CA1170393A - Condensation product and its use - Google Patents
Condensation product and its useInfo
- Publication number
- CA1170393A CA1170393A CA000344837A CA344837A CA1170393A CA 1170393 A CA1170393 A CA 1170393A CA 000344837 A CA000344837 A CA 000344837A CA 344837 A CA344837 A CA 344837A CA 1170393 A CA1170393 A CA 1170393A
- Authority
- CA
- Canada
- Prior art keywords
- phenol
- condensation product
- component
- substituted
- substituted phenol
- 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
- 239000007859 condensation product Substances 0.000 title claims abstract description 18
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 45
- 239000011230 binding agent Substances 0.000 claims abstract description 39
- 239000000203 mixture Substances 0.000 claims abstract description 38
- -1 p-substituted phenol Chemical class 0.000 claims abstract description 27
- 239000003054 catalyst Substances 0.000 claims abstract description 25
- 238000000465 moulding Methods 0.000 claims abstract description 23
- 238000000034 method Methods 0.000 claims abstract description 21
- 230000008569 process Effects 0.000 claims abstract description 15
- 239000012454 non-polar solvent Substances 0.000 claims abstract description 11
- 150000002989 phenols Chemical class 0.000 claims abstract description 11
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 11
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 11
- 239000004814 polyurethane Substances 0.000 claims abstract description 9
- 229920002635 polyurethane Polymers 0.000 claims abstract description 8
- 239000004576 sand Substances 0.000 claims abstract description 8
- 238000005266 casting Methods 0.000 claims abstract description 3
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims abstract 6
- 238000009833 condensation Methods 0.000 claims description 12
- 230000005494 condensation Effects 0.000 claims description 11
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 claims description 8
- 238000009835 boiling Methods 0.000 claims description 7
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 claims description 5
- 238000006482 condensation reaction Methods 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- LCHKCTMHTDXNME-UHFFFAOYSA-N 4-(1-ethylcyclohexyl)phenol Chemical compound C=1C=C(O)C=CC=1C1(CC)CCCCC1 LCHKCTMHTDXNME-UHFFFAOYSA-N 0.000 claims description 4
- OAHMVZYHIJQTQC-UHFFFAOYSA-N 4-cyclohexylphenol Chemical compound C1=CC(O)=CC=C1C1CCCCC1 OAHMVZYHIJQTQC-UHFFFAOYSA-N 0.000 claims description 4
- IGFHQQFPSIBGKE-UHFFFAOYSA-N 4-nonylphenol Chemical compound CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 claims description 4
- NTDQQZYCCIDJRK-UHFFFAOYSA-N 4-octylphenol Chemical compound CCCCCCCCC1=CC=C(O)C=C1 NTDQQZYCCIDJRK-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 150000001735 carboxylic acids Chemical class 0.000 claims description 2
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 2
- 229930195729 fatty acid Natural products 0.000 claims description 2
- 239000000194 fatty acid Substances 0.000 claims description 2
- 150000004665 fatty acids Chemical class 0.000 claims description 2
- 229910052745 lead Inorganic materials 0.000 claims description 2
- 229910052748 manganese Inorganic materials 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 229910052718 tin Inorganic materials 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims 1
- 238000012545 processing Methods 0.000 description 25
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 21
- 239000011347 resin Substances 0.000 description 21
- 229920005989 resin Polymers 0.000 description 21
- 239000000306 component Substances 0.000 description 19
- 239000005011 phenolic resin Substances 0.000 description 17
- 239000000243 solution Substances 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 239000002798 polar solvent Substances 0.000 description 11
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 7
- 229960004279 formaldehyde Drugs 0.000 description 7
- 235000019256 formaldehyde Nutrition 0.000 description 7
- 229910000077 silane Inorganic materials 0.000 description 7
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- AOGQPLXWSUTHQB-UHFFFAOYSA-N hexyl acetate Chemical compound CCCCCCOC(C)=O AOGQPLXWSUTHQB-UHFFFAOYSA-N 0.000 description 6
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 6
- 150000003505 terpenes Chemical class 0.000 description 6
- 235000007586 terpenes Nutrition 0.000 description 6
- 150000001299 aldehydes Chemical class 0.000 description 5
- 102100035115 Testin Human genes 0.000 description 4
- 101710070533 Testin Proteins 0.000 description 4
- 230000009471 action Effects 0.000 description 4
- 238000005452 bending Methods 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000003849 aromatic solvent Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000002444 silanisation Methods 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 description 3
- PYGXAGIECVVIOZ-UHFFFAOYSA-N Dibutyl decanedioate Chemical compound CCCCOC(=O)CCCCCCCCC(=O)OCCCC PYGXAGIECVVIOZ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000011877 solvent mixture Substances 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- 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
- CCCIYAQYQZQDIZ-UHFFFAOYSA-N 6-methylheptan-3-one Chemical compound CCC(=O)CCC(C)C CCCIYAQYQZQDIZ-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- ZCLXSHAPWJCNKK-UHFFFAOYSA-N acetaldehyde 2-ethylbutanoic acid Chemical compound CC=O.CCC(CC)C(O)=O ZCLXSHAPWJCNKK-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 150000001913 cyanates Chemical class 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229940087305 limonene Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- WSFQLUVWDKCYSW-UHFFFAOYSA-M sodium;2-hydroxy-3-morpholin-4-ylpropane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)CC(O)CN1CCOCC1 WSFQLUVWDKCYSW-UHFFFAOYSA-M 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000011701 zinc 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
- 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
- C08G8/24—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ with mixtures of two or more phenols which are not covered by only one of the groups C08G8/10 - C08G8/20
-
- 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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Materials Engineering (AREA)
- Mechanical Engineering (AREA)
- Mold Materials And Core Materials (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polyurethanes Or Polyureas (AREA)
- Phenolic Resins Or Amino Resins (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2904961A DE2904961C2 (de) | 1979-02-03 | 1979-02-03 | Bindemittel für Gießerei-Formstoffmischungen |
| DEP2904961.4 | 1979-02-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1170393A true CA1170393A (en) | 1984-07-03 |
Family
ID=6062575
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000344837A Expired CA1170393A (en) | 1979-02-03 | 1980-01-31 | Condensation product and its use |
Country Status (12)
| Country | Link |
|---|---|
| EP (1) | EP0014855B1 (https=) |
| JP (1) | JPS55137121A (https=) |
| AT (1) | AT385274B (https=) |
| BR (1) | BR8000644A (https=) |
| CA (1) | CA1170393A (https=) |
| DE (1) | DE2904961C2 (https=) |
| ES (1) | ES478882A1 (https=) |
| IN (1) | IN152366B (https=) |
| IT (1) | IT1124672B (https=) |
| MX (1) | MX154448A (https=) |
| YU (1) | YU23180A (https=) |
| ZA (1) | ZA794570B (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5151341A (en) * | 1989-12-12 | 1992-09-29 | Kim Son N | Radiation-sensitive mixture and production of relief structures |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4590229A (en) * | 1984-06-04 | 1986-05-20 | Ashland Oil, Inc. | Phenolic resin-polyisocyanate binder systems |
| JPS61140981A (ja) * | 1984-12-12 | 1986-06-28 | シャープ株式会社 | 液晶表示パネル |
| DE19738755C2 (de) * | 1997-09-04 | 2002-01-17 | Ashland Suedchemie Kernfest | Phenolharz und Bindemittel für die Herstellung von Formen und Kernen nach dem Phenolharz-Polyurethan-Verfahren |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE884869C (de) * | 1949-07-31 | 1953-07-30 | Kurt Herberts & Co Vormals Ott | Verfahren zur Herstellung von Harzen aus Phenolalkoholen und reaktionsfaehigen Carbonylverbindungen |
| US3227686A (en) * | 1960-09-22 | 1966-01-04 | Continental Can Co | Internally plasticized phenolic resins |
| US3485797A (en) * | 1966-03-14 | 1969-12-23 | Ashland Oil Inc | Phenolic resins containing benzylic ether linkages and unsubstituted para positions |
| DE1770816C3 (de) * | 1968-07-06 | 1973-10-18 | Reichhold-Albert-Chemie Ag, 2000 Hamburg | Verfahren zur Herstellung von flexiblen Phenolharzen |
| GB1278582A (en) * | 1968-08-20 | 1972-06-21 | Bp Chem Int Ltd | Phenolic laminating resins |
| US3624038A (en) * | 1970-11-05 | 1971-11-30 | Johnson & Johnson | Phenol formaldehyde resin consisting of an aryl or alkyl substituted phenol-hcho condensate and an alkaline earth metal carboxylate salt of a hydroxy ring substituted aromatic or phenyl substituted aliphatic acid |
| US4048103A (en) * | 1976-02-09 | 1977-09-13 | Minnesota Mining And Manufacturing Company | Composition based on phenolic resin, polyisocyanate, and petroleum oil |
-
1979
- 1979-02-03 DE DE2904961A patent/DE2904961C2/de not_active Expired
- 1979-03-22 ES ES478882A patent/ES478882A1/es not_active Expired
- 1979-08-29 ZA ZA00794570A patent/ZA794570B/xx unknown
- 1979-10-26 IT IT26826/79A patent/IT1124672B/it active
-
1980
- 1980-01-21 AT AT0029880A patent/AT385274B/de not_active IP Right Cessation
- 1980-01-24 EP EP80100360A patent/EP0014855B1/de not_active Expired
- 1980-01-29 YU YU00231/80A patent/YU23180A/xx unknown
- 1980-01-31 MX MX181036A patent/MX154448A/es unknown
- 1980-01-31 CA CA000344837A patent/CA1170393A/en not_active Expired
- 1980-02-01 BR BR8000644A patent/BR8000644A/pt unknown
- 1980-02-04 JP JP1159980A patent/JPS55137121A/ja active Pending
- 1980-02-08 IN IN154/CAL/80A patent/IN152366B/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5151341A (en) * | 1989-12-12 | 1992-09-29 | Kim Son N | Radiation-sensitive mixture and production of relief structures |
Also Published As
| Publication number | Publication date |
|---|---|
| IT1124672B (it) | 1986-05-14 |
| AT385274B (de) | 1988-03-10 |
| ES478882A1 (es) | 1979-11-16 |
| MX154448A (es) | 1987-08-27 |
| DE2904961A1 (de) | 1980-08-07 |
| ZA794570B (en) | 1980-08-27 |
| EP0014855B1 (de) | 1987-01-21 |
| EP0014855A1 (de) | 1980-09-03 |
| BR8000644A (pt) | 1980-10-21 |
| ATA29880A (de) | 1987-08-15 |
| IT7926826A0 (it) | 1979-10-26 |
| DE2904961C2 (de) | 1986-12-11 |
| YU23180A (en) | 1983-09-30 |
| JPS55137121A (en) | 1980-10-25 |
| IN152366B (https=) | 1983-12-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |