CA1134989A - Cold hardening binder for material mixtures for the production of casting moulds and cores - Google Patents

Cold hardening binder for material mixtures for the production of casting moulds and cores

Info

Publication number: CA1134989A
Authority: CA; Canada
Prior art keywords: groups; polyol; amino; molecule; binder
Prior art date: 1977-12-30
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

CA000318783A

Other languages

English (en)

French (fr)

Inventor

Marek Torbus

Aleksandar Vujevic

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.)

Huettenes Albertus Chemische Werke GmbH

Original Assignee

Huettenes Albertus Chemische Werke GmbH

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.)

1977-12-30

Filing date

1978-12-28

Publication date

1982-11-02

1978-12-28 Application filed by Huettenes Albertus Chemische Werke GmbH filed Critical Huettenes Albertus Chemische Werke GmbH

1982-11-02 Application granted granted Critical

1982-11-02 Publication of CA1134989A publication Critical patent/CA1134989A/en

Status Expired legal-status Critical Current

Links

239000011230 binding agent Substances 0.000 title claims abstract description 40
238000005266 casting Methods 0.000 title claims abstract description 23
239000000203 mixture Substances 0.000 title claims abstract description 22
238000004519 manufacturing process Methods 0.000 title claims abstract description 11
229920005862 polyol Polymers 0.000 claims abstract description 27
-1 amino polyol Chemical class 0.000 claims abstract description 20
125000001302 tertiary amino group Chemical group 0.000 claims abstract description 13
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 10
239000005056 polyisocyanate Substances 0.000 claims abstract description 9
229920001228 polyisocyanate Polymers 0.000 claims abstract description 9
150000003077 polyols Chemical class 0.000 claims abstract description 7
239000004814 polyurethane Substances 0.000 claims abstract description 7
229920002635 polyurethane Polymers 0.000 claims abstract description 6
125000002947 alkylene group Chemical group 0.000 claims description 7
150000001412 amines Chemical class 0.000 claims description 6
150000001875 compounds Chemical class 0.000 claims description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 5
125000003118 aryl group Chemical group 0.000 claims description 4
125000004430 oxygen atom Chemical group O* 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 3
125000000753 cycloalkyl group Chemical group 0.000 claims description 3
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 3
125000003710 aryl alkyl group Chemical group 0.000 claims description 2
125000002993 cycloalkylene group Chemical group 0.000 claims description 2
125000000524 functional group Chemical group 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
238000000465 moulding Methods 0.000 description 13
238000000034 method Methods 0.000 description 9
239000002904 solvent Substances 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 6
239000000243 solution Substances 0.000 description 6
150000003512 tertiary amines Chemical class 0.000 description 5
239000000463 material Substances 0.000 description 4
229920005989 resin Polymers 0.000 description 4
239000011347 resin Substances 0.000 description 4
239000004576 sand Substances 0.000 description 4
238000003860 storage Methods 0.000 description 4
XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-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
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
238000009833 condensation Methods 0.000 description 3
230000005494 condensation Effects 0.000 description 3
XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
239000006004 Quartz sand Substances 0.000 description 2
230000001133 acceleration Effects 0.000 description 2
239000002253 acid Substances 0.000 description 2
229920000180 alkyd Polymers 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
238000005452 bending Methods 0.000 description 2
239000000470 constituent Substances 0.000 description 2
SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000007789 gas Substances 0.000 description 2
NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
239000012948 isocyanate Substances 0.000 description 2
150000002513 isocyanates Chemical class 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
229920005749 polyurethane resin Polymers 0.000 description 2
KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
239000000126 substance 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
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-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
ZWNGZTIBYCJCLU-UHFFFAOYSA-N 1-[3-[bis(2-hydroxypropyl)amino]propyl-(2-hydroxypropyl)amino]propan-2-ol Chemical compound CC(O)CN(CC(C)O)CCCN(CC(C)O)CC(C)O ZWNGZTIBYCJCLU-UHFFFAOYSA-N 0.000 description 1
JWTVQZQPKHXGFM-UHFFFAOYSA-N 2,5-dimethylhexane-2,5-diamine Chemical compound CC(C)(N)CCC(C)(C)N JWTVQZQPKHXGFM-UHFFFAOYSA-N 0.000 description 1
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
SRGQQZYVZFJYHJ-UHFFFAOYSA-N 2-(aminomethyl)cyclopentan-1-amine Chemical compound NCC1CCCC1N SRGQQZYVZFJYHJ-UHFFFAOYSA-N 0.000 description 1
SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 1
YEYKMVJDLWJFOA-UHFFFAOYSA-N 2-propoxyethanol Chemical compound CCCOCCO YEYKMVJDLWJFOA-UHFFFAOYSA-N 0.000 description 1
RXFCIXRFAJRBSG-UHFFFAOYSA-N 3,2,3-tetramine Chemical compound NCCCNCCNCCCN RXFCIXRFAJRBSG-UHFFFAOYSA-N 0.000 description 1
ZAXCZCOUDLENMH-UHFFFAOYSA-N 3,3,3-tetramine Chemical compound NCCCNCCCNCCCN ZAXCZCOUDLENMH-UHFFFAOYSA-N 0.000 description 1
YOOSAIJKYCBPFW-UHFFFAOYSA-N 3-[4-(3-aminopropoxy)butoxy]propan-1-amine Chemical compound NCCCOCCCCOCCCN YOOSAIJKYCBPFW-UHFFFAOYSA-N 0.000 description 1
WECDUOXQLAIPQW-UHFFFAOYSA-N 4,4'-Methylene bis(2-methylaniline) Chemical compound C1=C(N)C(C)=CC(CC=2C=C(C)C(N)=CC=2)=C1 WECDUOXQLAIPQW-UHFFFAOYSA-N 0.000 description 1
YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 1
IGSBHTZEJMPDSZ-UHFFFAOYSA-N 4-[(4-amino-3-methylcyclohexyl)methyl]-2-methylcyclohexan-1-amine Chemical compound C1CC(N)C(C)CC1CC1CC(C)C(N)CC1 IGSBHTZEJMPDSZ-UHFFFAOYSA-N 0.000 description 1
DZIHTWJGPDVSGE-UHFFFAOYSA-N 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1CC1CCC(N)CC1 DZIHTWJGPDVSGE-UHFFFAOYSA-N 0.000 description 1
BDBZTOMUANOKRT-UHFFFAOYSA-N 4-[2-(4-aminocyclohexyl)propan-2-yl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1C(C)(C)C1CCC(N)CC1 BDBZTOMUANOKRT-UHFFFAOYSA-N 0.000 description 1
239000004243 E-number Substances 0.000 description 1
235000019227 E-number Nutrition 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
229920000877 Melamine resin Polymers 0.000 description 1
GWGWXYUPRTXVSY-UHFFFAOYSA-N N=C=O.N=C=O.CC1=CC=C(C)C=C1 Chemical compound N=C=O.N=C=O.CC1=CC=C(C)C=C1 GWGWXYUPRTXVSY-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
239000005700 Putrescine Substances 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000001491 aromatic compounds Chemical class 0.000 description 1
MRNZSTMRDWRNNR-UHFFFAOYSA-N bis(hexamethylene)triamine Chemical compound NCCCCCCNCCCCCCN MRNZSTMRDWRNNR-UHFFFAOYSA-N 0.000 description 1
RGTXVXDNHPWPHH-UHFFFAOYSA-N butane-1,3-diamine Chemical compound CC(N)CCN RGTXVXDNHPWPHH-UHFFFAOYSA-N 0.000 description 1
BELZJFWUNQWBES-UHFFFAOYSA-N caldopentamine Chemical compound NCCCNCCCNCCCNCCCN BELZJFWUNQWBES-UHFFFAOYSA-N 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000013522 chelant Chemical class 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
229910017052 cobalt Inorganic materials 0.000 description 1
239000010941 cobalt Substances 0.000 description 1
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
239000013065 commercial product Substances 0.000 description 1
230000007423 decrease Effects 0.000 description 1
230000007547 defect Effects 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
239000003999 initiator Substances 0.000 description 1
HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 1
GKQPCPXONLDCMU-CCEZHUSRSA-N lacidipine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1C1=CC=CC=C1\C=C\C(=O)OC(C)(C)C GKQPCPXONLDCMU-CCEZHUSRSA-N 0.000 description 1
JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
KMBPCQSCMCEPMU-UHFFFAOYSA-N n'-(3-aminopropyl)-n'-methylpropane-1,3-diamine Chemical compound NCCCN(C)CCCN KMBPCQSCMCEPMU-UHFFFAOYSA-N 0.000 description 1
ITZPOSYADVYECJ-UHFFFAOYSA-N n'-cyclohexylpropane-1,3-diamine Chemical compound NCCCNC1CCCCC1 ITZPOSYADVYECJ-UHFFFAOYSA-N 0.000 description 1
ZMVMYBGDGJLCHV-UHFFFAOYSA-N n-methyl-4-[[4-(methylamino)phenyl]methyl]aniline Chemical compound C1=CC(NC)=CC=C1CC1=CC=C(NC)C=C1 ZMVMYBGDGJLCHV-UHFFFAOYSA-N 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
239000012454 non-polar solvent Substances 0.000 description 1
229910052609 olivine Inorganic materials 0.000 description 1
239000010450 olivine Substances 0.000 description 1
HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 description 1
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
235000011007 phosphoric acid Nutrition 0.000 description 1
229960004838 phosphoric acid Drugs 0.000 description 1
231100000614 poison Toxicity 0.000 description 1
230000007096 poisonous effect Effects 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
239000004645 polyester resin Substances 0.000 description 1
239000004848 polyfunctional curative Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
239000003586 protic polar solvent Substances 0.000 description 1
239000010453 quartz Substances 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
239000001117 sulphuric acid Substances 0.000 description 1
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 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
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3271—Hydroxyamines
- C08G18/3278—Hydroxyamines containing at least three hydroxy groups
- 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
- 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
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3271—Hydroxyamines
- 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
- C08G18/48—Polyethers
- C08G18/50—Polyethers having heteroatoms other than oxygen
- C08G18/5021—Polyethers having heteroatoms other than oxygen having nitrogen

Landscapes

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

CA000318783A 1977-12-30 1978-12-28 Cold hardening binder for material mixtures for the production of casting moulds and cores Expired CA1134989A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE19772759258 DE2759258A1 (de)	1977-12-30	1977-12-30	Kaltaushaertendes bindemittel fuer formstoff-mischungen zur herstellung von giessformen und kernen
DEP2759258.1		1977-12-30

Publications (1)

Publication Number	Publication Date
CA1134989A true CA1134989A (en)	1982-11-02

Family

ID=6027935

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000318783A Expired CA1134989A (en)	1977-12-30	1978-12-28	Cold hardening binder for material mixtures for the production of casting moulds and cores

Country Status (13)

Country	Link
JP (1)	JPS5496426A (it)
AR (1)	AR220366A1 (it)
AU (1)	AU4293878A (it)
BE (1)	BE865741A (it)
BR (1)	BR7808389A (it)
CA (1)	CA1134989A (it)
DE (1)	DE2759258A1 (it)
ES (1)	ES476072A1 (it)
FR (1)	FR2413453A1 (it)
GR (1)	GR66462B (it)
IT (1)	IT1102406B (it)
NL (1)	NL7812549A (it)
ZA (1)	ZA783393B (it)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4370463A (en) *	1978-06-14	1983-01-25	Ashland Oil, Inc.	Process for no-bake foundry application utilizing polyurethanes based on amine polyols
DE2855391A1 (de) *	1978-12-21	1980-06-26	Woellner Werke	Kalthaertendes bindemittel fuer teilchenfoermige feststoffe, insbesondere giessereisand
DE2925733A1 (de) *	1979-06-23	1981-01-15	Huettenes Albertus	Bindemittel auf polyurethanbasis, sowie dessen herstellung
JPS5736115A (en) *	1980-08-12	1982-02-26	Mitsui Tekisako Chem Kk	Curing agent composition for polyurethane
US4448907A (en) *	1981-03-30	1984-05-15	Ashland Oil, Inc.	Process for casting lightweight metals
DE3329452A1 (de) *	1983-08-16	1985-03-07	Bayer Ag, 5090 Leverkusen	Verfahren zur herstellung von gegebenenfalls zellfoermigen polyurethanen

