JP5299592B1 - ポリウレタンポリ尿素樹脂組成物、印刷インキ用バインダー、及び印刷インキ - Google Patents
ポリウレタンポリ尿素樹脂組成物、印刷インキ用バインダー、及び印刷インキ Download PDFInfo
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- JP5299592B1 JP5299592B1 JP2013500260A JP2013500260A JP5299592B1 JP 5299592 B1 JP5299592 B1 JP 5299592B1 JP 2013500260 A JP2013500260 A JP 2013500260A JP 2013500260 A JP2013500260 A JP 2013500260A JP 5299592 B1 JP5299592 B1 JP 5299592B1
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- acid
- polyurethane polyurea
- resin composition
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- polyurea resin
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- 229920002396 Polyurea Polymers 0.000 title claims abstract description 59
- 229920002635 polyurethane Polymers 0.000 title claims abstract description 59
- 239000004814 polyurethane Substances 0.000 title claims abstract description 59
- 239000011342 resin composition Substances 0.000 title claims abstract description 34
- 238000007639 printing Methods 0.000 title claims abstract description 29
- 239000011230 binding agent Substances 0.000 title claims description 12
- 229920005989 resin Polymers 0.000 claims abstract description 76
- 239000011347 resin Substances 0.000 claims abstract description 76
- 239000002904 solvent Substances 0.000 claims abstract description 38
- 239000002253 acid Substances 0.000 claims abstract description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 25
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 33
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 30
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 claims description 29
- JVYDLYGCSIHCMR-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)butanoic acid Chemical compound CCC(CO)(CO)C(O)=O JVYDLYGCSIHCMR-UHFFFAOYSA-N 0.000 claims description 4
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 claims description 4
- 229940090181 propyl acetate Drugs 0.000 claims description 4
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 4
- DNXHEGUUPJUMQT-CBZIJGRNSA-N Estrone Chemical compound OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 DNXHEGUUPJUMQT-CBZIJGRNSA-N 0.000 claims 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 1
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 claims 1
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims 1
- 235000019260 propionic acid Nutrition 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 14
- 238000003860 storage Methods 0.000 abstract description 14
- 238000004040 coloring Methods 0.000 abstract description 4
- 150000002148 esters Chemical class 0.000 abstract description 2
- -1 hydroxide ions Chemical class 0.000 description 73
- 239000000243 solution Substances 0.000 description 37
- 239000000976 ink Substances 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 20
- 230000008859 change Effects 0.000 description 19
- 150000001875 compounds Chemical class 0.000 description 19
- 229920005862 polyol Polymers 0.000 description 16
- 150000002009 diols Chemical class 0.000 description 15
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 14
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 239000005056 polyisocyanate Substances 0.000 description 11
- 229920001228 polyisocyanate Polymers 0.000 description 11
- 239000000203 mixture Substances 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 7
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 7
- 239000001361 adipic acid Substances 0.000 description 7
- 235000011037 adipic acid Nutrition 0.000 description 7
- 125000003277 amino group Chemical group 0.000 description 7
- 229920000728 polyester Polymers 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 6
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 6
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 5
- 239000005058 Isophorone diisocyanate Substances 0.000 description 5
- 239000004721 Polyphenylene oxide Substances 0.000 description 5
- 125000005442 diisocyanate group Chemical group 0.000 description 5
- 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 5
- 229920000570 polyether Polymers 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
- PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 description 4
- SXFJDZNJHVPHPH-UHFFFAOYSA-N 3-methylpentane-1,5-diol Chemical compound OCCC(C)CCO SXFJDZNJHVPHPH-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- 239000003759 ester based solvent Substances 0.000 description 4
- 239000012948 isocyanate Substances 0.000 description 4
- 150000002513 isocyanates Chemical class 0.000 description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
- 150000002596 lactones Chemical class 0.000 description 4
- 239000012046 mixed solvent Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- UFYGCFHQAXXBCF-UHFFFAOYSA-N 2,4-dihydroxybutanoic acid Chemical compound OCCC(O)C(O)=O UFYGCFHQAXXBCF-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000005456 alcohol based solvent Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 150000004985 diamines Chemical class 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
- 239000011976 maleic acid Substances 0.000 description 3
- 239000003973 paint Substances 0.000 description 3
- 229920005906 polyester polyol Polymers 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 3
- XVOUMQNXTGKGMA-OWOJBTEDSA-N (E)-glutaconic acid Chemical compound OC(=O)C\C=C\C(O)=O XVOUMQNXTGKGMA-OWOJBTEDSA-N 0.000 description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 2
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 2
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 2
- JCTXKRPTIMZBJT-UHFFFAOYSA-N 2,2,4-trimethylpentane-1,3-diol Chemical compound CC(C)C(O)C(C)(C)CO JCTXKRPTIMZBJT-UHFFFAOYSA-N 0.000 description 2
- PDGXJDXVGMHUIR-UHFFFAOYSA-N 2,3-Dihydroxy-3-methylpentanoate Chemical compound CCC(C)(O)C(O)C(O)=O PDGXJDXVGMHUIR-UHFFFAOYSA-N 0.000 description 2
- JTEYKUFKXGDTEU-UHFFFAOYSA-N 2,3-dihydroxy-3-methylbutanoic acid Chemical compound CC(C)(O)C(O)C(O)=O JTEYKUFKXGDTEU-UHFFFAOYSA-N 0.000 description 2
- RSKGLBJVIAQRMC-UHFFFAOYSA-N 2,4,5-trihydroxypentanoic acid Chemical compound OCC(O)CC(O)C(O)=O RSKGLBJVIAQRMC-UHFFFAOYSA-N 0.000 description 2
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 2
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 2
- YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 description 2
- CWNOEVURTVLUNV-UHFFFAOYSA-N 2-(propoxymethyl)oxirane Chemical compound CCCOCC1CO1 CWNOEVURTVLUNV-UHFFFAOYSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- KXEISHUBUXWXGY-UHFFFAOYSA-N 2-hydroxy-2-(1-hydroxyethyl)-3-methylbutanoic acid Chemical compound CC(C)C(O)(C(C)O)C(O)=O KXEISHUBUXWXGY-UHFFFAOYSA-N 0.000 description 2
- DZAIOXUZHHTJKN-UHFFFAOYSA-N 3,4-dihydroxybutyric acid Chemical compound OCC(O)CC(O)=O DZAIOXUZHHTJKN-UHFFFAOYSA-N 0.000 description 2
- KJTLQQUUPVSXIM-UHFFFAOYSA-N DL-mevalonic acid Natural products OCCC(O)(C)CC(O)=O KJTLQQUUPVSXIM-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
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- 125000001931 aliphatic group Chemical group 0.000 description 2
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 2
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 2
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- 238000009833 condensation Methods 0.000 description 2
- IFDVQVHZEKPUSC-UHFFFAOYSA-N cyclohex-3-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCC=CC1C(O)=O IFDVQVHZEKPUSC-UHFFFAOYSA-N 0.000 description 2
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
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- CHUMGDDVFASTDV-BXXZVTAOSA-N (2r,3r,4r)-2,3,4-trihydroxypentanoic acid Chemical compound C[C@@H](O)[C@@H](O)[C@@H](O)C(O)=O CHUMGDDVFASTDV-BXXZVTAOSA-N 0.000 description 1
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- AYLRODJJLADBOB-QMMMGPOBSA-N methyl (2s)-2,6-diisocyanatohexanoate Chemical compound COC(=O)[C@@H](N=C=O)CCCCN=C=O AYLRODJJLADBOB-QMMMGPOBSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/0804—Manufacture of polymers containing ionic or ionogenic groups
- C08G18/0819—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups
- C08G18/0823—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups containing carboxylate salt groups or groups forming them
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
- C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6633—Compounds of group C08G18/42
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Abstract
Description
前記ポリウレタンポリ尿素樹脂(A)は、例えば、ポリール化合物(a1)とポリイソシアネート化合物(a2)とを、ポリオール化合物の水酸基のモル数に対し、ポリイソシアネート化合物のイソシアネート基のモル数が過剰となる条件で反応させてイソシアネート基含有プレポリマーを得た後、該プレポリマーのイソシアネート基とポリアミン化合物(a3)とを反応させて得ることができる。
カラム ;東ソー株式会社製 TSK−GUARDCOLUMN SuperHZ−L
+東ソー株式会社製 TSK−GEL SuperHZM−M×4
検出器 ;RI(示差屈折計)
データ処理;東ソー株式会社製 マルチステーションGPC−8020modelII
測定条件 ;カラム温度 40℃
溶媒 テトラヒドロフラン
流速 0.35ml/分
標準 ;単分散ポリスチレン
試料 ;樹脂固形分換算で0.2質量%のテトラヒドロフラン溶液をマイクロフィルターでろ過したもの(100μl)
カラム ; 東ソー株式会社製ガードカラムHXL−H
+東ソー株式会社製 TSKgel G5000HXL
+東ソー株式会社製 TSKgel G4000HXL
+東ソー株式会社製 TSKgel G3000HXL
+東ソー株式会社製 TSKgel G2000HXL
検出器 ; RI(示差屈折計)
データ処理:東ソー株式会社製 SC−8010
測定条件: カラム温度 40℃
溶媒 テトラヒドロフラン
流速 1.0ml/分
標準 ;ポリスチレン
試料 ;樹脂固形分換算で0.4重量%のテトラヒドロフラン溶液をマイクロフィルターでろ過したもの(100μl)
攪拌機、温度計、環流冷却器および窒素ガス導入管を備えた4つ口フラスコに、1,4−ブタンジオールと、3−メチル−1,5−ペンタンジオールの混合物(モル比=1/1)とアジピン酸とを反応させて得た数平均分子量(Mn)2,000のポリエステルジオール852.1質量部およびヘキサメチレンジイソシアネート107.4質量部を仕込み、窒素気流下に90℃で5時間反応させ、遊離イソシアネート価(イソシアネート基含有率)1.85質量%のプレポリマーを製造した後、これに酢酸エチル540質量部を加えてウレタンプレポリマーの均一溶液とした。次いで、イソホロンジアミン36.2質量部、ジ−n−ブチルアミン4.3質量部、酢酸エチル860質量部およびイソプロピルアルコール33質量部からなる混合物に、前記ウレタンプレポリマー溶液を添加し、45℃で5時間攪拌反応させて、ポリウレタンポリ尿素樹脂溶液Aを得た。得られたポリウレタンポリ尿素樹脂溶液Aは、樹脂固形分濃度が30.2質量%、B型回転粘度計(東機産業株式会社社製「TVB−10M」)を用いて測定した粘度が980mPa・s(25℃)、樹脂固形分の重量平均分子量(Mw)が100,000であった。
製造例1と同様の装置を使用し、3−メチル−1,5−ペンタンジオールとアジピン酸とを反応させて得た数平均分子量2,000のポリエステルジオール722質量部およびイソホロンジイソシアネート192.3質量部を仕込み、窒素気流下に90℃で5時間反応させ、遊離イソシアネート価4.6質量%のプレポリマーを製造した後、これに酢酸ノルマルプロピル586質量部を加えてウレタンプレポリマーの均一溶液とした。次いで、イソホロンジアミン79.2質量部、モノエタノールアミン6.5質量部、酢酸ノルマルプロピル930質量部およびイソプロピルアルコール817質量部からなる混合物に、前記ウレタンプレポリマー溶液を添加し、45℃で5時間攪拌反応させて、ポリウレタンポリ尿素樹脂溶液Bを得た。得られたポリウレタンポリ尿素樹脂溶液Bは、樹脂固形分濃度が30.0質量%、B型回転粘度計(東機産業株式会社社製「TVB−10M」)を用いて測定した粘度が590mPa・S(25℃)、樹脂固形分の重量平均分子量(Mn)が30,000であった。
参考例1と同様の装置を使用し、エチレングリコールとネオペンチルグリコールの混合物(モル比=1/1)とアジピン酸とを反応させて得た数平均分子量1,000のポリエステルジオール716質量部およびイソホロンジイソシアネート227質量部を仕込み、窒素気流下に90℃で10時間反応させ、遊離イソシアネート価2.7質量%のプレポリマーを製造した後、これに酢酸エチル557質量部を加えてウレタンプレポリマーの均一溶液とした。次いで、イソホロンジアミン57質量部、酢酸エチル843質量部およびイソプロピルアルコール933質量部からなる混合物に、前記ウレタンプレポリマー溶液を添加し、45℃で7時間攪拌反応させて、ポリウレタンポリ尿素樹脂溶液Cを得た。得られたポリウレタンポリ尿素樹脂溶液Cは、樹脂固形分濃度が30.4質量%、B型回転粘度計(東機産業株式会社社製「TVB−10M」)を用いて測定した粘度が2,230mPa・S(25℃)、樹脂固形分の重量平均分子量(Mw)が63,000であった。
参考例1と同様の装置を使用し、3−メチル−1,5−ペンタンジオールとアジピン酸とを反応させて得た数平均分子量2,000のポリエステルジオール772質量部およびイソホロンジイソシアネート167.1質量部を仕込み、窒素気流下に90℃で5時間反応させ、遊離イソシアネート価3.2質量%のプレポリマーを製造した後、これに酢酸エチル1,750質量部を加えてウレタンプレポリマーの均一溶液とした。次いで、45℃でイソプロピルアルコール583質量部、イソホロンジアミン54質量部およびジ−n−ブチルアミン6.9質量部を添加し、45℃で7時間攪拌反応させて、ポリウレタンポリ尿素樹脂溶液Dを得た。得られたポリウレタンポリ尿素樹脂溶液Dは、樹脂固形分濃度が30.2質量%、B型回転粘度計(東機産業株式会社社製「TVB−10M」)を用いて測定した粘度が550mPa・S(25℃)、樹脂固形分の重量平均分子量(Mw)が48,000であった。
・2,2−ビス(ヒドロキシメチル)ブタン酸:酸価379mgKOH/g、水酸基価758mgKOH/g
・2,2−ジメチロールプロパン酸:酸価418mgKOH/g、水酸基価837mgKOH/g
・リンゴ酸:酸価837mgKOH/g、水酸基価418mgKOH/g
製造例1で得たポリウレタンポリ尿素樹脂溶液A100質量部と、2,2−ビス(ヒドロキシメチル)ブタン酸0.05質量部とを混合し、樹脂溶液(1−1)を得た。下記の各種試験によりその性能を評価し、結果を表1に示した。
樹脂溶液(1−1)の初期粘度と、ヒドロキシカルボン酸化合物添加後の粘度とをB型回転粘度計(東機産業株式会社製「TVB−10M」)を用いて測定し、これらの粘度変化率を算出し、以下の基準で評価した。
粘度変化率(%)=[ヒドロキシカルボン酸化合物添加後の粘度(mPa・s)/初期粘度(mPa・s)]×100
○:粘度変化率が105%以下である。
△:粘度変化率が115%以下である。
×:粘度変化率が115%を超える。
樹脂溶液(1−1)の初期粘度と、40℃で一ヶ月間密栓保管した後の粘度とをB型回転粘度計(東機産業株式会社製「TVB−10M」)を用いて測定し、これらの粘度変化率を算出し、以下の基準で評価した。
粘度変化率(%)=[40℃一ヶ月保管後の粘度(mPa・s)/初期粘度(mPa・s)]×100
○:粘度変化率が90%以上である。
△:粘度変化率が70%以上90%未満である。
×:粘度変化率が70%未満である。
樹脂溶液(1−1)を40℃で一ヶ月間密栓保管した後の濁りを以下の基準で評価した。
○:濁りが無い
×:濁りが見られる
樹脂溶液(1−1)の臭気の有無を以下の評価基準で評価した。
○:酸臭気を感じない
×:酸臭気を感じる
樹脂溶液の配合を表1に示す通りとした以外は実施例1−1と同様にして樹脂溶液(1−2)〜(1−7)を得、実施例1−1と同様の評価を行った。結果を表1に示す。
樹脂溶液の配合を表2に示す通りとした以外は実施例1−1と同様にして樹脂溶液(1−8)〜(1−14)を得、実施例1−1と同様の評価を行った。結果を表2に示す。
実施例1−1で得たポリウレタンポリ尿素樹脂溶液(1−1)35質量部、酸化チタン30質量部、酢酸エチル20質量部、及びイソプロピルアルコール15質量部の混合物を練肉した後、酢酸エチル60質量部とイソプロピルアルコール40質量部との混合溶液を用いてその粘度をザーンカップ#3(株式会社離合社製「ザーン粘度計」)で16秒に調節し、印刷インキ(2−1)を得た。
前記印刷インキ(2−1)について下記各種試験によりその性能を評価し、結果を表3に示した。
印刷インキ(2−1)の初期粘度及び、40℃で一ヶ月間密栓保管した後の粘度をザーンカップ#3(株式会社離合社製「ザーン粘度計」)を用いて測定した。これらの粘度変化率を算出し、以下の評価基準で評価した。
粘度変化率(%)=[40℃一ヶ月保管後の粘度(秒)/初期粘度(秒)]×100
○:粘度変化率が90%以上である。
△:粘度変化率が70%以上90%未満である。
×:粘度変化率が70%未満である。
OPPフィルム、PETフィルム、及びナイロンフィルムに前記印刷インキ(2−1)をグラビア印刷し、印刷フィルムを得た。該印刷フィルムのインキ面にセロハン粘着テープ(ニチバン社製、12mm巾)を貼り、該テープの一端をフィルムの面に対して垂直方向に一気に剥がしたときのインキ面の状態を評価した。
○:インキ面の残りが90面積%以上
△:インキ面の残りが30面積%以上90面積%未満
×:インキ面の残りが30面積%未満
印刷インキ(2−1)を40℃で一ヶ月間密栓保管した後の着色を以下の基準で評価した。
○:ピンク色の着色変化が無い
×:ピンク色の着色変化が見られる
用いるポリウレタンポリ尿素樹脂溶液を表3に示す通りとした以外は実施例2−1と同様にして印刷インキ(2−2)〜(2−7)を得、実施例2−1と同様の評価を行った。結果を表3に示す。
印刷インキの配合を表4に示す通りとした以外は実施例2−1と同様にして印刷インキ(2−8)〜(2−14)を得、実施例2−1と同様の評価を行った。結果を表4に示す。
Claims (6)
- ポリウレタンポリ尿素樹脂(A)と、酸価が360〜450mgKOH/gの範囲であり、かつ、水酸基価が730〜900mgKOH/gの範囲であるジヒドロキシモノカルボン酸(B)と、エステル系溶剤(C1)及びアルコール系溶剤(C2)からなる群から選ばれる1種類以上の溶剤とを必須の成分として含有し、前記ポリウレタンポリ尿素樹脂(A)の不揮発分100質量部に対し、前記ジヒドロキシモノカルボン酸(B)を0.03〜5質量部となる割合で含有する樹脂組成物。
- 前記ジヒドロキシモノカルボン酸(B)が2,2−ビス(ヒドロキシメチル)ブタン酸又は2,2−ジメチロールプロパン酸である請求項1記載の樹脂組成物。
- 前記溶剤中の前記エステル系溶剤(C1)とアルコール系溶剤(C2)との質量比[(C1)/(C2)]が99/1〜30/70の範囲である請求項1記載の樹脂組成物。
- 前記エステル系溶剤(C1)が酢酸エチル又は酢酸ノルマルプロピルであり、かつ、前記アルコール系溶剤(C2)がイソプロピルアルコールである請求項1記載の樹脂組成物。
- 請求項1〜4のいずれか一つに記載の樹脂組成物を含有する印刷インキ用バインダー
- 請求項5記載の印刷インキ用バインダーを用いてなる印刷インキ
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JP6484271B2 (ja) * | 2017-03-15 | 2019-03-13 | 三洋化成工業株式会社 | 印刷インキ用バインダー及びこれを用いた印刷インキ |
JP2019006909A (ja) * | 2017-06-26 | 2019-01-17 | Dicグラフィックス株式会社 | リキッドインキ組成物 |
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