，５−ナフタレンジイソ
シアネート、１，５−テトラヒドロナフタレンジイソシ
アネート、イソホロンジイソシアネート等があげられ
る。The organic polyisocyanate (A) used for producing the aqueous polyurethane resin includes:
Examples thereof include aliphatic, alicyclic and aromatic polyisocyanates, and specifically, 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, 4,4-diphenylmethane diisocyanate, phenylene diisocyanate, xylylene diisocyanate, Tetramethylxylylene diisocyanate, tetramethylene diisocyanate, hexamethylene diisocyanate, lysine diisocyanate ester, 1,4-cyclohexylene diisocyanate, 4,4′-dicyclohexylmethane diisocyanate, 3,3′-dimethoxy-4,4′-biphenylene diisocyanate, Examples thereof include 1,5-naphthalenediisocyanate, 1,5-tetrahydronaphthalenediisocyanate, and isophorone diisocyanate.
【００１４】これらの有機ポリイソシアネート（Ａ）
は、上記ポリオール（Ｂ）、上記ポリオール（Ｃ）およ
び後述する鎖延長剤の活性水素の合計に対し、好ましく
は０．８〜３倍当量、より好ましくは１〜２倍当量とな
るように使用される。有機ポリイソシアネート（Ａ）の
使用量が０．８倍当量未満の場合には過剰のポリオール
等が残存することとなり、また、３倍当量より多い場合
には水を加えたときに尿素結合を多量に生成することと
なり、いずれの場合もその特性を低下させるおそれがあ
る。These organic polyisocyanates (A)
Is preferably used in an amount of 0.8 to 3 equivalents, more preferably 1 to 2 equivalents, based on the total of the active hydrogens of the polyol (B), the polyol (C) and the chain extender described below. Is done. If the amount of the organic polyisocyanate (A) used is less than 0.8 equivalents, excess polyol etc. will remain, and if it is more than 3 equivalents, a large amount of urea bonds will be formed when water is added. In any case, the characteristics may be reduced.
【００１５】水系ポリウレタン樹脂を製造するために使
用される上記ポリオール（Ｂ）としては、公知のポリオ
ールがあげられるが、芳香環構造を有するポリオールの
少なくとも一種を全ポリオール成分中１０重量％以上、
特に５０重量％以上を用いることが、より安定性に優れ
たものが得られるため好ましい。Examples of the polyol (B) used for producing the aqueous polyurethane resin include known polyols. At least one kind of polyol having an aromatic ring structure accounts for at least 10% by weight of the total polyol component.
In particular, it is preferable to use 50% by weight or more because a material having more excellent stability can be obtained.
【００１６】上記芳香環構造を有するポリオールとして
は、例えば、ハイドロキノン、レゾルシン、ビスフェノ
ールＡのエチレンオキシドおよび／またはプロピレンオ
キシド付加物等の芳香族環を有する低分子量ポリオール
あるいはこれらを開始剤としてエチレンオキシドおよび
／またはプロピレンオキシドを付加してなるポリエーテ
ルポリオール；エチレングリコール、ジエチレングリコ
ール、トリエチレングリコール、１，２−プロピレング
リコール、１，３−プロピレングリコール、１，２−ブ
チレングリコール、１，３−ブチレングリコール、１，
４−ブチレングリコール、ヘキサメチレングリコール、
ハイドロキノン、レゾルシン、水添ビスフェノールＡ、
ビスフェノールＡのエチレンオキシドおよび／またはプ
ロピレンオキシド付加物等の低分子量ポリオールあるい
はこれらを開始剤としてエチレンオキシドおよび／また
はプロピレンオキシドを付加して得られるポリエーテル
ポリオールとフタル酸、イソフタル酸、テレフタル酸、
トリメリット酸、ピロメリット酸、ビフェニルテトラカ
ルボン酸等の芳香族多価カルボン酸の少なくとも一種か
ら選ばれる多塩基酸との縮合物あるいはこれら芳香族多
価カルボン酸とともにコハク酸、グルタル酸、アジピン
酸、セバチン酸等のその他の多塩基酸との縮合物である
ポリエステルポリオールなどがあげられるが、特に芳香
族多価カルボン酸を用いて得られる芳香族環含有ポリオ
ールを用いることが、水分散物の保存安定性が一層優れ
たものが得られるため好ましい。Examples of the polyol having an aromatic ring structure include low molecular weight polyols having an aromatic ring such as hydroquinone, resorcinol, ethylene oxide and / or propylene oxide adducts of bisphenol A, or ethylene oxide and / or Polyether polyol obtained by adding propylene oxide; ethylene glycol, diethylene glycol, triethylene glycol, 1,2-propylene glycol, 1,3-propylene glycol, 1,2-butylene glycol, 1,3-butylene glycol, 1,
4-butylene glycol, hexamethylene glycol,
Hydroquinone, resorcinol, hydrogenated bisphenol A,
Low molecular weight polyols such as ethylene oxide and / or propylene oxide adducts of bisphenol A or polyether polyols obtained by adding ethylene oxide and / or propylene oxide using these as initiators and phthalic acid, isophthalic acid, terephthalic acid,
Condensates with polybasic acids selected from at least one of aromatic polycarboxylic acids such as trimellitic acid, pyromellitic acid and biphenyltetracarboxylic acid or succinic acid, glutaric acid, adipic acid together with these aromatic polycarboxylic acids Examples thereof include polyester polyols which are condensates with other polybasic acids such as sebacic acid, and the like. Particularly, it is possible to use an aromatic ring-containing polyol obtained using an aromatic polycarboxylic acid, It is preferable because a product having more excellent storage stability can be obtained.
【００１７】また、上記ポリオール（Ｂ）として用いら
れるその他の公知のポリオールとしては、例えば、エチ
レングリコール、ジエチレングリコール、トリエチレン
グリコール、１，２−プロピレングリコール、１，３−
プロピレングリコール、１，２−ブチレングリコール、
１，３−ブチレングリコール、１，４−ブチレングリコ
ール、ヘキサメチレングリコール、水添ビスフェノール
Ａのエチレンオキシドおよび／またはプロピレンオキシ
ド付加物等の低分子量ポリオール、ポリエチレングリコ
ール、ポリプロピレングリコール、ポリエチレン／プロ
ピレングリコール、ポリテトラメチレングリコール等、
または、上記低分子量ポリオールを開始剤としてエチレ
ンオキシドおよび／またはプロピレンオキシドを付加し
てなるポリエーテルポリオール、上記低分子量ポリオー
ルとコハク酸、グルタル酸、アジピン酸、セバチン酸等
の多塩基酸あるいは炭酸との縮合物であるポリエステル
ポリオール、ポリカーボネートポリオールおよびポリカ
プロラクトン等があげられる。Other known polyols used as the polyol (B) include, for example, ethylene glycol, diethylene glycol, triethylene glycol, 1,2-propylene glycol, 1,3-
Propylene glycol, 1,2-butylene glycol,
Low molecular weight polyols such as 1,3-butylene glycol, 1,4-butylene glycol, hexamethylene glycol, ethylene oxide and / or propylene oxide adduct of hydrogenated bisphenol A, polyethylene glycol, polypropylene glycol, polyethylene / propylene glycol, polytetra Methylene glycol, etc.
Alternatively, a polyether polyol obtained by adding ethylene oxide and / or propylene oxide using the low molecular weight polyol as an initiator, or a polyether polyol or a carbonic acid such as succinic acid, glutaric acid, adipic acid, sebacic acid or the like, or a polyether polyol obtained by adding ethylene oxide and / or propylene oxide. Examples of the condensate include polyester polyol, polycarbonate polyol, and polycaprolactone.
【００１８】水系ポリウレタン樹脂を製造するために使
用される上記ポリオール（Ｃ）のうち、分子中にカルボ
キシル基もしくはスルホン酸基を有するポリオールとし
ては、例えば、２，２−ジメチロールプロピオン酸、
２，２−ジメチロール酪酸、２，２−ジメチロール吉草
酸、１，４−ブタンジオール−２−スルホン酸等があげ
られ、また、分子中に塩基性基を有するポリオールとし
ては、例えば、メチルジエタノールアミン、ブチルジエ
タノールアミン、トリエタノールアミン、トリイソプロ
パノールアミンなどがあげられ、特に、カルボキシル基
を有するポリオールを用いた場合には分散性に優れる水
性ウレタンが得られるので好ましい。Among the polyols (C) used for producing the aqueous polyurethane resin, the polyols having a carboxyl group or a sulfonic acid group in the molecule include, for example, 2,2-dimethylolpropionic acid,
2,2-dimethylolbutyric acid, 2,2-dimethylolvaleric acid, 1,4-butanediol-2-sulfonic acid, and the like. Examples of the polyol having a basic group in the molecule include methyldiethanolamine. Examples thereof include butyldiethanolamine, triethanolamine, and triisopropanolamine. In particular, when a polyol having a carboxyl group is used, an aqueous urethane having excellent dispersibility is preferably obtained.
【００１９】これらのポリオール（Ｃ）の使用量は、用
いるポリオールおよびポリイソシアネートの種類にもよ
るが、通常は、水系ポリウレタン樹脂を構成する全ての
反応成分に対して、０．５〜５０重量％、好ましくは１
〜３０重量％が用いられる。ポリオール（Ｃ）の使用量
が０．５重量％未満では保存安定性が劣り、また、５０
重量％を超えて使用すると特性に悪影響を及ぼすことが
ある。The amount of the polyol (C) used depends on the types of the polyol and the polyisocyanate to be used, but is usually 0.5 to 50% by weight based on all the reaction components constituting the aqueous polyurethane resin. , Preferably 1
~ 30% by weight is used. When the amount of the polyol (C) used is less than 0.5% by weight, the storage stability is poor, and
If used in excess of weight percent, properties may be adversely affected.
【００２０】水系ポリウレタン樹脂を製造するために使
用される上記の反応に不活性で水との親和性の大きい溶
媒としては、例えば、アセトン、メチルエチルケトン、
ジオキサン、テトラヒドロフラン、Ｎ−メチル−２−ピ
ロリドン等をあげることができる。これらの溶媒は、通
常、プレポリマーを製造するために用いられる上記原料
の合計重量に対して、１０〜１００重量％が用いられ
る。Examples of the solvent which is inert to the above reaction and has a high affinity for water used for producing the aqueous polyurethane resin include acetone, methyl ethyl ketone, and the like.
Dioxane, tetrahydrofuran, N-methyl-2-pyrrolidone and the like can be mentioned. These solvents are usually used in an amount of 10 to 100% by weight based on the total weight of the raw materials used for producing the prepolymer.
