CN102333801B - 羟基官能油多元醇丙烯酸类接枝共聚物 - Google Patents
羟基官能油多元醇丙烯酸类接枝共聚物 Download PDFInfo
- Publication number
- CN102333801B CN102333801B CN201080009688.XA CN201080009688A CN102333801B CN 102333801 B CN102333801 B CN 102333801B CN 201080009688 A CN201080009688 A CN 201080009688A CN 102333801 B CN102333801 B CN 102333801B
- Authority
- CN
- China
- Prior art keywords
- hydroxyl functional
- oil polyol
- functional oil
- mixture
- coating composition
- 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.)
- Expired - Fee Related
Links
- 125000002887 hydroxy group Chemical group [H]O* 0.000 title claims abstract description 96
- 229920005862 polyol Polymers 0.000 title claims abstract description 90
- 229920000578 graft copolymer Polymers 0.000 title claims abstract description 59
- 239000003921 oil Substances 0.000 claims abstract description 118
- 235000019198 oils Nutrition 0.000 claims abstract description 118
- 239000000203 mixture Substances 0.000 claims abstract description 71
- 239000000463 material Substances 0.000 claims abstract description 50
- 239000008199 coating composition Substances 0.000 claims abstract description 45
- 239000000178 monomer Substances 0.000 claims abstract description 44
- 150000003077 polyols Chemical class 0.000 claims abstract description 40
- 235000015112 vegetable and seed oil Nutrition 0.000 claims abstract description 33
- 239000008158 vegetable oil Substances 0.000 claims abstract description 28
- 239000003999 initiator Substances 0.000 claims abstract description 24
- 239000003377 acid catalyst Substances 0.000 claims abstract description 17
- 235000013305 food Nutrition 0.000 claims abstract description 14
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 5
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 42
- 238000000034 method Methods 0.000 claims description 40
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 23
- 239000002904 solvent Substances 0.000 claims description 23
- -1 1,1,3,3-tetramethyl butyl Chemical group 0.000 claims description 22
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 21
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 claims description 16
- 229910052751 metal Inorganic materials 0.000 claims description 16
- 239000002184 metal Substances 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 13
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 12
- 229930195729 fatty acid Natural products 0.000 claims description 12
- 239000000194 fatty acid Substances 0.000 claims description 12
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims description 10
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 8
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 claims description 8
- 235000019400 benzoyl peroxide Nutrition 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 6
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 claims description 5
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims description 5
- 229920001568 phenolic resin Polymers 0.000 claims description 5
- 229920000515 polycarbonate Polymers 0.000 claims description 5
- 239000004417 polycarbonate Substances 0.000 claims description 5
- 229920000728 polyester Polymers 0.000 claims description 5
- 229920000570 polyether Polymers 0.000 claims description 5
- 229920000098 polyolefin Polymers 0.000 claims description 5
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 4
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 4
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 claims description 4
- 238000009998 heat setting Methods 0.000 claims description 4
- 230000000737 periodic effect Effects 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 3
- 229920001807 Urea-formaldehyde Polymers 0.000 claims description 2
- 239000004202 carbamide Substances 0.000 claims description 2
- 235000013877 carbamide Nutrition 0.000 claims description 2
- MSYLJRIXVZCQHW-UHFFFAOYSA-N formaldehyde;6-phenyl-1,3,5-triazine-2,4-diamine Chemical compound O=C.NC1=NC(N)=NC(C=2C=CC=CC=2)=N1 MSYLJRIXVZCQHW-UHFFFAOYSA-N 0.000 claims description 2
- 239000012948 isocyanate Substances 0.000 claims description 2
- 150000002513 isocyanates Chemical class 0.000 claims description 2
- ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 claims description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 1
- 238000003860 storage Methods 0.000 abstract description 3
- 239000000758 substrate Substances 0.000 abstract description 3
- 238000010438 heat treatment Methods 0.000 abstract 1
- 239000002585 base Substances 0.000 description 20
- 238000000576 coating method Methods 0.000 description 16
- 239000003549 soybean oil Substances 0.000 description 16
- 235000012424 soybean oil Nutrition 0.000 description 16
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 15
- 239000011248 coating agent Substances 0.000 description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 11
- 150000004665 fatty acids Chemical class 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 8
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 8
- GDXHBFHOEYVPED-UHFFFAOYSA-N 1-(2-butoxyethoxy)butane Chemical class CCCCOCCOCCCC GDXHBFHOEYVPED-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 235000011187 glycerol Nutrition 0.000 description 7
- JWWVWJOIKZNCSU-UHFFFAOYSA-N methanesulfonic acid;2,2,2-trifluoroacetic acid Chemical compound CS(O)(=O)=O.OC(=O)C(F)(F)F JWWVWJOIKZNCSU-UHFFFAOYSA-N 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 7
- 239000004593 Epoxy Substances 0.000 description 6
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 6
- 125000003700 epoxy group Chemical group 0.000 description 6
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 6
- 229960004488 linolenic acid Drugs 0.000 description 6
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 210000000582 semen Anatomy 0.000 description 6
- 230000009466 transformation Effects 0.000 description 6
- 235000013311 vegetables Nutrition 0.000 description 6
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 5
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 239000003822 epoxy resin Substances 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 235000020778 linoleic acid Nutrition 0.000 description 5
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 5
- 239000005022 packaging material Substances 0.000 description 5
- 229920000647 polyepoxide Polymers 0.000 description 5
- 229920003987 resole Polymers 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- MNAHQWDCXOHBHK-UHFFFAOYSA-N 1-phenylpropane-1,1-diol Chemical group CCC(O)(O)C1=CC=CC=C1 MNAHQWDCXOHBHK-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 235000004347 Perilla Nutrition 0.000 description 4
- 244000124853 Perilla frutescens Species 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 235000013361 beverage Nutrition 0.000 description 4
- 239000013530 defoamer Substances 0.000 description 4
- 125000005456 glyceride group Chemical group 0.000 description 4
- 125000005908 glyceryl ester group Chemical group 0.000 description 4
- 125000005395 methacrylic acid group Chemical group 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000003784 tall oil Substances 0.000 description 4
- 239000010496 thistle oil Substances 0.000 description 4
- 238000004448 titration Methods 0.000 description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 240000001090 Papaver somniferum Species 0.000 description 3
- 235000008753 Papaver somniferum Nutrition 0.000 description 3
- 235000019484 Rapeseed oil Nutrition 0.000 description 3
- 240000006365 Vitis vinifera Species 0.000 description 3
- 235000014787 Vitis vinifera Nutrition 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 239000003849 aromatic solvent Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 239000012628 flowing agent Substances 0.000 description 3
- 239000010460 hemp oil Substances 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000003973 paint Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000010499 rapseed oil Substances 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- 235000020238 sunflower seed Nutrition 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 description 2
- HNAGHMKIPMKKBB-UHFFFAOYSA-N 1-benzylpyrrolidine-3-carboxamide Chemical compound C1C(C(=O)N)CCN1CC1=CC=CC=C1 HNAGHMKIPMKKBB-UHFFFAOYSA-N 0.000 description 2
- ZMARGGQEAJXRFP-UHFFFAOYSA-N 1-hydroxypropan-2-yl 2-methylprop-2-enoate Chemical compound OCC(C)OC(=O)C(C)=C ZMARGGQEAJXRFP-UHFFFAOYSA-N 0.000 description 2
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 2
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 2
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 2
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 239000004342 Benzoyl peroxide Substances 0.000 description 2
- 240000002791 Brassica napus Species 0.000 description 2
- 235000006008 Brassica napus var napus Nutrition 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 2
- 239000005642 Oleic acid Substances 0.000 description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
- 244000021150 Orbignya martiana Species 0.000 description 2
- 235000014643 Orbignya martiana Nutrition 0.000 description 2
- 235000019483 Peanut oil Nutrition 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 229920005830 Polyurethane Foam Polymers 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 2
- 239000004411 aluminium Substances 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-M benzoate Chemical compound [O-]C(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-M 0.000 description 2
- 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 2
- OBNCKNCVKJNDBV-UHFFFAOYSA-N butanoic acid ethyl ester Natural products CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000006735 epoxidation reaction Methods 0.000 description 2
- 230000003628 erosive effect Effects 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
- 239000000944 linseed oil Substances 0.000 description 2
- 235000021388 linseed oil Nutrition 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- 238000012423 maintenance Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000000312 peanut oil Substances 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 239000011496 polyurethane foam Substances 0.000 description 2
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 238000004080 punching Methods 0.000 description 2
- 150000004671 saturated fatty acids Chemical class 0.000 description 2
- 239000008159 sesame oil Substances 0.000 description 2
- 235000011803 sesame oil Nutrition 0.000 description 2
- REZQBEBOWJAQKS-UHFFFAOYSA-N triacontan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO REZQBEBOWJAQKS-UHFFFAOYSA-N 0.000 description 2
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 2
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 2
- 229920001567 vinyl ester resin Polymers 0.000 description 2
- 239000003643 water by type Substances 0.000 description 2
- JHPBZFOKBAGZBL-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylprop-2-enoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)=C JHPBZFOKBAGZBL-UHFFFAOYSA-N 0.000 description 1
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
- OZCMOJQQLBXBKI-UHFFFAOYSA-N 1-ethenoxy-2-methylpropane Chemical compound CC(C)COC=C OZCMOJQQLBXBKI-UHFFFAOYSA-N 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 description 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 1
- SBYMUDUGTIKLCR-UHFFFAOYSA-N 2-chloroethenylbenzene Chemical compound ClC=CC1=CC=CC=C1 SBYMUDUGTIKLCR-UHFFFAOYSA-N 0.000 description 1
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 1
- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 description 1
- GWZMWHWAWHPNHN-UHFFFAOYSA-N 2-hydroxypropyl prop-2-enoate Chemical compound CC(O)COC(=O)C=C GWZMWHWAWHPNHN-UHFFFAOYSA-N 0.000 description 1
- OELQSSWXRGADDE-UHFFFAOYSA-N 2-methylprop-2-eneperoxoic acid Chemical compound CC(=C)C(=O)OO OELQSSWXRGADDE-UHFFFAOYSA-N 0.000 description 1
- CVEPFOUZABPRMK-UHFFFAOYSA-N 2-methylprop-2-enoic acid;styrene Chemical compound CC(=C)C(O)=O.C=CC1=CC=CC=C1 CVEPFOUZABPRMK-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 1
- YHQXBTXEYZIYOV-UHFFFAOYSA-N 3-methylbut-1-ene Chemical group CC(C)C=C YHQXBTXEYZIYOV-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
- DUJMVKJJUANUMQ-UHFFFAOYSA-N 4-methylpentanenitrile Chemical compound CC(C)CCC#N DUJMVKJJUANUMQ-UHFFFAOYSA-N 0.000 description 1
- GZVHEAJQGPRDLQ-UHFFFAOYSA-N 6-phenyl-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=CC=CC=2)=N1 GZVHEAJQGPRDLQ-UHFFFAOYSA-N 0.000 description 1
- COCLLEMEIJQBAG-UHFFFAOYSA-N 8-methylnonyl 2-methylprop-2-enoate Chemical compound CC(C)CCCCCCCOC(=O)C(C)=C COCLLEMEIJQBAG-UHFFFAOYSA-N 0.000 description 1
- LVGFPWDANALGOY-UHFFFAOYSA-N 8-methylnonyl prop-2-enoate Chemical compound CC(C)CCCCCCCOC(=O)C=C LVGFPWDANALGOY-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 235000019485 Safflower oil Nutrition 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical compound [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229920006243 acrylic copolymer Polymers 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- AJXBTRZGLDTSST-UHFFFAOYSA-N amino 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)ON AJXBTRZGLDTSST-UHFFFAOYSA-N 0.000 description 1
- QDHUQRBYCVAWEN-UHFFFAOYSA-N amino prop-2-enoate Chemical compound NOC(=O)C=C QDHUQRBYCVAWEN-UHFFFAOYSA-N 0.000 description 1
- 229920003180 amino resin Polymers 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 229960004217 benzyl alcohol Drugs 0.000 description 1
- GCTPMLUUWLLESL-UHFFFAOYSA-N benzyl prop-2-enoate Chemical compound C=CC(=O)OCC1=CC=CC=C1 GCTPMLUUWLLESL-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 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
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- AQZNFKKXWPOUOF-UHFFFAOYSA-N cobalt;trifluoromethanesulfonic acid Chemical compound [Co].OS(=O)(=O)C(F)(F)F AQZNFKKXWPOUOF-UHFFFAOYSA-N 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- VBWIZSYFQSOUFQ-UHFFFAOYSA-N cyclohexanecarbonitrile Chemical compound N#CC1CCCCC1 VBWIZSYFQSOUFQ-UHFFFAOYSA-N 0.000 description 1
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 1
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 1
- OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 0.000 description 1
- KBLWLMPSVYBVDK-UHFFFAOYSA-N cyclohexyl prop-2-enoate Chemical compound C=CC(=O)OC1CCCCC1 KBLWLMPSVYBVDK-UHFFFAOYSA-N 0.000 description 1
- 229960002887 deanol Drugs 0.000 description 1
- FWLDHHJLVGRRHD-UHFFFAOYSA-N decyl prop-2-enoate Chemical compound CCCCCCCCCCOC(=O)C=C FWLDHHJLVGRRHD-UHFFFAOYSA-N 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- 239000012972 dimethylethanolamine Substances 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 229920006334 epoxy coating Polymers 0.000 description 1
- MEGHWIAOTJPCHQ-UHFFFAOYSA-N ethenyl butanoate Chemical compound CCCC(=O)OC=C MEGHWIAOTJPCHQ-UHFFFAOYSA-N 0.000 description 1
- 125000005670 ethenylalkyl group Chemical group 0.000 description 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 1
- XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical compound FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- VPVSTMAPERLKKM-UHFFFAOYSA-N glycoluril Chemical compound N1C(=O)NC2NC(=O)NC21 VPVSTMAPERLKKM-UHFFFAOYSA-N 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- LRDFRRGEGBBSRN-UHFFFAOYSA-N isobutyronitrile Chemical compound CC(C)C#N LRDFRRGEGBBSRN-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- NAPHXISIYHAKAH-UHFFFAOYSA-N lanthanum;trifluoromethanesulfonic acid Chemical compound [La].OS(=O)(=O)C(F)(F)F NAPHXISIYHAKAH-UHFFFAOYSA-N 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- RXUUYDXKHLUSHV-UHFFFAOYSA-N magnesium;trifluoromethanesulfonic acid Chemical compound [Mg].OS(=O)(=O)C(F)(F)F RXUUYDXKHLUSHV-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- VLCAYQIMSMPEBW-UHFFFAOYSA-N methyl 3-hydroxy-2-methylidenebutanoate Chemical compound COC(=O)C(=C)C(C)O VLCAYQIMSMPEBW-UHFFFAOYSA-N 0.000 description 1
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
- MHNNAWXXUZQSNM-UHFFFAOYSA-N methylethylethylene Natural products CCC(C)=C MHNNAWXXUZQSNM-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- LYJZNXAVZMEXDH-UHFFFAOYSA-N octadecan-8-yl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCC(OC(=O)C(C)=C)CCCCCCC LYJZNXAVZMEXDH-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- SRSFOMHQIATOFV-UHFFFAOYSA-N octanoyl octaneperoxoate Chemical compound CCCCCCCC(=O)OOC(=O)CCCCCCC SRSFOMHQIATOFV-UHFFFAOYSA-N 0.000 description 1
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 150000002976 peresters Chemical class 0.000 description 1
- 238000005502 peroxidation Methods 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- 230000037452 priming Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 239000003813 safflower oil Substances 0.000 description 1
- 235000005713 safflower oil Nutrition 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- KUCOHFSKRZZVRO-UHFFFAOYSA-N terephthalaldehyde Chemical compound O=CC1=CC=C(C=O)C=C1 KUCOHFSKRZZVRO-UHFFFAOYSA-N 0.000 description 1
- SWAXTRYEYUTSAP-UHFFFAOYSA-N tert-butyl ethaneperoxoate Chemical compound CC(=O)OOC(C)(C)C SWAXTRYEYUTSAP-UHFFFAOYSA-N 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- NGOCMUBXJDDBLB-UHFFFAOYSA-N trifluoromethanesulfonic acid;zinc Chemical compound [Zn].OS(=O)(=O)C(F)(F)F NGOCMUBXJDDBLB-UHFFFAOYSA-N 0.000 description 1
- 239000010913 used oil Substances 0.000 description 1
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000003466 welding Methods 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 239000004711 α-olefin 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
- C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
- C08F265/04—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of esters
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D1/00—Processes for applying liquids or other fluent materials
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D3/00—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials
- B05D3/04—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by exposure to gases
- B05D3/0433—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by exposure to gases the gas being a reactive gas
- B05D3/0453—After-treatment
- B05D3/046—Curing or evaporating the solvent
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/28—Layered products comprising a layer of synthetic resin comprising synthetic resins not wholly covered by any one of the sub-groups B32B27/30 - B32B27/42
- B32B27/285—Layered products comprising a layer of synthetic resin comprising synthetic resins not wholly covered by any one of the sub-groups B32B27/30 - B32B27/42 comprising polyethers
-
- 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
- C08F289/00—Macromolecular compounds obtained by polymerising monomers on to macromolecular compounds not provided for in groups C08F251/00 - C08F287/00
-
- 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
- C08G65/06—Cyclic ethers having no atoms other than carbon and hydrogen outside the ring
- C08G65/14—Unsaturated oxiranes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
- C08L71/08—Polyethers derived from hydroxy compounds or from their metallic derivatives
-
- 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
- C09D151/00—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers
-
- 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
- C09D191/00—Coating compositions based on oils, fats or waxes; Coating compositions based on derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
- C08L61/04—Condensation polymers of aldehydes or ketones with phenols only
- C08L61/06—Condensation polymers of aldehydes or ketones with phenols only of aldehydes with phenols
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
- C08L61/20—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
- C08L61/22—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds
- C08L61/24—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds with urea or thiourea
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
- C08L61/20—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
- C08L61/26—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
- C08L61/20—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
- C08L61/26—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds
- C08L61/28—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds with melamine
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L69/00—Compositions of polycarbonates; Compositions of derivatives of polycarbonates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
- C08L71/02—Polyalkylene oxides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Materials Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Paints Or Removers (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
Abstract
公开了可用于生产涂料组合物和涂覆表面的羟基官能油多元醇丙烯酸类接枝共聚物。在某些实施方案中,所述涂料组合物用于涂覆基材如食品和饮料储存用包装材料等。羟基官能油多元醇丙烯酸类接枝共聚物可通过在酸催化剂存在下加热环氧化植物油和羟基官能材料以形成羟基官能油多元醇并使羟基官能油多元醇与烯属不饱和单体组分的混合物在引发剂存在下反应以形成羟基官能油多元醇丙烯酸类接枝共聚物而制备。涂料组合物可通过用交联剂交联所述羟基官能油多元醇丙烯酸类接枝共聚物而制备。
Description
发明背景
1.发明领域
本发明涉及羟基官能油多元醇丙烯酸类接枝共聚物,由所述羟基官能油多元醇丙烯酸类接枝共聚物形成的涂料组合物,用所述涂料组合物涂覆基材的方法以及用所述涂料组合物涂覆的基材。
2.相关技术描述
现有技术主要基于用氨基树脂和酚醛塑料固化的环氧树脂技术。由双酚A基环氧树脂形成的涂料组合物已经用于涂覆食品和饮料用包装材料和容器。然而,在一些消费者和品牌持有人中存在对用于食品和饮料用包装材料和容器中的不含或基本不含双酚A的涂料组合物的需求。
美国专利号5,728,796公开了一种使含环氧化物的化合物与含羟基的脂族化合物在磺酸催化剂存在下反应的方法。该方法用于形成高分子量的环氧树脂。
美国专利号4,012,559公开了一种可辐射固化的涂料组合物,其含有丙烯酸类共聚物、分子量不大于2,000的多官能化合物和环氧化植物油。描述了所述固化组合物可涂覆于金属上以形成预涂覆金属产品。
Guo等人,基于大豆油的硬质聚氨酯泡沫(RigidPolyurethaneFoamsBasedonSoybeanOil),JournalofAppliedPolymerScience,第77卷,467-473(2000)教导了环氧化大豆油与甲醇反应以形成环氧化大豆油多元醇,其用于制备在绝热和包装材料中使用的聚氨酯泡沫。
美国专利申请公布号2008/0302694公开了一种可辐射固化的涂料组合物,其含有由环氧化植物油和羟基官能丙烯酸酯或羟基官能甲基丙烯酸酯在磺酸催化剂存在下反应制备的环氧化植物油低聚物。该组合物可用作食品储存中包装材料用涂料。
GB2428678公开了由聚乙二醇甲基丙烯酸酯和环氧化菜籽油在酸催化剂存在下制备改性菜籽油甘油三酯,其中该改性菜籽油甘油三酯与丙烯酸和过硫酸钾溶液混合。
WO2006/096321公开了环氧化亚麻子油,其与丙烯酸混合,然后乙酰化亚麻子油与甲基丙烯酸羟基酯在过氧化苯甲酰存在下反应。
文章标题“聚氨酯用乙氧基化大豆多元醇(EthoxylatedSoybeanPolyolsforPolyurethanes)”,lonescu(J.Polym.Environ.(2007)15:237-243)公开了通过环氧化大豆油与活性氢化合物的开环反应制备大豆多元醇。
美国专利号4,212,781公开了通过与可共聚单体在引发剂存在下反应而改性环氧树脂的方法。接枝聚合物通过将加成聚合物接枝到环氧树脂的脂族主链上而由环氧树脂形成。公开了所述方法用于制备涂料组合物用聚合物共混物。
对生产不含双酚A或基本不含双酚A的包装材料用涂料存在需要。本发明羟基官能油多元醇丙烯酸类接枝共聚物可以用于制备尤其适合作为用于食品和饮料包装材料和容器的包装材料用涂料的涂料组合物。可以配制它们以提供相比于某些市售环氧涂料体系而言更高的施用固体和改进的耐腐蚀性。
发明概述
本发明技术能够提供相比于某些现有技术涂料而言更好耐腐蚀性和更高固体的涂料。更高固体在单程操作中允许更宽的涂覆范围。
本发明包括生产羟基官能油多元醇丙烯酸类接枝共聚物的方法。该类方法可以在单一反应器或多个反应器中进行。在本发明某些实施方案中,羟基官能油多元醇丙烯酸类接枝共聚物通过包括如下步骤的方法制备:使环氧化植物油与羟基官能材料在酸催化剂存在下反应以形成羟基官能油多元醇和使羟基官能油多元醇与烯属不饱和单体组分在引发剂存在下反应以形成羟基官能油多元醇丙烯酸类接枝共聚物。
