KR20230059385A - Low gloss urethane arcryl hybrid resin composition for textile coating - Google Patents
Low gloss urethane arcryl hybrid resin composition for textile coating Download PDFInfo
- Publication number
- KR20230059385A KR20230059385A KR1020210143514A KR20210143514A KR20230059385A KR 20230059385 A KR20230059385 A KR 20230059385A KR 1020210143514 A KR1020210143514 A KR 1020210143514A KR 20210143514 A KR20210143514 A KR 20210143514A KR 20230059385 A KR20230059385 A KR 20230059385A
- Authority
- KR
- South Korea
- Prior art keywords
- weight
- acrylic monomer
- acrylate
- urethane
- mol
- Prior art date
Links
- 239000004753 textile Substances 0.000 title claims abstract description 23
- 238000000576 coating method Methods 0.000 title claims abstract description 22
- 239000011248 coating agent Substances 0.000 title claims abstract description 21
- 239000011342 resin composition Substances 0.000 title claims abstract description 16
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 title description 4
- 239000000178 monomer Substances 0.000 claims abstract description 61
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 53
- 239000000203 mixture Substances 0.000 claims abstract description 29
- 239000000463 material Substances 0.000 claims abstract description 18
- 229920000642 polymer Polymers 0.000 claims abstract description 18
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 claims abstract description 13
- 229920005862 polyol Polymers 0.000 claims description 21
- -1 ester polyol Chemical class 0.000 claims description 14
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 11
- 150000002513 isocyanates Chemical class 0.000 claims description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 9
- 239000012948 isocyanate Substances 0.000 claims description 9
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 8
- 239000006087 Silane Coupling Agent Substances 0.000 claims description 7
- 125000000129 anionic group Chemical group 0.000 claims description 7
- 125000003277 amino group Chemical group 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 239000003999 initiator Substances 0.000 claims description 6
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 6
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 5
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 claims description 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 4
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 4
- 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 claims description 4
- 239000000835 fiber Substances 0.000 claims description 4
- URDOJQUSEUXVRP-UHFFFAOYSA-N 3-triethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CCO[Si](OCC)(OCC)CCCOC(=O)C(C)=C URDOJQUSEUXVRP-UHFFFAOYSA-N 0.000 claims description 3
- 239000002657 fibrous material Substances 0.000 claims description 3
- 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 claims description 3
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 claims description 2
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 claims description 2
- KBQVDAIIQCXKPI-UHFFFAOYSA-N 3-trimethoxysilylpropyl prop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C=C KBQVDAIIQCXKPI-UHFFFAOYSA-N 0.000 claims description 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims description 2
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 2
- 238000005299 abrasion Methods 0.000 abstract description 8
- 239000006224 matting agent Substances 0.000 abstract description 7
- 230000000704 physical effect Effects 0.000 abstract description 6
- 239000008199 coating composition Substances 0.000 abstract description 2
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 150000003077 polyols Chemical class 0.000 description 14
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 239000004744 fabric Substances 0.000 description 8
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000012975 dibutyltin dilaurate Substances 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 239000011247 coating layer Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 239000000377 silicon dioxide Substances 0.000 description 5
- 230000002194 synthesizing effect Effects 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 description 4
- JVYDLYGCSIHCMR-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)butanoic acid Chemical compound CCC(CO)(CO)C(O)=O JVYDLYGCSIHCMR-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000004970 Chain extender Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000002009 diols Chemical class 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 230000005012 migration Effects 0.000 description 3
- 238000013508 migration Methods 0.000 description 3
- 230000003472 neutralizing effect Effects 0.000 description 3
- 239000004417 polycarbonate Substances 0.000 description 3
- 229920000515 polycarbonate Polymers 0.000 description 3
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 239000005059 1,4-Cyclohexyldiisocyanate Substances 0.000 description 2
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 239000010985 leather Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 229920005749 polyurethane resin Polymers 0.000 description 2
- 235000019394 potassium persulphate Nutrition 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- LGJCFVYMIJLQJO-UHFFFAOYSA-N 1-dodecylperoxydodecane Chemical compound CCCCCCCCCCCCOOCCCCCCCCCCCC LGJCFVYMIJLQJO-UHFFFAOYSA-N 0.000 description 1
- AAMTXHVZOHPPQR-UHFFFAOYSA-N 2-(hydroxymethyl)prop-2-enoic acid Chemical compound OCC(=C)C(O)=O AAMTXHVZOHPPQR-UHFFFAOYSA-N 0.000 description 1
- 229940095095 2-hydroxyethyl acrylate Drugs 0.000 description 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
- IPGXHRDWHJEWBI-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate;4-hydroxy-2-methylidenebutanoic acid Chemical compound OCCOC(=O)C=C.OCCC(=C)C(O)=O IPGXHRDWHJEWBI-UHFFFAOYSA-N 0.000 description 1
- PFYBXKBLFFEPRJ-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN.CO[Si](OC)(OC)CCCN PFYBXKBLFFEPRJ-UHFFFAOYSA-N 0.000 description 1
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 1
- JRQLZCFSWYQHPI-UHFFFAOYSA-N 4,5-dichloro-2-cyclohexyl-1,2-thiazol-3-one Chemical compound O=C1C(Cl)=C(Cl)SN1C1CCCCC1 JRQLZCFSWYQHPI-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- RPXNYQJROASMQT-UHFFFAOYSA-N C(C)C(CC(C(=O)O)=C)CCCC.C(C=C)(=O)OCC(CCCC)CC Chemical compound C(C)C(CC(C(=O)O)=C)CCCC.C(C=C)(=O)OCC(CCCC)CC RPXNYQJROASMQT-UHFFFAOYSA-N 0.000 description 1
- BXAMXIHLXKLNJT-UHFFFAOYSA-N C(C=C)(=O)OCCC[Si](O[Si](C)(C)C)(O[Si](C)(C)C)O[Si](C)(C)C.C(C=C)(=O)OCCC[Si](OC)(OC)OC Chemical compound C(C=C)(=O)OCCC[Si](O[Si](C)(C)C)(O[Si](C)(C)C)O[Si](C)(C)C.C(C=C)(=O)OCCC[Si](OC)(OC)OC BXAMXIHLXKLNJT-UHFFFAOYSA-N 0.000 description 1
- RJQBKQZBJUVSAY-UHFFFAOYSA-N CCO[Si](CCCOC(=O)C(C)=C)(OCC)OCC.CCO[Si](CCCOC(=O)C(C)=C)(OCC)OCC Chemical compound CCO[Si](CCCOC(=O)C(C)=C)(OCC)OCC.CCO[Si](CCCOC(=O)C(C)=C)(OCC)OCC RJQBKQZBJUVSAY-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- IIGAAOXXRKTFAM-UHFFFAOYSA-N N=C=O.N=C=O.CC1=C(C)C(C)=C(C)C(C)=C1C Chemical compound N=C=O.N=C=O.CC1=C(C)C(C)=C(C)C(C)=C1C IIGAAOXXRKTFAM-UHFFFAOYSA-N 0.000 description 1
- 241000233805 Phoenix Species 0.000 description 1
- 229920006311 Urethane elastomer Polymers 0.000 description 1
- KXBFLNPZHXDQLV-UHFFFAOYSA-N [cyclohexyl(diisocyanato)methyl]cyclohexane Chemical compound C1CCCCC1C(N=C=O)(N=C=O)C1CCCCC1 KXBFLNPZHXDQLV-UHFFFAOYSA-N 0.000 description 1
- 230000000996 additive effect Effects 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
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 229960003328 benzoyl peroxide Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- MIOPWDLAZRCMGE-UHFFFAOYSA-N butyl 2-methylprop-2-enoate 2-methylhept-2-enoic acid Chemical compound CCCCOC(=O)C(C)=C.CCCCC=C(C)C(O)=O MIOPWDLAZRCMGE-UHFFFAOYSA-N 0.000 description 1
- VENJJOGQEGHFPI-UHFFFAOYSA-N butyl prop-2-enoate;2-methylidenehexanoic acid Chemical compound CCCCOC(=O)C=C.CCCCC(=C)C(O)=O VENJJOGQEGHFPI-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- WRJBSKQYDASILN-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1.O=C1CCCCC1 WRJBSKQYDASILN-UHFFFAOYSA-N 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- HXDBMSZZSWTGKB-UHFFFAOYSA-N ethyl prop-2-enoate;2-methylidenebutanoic acid Chemical compound CCOC(=O)C=C.CCC(=C)C(O)=O HXDBMSZZSWTGKB-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 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 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- ARYZCSRUUPFYMY-UHFFFAOYSA-N methoxysilane Chemical compound CO[SiH3] ARYZCSRUUPFYMY-UHFFFAOYSA-N 0.000 description 1
- IQSHMXAZFHORGY-UHFFFAOYSA-N methyl prop-2-enoate;2-methylprop-2-enoic acid Chemical compound COC(=O)C=C.CC(=C)C(O)=O IQSHMXAZFHORGY-UHFFFAOYSA-N 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000004945 silicone rubber Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000012756 surface treatment agent Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/06—Polymers provided for in subclass C08G
- C08F290/067—Polyurethanes; Polyureas
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F230/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
- C08F230/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal
- C08F230/08—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/4009—Two or more macromolecular compounds not provided for in one single group of groups C08G18/42 - C08G18/64
- C08G18/4018—Mixtures of compounds of group C08G18/42 with compounds of group C08G18/48
-
- C—CHEMISTRY; METALLURGY
- 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
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
- C09D175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
-
- 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
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
- C09D4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09D159/00 - C09D187/00
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/564—Polyureas, polyurethanes or other polymers having ureide or urethane links; Precondensation products forming them
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Textile Engineering (AREA)
- Polyurethanes Or Polyureas (AREA)
- Paints Or Removers (AREA)
Abstract
Description
본 발명은 소광제의 과량 첨가 없이도 광택을 감소시켜 흐림성을 부여하며 이로 인해 섬유의 심미적 특성과 고급스러움을 향상시킬 뿐만 아니라 표면에너지를 낮춰 내마모성 등의 물성을 향상시킬 수 있도록 하는, 섬유 소재 코팅용 저광택 우레탄 아크릴 하이브리드 수지 조성물에 관한 것이다.The present invention reduces gloss without adding an excessive amount of matting agent to impart haze, thereby improving the aesthetic properties and luxury of the fiber as well as lowering the surface energy to improve physical properties such as abrasion resistance, fiber material coating It relates to a low gloss urethane acrylic hybrid resin composition.
일반적으로 섬유, 필름, 가죽 등의 경우 내구성을 위해 표면 처리제를 사용하고 있으며 원단 표면에 사용되는 프라이머 외에도 기능과 목적에 맞게 수지가 코팅되고, 최외곽에는 주로 수성 폴리우레탄 수지가 사용된다.In general, in the case of textiles, films, leather, etc., surface treatment agents are used for durability, and in addition to primers used on the surface of fabrics, resins are coated according to functions and purposes, and water-based polyurethane resins are mainly used for the outermost part.
한편, 감성 및 터치감을 위해서는 폴리우레탄 성분이 탄성과 기계적 특성이 우수해야하고 심미적으로 고급스러움을 부여하기 위해서는 광택을 줄이면서 흐림도를 증가시킬 수 있어야 한다.On the other hand, for sensitivity and touch, the polyurethane component should have excellent elasticity and mechanical properties, and in order to give aesthetic luxury, it should be able to increase the haze while reducing gloss.
관련 선행기술로써 특허문헌 1에서는 수성 폴리우레탄 수지의 광택을 감소시킬 목적으로 소광제로써 실리카나 왁스 등을 첨가하는 기술을 제안하고 있으나, 소량 사용 시 광택 감소 효과가 없고 과량 사용 시 표면으로 마이그레이션(migration) 되거나 섬유원단, 가죽원단 및 필름등의 기재로부터 부착성이 떨어지는 문제점이 있다. 그리고 분산을 위한 공정이 추가로 요구되고 분산 안정성에 한계가 있어 저장 안정성이 좋지 못하다. As a related prior art, Patent Document 1 proposes a technique of adding silica or wax as a matting agent for the purpose of reducing the gloss of aqueous polyurethane resin, but there is no gloss reduction effect when used in small amounts, and migration to the surface when used in excess ( Migration) or there is a problem of poor adhesion from substrates such as textile fabrics, leather fabrics, and films. In addition, a process for dispersion is additionally required, and storage stability is poor due to limitations in dispersion stability.
이를 해결하기 위하여 최근에는 실리카 표면을 개질하거나 개질된 실리카를 사용함으로써 분산 안정성을 향상시키고 원단과의 부착력을 증가시키는 방안이 제시되었으나, 분산 안정성은 다소 증가하나 물성 증가에는 큰 효과가 없을 뿐 아니라 분산력을 높이기 위한 추가 첨가제가 요구되었다. In order to solve this problem, recently, a method of improving dispersion stability and increasing adhesion with fabric by modifying the silica surface or using modified silica has been proposed. Additional additives were required to increase the
즉, 실리카 등의 소광기능을 갖는 첨가제를 사용하는 경우 광택 감소 및 흐림도 증가로 고급스러움을 부여하는 효과는 있지만 내마모성 등의 물성이 감소하고 분산 및 저장안정성 문제로 사용할 수 있는 양이 한정적이며 과량 사용하기에는 어려운 문제점이 있다.In other words, when using an additive having a quenching function such as silica, it has the effect of imparting luxury by reducing gloss and increasing haze, but physical properties such as abrasion resistance are reduced, and the amount that can be used is limited and excessive due to dispersion and storage stability problems. There are problems with using it.
본 발명은 상기와 같은 문제점을 해결하기 위한 것으로, 우레탄 아크릴레이트 하이브리드 폴리머 및 아크릴 단량체 혼합물을 이용하여 섬유 소재용 코팅 조성물을 제조함으로써 소광제의 과량 첨가 없이도 광택을 감소시켜 흐림성을 부여하며 이로 인해 섬유의 심미적 특성과 고급스러움을 향상시킬 뿐만 아니라 표면에너지를 낮춰 내마모성 등의 물성을 향상시킬 수 있도록 함을 과제로 한다.The present invention is to solve the above problems, by preparing a coating composition for a textile material using a urethane acrylate hybrid polymer and an acrylic monomer mixture to reduce gloss without excessive addition of a matting agent to impart haze, and thereby The task is to improve the aesthetic properties and luxury of textiles as well as to improve physical properties such as abrasion resistance by lowering surface energy.
본 발명은 섬유 소재 코팅용 수지 조성물에 있어서, 우레탄 아크릴레이트 하이브리드 폴리머 65 ~ 70 중량% 및 아크릴 단량체 혼합물 30 ~ 35 중량%를 혼합하고, 상기 혼합물 100 중량부에 대하여 개시제 0.1 ~ 5.0 중량부를 첨가 및 반응시켜 이루어지는 것을 특징으로 하는, 섬유 소재 코팅용 저광택 우레탄 아크릴 하이브리드 수지 조성물을 과제의 해결 수단으로 한다.The present invention is a resin composition for coating a textile material, mixing 65 to 70% by weight of a urethane acrylate hybrid polymer and 30 to 35% by weight of an acrylic monomer mixture, and adding 0.1 to 5.0 parts by weight of an initiator based on 100 parts by weight of the mixture, and A low-gloss urethane-acrylic hybrid resin composition for coating textile materials, characterized in that it is formed by reacting, as a solution to the problem.
여기서, 상기 우레탄 아크릴레이트 하이브리드 폴리머는 에스테르계 폴리올 6 ~ 25 몰%, 에테르계 폴리올 10 ~ 21 몰%, 음이온성 단량체 3 ~ 10 몰% 및 이소시아네이트 19 ~ 66 몰%을 사용하여 NCO/OH 값 1.1 ~ 2.5의 범위에서 프리폴리머를 합성한 후, 상기 합성된 프리폴리머에 잔여 이소시아네이트기와 하이드록실기를 갖는 아크릴 단량체 5 ~ 10 몰%를 반응시키고, 아미노기를 갖는 실란 커플링제 10 ~ 15 몰%를 첨가 및 반응시켜 제조되는 것이 바람직하다.Here, the urethane acrylate hybrid polymer has an NCO / OH value of 1.1 using 6 to 25 mol% of ester polyol, 10 to 21 mol% of ether polyol, 3 to 10 mol% of anionic monomer and 19 to 66 mol% of isocyanate After synthesizing a prepolymer in the range of ~ 2.5, 5 to 10 mol% of an acrylic monomer having a residual isocyanate group and a hydroxyl group is reacted with the synthesized prepolymer, and 10 to 15 mol% of a silane coupling agent having an amino group is added and reacted It is preferable to make it.
그리고, 상기 아크릴 단량체 혼합물은 일반 아크릴 단량체 10 ~ 20 중량%, 분자쇄가 긴 아크릴 단량체 10 ~ 80 중량% 및 실란기 함유 아크릴 단량체 10 ~ 70 중량%로 이루어지는 것이 바람직하다.And, the acrylic monomer mixture is preferably composed of 10 to 20% by weight of a general acrylic monomer, 10 to 80% by weight of an acrylic monomer having a long molecular chain, and 10 to 70% by weight of an acrylic monomer containing a silane group.
한편, 상기 일반 아크릴 단량체는 메틸메타아크릴레이트, 부틸아크릴레이트, 에틸아크릴레이트, 메틸아크릴레이트, 부틸메타크릴레이트 또는 2-에틸헥실아크릴레이트 중에서 단독 또는 병용하여 사용하고, 상기 분자쇄가 긴 아크릴 단량체는 라우릴(메타)아크릴레이트, 팔리틸(메타)아크릴레이트 또는 스테아릴(메타)아크릴레이트 중에서 단독 또는 병용하여 사용하며, 상기 실란기 함유 아크릴 단량체는 3-(메타크릴로일옥시)프로필트라이메톡시실란, 3-(메타크릴로일옥시)프로필트라이에톡시실란 또는 3-아크릴로옥시프로필트라이메톡시실란 중에서 단독 또는 병용하여 사용하는 것이 바람직하다.On the other hand, the general acrylic monomer is used alone or in combination among methyl methacrylate, butyl acrylate, ethyl acrylate, methyl acrylate, butyl methacrylate or 2-ethylhexyl acrylate, and the long molecular chain acrylic monomer is used alone or in combination in lauryl (meth) acrylate, palytyl (meth) acrylate or stearyl (meth) acrylate, and the silane group-containing acrylic monomer is 3- (methacryloyloxy) propyltri Among methoxysilane, 3-(methacryloyloxy)propyltriethoxysilane, or 3-acrylooxypropyltrimethoxysilane, it is preferable to use alone or in combination.
한편, 상기 아크릴 단량체 혼합물은 Tg가 0 ~ 40℃인 것이 바람직하다.Meanwhile, the acrylic monomer mixture preferably has a Tg of 0 to 40°C.
본 발명은 소광제의 과량 첨가 없이도 광택을 감소시키고 흐림도(haze)를 높일 수 있어 심미적인 특성이 우수하여 고급제품에 적용 가능하며, 아울러, 종래기술과 같이 소광제로써 실리카나 불소 등을 사용하지 않아 저장안정성을 개선하면서도 마이그레이션 현상을 방지할 수 있고 또한 가격이 저렴하며 원료 수급, 사용량 및 환경규제 등에 제한을 받지 않을 뿐만 아니라, 표면에너지를 낮춰 외부 스크래치에 대한 내마모성 등의 물성을 향상시킬 수 있는 효과가 있으며, 이를 바탕으로 구현하고자 하는 용도, 기능 및 효과를 고려하여 각각의 폴리머를 최적으로 용이하게 혼용하여 사용할 수 있는 효과가 있다.The present invention can reduce gloss and increase haze without excessive addition of a matting agent, so it has excellent aesthetic properties and can be applied to high-end products. In addition, as in the prior art, silica or fluorine is used as a matting agent. It is possible to prevent migration while improving storage stability, and is inexpensive, and is not limited by raw material supply and demand, usage, and environmental regulations, and can improve physical properties such as abrasion resistance against external scratches by lowering surface energy. Based on this, there is an effect that each polymer can be optimally and easily mixed and used in consideration of the purpose, function, and effect to be realized.
상기의 효과를 달성하기 위한 본 발명은 섬유 소재 코팅용 저광택 우레탄 아크릴 하이브리드 수지 조성물에 관한 것으로서, 본 발명의 기술적 구성을 이해하는데 필요한 부분만이 설명되며 그 이외 부분의 설명은 본 발명의 요지를 흩트리지 않도록 생략될 것이라는 것을 유의하여야 한다.The present invention for achieving the above effect relates to a low-gloss urethane-acrylic hybrid resin composition for coating textile materials, and only parts necessary for understanding the technical configuration of the present invention are described, and other parts of the description scatter the gist of the present invention. It should be noted that it will be omitted to avoid loss.
이하, 본 발명에 따른 섬유 소재 코팅용 저광택 우레탄 아크릴 하이브리드(urethane arcryl hybrid) 수지 조성물을 상세히 설명하면 다음과 같다.Hereinafter, a low gloss urethane acrylic hybrid resin composition for coating a fiber material according to the present invention will be described in detail.
본 발명에 따른 섬유 소재 코팅용 저광택 우레탄 아크릴 하이브리드 수지 조성물은 우레탄 아크릴레이트 하이브리드 폴리머(urethane arcryl hybrid polymer) 65 ~ 70 중량% 및 아크릴(arcryl) 단량체 혼합물 30 ~ 35 중량%를 혼합하고, 상기 혼합물 100 중량부에 대하여 개시제 0.1 ~ 5.0 중량부를 첨가 및 반응시켜 이루어지는 것을 특징으로 한다.The low-gloss urethane-acrylic hybrid resin composition for coating textile materials according to the present invention is a mixture of 65 to 70% by weight of a urethane acrylate hybrid polymer and 30 to 35% by weight of an acrylic monomer mixture, and 100% by weight of the mixture It is characterized by adding and reacting 0.1 to 5.0 parts by weight of an initiator based on parts by weight.
여기서, 상기 각 조성물의 함량이 상기 범위를 벗어날 경우 우레탄 아크릴 하이브리드 수지가 제대로 제조되지 못할 우려가 있다.Here, when the content of each composition is out of the above range, there is a concern that the urethane-acrylic hybrid resin may not be properly prepared.
상기 우레탄 아크릴레이트 하이브리드 폴리머는 에스테르(ester)계 폴리올(polyol) 6 ~ 25 몰%, 에테르(ether)계 폴리올 10 ~ 21 몰%, 음이온성 단량체 3 ~ 10 몰% 및 이소시아네이트(isocyanate) 19 ~ 66 몰%을 사용하여 NCO/OH 값 1.1 ~ 2.5의 범위에서 프리폴리머(prepolymer)를 합성한 후, 상기 합성된 프리폴리머에 잔여 이소시아네이트기(isocyanate group)와 하이드록실기(hydroxyl group)를 갖는 아크릴 단량체 5 ~ 10 몰%를 반응시키고, 아미노기(ammio group)를 갖는 실란 커플링제(silane coupling agent) 10 ~ 15 몰%를 첨가 및 반응시켜 제조된다.The urethane acrylate hybrid polymer contains 6 to 25 mol% of ester polyol, 10 to 21 mol% of ether polyol, 3 to 10 mol% of anionic monomer, and 19 to 66 isocyanate. After synthesizing a prepolymer in the range of NCO / OH value of 1.1 to 2.5 using mol%, an acrylic monomer having a residual isocyanate group and a hydroxyl group in the synthesized prepolymer 5 to It is prepared by reacting 10 mol% and adding and reacting 10 to 15 mol% of a silane coupling agent having an amino group.
여기서, 상기 우레탄 아크릴레이트 하이브리드 폴리머를 이루는 각 물질의 몰비 및 NCO/OH 값이 상기 범위를 벗어날 경우 코팅층의 유연성 및 기계적 물성이 저하될 우려가 있다.Here, when the molar ratio and NCO/OH value of each material constituting the urethane acrylate hybrid polymer are out of the above range, there is a concern that flexibility and mechanical properties of the coating layer may be deteriorated.
한편, 상기 에스테르계 폴리올은 폴리카보네이트 디올(polycarbonate diol) 또는 부틸렌 글리콜(butylene glycol)과 아크릴산(Acrylic Acid)의 중합체 중에서 단독 또는 병용하여 사용할 수 있고, 에테르계 폴리올은 폴리테트라메틸렌 글리콜(Polytetramethylene glycol) 또는 폴리프로필렌글리콜(polypropylene glycol)을 사용할 수 있으며, 상기 음이온성 단량체는 DMPA(Dimethylol propionic acid), DMBA(Dimethylol butyric acid) 중에서 단독 또는 병용하여 사용할 수 있으며, 상기 이소시아네이트는 HDI(Hexamethylene diisocyanate), IPDI(Isophorone Diisocyanate), H12MDI(dicyclohexylmethane diisocyanate), TMXDI(Tetramethylxylene Diisocyanate), NDI(naphthalene-1,5-diisocyanate), XDI(m-xylene diisocyanate), CHDI(1,4-cyclohexyl diisocyanate) 또는 DDI(Diphenylmethane diisocyanate)의 둘 이상의 이성질체, 다이머, 트라이머, 및 혼합물 또는 조합물를 적용할 수 있고, 상기 잔여 이소시아네이트기와 반응할 수 있는 하이드록실기를 갖는 아크릴 단량체는 2-하이드록시에틸아크릴레이트(2-hydroxyethylacrylate) 또는 2-하이드록시메틸아크릴레이트(2-hydroxymethylacrylate) 등을 사용할 수 있고, 상기 아미노기를 갖는 실란 커플링제는 3-아미노프로필트라이에톡시실란(3-aminopropyltriethoxysilane) 또는 3-아미노프로필트라이메톡시실란(3-aminopropyltrimethoxysilane)을 사용할수 있으나, 반드시 여기에 한정되는 것은 아니고 이미 공지된 다양한 종류의 폴리올, 음이온성 단량체, 아크릴 단량체, 실란 커플링제 및 이소시아네이트의 사용이 가능하다Meanwhile, the ester-based polyol may be used alone or in combination among polymers of polycarbonate diol or butylene glycol and acrylic acid, and the ether-based polyol may be polytetramethylene glycol ) or polypropylene glycol may be used, and the anionic monomer may be used alone or in combination among DMPA (Dimethylol propionic acid) and DMBA (Dimethylol butyric acid), and the isocyanate may be HDI (Hexamethylene diisocyanate), Isophorone diisocyanate (IPDI), dicyclohexylmethane diisocyanate (H12MDI), tetramethylxylene diisocyanate (TMXDI), naphthalene-1,5-diisocyanate (NDI), m-xylene diisocyanate (XDI), 1,4-cyclohexyl diisocyanate (CHDI), or diphenylmethane (DDI) diisocyanate) can be applied to two or more isomers, dimers, trimers, and mixtures or combinations, and the acrylic monomer having a hydroxyl group capable of reacting with the residual isocyanate group is 2-hydroxyethylacrylate (2-hydroxyethylacrylate) Alternatively, 2-hydroxymethylacrylate may be used, and the silane coupling agent having an amino group is 3-aminopropyltriethoxysilane or 3-aminopropyltrimethoxysilane ( 3-aminopropyltrimethoxysilane) can be used, but it is not necessarily limited thereto, and various types of polyols, anionic monomers, acrylic monomers, silane coupling agents, and isocyanates already known can be used.
아울러, 상기 아크릴 단량체 혼합물은 일반 아크릴 단량체 10 ~ 20 중량%, 일반 아크릴 단량체보다 분자쇄가 긴 아크릴 단량체 10 ~ 80 중량% 및 실란기(silane group) 함유 아크릴 단량체 10 ~ 70 중량%로 이루어진다.In addition, the acrylic monomer mixture is composed of 10 to 20% by weight of a general acrylic monomer, 10 to 80% by weight of an acrylic monomer having a molecular chain longer than that of a general acrylic monomer, and 10 to 70% by weight of an acrylic monomer containing a silane group.
여기서, 상기 각 단량체의 종류 및 함량이 상기 범위를 벗어날 경우 아크릴 단량체 혼합물의 특성(물성보강, 방수성 등)이 발현되지 못할 우려가 있다.Here, if the type and content of each monomer is out of the above range, there is a concern that the properties (reinforcement of physical properties, waterproofness, etc.) of the acrylic monomer mixture may not be expressed.
한편, 상기 일반 아크릴 단량체는 메틸메타아크릴레이트(Methyl MetAcrylate), 부틸아크릴레이트(Butyl Acrylate), 에틸아크릴레이트(ethyl acryalte), 메틸아크릴레이트(methyl acrylate), 부틸메타크릴레이트(butyl methacrylate) 또는 2-에틸헥실아크릴레이트(2-Ethyl Hexyl Acrylate) 중에서 단독 또는 병용하여 사용하며, 상기 분자쇄가 긴 아크릴 단량체는 아래 [화학식 1]과 같은 구조의 R2의 탄소수가 12개 이상인 단량체로, 예를 들면, 라우릴(메타)아크릴레이트(lauryl(metha)acrylate), 팔리틸(메타)아크릴레이트(phalityl(metha)acrylate) 또는 스테아릴(메타)아크릴레이트(stearyl(metha)acrylate) 중에서 단독 또는 병용하여 사용하며, 상기 실란기 함유 아크릴 단량체는 3-(메타크릴로일옥시)프로필트라이메톡시실란 (3-methacryloxypropyltrimethoxysilane), 3-(메타크릴로일옥시)프로필트라이에톡시실란(3-methacryloxypropyltriethoxysilane) 또는 3-아크릴로옥시프로필트라이메톡시실란(3-acryloxypropyltristrimethylsiloxysilane) 중에서 단독 또는 병용하여 사용할 수 있지만, 반드시 여기에 한정되는 것은 아니고 각 단량체 종류별 이미 공지된 다양한 종류의 단량체 적용이 가능하다.On the other hand, the general acrylic monomer is methyl methacrylate (Methyl MetAcrylate), butyl acrylate (Butyl Acrylate), ethyl acrylate (ethyl acrylate), methyl acrylate (methyl acrylate), butyl methacrylate (butyl methacrylate) or 2 -Ethylhexyl acrylate (2-Ethyl Hexyl Acrylate) is used alone or in combination, and the long molecular chain acrylic monomer is a monomer having 12 or more carbon atoms in R 2 of the structure shown in [Formula 1] below, for example For example, lauryl(metha)acrylate, phallyl(metha)acrylate, or stearyl(meth)acrylate, alone or in combination and used, and the silane group-containing acrylic monomer is 3-(methacryloxypropyltrimethoxysilane), 3-(methacryloyloxy)propyltriethoxysilane (3-methacryloxypropyltriethoxysilane) Or 3-acryloxypropyltrimethoxysilane (3-acryloxypropyltristrimethylsiloxysilane) can be used alone or in combination, but is not necessarily limited thereto, and various types of monomers already known for each monomer type can be applied.
[화학식 1][Formula 1]
(R1은 수소 또는 메틸기, R2는 탄소수 12 이상의 1가 탄화수소기)(R 1 is hydrogen or methyl group, R 2 is a monovalent hydrocarbon group having 12 or more carbon atoms)
한편, 상기 아크릴 단량체 혼합물은 Tg(glass transitiontemperature)가 0 ~ 40℃인 것을 사용하며, Tg가 0℃ 미만일 경우 택(tack)이 생성되는 등 불량이 발생할 우려가 있고, 40℃를 초과할 경우 크랙(crack) 등이 생길 우려가 있다.On the other hand, the acrylic monomer mixture uses a Tg (glass transition temperature) of 0 to 40 ° C. If the Tg is less than 0 ° C, there is a possibility of defects such as tack generation, and if the Tg exceeds 40 ° C, cracks may occur. (crack) may occur.
아울러, 상기 개시제의 경우 포타슘퍼옥시디설페이트(potassiumperoxidisulfate), 암모늄퍼옥시디설페이트(ammoniumperoxidisulfate), 디벤조일퍼옥사이드(dibenzoylperoxide), 라우릴퍼옥사이드(laurylperoxid), 2,2-아조비스이소부틸로니트릴(2,2-azobisisobutylonitrile) 또는 벤조일퍼옥사이드(benzoylperoxide) 중에서 단독 또는 병용하여 사용하며, 본 발명에서는 상기 조성 이외에도 중화제(예를 들면, TEA(triethylene diamine), TMA(trimethylene diamine), TPA(tripropyl diamine)), 촉매(예를 들면, DBTDL(dibutyltin dilaurate), 쇄연장제(예를 들면, DEG(diethylene glycol)), 경화제, 촉매, 촉진제 등의 첨가제와 염료, 안료 그리고 기타 도막형성 요소로서 톨루엔, 자일렌(Xylene), 메틸에틸케톤(Methyl Ethyl Ketone) 및 사이클로헥산온(Cyclohexanone) 등의 용제 혹은 희석제를 포함할 수 있고, 또한 필요에 따라 카올린, 탈크, 실리카, 칼슘 카보네이트, 마이카, 이산화티탄, 알루미나, 실리콘 고무 파우더, 우레탄 고무 파우더, 실리콘 수지 파우더 또는 아크릴계 파우더 등과 같은 충전제나 조색제, 침강방지제, 분산제, 레벨링제, 소광제, 소포제, 안료, 무기 분체, 증점제, 계면활성제, 유화제, 자외선 흡수제 등 이미 공지된 다양한 첨가제의 적용이 가능하다.In addition, in the case of the initiator, potassium peroxidisulfate, ammoniumperoxidisulfate, dibenzoylperoxide, laurylperoxide, 2,2-azobisisobutylonitrile (2 ,2-azobisisobutylonitrile) or benzoylperoxide, used alone or in combination, and in the present invention, in addition to the above composition, a neutralizing agent (eg, TEA (triethylene diamine), TMA (trimethylene diamine), TPA (tripropyl diamine)) , additives such as catalysts (e.g., dibutyltin dilaurate (DBTDL), chain extenders (e.g., diethylene glycol (DEG)), curing agents, catalysts, and promoters), as well as toluene and xylene as dyes, pigments, and other film-forming elements (Xylene), methyl ethyl ketone (Methyl Ethyl Ketone), and cyclohexanone (Cyclohexanone) may include solvents or diluents, and also, if necessary, kaolin, talc, silica, calcium carbonate, mica, titanium dioxide, alumina, Fillers such as silicone rubber powder, urethane rubber powder, silicone resin powder or acrylic powder, coloring agent, anti-settling agent, dispersing agent, leveling agent, matting agent, antifoaming agent, pigment, inorganic powder, thickener, surfactant, emulsifier, ultraviolet absorber, etc. are already known. Various additives can be applied.
이하, 본 발명을 실시예에 의거하여 더욱 구체적으로 설명하겠는 바, 본 발명이 다음 실시예에 의해 한정되는 것을 아니다.Hereinafter, the present invention will be described in more detail based on examples, but the present invention is not limited by the following examples.
1. 섬유 소재 코팅용 저광택 우레탄 아크릴 하이브리드 수지의 제조1. Preparation of low-gloss urethane-acrylic hybrid resin for coating textile materials
(실시예 1)(Example 1)
교반기, 환류 냉각기, 질소 주입구가 장착된 4구 반응기(2L)에 수분이 제거된 에스테르계 폴리올(폴리카보네이트 디올) 25 몰%, 에테르계 폴리올(폴리프로필렌글리콜) 21 몰%, 음이온성 단량체(DMPA와 DMBA 1:1 중량비 혼합) 10 몰%를 첨가한 후 80℃에서 혼합하고, 촉매(DBTDL, 폴리올 100 중량부 기준 0.001 중량부)를 첨가하고, 여기에 이소시아네이트(HDI) 19 몰%을 투입하여 NCO/OH 값 2.5의 범위에서 80℃, 120분간 합성하여 프리폴리머를 제조하였다. 그리고 50℃로 냉각시킨 후 중화제(TEA)를 첨가하여 중화반응시키고, 여기에 잔여 이소시아네이트기와 하이드록실기를 갖는 아크릴 단량체( 2-하이드록시에틸아크릴레이트) 10 몰%와 아미노기를 갖는 실란 커플링제(3-아미노프로필트라이에톡시실란) 15 몰%를 차례대로 반응기에 투입한 후 쇄연장 반응 후 반응을 종결시키고, 증류수를 첨가하면서 고속교반기로 30분 이상 강하게 교반시켜 우레탄 아크릴레이트 하이브리드 폴리머를 제조하였다.25 mol% of ester-based polyol (polycarbonate diol), 21 mol% of ether-based polyol (polypropylene glycol), anionic monomer (DMPA and DMBA in a 1:1 weight ratio) after adding 10 mol%, mixing at 80 ° C, adding a catalyst (DBTDL, 0.001 part by weight based on 100 parts by weight of polyol), and adding 19 mol% of isocyanate (HDI) thereto. A prepolymer was prepared by synthesizing at 80 ° C. for 120 minutes in the range of NCO / OH value of 2.5. And after cooling to 50 ° C., a neutralizing agent (TEA) was added to neutralize, and 10 mol% of an acrylic monomer (2-hydroxyethyl acrylate) having a residual isocyanate group and a hydroxyl group and a silane coupling agent having an amino group ( 3-aminopropyltriethoxysilane) 15 mol% was sequentially introduced into the reactor, the reaction was terminated after the chain extension reaction, and distilled water was added while vigorously stirring for 30 minutes or more with a high-speed stirrer to prepare a urethane acrylate hybrid polymer. .