【００２１】また、上記プレポリマーを中和する中和剤
としては、上記プレポリマーがアニオン系の場合（ポリ
オール（Ｃ）として分子中にカルボキシル基もしくはス
ルホン酸基を有するポリオールを使用した場合）と、上
記プレポリマーがカチオン系の場合（ポリオール（Ｃ）
として塩基性基を有するポリオールを使用した場合）と
によって異なり、上記プレポリマーがアニオン系の場
合、例えば、トリメチルアミン、トリエチルアミン、ト
リプロピルアミン、トリブチルアミン、Ｎ−メチルジエ
タノールアミン、トリエタノールアミン等の有機アミ
ン、水酸化ナトリウム、水酸化カリウム、アンモニア等
の無機塩基があげられ、これらはカルボキシル基または
スルホン酸基を中和するに十分な量が用いられる。ま
た、上記プレポリマーがカチオン系の場合、例えば、蟻
酸、蓚酸、リン酸、硼酸、塩酸、炭酸、酢酸、ジメチロ
ールプロピオン酸等の酸類があげられ、これらはポリオ
ール塩基を中和するのに十分な量が用いられる。Examples of the neutralizing agent for neutralizing the prepolymer include a case where the prepolymer is anionic (when a polyol having a carboxyl group or a sulfonic acid group in the molecule is used as the polyol (C)). When the prepolymer is cationic (polyol (C)
When a polyol having a basic group is used as the above), when the above prepolymer is anionic, for example, an organic amine such as trimethylamine, triethylamine, tripropylamine, tributylamine, N-methyldiethanolamine, triethanolamine, etc. And inorganic bases such as sodium hydroxide, potassium hydroxide, and ammonia. These are used in an amount sufficient to neutralize a carboxyl group or a sulfonic acid group. When the prepolymer is cationic, examples thereof include acids such as formic acid, oxalic acid, phosphoric acid, boric acid, hydrochloric acid, carbonic acid, acetic acid, and dimethylolpropionic acid, which are sufficient to neutralize the polyol base. The amount used.
【００２２】また、上記プレポリマーを鎖延長する鎖延
長剤としては、例えば、エチレングリコール、プロピレ
ングリコールなどのポリオール類、エチレンジアミン、
プロピレンジアミン、ヘキサメチレンジアミン、トリレ
ンジアミン、キシリレンジアミン、ジアミノジフェニル
メタン、ジアミノシクロヘキシルメタン、ピペラジン、
２−メチルピペラジン、イソホロンジアミン、メラミ
ン、コハク酸ジヒドラジド、アジピン酸ジヒドラジド、
フタル酸ジヒドラジド等のアミン類および水等があげら
れる。これらの鎖延長剤の使用量は、目的とするポリウ
レタン樹脂の分子量にもよるが、通常は、プレポリマー
に対して０．５〜１０重量％が用いられる。Examples of the chain extender for chain extending the prepolymer include polyols such as ethylene glycol and propylene glycol, ethylene diamine, and the like.
Propylenediamine, hexamethylenediamine, tolylenediamine, xylylenediamine, diaminodiphenylmethane, diaminocyclohexylmethane, piperazine,
2-methylpiperazine, isophoronediamine, melamine, succinic dihydrazide, adipic dihydrazide,
Amines such as phthalic dihydrazide; water; The amount of the chain extender used depends on the molecular weight of the target polyurethane resin, but is usually 0.5 to 10% by weight based on the prepolymer.
【００２３】前述のように、これらの原料から水系ポリ
ウレタン樹脂を製造する製造方法自体は周知であり、こ
れらの原料の仕込み順序を適宜変更したり、あるいは分
割して仕込むことも可能である。As described above, the production method itself for producing an aqueous polyurethane resin from these raw materials is well known, and it is also possible to appropriately change the order of charging these raw materials or to divide them and charge them.
【００２４】このようにして得られた水系ポリウレタン
樹脂は、通常、樹脂固形分が１〜９０重量％、より好ま
しくは５〜８０重量％となるように調整される。The water-based polyurethane resin thus obtained is usually adjusted to have a resin solid content of 1 to 90% by weight, more preferably 5 to 80% by weight.
【００２５】また、水系ポリウレタン樹脂としては、市
販されている水系ポリウレタン樹脂をそのまま使用する
ことも勿論可能であり、例えば、旭電化工業（株）製の
「アデカボンタイター」シリーズ、三井東圧化学（株）
製の「オレスター」シリーズ、大日本インキ化学工業
（株）製の「ボンディック」シリーズ、「ハイドラン」
シリーズ、バイエル社製の「インプラニール」シリー
ズ、日本ソフラン（株）製の「ソフラネート」シリー
ズ、花王（株）製の「ポイズ」シリーズ、三洋化成工業
（株）製の「サンプレン」シリーズ、保土谷化学工業
（株）製の「アイゼラックス」シリーズ、第一工業製薬
（株）製の「スーパーフレックス」シリーズ、ゼネカ
（株）製の「ネオレッツ」シリーズ等を用いることがで
きる。As the water-based polyurethane resin, a commercially available water-based polyurethane resin can of course be used as it is. For example, “Adekabon Titer” series manufactured by Asahi Denka Kogyo Co., Ltd., Mitsui Toatsu Chemicals, Inc. (stock)
"Orester" series, Dainippon Ink & Chemicals, Inc. "Bondick" series, "Hydran"
Series, Bayer's "Impranil" series, Japan Sofran Co., Ltd.'s "Sofranate" series, Kao Corporation's "Poise" series, Sanyo Chemical Industries'"Samprene" series, Hodogaya The “Izelux” series manufactured by Chemical Industry Co., Ltd., the “Superflex” series manufactured by Daiichi Kogyo Seiyaku Co., Ltd., and the “Neoretz” series manufactured by Zeneca Corporation can be used.
