CA1113196A - Phenolic resin-polyisocyanate binders - Google Patents
Phenolic resin-polyisocyanate bindersInfo
- Publication number
- CA1113196A CA1113196A CA322,606A CA322606A CA1113196A CA 1113196 A CA1113196 A CA 1113196A CA 322606 A CA322606 A CA 322606A CA 1113196 A CA1113196 A CA 1113196A
- Authority
- CA
- Canada
- Prior art keywords
- phenolic resin
- resin
- binder
- hydrogen
- tertiary amine
- 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
- 239000011230 binding agent Substances 0.000 title claims abstract description 110
- 239000005056 polyisocyanate Substances 0.000 title claims abstract description 77
- 229920001228 polyisocyanate Polymers 0.000 title claims abstract description 75
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 title claims abstract description 39
- 229920001568 phenolic resin Polymers 0.000 claims abstract description 68
- 239000005011 phenolic resin Substances 0.000 claims abstract description 68
- 239000000839 emulsion Substances 0.000 claims abstract description 59
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 claims abstract description 54
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 23
- 239000007788 liquid Substances 0.000 claims abstract description 23
- 150000003512 tertiary amines Chemical class 0.000 claims abstract description 16
- 229910021645 metal ion Inorganic materials 0.000 claims abstract description 6
- 239000000203 mixture Substances 0.000 claims description 69
- 229920005989 resin Polymers 0.000 claims description 49
- 239000011347 resin Substances 0.000 claims description 49
- 239000000463 material Substances 0.000 claims description 26
- 239000004215 Carbon black (E152) Substances 0.000 claims description 24
- -1 hydrocarbon radicals Chemical class 0.000 claims description 24
- 239000004576 sand Substances 0.000 claims description 24
- 229930195733 hydrocarbon Natural products 0.000 claims description 23
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 14
- 239000004848 polyfunctional curative Substances 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 8
- 238000002156 mixing Methods 0.000 claims description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
- 125000001743 benzylic group Chemical group 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 239000007859 condensation product Substances 0.000 claims description 4
- 239000000470 constituent Substances 0.000 claims description 4
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 4
- AQIIVEISJBBUCR-UHFFFAOYSA-N 4-(3-phenylpropyl)pyridine Chemical group C=1C=NC=CC=1CCCC1=CC=CC=C1 AQIIVEISJBBUCR-UHFFFAOYSA-N 0.000 claims description 3
- DAZXVJBJRMWXJP-UHFFFAOYSA-N n,n-dimethylethylamine Chemical group CCN(C)C DAZXVJBJRMWXJP-UHFFFAOYSA-N 0.000 claims description 3
- 150000003254 radicals Chemical class 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229940086542 triethylamine Drugs 0.000 claims description 2
- 239000000306 component Substances 0.000 claims 16
- 238000007493 shaping process Methods 0.000 claims 3
- 239000011261 inert gas Substances 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 abstract description 29
- 230000007613 environmental effect Effects 0.000 abstract description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
- 238000012360 testing method Methods 0.000 description 12
- 239000002904 solvent Substances 0.000 description 11
- 150000002430 hydrocarbons Chemical class 0.000 description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 9
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 9
- 125000003118 aryl group Chemical group 0.000 description 8
- 239000003995 emulsifying agent Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000012948 isocyanate Substances 0.000 description 7
- 150000002513 isocyanates Chemical class 0.000 description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 229920003987 resole Polymers 0.000 description 6
- 229920005862 polyol Polymers 0.000 description 5
- 150000003077 polyols Chemical class 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000003381 stabilizer Substances 0.000 description 5
- 208000005156 Dehydration Diseases 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
- 230000018044 dehydration Effects 0.000 description 4
- 238000006297 dehydration reaction Methods 0.000 description 4
- 229920003986 novolac Polymers 0.000 description 4
- 229910000077 silane Inorganic materials 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 3
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 210000000988 bone and bone Anatomy 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 3
- 239000007764 o/w emulsion Substances 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- XWKFPIODWVPXLX-UHFFFAOYSA-N 2,5-dimethylpyridine Chemical compound CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 2
- VXQBJTKSVGFQOL-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethyl acetate Chemical compound CCCCOCCOCCOC(C)=O VXQBJTKSVGFQOL-UHFFFAOYSA-N 0.000 description 2
- FPZWZCWUIYYYBU-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl acetate Chemical compound CCOCCOCCOC(C)=O FPZWZCWUIYYYBU-UHFFFAOYSA-N 0.000 description 2
- 244000215068 Acacia senegal Species 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 229920000084 Gum arabic Polymers 0.000 description 2
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 2
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 229930040373 Paraformaldehyde Natural products 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 239000000205 acacia gum Substances 0.000 description 2
- 235000010489 acacia gum Nutrition 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 229920000180 alkyd Polymers 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000002635 aromatic organic solvent Substances 0.000 description 2
- 239000003849 aromatic solvent Substances 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000001627 detrimental effect Effects 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- 125000005442 diisocyanate group Chemical group 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000001804 emulsifying effect Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 235000013312 flour Nutrition 0.000 description 2
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 229910000464 lead oxide Inorganic materials 0.000 description 2
- GIWKOZXJDKMGQC-UHFFFAOYSA-L lead(2+);naphthalene-2-carboxylate Chemical compound [Pb+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 GIWKOZXJDKMGQC-UHFFFAOYSA-L 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- YEXPOXQUZXUXJW-UHFFFAOYSA-N oxolead Chemical compound [Pb]=O YEXPOXQUZXUXJW-UHFFFAOYSA-N 0.000 description 2
- 229920002866 paraformaldehyde Polymers 0.000 description 2
- 239000003495 polar organic solvent Substances 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 1
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 1
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 description 1
- OMVSWZDEEGIJJI-UHFFFAOYSA-N 2,2,4-Trimethyl-1,3-pentadienol diisobutyrate Chemical compound CC(C)C(=O)OC(C(C)C)C(C)(C)COC(=O)C(C)C OMVSWZDEEGIJJI-UHFFFAOYSA-N 0.000 description 1
- OVOUKWFJRHALDD-UHFFFAOYSA-N 2-[2-(2-acetyloxyethoxy)ethoxy]ethyl acetate Chemical compound CC(=O)OCCOCCOCCOC(C)=O OVOUKWFJRHALDD-UHFFFAOYSA-N 0.000 description 1
- NQBXSWAWVZHKBZ-UHFFFAOYSA-N 2-butoxyethyl acetate Chemical compound CCCCOCCOC(C)=O NQBXSWAWVZHKBZ-UHFFFAOYSA-N 0.000 description 1
- CRWNQZTZTZWPOF-UHFFFAOYSA-N 2-methyl-4-phenylpyridine Chemical compound C1=NC(C)=CC(C=2C=CC=CC=2)=C1 CRWNQZTZTZWPOF-UHFFFAOYSA-N 0.000 description 1
- ZAISDHPZTZIFQF-UHFFFAOYSA-N 2h-1,4-thiazine Chemical compound C1SC=CN=C1 ZAISDHPZTZIFQF-UHFFFAOYSA-N 0.000 description 1
- PWRBCZZQRRPXAB-UHFFFAOYSA-N 3-chloropyridine Chemical compound ClC1=CC=CN=C1 PWRBCZZQRRPXAB-UHFFFAOYSA-N 0.000 description 1
- DBOLXXRVIFGDTI-UHFFFAOYSA-N 4-benzylpyridine Chemical compound C=1C=NC=CC=1CC1=CC=CC=C1 DBOLXXRVIFGDTI-UHFFFAOYSA-N 0.000 description 1
- VJXRKZJMGVSXPX-UHFFFAOYSA-N 4-ethylpyridine Chemical compound CCC1=CC=NC=C1 VJXRKZJMGVSXPX-UHFFFAOYSA-N 0.000 description 1
- JCLFHZLOKITRCE-UHFFFAOYSA-N 4-pentoxyphenol Chemical compound CCCCCOC1=CC=C(O)C=C1 JCLFHZLOKITRCE-UHFFFAOYSA-N 0.000 description 1
- YSHMQTRICHYLGF-UHFFFAOYSA-N 4-tert-butylpyridine Chemical compound CC(C)(C)C1=CC=NC=C1 YSHMQTRICHYLGF-UHFFFAOYSA-N 0.000 description 1
- ZMFWEWMHABZQNB-UHFFFAOYSA-N 6-acetyloxyhexyl acetate Chemical compound CC(=O)OCCCCCCOC(C)=O ZMFWEWMHABZQNB-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- UDSFAEKRVUSQDD-UHFFFAOYSA-N Dimethyl adipate Chemical compound COC(=O)CCCCC(=O)OC UDSFAEKRVUSQDD-UHFFFAOYSA-N 0.000 description 1
- MUXOBHXGJLMRAB-UHFFFAOYSA-N Dimethyl succinate Chemical compound COC(=O)CCC(=O)OC MUXOBHXGJLMRAB-UHFFFAOYSA-N 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- ZQISRDCJNBUVMM-YFKPBYRVSA-N L-histidinol Chemical compound OC[C@@H](N)CC1=CNC=N1 ZQISRDCJNBUVMM-YFKPBYRVSA-N 0.000 description 1
- 240000006240 Linum usitatissimum Species 0.000 description 1
- 235000004431 Linum usitatissimum Nutrition 0.000 description 1
- QORUGOXNWQUALA-UHFFFAOYSA-N N=C=O.N=C=O.N=C=O.C1=CC=C(C(C2=CC=CC=C2)C2=CC=CC=C2)C=C1 Chemical compound N=C=O.N=C=O.N=C=O.C1=CC=C(C(C2=CC=CC=C2)C2=CC=CC=C2)C=C1 QORUGOXNWQUALA-UHFFFAOYSA-N 0.000 description 1
- 238000003853 Pinholing Methods 0.000 description 1
- 229920000538 Poly[(phenyl isocyanate)-co-formaldehyde] Polymers 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- OHBRHBQMHLEELN-UHFFFAOYSA-N acetic acid;1-butoxybutane Chemical compound CC(O)=O.CCCCOCCCC OHBRHBQMHLEELN-UHFFFAOYSA-N 0.000 description 1
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- HIFVAOIJYDXIJG-UHFFFAOYSA-N benzylbenzene;isocyanic acid Chemical class N=C=O.N=C=O.C=1C=CC=CC=1CC1=CC=CC=C1 HIFVAOIJYDXIJG-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- QHIWVLPBUQWDMQ-UHFFFAOYSA-N butyl prop-2-enoate;methyl 2-methylprop-2-enoate;prop-2-enoic acid Chemical compound OC(=O)C=C.COC(=O)C(C)=C.CCCCOC(=O)C=C QHIWVLPBUQWDMQ-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- XTDYIOOONNVFMA-UHFFFAOYSA-N dimethyl pentanedioate Chemical compound COC(=O)CCCC(=O)OC XTDYIOOONNVFMA-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000003628 erosive effect Effects 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- 239000006193 liquid solution Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000005058 metal casting Methods 0.000 description 1
- 239000002923 metal particle Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000004005 microsphere Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 125000005498 phthalate group Chemical class 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 244000104985 savin Species 0.000 description 1
- 235000001520 savin Nutrition 0.000 description 1
- CMXPERZAMAQXSF-UHFFFAOYSA-M sodium;1,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonate;1,8-dihydroxyanthracene-9,10-dione Chemical compound [Na+].O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O.CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC CMXPERZAMAQXSF-UHFFFAOYSA-M 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- 125000001874 trioxidanyl group Chemical group [*]OOO[H] 0.000 description 1
- 230000003313 weakening effect Effects 0.000 description 1
- 239000004246 zinc acetate Substances 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/54—Polycondensates of aldehydes
- C08G18/542—Polycondensates of aldehydes with phenols
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B22—CASTING; POWDER METALLURGY
- B22C—FOUNDRY MOULDING
- B22C1/00—Compositions of refractory mould or core materials; Grain structures thereof; Chemical or physical features in the formation or manufacture of moulds
- B22C1/16—Compositions of refractory mould or core materials; Grain structures thereof; Chemical or physical features in the formation or manufacture of moulds characterised by the use of binding agents; Mixtures of binding agents
- B22C1/20—Compositions of refractory mould or core materials; Grain structures thereof; Chemical or physical features in the formation or manufacture of moulds characterised by the use of binding agents; Mixtures of binding agents of organic agents
- B22C1/22—Compositions of refractory mould or core materials; Grain structures thereof; Chemical or physical features in the formation or manufacture of moulds characterised by the use of binding agents; Mixtures of binding agents of organic agents of resins or rosins
- B22C1/2233—Compositions of refractory mould or core materials; Grain structures thereof; Chemical or physical features in the formation or manufacture of moulds characterised by the use of binding agents; Mixtures of binding agents of organic agents of resins or rosins obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- B22C1/2273—Polyurethanes; Polyisocyanates
-
- 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
- C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
- C08G8/04—Condensation polymers of aldehydes or ketones with phenols only of aldehydes
- C08G8/08—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ
- C08G8/10—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ with phenol
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Mechanical Engineering (AREA)
- Polyurethanes Or Polyureas (AREA)
- Mold Materials And Core Materials (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US888,715 | 1978-03-21 | ||
| US05/888,715 US4179427A (en) | 1978-03-21 | 1978-03-21 | Phenolic resin-polyisocyanate binders |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1113196A true CA1113196A (en) | 1981-11-24 |
Family
ID=25393738
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA322,606A Expired CA1113196A (en) | 1978-03-21 | 1979-02-28 | Phenolic resin-polyisocyanate binders |
Country Status (19)
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4179427A (en) * | 1978-03-21 | 1979-12-18 | Ashland Oil, Inc. | Phenolic resin-polyisocyanate binders |
| JPS5568153A (en) * | 1978-11-13 | 1980-05-22 | Hitachi Chem Co Ltd | Carbon dioxide curing mold binder |
| US4293480A (en) * | 1979-05-11 | 1981-10-06 | Ashland Oil, Inc. | Urethane binder compositions for no-bake and cold box foundry application utilizing isocyanato-urethane polymers |
| US4341668A (en) * | 1980-09-16 | 1982-07-27 | Ashland Oil, Inc. | Aqueous composition containing aldehyde condensate and use thereof |
| JPS5770118A (en) * | 1980-10-17 | 1982-04-30 | Asahi Organic Chem Ind Co Ltd | Phenol formaldehyde resin composition and its production |
| US4366266A (en) * | 1981-02-05 | 1982-12-28 | Valvoline Oil & Chemicals Ltd. | Binder compositions and process for making molded products therewith |
| US4366193A (en) * | 1981-04-10 | 1982-12-28 | Ashland Oil, Inc. | Catechol-based vapor permeation curable coating compositions |
| US4368222A (en) * | 1981-06-05 | 1983-01-11 | Ashland Oil, Inc. | Vapor permeation curable coatings for surface-porous substrates |
| DE3134810C2 (de) * | 1981-09-03 | 1986-07-31 | Klein, Schanzlin & Becker Ag, 6710 Frankenthal | Verfahren zur Herstellung von Gießereikernen |
| US4374181A (en) * | 1981-09-14 | 1983-02-15 | Ashland Oil, Inc. | Vapor permeation curable coatings for reaction injection molded parts |
| US4343924A (en) * | 1981-09-14 | 1982-08-10 | Ashland Oil, Inc. | Stabilized phenolic resins for use in vapor permeation curing |
| US4396647A (en) * | 1982-02-22 | 1983-08-02 | Ashland Oil, Inc. | Vapor permeation curable coating compositions containing 2,3',4-trihydroxydiphenyl |
| AT375953B (de) * | 1983-03-21 | 1984-09-25 | Vianova Kunstharz Ag | Verfahren zur herstellung von selbstvernetzenden, kathodisch abscheidbaren etl-bindemitteln auf basis modifizierter alkylphenol-formaldehyd -kondensationsprodukte |
| AT375954B (de) * | 1983-03-21 | 1984-09-25 | Vianova Kunstharz Ag | Verfahren zur herstellung von selbstvernetzenden, kathodisch abscheidbaren etl-bindemitteln auf basis modifizierter phenol-novolake |
| DE3332063A1 (de) * | 1983-09-06 | 1985-03-21 | Raschig Gmbh, 6700 Ludwigshafen | Verfahren zur herstellung von benzylaetherharzen als bindemittel fuer giessereisande nach dem cold-box-system |
| US4546124A (en) * | 1984-10-12 | 1985-10-08 | Acme Resin Corporation | Polyurethane binder compositions |
| US4724892A (en) * | 1985-07-19 | 1988-02-16 | Ashland Oil, Inc. | Mold assembly and fabrication thereof with a self-setting urethane adhesive paste system |
| US4692479A (en) * | 1985-07-19 | 1987-09-08 | Ashland Oil, Inc. | Self-setting urethane adhesive paste system |
| DE3544451C1 (de) * | 1985-12-16 | 1987-01-15 | Ashland Suedchemie Kernfest | Verfahren zum Erzeugen einer wasserdurchlaessigen Umhuellung auf koernigen,wasserloeslichen Stoffen und seine Anwendung |
| JPS62173050A (ja) * | 1986-01-24 | 1987-07-29 | Asahi Organic Chem Ind Co Ltd | 鋳型用粘結剤成分の貯蔵方法 |
| US4760101A (en) * | 1986-08-25 | 1988-07-26 | Ashland Oil, Inc. | Polyurethane-forming binder compositions containing certain carboxylic acids as bench life extenders |
| DE3841853A1 (de) * | 1988-12-13 | 1990-06-21 | Hoechst Ag | Photopolymerisierbares elastomeres gemisch und dieses enthaltendes aufzeichnungsmaterial fuer die herstellung von ozonresistenten flexodruckformen |
| EP0465919B1 (en) * | 1990-07-05 | 1998-09-09 | Kao Corporation | Process for producing a foundry mold |
| JP2504638B2 (ja) * | 1990-07-05 | 1996-06-05 | 花王株式会社 | 硬化性鋳型製造用添加剤及び鋳型の製造方法 |
| DE4120582A1 (de) * | 1991-06-21 | 1992-12-24 | Hoechst Ag | Bindemittelharze zur herstellung von faserverbunden |
| US5646199A (en) * | 1991-07-22 | 1997-07-08 | Kao Corporation | Composition for mold |
| DE4327292C2 (de) * | 1993-08-13 | 1996-04-25 | Ashland Suedchemie Kernfest | Bindemittel zur Herstellung von Gießereikernen und -formen und ihre Verwendung |
| US6133340A (en) * | 1996-03-25 | 2000-10-17 | Ashland Inc. | Sleeves, their preparation, and use |
| US8815976B2 (en) * | 2007-11-14 | 2014-08-26 | University Of Northern Iowa Research Foundation | Humic substances-based polymer system |
| FR2951158B1 (fr) | 2009-10-13 | 2012-04-27 | Alain Sublet | Element de construction compose d'un granulat agglomere avec une resine epoxy ou une resine polyurethane |
| MX369919B (es) * | 2012-06-08 | 2019-11-26 | Ask Chemicals Lp | Mezcla de fundicion "de endurecimiento en frio" con tiempo de trabajo extendido. |
| WO2017205698A1 (en) * | 2016-05-26 | 2017-11-30 | Georgia-Pacific Chemicals Llc | Binders containing an aldehyde-based resin and an isocyanate-based resin and methods for making composite lignocellulose products therefrom |
| US11780112B2 (en) | 2016-05-26 | 2023-10-10 | Bakelite Chemicals Llc | Binders containing an aldehyde-based resin and an isocyanate-based resin and methods for making composite lignocellulose products therefrom |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3485797A (en) | 1966-03-14 | 1969-12-23 | Ashland Oil Inc | Phenolic resins containing benzylic ether linkages and unsubstituted para positions |
| US3429848A (en) * | 1966-08-01 | 1969-02-25 | Ashland Oil Inc | Foundry binder composition comprising benzylic ether resin,polyisocyanate,and tertiary amine |
| GB1210240A (en) * | 1967-11-14 | 1970-10-28 | Borden Chemical Company U K Lt | Improvements in or relating to the production of foundry moulding mixtures |
| GB1269202A (en) * | 1968-02-14 | 1972-04-06 | Fordath Ltd | Improvements in the production of cores for use in the production of metal castings |
| GB1272972A (en) * | 1968-04-24 | 1972-05-03 | Ashland Oil Inc | Resin compositions |
| US3632844A (en) * | 1969-03-10 | 1972-01-04 | Ashland Oil Inc | Non-sticking sand mix for foundry cores |
| US3676392A (en) * | 1971-01-26 | 1972-07-11 | Ashland Oil Inc | Resin compositions |
| US3941743A (en) * | 1973-04-27 | 1976-03-02 | Ashland Oil, Inc. | Cast metal appearing metal filled resin compositions |
| DE2432153B2 (de) * | 1974-07-04 | 1979-08-02 | Hoechst Ag, 6000 Frankfurt | Verfahren zur Herstellung von wäßrigen Emulsionen |
| US3905934A (en) * | 1974-05-23 | 1975-09-16 | Ashland Oil Inc | Phenolic resin-polyisocyanate binder systems containing dialkyl phthalate solvents |
| US4051092A (en) * | 1975-11-13 | 1977-09-27 | International Minerals & Chemical Corporation | Foundry core composition of aggregate and a binder therefor |
| US4048103A (en) * | 1976-02-09 | 1977-09-13 | Minnesota Mining And Manufacturing Company | Composition based on phenolic resin, polyisocyanate, and petroleum oil |
| US4124554A (en) * | 1977-02-03 | 1978-11-07 | Union Carbide Corporation | Post-formed aqueous phenolic resin dispersions |
| US4179427A (en) * | 1978-03-21 | 1979-12-18 | Ashland Oil, Inc. | Phenolic resin-polyisocyanate binders |
-
1978
- 1978-03-21 US US05/888,715 patent/US4179427A/en not_active Expired - Lifetime
-
1979
- 1979-02-28 CA CA322,606A patent/CA1113196A/en not_active Expired
- 1979-03-05 PH PH22252A patent/PH14435A/en unknown
- 1979-03-19 AR AR275863A patent/AR226680A1/es active
- 1979-03-20 ES ES478805A patent/ES478805A1/es not_active Expired
- 1979-03-20 PT PT69376A patent/PT69376A/pt unknown
- 1979-03-20 JP JP3315579A patent/JPS54130698A/ja active Granted
- 1979-03-20 GB GB7909760A patent/GB2017126B/en not_active Expired
- 1979-03-20 AU AU45348/79A patent/AU511025B2/en not_active Ceased
- 1979-03-20 ZA ZA791312A patent/ZA791312B/xx unknown
- 1979-03-20 NO NO790929A patent/NO790929L/no unknown
- 1979-03-20 DK DK114579A patent/DK114579A/da not_active Application Discontinuation
- 1979-03-20 SE SE7902519A patent/SE7902519L/ not_active Application Discontinuation
- 1979-03-20 BR BR7901716A patent/BR7901716A/pt unknown
- 1979-03-21 DE DE2911104A patent/DE2911104C2/de not_active Expired
- 1979-03-21 IT IT21184/79A patent/IT1112957B/it active
- 1979-03-21 BE BE0/194135A patent/BE874994A/xx not_active IP Right Cessation
- 1979-03-21 DE DE2953697A patent/DE2953697C2/de not_active Expired
- 1979-03-21 NL NLAANVRAGE7902227,A patent/NL179459C/xx not_active IP Right Cessation
- 1979-03-21 FR FR7907176A patent/FR2420549A1/fr active Granted
- 1979-08-27 ES ES483682A patent/ES483682A1/es not_active Expired
-
1980
- 1980-06-26 JP JP8719580A patent/JPS5639141A/ja active Pending
- 1980-06-26 JP JP8719480A patent/JPS5649724A/ja active Pending
-
1981
- 1981-08-31 SE SE8105138A patent/SE8105138L/ not_active Application Discontinuation
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1113196A (en) | Phenolic resin-polyisocyanate binders | |
| US3905934A (en) | Phenolic resin-polyisocyanate binder systems containing dialkyl phthalate solvents | |
| CA1299795C (en) | Self-setting urethane adhesive paste system | |
| US3676392A (en) | Resin compositions | |
| US4293480A (en) | Urethane binder compositions for no-bake and cold box foundry application utilizing isocyanato-urethane polymers | |
| US4079031A (en) | Improved foundry process and binder resin composition therefor | |
| JPS61501376A (ja) | ハロゲン化りんを含有するフエノ−ル樹脂−ポリイソシアネ−ト結合剤系およびその使用 | |
| DE3750509T2 (de) | Phenolharz-polyisocyanat-bindemittel-systeme, die organophosphate enthalten. | |
| PL191929B1 (pl) | Układ spoiwowy, masa formierska i sposób wytwarzania rdzeni i form odlewniczych na osnowie poliuretanu | |
| DE102015201614A1 (de) | Zweikomponenten-Bindemittelsystem für den Polyurethan-Cold-Box-Prozess | |
| US4317896A (en) | Foundry no-bake combination resin binder | |
| EP3426709A1 (de) | Zweikomponenten-bindemittelsystem für den polyurethan-cold-box-prozess | |
| DE202011110579U1 (de) | Sulfonsäure enthaltendes Bindemittel für Formstoff-Mischungen zur Herstellung von Formen und Kernen | |
| DE2427897A1 (de) | Poroese, praktisch schaumfreie verbundkoerper | |
| US4273179A (en) | Phenolic resin-polyisocyanate binder systems containing dibasic ester solvents | |
| JP2002524260A (ja) | アミン硬化鋳型用結合剤及びそれらの用途 | |
| US4448907A (en) | Process for casting lightweight metals | |
| US4273700A (en) | Polyol resin binder compositions and process | |
| US4370463A (en) | Process for no-bake foundry application utilizing polyurethanes based on amine polyols | |
| US5043365A (en) | Novel molding materials | |
| US5852071A (en) | Biphenyl additive for improvement in urethane foundry binders | |
| US4144215A (en) | Binders for foundry mixes comprising polyisocyanate and styrene-allyl alcohol copolymer or alkylene oxide derivative thereof | |
| AU749009B2 (en) | Foundry binders containing modified polyisocyanates | |
| KR810001792B1 (ko) | 페놀성 수지 폴리이소시아네이트 결합제 조성물 | |
| US3796583A (en) | Process for making foundry molds |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |