CA1122737A - Agents de liaison contenant des resines phenoliques et des solvants a carbonates ou a phosphates de composes organiques - Google Patents

Agents de liaison contenant des resines phenoliques et des solvants a carbonates ou a phosphates de composes organiques

Info

Publication number: CA1122737A
Authority: CA; Canada
Prior art keywords: binder composition; composition according; catalyst; phenolic; solvent
Prior art date: 1978-02-21
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

Application number

CA321,488A

Other languages

English (en)

Inventor

Robert A. Laitar

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Unilever Bestfoods North America

Original Assignee

Unilever Bestfoods North America

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1978-02-21

Filing date

1979-02-14

Publication date

1982-04-27

1979-02-14 Application filed by Unilever Bestfoods North America filed Critical Unilever Bestfoods North America

1982-04-27 Application granted granted Critical

1982-04-27 Publication of CA1122737A publication Critical patent/CA1122737A/fr

Status Expired legal-status Critical Current

Links

239000000203 mixture Substances 0.000 title claims abstract description 87
239000011230 binding agent Substances 0.000 title claims abstract description 59
239000002904 solvent Substances 0.000 title claims abstract description 52
229920001568 phenolic resin Polymers 0.000 title claims abstract description 36
239000005011 phenolic resin Substances 0.000 title claims abstract description 36
229910019142 PO4 Inorganic materials 0.000 title claims abstract description 23
239000010452 phosphate Substances 0.000 title claims abstract description 20
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 title claims abstract description 19
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 title description 6
229920005989 resin Polymers 0.000 claims abstract description 51
239000011347 resin Substances 0.000 claims abstract description 51
239000003054 catalyst Substances 0.000 claims abstract description 45
238000000034 method Methods 0.000 claims abstract description 42
239000000463 material Substances 0.000 claims abstract description 34
KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 claims abstract description 33
239000004576 sand Substances 0.000 claims abstract description 33
230000008569 process Effects 0.000 claims abstract description 31
239000012948 isocyanate Substances 0.000 claims abstract description 29
150000002513 isocyanates Chemical class 0.000 claims abstract description 29
-1 carbonate ester Chemical class 0.000 claims abstract description 27
229920003987 resole Polymers 0.000 claims abstract description 18
238000006243 chemical reaction Methods 0.000 claims abstract description 11
239000003495 polar organic solvent Substances 0.000 claims abstract description 9
229920003986 novolac Polymers 0.000 claims abstract description 6
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 31
QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 claims description 27
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 24
239000004215 Carbon black (E152) Substances 0.000 claims description 15
229930195733 hydrocarbon Natural products 0.000 claims description 15
125000003118 aryl group Chemical group 0.000 claims description 12
150000002430 hydrocarbons Chemical class 0.000 claims description 12
125000004432 carbon atom Chemical group C* 0.000 claims description 9
239000011248 coating agent Substances 0.000 claims description 9
238000000576 coating method Methods 0.000 claims description 9
125000000217 alkyl group Chemical group 0.000 claims description 8
229920001228 polyisocyanate Polymers 0.000 claims description 8
239000005056 polyisocyanate Substances 0.000 claims description 8
229940086542 triethylamine Drugs 0.000 claims description 8
150000004649 carbonic acid derivatives Chemical class 0.000 claims description 6
150000002895 organic esters Chemical class 0.000 claims description 6
150000003512 tertiary amines Chemical group 0.000 claims description 6
238000009835 boiling Methods 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
RYUJRXVZSJCHDZ-UHFFFAOYSA-N 8-methylnonyl diphenyl phosphate Chemical group C=1C=CC=CC=1OP(=O)(OCCCCCCCC(C)C)OC1=CC=CC=C1 RYUJRXVZSJCHDZ-UHFFFAOYSA-N 0.000 claims description 3
229920000538 Poly[(phenyl isocyanate)-co-formaldehyde] Polymers 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 3
150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 3
150000003254 radicals Chemical class 0.000 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
239000000460 chlorine Chemical group 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
150000005676 cyclic carbonates Chemical class 0.000 claims description 2
DAZXVJBJRMWXJP-UHFFFAOYSA-N n,n-dimethylethylamine Chemical group CCN(C)C DAZXVJBJRMWXJP-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
125000003107 substituted aryl group Chemical group 0.000 claims description 2
239000000306 component Substances 0.000 claims 16
235000013824 polyphenols Nutrition 0.000 claims 5
239000006087 Silane Coupling Agent Substances 0.000 claims 1
125000002029 aromatic hydrocarbon group Chemical group 0.000 claims 1
125000001183 hydrocarbyl group Chemical group 0.000 claims 1
238000004519 manufacturing process Methods 0.000 abstract description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 33
WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Substances O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 23
239000000243 solution Substances 0.000 description 21
235000021317 phosphate Nutrition 0.000 description 18
150000002989 phenols Chemical class 0.000 description 14
239000007788 liquid Substances 0.000 description 9
239000002798 polar solvent Substances 0.000 description 9
150000001299 aldehydes Chemical class 0.000 description 8
238000012360 testing method Methods 0.000 description 7
DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 6
150000002148 esters Chemical class 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 4
239000000654 additive Substances 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
239000003849 aromatic solvent Substances 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
238000005266 casting Methods 0.000 description 4
238000005755 formation reaction Methods 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 4
238000002156 mixing Methods 0.000 description 4
RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 4
229910000077 silane Inorganic materials 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
230000007547 defect Effects 0.000 description 3
229960002380 dibutyl phthalate Drugs 0.000 description 3
ASMQGLCHMVWBQR-UHFFFAOYSA-M diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)([O-])OC1=CC=CC=C1 ASMQGLCHMVWBQR-UHFFFAOYSA-M 0.000 description 3
230000003628 erosive effect Effects 0.000 description 3
239000012530 fluid Substances 0.000 description 3
150000002902 organometallic compounds Chemical class 0.000 description 3
229920001296 polysiloxane Polymers 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 2
VTCDZPUMZAZMSB-UHFFFAOYSA-N 3,4,5-trimethoxyphenol Chemical compound COC1=CC(O)=CC(OC)=C1OC VTCDZPUMZAZMSB-UHFFFAOYSA-N 0.000 description 2
FDQQNNZKEJIHMS-UHFFFAOYSA-N 3,4,5-trimethylphenol Chemical compound CC1=CC(O)=CC(C)=C1C FDQQNNZKEJIHMS-UHFFFAOYSA-N 0.000 description 2
YCOXTKKNXUZSKD-UHFFFAOYSA-N 3,4-xylenol Chemical compound CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 2
XQDNFAMOIPNVES-UHFFFAOYSA-N 3,5-Dimethoxyphenol Chemical compound COC1=CC(O)=CC(OC)=C1 XQDNFAMOIPNVES-UHFFFAOYSA-N 0.000 description 2
LPCJHUPMQKSPDC-UHFFFAOYSA-N 3,5-diethylphenol Chemical compound CCC1=CC(O)=CC(CC)=C1 LPCJHUPMQKSPDC-UHFFFAOYSA-N 0.000 description 2
TUAMRELNJMMDMT-UHFFFAOYSA-N 3,5-xylenol Chemical compound CC1=CC(C)=CC(O)=C1 TUAMRELNJMMDMT-UHFFFAOYSA-N 0.000 description 2
HMNKTRSOROOSPP-UHFFFAOYSA-N 3-Ethylphenol Chemical compound CCC1=CC=CC(O)=C1 HMNKTRSOROOSPP-UHFFFAOYSA-N 0.000 description 2
MBGGFXOXUIDRJD-UHFFFAOYSA-N 4-Butoxyphenol Chemical compound CCCCOC1=CC=C(O)C=C1 MBGGFXOXUIDRJD-UHFFFAOYSA-N 0.000 description 2
ZSBDGXGICLIJGD-UHFFFAOYSA-N 4-phenoxyphenol Chemical compound C1=CC(O)=CC=C1OC1=CC=CC=C1 ZSBDGXGICLIJGD-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
235000008733 Citrus aurantifolia Nutrition 0.000 description 2
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 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
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 2
235000011941 Tilia x europaea Nutrition 0.000 description 2
241000287433 Turdus Species 0.000 description 2
ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 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
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
125000001743 benzylic group Chemical group 0.000 description 2
210000000988 bone and bone Anatomy 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
230000003197 catalytic effect Effects 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
239000000470 constituent Substances 0.000 description 2
239000007822 coupling agent Substances 0.000 description 2
230000018044 dehydration Effects 0.000 description 2
238000006297 dehydration reaction Methods 0.000 description 2
230000001419 dependent effect Effects 0.000 description 2
238000011161 development Methods 0.000 description 2
230000018109 developmental process Effects 0.000 description 2
QLVWOKQMDLQXNN-UHFFFAOYSA-N dibutyl carbonate Chemical compound CCCCOC(=O)OCCCC QLVWOKQMDLQXNN-UHFFFAOYSA-N 0.000 description 2
239000007789 gas Substances 0.000 description 2
LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
239000004571 lime Substances 0.000 description 2
RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
125000004433 nitrogen atom Chemical group N* 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
239000002245 particle Substances 0.000 description 2
150000003013 phosphoric acid derivatives Chemical class 0.000 description 2
150000003014 phosphoric acid esters Chemical class 0.000 description 2
238000010944 pre-mature reactiony Methods 0.000 description 2
239000000047 product Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000011342 resin composition Substances 0.000 description 2
150000004756 silanes Chemical class 0.000 description 2
239000007787 solid Substances 0.000 description 2
STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 2
DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
YZYKBQUWMPUVEN-UHFFFAOYSA-N zafuleptine Chemical compound OC(=O)CCCCCC(C(C)C)NCC1=CC=C(F)C=C1 YZYKBQUWMPUVEN-UHFFFAOYSA-N 0.000 description 2
239000004246 zinc acetate Substances 0.000 description 2
NGZXDRGWBULKFA-NSOVKSMOSA-N (+)-Bebeerine Chemical compound C([C@@H]1N(C)CCC=2C=C(C(=C(OC3=CC=C(C=C3)C[C@H]3C=4C=C(C(=CC=4CCN3C)OC)O3)C=21)O)OC)C1=CC=C(O)C3=C1 NGZXDRGWBULKFA-NSOVKSMOSA-N 0.000 description 1
YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-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
TYAVZNXBZYLFGD-UHFFFAOYSA-N 2,2,2-triethoxyethyl dihydrogen phosphate Chemical compound CCOC(OCC)(OCC)COP(O)(O)=O TYAVZNXBZYLFGD-UHFFFAOYSA-N 0.000 description 1
JJJPNTQYUJPWGQ-UHFFFAOYSA-N 2-(3-Phenylpropyl)pyridine Chemical compound C=1C=CC=NC=1CCCC1=CC=CC=C1 JJJPNTQYUJPWGQ-UHFFFAOYSA-N 0.000 description 1
MMEDJBFVJUFIDD-UHFFFAOYSA-N 2-[2-(carboxymethyl)phenyl]acetic acid Chemical compound OC(=O)CC1=CC=CC=C1CC(O)=O MMEDJBFVJUFIDD-UHFFFAOYSA-N 0.000 description 1
NQBXSWAWVZHKBZ-UHFFFAOYSA-N 2-butoxyethyl acetate Chemical compound CCCCOCCOC(C)=O NQBXSWAWVZHKBZ-UHFFFAOYSA-N 0.000 description 1
IWTFOFMTUOBLHG-UHFFFAOYSA-N 2-methoxypyridine Chemical compound COC1=CC=CC=N1 IWTFOFMTUOBLHG-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
HRUHVKFKXJGKBQ-UHFFFAOYSA-N 3,5-dibutylphenol Chemical compound CCCCC1=CC(O)=CC(CCCC)=C1 HRUHVKFKXJGKBQ-UHFFFAOYSA-N 0.000 description 1
PEZSSBYAUDZEMO-UHFFFAOYSA-N 3,5-dicyclohexylphenol Chemical compound C=1C(O)=CC(C2CCCCC2)=CC=1C1CCCCC1 PEZSSBYAUDZEMO-UHFFFAOYSA-N 0.000 description 1
PWRBCZZQRRPXAB-UHFFFAOYSA-N 3-chloropyridine Chemical compound ClC1=CC=CN=C1 PWRBCZZQRRPXAB-UHFFFAOYSA-N 0.000 description 1
UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 description 1
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 1
LKVFCSWBKOVHAH-UHFFFAOYSA-N 4-Ethoxyphenol Chemical compound CCOC1=CC=C(O)C=C1 LKVFCSWBKOVHAH-UHFFFAOYSA-N 0.000 description 1
CHQPRDVSUIJJNP-NSCUHMNNSA-N 4-[(e)-but-2-enyl]phenol Chemical compound C\C=C\CC1=CC=C(O)C=C1 CHQPRDVSUIJJNP-NSCUHMNNSA-N 0.000 description 1
ILASIIGKRFKNQC-UHFFFAOYSA-N 4-methoxy-3-methylphenol Chemical compound COC1=CC=C(O)C=C1C ILASIIGKRFKNQC-UHFFFAOYSA-N 0.000 description 1
ZNPSUQQXTRRSBM-UHFFFAOYSA-N 4-n-Pentylphenol Chemical compound CCCCCC1=CC=C(O)C=C1 ZNPSUQQXTRRSBM-UHFFFAOYSA-N 0.000 description 1
NTDQQZYCCIDJRK-UHFFFAOYSA-N 4-octylphenol Chemical compound CCCCCCCCC1=CC=C(O)C=C1 NTDQQZYCCIDJRK-UHFFFAOYSA-N 0.000 description 1
235000007575 Calluna vulgaris Nutrition 0.000 description 1
SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
239000004593 Epoxy Substances 0.000 description 1
101100176848 Escherichia phage N15 gene 15 gene Proteins 0.000 description 1
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
235000019738 Limestone Nutrition 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
241001272996 Polyphylla fullo Species 0.000 description 1
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
GTVWRXDRKAHEAD-UHFFFAOYSA-N Tris(2-ethylhexyl) phosphate Chemical compound CCCCC(CC)COP(=O)(OCC(CC)CCCC)OCC(CC)CCCC GTVWRXDRKAHEAD-UHFFFAOYSA-N 0.000 description 1
IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
230000006978 adaptation Effects 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical compound C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 description 1
ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 1
239000000378 calcium silicate Substances 0.000 description 1
229910052918 calcium silicate Inorganic materials 0.000 description 1
OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 1
239000007809 chemical reaction catalyst Substances 0.000 description 1
239000004927 clay Substances 0.000 description 1
230000001427 coherent effect Effects 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000013256 coordination polymer Substances 0.000 description 1
125000000853 cresyl group Chemical group C1(=CC=C(C=C1)C)* 0.000 description 1
230000007423 decrease Effects 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
230000002950 deficient Effects 0.000 description 1
150000004985 diamines Chemical class 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
MGWAVDBGNNKXQV-UHFFFAOYSA-N diisobutyl phthalate Chemical compound CC(C)COC(=O)C1=CC=CC=C1C(=O)OCC(C)C MGWAVDBGNNKXQV-UHFFFAOYSA-N 0.000 description 1
125000005442 diisocyanate group Chemical group 0.000 description 1
XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
VUPKGFBOKBGHFZ-UHFFFAOYSA-N dipropyl carbonate Chemical compound CCCOC(=O)OCCC VUPKGFBOKBGHFZ-UHFFFAOYSA-N 0.000 description 1
238000010494 dissociation reaction Methods 0.000 description 1
230000005593 dissociations Effects 0.000 description 1
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 1
JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
235000013312 flour Nutrition 0.000 description 1
SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 1
HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 1
JVZRCNQLWOELDU-UHFFFAOYSA-N gamma-Phenylpyridine Natural products C1=CC=CC=C1C1=CC=NC=C1 JVZRCNQLWOELDU-UHFFFAOYSA-N 0.000 description 1
229960001867 guaiacol Drugs 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
150000004677 hydrates Chemical class 0.000 description 1
150000002540 isothiocyanates Chemical class 0.000 description 1
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 1
239000006028 limestone Substances 0.000 description 1
238000005058 metal casting Methods 0.000 description 1
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
MXHTZQSKTCCMFG-UHFFFAOYSA-N n,n-dibenzyl-1-phenylmethanamine Chemical compound C=1C=CC=CC=1CN(CC=1C=CC=CC=1)CC1=CC=CC=C1 MXHTZQSKTCCMFG-UHFFFAOYSA-N 0.000 description 1
GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
QGZKDVFQNNGYKY-NJFSPNSNSA-N nitrogen-16 Chemical compound [16NH3] QGZKDVFQNNGYKY-NJFSPNSNSA-N 0.000 description 1
150000002883 o-cresols Chemical class 0.000 description 1
125000005474 octanoate group Chemical group 0.000 description 1
YAFOVCNAQTZDQB-UHFFFAOYSA-N octyl diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)(OCCCCCCCC)OC1=CC=CC=C1 YAFOVCNAQTZDQB-UHFFFAOYSA-N 0.000 description 1
150000005677 organic carbonates Chemical class 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
150000001282 organosilanes Chemical class 0.000 description 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
239000011236 particulate material Substances 0.000 description 1
229920000768 polyamine Polymers 0.000 description 1
229920005862 polyol Polymers 0.000 description 1
150000003077 polyols Chemical class 0.000 description 1
229920006389 polyphenyl polymer Polymers 0.000 description 1
239000004814 polyurethane Substances 0.000 description 1
229920002635 polyurethane Polymers 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
238000012545 processing Methods 0.000 description 1
239000001294 propane Substances 0.000 description 1
150000004892 pyridazines Chemical class 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000012260 resinous material Substances 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
238000007493 shaping process Methods 0.000 description 1
FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical class [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
125000005372 silanol group Chemical class 0.000 description 1
239000000377 silicon dioxide Substances 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
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
TXDNPSYEJHXKMK-UHFFFAOYSA-N sulfanylsilane Chemical class S[SiH3] TXDNPSYEJHXKMK-UHFFFAOYSA-N 0.000 description 1
238000009864 tensile test Methods 0.000 description 1
239000012970 tertiary amine catalyst Substances 0.000 description 1
RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
238000012549 training Methods 0.000 description 1
QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 1
HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 description 1
BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1
RXPQRKFMDQNODS-UHFFFAOYSA-N tripropyl phosphate Chemical compound CCCOP(=O)(OCCC)OCCC RXPQRKFMDQNODS-UHFFFAOYSA-N 0.000 description 1
KOWVWXQNQNCRRS-UHFFFAOYSA-N tris(2,4-dimethylphenyl) phosphate Chemical compound CC1=CC(C)=CC=C1OP(=O)(OC=1C(=CC(C)=CC=1)C)OC1=CC=C(C)C=C1C KOWVWXQNQNCRRS-UHFFFAOYSA-N 0.000 description 1
WTLBZVNBAKMVDP-UHFFFAOYSA-N tris(2-butoxyethyl) phosphate Chemical compound CCCCOCCOP(=O)(OCCOCCCC)OCCOCCCC WTLBZVNBAKMVDP-UHFFFAOYSA-N 0.000 description 1
239000002023 wood Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
- C08J3/09—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in organic liquids
- C08J3/091—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in organic liquids characterised by the chemical constitution of the organic liquid
- 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
- B22C1/2246—Condensation polymers of aldehydes and ketones
- B22C1/2253—Condensation polymers of aldehydes and ketones with phenols
- 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
- 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
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2375/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
- C08J2375/04—Polyurethanes

