CA1093237A - Filled resinous thermosettable liquids containing titanate salts - Google Patents
Filled resinous thermosettable liquids containing titanate saltsInfo
- Publication number
- CA1093237A CA1093237A CA267,949A CA267949A CA1093237A CA 1093237 A CA1093237 A CA 1093237A CA 267949 A CA267949 A CA 267949A CA 1093237 A CA1093237 A CA 1093237A
- Authority
- CA
- Canada
- Prior art keywords
- titanate
- composition
- group
- filler
- resin
- 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
- 239000007788 liquid Substances 0.000 title claims abstract description 18
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical class [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 title claims description 69
- -1 diester pyrophosphate Chemical class 0.000 claims abstract description 103
- 239000000203 mixture Substances 0.000 claims abstract description 65
- 239000000945 filler Substances 0.000 claims abstract description 44
- 125000003118 aryl group Chemical group 0.000 claims abstract description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 21
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 19
- 239000003822 epoxy resin Substances 0.000 claims abstract description 18
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 18
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 11
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 229910019142 PO4 Inorganic materials 0.000 claims abstract description 7
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims abstract description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 5
- 239000010452 phosphate Substances 0.000 claims abstract description 5
- 239000011342 resin composition Substances 0.000 claims abstract description 5
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims abstract description 5
- 125000005296 thioaryloxy group Chemical group 0.000 claims abstract description 5
- 235000011180 diphosphates Nutrition 0.000 claims abstract description 4
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 23
- 239000004593 Epoxy Substances 0.000 claims description 19
- 229920000642 polymer Polymers 0.000 claims description 18
- 239000003973 paint Substances 0.000 claims description 16
- 239000000049 pigment Substances 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
- 229920001568 phenolic resin Polymers 0.000 claims description 9
- 239000005011 phenolic resin Substances 0.000 claims description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
- 150000003568 thioethers Chemical class 0.000 claims description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 239000004576 sand Substances 0.000 claims description 8
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 claims description 7
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 239000000178 monomer Substances 0.000 claims description 7
- 229920001187 thermosetting polymer Polymers 0.000 claims description 7
- 125000003700 epoxy group Chemical group 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 239000007849 furan resin Substances 0.000 claims description 6
- 239000004925 Acrylic resin Substances 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- IBAHLNWTOIHLKE-UHFFFAOYSA-N cyano cyanate Chemical compound N#COC#N IBAHLNWTOIHLKE-UHFFFAOYSA-N 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000004036 acetal group Chemical group 0.000 claims description 2
- 239000010438 granite Substances 0.000 claims description 2
- 239000002243 precursor Substances 0.000 claims description 2
- 229920005989 resin Polymers 0.000 abstract description 28
- 239000011347 resin Substances 0.000 abstract description 28
- 238000002360 preparation method Methods 0.000 abstract description 7
- 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 abstract description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 4
- 125000002947 alkylene group Chemical group 0.000 abstract description 2
- 150000003839 salts Chemical class 0.000 abstract 1
- 238000009472 formulation Methods 0.000 description 22
- 239000010936 titanium Substances 0.000 description 16
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- 235000013350 formula milk Nutrition 0.000 description 10
- 239000000463 material Substances 0.000 description 10
- 238000002156 mixing Methods 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- 239000006185 dispersion Substances 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 8
- 239000012141 concentrate Substances 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- 238000011068 loading method Methods 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 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 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 239000002609 medium Substances 0.000 description 5
- 125000001624 naphthyl group Chemical group 0.000 description 5
- 235000021317 phosphate Nutrition 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- HYBBIBNJHNGZAN-UHFFFAOYSA-N Furaldehyde Natural products O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 4
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 4
- 229910052742 iron Inorganic materials 0.000 description 4
- 229910002055 micronized silica Inorganic materials 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 229960005419 nitrogen Drugs 0.000 description 4
- 150000003608 titanium Chemical class 0.000 description 4
- 229910052719 titanium Inorganic materials 0.000 description 4
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- IEKHISJGRIEHRE-UHFFFAOYSA-N 16-methylheptadecanoic acid;propan-2-ol;titanium Chemical compound [Ti].CC(C)O.CC(C)CCCCCCCCCCCCCCC(O)=O.CC(C)CCCCCCCCCCCCCCC(O)=O.CC(C)CCCCCCCCCCCCCCC(O)=O IEKHISJGRIEHRE-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 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
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 238000005266 casting Methods 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 125000003438 dodecyl group Chemical group [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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 229910003480 inorganic solid Inorganic materials 0.000 description 3
- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 3
- 239000000391 magnesium silicate Substances 0.000 description 3
- 229910052919 magnesium silicate Inorganic materials 0.000 description 3
- 235000019792 magnesium silicate Nutrition 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 3
- 239000004848 polyfunctional curative Substances 0.000 description 3
- 229940048084 pyrophosphate Drugs 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- ZQLIFZLPMQFLIY-UHFFFAOYSA-N 2-(dimethylamino)pentan-1-ol Chemical compound CCCC(CO)N(C)C ZQLIFZLPMQFLIY-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- NDSXSCFKIAPKJG-UHFFFAOYSA-N CC(C)O[Ti] Chemical compound CC(C)O[Ti] NDSXSCFKIAPKJG-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
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 239000004606 Fillers/Extenders Substances 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 239000005864 Sulphur Substances 0.000 description 2
- 229910010066 TiC14 Inorganic materials 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 229920000180 alkyd Polymers 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000013522 chelant Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000004927 clay Substances 0.000 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 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 230000005484 gravity Effects 0.000 description 2
- 239000004312 hexamethylene tetramine Substances 0.000 description 2
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000011256 inorganic filler Substances 0.000 description 2
- 229910003475 inorganic filler Inorganic materials 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 239000011147 inorganic material Substances 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 229960004011 methenamine Drugs 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 229920000058 polyacrylate Polymers 0.000 description 2
- 235000013824 polyphenols Nutrition 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000010453 quartz Substances 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 229910000077 silane Inorganic materials 0.000 description 2
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 2
- 229910010271 silicon carbide Inorganic materials 0.000 description 2
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 229960005349 sulfur Drugs 0.000 description 2
- 235000001508 sulfur Nutrition 0.000 description 2
- 239000004634 thermosetting polymer Substances 0.000 description 2
- 239000004408 titanium dioxide Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 239000003039 volatile agent Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- MBYQPPXEXWRMQC-UHFFFAOYSA-N (2-chlorophenyl)methanol Chemical compound OCC1=CC=CC=C1Cl MBYQPPXEXWRMQC-UHFFFAOYSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- WIEXMPDBTYDSQF-UHFFFAOYSA-N 1,3-bis(furan-2-yl)propan-2-one Chemical compound C=1C=COC=1CC(=O)CC1=CC=CO1 WIEXMPDBTYDSQF-UHFFFAOYSA-N 0.000 description 1