1977
- 1977-12-30 DE DE19772759258 patent/DE2759258A1/de not_active Withdrawn
1978
- 1978-04-06 BE BE186603A patent/BE865741A/xx unknown
- 1978-06-13 ZA ZA00783393A patent/ZA783393B/xx unknown
- 1978-12-16 ES ES476072A patent/ES476072A1/es not_active Expired
- 1978-12-20 IT IT31040/78A patent/IT1102406B/it active
- 1978-12-21 FR FR7836602A patent/FR2413453A1/fr active Granted
- 1978-12-21 BR BR7808389A patent/BR7808389A/pt unknown
- 1978-12-22 GR GR57979A patent/GR66462B/el unknown
- 1978-12-27 JP JP16023878A patent/JPS5496426A/ja active Pending
- 1978-12-27 NL NL7812549A patent/NL7812549A/xx not_active Application Discontinuation
- 1978-12-28 CA CA000318783A patent/CA1134989A/en not_active Expired
- 1978-12-28 AU AU42938/78A patent/AU4293878A/en active Pending
- 1978-12-28 AR AR275018A patent/AR220366A1/es active

Also Published As

Publication number	Publication date
IT1102406B (it)	1985-10-07
AU4293878A (en)	1979-07-05
GR66462B (it)	1981-03-23
FR2413453A1 (fr)	1979-07-27
IT7831040A0 (it)	1978-12-20
AR220366A1 (es)	1980-10-31
ES476072A1 (es)	1979-05-16
BE865741A (fr)	1978-07-31
JPS5496426A (en)	1979-07-30
DE2759258A1 (de)	1979-07-12
ZA783393B (en)	1979-06-27
NL7812549A (nl)	1979-07-03
FR2413453B1 (it)	1983-03-18
BR7808389A (pt)	1979-08-07

Legal Events

Date	Code	Title	Description
1999-11-02	MKEX	Expiry

Publication	Publication Date	Title
US4293480A (en)	1981-10-06	Urethane binder compositions for no-bake and cold box foundry application utilizing isocyanato-urethane polymers
US3590902A (en)	1971-07-06	Production of foundry cores and molds
US3429848A (en)	1969-02-25	Foundry binder composition comprising benzylic ether resin,polyisocyanate,and tertiary amine
US3933727A (en)	1976-01-20	Method of producing polyurethane-based cores and moulds according to the so-called cold-box procedure
CA1251597A (en)	1989-03-21	Polyurethane binder compositions
US3905934A (en)	1975-09-16	Phenolic resin-polyisocyanate binder systems containing dialkyl phthalate solvents
EP2485859B1 (en)	2014-02-26	Lignite-urethane based resins for enhanced foundry sand performance
US4851457A (en)	1989-07-25	Foundry resins
US3632844A (en)	1972-01-04	Non-sticking sand mix for foundry cores
CA1314349C (en)	1993-03-09	Binder compositions containing phenolic resins and esters of alkoxy acids
US4246157A (en)	1981-01-20	Binder compositions containing phenolic resins and organic phosphate and/or carbonate solvents
CA1134989A (en)	1982-11-02	Cold hardening binder for material mixtures for the production of casting moulds and cores
US4051092A (en)	1977-09-27	Foundry core composition of aggregate and a binder therefor
CA1082833A (en)	1980-07-29	Foundry binders
US4448907A (en)	1984-05-15	Process for casting lightweight metals
US4172068A (en)	1979-10-23	Foundry core composition of aggregate and a binder therefor
US4370463A (en)	1983-01-25	Process for no-bake foundry application utilizing polyurethanes based on amine polyols
EP0695594A2 (en)	1996-02-07	Biphenyl additive for improvement in urethane foundry binders
US4516996A (en)	1985-05-14	Formation of molded glass fiber parts from glass fiber blankets and product
US4144215A (en)	1979-03-13	Binders for foundry mixes comprising polyisocyanate and styrene-allyl alcohol copolymer or alkylene oxide derivative thereof
GB2024232A (en)	1980-01-09	Urethane binder for no-bake and cold-box foundry cores and moulds
US4301271A (en)	1981-11-17	Polyurethane-based binder, as well as the production thereof
US3839265A (en)	1974-10-01	Polymeric composition and method
US6387983B1 (en)	2002-05-14	Foundry mixes containing an aliphatic mercaptan
JPS643586B2 (it)	1989-01-23