本发明还公开了包含通过包括如下步骤的方法制备的羟基官能油多元醇丙烯酸类接枝共聚物的涂料组合物:使环氧化植物油与羟基官能材料在酸催化剂存在下反应以形成羟基官能油多元醇,使羟基官能油多元醇与烯属不饱和单体组分在引发剂存在下反应以形成羟基官能油多元醇丙烯酸类接枝共聚物和用交联剂交联羟基官能油多元醇丙烯酸类接枝共聚物以形成涂料组合物。
在某些实施方案中,本发明包括通过如下步骤涂覆基材的方法:混合羟基官能油多元醇丙烯酸类接枝共聚物与交联剂以形成混合物,将所述混合物施加至基材和交联所述混合物。还公开了用所述涂料组合物涂覆的基材。在某些实施方案中,所述基材为罐或包装材料。
附图描述
图1描述了实施例6评价中所用的罐底。
发明详述
如上述实施方案和该公开的其他实施方案以及本文所述权利要求书中所用,下列术语通常具有所指含义,但如果本发明权益通过推导出下列术语的更宽含义实现,则这些含义不意味着限制本发明范围。
除了操作实施例外,或除非另有说明,所有表示成分的量、反应条件及所述用于说明书和权利要求书中的那些数值应理解为在所有情况下以术语“约”修正。因此,除非有相反说明,在以下说明书和所附权利要求书中所述的数值参数为可根据通过本发明获得的所需性能改变的近似值。至少而且不打算限制等同于权利要求书范围的教条的应用,各数值参数应根据有效位数和常规四舍五入法解释。尽管阐述本发明宽范围的数值范围和参数为近似值,但是在具体实施例中阐述的数值是尽可能准确地记录的。然而,任何数值本身都含有不可避免地在其各自测量值中发现的由标准偏差导致的某些误差。除非另有说明,本文所有百分数、比率和比例以重量计,尤其是除非另有具体说明,所述组合物中各组分比例以相对于这些组分混合物总质量的百分数给出。
还是在本文中,以端点描述的数值范围包括包含在该范围内的所有数值(例如1-5包括1、1.5、2、2.75、3、3.80、4、5等)。
还是在本文中,“a”、“an”、“the”、“至少一种”和“一种或多种”可互换使用。
还是在本文中,术语“包含”及其变型在这些术语出现在说明书和权利要求书中时不具有限制含义。
在整个申请和权利要求书中公开的术语“例如”、“非限制性地”等以及示例性化合物、范围、参数等意欲以非限制性方式表示本发明实施方案。其他化合物、范围、参数等可由本领域熟练技术人员在不背离本发明精神和范围下使用。
本发明包括至少部分地用本发明涂料组合物涂覆的基材以及涂覆所述基材的方法。本文所用术语“基材”非限制性地包括罐、金属罐、包装材料、容器、贮器或其用于支撑、触碰或接触任何类型食品或饮料的任何部分。术语“基材”、“食品罐”、“食品容器”等对于非限制性实例还包括“罐底”,其可由罐底原料冲压并用于食品和饮料包装材料中。
本发明包括通过如下步骤制备羟基官能油多元醇丙烯酸类接枝共聚物的方法:使环氧化植物油与羟基官能材料在酸催化剂存在下反应以形成羟基官能油多元醇和使羟基官能油多元醇与烯属不饱和单体组分在引发剂存在下反应以形成羟基官能油多元醇丙烯酸类接枝共聚物。所述羟基官能油多元醇丙烯酸类接枝共聚物尤其可以用于制备包装材料用涂料。在本发明某些实施方案中,用交联剂交联所述羟基官能油多元醇丙烯酸类接枝共聚物以形成食品和饮料包装材料和容器用涂料组合物。
在本发明某些实施方案中,将羟基官能油多元醇丙烯酸类接枝共聚物制成溶剂和水基涂料组合物。在某些实施方案中,溶剂基涂料组合物对于非限制性实例含有烯属不饱和单体组分,其非限制性地包括非官能烯属不饱和单体如对于非限制性实例为丙烯酸丁酯、甲基丙烯酸甲酯、苯乙烯等,并任选具有较少量的官能单体如对于非限制性实例为甲基丙烯酸羟丙酯、丙烯酸羟乙酯、甲基丙烯酸缩水甘油酯、丙烯酸、甲基丙烯酸等及其混合物。在本发明某些实施方案中,羟基官能单体以约0-约30重量%烯属不饱和单体组分混合物的水平加入,并且酸官能单体以约0-约30重量%烯属不饱和单体组分混合物的水平加入。在某些实施方案中,水基涂料组合物含有如上所述非官能和羟基官能单体,其中酸官能单体水平较高以使所述组合物可水分散。在某些实施方案中,约10-约50重量%的烯属不饱和单体组分混合物为酸官能单体。在某些实施方案中,酸官能单体为甲基丙烯酸。在该情况下,在某些实施方案中,羟基官能油多元醇丙烯酸类接枝共聚物通过加入中和碱而转变到水中,该碱例如非限制性地为氨或叔胺如非限制性地为二甲基乙醇胺以及水。在某些实施方案中,最终NV(不挥发物含量,以重量计)为约15-约40重量%。
环氧化植物油可以单独或与其他环氧化植物油组合使用。环氧化植物油可以由植物油对于非限制性实例通过在植物油中加入过氧化氢和甲酸或乙酸,然后使混合物保持在升高温度下直到部分或全部碳-碳双键转化成环氧基而制备。
植物油主要含有甘油酯,其为甘油和各种不饱和程度的脂肪酸的三酯。对于非限制性实例,本发明中所用环氧化植物油可以由植物油(脂肪酸甘油三酯)制备,例如非限制性地为甘油和具有约12-约24个碳原子的烷基链的脂肪酸的酯。在不饱和甘油酯油中作为甘油三酯的脂肪酸甘油酯通常是指干性油或半干性油。干性油对于非限制性实例包括亚麻子油、紫苏子油及其组合,而半干性油非限制性地包括松浆油、大豆油、红花油及其组合。在某些实施方案中,甘油三酯油具有相同脂肪酸链或具有连接于相同甘油分子上的不同脂肪酸链。在某些实施方案中,所述油具有含非共轭双键的脂肪酸链。在某些实施方案中,单个双键或共轭双键脂肪酸链以少量使用。甘油酯中双键不饱和度可通过碘值(数)测量,碘值(数)表示脂肪酸链中双键不饱和程度。在本发明某些实施方案中所用不饱和脂肪酸甘油酯油具有大于约25或约100-约210的碘值。
本发明所用天然存在植物油对于非限制性实例可为作为甘油酯存在的脂肪酸链的混合物并且非限制性地包括甘油酯脂肪酸酯分布,其中脂肪酸分布可以是无规的,但在所给范围内可以取决于植物来源生长条件而适当改变。在某些实施方案中使用大豆油,其大致包含约11%棕榈酸、约4%硬脂酸、约25%油酸、约51%亚麻酸和约9%亚油酸脂肪酸,其中油酸、亚油酸和亚麻酸为不饱和脂肪酸。在本发明某些实施方案中所用不饱和植物油非限制性地包括甘油酯油,其含有非共轭不饱和脂肪酸甘油酯酯如非限制性地为亚油酸和亚麻酸脂肪酸。
不饱和甘油酯油非限制性地包括玉米油、棉籽油、葡萄籽油、大麻籽油、亚麻子油、芥子油(wildmustardoil)、花生油、紫苏子油、罂粟籽油、菜籽油、红花油、麻油、大豆油、向日葵子油、低芥酸菜子油、松浆油及其混合物。本发明所用脂肪酸甘油酯对于非限制性实例包括含有亚油酸和亚麻酸脂肪酸链的那些,油如非限制性地为大麻籽油、亚麻子油、紫苏子油、罂粟籽油、红花油、大豆油、向日葵子油、低芥酸菜子油、松浆油、葡萄籽油、rattonseedoil、玉米油以及含有高水平亚油酸和亚麻酸脂肪酸甘油酯的类似油。在某些实施方案中,甘油酯可以含有较少量饱和脂肪酸。对于非限制性实例,可以使用主要含有亚油酸和亚麻酸脂肪酸甘油酯的大豆油。在本发明某些实施方案中使用该类油组合。植物油可以通过已知方法完全或部分氧化,例如对于非限制性实例使用酸如非限制性地为为用于环氧化不饱和植物油的不饱和双键的过氧酸。在某些实施方案中所用不饱和甘油酯油包括甘油单酯、甘油二酯及其与甘油三酯或饱和及不饱和脂肪酸的脂肪酸酯的混合物。
在某些实施方案中,环氧化植物油包括玉米油、棉籽油、葡萄籽油、大麻籽油、亚麻子油、芥子油、花生油、紫苏子油、罂粟籽油、菜籽油、红花油、麻油、大豆油、向日葵子油、低芥酸菜子油、松浆油、脂肪酸酯、该类油的甘油单酯或甘油二酯,或其混合物。
在本发明某些实施方案中使用市售来源的环氧化植物油,例如对于非限制性实例为以来自Arkema,Inc的商标名“VIKOLOX”和“VIKOFLEX7170”、来自ChemturaCorporation的商标名“DRAPEX6.8”和来自FerroCorp的商标名“PLAS-CHECK775”出售的环氧化大豆油。本发明所用其他环氧化植物油对于非限制性实例包括以来自Arkema,Inc.的商标名“VIKOFLEX7190”和来自ChemturaCorporation的商标名“DRAPEX10.4”出售的环氧化亚麻子油,环氧化棉籽油,环氧化红花油及其混合物。在某些实施方案中使用环氧化大豆油。
在本发明某些实施方案中,羟基官能材料非限制性地包括丙二醇、乙二醇、1,3-丙二醇、新戊二醇、三羟甲基丙烷、二甘醇、聚醚二醇、聚酯、聚碳酸酯、聚烯烃、羟基官能聚烯烃及其混合物。在某些实施方案中,羟基官能材料包括醇如非限制性地为正丁醇、2-乙基己醇、苄醇等,单独或与二醇或多元醇组合。
在某些实施方案中,羟基官能材料以约1:99-约95:5或约5:95-约40:60的羟基官能材料与环氧化植物油重量比存在。在某些实施方案中,羟基官能材料的羟基官能度与环氧化植物油的环氧官能度的当量比为约0.1:1-约3:1。在某些实施方案中,羟基官能度与环氧化植物油的环氧官能度的当量比为约0.2:1-约3:1。在某些实施方案中,羟基官能度与环氧化植物油的环氧官能度的当量比为约0.2:1。
在本发明某些实施方案中,用于促进环氧化植物油与羟基官能材料反应的酸催化剂可以为强酸催化剂,例如对于非限制性实例为一种或多种磺酸或另一强酸(pKa约为3或更小的酸),三氟甲磺酸,元素周期表(根据IUPAC1970公约)的第IIA、IIB、IIIA、IIIB或VIIIA族金属的三氟甲磺酸盐,所述三氟甲磺酸盐的混合物,或其组合。在某些实施方案中,酸催化剂的量基于反应混合物总重量可以为约1-约10,000ppm或约10-约1,000ppm。对于非限制性实例,催化剂包括第IIA族金属三氟甲磺酸盐催化剂如非限制性地为三氟甲磺酸镁、第IIB族金属三氟甲磺酸盐催化剂如非限制性地为三氟甲磺酸锌和镉、第IIIA族金属三氟甲磺酸盐催化剂如非限制性地为三氟甲磺酸镧、第IIIB族金属三氟甲磺酸盐催化剂如非限制性地为三氟甲磺酸铝和第VIIIA族金属三氟甲磺酸盐催化剂如非限制性地为三氟甲磺酸钴及其组合。金属三氟甲磺酸盐催化剂的量基于反应混合物总重量对于非限制性实例可以为约10-约1,000ppm或约10-约200ppm。本发明某些实施方案使用呈在有机溶剂中溶液形式的金属三氟甲磺酸盐催化剂。溶剂的实例非限制性地包括水,醇如正丁醇、乙醇、丙醇等以及芳烃溶剂,脂环族极性溶剂如对于非限制性实例为脂环族酮(例如环己酮),极性脂族溶剂如对于非限制性实例为烷氧基链烷醇、2-甲氧基乙醇,非羟基官能溶剂,及其混合物。
在某些实施方案中,将环氧化植物油和羟基官能材料在酸催化剂存在下加热到约50-约200℃的温度。在环氧化植物油和羟基官能材料合成中可任选包括溶剂以有助于控制粘度。在某些实施方案中,溶剂对于非限制性实例包括酮如非限制性地为甲基戊基酮,芳族溶剂如非限制性地为二甲苯或Aromatic100,酯类溶剂或其他非羟基官能溶剂,及其混合物。在本发明各实施方案中使用基于反应混合物总重量为约0-约90%或约5-约30%的溶剂。在某些实施方案中,在约2-约3小时之后,消耗>90%的环氧基。选自上述那些的溶剂以及非限制性地包括羟基官能溶剂的其他溶剂可在冷却时加入。在某些实施方案中,理想的是具有约30-约80的最终NV(不挥发物含量,以重量计)。
在某些实施方案中,烯属不饱和单体组分和引发剂与羟基官能油多元醇反应以形成羟基官能油多元醇丙烯酸类接枝共聚物。烯属不饱和单体组分和引发剂可在羟基官能油多元醇冷却之后加入。在某些实施方案中,烯属不饱和单体组分和引发剂在约2小时内加入。在某些实施方案中,羟基官能油多元醇、烯属不饱和单体组分和引发剂的反应产物在保持约1小时之后冷却以形成羟基官能油多元醇丙烯酸类接枝共聚物。虽然术语“丙烯酸类”用于描述羟基官能油多元醇丙烯酸类接枝共聚物,但在最广义上词语丙烯酸类用于包括所有烯属不饱和单体组分。
烯属不饱和单体组分可由单一单体或单体混合物组成。烯属不饱和单体组分非限制性地包括乙烯基单体、丙烯酸类单体、烯丙基单体、丙烯酰胺单体、乙烯基酯(非限制性地包括乙酸乙烯酯、丙酸乙烯酯、丁酸乙烯酯、苯甲酸乙烯酯、乙酸乙烯基异丙酯和类似的乙烯基酯)、乙烯基卤(非限制性地包括氯乙烯、氟乙烯和偏二氯乙烯)、乙烯基芳烃(非限制性地包括苯乙烯、甲基苯乙烯和类似的低级烷基苯乙烯、氯苯乙烯、乙烯基甲苯、乙烯基萘)、乙烯基脂族烃单体(非限制性地包括α-烯烃如对于非限制性实例为乙烯、丙烯、异丁烯和环己烯)以及共轭二烯(例如对于非限制性实例为1,3-丁二烯、甲基-2-丁二烯、1,3-戊二烯、2,3-二甲基丁二烯、异戊二烯、环己烷、环戊二烯和二环戊二烯)的一种或多种或其混合物。乙烯基烷基醚非限制性地包括甲基乙烯基醚、异丙基乙烯基醚、正丁基乙烯基醚和异丁基乙烯基醚。丙烯酸类单体非限制性地包括单体如对于非限制性实例为其烷基酯部分含有约1-约10个碳原子的丙烯酸或甲基丙烯酸低级烷基酯以及丙烯酸和甲基丙烯酸芳族衍生物。丙烯酸类单体对于非限制性实例包括丙烯酸甲酯和甲基丙烯酸甲酯、丙烯酸乙酯和甲基丙烯酸乙酯、丙烯酸丁酯和甲基丙烯酸丁酯、丙烯酸丙酯和甲基丙烯酸丙酯、丙烯酸2-乙基己酯和甲基丙烯酸2-乙基己酯、丙烯酸环己酯和甲基丙烯酸环己酯、丙烯酸癸酯和甲基丙烯酸癸酯、丙烯酸异癸酯和甲基丙烯酸异癸酯、丙烯酸苄基酯和甲基丙烯酸苄基酯、与丙烯酸和甲基丙烯酸反应的各种缩水甘油醚,丙烯酸羟烷基酯和甲基丙烯酸羟烷基酯如非限制性地为丙烯酸羟乙酯和甲基丙烯酸羟乙酯、丙烯酸羟丙酯和甲基丙烯酸羟丙酯,丙烯酸缩水甘油酯和甲基丙烯酸缩水甘油酯以及丙烯酸氨基酯和甲基丙烯酸氨基酯。
在某些实施方案中,烯属不饱和单体组分与羟基官能油多元醇的重量比为约1:99-约99:1,或约5:95-约95:5,或约30:70-约70:30。
在本发明某些实施方案中,各引发剂单独或组合使用。在某些实施方案中使用具有高接枝效率的引发剂。引发剂非限制性地包括偶氮化合物如对于非限制性实例为2,2'-偶氮二(异丁腈)、2,2'-偶氮二(2,4-二甲基戊腈)和1-叔丁基偶氮氰基环己烷),氢过氧化物如对于非限制性实例为氢过氧化叔丁基和氢过氧化枯烯,过氧化物如对于非限制性实例为过氧化苯甲酰、过氧化辛酰、过氧化二叔丁基、3,3'-二(过氧化叔丁基)丁酸乙酯、3,3'-二(过氧化叔戊基)丁酸乙酯、己酸叔戊基过氧-2-乙基酯、1,1,3,3-四甲基丁基过氧-2-乙基己酸酯和过氧新戊酸叔丁酯,过酸酯如对于非限制性实例为过乙酸叔丁酯、过对苯二甲酸叔丁酯和过氧苯甲酸叔丁酯,以及过碳酸酯如对于非限制性实例为过二碳酸二(1-氰基-1-甲基乙基)酯,过磷酸酯,过辛酸叔丁酯等及其混合物。
在某些实施方案中,引发剂基于单体混合物重量以约0.1-约15%或约1-约5%的量存在。
在本发明某些实施方案中,接枝烯属不饱和单体组分所选温度可以随着所选引发剂半衰期而改变。对于非限制性实例,过氧苯甲酸叔丁酯在130℃下具有约30分钟的半衰期并可以用于接枝。过氧化二苯甲酰在100℃下具有30分钟的半衰期并且在本发明某些实施方案中100℃可以为用过氧化二苯甲酰接枝羟基官能油多元醇的温度。概括地,取决于所用引发剂半衰期,反应可以在约50-约200℃下进行。
在某些实施方案中,在羟基官能油多元醇丙烯酸类接枝共聚物形成之后加入存在或不存在溶剂的一种或多种引发剂混合物以降低游离单体含量。在该一种或多种混合物中引发剂和溶剂的组成可以与用于形成羟基官能油多元醇丙烯酸类接枝共聚物的这些组分的组成相同或不同。
在某些实施方案中,丙烯酸类接枝羟基官能油多元醇与交联剂混合以形成可固化涂料组合物。本发明所用交联剂的非限制性实例包括苯胍胺、苯胍胺-甲醛、甘脲、三聚氰胺-甲醛、酚类交联剂、苯酚甲醛、脲甲醛、异氰酸酯、封端异氰酸酯及其混合物。在各实施方案中,交联剂与羟基官能油多元醇丙烯酸类接枝共聚物之比为约1:99-约90:10或约5:95-约60:40。丙烯酸类接枝羟基官能油多元醇和交联剂的混合物任选可以在固化催化剂存在下存在。固化催化剂对于非限制性实例包括十二烷基苯磺酸、对甲苯磺酸、磷酸等及其混合物。在某些实施方案中,其他聚合物如非限制性地为聚醚、聚酯、聚碳酸酯、聚氨酯等及其混合物可以混入涂料组合物中。在某些实施方案中,包装材料用涂料的固化条件在约500-约600°F下为约10-约60秒或在约250-约500°F下为约1-约20分钟。
本发明羟基官能油多元醇丙烯酸类接枝共聚物和涂料组合物可以包括本领域熟练技术人员已知的常规添加剂,例如非限制性地为流动剂、表面活性剂、消泡剂、防堵孔添加剂、润滑剂、热量释放添加剂和固化催化剂。
羟基官能油多元醇丙烯酸类接枝共聚物可用交联剂交联以形成涂料组合物。在本发明某些实施方案中,将一种或多种涂料组合物施加至基材,例如对于非限制性实例为罐、金属罐、包装材料、容器、贮器、罐底或其用于支撑或触碰任何类型食品或饮料的任何部分。在某些实施方案中,施加除本发明涂料组合物外的一种或多种涂料,例如对于非限制性实例可以在基材和涂料组合物之间施加底漆。
可以本领域熟练技术人员已知的任何方式将涂料组合物施加至基材。在某些实施方案中,将涂料组合物喷涂或辊涂至基材上。
在施加时,涂料组合物对于非限制性实例相对于约70-约90%水含有约10-约30重量%的聚合物固体,需要的话包括其他挥发物如非限制性地为少量溶剂。对于某些应用,通常除了喷雾那些以外,溶剂基聚合物溶液对于非限制性实例可以含有约20-约60重量%的聚合物固体。在某些实施方案中利用有机溶剂以促进辊涂或其他施加方法并且该类溶剂可以非限制性地包括正丁醇、2-丁氧基乙醇、二甲苯和其他芳族溶剂和酯类溶剂及其混合物。在某些实施方案中,正丁醇与2-丁氧基乙醇组合使用。在某些实施方案中,本发明涂料组合物可以用已知颜料和遮光剂着色和/或遮盖。对于许多应用,对于非限制性实例包括食品应用,颜料可以为氧化锌、炭黑或二氧化钛。在某些实施方案中,所得涂料组合物通过涂料工业中已知的常规方法施加。因此,对于非限制性实例,喷涂、辊涂、浸涂和流涂施加方法可用于透明和着色膜。在某些实施方案中,在施加至基材上之后,涂料组合物在约130-约250℃或更高的温度下热固化足够长时间以进行完全固化以及使任何挥发性组分挥发。
对于意欲作为饮料容器的基材,在某些实施方案中涂料以约0.5-约15毫克聚合物涂料/平方英寸暴露基材表面的施加率施加。在某些实施方案中,可水分散的涂料以约0.1-约1密耳的厚度施加。
实施例
本发明将进一步参照以下非限制性实施例描述。
实施例1
制备羟基官能油多元醇
在氮气下搅拌11.0克丙二醇、112.0克环氧化大豆油、30.9克甲基戊基酮和0.036克NacureA-218(可由KingIndustries获得)并加热至150℃。在<155℃下控制初始放热并使混合物在150℃下保持约2小时,然后冷却。环氧乙烷滴定表明环氧基转化率>99.9%。
制备羟基官能油多元醇丙烯酸类接枝共聚物
将100克羟基官能油多元醇与80克Aromatic100和60克甲基戊基酮混合并在氮气下加热到130℃。将6.4克甲基丙烯酸羟丙酯、36.8克苯乙烯、36.8克丙烯酸丁酯和1.6克过氧苯甲酸叔丁酯在2小时内供入混合物中。使所得混合物在130℃下保持1小时并冷却。
制备羟基官能油多元醇丙烯酸类接枝共聚物涂料组合物
将15克羟基官能油多元醇丙烯酸类接枝共聚物与5.0克Cymel1123(可由CytecIndustries获得)和1.0克十二烷基苯磺酸(10%,在丁醇中)混合以形成羟基官能油多元醇丙烯酸类接枝共聚物涂料组合物。
涂料组合物性质
将羟基官能油多元醇丙烯酸类接枝共聚物涂料组合物在铝板上压延并在580°F下烘烤20秒。膜有光泽、颜色浅且硬。用20MEK擦拭2次移走膜。该膜在沸水中1分钟之后没有发白,并且向下弯曲至约2T而没有断裂或附着损失。
实施例2
制备羟基官能油多元醇
将50.9克二甘醇和150克环氧化大豆油加入1升烧瓶中。在20℃下将0.02克NacureA-218(可由KingIndustries获得)加入烧瓶中,在氮气下搅拌混合物并加热到160℃。在<165℃下控制初始放热并使混合物在160℃下保持约3小时。环氧乙烷滴定表明环氧基转化率>99.9%。在冷却下加入50.3克乙二醇二丁醚而得到80%NV。
实施例3
制备羟基官能油多元醇
将50.0克新戊二醇和150克环氧化大豆油加入1升烧瓶中。在20℃下将0.02克NacureA-218(可由KingIndustries获得)加入烧瓶中,在氮气下搅拌混合物并加热到160℃。在<165℃下控制初始放热并使混合物在160℃下保持约3小时。环氧乙烷滴定表明环氧基转化率>99.9%。在冷却下加入50.3克乙二醇二丁醚而得到80%NV。
实施例4A
制备羟基官能油多元醇
在氮气下搅拌185.500克丙二醇、812.450克环氧化大豆油和0.206克NacureA-218(可由KingIndustries获得)并加热到150℃(141克丙二醇作为未反应溶剂残留)。在<155℃下控制初始放热并使混合物在150℃下保持约2小时,然后冷却。环氧乙烷滴定表明环氧基转化率>99.9%。
实施例4B
制备羟基官能油多元醇丙烯酸类接枝共聚物
将998.156克实施例4A的羟基官能油多元醇与1000克乙二醇二丁醚混合并在氮气下加热到100℃。将100.000克甲基丙烯酸羟丙酯、450.000克甲基丙烯酸甲酯、450.000克甲基丙烯酸丁酯和20.000克过氧化二苯甲酰在2小时内供入混合物中。使所得混合物在100℃下保持1小时,加入677g甲基戊基酮并使所得混合物冷却以形成羟基官能油多元醇丙烯酸类接枝共聚物。
实施例5A
制备羟基官能油多元醇丙烯酸类接枝共聚物乳液
将62.5克实施例4A的羟基官能油多元醇、27.5克正丁醇和30克乙二醇二丁醚装入烧瓶中并加热到100℃。将40克甲基丙烯酸甲酯、40克甲基丙烯酸丁酯、20克甲基丙烯酸和3.5克过氧化二苯甲酰在2小时内供入烧瓶中,同时保持温度在100℃下。使所得混合物在100℃下再保持1小时。将16.6克二甲基乙醇胺和30克去离子水在30分钟内加入所得混合物中,同时使温度降至80℃。将331克去离子水在1小时内加入所得混合物中,同时使温度降至40℃以形成羟基官能油多元醇丙烯酸类接枝共聚物乳液。
实施例5B
制备羟基官能油多元醇丙烯酸类接枝共聚物涂料组合物
将180克羟基官能油多元醇丙烯酸类接枝共聚物乳液与20克SantolinkEP-560(可由CytecIndustries获得)和5克HRJ15766酚醛树脂(可由SIGroup获得)混合以形成羟基官能油多元醇丙烯酸类接枝共聚物涂料组合物。
实施例6
制备羟基官能油多元醇丙烯酸类接枝共聚物涂料组合物
将59.501克实施例4B的羟基官能油多元醇丙烯酸类接枝共聚物与0.329克Modaflow丙烯酸流动剂(可由CytecIndustries获得)、0.966克ContraAirPoly消泡剂(可由UlrichGmbH获得)、0.04克Byk310消泡剂(可由BYKChemie获得)、0.867克巴西棕榈蜡分散体、13.867克酚醛树脂RSO199(可由CytecIndustries获得)、8.258克酚醛树脂SantolinkEP-560(可由CytecIndustries获得)、0.383克Cymel303、1.913克Resimene745(可由INEOSMelamines获得)、1.235克Cymel27-809(可由CytecIndustries获得)、3.925克正丁醇、3.925克Aromatic100溶剂、3.925克乙二醇二丁醚和0.867克聚乙烯蜡分散体混合以形成羟基官能油多元醇丙烯酸类接枝共聚物涂料组合物。
将通过实施例6中所述方法制备的涂料组合物涂覆于金属板上并在400F下烘烤12分钟。然后冲压该板以形成罐底,经受各种溶液并评价下表中所示性能。评价中所用罐底轮廓示于图1中。标出罐底平坦部分和焊缝位置。观察到焊缝n°2为最严密焊缝。
说明:-评价肉眼进行并以1-5评分,其中1表示可接受的性能,5表示不可接受的性能
-640CRT260可由AkzoNobel获得且含有双酚A
-640CRT260具有36.5%的NV
-实施例6具有44.5%的NV
实施例7
制备羟基官能油多元醇丙烯酸类接枝共聚物
将188.223克实施例4A的羟基官能油多元醇和190.36克乙二醇二丁醚装入烧瓶中并加热到100℃。在100℃下将39.4148克甲基丙烯酸甲酯、104.168克甲基丙烯酸丁酯、45.7493克甲基丙烯酸和3.78664克过氧化二苯甲酰在2小时内供入混合物中。将所得混合物在100℃下保持30分钟,然后加入1.41999克过辛酸叔丁酯和1.41999克甲基戊基酮,然后在100℃下保持30分钟。随后将1.41999克过辛酸叔丁酯和1.41999克甲基戊基酮加入所得混合物中,然后在100℃下保持30分钟。保持之后,加入1.41999克过辛酸叔丁酯和1.41999克甲基戊基酮,然后在100℃下再保持90分钟。加入677g甲基戊基酮并冷却所得混合物以形成羟基官能油多元醇丙烯酸类接枝共聚物。
实施例8
制备羟基官能油多元醇丙烯酸类接枝共聚物涂料组合物
将145.83克实施例7的羟基官能油多元醇丙烯酸类接枝共聚物与0.65克Modaflow丙烯酸流动剂(可由CytecIndustries获得)、1.91克ContraAirPoly消泡剂(可由UlrichGmbH获得)、0.08克Byk310消泡剂(可由BYKChemie获得)、1.71克聚乙烯蜡分散体、1.71克巴西棕榈蜡分散体、31.25克酚醛树脂RSO199(可由CytecIndustries获得)、20.83克酚醛树脂SantolinkEP-560(可由CytecIndustries获得)、7.77克正丁醇、7.77克Aromatic100溶剂和7.77克乙二醇二丁醚混合以形成羟基官能油多元醇丙烯酸类接枝共聚物涂料组合物。
Claims (21)
1.一种制备可热固化的羟基官能油多元醇接枝共聚物的方法,包括在50-200℃的温度下,使环氧化植物油与羟基官能材料在强酸催化剂存在下反应以形成羟基官能油多元醇,和使所述羟基官能油多元醇与烯属不饱和单体组分在引发剂存在下反应以形成羟基官能油多元醇接枝共聚物。
2.根据权利要求1的方法,其中所述环氧化植物油衍生自不饱和脂肪酸甘油酯。
3.根据权利要求1的方法,其中所述羟基官能材料包括丙二醇、1,3-丙二醇、乙二醇、新戊二醇、三羟甲基丙烷、二甘醇、聚醚二醇、聚酯、聚碳酸酯、羟基官能聚烯烃或其混合物。
4.根据权利要求1的方法,其中所述强酸催化剂包括根据IUPAC1970公约的元素周期表的第IIA、IIB、IIIA、IIIB或VIIIA族金属的三氟甲磺酸盐,所述三氟甲磺酸盐的混合物,或其组合。
5.根据权利要求1的方法,其中所述强酸为磺酸,三氟甲磺酸或其组合。
6.根据权利要求1的的方法,其中所述烯属不饱和单体组分与所述羟基官能油多元醇的重量比为5:95-95:5。
7.根据权利要求1的方法,其中所述引发剂包括过氧苯甲酸叔丁酯、过辛酸叔丁酯、过氧化二苯甲酰、1,1,3,3-四甲基丁基过氧-2-乙基己酸酯或其混合物。
8.根据权利要求1的方法,其中所述引发剂以0.1-15重量%所述烯属不饱和单体组分的量存在。
9.根据权利要求1的方法,其中环氧化植物油与羟基官能材料的反应在溶剂存在下进行。
10.根据权利要求9的方法,其中基于反应混合物总重量包含至多90%所述溶剂。
11.根据权利要求1的方法,其中用交联剂交联所述羟基官能油多元醇接枝共聚物以形成涂料组合物。
12.一种制备可热固化的涂料组合物的方法,所述涂料组合物包含羟基官能油多元醇接枝共聚物,所述方法包括:
在50-200℃的温度下,使环氧化植物油与羟基官能材料在强酸催化剂存在下反应以形成羟基官能油多元醇,和随后使所述羟基官能油多元醇与烯属不饱和单体组分在引发剂存在下反应以形成羟基官能油多元醇接枝共聚物;
和用交联剂交联所述羟基官能油多元醇接枝共聚物以形成涂料组合物。
13.根据权利要求12的方法,其中所述交联剂为至少一种如下物质:苯酚甲醛、三聚氰胺-甲醛、脲甲醛、苯胍胺-甲醛、封端异氰酸酯或其混合物。
14.根据权利要求12的方法,其中所述羟基官能材料包括丙二醇、1,3-丙二醇、乙二醇、新戊二醇、三羟甲基丙烷、二甘醇、聚醚二醇、聚酯、聚碳酸酯、羟基官能聚烯烃或其混合物。
15.根据权利要求12的方法,其中所述酸催化剂包括根据IUPAC1970公约的元素周期表的第IIA、IIB、IIIA、IIIB或VIIIA族金属的三氟甲磺酸盐,所述三氟甲磺酸盐的混合物,或其组合。
16.根据权利要求12的方法,其中所述引发剂以0.1-15重量%所述烯属不饱和单体组分的量存在。
17.一种涂覆与食品或饮料接触的基材的方法,所述方法包括:
在50-200℃的温度下,通过使环氧化植物油与羟基官能材料在强酸催化剂存在下反应以形成羟基官能油多元醇,和随后使所述羟基官能油多元醇与烯属不饱和单体组分在引发剂存在下反应以形成羟基官能油多元醇接枝共聚物而制备可热固化的羟基官能油多元醇接枝共聚物;将所述羟基官能油多元醇接枝共聚物与交联剂混合以形成混合物;将所述混合物施加至基材;和交联所述混合物。
18.根据权利要求17的方法,其中所述羟基官能材料包括丙二醇、1,3-丙二醇、乙二醇、新戊二醇、三羟甲基丙烷、二甘醇、聚醚二醇、聚酯、聚碳酸酯、羟基官能聚烯烃或其混合物。
19.根据权利要求17的方法,其中所述酸催化剂包括根据IUPAC1970公约的元素周期表的第IIA、IIB、IIIA、IIIB或VIIIA族金属的三氟甲磺酸盐,所述三氟甲磺酸盐的混合物,或其组合。
20.根据权利要求17的方法,其中所述引发剂以0.1-15重量%所述烯属不饱和单体组分的量存在。
21.用根据权利要求12的方法获得的涂料组合物涂覆的与食品或饮料接触的基材。
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US15773209P | 2009-03-05 | 2009-03-05 | |
US61/157,732 | 2009-03-05 | ||
EP09160286 | 2009-05-14 | ||
EP09160286.2 | 2009-05-14 | ||
PCT/EP2010/052576 WO2010100121A1 (en) | 2009-03-05 | 2010-03-02 | Hydroxyl functional oil polyol acrylic graft copolymers |
Publications (2)
Publication Number | Publication Date |
---|---|
CN102333801A CN102333801A (zh) | 2012-01-25 |
CN102333801B true CN102333801B (zh) | 2015-11-25 |
Family
ID=40885936
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201080009688.XA Expired - Fee Related CN102333801B (zh) | 2009-03-05 | 2010-03-02 | 羟基官能油多元醇丙烯酸类接枝共聚物 |
CN201080009689.4A Expired - Fee Related CN102333833B (zh) | 2009-03-05 | 2010-03-02 | 羟基官能油多元醇和由羟基官能油多元醇制备的涂料组合物 |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201080009689.4A Expired - Fee Related CN102333833B (zh) | 2009-03-05 | 2010-03-02 | 羟基官能油多元醇和由羟基官能油多元醇制备的涂料组合物 |
Country Status (13)
Country | Link |
---|---|
US (2) | US20120022186A1 (zh) |
EP (2) | EP2403914A1 (zh) |
KR (2) | KR20110132336A (zh) |
CN (2) | CN102333801B (zh) |
AU (2) | AU2010220406C1 (zh) |
CA (2) | CA2753864A1 (zh) |
ES (1) | ES2693159T3 (zh) |
HK (2) | HK1162189A1 (zh) |
MX (2) | MX2011009155A (zh) |
MY (1) | MY173945A (zh) |
RU (2) | RU2543878C2 (zh) |
WO (2) | WO2010100122A1 (zh) |
ZA (2) | ZA201105581B (zh) |
Families Citing this family (32)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2401336B1 (en) | 2009-02-24 | 2017-11-01 | Akzo Nobel Coatings International B.V. | Latex emulsions and coating compositions formed from latex emulsions |
US9394456B2 (en) | 2009-02-24 | 2016-07-19 | Akzo Nobel Coatings International B.V. | Latex emulsions and coating compositions formed from latex emulsions |
WO2010100122A1 (en) * | 2009-03-05 | 2010-09-10 | Akzo Nobel Coatings International B.V. | Hydroxyl functional oil polyols and coating compositions prepared from hydroxyl functional oil polyols |
SA111330119B1 (ar) * | 2010-12-28 | 2014-09-10 | اكزو نوبل كوتينجز انترناشيونال بى فى | مستحلبات لثية عالية الحمض بحجم جسيمي كبير |
WO2012089657A2 (en) | 2010-12-29 | 2012-07-05 | Akzo Nobel Coatings International B.V. | Adhesion promoter resin compositions and coating compositions having the adhesion promoter resin compositions |
US20150010482A1 (en) * | 2011-12-21 | 2015-01-08 | Akzo Nobel Chemicals International B.V. | Functional oil polyol acrylic graft copolymers and their use in personal care applications |
BR112014014107B1 (pt) * | 2011-12-21 | 2020-12-08 | Akzo Nobel Coatings International B.V | método de preparação de uma composição de revestimento e substrato revestido |
EP2794704B1 (en) | 2011-12-21 | 2017-04-05 | Akzo Nobel Coatings International B.V. | Water-based coating compositions |
KR20140111679A (ko) | 2011-12-28 | 2014-09-19 | 아크조노벨코팅스인터내셔널비.브이. | 페놀 수지로 경화된 아세토아세테이트 관능성 라텍스 에멀젼, 및 이로부터 형성되는 코팅 조성물 |
JP2014122323A (ja) | 2012-10-31 | 2014-07-03 | Dow Global Technologies Llc | 金属包装のためのポリカーボネートコーティング |
CN104768999B (zh) | 2012-11-08 | 2018-05-25 | 巴斯夫欧洲公司 | 作为可固化环氧树脂的2-苯基-1,3-丙二醇的缩水甘油醚衍生物和其低聚物 |
US9150685B2 (en) | 2012-11-08 | 2015-10-06 | Basf Se | Diglycidyl ethers of 2-phenyl-1,3-propanediol derivatives and oligomers thereof as curable epoxy resins |
CN105008470B (zh) * | 2013-03-12 | 2017-02-15 | 阿克佐诺贝尔国际涂料股份有限公司 | 用于制备可辐射固化低聚物的协同增效催化剂组合 |
EP2970550B1 (en) * | 2013-03-15 | 2017-08-30 | Akzo Nobel Coatings International B.V. | Acrylic grafted polyether resins based on phenol stearic acid and coating compositions formed therefrom |
WO2014140233A1 (en) | 2013-03-15 | 2014-09-18 | Akzo Nobel Coatings International B.V. | Bisphenol-a free polyether resins based on phenol stearic acid and coating compositions formed therefrom |
EP2999726B1 (en) | 2013-05-21 | 2017-07-19 | Asian Paints Ltd. | Castor oil derived hydroxy functional acrylic copolymers for surface coating applications |
KR102182319B1 (ko) * | 2013-06-05 | 2020-11-25 | 삼성전자주식회사 | 전자 기기 및 전자 기기에서 배터리 정보 제공 방법 |
CN103396342A (zh) * | 2013-08-08 | 2013-11-20 | 江苏卡特新能源有限公司 | 基于环氧大豆油改性的多官能度丙烯酸酯光聚合单体制备 |
WO2015022188A1 (de) | 2013-08-14 | 2015-02-19 | Basf Se | Glycidylether von limonen-derivaten und deren oligomere als härtbare epoxidharze |
WO2016105502A1 (en) | 2014-12-24 | 2016-06-30 | Valspar Sourcing, Inc. | Styrene-free coating compositions for packaging articles such as food and beverage containers |
US11059989B2 (en) | 2017-06-30 | 2021-07-13 | Valspar Sourcing, Inc. | Crosslinked coating compositions for packaging articles such as food and beverage containers |
EP3741818B1 (en) | 2014-12-24 | 2022-08-31 | Swimc Llc | Coating compositions for packaging articles such as food and beverage containers |
US11981822B2 (en) | 2014-12-24 | 2024-05-14 | Swimc Llc | Crosslinked coating compositions for packaging articles such as food and beverage containers |
KR101631606B1 (ko) * | 2015-03-20 | 2016-06-17 | 동구산업(주) | 에폭시화된 식물성 오일로부터 바이오폴리올의 제조방법 |
WO2016193032A1 (en) | 2015-06-02 | 2016-12-08 | Basf Se | Diglycidyl ethers of tetrahydrofuran diglycol derivatives and oligomers thereof as curable epoxy resins |
CA2993870C (en) | 2015-07-31 | 2023-09-12 | The Governors Of The University Of Alberta | Synthesis of polyols suitable for castor oil replacement |
EP3475358B1 (en) | 2016-06-28 | 2022-11-09 | PTT Global Chemical Public Company Limited | Hybrid polyols based on natural oil polyols |
US10703920B2 (en) | 2016-09-28 | 2020-07-07 | Ppg Industries Ohio, Inc. | Corrosion-resistant epoxidized vegetable oil can interior coating |
EP3660067A1 (en) * | 2018-11-30 | 2020-06-03 | Henkel AG & Co. KGaA | Adhesive composition for flexible lamination |
WO2021024033A1 (en) | 2019-08-08 | 2021-02-11 | Aditya Birla Chemicals (Thailand) Ltd. (Epoxy Division) | A modified epoxy resin |
CZ2021507A3 (cs) | 2021-11-04 | 2023-05-17 | Synpo, A.S. | Epoxy resins |
CN115894774A (zh) * | 2022-12-16 | 2023-04-04 | 嘉宝莉化工集团股份有限公司 | 一种生物基羟基聚丙烯酸酯乳液及其制备方法和应用 |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101243036A (zh) * | 2005-08-02 | 2008-08-13 | 基尔大学 | 甘油酯化合物及其用途 |
Family Cites Families (121)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE581943A (zh) | 1958-08-25 | |||
US3248356A (en) | 1963-09-26 | 1966-04-26 | Dow Chemical Co | Multisperse acrylic latexes |
GB1100569A (en) | 1966-02-08 | 1968-01-24 | Dow Chemical Co | A process for preparing acrylic latexes |
US3424766A (en) * | 1966-08-03 | 1969-01-28 | Celanese Coatings Co | Epoxidized urethane oils |
US3647520A (en) | 1970-07-06 | 1972-03-07 | Continental Can Co | Electron beam cross-linking of coating compositions containing ethylene unsaturated carboxylic acid copolymers and a melamine composition |
US3699061A (en) | 1971-02-22 | 1972-10-17 | Sherwin Williams Co | Coating composition containing urethan-modified epoxidized ester and polycarboxylic acid material |
US3827993A (en) * | 1972-06-14 | 1974-08-06 | Sherwin Williams Co | Liquid polyol compositions |
US3912670A (en) | 1973-02-28 | 1975-10-14 | O Brien Corp | Radiation curable can coating composition |
US4025548A (en) | 1974-02-04 | 1977-05-24 | The O'brien Corporation | Radiation curable oligomers |
US4264483A (en) | 1974-08-23 | 1981-04-28 | Whittaker Corporation | Decorating ink |
JPS5921909B2 (ja) | 1974-10-31 | 1984-05-23 | 東レ株式会社 | 放射線硬化性塗料組成物 |
GB1546726A (en) | 1975-06-20 | 1979-05-31 | Toyo Ink Mfg Co | Coatings on interior surfaces of metallic cans and on surfaces of metallics sheet material for cans |
US4212781A (en) | 1977-04-18 | 1980-07-15 | Scm Corporation | Modified epoxy resins, processes for making and using same and substrates coated therewith |
CA1113643A (en) | 1976-12-23 | 1981-12-01 | The Dow Chemical Company | Method of water-solubilizing high performance polyether epoxide resins, the solubilized resins and thermoset, hydrophobic coatings derived therefrom |
JPS55120613A (en) | 1979-03-13 | 1980-09-17 | Hitachi Chem Co Ltd | Production of acrylic emulsion polymer |
FR2459272A1 (fr) | 1979-06-13 | 1981-01-09 | Nippon Soda Co | Composition de peinture par revetement electrolytique du type a sediment cathodique |
CA1143080A (en) | 1979-11-19 | 1983-03-15 | Bertram Zuckert | Process for producing improved aqueous emulsions of air drying and stoving alkyd resins |
US4425450A (en) * | 1980-10-23 | 1984-01-10 | Ford Motor Company | Paint composition comprising hydroxy functional film former and improved stable flow control additive |
US4377457A (en) | 1980-11-21 | 1983-03-22 | Freeman Chemical Corporation | Dual cure coating compositions |
AT369774B (de) | 1981-06-12 | 1983-01-25 | Vianova Kunstharz Ag | Verfahren zur herstellung von waessrigen alkydharzemulsionen fuer lufttrocknende lacke |
JPS5821411A (ja) | 1981-07-29 | 1983-02-08 | Hitachi Chem Co Ltd | 被覆用樹脂組成物 |
JPS58185604A (ja) | 1982-04-26 | 1983-10-29 | Tokuyama Soda Co Ltd | ポリメタクリル酸グリシジルラテツクスの製造方法 |
FI832883A (fi) | 1982-08-12 | 1984-02-13 | Scm Corp | Vattenhaltig sjaelvhaerdbar polymerblandning |
FR2536069A1 (fr) | 1982-11-17 | 1984-05-18 | Bp Chimie Sa | Procede de preparation de produits d'addition d'epoxydes et de composes hydroxyles |
DE3246612A1 (de) * | 1982-12-16 | 1984-06-20 | Henkel KGaA, 4000 Düsseldorf | Verfahren zur herstellung modifizierter triglyceride mit im mittel epoxid- und hydroxyl- sowie ethergruppen |
JPS6047074A (ja) | 1983-08-25 | 1985-03-14 | Dai Ichi Kogyo Seiyaku Co Ltd | 防食塗料組成物 |
US4707535A (en) | 1983-10-27 | 1987-11-17 | Union Carbide Corporation | Low viscosity adducts of a poly(active hydrogen) organic compound and polyepoxide |
FR2554112B1 (fr) | 1983-10-28 | 1986-05-16 | Charbonnages Ste Chimique | Procede de reticulation de polymeres d'ethylene contenant des fonctions anhydride, compositions polymeres reticulables et application de ces compositions a l'enduction de substrats |
JPS60156708A (ja) | 1984-01-26 | 1985-08-16 | Hitachi Chem Co Ltd | ビニル変性アルキド樹脂の製造法 |
JPS60156707A (ja) | 1984-01-26 | 1985-08-16 | Hitachi Chem Co Ltd | 水性樹脂の製造法 |
JPS63112670A (ja) | 1986-10-29 | 1988-05-17 | Kansai Paint Co Ltd | 水性被覆用組成物 |
US4829124A (en) | 1986-11-17 | 1989-05-09 | Armstrong World Industries, Inc. | Dynamically crosslinked thermoplastic elastomer |
CA1296821C (en) | 1986-11-17 | 1992-03-03 | Lawrence Clark | Dynamically crosslinked thermoplastic elastomer |
EP0329027A3 (en) | 1988-02-18 | 1990-10-10 | BASF Aktiengesellschaft | Epoxide crosslinkable latices |
GB8811939D0 (en) | 1988-05-20 | 1988-06-22 | Wasson E A | Coating process |
US4959271A (en) * | 1988-07-06 | 1990-09-25 | The Dow Chemical Company | Multilayer sheet |
JPH0292916A (ja) | 1988-09-30 | 1990-04-03 | Kansai Paint Co Ltd | 樹脂組成物及び缶用塗料組成物 |
JPH02232219A (ja) | 1989-03-07 | 1990-09-14 | Dainippon Ink & Chem Inc | 水性被覆用樹脂組成物 |
JP2773915B2 (ja) | 1989-09-04 | 1998-07-09 | 関西ペイント株式会社 | 缶内面用水性被覆組成物 |
DE3931623A1 (de) | 1989-09-22 | 1991-04-04 | Lechner Gmbh | Verfahren zum herstellen eines behaelters |
US5043380A (en) | 1990-10-29 | 1991-08-27 | The Dexter Corporation | Metal container coating compositions comprising an acrylic polymer latex, melamine formaldehyde resin and an phenol formaldehyde resin |
GB9027406D0 (en) | 1990-12-18 | 1991-02-06 | Ciba Geigy Ag | Production of compounds |
DE4115146A1 (de) * | 1991-05-08 | 1992-11-12 | Henkel Kgaa | Verfahren zur herstellung von epoxid-ringoeffnungsprodukten mit einem definierten rest-epoxidsauerstoffgehalt |
US5318808A (en) | 1992-09-25 | 1994-06-07 | Polyset Company, Inc. | UV-curable coatings |
JPH08503517A (ja) | 1992-11-24 | 1996-04-16 | ミネソタ・マイニング・アンド・マニュファクチュアリング・カンパニー | 放射線硬化性オリゴマーおよびそれらから製造した磁気記録媒体 |
US5714539A (en) | 1993-10-04 | 1998-02-03 | Ppg Industries, Inc. | Polymeric surfactant and latex made therefrom |
CN1138338A (zh) | 1993-12-21 | 1996-12-18 | 陶氏化学公司 | 含环氧化物的化合物与脂族醇的反应方法 |
DE4446877A1 (de) | 1994-12-27 | 1996-07-04 | Henkel Kgaa | Verfahren zur Ringöffnung von Epoxiden |
DE19533168A1 (de) * | 1995-09-08 | 1997-03-13 | Henkel Kgaa | Fettchemische Polyole als Reaktivverdünner |
GB2305919B (en) | 1995-10-02 | 1999-12-08 | Kansai Paint Co Ltd | Ultraviolet-curing coating composition for cans |
JPH09183940A (ja) | 1995-12-28 | 1997-07-15 | Nippon Paint Co Ltd | 水性被覆組成物、製造方法及び被膜 |
US5733970A (en) | 1997-01-28 | 1998-03-31 | The Glidden Company | Aqueous dispersed, epoxy crosslinked maleated oil microgel polymers for protective coatings |
US5968605A (en) | 1997-02-27 | 1999-10-19 | Acushnet Company | Electron beam radiation curable inks for game balls, golf balls and the like |
US6197878B1 (en) | 1997-08-28 | 2001-03-06 | Eastman Chemical Company | Diol latex compositions and modified condensation polymers |
JP3879203B2 (ja) | 1997-11-04 | 2007-02-07 | 東洋インキ製造株式会社 | 活性エネルギー線硬化性化合物、オリゴマー、ならびに塗料組成物 |
US6225389B1 (en) | 1998-08-20 | 2001-05-01 | Henkel Corp. | Screen coating composition and method for applying same |
US6156816A (en) | 1998-08-20 | 2000-12-05 | Henkel Corporation | Screen coating composition and method for applying same |
US6686335B1 (en) * | 1998-09-22 | 2004-02-03 | Cephalon, Inc. | Hydroxamate-containing cysteine and serine protease inhibitors |
US6107433A (en) | 1998-11-06 | 2000-08-22 | Pittsburg State University | Process for the preparation of vegetable oil-based polyols and electroninsulating casting compounds created from vegetable oil-based polyols |
US6433121B1 (en) * | 1998-11-06 | 2002-08-13 | Pittsburg State University | Method of making natural oil-based polyols and polyurethanes therefrom |
PT1161477E (pt) * | 1998-12-24 | 2003-07-31 | Akzo Nobel Nv | Composicao aquosa de revestimento e um poliol para essa composicao |
US6399672B1 (en) | 1999-06-02 | 2002-06-04 | Sartomer Technologies Co., Inc. | Oil soluble metal-containing compounds, compositions and methods |
AU7620700A (en) | 1999-09-30 | 2001-04-30 | Dow Chemical Company, The | Method of packaging and cooking food in an ovenable container |
DE19960693A1 (de) | 1999-12-16 | 2001-07-19 | Dupont Performance Coatings | Verfahren zur anodischen Elektrotauchlackierung, sowie Elektrotauchlacke |
AU2001233339A1 (en) * | 2000-02-08 | 2001-08-20 | The C. P. Hall Company | Low voc, nonlinear polyester polyol resin-based compositions |
DE10048849A1 (de) | 2000-10-02 | 2002-04-18 | Basf Coatings Ag | Verfahren zur Herstellung eines thermisch und mit aktinischer Strahlung härtbaren Mehrkomponentensystems und seine Verwendung |
DE60233031D1 (de) | 2001-01-15 | 2009-09-03 | Unitika Ltd | Wässrige polyolefinharzzusammensetzung |
US20020151626A1 (en) | 2001-02-08 | 2002-10-17 | Hisashi Isaka | Curing composition |
US6844390B2 (en) | 2001-04-09 | 2005-01-18 | Eastman Chemical Company | Modified alkyd compositions comprising polyol latex compositions and processes of making them |
US6916874B2 (en) | 2001-09-06 | 2005-07-12 | Valspar Sourcing, Inc. | Coating compositions having epoxy functional stabilizer |
US6974665B2 (en) | 2001-09-06 | 2005-12-13 | University Of Nebraska | In situ screening to optimize variables in organic reactions |
CA2482470C (en) * | 2002-04-19 | 2011-06-07 | Ciba Specialty Chemicals Holding Inc. | Curing of coatings induced by plasma |
US20030225149A1 (en) | 2002-04-30 | 2003-12-04 | Blazecka Peter G. | Process for preparing highly functionalized gamma-butyrolactams and gamma-amino acids |
DE10225367C1 (de) | 2002-06-06 | 2003-09-18 | Ilf Forschungs Und Entwicklung | Härtbare Zubereitungen |
US7745508B2 (en) | 2002-08-30 | 2010-06-29 | Ppg Industries Ohio, Inc. | Compositions and methods for coating food cans |
JP2004250505A (ja) | 2003-02-18 | 2004-09-09 | Sentan Gijutsu Incubation Systems:Kk | コーティング組成物、コーティング薄膜および複合材料 |
US7122684B2 (en) | 2003-03-13 | 2006-10-17 | Roche Colorado Corporation | Process for preparing 1,2-diamino compounds |
AU2004234367B2 (en) * | 2003-04-25 | 2008-09-11 | Dow Global Technologies, Inc. | Vegetable oil based polyols and polyurethanes made therefrom |
US8357749B2 (en) | 2003-08-25 | 2013-01-22 | Dow Global Technologies Llc | Coating composition and articles made therefrom |
US8293808B2 (en) | 2003-09-30 | 2012-10-23 | Cargill, Incorporated | Flexible polyurethane foams prepared using modified vegetable oil-based polyols |
US7192992B2 (en) | 2004-02-04 | 2007-03-20 | Ecology Coating, Inc. | Environmentally friendly, 100% solids, actinic radiation curable coating compositions for coating thermally sensitive surfaces and/or rusted surfaces and methods, processes and assemblages for coating thereof |
DE102004012902A1 (de) | 2004-03-17 | 2005-10-06 | Bayer Materialscience Ag | Herstellung von neuen strahlenhärtenden Bindemitteln |
AU2005267131A1 (en) * | 2004-06-25 | 2006-02-02 | Andrew Guo | Modified vegetable oil-based polyols |
DE102004047921A1 (de) | 2004-10-01 | 2006-04-06 | Bayer Materialscience Ag | Polyisocyanate mit sterisch anspruchsvollen Phenolen blockiert |
EP3037488B1 (en) | 2004-10-20 | 2022-10-05 | Swimc Llc | Coating compositions for cans and methods of coating |
US7321010B2 (en) | 2005-03-08 | 2008-01-22 | Johns Manville | Fiberglass binder utilizing a curable acrylate and/or methacrylate |
CN1323122C (zh) | 2005-05-09 | 2007-06-27 | 汕头市长崎制漆有限公司 | 真空镀膜涂料 |
US7807230B2 (en) | 2005-06-16 | 2010-10-05 | Rensselaer Polytechnic Institute | Curcumin and curcuminoid compounds, and use thereof as photosensitizers of onium salts |
MX2008000776A (es) | 2005-07-22 | 2008-03-10 | Nova Chem Inc | Sistema, aparato y procedimiento para revestir y curar recipientes desechables. |
US8142858B2 (en) | 2005-08-11 | 2012-03-27 | Valspar Sourcing, Inc. | Bisphenol A and aromatic glycidyl ether-free coatings |
DE102005056959A1 (de) | 2005-11-29 | 2007-05-31 | W.R. Grace & Co. Conn. | Badge- und BPA-freie Dosenbeschichtung |
US8043713B2 (en) | 2005-12-15 | 2011-10-25 | Dow Global Technologies Llc | Compositions and aqueous dispersions |
TW200813159A (en) * | 2006-04-26 | 2008-03-16 | Dow Corning Korea Ltd | A liquid silicone rubber composition for forming breathable coating film on a textile and process for forming a breathable coating film on a textile |
WO2007127379A1 (en) | 2006-04-27 | 2007-11-08 | Pittsburg State University | Enhanced oligomeric polyols and polymers made therefrom |
US8471072B2 (en) * | 2006-05-09 | 2013-06-25 | The Curators Of The University Of Missouri | Soy-based polyols |
US20080207774A1 (en) | 2006-08-24 | 2008-08-28 | Venkataram Krishnan | Anionic latex as a carrier for active ingredients and methods for making and using the same |
US20080233062A1 (en) | 2006-08-24 | 2008-09-25 | Venkataram Krishnan | Cationic latex as a carrier for active ingredients and methods for making and using the same |
US7910680B2 (en) * | 2006-11-08 | 2011-03-22 | Dow Global Technologies Llc | Reactive (meth)acrylate monomer compositions and preparation and use thereof |
JP5506143B2 (ja) | 2006-11-28 | 2014-05-28 | 関西ペイント株式会社 | ライナー付着性が良好なキャップ用塗料組成物及び当該塗料組成物を塗装したキャップ |
EP2150566B1 (en) | 2007-04-27 | 2014-04-09 | Dow Global Technologies LLC | Low volatiles coatings, sealants and binders from renewable oils |
ES2551552T3 (es) * | 2007-06-05 | 2015-11-19 | Akzo Nobel Coatings International B.V. | Composición de revestimiento curable por radiación derivada de aceites vegetales epoxidados |
US7868085B2 (en) | 2007-07-05 | 2011-01-11 | Ppg Industries Ohio, Inc. | Aqueous dispersion comprising a branched triol having trimellitic anhydride and associated method |
EP2167591B1 (en) | 2007-07-12 | 2014-01-01 | Allnex Belgium, S.A. | Acrylated natural oil compositions |
CN101195577A (zh) | 2007-12-13 | 2008-06-11 | 天津工业大学 | 一种由大豆油制备多元醇的方法 |
CN101225141B (zh) * | 2007-12-28 | 2011-06-01 | 沈阳工业大学 | 以大豆油为原料制备可降解聚合物 |
WO2009094310A2 (en) * | 2008-01-24 | 2009-07-30 | Polyone Corporation | Catalysts for esterification of epoxidized soyates and methods of using same |
US20100055467A1 (en) * | 2008-09-02 | 2010-03-04 | Ppg Industries Ohio, Inc. | Coating compositions comprising the reaction product of a biomass derived polyol and a lactide |
US8921477B2 (en) | 2008-10-13 | 2014-12-30 | Eastern Michigan University | Conventional latex / nanolatex blends |
MX341307B (es) | 2008-11-26 | 2016-08-15 | Valspar Sourcing Inc | Polimero de poliester-carbamato y composiciones de recubrimiento de este polimero. |
RU2391368C1 (ru) | 2008-12-24 | 2010-06-10 | Открытое акционерное общество "Конструкторское бюро автоматических линий им. Л.Н. Кошкина" | Модифицирующая добавка для водоразбавляемого полимера полиоргансилоксана и сополимера бутадиена со стиролом |
EP2401336B1 (en) | 2009-02-24 | 2017-11-01 | Akzo Nobel Coatings International B.V. | Latex emulsions and coating compositions formed from latex emulsions |
WO2010100122A1 (en) * | 2009-03-05 | 2010-09-10 | Akzo Nobel Coatings International B.V. | Hydroxyl functional oil polyols and coating compositions prepared from hydroxyl functional oil polyols |
KR20120000571A (ko) | 2009-03-30 | 2012-01-02 | 다우 글로벌 테크놀로지스 엘엘씨 | 하이브리드 분산액 및 그의 제조 방법 |
WO2011009024A1 (en) | 2009-07-17 | 2011-01-20 | Valspar Sourcing, Inc. | Coating compositions for cans and methods of coating |
US20120118785A1 (en) | 2009-07-24 | 2012-05-17 | Dow Global Technologies Inc. | Coated container device, method of making the same |
BR112012000451B1 (pt) | 2009-07-24 | 2019-09-03 | Dow Global Technologies Llc | dispositivo recipiente revestido e método para fazer um dispositivo recipiente revestido |
EP2493955A1 (en) | 2009-10-30 | 2012-09-05 | Dow Global Technologies LLC | Alkyd dispersion, and a process for producing the same |
MX2013007459A (es) | 2010-12-28 | 2013-07-29 | Akzo Nobel Coatings Int Bv | Composiciones de recubrimiento curable por radiacion para metal. |
WO2012089657A2 (en) | 2010-12-29 | 2012-07-05 | Akzo Nobel Coatings International B.V. | Adhesion promoter resin compositions and coating compositions having the adhesion promoter resin compositions |
BR112014014107B1 (pt) | 2011-12-21 | 2020-12-08 | Akzo Nobel Coatings International B.V | método de preparação de uma composição de revestimento e substrato revestido |
EP2794704B1 (en) | 2011-12-21 | 2017-04-05 | Akzo Nobel Coatings International B.V. | Water-based coating compositions |
-
2010
- 2010-03-02 WO PCT/EP2010/052577 patent/WO2010100122A1/en active Application Filing
- 2010-03-02 RU RU2011139425/05A patent/RU2543878C2/ru not_active IP Right Cessation
- 2010-03-02 CA CA2753864A patent/CA2753864A1/en not_active Abandoned
- 2010-03-02 CA CA2753911A patent/CA2753911C/en active Active
- 2010-03-02 EP EP10705611A patent/EP2403914A1/en not_active Withdrawn
- 2010-03-02 AU AU2010220406A patent/AU2010220406C1/en not_active Ceased
- 2010-03-02 RU RU2011139424/04A patent/RU2539981C2/ru active
- 2010-03-02 MX MX2011009155A patent/MX2011009155A/es active IP Right Grant
- 2010-03-02 US US13/147,839 patent/US20120022186A1/en not_active Abandoned
- 2010-03-02 EP EP10705610.3A patent/EP2403885B1/en not_active Not-in-force
- 2010-03-02 AU AU2010220405A patent/AU2010220405C1/en not_active Ceased
- 2010-03-02 KR KR1020117019637A patent/KR20110132336A/ko not_active Application Discontinuation
- 2010-03-02 MY MYPI2011004078A patent/MY173945A/en unknown
- 2010-03-02 CN CN201080009688.XA patent/CN102333801B/zh not_active Expired - Fee Related
- 2010-03-02 ES ES10705610.3T patent/ES2693159T3/es active Active
- 2010-03-02 WO PCT/EP2010/052576 patent/WO2010100121A1/en active Application Filing
- 2010-03-02 KR KR1020117019636A patent/KR101695168B1/ko active IP Right Grant
- 2010-03-02 MX MX2011009154A patent/MX2011009154A/es not_active Application Discontinuation
- 2010-03-02 CN CN201080009689.4A patent/CN102333833B/zh not_active Expired - Fee Related
- 2010-03-02 US US13/147,828 patent/US9133292B2/en not_active Expired - Fee Related
-
2011
- 2011-07-28 ZA ZA2011/05581A patent/ZA201105581B/en unknown
- 2011-07-28 ZA ZA2011/05580A patent/ZA201105580B/en unknown
-
2012
- 2012-03-19 HK HK12102709.4A patent/HK1162189A1/zh not_active IP Right Cessation
- 2012-03-19 HK HK12102702.1A patent/HK1162547A1/zh not_active IP Right Cessation
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101243036A (zh) * | 2005-08-02 | 2008-08-13 | 基尔大学 | 甘油酯化合物及其用途 |
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN102333801B (zh) | 羟基官能油多元醇丙烯酸类接枝共聚物 | |
AU2010220406B9 (en) | Hydroxyl functional oil polyols and coating compositions prepared from hydroxyl functional oil polyols | |
CN104024293B (zh) | 水基涂料组合物 | |
CN103998480B (zh) | 溶剂基涂料组合物 | |
CN105189684A (zh) | 具有羟基苯基官能聚合物的涂料组合物 | |
KR20140111679A (ko) | 페놀 수지로 경화된 아세토아세테이트 관능성 라텍스 에멀젼, 및 이로부터 형성되는 코팅 조성물 | |
CN103282452A (zh) | 高酸大粒度胶乳乳液,高酸大粒度胶乳乳液的经改善的稳定性和由其形成的涂料组合物 | |
SA112340119B1 (ar) | تركيبات طلاء قائمة على الماء |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
REG | Reference to a national code |
Ref country code: HK Ref legal event code: DE Ref document number: 1162547 Country of ref document: HK |
|
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
REG | Reference to a national code |
Ref country code: HK Ref legal event code: GR Ref document number: 1162547 Country of ref document: HK |
|
CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20151125 |
|
CF01 | Termination of patent right due to non-payment of annual fee |