DE2702806A1 - Verfahren zum herstellen von phenol- formaldehyd-harzen - Google Patents
Verfahren zum herstellen von phenol- formaldehyd-harzenInfo
- Publication number
- DE2702806A1 DE2702806A1 DE19772702806 DE2702806A DE2702806A1 DE 2702806 A1 DE2702806 A1 DE 2702806A1 DE 19772702806 DE19772702806 DE 19772702806 DE 2702806 A DE2702806 A DE 2702806A DE 2702806 A1 DE2702806 A1 DE 2702806A1
- Authority
- DE
- Germany
- Prior art keywords
- reaction
- phenol
- formaldehyde
- viscosity
- reaction product
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 31
- 229920005989 resin Polymers 0.000 title claims description 29
- 239000011347 resin Substances 0.000 title claims description 29
- 229920001568 phenolic resin Polymers 0.000 title claims description 13
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 title claims 2
- 238000004519 manufacturing process Methods 0.000 title description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 104
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 47
- 238000006243 chemical reaction Methods 0.000 claims description 42
- 239000007795 chemical reaction product Substances 0.000 claims description 25
- 229920003986 novolac Polymers 0.000 claims description 25
- 239000003054 catalyst Substances 0.000 claims description 24
- 239000000047 product Substances 0.000 claims description 24
- 239000007788 liquid Substances 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 13
- 230000002378 acidificating effect Effects 0.000 claims description 11
- 239000011541 reaction mixture Substances 0.000 claims description 10
- 238000001256 steam distillation Methods 0.000 claims description 8
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 claims description 6
- 239000004576 sand Substances 0.000 claims description 6
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- 238000006116 polymerization reaction Methods 0.000 claims description 4
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 3
- 238000005191 phase separation Methods 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 2
- 238000006053 organic reaction Methods 0.000 claims 2
- 230000008030 elimination Effects 0.000 claims 1
- 238000003379 elimination reaction Methods 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000000243 solution Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 6
- 150000002989 phenols Chemical class 0.000 description 6
- 235000011121 sodium hydroxide Nutrition 0.000 description 5
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 229920003987 resole Polymers 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- -1 methylol groups Chemical group 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 238000005266 casting Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000010959 steel 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
- 239000011787 zinc oxide Substances 0.000 description 2
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 238000003723 Smelting Methods 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 231100000206 health hazard Toxicity 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000012432 intermediate storage Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000010413 mother solution Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 238000010979 pH adjustment Methods 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 239000013618 particulate matter Substances 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 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
- C08G8/10—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)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Phenolic Resins Or Amino Resins (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3367/76A GB1556691A (en) | 1976-01-28 | 1976-01-28 | Phenol formaldehyde resins their manufacture and uses |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2702806A1 true DE2702806A1 (de) | 1977-08-11 |
Family
ID=9756988
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19772702806 Pending DE2702806A1 (de) | 1976-01-28 | 1977-01-25 | Verfahren zum herstellen von phenol- formaldehyd-harzen |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4132699A (enExample) |
