ES2449226T3 - Agente de curado de resinas epoxídicas para potenciar la resistencia al desgaste y resistencia a la intemperie de materiales curados - Google Patents
Agente de curado de resinas epoxídicas para potenciar la resistencia al desgaste y resistencia a la intemperie de materiales curados Download PDFInfo
- Publication number
- ES2449226T3 ES2449226T3 ES03759100.5T ES03759100T ES2449226T3 ES 2449226 T3 ES2449226 T3 ES 2449226T3 ES 03759100 T ES03759100 T ES 03759100T ES 2449226 T3 ES2449226 T3 ES 2449226T3
- Authority
- ES
- Spain
- Prior art keywords
- hardener
- compounds
- substituted
- condensation
- hardener according
- 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 - Lifetime
Links
- 239000003822 epoxy resin Substances 0.000 title claims abstract description 55
- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 55
- 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 claims abstract description 37
- 239000000463 material Substances 0.000 title claims abstract description 24
- 239000003795 chemical substances by application Substances 0.000 title description 17
- 239000004848 polyfunctional curative Substances 0.000 claims abstract description 90
- 150000001875 compounds Chemical class 0.000 claims abstract description 38
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 30
- 239000000047 product Substances 0.000 claims abstract description 28
- 150000001412 amines Chemical class 0.000 claims abstract description 26
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 20
- 239000007859 condensation product Substances 0.000 claims abstract description 19
- 238000009833 condensation Methods 0.000 claims abstract description 17
- 230000005494 condensation Effects 0.000 claims abstract description 17
- 230000007062 hydrolysis Effects 0.000 claims abstract description 16
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 16
- 239000000126 substance Substances 0.000 claims abstract description 16
- 238000005299 abrasion Methods 0.000 claims abstract description 15
- 239000002253 acid Substances 0.000 claims abstract description 15
- 125000003118 aryl group Chemical group 0.000 claims abstract description 15
- 229910052796 boron Inorganic materials 0.000 claims abstract description 15
- 150000002118 epoxides Chemical class 0.000 claims abstract description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 15
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 14
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims abstract description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 14
- 239000001257 hydrogen Substances 0.000 claims abstract description 14
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 14
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims abstract description 13
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims abstract description 13
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000010703 silicon Substances 0.000 claims abstract description 13
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 13
- 239000011593 sulfur Substances 0.000 claims abstract description 13
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 13
- 150000001298 alcohols Chemical class 0.000 claims abstract description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000001301 oxygen Substances 0.000 claims abstract description 12
- 150000007513 acids Chemical class 0.000 claims abstract description 11
- 150000002989 phenols Chemical class 0.000 claims abstract description 10
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims abstract description 8
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 7
- 239000011574 phosphorus Substances 0.000 claims abstract description 7
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 6
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 6
- 150000002367 halogens Chemical class 0.000 claims abstract description 6
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims abstract description 4
- 125000005328 phosphinyl group Chemical group [PH2](=O)* 0.000 claims abstract description 4
- 125000005499 phosphonyl group Chemical group 0.000 claims abstract description 4
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims abstract description 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims abstract description 4
- 125000004962 sulfoxyl group Chemical group 0.000 claims abstract description 4
- 125000002947 alkylene group Chemical group 0.000 claims abstract 3
- 125000000732 arylene group Chemical group 0.000 claims abstract 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract 3
- 238000000926 separation method Methods 0.000 claims abstract 3
- 239000007795 chemical reaction product Substances 0.000 claims description 28
- 239000002245 particle Substances 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 18
- 239000004593 Epoxy Substances 0.000 claims description 15
- 125000003277 amino group Chemical group 0.000 claims description 15
- 230000015572 biosynthetic process Effects 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 13
- -1 silane compound Chemical class 0.000 claims description 13
- 125000001931 aliphatic group Chemical group 0.000 claims description 12
- 125000006686 (C1-C24) alkyl group Chemical group 0.000 claims description 11
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 10
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 10
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 10
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 10
- 239000000654 additive Substances 0.000 claims description 9
- 229920005989 resin Polymers 0.000 claims description 9
- 239000011347 resin Substances 0.000 claims description 9
- 229910000077 silane Inorganic materials 0.000 claims description 9
- 125000004429 atom Chemical group 0.000 claims description 8
- 239000006096 absorbing agent Substances 0.000 claims description 5
- 239000012948 isocyanate Substances 0.000 claims description 5
- 150000002513 isocyanates Chemical class 0.000 claims description 5
- 239000003963 antioxidant agent Substances 0.000 claims description 4
- 239000000049 pigment Substances 0.000 claims description 4
- 239000002516 radical scavenger Substances 0.000 claims description 4
- 230000000996 additive effect Effects 0.000 claims description 3
- 150000007942 carboxylates Chemical class 0.000 claims description 3
- UOKZUTXLHRTLFH-UHFFFAOYSA-N o-phenylhydroxylamine Chemical compound NOC1=CC=CC=C1 UOKZUTXLHRTLFH-UHFFFAOYSA-N 0.000 claims description 3
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 claims description 3
- 230000003078 antioxidant effect Effects 0.000 claims description 2
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 claims description 2
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims description 2
- 229940123457 Free radical scavenger Drugs 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 59
- 238000006243 chemical reaction Methods 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 18
- 230000032683 aging Effects 0.000 description 15
- 238000004821 distillation Methods 0.000 description 13
- 239000002105 nanoparticle Substances 0.000 description 11
- 238000000576 coating method Methods 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- 239000003921 oil Substances 0.000 description 10
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 239000000499 gel Substances 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 9
- 238000003980 solgel method Methods 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 239000004033 plastic Substances 0.000 description 7
- 229920003023 plastic Polymers 0.000 description 7
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 229920001187 thermosetting polymer Polymers 0.000 description 6
- 238000012546 transfer Methods 0.000 description 6
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 238000004132 cross linking Methods 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 238000012986 modification Methods 0.000 description 5
- 230000004048 modification Effects 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- KFUSXMDYOPXKKT-UHFFFAOYSA-N 2-[(2-methylphenoxy)methyl]oxirane Chemical compound CC1=CC=CC=C1OCC1OC1 KFUSXMDYOPXKKT-UHFFFAOYSA-N 0.000 description 4
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 4
- KWXICGTUELOLSQ-UHFFFAOYSA-N 4-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=C(S(O)(=O)=O)C=C1 KWXICGTUELOLSQ-UHFFFAOYSA-N 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- 239000000945 filler Substances 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- 238000004383 yellowing Methods 0.000 description 4
- ZSSVCEUEVMALRD-UHFFFAOYSA-N 2-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-5-(octyloxy)phenol Chemical compound OC1=CC(OCCCCCCCC)=CC=C1C1=NC(C=2C(=CC(C)=CC=2)C)=NC(C=2C(=CC(C)=CC=2)C)=N1 ZSSVCEUEVMALRD-UHFFFAOYSA-N 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 150000004756 silanes Chemical class 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 229920003319 Araldite® Polymers 0.000 description 2
- 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 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical class SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000010954 inorganic particle Substances 0.000 description 2
- 239000004922 lacquer Substances 0.000 description 2
- 230000005588 protonation Effects 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- TXDNPSYEJHXKMK-UHFFFAOYSA-N sulfanylsilane Chemical class S[SiH3] TXDNPSYEJHXKMK-UHFFFAOYSA-N 0.000 description 2
- 239000004408 titanium dioxide Substances 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 1
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 1
- RREANTFLPGEWEN-MBLPBCRHSA-N 7-[4-[[(3z)-3-[4-amino-5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidin-2-yl]imino-5-fluoro-2-oxoindol-1-yl]methyl]piperazin-1-yl]-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(\N=C/3C4=CC(F)=CC=C4N(CN4CCN(CC4)C=4C(=CC=5C(=O)C(C(O)=O)=CN(C=5C=4)C4CC4)F)C\3=O)=NC=2)N)=C1 RREANTFLPGEWEN-MBLPBCRHSA-N 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229910002012 Aerosil® Inorganic materials 0.000 description 1
- 229920001342 Bakelite® Polymers 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 239000002033 PVDF binder Substances 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 238000006136 alcoholysis reaction Methods 0.000 description 1
- 238000007098 aminolysis reaction Methods 0.000 description 1
- 238000000149 argon plasma sintering Methods 0.000 description 1
- 239000004637 bakelite Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000002144 chemical decomposition reaction Methods 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000004053 dental implant Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- NZYMWGXNIUZYRC-UHFFFAOYSA-N hexadecyl 3,5-ditert-butyl-4-hydroxybenzoate Chemical compound CCCCCCCCCCCCCCCCOC(=O)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NZYMWGXNIUZYRC-UHFFFAOYSA-N 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 150000004658 ketimines Chemical class 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 239000002114 nanocomposite Substances 0.000 description 1
- 239000002159 nanocrystal Substances 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 238000010525 oxidative degradation reaction Methods 0.000 description 1
- 125000000394 phosphonato group Chemical group [O-]P([O-])(*)=O 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002620 polyvinyl fluoride Polymers 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- 238000012797 qualification Methods 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 238000006748 scratching Methods 0.000 description 1
- 230000002393 scratching effect Effects 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003452 sulfinic acid derivatives Chemical class 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003458 sulfonic acid derivatives Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 1
Classifications
-
- 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
- C08G59/4085—Curing agents not provided for by the groups C08G59/42 - C08G59/66 silicon containing compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Epoxy Resins (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Paints Or Removers (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NO20024990A NO322911B1 (no) | 2002-10-16 | 2002-10-16 | Herder for herding av epoksyharpikser samt gjenstand fremstilt av epoksiharpiks og slik herder |
| NO20024990 | 2002-10-16 | ||
| PCT/NO2003/000342 WO2004035675A1 (en) | 2002-10-16 | 2003-10-16 | Epoxy resin curing agent for enhanced wear resistance and weatherability of cured materials |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2449226T3 true ES2449226T3 (es) | 2014-03-18 |
Family
ID=19914096
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES03759100.5T Expired - Lifetime ES2449226T3 (es) | 2002-10-16 | 2003-10-16 | Agente de curado de resinas epoxídicas para potenciar la resistencia al desgaste y resistencia a la intemperie de materiales curados |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US8450451B2 (enExample) |
| EP (1) | EP1556438B1 (enExample) |
| JP (1) | JP4883908B2 (enExample) |
| CN (1) | CN1329438C (enExample) |
| AU (1) | AU2003274839A1 (enExample) |
| CA (1) | CA2502536C (enExample) |
| DK (1) | DK1556438T3 (enExample) |
| ES (1) | ES2449226T3 (enExample) |
| NO (1) | NO322911B1 (enExample) |
| PT (1) | PT1556438E (enExample) |
| WO (1) | WO2004035675A1 (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102005014958A1 (de) * | 2005-03-30 | 2006-10-05 | Sensient Imaging Technologies Gmbh | Deckschicht für eletrophotografische Druckwalzen |
| NO325797B1 (no) * | 2005-10-14 | 2008-07-21 | Nor X Ind As | Lysbeskyttelsesmiddel basert på organisk/uorganisk hybridpolymer, fremgangsmåte til fremstilling og anvendelse av samme |
| IL180474A (en) * | 2007-01-01 | 2013-12-31 | Curapipe Ltd | A process and structure for blocking "in place" of pipeline leaks |
| EP2132695A4 (en) * | 2007-02-26 | 2011-04-13 | Hello Hello Inc | COMPARATIVE MASS ANALYSIS OF ADVERTISING |
| CN101527839B (zh) * | 2008-03-06 | 2011-05-11 | 中兴通讯股份有限公司 | 一种提高无线多媒体带宽使用效率的方法 |
| CN101696263B (zh) * | 2009-10-29 | 2012-12-05 | 复旦大学 | 一种环氧树脂固化剂及其制备方法和应用 |
| RU2462467C1 (ru) * | 2011-09-26 | 2012-09-27 | Общество с ограниченной ответственностью "Пента-91" | Способ получения отвердителя низкомолекулярных эпоксидных смол |
| CN104378907B (zh) * | 2013-08-12 | 2017-06-30 | 富葵精密组件(深圳)有限公司 | 电路板及其制作方法 |
| US20180023244A1 (en) | 2016-07-19 | 2018-01-25 | Hexcel Corporation | Composite carbon fibers |
| US10894868B2 (en) | 2017-12-21 | 2021-01-19 | Hexcel Corporation | Composite carbon fibers |
Family Cites Families (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6021628B2 (ja) * | 1977-09-08 | 1985-05-28 | 東レ株式会社 | 高硬度塗膜を有するプラスチツクの製造方法 |
| US4250074A (en) * | 1979-09-06 | 1981-02-10 | Ameron, Inc. | Interpenetrating polymer network comprising epoxy polymer and polysiloxane |
| JPH077123B2 (ja) * | 1985-03-22 | 1995-01-30 | 東レ株式会社 | 透明成形体 |
| DE3813719A1 (de) * | 1988-04-22 | 1989-11-02 | Wacker Chemie Gmbh | Verfahren zur herstellung von waermebestaendigen, vernetzten epoxyharzen |
| JPH01272623A (ja) * | 1988-04-25 | 1989-10-31 | Matsushita Electric Works Ltd | エポキシ樹脂組成物 |
| JPH01304111A (ja) * | 1988-06-01 | 1989-12-07 | Chisso Corp | 常温硬化性樹脂組成物 |
| NO166189C (no) * | 1989-02-08 | 1991-06-12 | Norsk Hydro As | Tverrbundet termostabil polymer og fremstilling derav. |
| US4988778A (en) * | 1990-01-18 | 1991-01-29 | Ppg Industries, Inc. | Polyamine-functional silane resin |
| US5786032A (en) * | 1991-11-22 | 1998-07-28 | Vision-Ease Lens, Inc. | Coating composition and process for producing coated articles |
| JP2812120B2 (ja) * | 1992-03-30 | 1998-10-22 | 株式会社日本触媒 | 表面処理用組成物および表面処理樹脂成形体 |
| JP3410495B2 (ja) * | 1992-09-30 | 2003-05-26 | 東レ・ダウコーニング・シリコーン株式会社 | 表面塗布剤 |
| US6534187B2 (en) * | 1993-02-08 | 2003-03-18 | Fraunhofer-Gesellschaft Zur Foerderung Der Angewandten Forschung E.V. | Coating material and process for the production of functional coatings |
| JP2739902B2 (ja) * | 1993-09-30 | 1998-04-15 | 東京応化工業株式会社 | 酸化ケイ素系被膜形成用塗布液 |
| JP2695113B2 (ja) * | 1993-12-21 | 1997-12-24 | 松下電工株式会社 | ケイ素系コーティング層を有する無機質硬化体又は金属表面の補修方法 |
| DE19501093C2 (de) * | 1995-01-16 | 1997-01-16 | Fraunhofer Ges Forschung | Verwendung eines hydrolytischen Kondensationsproduktes eines organo-funktionellen Silans zur Behandlung von in Glasgegenständen vorhandenen aufgerauhten Flächen |
| CA2175609C (en) * | 1995-05-12 | 2004-06-22 | Hata, Nobuhiko | Fuel tank |
| JPH10120972A (ja) * | 1996-10-17 | 1998-05-12 | Toray Ind Inc | 熱硬化性樹脂組成物 |
| EP1101072A1 (en) * | 1998-07-28 | 2001-05-23 | Arcelik A.S. | A method for preventing water accumulation and ice formation on the evaporators and condensers of refrigerators |
| DE19957324B4 (de) * | 1999-11-29 | 2011-12-01 | Few Chemicals Gmbh | Beschichtungszusammensetzung und deren Verwendung zur Herstellung von Schutzschichten für Polymere, damit hergestellteSchutzschichten sowie Verfahren zu deren Herstellung |
| NO319405B1 (no) * | 2000-07-05 | 2005-08-08 | Sintef | Organisk basert lakk eller gel-coat, fremgangsmate til fremstilling samt anvendelse av samme |
| DE10117338A1 (de) * | 2001-04-06 | 2002-10-10 | Few Chemicals Gmbh | Beschichtungszusammensetzung zur Herstellung einer Permeationsschutzschicht |
| NO322777B1 (no) * | 2004-04-15 | 2006-12-11 | Sinvent As | Polyforgrenet organisk/uorganisk hybridpolymer, fremgangsmåte til dens fremstilling samt anvendelse av samme |
| NO322724B1 (no) * | 2004-04-15 | 2006-12-04 | Sinvent As | Fremgangsmåte til fremstilling av polyforgrenet organisk/uorganisk hybridpolymer |
| NO325853B1 (no) * | 2004-04-16 | 2008-08-04 | Nor X Ind As | Polymer kommpound |
-
2002
- 2002-10-16 NO NO20024990A patent/NO322911B1/no not_active IP Right Cessation
-
2003
- 2003-10-16 PT PT37591005T patent/PT1556438E/pt unknown
- 2003-10-16 CA CA2502536A patent/CA2502536C/en not_active Expired - Fee Related
- 2003-10-16 JP JP2004545090A patent/JP4883908B2/ja not_active Expired - Fee Related
- 2003-10-16 EP EP03759100.5A patent/EP1556438B1/en not_active Expired - Lifetime
- 2003-10-16 ES ES03759100.5T patent/ES2449226T3/es not_active Expired - Lifetime
- 2003-10-16 CN CNB2003801040769A patent/CN1329438C/zh not_active Expired - Fee Related
- 2003-10-16 DK DK03759100.5T patent/DK1556438T3/en active
- 2003-10-16 AU AU2003274839A patent/AU2003274839A1/en not_active Abandoned
- 2003-10-16 US US10/531,473 patent/US8450451B2/en not_active Expired - Fee Related
- 2003-10-16 WO PCT/NO2003/000342 patent/WO2004035675A1/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| CA2502536A1 (en) | 2004-04-29 |
| NO322911B1 (no) | 2006-12-18 |
| CN1717444A (zh) | 2006-01-04 |
| EP1556438B1 (en) | 2013-11-27 |
| US20050288395A1 (en) | 2005-12-29 |
| NO20024990D0 (no) | 2002-10-16 |
| EP1556438A1 (en) | 2005-07-27 |
| DK1556438T3 (en) | 2014-03-03 |
| JP2006503155A (ja) | 2006-01-26 |
| JP4883908B2 (ja) | 2012-02-22 |
| AU2003274839A1 (en) | 2004-05-04 |
| PT1556438E (pt) | 2014-02-27 |
| CN1329438C (zh) | 2007-08-01 |
| NO20024990L (no) | 2004-04-19 |
| US8450451B2 (en) | 2013-05-28 |
| CA2502536C (en) | 2011-01-04 |
| WO2004035675A1 (en) | 2004-04-29 |
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