WO1997019993A9 - Emulsions acryliques pour encres d'impression - Google Patents
Emulsions acryliques pour encres d'impressionInfo
- Publication number
- WO1997019993A9 WO1997019993A9 PCT/US1996/018284 US9618284W WO9719993A9 WO 1997019993 A9 WO1997019993 A9 WO 1997019993A9 US 9618284 W US9618284 W US 9618284W WO 9719993 A9 WO9719993 A9 WO 9719993A9
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- composition
- isocyanate
- group
- monomer
- alkyl
- Prior art date
Links
- 238000007639 printing Methods 0.000 title claims abstract description 27
- 239000000839 emulsion Substances 0.000 title claims abstract description 25
- 239000000976 ink Substances 0.000 title abstract description 44
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 title description 15
- 239000000203 mixture Substances 0.000 claims abstract description 68
- -1 alkyl methacrylates Chemical class 0.000 claims abstract description 53
- 229920000642 polymer Polymers 0.000 claims abstract description 44
- 239000000178 monomer Substances 0.000 claims abstract description 37
- 125000004432 carbon atoms Chemical group C* 0.000 claims abstract description 32
- 239000003086 colorant Substances 0.000 claims abstract description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
- 239000001257 hydrogen Substances 0.000 claims abstract description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 9
- 125000005250 alkyl acrylate group Chemical group 0.000 claims abstract description 8
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 8
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims abstract description 8
- 239000011230 binding agent Substances 0.000 claims abstract description 6
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims abstract description 6
- 125000005156 substituted alkylene group Chemical group 0.000 claims abstract description 6
- 239000004908 Emulsion polymer Substances 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 239000000758 substrate Substances 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 12
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 8
- 238000000576 coating method Methods 0.000 claims description 7
- 150000002734 metacrylic acid derivatives Chemical class 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 6
- RRAMGCGOFNQTLD-UHFFFAOYSA-N Hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 5
- 239000011248 coating agent Substances 0.000 claims description 5
- KQDLHHSRJYVHAG-UHFFFAOYSA-N [N-]=C=O.[N-]=C=O.C1CCCCC1CC1CCCCC1 Chemical compound [N-]=C=O.[N-]=C=O.C1CCCCC1CC1CCCCC1 KQDLHHSRJYVHAG-UHFFFAOYSA-N 0.000 claims description 4
- CKDVMDCWMBSMIB-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 CKDVMDCWMBSMIB-UHFFFAOYSA-N 0.000 claims description 4
- GHHBMLHLWFGKHZ-UHFFFAOYSA-N [N-]=C=O.[N-]=C=O.CC1=CC(=O)CC(C)(C)C1 Chemical compound [N-]=C=O.[N-]=C=O.CC1=CC(=O)CC(C)(C)C1 GHHBMLHLWFGKHZ-UHFFFAOYSA-N 0.000 claims description 4
- FZDRZJKVIDHUAE-UHFFFAOYSA-N [N-]=C=O.[N-]=C=O.CC1=CC=CC=C1 Chemical compound [N-]=C=O.[N-]=C=O.CC1=CC=CC=C1 FZDRZJKVIDHUAE-UHFFFAOYSA-N 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 4
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 4
- 150000001298 alcohols Chemical class 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 239000011521 glass Substances 0.000 claims description 3
- 229920001519 homopolymer Polymers 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 claims 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N 2-methyl-2-propenoic acid methyl ester Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N [N-]=C=O Chemical compound [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 abstract description 11
- 150000002513 isocyanates Chemical class 0.000 abstract description 4
- 229920001730 Moisture cure polyurethane Polymers 0.000 abstract description 2
- 150000002483 hydrogen compounds Chemical class 0.000 abstract description 2
- 238000006243 chemical reaction Methods 0.000 description 27
- 239000002253 acid Substances 0.000 description 19
- 239000006185 dispersion Substances 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 239000003054 catalyst Substances 0.000 description 14
- 238000000034 method Methods 0.000 description 13
- 238000006116 polymerization reaction Methods 0.000 description 13
- PPBRXRYQALVLMV-UHFFFAOYSA-N styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 13
- 150000002148 esters Chemical class 0.000 description 12
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 12
- 238000007720 emulsion polymerization reaction Methods 0.000 description 11
- 229920000728 polyester Polymers 0.000 description 10
- 150000002596 lactones Chemical class 0.000 description 9
- 150000007942 carboxylates Chemical class 0.000 description 8
- 239000010408 film Substances 0.000 description 8
- 239000000049 pigment Substances 0.000 description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N oxane Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
- 239000003981 vehicle Substances 0.000 description 6
- 229920000126 Latex Polymers 0.000 description 5
- 238000007792 addition Methods 0.000 description 5
- 239000003995 emulsifying agent Substances 0.000 description 5
- 239000004816 latex Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000004408 titanium dioxide Substances 0.000 description 5
- VZCYOOQTPOCHFL-OWOJBTEDSA-N (E)-but-2-enedioate;hydron Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- JZHGRUMIRATHIU-UHFFFAOYSA-N 1-ethenyl-3-methylbenzene Chemical compound CC1=CC=CC(C=C)=C1 JZHGRUMIRATHIU-UHFFFAOYSA-N 0.000 description 4
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 1-ethenyl-4-methylbenzene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 4
- WOBHKFSMXKNTIM-UHFFFAOYSA-N 2-hydroxyethyl 2-methylacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 4
- 239000004952 Polyamide Substances 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N benzohydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N fumaric acid Chemical compound OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- 230000002401 inhibitory effect Effects 0.000 description 4
- 229920002647 polyamide Polymers 0.000 description 4
- 239000011528 polyamide (building material) Substances 0.000 description 4
- 229920002959 polymer blend Polymers 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- VHSHLMUCYSAUQU-UHFFFAOYSA-N 2-hydroxypropyl methacrylate Chemical compound CC(O)COC(=O)C(C)=C VHSHLMUCYSAUQU-UHFFFAOYSA-N 0.000 description 3
- ROOXNKNUYICQNP-UHFFFAOYSA-N Ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 3
- 239000004698 Polyethylene (PE) Substances 0.000 description 3
- 229920001228 Polyisocyanate Polymers 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 3
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 3
- 125000000129 anionic group Chemical group 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- JOYRKODLDBILNP-UHFFFAOYSA-N ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 3
- 238000009459 flexible packaging Methods 0.000 description 3
- 239000011888 foil Substances 0.000 description 3
- 238000007646 gravure printing Methods 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-M methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 125000006353 oxyethylene group Chemical group 0.000 description 3
- 229920000058 polyacrylate Polymers 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 239000005056 polyisocyanate Substances 0.000 description 3
- 229920001155 polypropylene Polymers 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 241000894007 species Species 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 239000002966 varnish Substances 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- XYLMUPLGERFSHI-UHFFFAOYSA-N α-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 3
- 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 2
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-Benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- AAVXAQDZDGZZAO-UHFFFAOYSA-N 1-chloro-2-prop-1-en-2-ylbenzene Chemical compound CC(=C)C1=CC=CC=C1Cl AAVXAQDZDGZZAO-UHFFFAOYSA-N 0.000 description 2
- KTZVZZJJVJQZHV-UHFFFAOYSA-N 1-chloro-4-ethenylbenzene Chemical compound ClC1=CC=C(C=C)C=C1 KTZVZZJJVJQZHV-UHFFFAOYSA-N 0.000 description 2
- WQDGTJOEMPEHHL-UHFFFAOYSA-N 1-chloro-4-prop-1-en-2-ylbenzene Chemical compound CC(=C)C1=CC=C(Cl)C=C1 WQDGTJOEMPEHHL-UHFFFAOYSA-N 0.000 description 2
- XXTQHVKTTBLFRI-UHFFFAOYSA-N 1-methyl-3-prop-1-en-2-ylbenzene Chemical compound CC(=C)C1=CC=CC(C)=C1 XXTQHVKTTBLFRI-UHFFFAOYSA-N 0.000 description 2
- MMSLOZQEMPDGPI-UHFFFAOYSA-N 1-methyl-4-prop-1-en-2-ylbenzene Chemical compound CC(=C)C1=CC=C(C)C=C1 MMSLOZQEMPDGPI-UHFFFAOYSA-N 0.000 description 2
- ISRGONDNXBCDBM-UHFFFAOYSA-N 2-Chlorostyrene Chemical compound ClC1=CC=CC=C1C=C ISRGONDNXBCDBM-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
- GWZMWHWAWHPNHN-UHFFFAOYSA-N 2-hydroxypropyl prop-2-enoate Chemical compound CC(O)COC(=O)C=C GWZMWHWAWHPNHN-UHFFFAOYSA-N 0.000 description 2
- DXIJHCSGLOHNES-UHFFFAOYSA-N 3,3-dimethylbut-1-enylbenzene Chemical compound CC(C)(C)C=CC1=CC=CC=C1 DXIJHCSGLOHNES-UHFFFAOYSA-N 0.000 description 2
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 description 2
- CYUZOYPRAQASLN-UHFFFAOYSA-N 3-prop-2-enoyloxypropanoic acid Chemical compound OC(=O)CCOC(=O)C=C CYUZOYPRAQASLN-UHFFFAOYSA-N 0.000 description 2
- 229920000178 Acrylic resin Polymers 0.000 description 2
- 239000004925 Acrylic resin Substances 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N Adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N Carbon tetrachloride Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 229920000298 Cellophane Polymers 0.000 description 2
- 229920002301 Cellulose acetate Polymers 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N Isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- LVHBHZANLOWSRM-UHFFFAOYSA-N Itaconic acid Chemical compound OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N Lauric acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- TUNFSRHWOTWDNC-UHFFFAOYSA-N Myristic acid Chemical compound CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-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
- IPCSVZSSVZVIGE-UHFFFAOYSA-N Palmitic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N Phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 2
- 238000003853 Pinholing Methods 0.000 description 2
- XWGJFPHUCFXLBL-UHFFFAOYSA-M Rongalite Chemical compound [Na+].OCS([O-])=O XWGJFPHUCFXLBL-UHFFFAOYSA-M 0.000 description 2
- VXUYXOFXAQZZMF-UHFFFAOYSA-N Titanium isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 2
- 229920001567 Vinyl ester Polymers 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminum Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000003945 anionic surfactant Substances 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000001530 fumaric acid Substances 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 150000002431 hydrogen Chemical group 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 230000002209 hydrophobic Effects 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 238000007644 letterpress printing Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000000123 paper Substances 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- 239000002985 plastic film Substances 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 239000002685 polymerization catalyst Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tBuOOH Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-caprolactone Chemical class O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 2
- WJJZURXPOSMHKT-MNDPQUGUSA-N (1Z)-1-[(2-chloro-4-nitrophenyl)hydrazinylidene]naphthalen-2-one Chemical compound ClC1=CC([N+](=O)[O-])=CC=C1N\N=C/1C2=CC=CC=C2C=CC\1=O WJJZURXPOSMHKT-MNDPQUGUSA-N 0.000 description 1
- POTYORUTRLSAGZ-UHFFFAOYSA-N (3-chloro-2-hydroxypropyl) prop-2-enoate Chemical compound ClCC(O)COC(=O)C=C POTYORUTRLSAGZ-UHFFFAOYSA-N 0.000 description 1
- YFIMMXDLMXFWGF-UDEUAJILSA-N (4E)-4-[[2-chloro-4-[3-chloro-4-[(2E)-2-(3-methyl-5-oxo-1-phenylpyrazol-4-ylidene)hydrazinyl]phenyl]phenyl]hydrazinylidene]-5-methyl-2-phenylpyrazol-3-one Chemical compound CC1=NN(C=2C=CC=CC=2)C(=O)\C1=N\NC(C(=C1)Cl)=CC=C1C(C=C1Cl)=CC=C1N\N=C(C1=O)/C(C)=NN1C1=CC=CC=C1 YFIMMXDLMXFWGF-UDEUAJILSA-N 0.000 description 1
- 239000001124 (E)-prop-1-ene-1,2,3-tricarboxylic acid Substances 0.000 description 1
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- 125000001117 oleyl 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])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 239000011087 paperboard Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- GYHHZMUNWLCUAH-UHFFFAOYSA-N phenothiazine Chemical compound C1=CC=C2[N]C3=CC=CC=C3SC2=C1 GYHHZMUNWLCUAH-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- GLUUGHFHXGJENI-UHFFFAOYSA-N piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 1
- 150000004885 piperazines Chemical class 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920001888 polyacrylic acid Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920000867 polyelectrolyte Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000011496 polyurethane foam Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 229940043349 potassium metabisulfite Drugs 0.000 description 1
- 235000010263 potassium metabisulphite Nutrition 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000001737 promoting Effects 0.000 description 1
- ARENMZZMCSLORU-UHFFFAOYSA-N propan-2-yl naphthalene-1-sulfonate Chemical class C1=CC=C2C(S(=O)(=O)OC(C)C)=CC=CC2=C1 ARENMZZMCSLORU-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective Effects 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 235000012739 red 2G Nutrition 0.000 description 1
- 239000004180 red 2G Substances 0.000 description 1
- 238000007717 redox polymerization reaction Methods 0.000 description 1
- 238000007763 reverse roll coating Methods 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 235000010378 sodium ascorbate Nutrition 0.000 description 1
- PPASLZSBLFJQEF-RKJRWTFHSA-M sodium ascorbate Substances [Na+].OC[C@@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RKJRWTFHSA-M 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 229940001607 sodium bisulfite Drugs 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- MGIYYNDGQBDWFE-GXTSIBQPSA-M sodium;2-[(2Z)-2-(2-oxonaphthalen-1-ylidene)hydrazinyl]naphthalene-1-sulfonate Chemical compound [Na+].C1=CC2=CC=CC=C2C(S(=O)(=O)[O-])=C1N\N=C/1C2=CC=CC=C2C=CC\1=O MGIYYNDGQBDWFE-GXTSIBQPSA-M 0.000 description 1
- PWWJJDVDTKXWOF-UHFFFAOYSA-M sodium;2-[hexadecanoyl(methyl)amino]ethanesulfonate Chemical compound [Na+].CCCCCCCCCCCCCCCC(=O)N(C)CCS([O-])(=O)=O PWWJJDVDTKXWOF-UHFFFAOYSA-M 0.000 description 1
- VQOIVBPFDDLTSX-UHFFFAOYSA-M sodium;3-dodecylbenzenesulfonate Chemical class [Na+].CCCCCCCCCCCCC1=CC=CC(S([O-])(=O)=O)=C1 VQOIVBPFDDLTSX-UHFFFAOYSA-M 0.000 description 1
- OGRPJZFGZFQRHZ-UHFFFAOYSA-M sodium;4-octoxy-4-oxo-3-sulfobutanoate Chemical compound [Na+].CCCCCCCCOC(=O)C(S(O)(=O)=O)CC([O-])=O OGRPJZFGZFQRHZ-UHFFFAOYSA-M 0.000 description 1
- 239000001587 sorbitan monostearate Substances 0.000 description 1
- 235000011076 sorbitan monostearate Nutrition 0.000 description 1
- 229940035048 sorbitan monostearate Drugs 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- REYJJPSVUYRZGE-UHFFFAOYSA-N stearylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 150000004763 sulfides Chemical class 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003784 tall oil Substances 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
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- 210000001519 tissues Anatomy 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 125000005628 tolylene group Chemical class 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
- 125000006839 xylylene group Chemical group 0.000 description 1
Definitions
- the present invention relates to acrylic emulsions useful in printing inks, said acrylic emulsions being prepared by emulsion polymerization of acrylic monomers.
- Flexible packaging printing inks are typically printed by rotary letterpress printing using flexible rubber plates or by gravure printing using engraved chrome-plated cylinders on a wide variety of substrates, e.g. plastic films such as cellulose acetate, polyethylene, polyethylene terephthalate, polyesters, polystyrene, cellophane, glassine, tissue, aluminum foils, liners, bags, paper labels, box coverings, gift wrappings, etc.
- plastic films such as cellulose acetate, polyethylene, polyethylene terephthalate, polyesters, polystyrene, cellophane, glassine, tissue, aluminum foils, liners, bags, paper labels, box coverings, gift wrappings, etc.
- Flexible packaging printing inks are widely used in the graphic arts industry. They offer economy, versatility, quality and simplicity and permit a roll of material to be multi-color printed in a continuous web at speeds of over 300 meters per minute and feed it directly to converting machines for slitting, forming or laminating. However, these inks must be carefully formulated so as to avoid the problems indigenous to these types of inks, e.g.
- U.S. Patent No. 5,338,785 discloses a flexible packaging printing ink is formulated from a copolymer of polyethylene glycol methacrylate and a polyamide resin, pigment, solvent and cellulose acetate butyrate.
- the polyamide resin is prepared by condensing a dibasic acid mixture with a diamine mixture.
- the dibasic acid mixture comprises about 0.5 to 0.8 equivalents of a C20-C44 dibasic acid mixture comprised of about 60 to 100% dimers, 0 to 40% trimers and 0 to 5% monomers, and about 0.2-0.7 equivalents of at least one C6-C12 dibasic acid such as azelaic acid and adipic acid, while the diamine mixture comprises about 0.5-0.8 equivalents of piperazine or a substituted piperazine and the balance comprises at least one C2-C12 alkyl diamine such as ethylene diamine.
- U. S. Patent No. 5,075,364 discloses a blend of a water- dissipatable polyester material, an acrylic polymer and a water-dissipatable vinyl polymer. It is stated that the acrylic polymer and the vinyl polymer must be compatible with the polyester which has a particular composition. It is stated that the polymer blends are useful for preparing ink compositions having improved block resistance, water resistance, and alcohol resistance.
- U.S. Patent No. 4,921 ,899 discloses an ink composition containing a blend of a polyester, an acrylic polymer and a vinyl polymer.
- the water-based inks containing the blend of these polymers as a binder can significantly improve ink film properties such as alcohol resistance, block resistance and water resistance as compared to use of water-dispersible polyester alone.
- the polymer blends were also employed to prepare ink primers and overprint varnishes. It is stated that these polymer blends were prepared by mixing an aqueous polyester dispersion with an acrylic emulsion which contains surfactants and other additives and that the presence of surfactants in the ink formulations creates several problems related to ink stability, printing process and print quality of the ink film.
- a number of patent documents disclose surfactants which are polymerizable, degradable or otherwise reactive during or after use.
- Examples of Japanese patent documents describing reactive anionic surfactants are listed as follows: Patent Application Nos. 46-12472, 46-34894, 49-46291 , 56-29657, and Laid Open Application 51-30285, 54-14431 , and 56-127697.
- Examples of Japanese patent documents describing reactive nonionic surfactants include Laid Open Applications Nos. 50-98484 and 56-28208.
- U.S. Patent No. 4,814,515 discloses compounds prepared by the reaction of a glycidyl (meth)acrylate with a hydroxyalkylated polyalkyleneoxy fatty alcohol followed by reaction with an alkylene oxide and the use of these compounds as an emulsifier in the emulsion or dispersion polymerization of ethylenically unsaturated monomers.
- U.S. Patent No. 4,390,401 discloses the use of acrylate or methacrylate esters of polyalkylene oxide derivatives of alkyl/aryl phenols as wetting agents and adhesion promoters in ultraviolet curable coating systems.
- Emulsion Polymerization Henkel Corporation, Ambler, Pennsylvania, states that
- TREM LF-40 is a sodium alkyl allyl sulfosuccinate with a reactive group in its molecule that will copolymerize with monomers via free radical polymerization.
- This invention relates to an aqueous polymer emulsion composition
- R 1 is hydrogen or methyl
- R 2 is an alkylene group or substituted alkylene group (typically having less than six carbon atoms, more typically two or three carbon atoms)
- R 3 is an alkylene group or substituted alkylene group (typically having less than ten carbon atoms, more typically from four to six carbon atoms),
- R 4 is an aliphatic, aromatic, cycloaliphatic or heterocyclic radical (i.e. the residue of an organic isocyanate, including trimerized isocyanates, but excluding isocyanate-functional prepolymers of active hydrogen compounds) having a functionality of n, n is an integer from two to four (typically two or three), x is an integer from one to three, and y is an integer from one to five.
- the present invention also relates to printing inks comprising a colorant and a binder for said colorant comprising an aqueous emulsion polymer of this invention.
- This invention also relates to a method of coating a substrate comprising (i) contacting a surface of a substrate with a composition comprising an ink as defined above, and (ii) drying said surface to form a film of the solids of said ink in contact with said surface.
- this coating process is a printing process.
- R 1 is hydrogen
- R 2 is an ethylene group
- R 3 is a pentamethylene group
- R 4 is the residue of isophorone di-isocyanate (and n is two), tetramethylxylene di-isocyanate (and n is two), toluene di-isocyanate (and n is two), or trimerized hexamethylene di-isocyanate (and n is three)
- x is one and y is two.
- this oligomer is a polyester oligomer prepared by forming a mixture of an acrylate- or methacrylate-functional and mono-hydroxyl- functional polyester oligomer and an isocyanate. These two components of the mixture then react in the presence of a urethane catalyst. The resulting product should contain essentially no unreacted isocyanate functionality.
- the monomer having the above formula can be characterized as an oligomer which is olefinically unsaturated.
- These monomers are derived from hydroxy-functional lactone-modified acrylate or methacrylate acid esters (hereinafter "lactone-acrylate adducts") prepared by reacting an appropriate lactone with an acrylate or methacrylate acid ester which are in turn reacted with a polyisocyanate.
- Lactones employed in the preparation of the lactone-acrylate adducts typically have the formula:
- R is hydrogen or an alkyl group having from 1 to 12 carbon atoms
- z is from 4 to 7 and at least (z - 2) of the R's is hydrogen.
- Preferred lactones are the epsilon-caprolactones wherein z is 4 and at least 6 of the R's are hydrogen with the remainder, if any, being alkyl groups.
- none of the substituents contain more than 12 carbon atoms and the total number of carbon atoms in these substituents on the lactone ring does not exceed 12.
- Unsubstituted epsilon-caprolactone, i.e., where each R is hydrogen, is a derivative of 6-hydroxyhexanoic acid. Both the unsubstituted and substituted epsilon-caprolactones are available by reacting the corresponding cyclohexanone with an oxidizing agent such as peracetic acid.
- Substituted epsilon-caprolactones found to be most suitable for preparing the present lactone-acrylate adducts are the various epsilon-monoalkylcaprolactones wherein the alkyl groups contain from 1 to 12 carbon atoms, e.g., epsilon-methyl-caprolactone, epsilon-ethyl-caprolactone, epsilon-propyl-caprolactone and epsilon-dodecyl-caprolactone.
- epsilon-dialkylcaprolactones in which the two alkyl groups are substituted on the same or different carbon atoms, but not both on the omega carbon atoms.
- epsilon-trialkylcaprolactones wherein 2 or 3 carbon atoms in the lactone ring are substituted provided, though, that the omega carbon atom is not di-substituted.
- the most preferred lactone starting reactant is the epsilon-caprolactone wherein z in the lactone formula is 4 and each R is hydrogen.
- the acrylate or methacrylate acid esters utilized to prepare the lactone-acrylate adducts contain from 1 to 3 acrylyl or alpha-substituted acrylyl groups and one or two hydroxyl groups. Such esters are commercially available and/or can be readily synthesized. Commercially available esters include the hydroxyalkyi acrylates or hydroxyalkyi methacrylates wherein the alkyl group contains from 2 to 10 carbon atoms, preferably from 2 to 6 carbon atoms.
- the hydroxyalkyi acrylates and methacrylates have the following formula:
- R 1 is hydrogen or methyl
- x is an integer from 1 to 3
- R 2 is a linear or a branched alkylene group having from 2 to 10 carbon atoms, preferably from 2 to 6 carbon atoms.
- Suitable hydroxyalkyi acrylates and methacrylates include 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl methacrylate, diethylene glycol monoacrylate, diethylene glycol monomethacrylate, glycerine dimethacrylate, trimethylol propane dimethacrylate, 3-hydroxypropyl acrylate, 2-hydroxybutyl acrylate, 4-hydroxybutyl acrylate, 3-hydroxypentyl acrylate, 6-hydroxynonyl acrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl methacrylate, 3-hydroxypropyl methacrylate, 2-hydroxybutyl methacrylate, 2-hydroxypentyl methacrylate, 5-hydroxypentyl methacrylate, 7-hydroxyheptyl methacrylate and 5-hydroxydecyl methacrylate.
- Preferred lactone-acrylate adducts have the formula:
- CH 2 CR 1 -C(O)O-R 2 -(O-C(O)R 3 ) 2 -OH wherein R 1 , R 2 , and R 3 are as described above.
- the lactone-acrylate adduct is prepared by reacting the lactone with the hydroxyalkyi acrylate in the presence of less than about 200 parts per million of a catalyst.
- the catalysts which may be used include one or more organometallic compounds and other metallic compounds such as stannic chloride or ferric chloride and other Lewis or protonic acids.
- Preferred catalysts include stannous octoate, dibutyltin dilaurate, and other tin compounds; titanates such as tetraisopropyl titanate and butyl titanate; and the like.
- the reaction is carried out at a temperature of from about 100° C to about
- the reaction may be carried out at atmospheric pressure, although higher or lower pressures may be used.
- the reaction is generally carried out in the presence of oxygen to inhibit polymerization of the hydroxyalkyi acrylate.
- the reaction is generally carried out for a period of from about 2 to about 20 hours.
- the reaction is carried out in the presence of a suitable inhibitor to prevent polymerization of the hydroxyalkyi acrylate double bond.
- a suitable inhibitor include the monomethyl ether of hydroquinone, benzoquinone, phenothiazine, methyl hydroquinone, 2,5-di-t-butylquinone, hydroquinone, benzoquinone and other common free radical inhibitors known in the art.
- the level of inhibitor used is less than 1000 parts per million, preferably less than 800 parts per million, and most preferably, less than 600 parts per million.
- a molar ratio of the lactone to hydroxyl groups in the ester of from about 1 :0.1 to about 1 :5, preferably from about 1 :0.3 to about 1:3 is typically utilized.
- R 4 is thus an aliphatic, aromatic, cycloaliphatic or heterocyclic radical.
- R 4 will contain from about 6 to about 36 carbon atoms, more typically from about 7 to about 24 carbon atoms.
- R 4 will typically be a hydrocarbon group or a heterocyclic group and is typically essentially free of urethane groups.
- Suitable polyfunctional isocyanates preferably contain on average 2 to at most 4 NCO groups.
- suitable isocyanates are 1 ,5-naphthalene di- isocyanate, 4,4'-diphenyl methane di-isocyanate (MDI), hydrogenated MDI (H12MDI), xylylene di-isocyanate (XDI), tetramethyl xylylene di-isocyanate (TMXDI), 4,4'-diphenyl dimethyl methane di-isocyanate, di- and tetraalkyl diphenyl methane di-isocyanate, 4,4-dibenzyl di-isocyanate, 1 ,3-phenylene di- isocyanate, 1 ,4-phenylene di-isocyanate, the isomers of tolylene di-isocyanate (TDI), optionally in admixture, 1-methyl-2,4-di-isocyanatocyclohexane, 1
- dicyclohexyl methane di-isocyanate dicyclohexyl methane di-isocyanate
- cyclohexane- 1 ,4-di-isocyanate ethylene di-isocyanate
- phthalic acid bis-isocyanatoethyl ester polyisocyanates containing reactive halogen atoms, such as 1- chloromethylphenyl-2,4-di-isocyanate, 1-bromomethylphenyl-2,6-di-isocyanate, 3,3-bis-chloromethylether-4,4'-diphenyl di-isocyanate.
- Sulfur-containing polyisocyanates are obtained, for example, by reaction of 2 mol hexamethylene di-isocyanate with 1 mol thiodiglycol or dihydroxydihexyl sulfide.
- Other di- isocyanates are trimethyl hexamethylene di-isocyanate, 1 ,4-di-isocyanatobutane, 1 ,2-di-isocyanatododecane and dimer fatty acid di-isocyanate.
- Tri-isocyanate isocyanurates can be prepared by trimerizing di-isocyanates at elevated temperatures, e.g.
- the lactone-acrylate adduct is typically heated to a temperature of from about 40 to 100 °C and typically about 60 °C.
- a catalytic amount of a urethane catalyst e.g. dibutyl tin dilaurate, is added followed by addition of an isocyanate compound the formula: R 4 - (NCO) n in which R' is as defined and n is typically 2 to 4, at a rate which maintains the desired reaction temperature.
- the amount of the isocyanate will be essentially equal (e.g.
- the reaction is typically heated, e.g. to a temperature of about 80 °C to about 100 °C, and held for about from 2 to about
- the reaction with the isocyanate is entirely conventional being usually carried out at moderate temperature in the presence of a catalyst which promotes the urethane-forming reaction, such as dibutyl tin dilaurate. It is customary to limit the temperature, at least during the initial stages of the reaction, to about 60 °C, and this can be done by slowing the rate of addition of one ofthe components. The temperature may be raised in the later stages of the reaction to promote completion of the reaction as measured by the consumption of the isocyanate functionality.
- the order of reaction is largely immaterial, it being possible to bring in the monohydric ethylenic compound either at the beginning, during the middle of the procedure, or as the last reactant. All of these variations are known in the art.
- the amount of the oligomeric monomer will, in relation to the total monomers, typically be a minor amount, i.e. less than 50% by weight of the total monomers. Typically, the amount of the oligomeric monomer will range from about 0.1% to about 30% by weight, more typically from about 1% to about 20% by weight, and even more typically from about 5% to about 15% by weight of the total monomers.
- the aqueous polymer emulsion of this invention also contains repeating units derived from alkyl esters of acrylic acid or methacrylic acid. Such esters are described in "Acrylic and Methacrylic Ester Polymers", Encyclopedia of Polymer Science and Engineering, vol. 1, pp.
- the polymer may also have repeating units derived from other monomers including, without limitation, ethylenically unsaturated carboxylic acids and vinyl aromatic monomers. Vinyl aromatic compounds are discussed in “Styrene Polymers” Encyclopedia of Polymer Science and Engineering, vol. 16, pp. 1-21 (John Wiley & Sons, Inc., N.Y., N.Y., 1989) and examples of such acids are described in "Acrylic and Methacrylic Acid Polymers", Encyclopedia of Polvmer
- acrylates and methacrylates examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, n-amyl, isoamyl, t-amyl, n-hexyl, 2-ethylbutyl, cyclohexyl, 2-heptyl, n-octyl, 2-ethylhexyl, n-decyl, and n-undecyl.
- a potential utility of such monomers is the ability of one of ordinary skill, in possession of this disclosure, to use such monomers to optimize the softness of the polymer.
- one measure of their utility will depend upon the desired degree of softness of the polymer which, in turn, depends at least in part, on the identity and amounts of the other monomeric units.
- a measure of the softening or plasticizing effect of a monomer can be found by examining the glass transition temperature of a homopolymer of the monomer.
- a plasticizing monomer will be such that a homopolymer of the monomer will exhibit a glass transition temperature (Tg) of less than about -30°C.
- Tg glass transition temperature
- acrylates of a straight chain alkyl having from 3 to 11 carbon atoms or a branched chain alkyl having from 5 to 11 carbon atoms may generally be useful for plasticizing the polymer.
- Vinyl aromatic compounds comprise monovinyl aromatic hydrocarbons containing from 8 to 12 carbon atoms and halogenated derivatives thereof having halo-substituted aromatic moieties. Examples include styrene, alpha-methylstyrene, vinyl toluene (e.g.
- meta-methylstyrene and para-methylstyrene meta-methylstyrene
- meta-methylstyrene para- methylstyrene
- para-ethylstyrene para-n-propylstyrene
- para-isopropylstyrene para-tert-butylstyrene
- ortho-chlorostyrene para-chlorostyrene
- para-chlorostyrene alpha-methyl- meta-methylstyrene, alpha-methyl-para-methylstyrene, tert-butyl styrene, alpha- methyl-ortho-chlorostyrene, and alpha-methyl-para-chlorostyrene.
- alkyl acrylates and methacrylates described above are preferably employed without additional comonomers for preparing ink vehicles of this invention
- other monoethylenically unsaturated polymerizable monomers useful in minor proportion (e.g. less than 10% by weight of the total monomer composition) as comonomers with acrylic monomers may be useful in preparing the polymers of this invention, particularly for uses other than in ink vehicles.
- These monomers include the vinylidene halides, vinyl halides, acrylonitrile, methacrylonitrile, vinyl esters such as vinyl formate, vinyl acetate and vinyl propionate, and mixtures of ethylene and such vinyl esters, acrylic and methacrylic acid esters of alcohol ethers such as diethylene glycol monoethyl or monobutyl ether methacrylate, C1-C10alkyl esters of beta- acryloxypropionic acid and higher oligomers of acrylic acid, styrene and alkyl substituted styrenes and vinyl aromatics including alpha-methyl styrene, mixtures of ethylene and other alkylolefins such as propylene, butylene, pentene and the like, vinyl ethers such as methyl vinyl ether, ethyl vinyl ether, vinyl 2-methoxyethyl ether, vinyl 2-chloroethyl ether and the like.
- Additional monoethylenically unsaturated polymerizable comonomers that may be useful in preparing the polymer of the invention include hydroxy functional vinyl monomers such as 2-hydroxyethyl methacrylate, 2-hydroxyethyl acrylate, 3-hydroxypropyl methacrylate, butanediol acrylate,
- 3-chloro-2-hydroxypropyl acrylate, 2-hydroxypropyl acrylate, and 2-hydroxypropyl methacrylate are useful monomers.
- useful monomers include the partial esters of unsaturated aliphatic dicarboxylic acids and particularly the alkyl half esters of such acids.
- examples of such partial esters are the alkyl half esters of itaconic acid, fumaric acid and maleic acid wherein the alkyl group contains 1 to 6 carbon atoms.
- Representative members of this group of compounds include methyl acid itaconic, butyl acid itaconic, ethyl acid fumarate, butyl acid fumarate, and methyl acid maleate.
- alpha, beta-ethylenically unsaturated carboxylic acids which may also be useful as comonomers to prepare the polymer of the invention include acrylic acid, beta-acryloxypropionic acid and higher oligomers of acrylic acid and mixtures thereof, methacrylic acid, itaconic acid, aconitic acid, crotonic acid, citraconic acid, maleic acid, fumaric acid, alpha-chloroacrylic acid, cinnamic acid, mesaconic acid and mixtures thereof.
- monomers may be emulsified with an anionic, cationic or nonionic dispersing agent, using for example from about 0.05% to 10% by weight of dispersing agent on the weight of total monomers.
- an anionic, cationic or nonionic dispersing agent such as hydroxy ethyl cellulose, methyl cellulose and polyvinyl alcohol may be used as emulsion stabilizers and protective colloids, as may polyelectrolytes such as polyacrylic acid.
- Cationic dispersion agents include lauryl-pyridinium chlorides, cetyldimethyl amine acetate, and alkyldimethylbenzylammonium chlorides in which the alkyl group has from 8 to 18 carbon atoms.
- Anionic dispersing agents include, for example, the higher fatty alcohol sulfates, such as sodium lauryl sulfate, and the like; alkylaryl sulfonates such as sodium or potassium isopropylbenzene sulfonates or isopropylnaphthalene sulfonates, and the like; alkali metal higher alkyl sulfosuccinates, such as sodium octyl sulfosuccinate, sodium N-methyl-N-palmitoyltaurate, sodium oleyl isothionate, and the like; and alkali metal salts of alkylarylpolyethoxyethanol sulfates or sulfonates, such
- Suitable non-ionic dispersing agents include alkylphenoxypolyethoxyethanols having alkyl groups of from about 7 to 18 carbon atoms and from about 6 to about 60 oxyethylene units, such as heptylphenoxypolyethoxyethanols, methyloctylphenoxypolyethoxyetha ⁇ ols, and the like; polyethoxyethanol derivatives of methylene-linked alkyl phenols; sulfur-containing agents such as those made by condensing from about 6 to about 60 moles of ethylene oxide with nonyl mercaptan, dodecyl mercaptan, and the like, or with alkylthiophenols wherein the alkyl groups contain from 6 to 16 carbon atoms; ethylene oxide derivatives of long-chained carboxylic acids, such as lauric acid, myristic acid, palmitic acid, oleic acid, and the like, or mixtures of acids such as those found in tall oil containing from 6 to 60 oxethylene
- the emulsion may contain one or more suspending aids.
- Preferred compositions contain an acrylic resin having a substantial acid number as a suspending aid. Such resins become and contribute to the polymer film prepared from the emulsion, but do not have acceptable properties by themselves.
- Preferred carboxylate polymers are vinyl aromatic/acrylic copolymers (e.g. styrene/acrylic copolymers) having a substantial acid number (typically 150-250, and preferably 180-220) and a moderate molecular weight (e.g. 6,000 to 10,000).
- Vinyl aromatic compounds are discussed in "Styrene Polymers” Encyclopedia of Polymer Science and Engineering, vol. 16, pp. 1-21 (John Wiley & Sons, Inc., N.Y., N.Y., 1989), the disclosure of which is incorporated herein by reference.
- the vinyl aromatic compounds comprise monovinyl aromatic hydrocarbons containing from 8 to 12 carbon atoms and halogenated derivatives thereof having halo-substituted aromatic moieties.
- Examples include styrene, alpha-methylstyrene, vinyl toluene (e.g. a 60/40 mixture by weight of meta- methylstyrene and para-methylstyrene), meta-methylstyrene, para- methylstyrene, para-ethylstyrene, para-n-propylstyrene, para-isopropylstyrene, para-tert-butylstyrene, ortho-chlorostyrene, para-chlorostyrene, alpha-methyl- meta-methylstyrene, alpha-methyl-para-methylstyrene, tert-butyl styrene, alpha- methyl-ortho-chlorostyrene, and alpha-methyl-para-chlorostyrene.
- styrene alpha-methylstyrene
- vinyl toluene e.g. a 60
- At least a portion of the acrylic units of the polymer will bear free carboxyl or carboxylate groups (the carboxyl or carboxylate form depending upon the pH of the aqueous emulsion).
- This carboxylate functionality is solvated by the aqueous polymerization medium and, thus, contributes to the stability of the polymer suspension.
- the aqueous composition should be essentially free of species which can react with or form a complex with such carboxylate functionality. Such freedom will ensure that the carboxylate functionality remains solvated by the aqueous polymerization medium and/or that the carboxylate polymer will not engage in measurable crosslinking, either in the aqueous polymerization medium or the films prepared therewith.
- emulsion stabilizers i.e. water soluble polymers such as water-soluble polyalkylene oxides, may be useful.
- a preferred emulsion stabilizer is a polypropylene glycol having a molecular weight in the range of 1 ,000 to 1 ,500.
- a polymerization initiator of the free radical type such as ammonium or potassium persulfate
- a redox system which also includes a reducing component such as potassium metabisulfite, sodium thiosulfate or sodium formaldehyde sulfoxylate.
- the reducing component is frequently referred to as an accelerator.
- the initiator and accelerator commonly referred to as catalyst, catalyst system or redox system, may be used in proportion from about 0.01% or less to 3% each, based on the weight of monomers to be copolymerized.
- redox catalyst systems examples include t-butyl hydroperoxide/sodium formaldehyde sulfoxylate/Fe(ll), and ammonium persulfate/sodium bisulfite/sodium hydrosulfite/Fe(ll).
- the polymerization temperature may be from room temperature to 90°C, or more, and may be optimized for the catalyst system employed, as is conventional.
- Emulsion polymerization may be seeded or unseeded. Seeded polymerization is preferred and tends to yield aqueous dispersions of latex polymer having more uniform physical properties than unseeded polymerization.
- Chain transfer agents including mercaptans, polymercaptans and polyhalogen compounds are sometimes desirable in the polymerization mixture to moderate polymer molecular weight.
- chain transfer agents which may be used include long chain alkyl mercaptans such as t-dodecyl mercaptans, alcohols such as isopropanol, isobutanol, lauryl alcohol or t-octyl alcohol, carbon tetrachloride, tetrachloroethylene and trichlorobromoethane. Generally from about 0 to 3% by weight, based on the weight of the monomer mixture, may be used.
- the polymerization process may be a thermal or redox type; that is, free radicals may be generated solely by the thermal dissociation of an initiator species or a redox system may be used.
- a monomer emulsion containing all or some portion of the monomers to be polymerized may be prepared using the monomers, water and emulsifiers.
- a catalyst solution containing catalyst in water may be separately prepared.
- the monomer emulsion and catalyst solution may be co-fed into the polymerization vessel over the course of the emulsion polymerization.
- the reaction vessel itself may initially contain water.
- the reaction vessel may also additionally contain seed emulsion and further may additionally contain an initial charge of polymerization catalyst.
- the temperature of the reaction vessel during the emulsion polymerization may be controlled by cooling to remove heat generated by the polymerization reaction or by heating the reaction vessel.
- Several monomer emulsions may be simultaneously co-fed into the reaction vessel. When multiple monomer emulsions are co-fed, they may be of different monomer composition. The sequence and rates at which the diverse monomer emulsions are co-fed may be altered during the emulsion polymerization process.
- the polymerization reaction mixture may be chased (e.g. with t-butyl hydroperoxide and sodium ascorbate) to minimize the concentrations of unreacted monomer and unreacted polymerization catalyst species.
- the pH of the contents of the reaction vessel may also be altered during the course of the emulsion polymerization process. Both thermal and redox polymerization processes may be employed.
- the inks, overprints, and primers of this invention can be prepared, for example, as disclosed in U.S. Pat. No. 4,148,779, which is incorporated herein by reference in its entirety.
- the printing ink, overprint, or primer may be prepared as follows.
- the colorant is added to the binder resin or a solution or dispersion thereof and, at a properly adjusted viscosity, dispersed thereinto with ball mill, sand mill, high-shear fluid flow mill, Cowles Dissolver, Katy Mill or the like.
- the colorants also may be dispersed directly in the polymer by milling on a heated two-roll mill at about 220°F to 360°F.
- the viscosity and printing characteristics of the ink composition may be modified further by addition of water, solvents, plasticizers, sequestered wax, surfactants and the like to suit the particular printing needs.
- the ink compositions of the present invention are not limited to any type of dye, pigment, filler, or the like, all of which are hereinafter included in the term "colorant,” and can accommodate any colorant which can be dispersed, milled, mixed, blended or dissolved in any manner in either the polymer blend, water or aqueous polymer system.
- the printing processes most advantageously used with the inks or varnishes are the flexographic and/or gravure printing processes.
- this invention relates to a method of printing comprising applying a first portion of an aqueous dispersion comprised of the polymer of this invention to a first essentially impervious printing surface, said surface having recesses therein which define a resolvable image, contacting said surface with a printable substrate, and repeating said applying and said contacting with a second portion of said aqueous dispersion and a second printable surface.
- This method may be a letterpress printing method (wherein said recesses define raised portions of the surface which carry the aqueous dispersion to the substrate, e.g. flexography) or a gravure printing method (wherein said recesses carry the aqueous dispersion to the substrate).
- an aqueous dispersion comprised of the polymer of this invention is applied to a flexible plate mounted on a plate cylinder.
- the flexible plate is then contacted with a printable substrate by rotation of the plate cylinder.
- the aqueous dispersion is applied to the flexible plate with a cylindrical transfer roll which is rotated to successively take up and then apply successive portions of the aqueous dispersion.
- a printing ink comprising a polymer of this invention as a binder and a colorant distributed through the composition in an effective amount sufficient to impart a predetermined color to the resulting composition.
- another ingredient of the printing ink of this invention is the colorant.
- colorant is specifically used in this specification in that it is intended to refer to both pigments and dyes which impart a distinct color to the composition.
- the purpose of any colorant is to provide contrast between the color of the substrate and the color of ink in order to provide a visually identifiable indicia on the substrate.
- the colorant may be any of those which are typically used in flexographic inks such as monoazo yellows (e.g. Cl Pigment Yellows 3, 5, 98); diarylide yellows (e.g. Cl Pigment Yellows 12, 13, 14); Pyrazolone Orange, Permanent Red 2G, Lithol Rubine 4B, Rubine 2B, Red Lake C, Lithol Red, Permanent Red R, Phthalocyanine Green, Phthalo-cyanine Blue, Permanent Violet, titanium dioxide, carbon black, etc.
- the colorant is typically employed in amounts of about 10-45 wt. %, preferably 15-40 wt. %, based on the weight of the ink.
- Typical substrates to which the coating or printing compositions of this invention may be applied include a wide variety of flexible materials.
- typical substrates include films of polyethylene and polypropylene generally treated for adhesion promotion; also polyester such as polyethylene terephthalate, cellophane and polyamide which may or may not be coated with PVDC for improved barrier properties.
- substrates of woven and non-woven fabrics where the fibers are of cotton, polyester, polyolefin, polyamide, polyimide and the like; metallic foils such as aluminum foil; metallized films; paper and paperboard; and cellular flexible sheet material such as polyethylene foam, polyurethane foam and sponge and foam rubber.
- compositions In coating the substrates, conventional techniques known per se are employed to apply the composition to the substrate. Thus, these compositions may be applied by use of any mechanical coating process such as air knife, trailing blade, knife coater, reverse roll or gravure coating technique. Most commonly, the composition is coated on the substrate and allowed to dry.
- a polymer can be prepared as set forth below from starting materials premixed as six separate charges in the amounts set forth below.
- the oligomer monomer is a compound of the above formula wherein R 1 is methyl, R 2 is an ethylene group, R 3 is a pentamethylene group, R 4 is the residue of bis(1 ,1'-isocyanato-4,4'-cyclohexyl) methane, n is two, x is one, and y is two.
- the polymer can be prepared by the following steps. Blanket the reactor with nitrogen and add Charge 1. Heat Charge 1 in the reactor to 77°C. Pump 17.3 parts of Charge 2 from monomer tank into the reactor and add Charge 3 to the reactor and continue mixing. Meter the remaining Charge 2 from the monomer tank into the reactor over a 70 minute period at 81 °C and mix for 1.5 hour at about 80°C.
- the resulting dispersion gave a particle size ⁇ 20 micrometers on a fineness of grind gauge. Equal parts of latex and pigment dispersion were mixed and the viscosity of the sample adjusted with deionized water to 20 seconds on a #2 shell cup. The ink was applied to the corona treated side of 1 mil polypropylene film using a hand proofer and dried using forced air gun. As a second example, this procedure was repeated using Unitane R-900 titanium dioxide pigment.
Abstract
Cette invention concerne une émulsion polymère aqueuse comportant un polymère ayant des motifs répétés, dérivés d'au moins un monomère sélectionné dans le groupe constitué par des acrylates d'alkyle et des méthacrylates d'alkyle, et au moins un monomère représenté par la formule (x(CH2=CR1-C(O)O-)R2-(O-C(O)R3)y-O-C(O)-NH)n-R4 dans laquelle R1 est hydrogène ou méthyle, R2 est un groupe alkylène ou un groupe alkylène substitué (ayant généralement moins de six atomes de carbone, et plus spécifiquement deux ou trois atomes de carbone), R3 est un groupe alkylène ou un groupe alkylène substitué (ayant généralement moins de dix atomes de carbone, et plus spécifiquement de quatre à six atomes de carbone), R4 est le reste d'un isocyanate organique (y compris d'isocyanates trimérisés, mais à l'exclusion de prépolymères à fonctionnalité isocyanate de composés actifs d'hydrogène) ayant une valence fonctionnelle égale à n, n étant un entier compris entre deux et quatre (généralement deux ou trois), x est un entier compris entre un et trois, et y est un entier compris entre un et cinq. L'invention concerne également des encres d'impression contenant un colorant ainsi qu'un liant qui est destiné audit colorant et qui contient une émulsion polymère aqueuse selon l'invention.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US777995P | 1995-11-30 | 1995-11-30 | |
US60/007,779 | 1995-11-30 |
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Publication Number | Publication Date |
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WO1997019993A1 WO1997019993A1 (fr) | 1997-06-05 |
WO1997019993A9 true WO1997019993A9 (fr) | 1997-08-14 |
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PCT/US1996/018284 WO1997019993A1 (fr) | 1995-11-30 | 1996-11-25 | Emulsions acryliques pour encres d'impression |
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US7717992B2 (en) | 2004-11-03 | 2010-05-18 | Basf Corporation | Color enhancing emulsions |
CN116925596A (zh) * | 2023-07-04 | 2023-10-24 | 青岛点石文具用品有限公司 | 一种不洇纸的速干墨水及其制备方法 |
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US5342891A (en) * | 1987-06-30 | 1994-08-30 | Union Carbide Chemicals & Plastics Technology Corporation | (N-substituted carbamoyloxy) alkanoyloxyalkyl acrylate polymers and compositions made therefrom |
US4847329A (en) * | 1987-06-30 | 1989-07-11 | Union Carbide Corporation | (N-substituted carbamoyloxy)alkanoyloxyalkyl acrylate polymers and compositions made therefrom |
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