DE2648051A1 - Polyhydroxiphenole und verfahren zu ihrer herstellung - Google Patents
Polyhydroxiphenole und verfahren zu ihrer herstellungInfo
- Publication number
- DE2648051A1 DE2648051A1 DE19762648051 DE2648051A DE2648051A1 DE 2648051 A1 DE2648051 A1 DE 2648051A1 DE 19762648051 DE19762648051 DE 19762648051 DE 2648051 A DE2648051 A DE 2648051A DE 2648051 A1 DE2648051 A1 DE 2648051A1
- Authority
- DE
- Germany
- Prior art keywords
- acid
- phenol
- process step
- para
- reaction
- 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.)
- Ceased
Links
- 238000000034 method Methods 0.000 title claims description 59
- 238000004519 manufacturing process Methods 0.000 title description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 55
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 36
- 239000002253 acid Substances 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 150000002989 phenols Chemical class 0.000 claims description 18
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 15
- 150000008442 polyphenolic compounds Polymers 0.000 claims description 15
- 239000000243 solution Substances 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 12
- 150000007529 inorganic bases Chemical class 0.000 claims description 11
- 239000003960 organic solvent Substances 0.000 claims description 11
- 239000012429 reaction media Substances 0.000 claims description 11
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 claims description 10
- 239000003054 catalyst Substances 0.000 claims description 10
- 230000002378 acidificating effect Effects 0.000 claims description 9
- 239000007795 chemical reaction product Substances 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 6
- 239000008346 aqueous phase Substances 0.000 claims description 6
- 238000009835 boiling Methods 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 235000006408 oxalic acid Nutrition 0.000 claims description 5
- 239000012071 phase Substances 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 4
- -1 Para-amylphenol Chemical compound 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 4
- 238000010494 dissociation reaction Methods 0.000 claims description 4
- 230000005593 dissociations Effects 0.000 claims description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 4
- 150000007524 organic acids Chemical class 0.000 claims description 4
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims description 4
- 239000003377 acid catalyst Substances 0.000 claims description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 3
- 150000007519 polyprotic acids Polymers 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 3
- IGFHQQFPSIBGKE-UHFFFAOYSA-N 4-nonylphenol Chemical compound CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 claims description 2
- NTDQQZYCCIDJRK-UHFFFAOYSA-N 4-octylphenol Chemical compound CCCCCCCCC1=CC=C(O)C=C1 NTDQQZYCCIDJRK-UHFFFAOYSA-N 0.000 claims description 2
- 239000005711 Benzoic acid Substances 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- 235000010233 benzoic acid Nutrition 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 claims description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims description 2
- 239000002244 precipitate Substances 0.000 claims description 2
- 229960004889 salicylic acid Drugs 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 150000007530 organic bases Chemical class 0.000 claims 1
- 230000001376 precipitating effect Effects 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 238000004817 gas chromatography Methods 0.000 description 4
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- 210000003298 dental enamel Anatomy 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 229920003986 novolac Polymers 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 229920001568 phenolic resin Polymers 0.000 description 2
- 239000005011 phenolic resin Substances 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 229920003987 resole Polymers 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- IJJWOSAXNHWBPR-HUBLWGQQSA-N 5-[(3as,4s,6ar)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]-n-(6-hydrazinyl-6-oxohexyl)pentanamide Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)NCCCCCC(=O)NN)SC[C@@H]21 IJJWOSAXNHWBPR-HUBLWGQQSA-N 0.000 description 1
- 241000984642 Cura Species 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000011874 heated mixture Substances 0.000 description 1
- 239000004312 hexamethylene tetramine Substances 0.000 description 1
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 1
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000003110 molding sand Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- QEVHRUUCFGRFIF-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C(C5=CC=C(OC)C=C5N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 QEVHRUUCFGRFIF-MDEJGZGSSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 235000011008 sodium phosphates Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical class [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 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
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/02—Polycondensates containing more than one epoxy group per molecule
- C08G59/04—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof
- C08G59/06—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof of polyhydric phenols
- C08G59/08—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof of polyhydric phenols from phenol-aldehyde condensates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/12—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings
- C07C39/15—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings with all hydroxy groups on non-condensed rings, e.g. phenylphenol
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Phenolic Resins Or Amino Resins (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2880975A IT1043743B (it) | 1975-10-30 | 1975-10-30 | Fenoli poliussiorilici e procedimento per la loro preparazione |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2648051A1 true DE2648051A1 (de) | 1977-05-18 |
Family
ID=11224223
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762648051 Ceased DE2648051A1 (de) | 1975-10-30 | 1976-10-23 | Polyhydroxiphenole und verfahren zu ihrer herstellung |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS5257153A (enrdf_load_stackoverflow) |
| CA (1) | CA1078874A (enrdf_load_stackoverflow) |
| DE (1) | DE2648051A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2329631A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1493760A (enrdf_load_stackoverflow) |
| IT (1) | IT1043743B (enrdf_load_stackoverflow) |
| NL (1) | NL7612021A (enrdf_load_stackoverflow) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4173541A (en) | 1978-06-05 | 1979-11-06 | Cincinnati Milacron Chemicals Inc. | Polynuclear hindered phenols and stabilized organic materials containing the phenols |
| JPS62119220A (ja) * | 1985-11-18 | 1987-05-30 | Arakawa Chem Ind Co Ltd | ポリヒドロキシ化合物の製造法 |
| WO2005000597A1 (ja) * | 2003-06-25 | 2005-01-06 | Asahi Kasei Chemicals Corporation | 記録材料用顕色剤 |
| JP2005232038A (ja) * | 2004-02-17 | 2005-09-02 | Sumitomo Bakelite Co Ltd | フェノール化合物とその製造方法 |
| WO2006075604A1 (ja) * | 2005-01-11 | 2006-07-20 | Oji Paper Co., Ltd. | 感熱記録体 |
| WO2015175551A1 (en) * | 2014-05-12 | 2015-11-19 | Si Group, Inc. | Modified phenolic resins and methods of making and using the same as reinforcing resins |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE915341C (de) * | 1950-09-06 | 1954-07-19 | Union Carbide & Carbon Corp | Verfahren zur Herstellung von Triphenylolverbindungen |
| US2744882A (en) * | 1949-01-26 | 1956-05-08 | Union Carbide & Carbon Corp | Unsymmetrical diphenylol methanes |
| US2773907A (en) * | 1954-02-05 | 1956-12-11 | American Cyanamid Co | Tris-phenols |
| US2841627A (en) * | 1952-10-10 | 1958-07-01 | Monsanto Chemicals | Method of preserving a rubber with an alpha, alpha'-bis(hydroxyphenyl)-2, 6-xylenol ad resulting compositions |
| DE1205976B (de) * | 1960-12-02 | 1965-12-02 | Distillers Co Yeast Ltd | Verfahren zur Herstellung von 3-Phenolkerne enthaltenden Antioxydationsmitteln |
-
1975
- 1975-10-30 IT IT2880975A patent/IT1043743B/it active
-
1976
- 1976-10-12 GB GB4239176A patent/GB1493760A/en not_active Expired
- 1976-10-19 CA CA263,674A patent/CA1078874A/en not_active Expired
- 1976-10-23 DE DE19762648051 patent/DE2648051A1/de not_active Ceased
- 1976-10-29 FR FR7632819A patent/FR2329631A1/fr active Granted
- 1976-10-29 JP JP13040876A patent/JPS5257153A/ja active Pending
- 1976-10-29 NL NL7612021A patent/NL7612021A/xx not_active Application Discontinuation
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2744882A (en) * | 1949-01-26 | 1956-05-08 | Union Carbide & Carbon Corp | Unsymmetrical diphenylol methanes |
| DE915341C (de) * | 1950-09-06 | 1954-07-19 | Union Carbide & Carbon Corp | Verfahren zur Herstellung von Triphenylolverbindungen |
| US2841627A (en) * | 1952-10-10 | 1958-07-01 | Monsanto Chemicals | Method of preserving a rubber with an alpha, alpha'-bis(hydroxyphenyl)-2, 6-xylenol ad resulting compositions |
| US2773907A (en) * | 1954-02-05 | 1956-12-11 | American Cyanamid Co | Tris-phenols |
| DE1205976B (de) * | 1960-12-02 | 1965-12-02 | Distillers Co Yeast Ltd | Verfahren zur Herstellung von 3-Phenolkerne enthaltenden Antioxydationsmitteln |
Non-Patent Citations (2)
| Title |
|---|
| Beilsteins Handbuch der org. Chemie, 4. Aufl., Bd. 6, 1923, S. 1147 * |
| Houben-Weyl: Methoden der org. Chemie, 4. Aufl., Bd.XIV/2, 1963, S. 224-26 u. 236-37 * |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2329631A1 (fr) | 1977-05-27 |
| JPS5257153A (en) | 1977-05-11 |
| NL7612021A (nl) | 1977-05-03 |
| FR2329631B1 (enrdf_load_stackoverflow) | 1981-12-04 |
| CA1078874A (en) | 1980-06-03 |
| IT1043743B (it) | 1980-02-29 |
| GB1493760A (en) | 1977-11-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69617017T2 (de) | Phenolische polymere erhalten durch aralkylierung | |
| EP0381966B1 (de) | Verfahren zur Herstellung von Novolaken und deren Verwendung | |
| DE2330851B2 (de) | Verfahren zur herstellung von resolen und deren verwendung | |
| DE2648051A1 (de) | Polyhydroxiphenole und verfahren zu ihrer herstellung | |
| DE3422510A1 (de) | Verfahren zur herstellung von ueber o,o'-methylenethergruppen verknuepften phenolresolethern und deren verwendung | |
| DE695178C (de) | Verfahren zur Herstellung von hochmolekularen Verbindungen | |
| DE3324338A1 (de) | Kontinuierliches verfahren zur entfernung des katalysators aus polyphenylenethern | |
| DE2262196A1 (de) | Verfahren zur gewinnung von formaldehyd und phenol aus abwaessern | |
| DE69801019T2 (de) | Hochmolekulares Novolakphenolharz mit hohem Anteil an ortho-Bindungen | |
| EP0152760B1 (de) | Säurehärtbare Mischung für schwindungsarme Furankitte und Verfahren zu deren Herstellung | |
| DE2136254A1 (de) | Verfahren zur Herstellung von Harzen, durch diese Verfahren hergestellte Harze sowie die aufgrund dieser Harze erzielten Erzeugnisse | |
| DE1016273B (de) | Verfahren zur Herstellung von Glycidylaethern mehrwertiger Phenole | |
| DE1770816A1 (de) | Verfahren zur Herstellung von flexiblen Phenolharzen | |
| EP0019151B1 (de) | Verwendung von Isobutyraldehyd-Phenol-Polykondensaten als Verlackungsmittel für basische Farbstoffe | |
| DE1595470A1 (de) | Verfahren zur Herstellung haertbarer Kunstharze | |
| EP0209020B1 (de) | Verfahren zur Herstellung von Phenolharzen | |
| DE1169666B (de) | Verfahren zur Herstellung von hoch-molekularen, unschmelzbaren und unloeslichen, in organischen Loesungsmitteln jedoch quell-baren Kondensationsprodukten | |
| DE720759C (de) | Verfahren zur Herstellung von Kunstharzen | |
| DE2648062A1 (de) | Polyhydroxiphenol und verfahren zu seiner herstellung | |
| DE2914315C2 (de) | Verfahren zur Herstellung von Phenol-Formaldehyd-Harzen vom Resoltyp | |
| DE2001103B2 (de) | Verfahren zur Herstellung von Überzügen aus Phenolharzmassen | |
| DE387836C (de) | Verfahren zur Darstellung von Harzen | |
| DE3926118A1 (de) | Abietinsaeuederivate und ihre verwendung als emulgatoren | |
| DE2901405C2 (de) | Verfahren zur Herstellung von selbsthärtenden oder härtbaren Massen aus Destillationsrückständen der Kohlehydrierung | |
| DE2365654A1 (de) | Verfahren zur herstellung von modifizierten resolen aus gemischen, die phenole bzw. substituierte phenole und aralkylphenole enthalten, sowie ihre verwendung |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8131 | Rejection |