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- JOLVYUIAMRUBRK-UHFFFAOYSA-N 11',12',14',15'-Tetradehydro(Z,Z-)-3-(8-Pentadecenyl)phenol Natural products OC1=CC=CC(CCCCCCCC=CCC=CCC=C)=C1 JOLVYUIAMRUBRK-UHFFFAOYSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- RMBFBMJGBANMMK-UHFFFAOYSA-N 2,4-dinitrotoluene Chemical compound CC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O RMBFBMJGBANMMK-UHFFFAOYSA-N 0.000 description 1
- YGYNBBAUIYTWBF-UHFFFAOYSA-N 2,6-dimethyl naphthalene Natural products C1=C(C)C=CC2=CC(C)=CC=C21 YGYNBBAUIYTWBF-UHFFFAOYSA-N 0.000 description 1
- CJWNFAKWHDOUKL-UHFFFAOYSA-N 2-(2-phenylpropan-2-yl)phenol Chemical compound C=1C=CC=C(O)C=1C(C)(C)C1=CC=CC=C1 CJWNFAKWHDOUKL-UHFFFAOYSA-N 0.000 description 1
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical class CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 1
- 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 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- YLKVIMNNMLKUGJ-UHFFFAOYSA-N 3-Delta8-pentadecenylphenol Natural products CCCCCCC=CCCCCCCCC1=CC=CC(O)=C1 YLKVIMNNMLKUGJ-UHFFFAOYSA-N 0.000 description 1
- ZAJAQTYSTDTMCU-UHFFFAOYSA-N 3-aminobenzenesulfonic acid Chemical class NC1=CC=CC(S(O)(=O)=O)=C1 ZAJAQTYSTDTMCU-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- UQRONKZLYKUEMO-UHFFFAOYSA-N 4-methyl-1-(2,4,6-trimethylphenyl)pent-4-en-2-one Chemical group CC(=C)CC(=O)Cc1c(C)cc(C)cc1C UQRONKZLYKUEMO-UHFFFAOYSA-N 0.000 description 1
- BWDBEAQIHAEVLV-UHFFFAOYSA-N 6-methylheptan-1-ol Chemical compound CC(C)CCCCCO BWDBEAQIHAEVLV-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
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Classifications
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- 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
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/41—Organic pigments; Organic dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Paints Or Removers (AREA)
- Pigments, Carbon Blacks, Or Wood Stains (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US653,773 | 1976-01-30 | ||
| US05/653,773 US4069192A (en) | 1976-01-30 | 1976-01-30 | Liquid thermosetting resins containing titanate salts |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1093237A true CA1093237A (en) | 1981-01-06 |
Family
ID=24622246
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA267,949A Expired CA1093237A (en) | 1976-01-30 | 1976-12-15 | Filled resinous thermosettable liquids containing titanate salts |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4069192A (cg-RX-API-DMAC7.html) |
| JP (1) | JPS52104541A (cg-RX-API-DMAC7.html) |
| CA (1) | CA1093237A (cg-RX-API-DMAC7.html) |
| DE (1) | DE2703829C3 (cg-RX-API-DMAC7.html) |
| FR (1) | FR2339658A1 (cg-RX-API-DMAC7.html) |
| GB (2) | GB1576272A (cg-RX-API-DMAC7.html) |
Families Citing this family (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4261913A (en) * | 1976-01-30 | 1981-04-14 | Kenrich Petrochemicals, Inc. | Titanate phosphite adducts and their use |
| US4163004A (en) * | 1977-06-17 | 1979-07-31 | Wallace A. Erickson & Company | Dental filling materials |
| US4207226A (en) * | 1978-08-03 | 1980-06-10 | The Carborundum Company | Ceramic composition suited to be injection molded and sintered |
| US4260406A (en) * | 1978-08-17 | 1981-04-07 | Corning Glass Works | Gelled solder glass suspensions for sealing glass or ceramic parts |
| US4417009A (en) * | 1979-08-29 | 1983-11-22 | Kenrich Petrochemicals, Inc. | Pyrophosphato titanate adducts |
| US4269756A (en) * | 1979-12-27 | 1981-05-26 | Union Carbide Corporation | Use of organotitanate in the encapsulation of electrical components |
| US4328041A (en) * | 1980-06-09 | 1982-05-04 | Milliken Research Corporation | Comminuted inorganic materials |
| US4469637A (en) * | 1980-09-12 | 1984-09-04 | Trakka Corporation | Electro conductive polymer compositions and new materials found useful in their preparation |
| US4374760A (en) * | 1980-09-12 | 1983-02-22 | Harold Charles | Electro conductive polymer compositions and new materials found useful in their preparation |
| EP0055928A3 (en) * | 1980-12-30 | 1982-12-29 | Aerofoam Industries (Proprietary) Limited | Process for the production of polyurethane polymer compositions |
| JPS5924760A (ja) * | 1982-07-31 | 1984-02-08 | Pentel Kk | 二酸化チタンの着色法 |
| JPS5975931A (ja) * | 1982-10-23 | 1984-04-28 | Fukuda Kinzoku Hakufun Kogyo Kk | 合成樹脂充填用金属粉末 |
| US4560716A (en) * | 1983-08-30 | 1985-12-24 | Kabushiki Kaisha Toyota Chuo Kenkyusho | Rust preventing epoxy resin compositions |
| US4532074A (en) * | 1983-11-07 | 1985-07-30 | Rca Corporation | Capacitance electronic disc molding composition |
| US4600789A (en) * | 1984-05-14 | 1986-07-15 | Kenrich Petrochemicals, Inc. | Neoalkoxy organo-titanate useful as coupling and polymer processing agents |
| US4623738A (en) | 1985-04-22 | 1986-11-18 | Kenrich Petrochemicals, Inc. | Neoalkoxy organo-titanates and organo-zirconates useful as coupling and polymer processing agents |
| GB8418517D0 (en) * | 1984-07-20 | 1984-08-22 | Tioxide Group Plc | Titanium compositions |
| GB8418518D0 (en) * | 1984-07-20 | 1984-08-22 | Tioxide Group Plc | Compositions incorporating titanium compounds |
| US4634785A (en) * | 1984-09-14 | 1987-01-06 | Kenrich Petrochemicals, Inc. | Titanium and zirconium pyrophosphates, their preparation and use |
| US4792580A (en) * | 1985-09-04 | 1988-12-20 | The Sherwin-Williams Company | High solid coatings containing titanates and silanes |
| US4721747A (en) * | 1985-09-04 | 1988-01-26 | The Sherwin-Williams Company | High solid coatings containing titanates and silanes |
| JPH0665708B2 (ja) * | 1985-11-29 | 1994-08-24 | 鐘淵化学工業株式会社 | 新規ポリイミドフィルム及びその製造法 |
| WO1989009245A1 (fr) * | 1988-04-01 | 1989-10-05 | Nippon Soda Co., Ltd. | Agent de traitement de surfaces et poudre de charge traitee en surface avec ledit agent |
| GB8825864D0 (en) * | 1988-11-04 | 1988-12-07 | Tioxide Group Plc | Curable compositions |
| US4945000A (en) * | 1989-01-18 | 1990-07-31 | Btl Specialty Resins Corp. | Particulate thermosetting adhesive compositions |
| US5045575A (en) * | 1989-12-18 | 1991-09-03 | General Dynamics Corporation, Convair Division | Method of reducing voids in thermoset resin products |
| US5659058A (en) * | 1995-05-31 | 1997-08-19 | Kenrich Petrochemicals, Inc. | Thermally stable antistatic agents |
| GB2324063A (en) * | 1996-01-30 | 1998-10-14 | Kobe Steel Europ Ltd | Liquid composite moulding process |
| GB9601783D0 (en) * | 1996-01-30 | 1996-04-03 | Kobe Steel Europ Ltd | Liquid composite moulding process |
| US6040397A (en) * | 1997-11-28 | 2000-03-21 | Lockheed Martin Corporation | Extremely low viscosity matrix epoxy suffusion resin system |
| US6103784A (en) | 1998-08-27 | 2000-08-15 | Henkel Corporation | Corrosion resistant structural foam |
| US7300534B2 (en) * | 2002-01-15 | 2007-11-27 | Boston Scientific Scimed, Inc. | Bonds between metals and polymers for medical devices |
| US7390841B2 (en) * | 2005-01-24 | 2008-06-24 | Biotech Products, Llc | Compostable vinyl halide polymer compositions and composite sheets |
| US8487018B2 (en) | 2005-01-24 | 2013-07-16 | Biotech Products, Llc | Heavy metal-free and anaerobically compostable vinyl halide compositions, articles and landfill biodegradation |
| US7902271B2 (en) * | 2005-01-24 | 2011-03-08 | Biotech Products, Llc | Compostable vinyl halide polymer compositions, composites and landfill biodegradation |
| US7956101B2 (en) * | 2005-01-24 | 2011-06-07 | Biotech Products, Llc | Anaerobically compostable polymeric compositions, articles and landfill biodegradation |
| US20090253324A1 (en) * | 2008-04-07 | 2009-10-08 | Biotech Products, Llc | Compostable Olefin Polymer Compositions, Composites and Landfill Biodegradation |
| US7939582B2 (en) * | 2005-01-24 | 2011-05-10 | Biotech Products, Llc | Compostable vinyl acetate polymer compositions, composites and landfill biodegradation |
| DE102020120592A1 (de) | 2020-08-04 | 2022-02-10 | Endress+Hauser Flowtec Ag | Feldgerät der Automatisierungstechnik |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL125300C (cg-RX-API-DMAC7.html) * | 1961-04-14 | |||
| US3697475A (en) * | 1969-10-30 | 1972-10-10 | Freeport Sulphur Co | Inorganic-organo titanate polymeric film |
| US3697474A (en) * | 1969-10-30 | 1972-10-10 | Freeport Sulphur Co | Organo-clay-polymer compositions |
| JPS4939169A (cg-RX-API-DMAC7.html) * | 1972-08-23 | 1974-04-12 |
-
1976
- 1976-01-30 US US05/653,773 patent/US4069192A/en not_active Expired - Lifetime
- 1976-12-15 CA CA267,949A patent/CA1093237A/en not_active Expired
-
1977
- 1977-01-28 FR FR7702469A patent/FR2339658A1/fr active Granted
- 1977-01-31 DE DE2703829A patent/DE2703829C3/de not_active Expired
- 1977-01-31 GB GB6379/78A patent/GB1576272A/en not_active Expired
- 1977-01-31 GB GB3859/77A patent/GB1576271A/en not_active Expired
- 1977-01-31 JP JP961877A patent/JPS52104541A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| GB1576272A (en) | 1980-10-08 |
| FR2339658A1 (fr) | 1977-08-26 |
| GB1576271A (en) | 1980-10-08 |
| FR2339658B1 (cg-RX-API-DMAC7.html) | 1980-11-21 |
| DE2703829B2 (de) | 1980-04-03 |
| DE2703829C3 (de) | 1980-11-20 |
| JPS52104541A (en) | 1977-09-02 |
| DE2703829A1 (de) | 1977-08-04 |
| JPS5546660B2 (cg-RX-API-DMAC7.html) | 1980-11-25 |
| US4069192A (en) | 1978-01-17 |
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