【００２６】また、上記水系ポリウレタン樹脂に配合さ
れる上記一般式（Ｉ−１）〜（Ｉ−４）で表されるエー
テルエステル化合物において、該一般式中のR1、R3およ
びR4で示される炭素原子数１〜１８のアルキル基として
は、例えば、メチル、エチル、プロピル、ブチル、ペン
チル、ヘキシル、ヘプチル、オクチル、ノニル、デシ
ル、ウンデシル、ドデシル、トリデシル、テトラデシ
ル、ペンタデシル、ヘキサデシル、ヘプタデシル、オク
タデシルなどの直鎖あるいは分岐の基があげられ、アリ
ール基としては、例えば、フェニル、ナフチルなどがあ
げられ、アルキルアリール基としては、例えば、上記ア
ルキル基によって置換されてなる上記アリール基などが
あげられ、R2で表される炭素原子数１〜１２のアルキレ
ン基としては、例えば、エチレン、プロピレン、ブチレ
ン、ペンチレン、ヘキシレン、ヘプチレン、オクチレ
ン、ノニレン、デシレン、ウンデシレン、ドデシレンな
どの直鎖あるいは分岐の基があげられ、アリーレン基と
しては、例えば、フェニレン、ナフチレンなどの基があ
げられ、Ａで表される炭素原子数２〜４のアルキレン基
としては、エチレン、プロピレン、ブチレンなどの直鎖
あるいは分岐の基があげられる。In the ether ester compounds represented by the above general formulas (I-1) to (I-4) to be mixed with the above-mentioned water-based polyurethane resin, R 1 , R 3 and R 4 in the above general formulas Examples of the alkyl group having 1 to 18 carbon atoms include, for example, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, Examples thereof include straight-chain or branched groups such as octadecyl. Examples of the aryl group include phenyl and naphthyl. Examples of the alkylaryl group include the above-described aryl group substituted by the above-mentioned alkyl group. And as the alkylene group having 1 to 12 carbon atoms represented by R 2 , for example, Straight-chain or branched groups such as ethylene, propylene, butylene, pentylene, hexylene, heptylene, octylene, nonylene, decylene, undecylene, dodecylene, and the like, and examples of the arylene group include groups such as phenylene and naphthylene. Examples of the alkylene group having 2 to 4 carbon atoms represented by A include linear or branched groups such as ethylene, propylene, and butylene.
【００２７】上記一般式（Ｉ−１）〜（Ｉ−４）で表さ
れるエーテルエステル化合物としては、例えば、下記の
化合物１〜４０などがあげられる。ここでｎは１〜２０
の数を表す。Examples of the ether ester compounds represented by the general formulas (I-1) to (I-4) include the following compounds 1 to 40. Where n is 1 to 20
Represents the number of
【００２８】[0028]
【化３】 Embedded image
【００２９】[0029]
【化４】 Embedded image
【００３０】[0030]
【化５】 Embedded image
【００３１】[0031]
【化６】 Embedded image
【００３２】[0032]
【化７】 Embedded image
【００３３】これらエーテルエステル化合物は、水系ポ
リウレタン樹脂の樹脂固形分１００重量部に対して、好
ましくは１〜１００重量部、より好ましくは５〜５０重
量部使用され、１重量部未満の使用ではその使用効果が
ほとんどみられず、１００重量部を越えて使用した場合
には、硬化物の物性を低下するおそれがある。These ether ester compounds are preferably used in an amount of 1 to 100 parts by weight, more preferably 5 to 50 parts by weight, based on 100 parts by weight of the solid content of the aqueous polyurethane resin. There is almost no use effect, and when used in an amount exceeding 100 parts by weight, the physical properties of the cured product may be reduced.
【００３４】エーテルエステル化合物を水系ポリウレタ
ン樹脂に配合する方法は、水系ポリウレタン樹脂製造後
に配合する方法でもよく、エーテルエステル化合物の存
在下で有機ポリイソシアネート（Ａ）、ポリオール
（Ｂ）およびポリオール（Ｃ）を反応させることによっ
て最終製品に残存させる方法でもよい。The method of blending the ether ester compound with the aqueous polyurethane resin may be a method of blending it after the production of the aqueous polyurethane resin, and the organic polyisocyanate (A), the polyol (B) and the polyol (C) in the presence of the ether ester compound. May be allowed to remain in the final product by reacting.
【００３５】また、本発明の水系ポリウレタン樹脂組成
物には、乳化剤を配合することができ、該乳化剤として
は、アニオン性界面活性剤、ノニオン性界面活性剤、カ
チオン性界面活性剤、両性界面活性剤、高分子界面活性
剤または反応性界面活性剤など全ての界面活性剤を使用
することができる。The aqueous polyurethane resin composition of the present invention may contain an emulsifier, such as an anionic surfactant, a nonionic surfactant, a cationic surfactant, an amphoteric surfactant. All surfactants can be used, such as agents, polymeric surfactants or reactive surfactants.
【００３６】上記アニオン性界面活性剤としては、例え
ば、ナトリウムドデシルサルフェート、カリウムドデシ
ルサルフェート、アンモニウムドデシルサルフェートな
どのアルキルサルフェート；ナトリウムドデシルポリグ
リコールエーテルサルフェート；ナトリウムスルホリシ
ノート；スルホン化パラフィンのアルカリ金属塩、スル
ホン化パラフィンのアンモニウム塩などのアルキルスル
ホネート；ナトリウムラウレート、トリエタノールアミ
ンオレート、トリエタノールアミンアビエテートなどの
脂肪酸塩；ナトリウムベンゼンスルホネート、アルカリ
フェノールヒドロキシエチレンのアルカリ金属サルフェ
ートなどのアルキルアリールスルホネート；高アルキル
ナフタレンスルホン酸塩；ナフタレンスルホン酸ホルマ
リン縮合物；ジアルキルスルホコハク酸塩；ポリオキシ
エチレンアルキルサルフェート塩；ポリオキシエチレン
アルキルアリールサルフェート塩などがあげられる。Examples of the anionic surfactant include alkyl sulfates such as sodium dodecyl sulfate, potassium dodecyl sulfate, and ammonium dodecyl sulfate; sodium dodecyl polyglycol ether sulfate; sodium sulfolicine; alkali metal salts of sulfonated paraffin; Alkyl sulfonates such as ammonium salts of sulfonated paraffins; fatty acid salts such as sodium laurate, triethanolamine oleate and triethanolamine aviate; alkyl aryl sulfonates such as sodium benzene sulfonate and alkali metal sulfate of alkali phenol hydroxyethylene; high alkyl Naphthalenesulfonic acid salt; Naphthalenesulfonic acid formalin condensate; Dia Kill sulfosuccinate; polyoxyethylene alkyl sulfate salt; and polyoxyethylene alkyl aryl sulfate salts.
【００３７】上記ノニオン性界面活性剤としては、例え
ば、ポリオキシエチレンアルキルエーテル；ポリオキシ
エチレンアルキルアリールエーテル；ソルビタン脂肪酸
エステル；ポリオキシエチレンソルビタン脂肪酸エステ
ル；脂肪酸モノグリセライド；トリメチロールプロパン
脂肪酸エステル；ポリオキシエチレンオキシプロピレン
共重合体；エチレンオキサイドの脂肪酸アミン、アミド
または酸との縮合生成物などがあげられる。Examples of the nonionic surfactant include polyoxyethylene alkyl ether; polyoxyethylene alkyl aryl ether; sorbitan fatty acid ester; polyoxyethylene sorbitan fatty acid ester; fatty acid monoglyceride; trimethylolpropane fatty acid ester; Oxypropylene copolymers include condensation products of ethylene oxide with fatty acid amines, amides or acids.
【００３８】上記カチオン性界面活性剤としては、例え
ば、第１〜３級アミン塩；ピリジニウム塩；第４級アン
モニウム塩などがあげられる。The cationic surfactant includes, for example, primary to tertiary amine salts; pyridinium salts; and quaternary ammonium salts.
【００３９】上記高分子界面活性剤としては、例えば、
ポリビニルアルコール；ポリ（メタ）アクリル酸ナトリ
ウム、ポリ（メタ）アクリル酸カリウム、ポリ（メタ）
アクリル酸アンモニウム、ポリヒドロキシエチル（メ
タ）アクリレート；ポリヒドロキシプロピル（メタ）ア
クリレート；またこれらの重合体構成単位である重合性
単量体の２種以上の共重合体または他の単量体との共重
合体などがあげられる。また、クラウンエーテル類など
の相関移動触媒と称されるものも界面活性を示すものと
して有用である。As the above-mentioned polymer surfactant, for example,
Polyvinyl alcohol; sodium poly (meth) acrylate, potassium poly (meth) acrylate, poly (meth)
Ammonium acrylate, polyhydroxyethyl (meth) acrylate; polyhydroxypropyl (meth) acrylate; and a copolymer of two or more of the polymerizable monomers that are the constituent units of these polymers or other monomers And copolymers. In addition, what is called a phase transfer catalyst such as crown ethers is also useful as one showing surface activity.
【００４０】本発明の水系ポリウレタン樹脂組成物に
は、必要に応じて他の水性分散体や水分散液、例えば、
酢酸ビニル系、エチレン−酢酸ビニル系、アクリル系、
アクリル−スチレン系等のエマルジョン；スチレン−ブ
タジエン系、アクリロニトリル−ブタジエン系、アクリ
ル−ブタジエン系等のラテックス；ポリエチレン系、ポ
リオレフィン系等のアイオノマー；ポリエステル、ポリ
アミド、エポキシ樹脂等の各種水性分散体、水分散液を
併用することができる。The aqueous polyurethane resin composition of the present invention may optionally contain other aqueous dispersions or aqueous dispersions, for example,
Vinyl acetate, ethylene-vinyl acetate, acrylic,
Emulsions such as acryl-styrene type; latexes such as styrene-butadiene type, acrylonitrile-butadiene type and acryl-butadiene type; ionomers such as polyethylene type and polyolefin type; various aqueous dispersions such as polyester, polyamide and epoxy resin, and water dispersion Liquids can be used together.
【００４１】また、本発明の水系ポリウレタン樹脂組成
物には、必要に応じて、フェノール系抗酸化剤、有機ホ
スファイトまたはホスホナイトなどの有機リン系抗酸化
剤、チオエーテル系抗酸化剤、紫外線吸収剤あるいはヒ
ンダードアミン化合物などの光安定剤、フッ素系または
シロキサン系などの帯電防止剤、コロイダルシリカまた
はコロイダルアルミナなどの無機質コロイドゾル、シラ
ンカップリング剤、着色剤、ワックス類、防腐剤、消泡
剤、可塑剤、フィラー、溶剤、造膜助剤、分散剤、増粘
剤、香料等の慣用の添加物を加えることもできる。The aqueous polyurethane resin composition of the present invention may contain, if necessary, a phenolic antioxidant, an organic phosphorus antioxidant such as organic phosphite or phosphonite, a thioether antioxidant, and an ultraviolet absorber. Or a light stabilizer such as a hindered amine compound, an antistatic agent such as a fluorine-based or siloxane-based one, an inorganic colloid sol such as colloidal silica or colloidal alumina, a silane coupling agent, a coloring agent, a wax, a preservative, an antifoaming agent, and a plasticizer. Conventional additives such as fillers, solvents, film-forming auxiliaries, dispersants, thickeners, and fragrances can also be added.
【００４２】本発明の水系ポリウレタン樹脂組成物は、
塗料、接着剤、バインダー、コーティング剤、繊維など
の処理剤あるいは各種仕上げ加工剤などの分野において
使用することができ、とりわけ、繊維製品の処理剤とし
て使用する場合、風合いを与え、また、難燃、消臭、抗
菌効果もあるので好ましい。The aqueous polyurethane resin composition of the present invention comprises:
It can be used in the field of treating agents such as paints, adhesives, binders, coating agents and fibers or various finishing agents. Especially when used as a treating agent for textile products, it gives a good texture and flame retardancy. It is preferable because it has deodorant and antibacterial effects.
【００４３】本発明の水系ポリウレタン樹脂組成物を繊
維製品の仕上げ剤として使用する場合の繊維基材として
は、例えば、綿、麻等の天然繊維、レーヨン、ナイロ
ン、ポリエステル、ポリウレタン、アクリル等の人工・
合成繊維、またこれらの混紡繊維あるいはガラス繊維、
炭素繊維等の無機繊維などがあげられる。When the water-based polyurethane resin composition of the present invention is used as a finishing agent for textile products, examples of the fiber base include natural fibers such as cotton and hemp, and artificial fibers such as rayon, nylon, polyester, polyurethane and acrylic.・
Synthetic fibers, blended fibers or glass fibers of these,
Examples include inorganic fibers such as carbon fibers.
【００４４】本発明の水系ポリウレタン樹脂組成物を繊
維製品の仕上げ剤として使用する場合には、これを含有
する処理浴を予め調製し、この中に繊維基材を浸漬、含
浸させ、必要な付着量となるようマングロール等で絞
り、乾燥させればよい。When the water-based polyurethane resin composition of the present invention is used as a finishing agent for textile products, a treatment bath containing the same is prepared in advance, and the fiber base material is immersed and impregnated in the bath, and the necessary adhesion is obtained. What is necessary is just to squeeze with a mangrol or the like so as to obtain an amount and to dry it.
【００４５】また、本発明の水系ポリウレタン樹脂組成
物を塗料などとして使用する場合には、グラビアコート
法、リバースロールコート法、エアナイフコート法、バ
ーコート法、ドクターブレードコート法、カーテンロー
ルコート法、ディップコート法、スプレーコート法、ロ
ッドコート法などのコーティング法を用いて、基材に塗
布して乾燥することによって、塗膜を形成することがで
きる。When the aqueous polyurethane resin composition of the present invention is used as a paint or the like, a gravure coating method, a reverse roll coating method, an air knife coating method, a bar coating method, a doctor blade coating method, a curtain roll coating method, A coating film can be formed by applying the composition to a substrate using a coating method such as a dip coating method, a spray coating method, and a rod coating method and then drying the coating.
【００４６】[0046]
【実施例】以下、製造例および実施例によって本発明を
さらに詳細に説明するが、本発明は下記の実施例によっ
て制限を受けるものではない。尚、製造例および実施例
における部は特にことわりのないかぎり重量部を表す。EXAMPLES The present invention will be described in more detail with reference to Production Examples and Examples, but the present invention is not limited by the following Examples. Parts in Production Examples and Examples are parts by weight unless otherwise specified.
【００４７】製造例１ ポリエステルポリオール１（イソフタル酸／アジピン酸
〔１：１〕とヘキサンジオールの縮合物、平均分子量１
０００）１００部、イソホロンジイソシアネート１０７
部、ジメチロールプロピオン酸２０部およびＮ−メチル
ピロリドン１００部を反応容器にとり、８０〜１００℃
に保ちながら反応させて、プレポリマーを製造した。Production Example 1 Polyester polyol 1 (condensate of isophthalic acid / adipic acid [1: 1] and hexanediol, average molecular weight 1
000) 100 parts, isophorone diisocyanate 107
Parts, 20 parts of dimethylolpropionic acid and 100 parts of N-methylpyrrolidone in a reaction vessel.
To produce a prepolymer.
【００４８】次いで、トリエチルアミン１８部を加えて
中和した後、ヘキサメチレンジアミン５部を加え、水を
添加しながら３５℃以下で架橋反応を行い、反応終了ま
でに６５０部の水を加えて樹脂固形分２３重量％の水系
ポリウレタン樹脂Ａを製造した。Next, 18 parts of triethylamine was added to neutralize the mixture, 5 parts of hexamethylenediamine was added, and a crosslinking reaction was carried out at 35 ° C. or less while adding water. An aqueous polyurethane resin A having a solid content of 23% by weight was produced.
【００４９】上記製造例１と同様な操作により、次の
〔表１〕の水系ポリウレタン樹脂ＢおよびＣを製造し
た。In the same manner as in Production Example 1, the following aqueous polyurethane resins B and C in Table 1 were produced.
【００５０】製造例２ ポリエステルポリオール１（イソフタル酸／アジピン酸
〔１：１〕とヘキサンジオールの縮合物、平均分子量１
０００）１００部、イソホロンジイソシアネート１０７
部、ジメチロールプロピオン酸２０部、Ｎ−メチルピロ
リドン１００部およびエーテルエステル化合物１０（ｎ
＝７）１００部を反応容器にとり、８０〜１００℃に保
ちながら反応させて、プレポリマーを製造した。Production Example 2 Polyester polyol 1 (condensate of isophthalic acid / adipic acid [1: 1] and hexanediol, average molecular weight 1
000) 100 parts, isophorone diisocyanate 107
Parts, dimethylolpropionic acid 20 parts, N-methylpyrrolidone 100 parts and ether ester compound 10 (n
= 7) 100 parts were placed in a reaction vessel and reacted while keeping at 80 to 100 ° C to produce a prepolymer.
