JP2018517009A - 逆浸透モジュール用ポリウレタン接着剤 - Google Patents
逆浸透モジュール用ポリウレタン接着剤 Download PDFInfo
- Publication number
- JP2018517009A JP2018517009A JP2017553129A JP2017553129A JP2018517009A JP 2018517009 A JP2018517009 A JP 2018517009A JP 2017553129 A JP2017553129 A JP 2017553129A JP 2017553129 A JP2017553129 A JP 2017553129A JP 2018517009 A JP2018517009 A JP 2018517009A
- Authority
- JP
- Japan
- Prior art keywords
- isocyanate
- adhesive composition
- polyol
- component
- diisocyanate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000853 adhesive Substances 0.000 title claims abstract description 272
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 272
- 239000004814 polyurethane Substances 0.000 title claims abstract description 70
- 229920002635 polyurethane Polymers 0.000 title claims abstract description 70
- 238000001223 reverse osmosis Methods 0.000 title claims abstract description 57
- 239000000203 mixture Substances 0.000 claims abstract description 242
- 239000012948 isocyanate Substances 0.000 claims abstract description 203
- 229920005862 polyol Polymers 0.000 claims abstract description 201
- 150000003077 polyols Chemical class 0.000 claims abstract description 201
- 150000002513 isocyanates Chemical class 0.000 claims abstract description 165
- 239000012528 membrane Substances 0.000 claims abstract description 92
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims abstract description 36
- 238000002156 mixing Methods 0.000 claims abstract description 35
- 239000003921 oil Substances 0.000 claims abstract description 24
- 239000002904 solvent Substances 0.000 claims abstract description 19
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 12
- 239000003085 diluting agent Substances 0.000 claims abstract description 11
- 239000004359 castor oil Substances 0.000 claims description 77
- 235000019438 castor oil Nutrition 0.000 claims description 77
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 claims description 77
- -1 carbodiimide modified diphenylmethane diisocyanate Chemical class 0.000 claims description 70
- 229920000570 polyether Polymers 0.000 claims description 49
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 48
- 150000002009 diols Chemical class 0.000 claims description 39
- 239000004014 plasticizer Substances 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 30
- 150000002148 esters Chemical class 0.000 claims description 25
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 claims description 25
- 229960003656 ricinoleic acid Drugs 0.000 claims description 25
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 claims description 24
- 239000005062 Polybutadiene Substances 0.000 claims description 23
- 229920002857 polybutadiene Polymers 0.000 claims description 23
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 claims description 20
- 239000000178 monomer Substances 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 230000035515 penetration Effects 0.000 claims description 15
- 229920002367 Polyisobutene Polymers 0.000 claims description 14
- 239000002274 desiccant Substances 0.000 claims description 12
- DJOWTWWHMWQATC-KYHIUUMWSA-N Karpoxanthin Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1(O)C(C)(C)CC(O)CC1(C)O)C=CC=C(/C)C=CC2=C(C)CC(O)CC2(C)C DJOWTWWHMWQATC-KYHIUUMWSA-N 0.000 claims description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 11
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- 150000004985 diamines Chemical class 0.000 claims description 10
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 10
- 125000003277 amino group Chemical group 0.000 claims description 9
- HIFVAOIJYDXIJG-UHFFFAOYSA-N benzylbenzene;isocyanic acid Chemical class N=C=O.N=C=O.C=1C=CC=CC=1CC1=CC=CC=C1 HIFVAOIJYDXIJG-UHFFFAOYSA-N 0.000 claims description 9
- 238000001914 filtration Methods 0.000 claims description 9
- 239000000047 product Substances 0.000 claims description 9
- 238000005809 transesterification reaction Methods 0.000 claims description 7
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 claims description 6
- 229920005906 polyester polyol Polymers 0.000 claims description 5
- CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-UHFFFAOYSA-N 0.000 claims description 4
- ATOUXIOKEJWULN-UHFFFAOYSA-N 1,6-diisocyanato-2,2,4-trimethylhexane Chemical compound O=C=NCCC(C)CC(C)(C)CN=C=O ATOUXIOKEJWULN-UHFFFAOYSA-N 0.000 claims description 4
- 229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 claims description 4
- AFVMPODRAIDZQC-UHFFFAOYSA-N 1-isocyanato-2-(isocyanatomethyl)cyclopentane Chemical compound O=C=NCC1CCCC1N=C=O AFVMPODRAIDZQC-UHFFFAOYSA-N 0.000 claims description 4
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 4
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 4
- ROHUXHMNZLHBSF-UHFFFAOYSA-N 1,4-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1CCC(CN=C=O)CC1 ROHUXHMNZLHBSF-UHFFFAOYSA-N 0.000 claims description 3
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 claims description 3
- VLNDSAWYJSNKOU-UHFFFAOYSA-N 1-isocyanato-4-[(4-isocyanato-3-methylcyclohexyl)methyl]-2-methylcyclohexane Chemical compound C1CC(N=C=O)C(C)CC1CC1CC(C)C(N=C=O)CC1 VLNDSAWYJSNKOU-UHFFFAOYSA-N 0.000 claims description 3
- 125000005442 diisocyanate group Chemical group 0.000 claims description 3
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 3
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 claims description 3
- ABZIUADBEUVQIX-UHFFFAOYSA-N 1,3-diisocyanatobenzene 1,4-diisocyanatobenzene Chemical compound C1(=CC(=CC=C1)N=C=O)N=C=O.C1(=CC=C(C=C1)N=C=O)N=C=O ABZIUADBEUVQIX-UHFFFAOYSA-N 0.000 claims description 2
- 238000007385 chemical modification Methods 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol group Chemical group OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 23
- 239000002253 acid Substances 0.000 description 20
- 238000012360 testing method Methods 0.000 description 19
- 235000019198 oils Nutrition 0.000 description 18
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 16
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical class OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 14
- 239000002518 antifoaming agent Substances 0.000 description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 13
- 239000000654 additive Substances 0.000 description 11
- 150000004982 aromatic amines Chemical class 0.000 description 11
- 230000003068 static effect Effects 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 9
- 230000008595 infiltration Effects 0.000 description 9
- 238000001764 infiltration Methods 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 8
- 235000011187 glycerol Nutrition 0.000 description 8
- 230000002829 reductive effect Effects 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 7
- 150000001412 amines Chemical group 0.000 description 7
- 239000003925 fat Substances 0.000 description 7
- 239000002808 molecular sieve Substances 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- 229920001451 polypropylene glycol Polymers 0.000 description 7
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 7
- NXQMCAOPTPLPRL-UHFFFAOYSA-N 2-(2-benzoyloxyethoxy)ethyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCCOCCOC(=O)C1=CC=CC=C1 NXQMCAOPTPLPRL-UHFFFAOYSA-N 0.000 description 6
- 230000000996 additive effect Effects 0.000 description 6
- YCZJVRCZIPDYHH-UHFFFAOYSA-N ditridecyl benzene-1,2-dicarboxylate Chemical compound CCCCCCCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCCCCCCC YCZJVRCZIPDYHH-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000006254 rheological additive Substances 0.000 description 6
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 6
- 229910019142 PO4 Inorganic materials 0.000 description 5
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 5
- 239000012973 diazabicyclooctane Substances 0.000 description 5
- 239000010452 phosphate Substances 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 239000013008 thixotropic agent Substances 0.000 description 5
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- ZFOZVQLOBQUTQQ-UHFFFAOYSA-N Tributyl citrate Chemical compound CCCCOC(=O)CC(O)(C(=O)OCCCC)CC(=O)OCCCC ZFOZVQLOBQUTQQ-UHFFFAOYSA-N 0.000 description 4
- CVPZXHCZKMFVOZ-UHFFFAOYSA-N [4-(benzoyloxymethyl)cyclohexyl]methyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC(CC1)CCC1COC(=O)C1=CC=CC=C1 CVPZXHCZKMFVOZ-UHFFFAOYSA-N 0.000 description 4
- SAOKZLXYCUGLFA-UHFFFAOYSA-N bis(2-ethylhexyl) adipate Chemical compound CCCCC(CC)COC(=O)CCCCC(=O)OCC(CC)CCCC SAOKZLXYCUGLFA-UHFFFAOYSA-N 0.000 description 4
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 4
- ZFMQKOWCDKKBIF-UHFFFAOYSA-N bis(3,5-difluorophenyl)phosphane Chemical compound FC1=CC(F)=CC(PC=2C=C(F)C=C(F)C=2)=C1 ZFMQKOWCDKKBIF-UHFFFAOYSA-N 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- 238000004140 cleaning Methods 0.000 description 4
- 230000003204 osmotic effect Effects 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- 235000013772 propylene glycol Nutrition 0.000 description 4
- 239000003549 soybean oil Substances 0.000 description 4
- 235000012424 soybean oil Nutrition 0.000 description 4
- 241000894007 species Species 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Chemical compound CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 235000010469 Glycine max Nutrition 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 3
- 239000011324 bead Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- JFCQEDHGNNZCLN-UHFFFAOYSA-N glutaric acid Chemical compound OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 3
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 239000005056 polyisocyanate Substances 0.000 description 3
- 229920001228 polyisocyanate Polymers 0.000 description 3
- 235000002639 sodium chloride Nutrition 0.000 description 3
- 125000006850 spacer group Chemical group 0.000 description 3
- 235000015112 vegetable and seed oil Nutrition 0.000 description 3
- 239000008158 vegetable oil Substances 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- ZWVMLYRJXORSEP-UHFFFAOYSA-N 1,2,6-Hexanetriol Chemical compound OCCCCC(O)CO ZWVMLYRJXORSEP-UHFFFAOYSA-N 0.000 description 2
- XWAMHGPDZOVVND-UHFFFAOYSA-N 1,2-octadecanediol Chemical compound CCCCCCCCCCCCCCCCC(O)CO XWAMHGPDZOVVND-UHFFFAOYSA-N 0.000 description 2
- XSCLFFBWRKTMTE-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1CCCC(CN=C=O)C1 XSCLFFBWRKTMTE-UHFFFAOYSA-N 0.000 description 2
- LFSYUSUFCBOHGU-UHFFFAOYSA-N 1-isocyanato-2-[(4-isocyanatophenyl)methyl]benzene Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=CC=C1N=C=O LFSYUSUFCBOHGU-UHFFFAOYSA-N 0.000 description 2
- RWLALWYNXFYRGW-UHFFFAOYSA-N 2-Ethyl-1,3-hexanediol Chemical compound CCCC(O)C(CC)CO RWLALWYNXFYRGW-UHFFFAOYSA-N 0.000 description 2
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-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
- GPZYYYGYCRFPBU-UHFFFAOYSA-N 6-Hydroxyflavone Chemical compound C=1C(=O)C2=CC(O)=CC=C2OC=1C1=CC=CC=C1 GPZYYYGYCRFPBU-UHFFFAOYSA-N 0.000 description 2
- YPIFGDQKSSMYHQ-UHFFFAOYSA-N 7,7-dimethyloctanoic acid Chemical compound CC(C)(C)CCCCCC(O)=O YPIFGDQKSSMYHQ-UHFFFAOYSA-N 0.000 description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
- IRIAEXORFWYRCZ-UHFFFAOYSA-N Butylbenzyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCC1=CC=CC=C1 IRIAEXORFWYRCZ-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
- KCXZNSGUUQJJTR-UHFFFAOYSA-N Di-n-hexyl phthalate Chemical compound CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCC KCXZNSGUUQJJTR-UHFFFAOYSA-N 0.000 description 2
- ZVFDTKUVRCTHQE-UHFFFAOYSA-N Diisodecyl phthalate Chemical compound CC(C)CCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC(C)C ZVFDTKUVRCTHQE-UHFFFAOYSA-N 0.000 description 2
- UDSFAEKRVUSQDD-UHFFFAOYSA-N Dimethyl adipate Chemical compound COC(=O)CCCCC(=O)OC UDSFAEKRVUSQDD-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical class OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- IPRJXAGUEGOFGG-UHFFFAOYSA-N N-butylbenzenesulfonamide Chemical compound CCCCNS(=O)(=O)C1=CC=CC=C1 IPRJXAGUEGOFGG-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
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- NSOXQYCFHDMMGV-UHFFFAOYSA-N Tetrakis(2-hydroxypropyl)ethylenediamine Chemical group CC(O)CN(CC(C)O)CCN(CC(C)O)CC(C)O NSOXQYCFHDMMGV-UHFFFAOYSA-N 0.000 description 2
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- 150000001278 adipic acid derivatives Chemical class 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical class O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
- IHTSDBYPAZEUOP-UHFFFAOYSA-N bis(2-butoxyethyl) hexanedioate Chemical compound CCCCOCCOC(=O)CCCCC(=O)OCCOCCCC IHTSDBYPAZEUOP-UHFFFAOYSA-N 0.000 description 2
- SCABKEBYDRTODC-UHFFFAOYSA-N bis[2-(2-butoxyethoxy)ethyl] hexanedioate Chemical compound CCCCOCCOCCOC(=O)CCCCC(=O)OCCOCCOCCCC SCABKEBYDRTODC-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 150000001860 citric acid derivatives Chemical class 0.000 description 2
- 239000000498 cooling water Substances 0.000 description 2
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Classifications
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Abstract
Description
(式中、「モル数NCO」は、多成分ポリウレタン組成物中のイソシアネート基の総モル数であり、「モル数OH」は、多成分ポリウレタン組成物中の、水以外の源に由来するOH基の総モル数であり(アルコールおよびカルボン酸に由来するOH基を含む)、「モル数HOH」は、多成分ポリウレタン組成物中の、存在する任意の水に由来するOH基の総モル数であり、これは、水のモル数の2倍であり、「モル数NH」は、反応混合物中の任意のNH基のモルである)に従って計算される「化学量論」を特徴とすることができる。化学量論は、当分野において使用されることが多い、「イソシアネート指数」に関連し、これは、化学量論の100倍に等しい。多成分ポリウレタン組成物の、イソシアネート基とヒドロキシル基のモル比が1:1であり、かつ該ポリウレタン混合物中に水またはNH基が存在しない場合、その化学量論は、1:1であり、イソシアネート指数は100となる。本接着剤組成物は、0.9:1〜1.25:1、詳細には1:1〜1.2:1、より詳細には1:1〜1.1:1の化学量論を有することができる。
第1のイソシアネートと少なくとも1つのポリオールとの反応生成物を含むイソシアネート基含有プレポリマー、および第1のイソシアネート、少なくとも1つのポリオールおよびイソシアネート基含有プレポリマーと本質的に反応しない第2のイソシアネートを含む第1の成分;ならびに少なくとも2つのポリオールを含む第2の成分を含み、希釈剤である油および溶媒を本質的に含まない、接着剤組成物。
具体的な原料および量は、以下の表3に提示されている。ヒマシ油の含水量は、≦0.04重量%であった。撹拌、真空、加熱および冷却ができるよう装備されているジャケット付き反応容器を使用前に洗浄し、乾燥した。次に、秤量した第1のイソシアネート、次に消泡剤および場合により可塑剤、塩化ベンゾイル、抗酸化剤、および流動化および平滑化用添加物を添加した。撹拌しながら、必要に応じて、ジャケットに冷却水を循環させて、90モル%(イソシアネートに対して)のポリオールを加え、温度が85℃を超えないようにした。ポリオールをすべて添加した後、冷却水を止め、容器を真空下(約27インチHg)で密封し、次に、この容器を80〜85℃の蒸気により3時間、加熱して、プレポリマーを形成させた。この容器を70℃未満に冷却し、次に、NCO含有量(ASTM D2572)について試料を分析した。分析したNCO含有量に基づいて、次に、プレポリマー中の工程中NCO含有量を所望のレベルまで調節するために必要なポリオールまたは第1のイソシアネートの追加分の量を算出した。次に、第1のポリオールまたは第1のイソシアネートの追加分の量を加え、さらに2時間、反応させた。一旦、工程中NCO含有量の目標に到達すると、この容器を70℃未満になるまで冷却した。最終的な目標NCO含有量に対する第2のポリイソシアネートの計算量分を加え、撹拌を1時間、継続した。一旦、最終NCO含有量の目標に到達すると、プレポリマーを200マイクロメートルのフィルターバッグでろ過した。
具体的な原料および量は、表1に提示されている。撹拌、真空、加熱および冷却を行うよう装備されているジャケット付き反応容器を使用前に洗浄し、乾燥した。表3に一覧表示されている量のポリオール、DOA、MFPを反応容器に加え、含水量が≦0.04重量%になるまで、この容器の内容物をストリッピングした。この内容物が100°F未満になるまで冷却した。モレキュラーシーブ、ヒュームドシリカ、触媒およびD230を加え、この混合物を45分間、高せん断で撹拌した。可使時間を決定するため、この混合物をサンプリングした。追加の触媒を100°F未満で加え、この混合物を30分間、ブレンドし、この時間で、200グラムの質量の場合、可使時間は25℃で約25分となった。
プレポリマー(成分A)100重量部を、表3に一覧表示されている成分Bの量と、25℃で混合した。0.37インチの内径、14.2インチの長さおよび40個の混合エレメントを有するプラスチック製静的混合用管内に取り付けられている、空気圧で作動するツインスナッファーバルブ(snuffer valve)からなるNordson静的ミキサーにより、成分Aと成分Bをポンプ注入することにより混合を行った。一旦、基材に施用すると、接着剤組成物を25℃で硬化させた。成分AおよびB、ならびに成分AおよびBを混合して硬化させることにより得られたポリウレタン接着剤の物理特性が表3にまとめられている。
プレポリマー(成分A)、成分Bの調製、ならびに成分Aおよび成分Bの混合に関する一般手順が上に記載されている。本接着剤組成物が表5にまとめられており、成分AおよびB、ならびに成分AおよびBを混合して硬化させることにより得られたポリウレタン接着剤の物理特性が表3にまとめられている。
この評価に、半透膜、ならびに不織布スクリム層および多孔性熱可塑性ポリマー層を備えた多孔性裏張りを備えた逆浸透膜(AG LF Seriesの逆浸透膜、GE Water&Process Technologiesから入手可能、Trevose、PA、米国)を使用した。カートリッジを並べて使用し、実施例(Ex.)4の接着剤組成物のビーズを多孔性裏張りに施用し、室温で24時間、硬化させた。24時間後、この逆浸透膜を評価して、多孔性裏張りに浸透する接着剤のレベルを決定した。接着剤組成物の浸透は、該接着剤組成物が、表7に示されている通り、半透膜層まで多孔性裏張りに浸透した領域の割合を目視評価することにより、「なし」から「優秀」までランク付けした。
本発明の接着剤組成物は、実施例14において例示されている通り、多孔性裏張りまたは逆浸透膜の浸透に良好ないし優れていることを示すだけではなく、本発明の組成物は浸透によるブリスタリングもなくすことができる。評価は、以下の通り行った。不織布スクリム層、多孔性熱可塑性ポリマー層および薄い半透層を備えた市販の逆浸透膜(GE Water&Process Technologies(Trevose、PA、米国)から入手可能なAG LF Series逆浸透膜)から8×8インチの試料を裁断した。市販の浸透スペーサーシートから8×4インチの試料を裁断した。逆浸透膜の試料を半分におり、その結果、半透層が外側になり、不織布スクリム層は内側になった。浸透スペーサー試料は、織り込んだ膜の内側に置いた。静的ミキサーを使用して接着剤組成物の試料を調製した。一旦、圧縮された接着剤の1×4インチの面積を作製するのに十分な新しく混合した接着剤のビーズを浸透スペーサーに施用して、折り込んだ膜を閉じた。実験室台の上で静置した封筒の上にガラス窓を置き、圧縮して均一な接着剤厚さを作製した。この接着剤を25℃で2〜3日間、硬化させた。ブリスタリングに及ぼす接着剤組成物の効果は、表8に示されている通り、脱イオン水中および飽和海水塩溶液中に逆浸透膜を交互に浸漬することにより評価した。
抽出可能な芳香族アミン含有量は、70℃において2時間、50重量%の水性エタノールを用いてポリウレタン接着剤を逐次、接触させることにより測定した。結果が表10にまとめられている。これらの結果は、ポリウレタン接着剤10センチメートル(cm)あたり、芳香族アミンのマイクログラム数(μg)として表す。
Claims (30)
- 第1のイソシアネートと少なくとも1つのポリオールとの反応生成物を含む、イソシアネート基含有プレポリマー、および
第1のイソシアネート、少なくとも1つのポリオールおよびイソシアネート基含有プレポリマーと本質的に反応しない第2のイソシアネート
を含む、第1の成分と、
少なくとも2つのポリオールを含む第2の成分と、
を含む、接着剤組成物であって、
希釈剤である油および溶媒を本質的に含まない、接着剤組成物。 - 第2のイソシアネートが、第1のイソシアネートと同一である、請求項1に記載の接着剤組成物。
- ポリブタジエンジオールおよびポリイソブチレンジオールが、第2の成分に存在しない、請求項1または2に記載の接着剤組成物。
- ポリブタジエンジオールおよびポリイソブチレンジオールが、第1の成分に存在しない、請求項1〜3のいずれかに記載の接着剤組成物。
- 接着剤組成物の総重量に対して、0.5〜35重量%の可塑剤をさらに含む、請求項1〜4のいずれかに記載の接着剤組成物。
- ASTM D2572に準拠して測定すると、ポリウレタン組成物の第1の成分が、該第1の成分の総重量に対して、10〜35重量%の総NCO含有量を有する、請求項1〜5のいずれかに記載の接着剤組成物。
- 第1のイソシアネートおよび第2のイソシアネートが、独立して、1,4−テトラメチレンジイソシアネート、1,6−ヘキサメチレンジイソシアネート、2,2,4−トリメチル−1,6−ヘキサメチレンジイソシアネート、1,12−ドデカメチレンジイソシアネート、シクロヘキサン−1,3−ジイソシアネートおよびシクロヘキサン−1,4−ジイソシアネート、1−イソシアナト−2−イソシアナトメチルシクロペンタン、1−イソシアナト−3−イソシアナトメチル−3,5,5−トリメチル−シクロヘキサン、4,4’−ジシクロヘキシルメタンジイソシアネート、2,4’−ジシクロヘキシルメタンジイソシアネート、1,3−ビス(シクロヘキシル)ジイソシアネート、1,4−ビス−(イソシアナトメチル)−シクロヘキサン、ビス(4−イソシアナト−3−メチル−シクロヘキシル)メタン、1−イソシアナト−1−メチル−4(3)−イソシアナトメチルシクロヘキサン、α,α,α’,α’−テトラメチル−1,3−キシリレンジイソシアネート、α,α,α’,α’−テトラメチル−1,4−キシリレンジイソシアネート、2,4−ヘキサヒドロトルエンジイソシアネート、2,6−ヘキサヒドロトルエンジイソシアネート、1,3−フェニレンジイソシアネート、1,4−フェニレンジイソシアネート、2,4−トルエンジイソシアネート、2,6−トルエンジイソシアネート、2,4−ジフェニルメタンジイソシアネート、1,5−ジイソシアナトナフタレン、4,4’−ジフェニルメタンジイソシアネート、上述のイソシアネートの少なくとも1つの化学修飾物、上述のイソシアネートの少なくとも1つとジオールまたはジアミンとの反応から誘導されるプレポリマー、または上述のイソシアネートの少なくとも1つを含む組合せである、請求項1〜6のいずれかに記載の接着剤組成物。
- 第1のイソシアネートおよび第2のイソシアネートが、独立して、ジフェニルメタンジイソシアネートモノマー、1分子あたり平均が2超および4以下のイソシアネート基を有する修飾ジフェニルメタンジイソシアネート、または上述のイソシアネートの少なくとも1つを含む組合せである、請求項1〜6のいずれかに記載の接着剤組成物。
- 第1のイソシアネートおよび第2のイソシアネートが、独立して、カルボジイミド修飾ジフェニルメタンジイソシアネート、ジフェニルメタンジイソシアネートとジオールまたはジアミンとの反応から誘導されるプレポリマー、または上述のイソシアネートの少なくとも1つを含む組合せから選択される修飾ジフェニルメタンジイソシアネートである、請求項1〜6のいずれかに記載の接着剤組成物。
- 第2の成分の少なくとも2つのポリオールが、ヒマシ油、ヒマシ油誘導体、リシノール酸のエステル、ポリエーテルポリオール、天然油に由来するポリオール、脂肪に由来するポリオール、ポリエーテルポリオール、ポリラクトン、ポリエステルポリオール、ポリブタジエンポリオール、ポリイソブチレンジオール、アミン官能基を有するポリオール、または上述のポリオールの少なくとも1つを含む組合せを含む、請求項1〜9のいずれかに記載の接着剤組成物。
- 第2の成分の少なくとも2つのポリオールが、ポリエーテルポリオール、ヒマシ油、ヒマシ油誘導体、リシノール酸のエステル、アミン官能基を有するポリオール、または上述のポリオールの少なくとも2つを含む組合せを含む、請求項1〜9のいずれかに記載の接着剤組成物。
- 第1の成分の少なくとも1つのポリオールが、ヒマシ油、ヒマシ油誘導体、リシノール酸のエステル、ポリエーテルポリオール、天然油に由来するポリオール、脂肪に由来するポリオール、ポリエーテルポリオール、ポリラクトン、ポリエステルポリオール、ポリブタジエンポリオール、ポリイソブチレンジオール、アミン官能基を有するポリオール、または上述のポリオールの少なくとも1つを含む組合せを含む、請求項1〜11のいずれかに記載の接着剤組成物。
- 第1の成分の少なくとも1つのポリオールが、ヒマシ油、ヒマシ油誘導体、リシノール酸のエステル、ポリエーテルポリオール、ポリブタジエンポリオール、ポリイソブチレンジオール、または上述のポリオールの少なくとも1つを含む組合せを含む、請求項1〜11のいずれかに記載の接着剤組成物。
- 第1の成分の少なくとも1つのポリオールが、ヒマシ油またはヒマシ油誘導体からなる、請求項1〜11のいずれかに記載の接着剤組成物。
- 第1の成分の少なくとも1つのポリオールが、ヒマシ油またはヒマシ油誘導体、およびポリエーテルジオールを含む、請求項1〜11のいずれかに記載の接着剤組成物。
- 第1の成分の少なくとも1つのポリオールがテトロールからなる、請求項1〜11のいずれかに記載の接着剤組成物。
- 第1の成分の少なくとも1つのポリオールがポリブタジエンポリオールからなる、請求項1〜11のいずれかに記載の接着剤組成物。
- 第2の成分の少なくとも2つのポリオールが、ヒマシ油、ヒマシ油誘導体、リシノール酸のエステル、天然油から誘導されるポリオール、ポリエーテルポリオール、または上述のポリオールの少なくとも2つを含む組合せを含む、請求項1〜9および12〜13のいずれかに記載の接着剤組成物。
- 第2の成分の少なくとも2つのポリオールが、ヒマシ油とペンタエリスリトールおよびポリエーテルトリオールとのエステル交換生成物を含む、請求項1〜9および12〜13のいずれかに記載の接着剤組成物。
- 第2の成分の少なくとも2つのポリオールが、ヒマシ油、ヒマシ油とペンタエリスリトールとのエステル交換生成物、天然油から誘導されるポリオール、ポリエーテルテトロール、または上述のポリオールの少なくとも1つを含む組合せを含む、請求項1〜9および12〜13のいずれかに記載の接着剤組成物。
- 第2の成分の少なくとも2つのポリオールが、ヒマシ油、ポリエーテルテトロール、アミン官能基を有するポリオール、または上述のポリオールの少なくとも2つを含む組合せを含む、請求項1〜9および12〜13のいずれかに記載の接着剤組成物。
- 第1のイソシアネートが芳香族イソシアネートを含み、第2のイソシアネートが脂肪族イソシアネートを含む、請求項1〜21のいずれかに記載の接着剤組成物。
- 第1のイソシアネートが芳香族イソシアネートを含み、第2のイソシアネートが、第2のイソシアネートの総重量に対して、1〜50重量%の脂肪族イソシアネート、および49〜50重量%の芳香族イソシアネートを含む、請求項1〜7および10〜22のいずれかに記載の接着剤組成物。
- 乾燥剤をさらに含む、請求項1〜23のいずれかに記載の接着剤組成物。
- 請求項1〜24のいずれかに記載の接着剤組成物の第1の成分および第2の成分を、第1の成分と第2の成分との1:1〜1.2:1の重量比で混合して、混合物を形成し、この混合物を硬化することにより作製される、ポリウレタン接着剤。
- 請求項25に記載のポリウレタン接着剤を含む物品。
- 物品が半透膜をさらに備え、ポリウレタン接着剤が半透膜に接着する、請求項26に記載の物品。
- 逆浸透モジュールである、請求項27に記載の物品。
- この方法に従わない場合の半透膜の浸透によるブリスタリングを防止または低減する方法であって、
請求項1に記載の接着剤組成物を形成するステップ、
接着剤組成物の第1の成分および第2の成分を混合して混合物を形成するステップ、
この混合物を、半透膜を多孔性支持体に固定するのに十分な量で半透膜に施用するステップ、
この混合物を硬化させてポリウレタン接着剤を形成するステップ、および
逆浸透により溶媒を半透膜に通してろ過するステップ
を含み、
ポリウレタン接着剤が、半透膜の浸透によるブリスタリングを防止または低減する、
方法。 - 第2の反応性イソシアネート種を有するイソシアネート含有プレポリマーを形成する方法であって、
第1のイソシアネートおよび少なくとも1つのポリオールを反応させて、イソシアネート含有プレポリマーを形成させるステップ、および
イソシアネート含有プレポリマーと第2のイソシアネートとを混合するステップ
を含み、
第2のイソシアネートが、第1のイソシアネート、少なくとも1つのポリオールおよびイソシアネート基含有プレポリマーと本質的に反応しない、
方法。
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KR20170138468A (ko) | 2017-12-15 |
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JP6711503B2 (ja) | 2020-06-17 |
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CA2982120C (en) | 2023-08-15 |
US20160298009A1 (en) | 2016-10-13 |
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HUE048985T2 (hu) | 2020-09-28 |
US10865333B2 (en) | 2020-12-15 |
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