그리고, 상기 제조된 우레탄 아크릴레이트 하이브리드 폴리머 65 중량% 및 아크릴 단량체 혼합물 35 중량%를 혼합하고, 상기 혼합물 100 중량부에 대하여 개시제(포타슘퍼옥시디설페이트) 5.0 중량부를 첨가하고 60℃에서 6시간 반응시켜 섬유 소재 코팅용 저광택 우레탄 아크릴 하이브리드 수지를 제조하였다.In addition, 65% by weight of the prepared urethane acrylate hybrid polymer and 35% by weight of the acrylic monomer mixture were mixed, and 5.0 parts by weight of an initiator (potassium peroxydisulfate) was added to 100 parts by weight of the mixture and reacted at 60 ° C. for 6 hours A low-gloss urethane-acrylic hybrid resin for coating textile materials was prepared.
여기서, 상기 아크릴 단량체 혼합물(Tg 40℃)은 일반 아크릴 단량체(부틸아크릴레이트) 10 중량%, 분자쇄가 긴 아크릴 단량체(라우릴(메타)아크릴레이트) 80 중량% 및 실란기 함유 아크릴 단량체(3-(메타크릴로일옥시)프로필트라이에톡시실란) 10 중량%로 이루어지는 것을 사용하였다.Here, the acrylic monomer mixture (Tg 40 ° C.) is 10% by weight of a general acrylic monomer (butyl acrylate), 80% by weight of an acrylic monomer with a long molecular chain (lauryl (meth) acrylate), and an acrylic monomer containing a silane group (3 - (methacryloyloxy) propyltriethoxysilane) was used consisting of 10% by weight.
(실시예 2)(Example 2)
교반기, 환류 냉각기, 질소 주입구가 장착된 4구 반응기(2L)에 수분이 제거된 에스테르계 폴리올(폴리카보네이트 디올) 6 몰%, 에테르계 폴리올(폴리테트라메틸렌 글리콜) 10 몰%, 음이온성 단량체(DMPA와 DMBA 1:1 중량비 혼합) 3 몰%를 첨가한 후 80℃에서 혼합하고, 촉매(DBTDL, 폴리올 100 중량부 기준 0.001 중량부)를 첨가하고, 여기에 이소시아네이트(HDI) 66 몰%을 투입하여 NCO/OH 값 1.1의 범위에서 80℃, 120분간 합성하여 프리폴리머를 제조하였다. 그리고 50℃로 냉각시킨 후 중화제(TEA)를 첨가하여 중화반응시키고, 여기에 잔여 이소시아네이트기와 하이드록실기를 갖는 아크릴 단량체( 2-하이드록시메틸아크릴레이트) 5 몰%와 아미노기를 갖는 실란 커플링제(3-아미노프로필트라이메톡시실란) 10 몰%를 차례대로 반응기에 투입한 후 쇄연장 반응 후 반응을 종결시키고, 증류수를 첨가하면서 고속교반기로 30분 이상 강하게 교반시켜 우레탄 아크릴레이트 하이브리드 폴리머를 제조하였다.In a four-necked reactor (2L) equipped with an agitator, reflux condenser, and nitrogen inlet, 6 mol% of ester-based polyol (polycarbonate diol) from which moisture was removed, 10 mol% of ether-based polyol (polytetramethylene glycol), anionic monomer ( After adding 3 mol% of DMPA and DMBA in a 1:1 weight ratio), mixing at 80°C, adding a catalyst (DBTDL, 0.001 part by weight based on 100 parts by weight of polyol), and adding 66 mol% of isocyanate (HDI) thereto and synthesized at 80 ° C. for 120 minutes in the range of NCO / OH value of 1.1 to prepare a prepolymer. And after cooling to 50 ° C., a neutralizing agent (TEA) was added to neutralize, and 5 mol% of an acrylic monomer (2-hydroxymethyl acrylate) having a residual isocyanate group and a hydroxyl group and a silane coupling agent having an amino group ( 10 mol% of 3-aminopropyltrimethoxysilane) was sequentially introduced into the reactor, the reaction was terminated after the chain extension reaction, and distilled water was added while vigorously stirring for 30 minutes or more with a high-speed stirrer to prepare a urethane acrylate hybrid polymer. .
그리고, 상기 제조된 우레탄 아크릴레이트 하이브리드 폴리머 70 중량% 및 아크릴 단량체 혼합물 30 중량%를 혼합하고, 상기 혼합물 100 중량부에 대하여 개시제(포타슘퍼옥시디설페이트) 0.1 중량부를 첨가하고 60℃에서 6시간 반응시켜 섬유 소재 코팅용 저광택 우레탄 아크릴 하이브리드 수지를 제조하였다.In addition, 70% by weight of the prepared urethane acrylate hybrid polymer and 30% by weight of the acrylic monomer mixture were mixed, and 0.1 part by weight of an initiator (potassium peroxydisulfate) was added to 100 parts by weight of the mixture and reacted at 60 ° C. for 6 hours A low-gloss urethane-acrylic hybrid resin for coating textile materials was prepared.
여기서, 상기 아크릴 단량체 혼합물(Tg 0℃)은 일반 아크릴 단량체(메틸메타아크릴레이트) 20 중량%, 분자쇄가 긴 아크릴 단량체(팔리틸(메타)아크릴레이트) 10 중량% 및 실란기 함유 아크릴 단량체(3-(메타크릴로일옥시)프로필트라이메톡시실란) 70 중량%로 이루어지는 것을 사용하였다.Here, the acrylic monomer mixture (Tg 0 ° C) is 20% by weight of a general acrylic monomer (methyl methacrylate), 10% by weight of an acrylic monomer with a long molecular chain (palytyl (meth) acrylate), and an acrylic monomer containing a silane group ( 3- (methacryloyloxy) propyltrimethoxysilane) was used consisting of 70% by weight.
(비교예 1)(Comparative Example 1)
교반기, 환류 냉각기, 질소 주입구가 장착된 4구 반응기(2L)에 수분이 제거된 폴리올인 폴리테트라메틸렌 글리콜 29 몰%, 불소기 함유 폴리올(fluorine polyol) 1 몰% 및 용매(메틸에틸케톤, 폴리올 100 중량부 기준 235 중량부)를 투입하고 50℃로 승온한 후, 촉매(DBTDL, 폴리올 100 중량부 기준 0.001 중량부)를 첨가하여 80℃에서 혼합하고, 여기에 이소시아네이트(MDI) 55 몰%를 투입(NCO/OH 비 1.1)하고 60℃에서 60분간 합성하여 프리폴리머를 제조하였다. 그리고 상기 제조된 프리폴리머에 쇄연장제(DEG) 15 몰%를 첨가하고 90℃에서 NCO 피크가 소멸될때 까지 300분간 합성하여 제조한 우레탄 폴리머를 사용하였다.29 mol% of polytetramethylene glycol, 1 mol% of fluorine polyol, and solvent (methyl ethyl ketone, polyol) After adding 235 parts by weight based on 100 parts by weight) and raising the temperature to 50 ° C, a catalyst (DBTDL, 0.001 part by weight based on 100 parts by weight of polyol) was added and mixed at 80 ° C, and 55 mol% of isocyanate (MDI) was added thereto. A prepolymer was prepared by adding (NCO/OH ratio 1.1) and synthesizing at 60° C. for 60 minutes. In addition, a urethane polymer prepared by adding 15 mol% of a chain extender (DEG) to the prepared prepolymer and synthesizing at 90 ° C. for 300 minutes until the NCO peak disappeared was used.
(비교예 2)(Comparative Example 2)
교반기, 환류 냉각기, 질소 주입구가 장착된 4구 반응기(2L)에 수분이 제거된 폴리올인 폴리테트라메틸렌 글리콜 30 몰% 및 용매(메틸에틸케톤, 폴리올 100 중량부 기준 235 중량부)를 투입하고 50℃로 승온한 후, 촉매(DBTDL, 폴리올 100 중량부 기준 0.001 중량부)를 첨가하여 80℃에서 혼합하고, 여기에 이소시아네이트(MDI) 55 몰%를 투입(NCO/OH 비 1.1)하고 60℃에서 60분간 합성하여 프리폴리머를 제조하였다. 그리고 상기 제조된 프리폴리머에 쇄연장제 15 몰%를 첨가하고 90℃에서 NCO 피크가 소멸될때 까지 300분간 합성하여 우레탄 폴리머를 제조하였다.30 mol% of polytetramethylene glycol, a polyol from which moisture has been removed, and a solvent (methyl ethyl ketone, 235 parts by weight based on 100 parts by weight of polyol) were added to a four-necked reactor (2L) equipped with an agitator, reflux condenser, and nitrogen inlet, and 50 After raising the temperature to ° C, a catalyst (DBTDL, 0.001 parts by weight based on 100 parts by weight of polyol) was added and mixed at 80 ° C, 55 mol% of isocyanate (MDI) was added thereto (NCO / OH ratio 1.1), and at 60 ° C A prepolymer was prepared by synthesis for 60 minutes. In addition, 15 mol% of a chain extender was added to the prepared prepolymer and synthesized at 90° C. for 300 minutes until the NCO peak disappeared to prepare a urethane polymer.
또한, 부틸아크릴레이트 30 중량%, 메틸메타크릴레이트 60 중량% 및 아크릴릭에시드 10 중량%를 혼합 및 반응시켜 아크릴 단량체 혼합물(Tg -20℃)을 제조하였다.In addition, 30% by weight of butyl acrylate, 60% by weight of methyl methacrylate and 10% by weight of acrylic acid were mixed and reacted to prepare an acrylic monomer mixture (Tg -20 ° C).
그리고, 상기 제조된 우레탄 폴리머 50 중량% 및 아크릴 단량체 혼합물 50 중량%를 혼합하여 제조하였다.And, it was prepared by mixing 50% by weight of the prepared urethane polymer and 50% by weight of the acrylic monomer mixture.
2. 섬유 소재 코팅용 저광택 우레탄 아크릴 하이브리드 수지의 평가2. Evaluation of low-gloss urethane-acrylic hybrid resin for coating textile materials
상기 실시예 및 비교예에 대해 광택, 접촉각 및 내마모성을 아래와 같이 평가하였고, 그 결과는 그 결과는 아래 [표 1]에 나타내었다.Gloss, contact angle and abrasion resistance were evaluated as follows for the above Examples and Comparative Examples, and the results are shown in [Table 1] below.
(1) 광택(1) gloss
섬유 원단에 실시예와 비교예에 따른 조성물을 도포하여 코팅층을 형성시키고 24시간 동안 상온에서 건조한 후, 광택계(60o, Gloss)로 광택을 측정하였다. After coating the composition according to Examples and Comparative Examples on a textile fabric to form a coating layer and drying at room temperature for 24 hours, gloss was measured with a gloss meter (60 o , Gloss).
(2) 접촉각(2) contact angle
섬유 원단에 실시예와 비교예에 따른 조성물을 도포하여 코팅층을 형성시키고 24시간 동안 상온에서 건조한 후, 그 표면에 스포이드(spuit)를 이용하여 물방울을 떨어뜨리고, 접촉각 측정기(Phoenix 300, S대)를 이용하여 물 접촉각을 측정하였다.After coating the composition according to Examples and Comparative Examples on a textile fabric to form a coating layer and drying at room temperature for 24 hours, water droplets were dropped on the surface using a spuit, and contact angle measuring device (Phoenix 300, S unit) The water contact angle was measured using
(3) 내마모성(3) Wear resistance
섬유 원단에 코팅층을 형성시키고, 마모자로 H-22를 사용하여 500g의 하중으로 코팅층이 벗겨질 때까지 측정하였으며 사이클 횟수를 측정하였다. A coating layer was formed on the fiber fabric, and measured until the coating layer was peeled off under a load of 500 g using H-22 as a wearer, and the number of cycles was measured.
상기 [표 1]에서와 같이, 본 발명의 실시예는 비교예에 비하여 광택이 낮아 섬유에 고급스러움을 증가시킬 수 있고, 접촉각이 높은 것을 고려할 때, 표면에너지가 낮아 방수 성능 및 내마모성 등의 물성이 우수함을 알 수 있다.As shown in [Table 1], the embodiment of the present invention has a lower gloss compared to the comparative example, which can increase the luxury of the fiber, and considering that the contact angle is high, the surface energy is low, such as waterproof performance and abrasion resistance. You can see this excellence.
상술한 바와 같이, 본 발명에 따른 섬유 소재 코팅용 저광택 우레탄 아크릴 하이브리드 수지 조성물은 상기의 바람직한 실시 예를 통해 설명하고, 그 우수성을 확인하였지만 해당 기술 분야의 당업자라면 하기의 특허 청구 범위에 기재된 본 발명의 사상 및 영역으로부터 벗어나지 않는 범위 내에서 본 발명을 다양하게 수정 및 변경시킬 수 있음을 이해할 수 있을 것이다.As described above, the low-gloss urethane-acrylic hybrid resin composition for coating textile materials according to the present invention has been described through the above preferred examples and its excellence has been confirmed, but those skilled in the art will find the present invention described in the following claims It will be understood that the present invention can be variously modified and changed without departing from the spirit and scope of the above.
Claims (5)
우레탄 아크릴레이트 하이브리드 폴리머 65 ~ 70 중량% 및 아크릴 단량체 혼합물 30 ~ 35 중량%를 혼합하고, 상기 혼합물 100 중량부에 대하여 개시제 0.1 ~ 5.0 중량부를 첨가 및 반응시켜 이루어지는 것을 특징으로 하는, 섬유 소재 코팅용 저광택 우레탄 아크릴 하이브리드 수지 조성물.
In the resin composition for coating a fiber material,
65 to 70% by weight of a urethane acrylate hybrid polymer and 30 to 35% by weight of an acrylic monomer mixture are mixed, and 0.1 to 5.0 parts by weight of an initiator is added and reacted with respect to 100 parts by weight of the mixture. A low gloss urethane acrylic hybrid resin composition.
상기 우레탄 아크릴레이트 하이브리드 폴리머는,
에스테르계 폴리올 6 ~ 25 몰%, 에테르계 폴리올 10 ~ 21 몰%, 음이온성 단량체 3 ~ 10 몰% 및 이소시아네이트 19 ~ 66 몰%을 사용하여 NCO/OH 값 1.1 ~ 2.5의 범위에서 프리폴리머를 합성한 후, 상기 합성된 프리폴리머에 잔여 이소시아네이트기와 하이드록실기를 갖는 아크릴 단량체 5 ~ 10 몰%를 반응시키고, 아미노기를 갖는 실란 커플링제 10 ~ 15 몰%를 첨가 및 반응시켜 제조되는 것을 특징으로 하는, 섬유 소재 코팅용 저광택 우레탄 아크릴 하이브리드 수지 조성물.
According to claim 1,
The urethane acrylate hybrid polymer,
A prepolymer was synthesized in the range of NCO/OH value of 1.1 to 2.5 using 6 to 25 mol% of ester polyol, 10 to 21 mol% of ether polyol, 3 to 10 mol% of anionic monomer, and 19 to 66 mol% of isocyanate. After that, the synthesized prepolymer is reacted with 5 to 10 mol% of an acrylic monomer having a residual isocyanate group and a hydroxyl group, and 10 to 15 mol% of a silane coupling agent having an amino group is added and reacted to produce a fiber, characterized in that A low-gloss urethane-acrylic hybrid resin composition for material coating.
상기 아크릴 단량체 혼합물은,
일반 아크릴 단량체 10 ~ 20 중량%, 분자쇄가 긴 아크릴 단량체 10 ~ 80 중량% 및 실란기 함유 아크릴 단량체 10 ~ 70 중량%로 이루어지는 것을 특징으로 하는, 섬유 소재 코팅용 저광택 우레탄 아크릴 하이브리드 수지 조성물.
According to claim 1,
The acrylic monomer mixture,
A low-gloss urethane-acrylic hybrid resin composition for coating textile materials, characterized in that it consists of 10 to 20% by weight of a general acrylic monomer, 10 to 80% by weight of an acrylic monomer having a long molecular chain, and 10 to 70% by weight of an acrylic monomer containing a silane group.
상기 일반 아크릴 단량체는, 메틸메타아크릴레이트, 부틸아크릴레이트, 에틸아크릴레이트, 메틸아크릴레이트, 부틸메타크릴레이트 또는 2-에틸헥실아크릴레이트 중에서 단독 또는 병용하여 사용하고,
상기 분자쇄가 긴 아크릴 단량체는, 라우릴(메타)아크릴레이트, 팔리틸(메타)아크릴레이트 또는 스테아릴(메타)아크릴레이트 중에서 단독 또는 병용하여 사용하며,
상기 실란기 함유 아크릴 단량체는, 3-(메타크릴로일옥시)프로필트라이메톡시실란, 3-(메타크릴로일옥시)프로필트라이에톡시실란 또는 3-아크릴로옥시프로필트라이메톡시실란 중에서 단독 또는 병용하여 사용하는 것을 특징으로 하는, 섬유 소재 코팅용 저광택 우레탄 아크릴 하이브리드 수지 조성물.
According to claim 3,
The general acrylic monomer is used alone or in combination with methyl methacrylate, butyl acrylate, ethyl acrylate, methyl acrylate, butyl methacrylate or 2-ethylhexyl acrylate,
The acrylic monomer having a long molecular chain is used alone or in combination with lauryl (meth) acrylate, palytyl (meth) acrylate or stearyl (meth) acrylate,
The silane group-containing acrylic monomer is alone among 3-(methacryloyloxy)propyltrimethoxysilane, 3-(methacryloyloxy)propyltriethoxysilane or 3-acrylooxypropyltrimethoxysilane. Or characterized in that used in combination, low gloss urethane acrylic hybrid resin composition for coating textile materials.
상기 아크릴 단량체 혼합물은,
Tg가 0 ~ 40℃인 것을 특징으로 하는, 섬유 소재 코팅용 저광택 우레탄 아크릴 하이브리드 수지 조성물.According to claim 1,
The acrylic monomer mixture,
A low-gloss urethane-acrylic hybrid resin composition for coating textile materials, characterized in that Tg is 0 to 40 ° C.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020210143514A KR102572609B1 (en) | 2021-10-26 | 2021-10-26 | Low gloss urethane arcryl hybrid resin composition for textile coating |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020210143514A KR102572609B1 (en) | 2021-10-26 | 2021-10-26 | Low gloss urethane arcryl hybrid resin composition for textile coating |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20230059385A true KR20230059385A (en) | 2023-05-03 |
| KR102572609B1 KR102572609B1 (en) | 2023-08-31 |
Family
ID=86380689
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020210143514A KR102572609B1 (en) | 2021-10-26 | 2021-10-26 | Low gloss urethane arcryl hybrid resin composition for textile coating |
Country Status (1)
| Country | Link |
|---|---|
| KR (1) | KR102572609B1 (en) |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2012505302A (en) * | 2008-10-14 | 2012-03-01 | ビーエーエスエフ ソシエタス・ヨーロピア | Copolymer with long chain acrylate |
| KR20130124723A (en) * | 2012-05-07 | 2013-11-15 | 한진화학 주식회사 | Silylated acrylic polyurethane dispersion, preparation method of the dispersion and paint including the same |
| KR102099049B1 (en) | 2019-09-19 | 2020-04-08 | 조장호 | Method of shading coating for outdoor fabric |
| KR20200132037A (en) * | 2019-05-15 | 2020-11-25 | 한국신발피혁연구원 | Urethane acrylate hybrid coating composition for weather strips |
-
2021
- 2021-10-26 KR KR1020210143514A patent/KR102572609B1/en active IP Right Grant
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2012505302A (en) * | 2008-10-14 | 2012-03-01 | ビーエーエスエフ ソシエタス・ヨーロピア | Copolymer with long chain acrylate |
| KR20130124723A (en) * | 2012-05-07 | 2013-11-15 | 한진화학 주식회사 | Silylated acrylic polyurethane dispersion, preparation method of the dispersion and paint including the same |
| KR20200132037A (en) * | 2019-05-15 | 2020-11-25 | 한국신발피혁연구원 | Urethane acrylate hybrid coating composition for weather strips |
| KR102099049B1 (en) | 2019-09-19 | 2020-04-08 | 조장호 | Method of shading coating for outdoor fabric |
Also Published As
| Publication number | Publication date |
|---|---|
| KR102572609B1 (en) | 2023-08-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| TWI441877B (en) | Substrates and articles of manufacture coated with a waterborne 2k coating composition | |
| US5354808A (en) | Polyurethanes including pendant hindered amines and compositions incorporating same | |
| CN103087286B (en) | Waterborne polyurethane elastic dispersion and preparation method thereof | |
| JP2003041188A (en) | Nonaqueous thermosetting 2k coating agent | |
| AU2006329052A1 (en) | Curable fluorinated copolymers and coatings and processes thereof | |
| CN108546323B (en) | Cation self-extinction resin and preparation method and application thereof | |
| WO2015183654A1 (en) | Polyurethane-polyurea dispersions comprising hydrazine or hydrazide chain extenders | |
| CN103130977A (en) | Polyol polyurethane dispersions of two-component waterborne wood lacquer and preparation method thereof | |
| CN113166362B (en) | Two-component polyurethane compositions | |
| CN102898609A (en) | Waxy-luster polyurethane resin used in synthetic leather surface treatment, and preparation method thereof | |
| KR20130124723A (en) | Silylated acrylic polyurethane dispersion, preparation method of the dispersion and paint including the same | |
| US20050137322A1 (en) | Silane modified two-component polyurethane coating | |
| CN113195579A (en) | Aspartate-functional polysiloxanes, their preparation and their use | |
| US20200199084A1 (en) | Reactive ultraviolet absorber and application thereof | |
| JPWO2008108346A1 (en) | Water-based polyurethane resin composition and coating composition using the same | |
| JPH11263908A (en) | Aqueous dispersion of alkoxysilane group-containing polyurethane/urea and colloidal silica | |
| TWI400258B (en) | Polyurethane/ureas containing pendant alkoxysilane groups | |
| JP2018524418A (en) | Polyurethane coating composition | |
| KR20150011505A (en) | Water-soluble paint composition and method for producing the same | |
| KR101790375B1 (en) | Composition for coating a surface and a seat cover for automobile applied the same | |
| KR102201293B1 (en) | Urethane acrylate hybrid coating composition for weather strips | |
| CN110606932A (en) | Photo-curing polyurethane acrylate aqueous dispersion and preparation method thereof | |
| KR102572609B1 (en) | Low gloss urethane arcryl hybrid resin composition for textile coating | |
| CN112341593B (en) | Water-based surface layer polyurethane resin for automobile leather and preparation method thereof | |
| KR101044115B1 (en) | Method for preparing water dispersion polyurethane resin composition for coating of automotive plastic interior materials, and paint composition prepared using the same |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| E902 | Notification of reason for refusal | ||
| AMND | Amendment | ||
| E601 | Decision to refuse application | ||
| AMND | Amendment | ||
| X701 | Decision to grant (after re-examination) |