| DE (1) | DE2702806A1 (enExample) |
| FR (1) | FR2339632A1 (enExample) |
| GB (1) | GB1556691A (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE60015672T2 (de) * | 1999-08-27 | 2005-12-01 | Rohm And Haas Co. | Verfahren zum Abstrippen von Polymerdispersionen oder Polymerlösungen |
| US6569918B2 (en) | 2000-02-04 | 2003-05-27 | Plastics Engineering Company | Polymer composition for curing novolac resins |
| JP4727958B2 (ja) * | 2004-08-19 | 2011-07-20 | 旭有機材工業株式会社 | ノボラック型フェノール樹脂の製造方法 |
| US8133933B2 (en) * | 2005-11-15 | 2012-03-13 | Georgia-Pacific Chemicals Llc | Binder compositions compatible with thermally reclaiming refractory particulate material from molds used in foundry applications |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1737917A (en) * | 1926-04-21 | 1929-12-03 | Economy Fuse And Mfg Company | Phenolic condensation products and process for preparing same |
| US2180981A (en) * | 1937-06-25 | 1939-11-21 | Gen Electric | Process of making phenol-aldehyde resins |
| US2658054A (en) * | 1951-10-31 | 1953-11-03 | Allied Chem & Dye Corp | Continuous resin process |
| US3189566A (en) * | 1958-12-09 | 1965-06-15 | Toyo Kogyo Company Ltd | Liquid resin compositions for shell molding and methods for their production |
-
1976
- 1976-01-28 GB GB3367/76A patent/GB1556691A/en not_active Expired
-
1977
- 1977-01-24 US US05/761,755 patent/US4132699A/en not_active Expired - Lifetime
- 1977-01-25 DE DE19772702806 patent/DE2702806A1/de active Pending
- 1977-01-26 FR FR7702178A patent/FR2339632A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| GB1556691A (en) | 1979-11-28 |
| FR2339632A1 (fr) | 1977-08-26 |
| US4132699A (en) | 1979-01-02 |
| FR2339632B3 (enExample) | 1979-09-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1720204C3 (de) | Verfahren zur Herstellung von Phenol-Formaldehyd-Kondensaten und ihre Verwendung als Bindemittel und in Formmassen | |
| DE1720222A1 (de) | Kunstharzmischung | |
| DE1130174B (de) | Verfahren zur Herstellung von Polyaetherharzen | |
| DE2230904A1 (de) | Zusammensetzungen auf der Basis von Epoxyharzen | |
| DE1816197A1 (de) | Kaeltehaertende Kunstharz-Bindemittel und Verfahren zu ihrer Herstellung | |
| DE2235668C3 (de) | Katalysator für ein Gießereibindemittel | |
| DE2702806A1 (de) | Verfahren zum herstellen von phenol- formaldehyd-harzen | |
| DE2658015A1 (de) | Verfahren zur herstellung eines fluessigen harzes | |
| DE2010532B2 (de) | Verfahren zur Herstellung von Furfuryl-alkohol-Formaldehyd-Vorpolykondensaten und ihre Verwendung | |
| EP0014855B1 (de) | Bindemittel für Giesserei-Formstoffmischungen | |
| DE3022534A1 (de) | Fluessiges novolakharz und aus diesem hergestellte erzeugnisse | |
| DE19856778A1 (de) | Formstoff-Bindemittel | |
| DE1570203C3 (enExample) | ||
| EP0268172A1 (de) | Kalthärtendes Formstoff-Bindemittel und dessen Verwendung | |
| DE569021C (de) | Verfahren zur Herstellung von harzartigen Kondensationsprodukten aus aromatischen Sulfamiden und Aldehyden | |
| DE3332063A1 (de) | Verfahren zur herstellung von benzylaetherharzen als bindemittel fuer giessereisande nach dem cold-box-system | |
| DE1022005B (de) | Verfahren zur Herstellung von Novolakharzen | |
| DE1947964A1 (de) | Verfahren zur Herstellung modifizierter Harze | |
| DE813208C (de) | Verfahren zur Herstellung von Phenol-Aldehydkondensations-Produkten | |
| DE517251C (de) | Verfahren zur Herstellung hydrophober Harze durch Kondensation von Harnstoff oder Harnstoffderivaten mit Aldehyden, insbesondere mit Formaldehyd | |
| DE2857842C2 (de) | Verfahren zur Herstellung von innerlich weichgemachten Phenolharzen | |
| DE3423878A1 (de) | Verfahren zur herstellung von phenol-aldehyd-kondensaten und deren verwendung als bindemittel fuer giessereiformteile | |
| CH449857A (de) | Verfahren zur Herstellung von Sandkernen und -formen | |
| DE1694848B2 (de) | Verfahren zur Härtung saurehartbarer Bindemittel fur Form- und Kernsand auf Basis von Phenolharzen oder Harnstoffharzen | |
| DE868349C (de) | Verfahren zur Herstellung von Kondensationsprodukten |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |