NO329114B1 - Vandige dispersjoner av epoksyharpikser, herdbar epoksyblanding og fremgangsmate for fremstilling av en vandig dispersjon - Google Patents

Vandige dispersjoner av epoksyharpikser, herdbar epoksyblanding og fremgangsmate for fremstilling av en vandig dispersjon Download PDF

Info

Publication number: NO329114B1
Authority: NO; Norway
Prior art keywords: epoxy; epoxy resin; resin; amidoamine; iii
Prior art date: 1997-08-14

Application number

NO20000685A

Other languages

English (en)

Norwegian (no)

Other versions

NO20000685L (no

NO20000685D0 (no

Inventor

Gayle Edward Back

Jimmy D Elmore

Charles John Stark

Ernest Charles Galgoci Jr

Pen-Chung Wang

Original Assignee

Shell Int Research

Priority date (The priority date 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 date listed.)

1997-08-14

Filing date

2000-02-11

Publication date

2010-08-30

1998-07-17 Priority claimed from US09/116,923 external-priority patent/US6221934B1/en

2000-02-11 Application filed by Shell Int Research filed Critical Shell Int Research

2000-02-11 Publication of NO20000685L publication Critical patent/NO20000685L/no

2000-02-11 Publication of NO20000685D0 publication Critical patent/NO20000685D0/no

2010-08-30 Publication of NO329114B1 publication Critical patent/NO329114B1/no

Links

239000003822 epoxy resin Substances 0.000 title claims abstract description 128
229920000647 polyepoxide Polymers 0.000 title claims abstract description 128
239000006185 dispersion Substances 0.000 title claims abstract description 106
239000004593 Epoxy Substances 0.000 title claims abstract description 91
239000000203 mixture Substances 0.000 title claims abstract description 56
LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 title abstract description 23
238000004519 manufacturing process Methods 0.000 title description 7
229920005989 resin Polymers 0.000 claims abstract description 93
239000011347 resin Substances 0.000 claims abstract description 93
239000004094 surface-active agent Substances 0.000 claims abstract description 79
150000001412 amines Chemical class 0.000 claims abstract description 37
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 27
239000001257 hydrogen Substances 0.000 claims abstract description 26
238000000034 method Methods 0.000 claims abstract description 19
125000001931 aliphatic group Chemical group 0.000 claims abstract description 17
125000003118 aryl group Chemical group 0.000 claims abstract description 17
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 17
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 16
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 15
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 13
125000003700 epoxy group Chemical group 0.000 claims abstract description 12
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 9
239000001301 oxygen Substances 0.000 claims abstract description 9
229910052760 oxygen Inorganic materials 0.000 claims abstract description 9
125000000217 alkyl group Chemical group 0.000 claims abstract description 8
150000002431 hydrogen Chemical group 0.000 claims abstract description 8
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 78
239000003795 chemical substances by application Substances 0.000 claims description 39
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 31
150000001875 compounds Chemical class 0.000 claims description 23
239000002253 acid Substances 0.000 claims description 21
239000003607 modifier Substances 0.000 claims description 20
238000002156 mixing Methods 0.000 claims description 18
239000007788 liquid Substances 0.000 claims description 15
230000002209 hydrophobic effect Effects 0.000 claims description 14
229920001515 polyalkylene glycol Polymers 0.000 claims description 13
150000004985 diamines Chemical class 0.000 claims description 7
125000003710 aryl alkyl group Chemical group 0.000 claims description 5
150000002148 esters Chemical class 0.000 claims description 5
239000007764 o/w emulsion Substances 0.000 claims description 5
239000002904 solvent Substances 0.000 claims description 5
229920001807 Urea-formaldehyde Polymers 0.000 claims description 3
125000002877 alkyl aryl group Chemical group 0.000 claims description 2
-1 cycloaliphatic Chemical group 0.000 abstract description 45
239000000839 emulsion Substances 0.000 abstract description 31
238000002360 preparation method Methods 0.000 abstract description 18
238000004945 emulsification Methods 0.000 abstract description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 4
239000002245 particle Substances 0.000 description 41
239000008367 deionised water Substances 0.000 description 35
229910021641 deionized water Inorganic materials 0.000 description 35
IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 34
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 30
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 28
GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 26
238000006243 chemical reaction Methods 0.000 description 23
239000003973 paint Substances 0.000 description 20
229920001223 polyethylene glycol Polymers 0.000 description 18
239000000243 solution Substances 0.000 description 18
229940106691 bisphenol a Drugs 0.000 description 17
239000000047 product Substances 0.000 description 17
239000007787 solid Substances 0.000 description 16
239000000049 pigment Substances 0.000 description 15
238000007792 addition Methods 0.000 description 14
229910052757 nitrogen Inorganic materials 0.000 description 14
239000000126 substance Substances 0.000 description 14
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 13
239000003085 diluting agent Substances 0.000 description 13
150000002118 epoxides Chemical group 0.000 description 13
150000002989 phenols Chemical class 0.000 description 13
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
SLAFUPJSGFVWPP-UHFFFAOYSA-M ethyl(triphenyl)phosphanium;iodide Chemical compound [I-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC)C1=CC=CC=C1 SLAFUPJSGFVWPP-UHFFFAOYSA-M 0.000 description 12
238000000576 coating method Methods 0.000 description 11
239000000463 material Substances 0.000 description 11
239000002202 Polyethylene glycol Substances 0.000 description 10
230000000052 comparative effect Effects 0.000 description 10
229920003986 novolac Polymers 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
239000011541 reaction mixture Substances 0.000 description 9
239000003054 catalyst Substances 0.000 description 8
VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 7
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 7
229920003180 amino resin Polymers 0.000 description 7
239000011248 coating agent Substances 0.000 description 7
238000009472 formulation Methods 0.000 description 7
238000011065 in-situ storage Methods 0.000 description 7
239000004848 polyfunctional curative Substances 0.000 description 7
YEYKMVJDLWJFOA-UHFFFAOYSA-N 2-propoxyethanol Chemical compound CCCOCCO YEYKMVJDLWJFOA-UHFFFAOYSA-N 0.000 description 6
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
238000001816 cooling Methods 0.000 description 6
QQWAKSKPSOFJFF-UHFFFAOYSA-N oxiran-2-ylmethyl 2,2-dimethyloctanoate Chemical compound CCCCCCC(C)(C)C(=O)OCC1CO1 QQWAKSKPSOFJFF-UHFFFAOYSA-N 0.000 description 6
229920000642 polymer Polymers 0.000 description 6
RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 5
229920000663 Hydroxyethyl cellulose Polymers 0.000 description 5
229920000877 Melamine resin Polymers 0.000 description 5
239000004698 Polyethylene Substances 0.000 description 5
239000000654 additive Substances 0.000 description 5
125000003277 amino group Chemical group 0.000 description 5
150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 5
238000009826 distribution Methods 0.000 description 5
125000005842 heteroatom Chemical group 0.000 description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
235000019447 hydroxyethyl cellulose Nutrition 0.000 description 5
JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 5
239000002243 precursor Substances 0.000 description 5
150000003141 primary amines Chemical class 0.000 description 5
KUBDPQJOLOUJRM-UHFFFAOYSA-N 2-(chloromethyl)oxirane;4-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound ClCC1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 KUBDPQJOLOUJRM-UHFFFAOYSA-N 0.000 description 4
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 description 4
239000002518 antifoaming agent Substances 0.000 description 4
150000007942 carboxylates Chemical class 0.000 description 4
239000007795 chemical reaction product Substances 0.000 description 4
239000000835 fiber Substances 0.000 description 4
238000010992 reflux Methods 0.000 description 4
238000004062 sedimentation Methods 0.000 description 4
125000003003 spiro group Chemical group 0.000 description 4
239000004408 titanium dioxide Substances 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
JZUHIOJYCPIVLQ-UHFFFAOYSA-N 2-methylpentane-1,5-diamine Chemical compound NCC(C)CCCN JZUHIOJYCPIVLQ-UHFFFAOYSA-N 0.000 description 3
239000004606 Fillers/Extenders Substances 0.000 description 3
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 3
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
150000001299 aldehydes Chemical class 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
239000011230 binding agent Substances 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
229920001400 block copolymer Polymers 0.000 description 3
OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 3
239000008199 coating composition Substances 0.000 description 3
239000007789 gas Substances 0.000 description 3
239000003292 glue Substances 0.000 description 3
229910017604 nitric acid Inorganic materials 0.000 description 3
229920000962 poly(amidoamine) Polymers 0.000 description 3
229920000768 polyamine Polymers 0.000 description 3
150000003254 radicals Chemical class 0.000 description 3
238000003756 stirring Methods 0.000 description 3
238000003860 storage Methods 0.000 description 3
239000000758 substrate Substances 0.000 description 3
239000002562 thickening agent Substances 0.000 description 3
GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 3
239000003039 volatile agent Substances 0.000 description 3
125000000008 (C1-C10) alkyl group Chemical group 0.000 description 2
JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 description 2
VRRDONHGWVSGFH-UHFFFAOYSA-N 2,5-diethylcyclohexane-1,4-diamine Chemical compound CCC1CC(N)C(CC)CC1N VRRDONHGWVSGFH-UHFFFAOYSA-N 0.000 description 2
WNISWKAEAPQCJQ-UHFFFAOYSA-N 2-[(2-nonylphenoxy)methyl]oxirane Chemical compound CCCCCCCCCC1=CC=CC=C1OCC1OC1 WNISWKAEAPQCJQ-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
QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 2
WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 description 2
CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 description 2
YXALYBMHAYZKAP-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptan-4-ylmethyl 7-oxabicyclo[4.1.0]heptane-4-carboxylate Chemical compound C1CC2OC2CC1C(=O)OCC1CC2OC2CC1 YXALYBMHAYZKAP-UHFFFAOYSA-N 0.000 description 2
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
241000254173 Coleoptera Species 0.000 description 2
229920003270 Cymel® Polymers 0.000 description 2
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
229920003332 Epotuf® Polymers 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-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
UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
238000005481 NMR spectroscopy Methods 0.000 description 2
IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
239000000853 adhesive Substances 0.000 description 2
230000001070 adhesive effect Effects 0.000 description 2
239000003513 alkali Substances 0.000 description 2
150000001346 alkyl aryl ethers Chemical class 0.000 description 2
125000002947 alkylene group Chemical group 0.000 description 2
229910052782 aluminium Inorganic materials 0.000 description 2
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
235000013877 carbamide Nutrition 0.000 description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
229940072282 cardura Drugs 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
229930003836 cresol Natural products 0.000 description 2
SSJXIUAHEKJCMH-UHFFFAOYSA-N cyclohexane-1,2-diamine Chemical compound NC1CCCCC1N SSJXIUAHEKJCMH-UHFFFAOYSA-N 0.000 description 2
HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
230000006378 damage Effects 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
238000004821 distillation Methods 0.000 description 2
LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
RUZYUOTYCVRMRZ-UHFFFAOYSA-N doxazosin Chemical compound C1OC2=CC=CC=C2OC1C(=O)N(CC1)CCN1C1=NC(N)=C(C=C(C(OC)=C2)OC)C2=N1 RUZYUOTYCVRMRZ-UHFFFAOYSA-N 0.000 description 2
125000004185 ester group Chemical group 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
239000011888 foil Substances 0.000 description 2
239000011521 glass Substances 0.000 description 2
KWLMIXQRALPRBC-UHFFFAOYSA-L hectorite Chemical class [Li+].[OH-].[OH-].[Na+].[Mg+2].O1[Si]2([O-])O[Si]1([O-])O[Si]([O-])(O1)O[Si]1([O-])O2 KWLMIXQRALPRBC-UHFFFAOYSA-L 0.000 description 2
NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
238000005984 hydrogenation reaction Methods 0.000 description 2
238000002329 infrared spectrum Methods 0.000 description 2
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
239000011968 lewis acid catalyst Substances 0.000 description 2
SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 2
QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
WTSXICLFTPPDTL-UHFFFAOYSA-N pentane-1,3-diamine Chemical compound CCC(N)CCN WTSXICLFTPPDTL-UHFFFAOYSA-N 0.000 description 2
239000012071 phase Substances 0.000 description 2
238000006116 polymerization reaction Methods 0.000 description 2
229920001451 polypropylene glycol Polymers 0.000 description 2
239000000843 powder Substances 0.000 description 2
239000006254 rheological additive Substances 0.000 description 2
QRUBYZBWAOOHSV-UHFFFAOYSA-M silver trifluoromethanesulfonate Chemical compound [Ag+].[O-]S(=O)(=O)C(F)(F)F QRUBYZBWAOOHSV-UHFFFAOYSA-M 0.000 description 2
ZNCPFRVNHGOPAG-UHFFFAOYSA-L sodium oxalate Chemical compound [Na+].[Na+].[O-]C(=O)C([O-])=O ZNCPFRVNHGOPAG-UHFFFAOYSA-L 0.000 description 2
229940039790 sodium oxalate Drugs 0.000 description 2
BPILDHPJSYVNAF-UHFFFAOYSA-M sodium;diiodomethanesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C(I)I BPILDHPJSYVNAF-UHFFFAOYSA-M 0.000 description 2
239000007858 starting material Substances 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
239000001993 wax Substances 0.000 description 2
239000000080 wetting agent Substances 0.000 description 2
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PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
HCNHNBLSNVSJTJ-UHFFFAOYSA-N 1,1-Bis(4-hydroxyphenyl)ethane Chemical compound C=1C=C(O)C=CC=1C(C)C1=CC=C(O)C=C1 HCNHNBLSNVSJTJ-UHFFFAOYSA-N 0.000 description 1
BOKGTLAJQHTOKE-UHFFFAOYSA-N 1,5-dihydroxynaphthalene Chemical compound C1=CC=C2C(O)=CC=CC2=C1O BOKGTLAJQHTOKE-UHFFFAOYSA-N 0.000 description 1
ZPANWZBSGMDWON-UHFFFAOYSA-N 1-[(2-hydroxynaphthalen-1-yl)methyl]naphthalen-2-ol Chemical compound C1=CC=C2C(CC3=C4C=CC=CC4=CC=C3O)=C(O)C=CC2=C1 ZPANWZBSGMDWON-UHFFFAOYSA-N 0.000 description 1
SDRZFSPCVYEJTP-UHFFFAOYSA-N 1-ethenylcyclohexene Chemical compound C=CC1=CCCCC1 SDRZFSPCVYEJTP-UHFFFAOYSA-N 0.000 description 1
DPQHRXRAZHNGRU-UHFFFAOYSA-N 2,4,4-trimethylhexane-1,6-diamine Chemical compound NCC(C)CC(C)(C)CCN DPQHRXRAZHNGRU-UHFFFAOYSA-N 0.000 description 1
LXOFYPKXCSULTL-UHFFFAOYSA-N 2,4,7,9-tetramethyldec-5-yne-4,7-diol Chemical compound CC(C)CC(C)(O)C#CC(C)(O)CC(C)C LXOFYPKXCSULTL-UHFFFAOYSA-N 0.000 description 1
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238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
LDHBWEYLDHLIBQ-UHFFFAOYSA-M iron(3+);oxygen(2-);hydroxide;hydrate Chemical compound O.[OH-].[O-2].[Fe+3] LDHBWEYLDHLIBQ-UHFFFAOYSA-M 0.000 description 1
JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
238000002955 isolation Methods 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
229920001427 mPEG Polymers 0.000 description 1
150000007974 melamines Chemical class 0.000 description 1
238000002844 melting Methods 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
QABLOFMHHSOFRJ-UHFFFAOYSA-N methyl 2-chloroacetate Chemical compound COC(=O)CCl QABLOFMHHSOFRJ-UHFFFAOYSA-N 0.000 description 1
239000011707 mineral Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
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AFFLGGQVNFXPEV-UHFFFAOYSA-N n-decene Natural products CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 1
FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
229920000847 nonoxynol Polymers 0.000 description 1
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229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
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ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical class O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
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235000020354 squash Nutrition 0.000 description 1
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239000011593 sulfur Substances 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
238000010998 test method Methods 0.000 description 1
JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
238000003878 thermal aging Methods 0.000 description 1
229920001187 thermosetting polymer Polymers 0.000 description 1
230000008719 thickening Effects 0.000 description 1
QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
150000003672 ureas Chemical class 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000004711 α-olefin Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
- C08J3/03—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in aqueous media
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2363/00—Characterised by the use of epoxy resins; Derivatives of epoxy resins

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Dispersion Chemistry (AREA)
Epoxy Resins (AREA)
Compositions Of Macromolecular Compounds (AREA)
Processes Of Treating Macromolecular Substances (AREA)
Paints Or Removers (AREA)
Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
Colloid Chemistry (AREA)
Processing Of Solid Wastes (AREA)

NO20000685A 1997-08-14 2000-02-11 Vandige dispersjoner av epoksyharpikser, herdbar epoksyblanding og fremgangsmate for fremstilling av en vandig dispersjon NO329114B1 (no)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US91148097A	1997-08-14	1997-08-14
US09/116,923 US6221934B1 (en)	1997-08-14	1998-07-17	Aqueous dispersions of epoxy resins
PCT/EP1998/005281 WO1999009089A2 (en)	1997-08-14	1998-08-13	Aqueous dispersions of epoxy resins

Publications (3)

Publication Number	Publication Date
NO20000685L NO20000685L (no)	2000-02-11
NO20000685D0 NO20000685D0 (no)	2000-02-11
NO329114B1 true NO329114B1 (no)	2010-08-30

Family

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Application Number	Title	Priority Date	Filing Date
NO20000685A NO329114B1 (no)	1997-08-14	2000-02-11	Vandige dispersjoner av epoksyharpikser, herdbar epoksyblanding og fremgangsmate for fremstilling av en vandig dispersjon

Country Status (15)

Country	Link
EP (1)	EP1003816B1 (de)
JP (1)	JP4051176B2 (de)
CN (1)	CN1100827C (de)
AT (1)	ATE229994T1 (de)
AU (1)	AU740982B2 (de)
BR (1)	BR9811164A (de)
CA (1)	CA2300169C (de)
DE (1)	DE69810304T2 (de)
DK (1)	DK1003816T3 (de)
HU (1)	HUP0104940A2 (de)
ID (1)	ID24092A (de)
IL (1)	IL133717A0 (de)
NO (1)	NO329114B1 (de)
TR (1)	TR200000381T2 (de)
WO (1)	WO1999009089A2 (de)

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US6143809A (en) *	1998-07-17	2000-11-07	Shell Oil Company	Process to prepare aqueous dispersions of epoxy resins
JP4674112B2 (ja) *	2005-04-28	2011-04-20	出光興産株式会社	エポキシ樹脂組成物及びそれを用いた光学電子部材
US8580871B2 (en) *	2010-12-13	2013-11-12	Momentive Specialty Chemicals Inc.	Epoxy systems and amine polymer systems and methods for making the same
EP2476672A1 (de) *	2010-12-22	2012-07-18	Momentive Specialty Chemicals Research Belgium S.A.	Glycidylester von alpha,alpha-verzweigten Säurezusammensetzungen
JP2014009270A (ja) *	2012-06-28	2014-01-20	Henkel Japan Ltd	水性エポキシ樹脂エマルション
TWI684609B (zh) *	2017-08-15	2020-02-11	長春人造樹脂廠股份有限公司	反應性環氧化合物及其製備方法及包含其之核-殼型環氧樹脂顆粒、水性環氧樹脂組合物及塗料組合物
WO2022211653A1 (ru) *	2021-03-29	2022-10-06	Общество с ограниченной ответственностью "НАУЧНО-ПРОИЗВОДСТВЕННАЯ ФИРМА "РЕКОН"	Способ получения водной эпоксидной дисперсии
CN116478344A (zh) *	2022-01-17	2023-07-25	万华化学集团股份有限公司	一种水性单组份环氧乳液及其制备方法
JP2026513007A (ja) *	2023-04-07	2026-04-22	Dic株式会社	水分散性エポキシ樹脂組成物、塗料及び物品

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DE3901279A1 (de) *	1989-01-18	1990-07-19	Hoechst Ag	Verwendung von polyamidoaminen als haerter fuer epoxidharze und diese enthaltende haertbare mischungen
DE4206392A1 (de) *	1992-02-29	1993-09-02	Hoechst Ag	Haertungsmittel fuer epoxidharze

1998
- 1998-08-13 DE DE69810304T patent/DE69810304T2/de not_active Expired - Lifetime
- 1998-08-13 EP EP98951306A patent/EP1003816B1/de not_active Expired - Lifetime
- 1998-08-13 BR BR9811164-7A patent/BR9811164A/pt not_active IP Right Cessation
- 1998-08-13 JP JP2000509764A patent/JP4051176B2/ja not_active Expired - Lifetime
- 1998-08-13 HU HU0104940A patent/HUP0104940A2/hu unknown
- 1998-08-13 CN CN98807958A patent/CN1100827C/zh not_active Expired - Lifetime
- 1998-08-13 DK DK98951306T patent/DK1003816T3/da active
- 1998-08-13 WO PCT/EP1998/005281 patent/WO1999009089A2/en not_active Ceased
- 1998-08-13 AU AU97385/98A patent/AU740982B2/en not_active Expired
- 1998-08-13 TR TR2000/00381T patent/TR200000381T2/xx unknown
- 1998-08-13 IL IL13371798A patent/IL133717A0/xx unknown
- 1998-08-13 ID IDW20000276A patent/ID24092A/id unknown
- 1998-08-13 CA CA002300169A patent/CA2300169C/en not_active Expired - Lifetime
- 1998-08-13 AT AT98951306T patent/ATE229994T1/de active
2000
- 2000-02-11 NO NO20000685A patent/NO329114B1/no not_active IP Right Cessation

Also Published As

Publication number	Publication date
ATE229994T1 (de)	2003-01-15
DE69810304D1 (de)	2003-01-30
EP1003816A2 (de)	2000-05-31
WO1999009089A2 (en)	1999-02-25
WO1999009089A3 (en)	1999-05-27
CA2300169A1 (en)	1999-02-25
EP1003816B1 (de)	2002-12-18
JP4051176B2 (ja)	2008-02-20
NO20000685L (no)	2000-02-11
CN1265695A (zh)	2000-09-06
DK1003816T3 (da)	2003-04-07
AU9738598A (en)	1999-03-08
CN1100827C (zh)	2003-02-05
DE69810304T2 (de)	2003-05-22
CA2300169C (en)	2008-02-05
TR200000381T2 (tr)	2000-11-21
BR9811164A (pt)	2000-07-25
IL133717A0 (en)	2001-04-30
JP2001515112A (ja)	2001-09-18
HUP0104940A2 (hu)	2002-04-29
ID24092A (id)	2000-07-06
AU740982B2 (en)	2001-11-22
NO20000685D0 (no)	2000-02-11

Legal Events

Date	Code	Title	Description
2018-09-10	MK1K	Patent expired

Publication	Publication Date	Title
US5602193A (en)	1997-02-11	Aqueous dispersions of epoxy resins
US6127459A (en)	2000-10-03	Epoxy resin curing agent-reacting acid-terminated polyalkylene glycol with excess amine-terminated polyamine-epoxy resin adduct
US6221934B1 (en)	2001-04-24	Aqueous dispersions of epoxy resins
EP1060205B1 (de)	2003-05-28	Wasserdispergierbare härtungsmittel für epoxidharze
BR112013014596B1 (pt)	2020-09-29	Composição de epóxi, revestimento termofixado, e, encolamento de fibra
US5741835A (en)	1998-04-21	Aqueous dispersions of epoxy resins
CA2337389C (en)	2008-02-26	Aqueous dispersions of epoxy resins and a process to prepare them
NO329114B1 (no)	2010-08-30	Vandige dispersjoner av epoksyharpikser, herdbar epoksyblanding og fremgangsmate for fremstilling av en vandig dispersjon
CA2820462A1 (en)	2012-06-21	Improved epoxy systems and amine polymer systems and methods for making the same
NO323443B1 (no)	2007-05-07	Fremgangsmate for fremstilling av en polykarboksylsyresammensetning.
MXPA00001132A (en)	2001-05-07	Aqueous dispersions of epoxy resins
MXPA00004427A (en)	2002-06-05	Water compatible curing agents for epoxy resins