【００５１】次いで、トリエチルアミン１８部を加えて
中和した後、ヘキサメチレンジアミン５部を加え、水を
添加しながら３５℃以下で架橋反応を行い、反応終了ま
でに５５０部の水を加えて樹脂固形分３３重量％の水系
ポリウレタン樹脂Ｄを製造した。Next, 18 parts of triethylamine was added for neutralization, 5 parts of hexamethylenediamine was added, and a crosslinking reaction was carried out at 35 ° C. or less while adding water. An aqueous polyurethane resin D having a solid content of 33% by weight was produced.
【００５２】上記製造例２と同様な操作により、次の
〔表１〕の水系ポリウレタン樹脂Ｅ〜Ｇを製造した。By the same operation as in Production Example 2, the following aqueous polyurethane resins EG of Table 1 were produced.
【００５３】[0053]
【表１】 [Table 1]
【００５４】実施例１ 上記製造例により得られた水系ポリウレタン樹脂を用い
て、次の〔表２〕および〔表３〕に示したような水性分
散体（水系ポリウレタン樹脂組成物）を調製し、５℃お
よび４０℃で３か月および６か月後の保存安定性を下記
基準により評価した。ただし、可塑剤成分を配合する場
合は、水系ポリウレタン樹脂の樹脂固形分１００部に対
して１０部撹拌混合した。Example 1 An aqueous dispersion (aqueous polyurethane resin composition) as shown in the following [Table 2] and [Table 3] was prepared using the aqueous polyurethane resin obtained in the above Production Example. The storage stability after 3 months and 6 months at 5 ° C and 40 ° C was evaluated according to the following criteria. However, when a plasticizer component was blended, 10 parts of the water-based polyurethane resin was stirred and mixed with 100 parts of the resin solid content.
【００５５】（保存安定性の評価基準） １：良好なエマルジョンを保っている。 ２：若干分離が見られる。 ３：分離が見られる。 ４：完全に分離している。(Evaluation Criteria for Storage Stability) 1: A good emulsion is maintained. 2: Slight separation is observed. 3: Separation is observed. 4: Completely separated.
【００５６】また、型枠をつけたガラス板上にシートの
厚さ１ｍｍとなるように上記水性分散体を流し込み、４
０℃で２日間乾燥した。これを１００℃で３分間乾燥し
てＪＩＳ Ｋ ７１１３に準じて１００％モジュラス
（Ｋｇ／ｃｍ2 ）および伸び（％）を求めた。The aqueous dispersion was poured onto a glass plate provided with a mold so that the thickness of the sheet became 1 mm.
Dry at 0 ° C. for 2 days. This was dried at 100 ° C. for 3 minutes, and 100% modulus (Kg / cm 2 ) and elongation (%) were determined according to JIS K 7113.
【００５７】また、上記水性分散体にＴ／Ｃ＝６５／３
５綿ブロード布を浸漬し、マングルロールで固形分付着
率７０％に絞った後、１００℃で２分さらに１７０℃で
１分熱風乾燥処理し、剛軟度、風合いおよび色合いを評
価した。また、ドライクリーニングを３回実施したもの
についても評価した。Further, T / C = 65/3 was added to the aqueous dispersion.
A 5-cotton broad cloth was immersed and squeezed with a mangle roll to a solid content adhering rate of 70%, followed by hot air drying at 100 ° C. for 2 minutes and further at 170 ° C. for 1 minute to evaluate the softness, texture and color. In addition, those which performed dry cleaning three times were also evaluated.
【００５８】ここで剛軟度は、ＪＩＳ Ｌ １０９６に
準じてカンチレバー法にて剛軟度を測定し、風合いは手
触り、色合いは目視により評価した。Here, the bending resistance was measured by the cantilever method according to JIS L 1096, and the texture was evaluated by touch and the color was visually evaluated.
【００５９】その結果を次の〔表２〕および〔表３〕に
示した。The results are shown in the following [Table 2] and [Table 3].
【００６０】[0060]
【表２】 [Table 2]
【００６１】[0061]
【表３】 [Table 3]
【００６２】実施例および比較例から明らかなように、
水系ポリウレタン樹脂に可塑剤成分を全く使用しない場
合（比較例１−３）には柔軟性が得られず、これで繊維
製品を処理した場合にも、風合いは硬く、色合いもくす
んだ感じのものしかえられず、これに本発明以外のエー
テルエステル化合物を配合した場合（比較例１−１）も
これらの改善効果は小さい。さらに汎用の可塑剤である
ジ−２−エチルヘキシルフタレート又はエポキシ化大豆
油を配合したもの（比較例１−４および比較例１−２）
は、繊維処理剤として使用した場合に初期における風合
いや色合いは優れたものを提供するが、クリーニングを
繰り返すことによりその性能は低下し、エマルジョンの
保存安定性も不十分である。As is clear from the examples and comparative examples,
When no plasticizer component is used in the water-based polyurethane resin (Comparative Example 1-3), flexibility is not obtained. Even when a textile product is treated with this, the texture is hard and the color is dull. However, when an ether ester compound other than the present invention is added thereto (Comparative Example 1-1), these improvement effects are small. Further blended with di-2-ethylhexyl phthalate or epoxidized soybean oil which is a general-purpose plasticizer (Comparative Examples 1-4 and 1-2)
When used as a fiber treatment agent, they provide excellent initial texture and color, but their performance is reduced by repeated cleaning, and the storage stability of the emulsion is insufficient.
【００６３】これに対して、水系ポリウレタン樹脂に特
定のエーテルエステル化合物を配合してなる本発明の水
系ポリウレタン樹脂組成物を繊維処理剤として使用した
場合（実施例１−１〜１−９）には、エマルジョンの安
定性に優れ、また柔軟なシートを提供し、さらに繊維に
良好な風合いや色合いを付与し、クリーニングをした後
においてもその性能は維持される。On the other hand, when the aqueous polyurethane resin composition of the present invention obtained by blending a specific ether ester compound with the aqueous polyurethane resin is used as a fiber treating agent (Examples 1-1 to 1-9). Has excellent emulsion stability and provides a flexible sheet, imparts good texture and color to the fibers, and maintains its performance even after cleaning.
【００６４】[0064]
【発明の効果】本発明の水系ポリウレタン樹脂組成物
は、水分散物の保存安定性および硬化物物性に優れ、特
に繊維製品の処理剤として用いた場合において風合いが
よく、消臭性、抗菌性および耐洗濯性に優れた繊維製品
を提供することが可能である。The aqueous polyurethane resin composition of the present invention is excellent in storage stability and physical properties of a cured product of an aqueous dispersion, particularly when used as a treating agent for textiles, and has a good deodorizing property and an antibacterial property. Further, it is possible to provide a textile product having excellent washing resistance.
Claims (4)
−１）〜（Ｉ−４）で表されるエーテルエステル化合物
を配合してなる水系ポリウレタン樹脂組成物。 【化１】 1. An aqueous polyurethane resin having the following general formula (I)
An aqueous polyurethane resin composition comprising the ether ester compounds represented by -1) to (I-4). Embedded image
０重量部に対し、エーテルエステル化合物１〜１００重
量部を配合してなる請求項１記載の水系ポリウレタン樹
脂組成物。2. A resin solid content of an aqueous polyurethane resin of 10
The aqueous polyurethane resin composition according to claim 1, wherein 1 to 100 parts by weight of the ether ester compound is blended with respect to 0 parts by weight.
シアネート（Ａ）、ポリオール（Ｂ）および分子中にカ
ルボキシル基もしくはスルホン酸基を有するポリオール
または分子中に塩基性基を有するポリオール（Ｃ）から
製造されるポリウレタン樹脂に、中和剤を併用したもの
である請求項１または２記載の水系ポリウレタン樹脂組
成物。3. An aqueous polyurethane resin is produced from an organic polyisocyanate (A), a polyol (B) and a polyol having a carboxyl group or a sulfonic acid group in a molecule or a polyol (C) having a basic group in a molecule. 3. The aqueous polyurethane resin composition according to claim 1, wherein a neutralizing agent is used in combination with said polyurethane resin.
有するポリオールの少なくとも一種を使用する請求項１
〜３のいずれかに記載の水系ポリウレタン樹脂組成物。4. The method according to claim 1, wherein at least one polyol having an aromatic ring structure is used as the polyol (B).
4. The aqueous polyurethane resin composition according to any one of items 1 to 3.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP25723197A JP3957018B2 (en) | 1997-09-22 | 1997-09-22 | Water-based polyurethane resin composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP25723197A JP3957018B2 (en) | 1997-09-22 | 1997-09-22 | Water-based polyurethane resin composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH1192654A true JPH1192654A (en) | 1999-04-06 |
| JP3957018B2 JP3957018B2 (en) | 2007-08-08 |
Family
ID=17303506
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP25723197A Expired - Fee Related JP3957018B2 (en) | 1997-09-22 | 1997-09-22 | Water-based polyurethane resin composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3957018B2 (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005075587A1 (en) * | 2004-02-06 | 2005-08-18 | Nippon Paint Co., Ltd. | Water-based intercoating composition and method of forming multilayered coating film |
| WO2005075534A1 (en) * | 2004-02-06 | 2005-08-18 | Adeka Corporation | Aqueous dispersion type polyurethane composition |
| JP2007269832A (en) * | 2006-03-30 | 2007-10-18 | Arakawa Chem Ind Co Ltd | Method of manufacturing polyurethane resin aqueous dispersion |
| CN102618010A (en) * | 2012-03-08 | 2012-08-01 | 广州聚天化工科技有限公司 | Continuous production device and method for regenerating polyol by depolymerizing waste polyurethane |
| CN112074555A (en) * | 2018-06-06 | 2020-12-11 | 陶氏环球技术有限责任公司 | Aqueous coating composition |
-
1997
- 1997-09-22 JP JP25723197A patent/JP3957018B2/en not_active Expired - Fee Related
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005075587A1 (en) * | 2004-02-06 | 2005-08-18 | Nippon Paint Co., Ltd. | Water-based intercoating composition and method of forming multilayered coating film |
| WO2005075534A1 (en) * | 2004-02-06 | 2005-08-18 | Adeka Corporation | Aqueous dispersion type polyurethane composition |
| GB2425771A (en) * | 2004-02-06 | 2006-11-08 | Adeka Corp | Aqueous dispersion type polyurethane composition |
| GB2426007A (en) * | 2004-02-06 | 2006-11-15 | Nippon Paint Co Ltd | Water-based intercoating composition and method of forming multilayered coating film |
| GB2426007B (en) * | 2004-02-06 | 2008-07-30 | Nippon Paint Co Ltd | Water-based intermediate coating composition and method of forming multilayered coating film |
| JP2007269832A (en) * | 2006-03-30 | 2007-10-18 | Arakawa Chem Ind Co Ltd | Method of manufacturing polyurethane resin aqueous dispersion |
| CN102618010A (en) * | 2012-03-08 | 2012-08-01 | 广州聚天化工科技有限公司 | Continuous production device and method for regenerating polyol by depolymerizing waste polyurethane |
| CN112074555A (en) * | 2018-06-06 | 2020-12-11 | 陶氏环球技术有限责任公司 | Aqueous coating composition |
Also Published As
| Publication number | Publication date |
|---|---|
| JP3957018B2 (en) | 2007-08-08 |
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