CA1113643A - Method of water-solubilizing high performance polyether epoxide resins, the solubilized resins and thermoset, hydrophobic coatings derived therefrom - Google Patents
Method of water-solubilizing high performance polyether epoxide resins, the solubilized resins and thermoset, hydrophobic coatings derived therefromInfo
- Publication number
- CA1113643A CA1113643A CA293,737A CA293737A CA1113643A CA 1113643 A CA1113643 A CA 1113643A CA 293737 A CA293737 A CA 293737A CA 1113643 A CA1113643 A CA 1113643A
- Authority
- CA
- Canada
- Prior art keywords
- water
- epoxide
- formula
- reaction
- groups
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 229920005989 resin Polymers 0.000 title claims abstract description 76
- 239000011347 resin Substances 0.000 title claims abstract description 76
- 238000000034 method Methods 0.000 title claims abstract description 45
- 238000000576 coating method Methods 0.000 title claims abstract description 30
- 239000004721 Polyphenylene oxide Substances 0.000 title claims abstract description 10
- 229920000570 polyether Polymers 0.000 title claims abstract description 9
- 230000002209 hydrophobic effect Effects 0.000 title claims abstract description 7
- 229920000647 polyepoxide Polymers 0.000 title claims description 6
- 229920001187 thermosetting polymer Polymers 0.000 title 1
- 150000002118 epoxides Chemical class 0.000 claims abstract description 142
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 130
- 229910001868 water Inorganic materials 0.000 claims abstract description 128
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims abstract description 113
- 239000000203 mixture Substances 0.000 claims abstract description 72
- 235000011007 phosphoric acid Nutrition 0.000 claims abstract description 70
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 22
- 150000002148 esters Chemical class 0.000 claims abstract description 16
- 230000002378 acidificating effect Effects 0.000 claims abstract description 13
- 239000011248 coating agent Substances 0.000 claims abstract description 12
- 239000004634 thermosetting polymer Substances 0.000 claims abstract description 4
- 238000006243 chemical reaction Methods 0.000 claims description 103
- 239000000047 product Substances 0.000 claims description 88
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 54
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 52
- 239000000463 material Substances 0.000 claims description 42
- 239000007795 chemical reaction product Substances 0.000 claims description 40
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 37
- 125000000466 oxiranyl group Chemical group 0.000 claims description 34
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 33
- -1 glycidyloxy group Chemical group 0.000 claims description 28
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 27
- 229960004838 phosphoric acid Drugs 0.000 claims description 27
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 25
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 25
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 23
- 230000008569 process Effects 0.000 claims description 23
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 19
- 150000001412 amines Chemical class 0.000 claims description 18
- 238000006460 hydrolysis reaction Methods 0.000 claims description 17
- 125000003342 alkenyl group Chemical group 0.000 claims description 16
- 230000007062 hydrolysis Effects 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 12
- 150000002170 ethers Chemical class 0.000 claims description 12
- 238000010438 heat treatment Methods 0.000 claims description 11
- 229930185605 Bisphenol Natural products 0.000 claims description 9
- 229910019142 PO4 Inorganic materials 0.000 claims description 9
- 125000002947 alkylene group Chemical group 0.000 claims description 9
- 239000000758 substrate Substances 0.000 claims description 9
- 239000004593 Epoxy Substances 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 6
- 125000004450 alkenylene group Chemical group 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 claims description 5
- 150000001298 alcohols Chemical class 0.000 claims description 5
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 5
- 239000003822 epoxy resin Substances 0.000 claims description 5
- 229920003986 novolac Polymers 0.000 claims description 5
- 150000002989 phenols Chemical class 0.000 claims description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 4
- 239000010452 phosphate Substances 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 150000003626 triacylglycerols Chemical class 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000002015 acyclic group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
- 235000011187 glycerol Nutrition 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000006658 (C1-C15) hydrocarbyl group Chemical group 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims 1
- MALIONKMKPITBV-UHFFFAOYSA-N 2-(3-chloro-4-hydroxyphenyl)-n-[2-(4-sulfamoylphenyl)ethyl]acetamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1CCNC(=O)CC1=CC=C(O)C(Cl)=C1 MALIONKMKPITBV-UHFFFAOYSA-N 0.000 claims 1
- YJVYUYHRSAACOT-UHFFFAOYSA-N 5-propyl-7-oxabicyclo[4.1.0]hepta-1,3,5-triene Chemical compound CCCC1=CC=CC2=C1O2 YJVYUYHRSAACOT-UHFFFAOYSA-N 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical class C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 claims 1
- JYNZIOFUHBJABQ-UHFFFAOYSA-N allyl-{6-[3-(4-bromo-phenyl)-benzofuran-6-yloxy]-hexyl-}-methyl-amin Chemical compound C=1OC2=CC(OCCCCCCN(C)CC=C)=CC=C2C=1C1=CC=C(Br)C=C1 JYNZIOFUHBJABQ-UHFFFAOYSA-N 0.000 claims 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 claims 1
- 150000003839 salts Chemical class 0.000 abstract description 11
- 238000009736 wetting Methods 0.000 abstract description 8
- 125000004849 alkoxymethyl group Chemical group 0.000 abstract description 3
- 229920000642 polymer Polymers 0.000 abstract description 3
- 125000000524 functional group Chemical group 0.000 abstract description 2
- 239000002253 acid Substances 0.000 description 97
- 239000002585 base Substances 0.000 description 58
- 239000006185 dispersion Substances 0.000 description 52
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 48
- 239000002904 solvent Substances 0.000 description 44
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 41
- 239000000243 solution Substances 0.000 description 33
- 239000011541 reaction mixture Substances 0.000 description 30
- 150000005690 diesters Chemical group 0.000 description 23
- 239000007787 solid Substances 0.000 description 21
- 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 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- 230000000694 effects Effects 0.000 description 19
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 18
- 238000001723 curing Methods 0.000 description 18
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 16
- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 description 15
- 239000012429 reaction media Substances 0.000 description 14
- 238000009835 boiling Methods 0.000 description 13
- 238000006386 neutralization reaction Methods 0.000 description 13
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 12
- 125000003827 glycol group Chemical group 0.000 description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 11
- 239000000376 reactant Substances 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 229910004856 P—O—P Inorganic materials 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 8
- 125000001246 bromo group Chemical group Br* 0.000 description 7
- 125000004185 ester group Chemical group 0.000 description 7
- 150000002500 ions Chemical class 0.000 description 7
- 235000021317 phosphate Nutrition 0.000 description 7
- 150000004713 phosphodiesters Chemical group 0.000 description 7
- 230000001476 alcoholic effect Effects 0.000 description 6
- 229910021529 ammonia Inorganic materials 0.000 description 6
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 150000002924 oxiranes Chemical class 0.000 description 6
- 229940005657 pyrophosphoric acid Drugs 0.000 description 6
- 239000000523 sample Substances 0.000 description 6
- 238000005063 solubilization Methods 0.000 description 6
- 230000007928 solubilization Effects 0.000 description 6
- 241000894007 species Species 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 5
- IGFHQQFPSIBGKE-UHFFFAOYSA-N 4-nonylphenol Chemical compound CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 5
- 229940106691 bisphenol a Drugs 0.000 description 5
- XPPKVPWEQAFLFU-UHFFFAOYSA-N diphosphoric acid Chemical compound OP(O)(=O)OP(O)(O)=O XPPKVPWEQAFLFU-UHFFFAOYSA-N 0.000 description 5
- 230000032050 esterification Effects 0.000 description 5
- 238000005886 esterification reaction Methods 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 230000002829 reductive effect Effects 0.000 description 5
- 238000004448 titration Methods 0.000 description 5
- 239000003039 volatile agent Substances 0.000 description 5
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 4
- 230000009471 action Effects 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- 230000003247 decreasing effect Effects 0.000 description 4
- 230000003472 neutralizing effect Effects 0.000 description 4
- 125000001400 nonyl 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])([H])[H] 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical class [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 238000006735 epoxidation reaction Methods 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
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- 230000035484 reaction time Effects 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- MDLKWDQMIZRIBY-UHFFFAOYSA-N 1-(dimethylamino)ethanol Chemical compound CC(O)N(C)C MDLKWDQMIZRIBY-UHFFFAOYSA-N 0.000 description 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
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- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 2
- 241000282337 Nasua nasua Species 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
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- 229910000831 Steel Inorganic materials 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000011149 active material Substances 0.000 description 2
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- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 159000000007 calcium salts Chemical group 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
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- 239000010960 cold rolled steel Substances 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
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- 230000001419 dependent effect Effects 0.000 description 2
- 230000001627 detrimental effect Effects 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 238000007865 diluting Methods 0.000 description 2
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- 238000000605 extraction Methods 0.000 description 2
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- 239000007970 homogeneous dispersion Substances 0.000 description 2
- 125000001145 hydrido group Chemical group *[H] 0.000 description 2
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- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 2
- 239000005029 tin-free steel Substances 0.000 description 2
- 238000000954 titration curve Methods 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- UNXRWKVEANCORM-UHFFFAOYSA-N triphosphoric acid Chemical compound OP(O)(=O)OP(O)(=O)OP(O)(O)=O UNXRWKVEANCORM-UHFFFAOYSA-N 0.000 description 2
- 229940048102 triphosphoric acid Drugs 0.000 description 2
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- CDOSHBSSFJOMGT-JTQLQIEISA-N (R)-linalool Natural products CC(C)=CCC[C@@](C)(O)C=C CDOSHBSSFJOMGT-JTQLQIEISA-N 0.000 description 1
- ORTVZLZNOYNASJ-UPHRSURJSA-N (z)-but-2-ene-1,4-diol Chemical compound OC\C=C/CO ORTVZLZNOYNASJ-UPHRSURJSA-N 0.000 description 1
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical class NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- JACNQGOTIIEIOA-UHFFFAOYSA-N 1,3-dioxane-2,2-diol Chemical compound OC1(O)OCCCO1 JACNQGOTIIEIOA-UHFFFAOYSA-N 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N 1-butanol Substances CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- XOUAQPDUNFWPEM-UHFFFAOYSA-N 2,3,4-tris(hydroxymethyl)phenol Chemical compound OCC1=CC=C(O)C(CO)=C1CO XOUAQPDUNFWPEM-UHFFFAOYSA-N 0.000 description 1
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- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical group [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
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- 150000007529 inorganic bases Chemical class 0.000 description 1
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
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- 230000003340 mental effect Effects 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
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- 150000005691 triesters Chemical class 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
-
- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/4007—Curing agents not provided for by the groups C08G59/42 - C08G59/66
- C08G59/4071—Curing agents not provided for by the groups C08G59/42 - C08G59/66 phosphorus containing compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Epoxy Resins (AREA)
- Paints Or Removers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US75376576A | 1976-12-23 | 1976-12-23 | |
| US75376376A | 1976-12-23 | 1976-12-23 | |
| US753,765 | 1976-12-23 | ||
| US753,763 | 1976-12-23 | ||
| US85316877A | 1977-11-21 | 1977-11-21 | |
| US853,167 | 1977-11-21 | ||
| US853,168 | 1977-11-21 | ||
| US05/853,167 US4164487A (en) | 1976-12-23 | 1977-11-21 | Water-thinnable mixtures of base-neutralized products of reaction of H3 PO4 with polyether epoxides and with other type epoxides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1113643A true CA1113643A (en) | 1981-12-01 |
Family
ID=27505664
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA293,737A Expired CA1113643A (en) | 1976-12-23 | 1977-12-22 | Method of water-solubilizing high performance polyether epoxide resins, the solubilized resins and thermoset, hydrophobic coatings derived therefrom |
Country Status (6)
| Country | Link |
|---|---|
| JP (2) | JPS53104699A (enrdf_load_stackoverflow) |
| CA (1) | CA1113643A (enrdf_load_stackoverflow) |
| DE (1) | DE2757733C2 (enrdf_load_stackoverflow) |
| FR (1) | FR2378822A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1597610A (enrdf_load_stackoverflow) |
| NL (1) | NL186517C (enrdf_load_stackoverflow) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT356905B (de) * | 1978-10-31 | 1980-06-10 | Vianova Kunstharz Ag | Verfahren zur herstellung von wasserloeslichen lackbindemitteln |
| US4508765A (en) * | 1981-10-20 | 1985-04-02 | International Paint Public Limited Company | Synthetic resins and coating compositions containing them |
| JPS58191764A (ja) * | 1982-05-04 | 1983-11-09 | Dainippon Toryo Co Ltd | 水系被覆用組成物 |
| US4425451A (en) * | 1982-09-29 | 1984-01-10 | Desoto, Inc. | Epoxy-phosphate aqueous dispersions |
| US4560732A (en) * | 1983-11-11 | 1985-12-24 | Asahi Denka Kogyo K.K. | Coating composition |
| EP0240876A3 (en) * | 1986-04-03 | 1988-08-31 | DeSoto, Inc. | Thermosetting aqueous anionic electrocoating composition containing epoxy phosphates |
| US4737529A (en) * | 1986-04-03 | 1988-04-12 | Desoto, Inc. | Cathodic electrocoat compositions containing epoxy phosphates |
| JPH03115149U (enrdf_load_stackoverflow) * | 1990-03-05 | 1991-11-27 | ||
| JPH04268319A (ja) * | 1991-02-22 | 1992-09-24 | Dow Chem Nippon Kk | 水分散可能なエポキシ樹脂及びその製造方法 |
| DE4427456A1 (de) * | 1994-08-03 | 1996-02-08 | Siemens Ag | Phosphormodifizierte Epoxidharze, Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE19608613C2 (de) * | 1996-03-06 | 2002-01-17 | Celanese Ventures Gmbh | Lagerstabile, phosphormodifizierte Epoxidharze |
| DE19608611A1 (de) * | 1996-03-06 | 1997-09-11 | Hoechst Ag | Phosphormodifizierte Überzugsmassen, ein Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE19608612C2 (de) * | 1996-03-06 | 1998-12-24 | Clariant Gmbh | Phosphormodifizierte Überzugsmassen, ein Verfahren zu ihrer Herstellung und ihre Verwendung als Intumeszenzbeschichtungen |
| DE19613061C2 (de) * | 1996-04-01 | 1998-07-02 | Clariant Gmbh | Phosphormodifizierte Epoxidharze aus Epoxidharzen und phosphorhaltigen Verbindungen |
| DE19613066C2 (de) * | 1996-04-01 | 1998-09-10 | Clariant Gmbh | Verfahren zur Herstellung phosphormodifizierter Epoxidharze |
| DE19613064C2 (de) * | 1996-04-01 | 1998-12-17 | Clariant Gmbh | Phosphormodifizierte Epoxidharzmischungen aus Epoxidharzen, phosphorhaltigen Verbindungen und einem Härter, Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE19613063C2 (de) * | 1996-04-01 | 1998-09-17 | Clariant Gmbh | Phosphormodifizierte Epoxidharze und ein Verfahren zu ihrer Herstellung |
| EP0799846B1 (de) * | 1996-04-01 | 2000-06-14 | Clariant GmbH | Phosphormodifizierte Epoxid-harzmischungen aus Expoxid-harzen, phosphorhaltigen Verbindungen und einem Härter |
| DE19960693A1 (de) * | 1999-12-16 | 2001-07-19 | Dupont Performance Coatings | Verfahren zur anodischen Elektrotauchlackierung, sowie Elektrotauchlacke |
| DE10120989A1 (de) | 2001-04-25 | 2002-11-07 | Inst Polymerforschung Dresden | Hydrophobe permanente Beschichtungen auf Substraten und Verfahren zu ihrer Herstellung |
| DE102004039758A1 (de) | 2004-08-17 | 2006-03-02 | Clariant Gmbh | Brandschutzbeschichtung |
| RU2543878C2 (ru) | 2009-03-05 | 2015-03-10 | Акцо Нобель Коатингс Интернэшнл Б.В. | Гидроксилфункциональные полиолы на основе масла и композиции для нанесения покрытия, полученные из гидроксилфункциональных полиолов на основе масла |
| CA2822750C (en) * | 2010-12-29 | 2019-11-12 | Akzo Nobel Coatings International B.V. | Adhesion promoter resin compositions and coating compositions having the adhesion promoter resin compositions |
| WO2013092541A1 (en) | 2011-12-21 | 2013-06-27 | Akzo Nobel Coatings International B.V. | Solvent-based coating compositions |
| BR112014014094B1 (pt) | 2011-12-21 | 2020-12-01 | Akzo Nobel Coatings International B.V. | composição de revestimento e substrato |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2541027A (en) * | 1948-05-11 | 1951-02-13 | Shell Dev | Compositions of matter containing epoxy ethers and phosphorus-containing compounds |
| BE498918A (enrdf_load_stackoverflow) * | 1949-10-25 | 1900-01-01 | ||
| US3018262A (en) * | 1957-05-01 | 1962-01-23 | Shell Oil Co | Curing polyepoxides with certain metal salts of inorganic acids |
| US4059550A (en) * | 1976-07-06 | 1977-11-22 | Celanese Polymer Specialties Company | Aqueous dispersions of polyhydroxy polyether resins and aminoplast resins |
| JPS61171774A (ja) * | 1976-12-23 | 1986-08-02 | ザ ダウ ケミカル カンパニ− | 水で希釈可能な樹脂状リン酸塩組成物およびそれから得られた被覆物 |
-
1977
- 1977-12-22 CA CA293,737A patent/CA1113643A/en not_active Expired
- 1977-12-23 FR FR7739153A patent/FR2378822A1/fr active Granted
- 1977-12-23 GB GB53850/77A patent/GB1597610A/en not_active Expired
- 1977-12-23 JP JP15457177A patent/JPS53104699A/ja active Granted
- 1977-12-23 DE DE2757733A patent/DE2757733C2/de not_active Expired
- 1977-12-23 NL NLAANVRAGE7714330,A patent/NL186517C/xx not_active IP Right Cessation
-
1988
- 1988-01-20 JP JP63010537A patent/JPS63270758A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DE2757733A1 (de) | 1978-07-13 |
| NL186517C (nl) | 1990-12-17 |
| GB1597610A (en) | 1981-09-09 |
| FR2378822A1 (fr) | 1978-08-25 |
| JPS623857B2 (enrdf_load_stackoverflow) | 1987-01-27 |
| DE2757733C2 (de) | 1987-01-22 |
| NL7714330A (nl) | 1978-06-27 |
| NL186517B (nl) | 1990-07-16 |
| JPH0345091B2 (enrdf_load_stackoverflow) | 1991-07-10 |
| JPS63270758A (ja) | 1988-11-08 |
| JPS53104699A (en) | 1978-09-12 |
| FR2378822B1 (enrdf_load_stackoverflow) | 1985-03-29 |
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