Landscapes

Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Polymers & Plastics (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Dispersion Chemistry (AREA)
General Chemical & Material Sciences (AREA)
Materials Engineering (AREA)
Mechanical Engineering (AREA)
Mold Materials And Core Materials (AREA)
Polyurethanes Or Polyureas (AREA)
Compositions Of Macromolecular Compounds (AREA)

CA321,488A 1978-02-21 1979-02-14 Agents de liaison contenant des resines phenoliques et des solvants a carbonates ou a phosphates de composes organiques Expired CA1122737A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US87977078A	1978-02-21	1978-02-21
US879,770		1978-02-21

Publications (1)

Publication Number	Publication Date
CA1122737A true CA1122737A (fr)	1982-04-27

Family

ID=25374860

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA321,488A Expired CA1122737A (fr)	1978-02-21	1979-02-14	Agents de liaison contenant des resines phenoliques et des solvants a carbonates ou a phosphates de composes organiques

Country Status (12)

Country	Link
JP (1)	JPS54122395A (fr)
BE (1)	BE874291A (fr)
BR (1)	BR7901073A (fr)
CA (1)	CA1122737A (fr)
DE (1)	DE2906052A1 (fr)
ES (2)	ES477879A1 (fr)
FR (1)	FR2417356A1 (fr)
GB (1)	GB2015011B (fr)
IT (1)	IT1110201B (fr)
NL (1)	NL7901390A (fr)
SE (1)	SE7901445L (fr)
ZA (1)	ZA79824B (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3507061A1 (de) *	1984-03-05	1986-09-18	American Hoechst Corp., Somerville, N.J.	Verfahren zur herstellung von urethangruppen enthaltenden phenol-formaldehyd-kondensationsharzen sowie lichtempfindliches gemisch, das solche harze enthaelt
US4788083A (en) *	1986-03-27	1988-11-29	Ashland Oil, Inc.	Tin or bismuth complex catalysts and trigger cure of coatings therewith
DE4135572A1 (de) *	1991-10-29	1993-05-06	Bayer Ag, 5090 Leverkusen, De	Hydrophobe polyurethan-systeme
CN110997179B (zh) *	2017-07-18	2022-03-29	Ha国际有限责任公司	用于具有酯载体的耐火涂料的组合物和方法
KR102162496B1 (ko) *	2018-03-28	2020-10-07	주식회사 엘지화학	수지 조성물
DE102020118148A1 (de)	2020-07-09	2022-01-13	Bindur Gmbh	Formstoff zur Herstellung von Kernen und Verfahren zu dessen Härtung

1979
- 1979-02-14 CA CA321,488A patent/CA1122737A/fr not_active Expired
- 1979-02-16 DE DE19792906052 patent/DE2906052A1/de not_active Withdrawn
- 1979-02-19 SE SE7901445A patent/SE7901445L/xx not_active Application Discontinuation
- 1979-02-20 GB GB7905934A patent/GB2015011B/en not_active Expired
- 1979-02-20 BE BE2057618A patent/BE874291A/fr unknown
- 1979-02-20 ES ES477879A patent/ES477879A1/es not_active Expired
- 1979-02-20 BR BR7901073A patent/BR7901073A/pt unknown
- 1979-02-20 FR FR7904305A patent/FR2417356A1/fr active Pending
- 1979-02-21 NL NL7901390A patent/NL7901390A/xx not_active Application Discontinuation
- 1979-02-21 ZA ZA79824A patent/ZA79824B/xx unknown
- 1979-02-21 JP JP1852179A patent/JPS54122395A/ja active Pending
- 1979-02-21 IT IT20396/78A patent/IT1110201B/it active
- 1979-09-28 ES ES484542A patent/ES484542A1/es not_active Expired

Also Published As

Publication number	Publication date
SE7901445L (sv)	1979-08-22
ZA79824B (en)	1980-04-30
GB2015011B (en)	1982-06-30
ES484542A1 (es)	1980-05-16
IT1110201B (it)	1985-12-23
GB2015011A (en)	1979-09-05
IT7920396A0 (it)	1979-02-21
BE874291A (fr)	1979-06-18
JPS54122395A (en)	1979-09-21
DE2906052A1 (de)	1979-08-30
ES477879A1 (es)	1980-04-01
BR7901073A (pt)	1979-09-11
FR2417356A1 (fr)	1979-09-14
NL7901390A (nl)	1979-08-23

Legal Events

Date	Code	Title	Description
1999-04-27	MKEX	Expiry

Publication	Publication Date	Title
EP0177871B1 (fr)	1990-06-06	Compositions de liants à base de polyuréthane
US4246157A (en)	1981-01-20	Binder compositions containing phenolic resins and organic phosphate and/or carbonate solvents
EP0183782B1 (fr)	1991-09-11	Systemes liants composes de resines phenoliques et de polyisocynates
AU570303B2 (en)	1988-03-10	Phenolic resin-polyisocyanate binder systems
US5733952A (en)	1998-03-31	Foundry binder of phenolic resole resin, polyisocyanate and epoxy resin
US4436881A (en)	1984-03-13	Polyurethane binder compositions
US4982781A (en)	1991-01-08	No-bake process for preparing foundry shapes for casting low melting metal castings
EP0182809A1 (fr)	1986-06-04	Systemes de liants a base de resines phenoliques-polyisocyanate et contenant un acide a base de phosphore.
EP0261775B1 (fr)	1992-06-24	Compositions de liant contenant des résines phénoliques et des esters d'acides alcoxyliques
WO1990005155A1 (fr)	1990-05-17	Liants de fonderie formant polyurethane et contenant un polyester polyol
CA1122737A (fr)	1982-04-27	Agents de liaison contenant des resines phenoliques et des solvants a carbonates ou a phosphates de composes organiques
US4634758A (en)	1987-01-06	Process for preparing alkoxy-modified phenolic resole resins
US5132339A (en)	1992-07-21	Polyurethane-forming foundry binders containing a polyether polyol
US4723592A (en)	1988-02-09	Process for preparing foundry cores and molds
USRE34092E (en)	1992-10-06	Phenolic resin compositions and their use in foundry binders
EP0130584B1 (fr)	1989-05-03	Compositions de liants à base de polyuréthane
US4814363A (en)	1989-03-21	Phenolic resin compositions and their use in foundry binders
CA1118143A (fr)	1982-02-09	Resines de fonderie
US4852636A (en)	1989-08-01	Process for preparing foundry shapes and castings utilizing certain polyurethane binders
CA2346096A1 (fr)	2000-04-06	Liants de fonderie contenant des polyisocyanates modifies
US6883587B2 (en)	2005-04-26	Polyisocyanate compositions and their use
WO1988003541A1 (fr)	1988-05-19	Compositions de liants formant du polyurethane et contenant certains dihalogenures phosphoniques a titre d'agents de prolongation de la duree de vie de telles compositions
JPH0442103B2 (fr)	1992-07-10