DE2330816C3 - Verfahren zur Herstellung von Dispersionen wärmehärtbarer Reaktionsprodukte und deren Verwendung - Google Patents
Verfahren zur Herstellung von Dispersionen wärmehärtbarer Reaktionsprodukte und deren VerwendungInfo
- Publication number
- DE2330816C3 DE2330816C3 DE2330816A DE2330816A DE2330816C3 DE 2330816 C3 DE2330816 C3 DE 2330816C3 DE 2330816 A DE2330816 A DE 2330816A DE 2330816 A DE2330816 A DE 2330816A DE 2330816 C3 DE2330816 C3 DE 2330816C3
- Authority
- DE
- Germany
- Prior art keywords
- phenol
- formaldehyde
- water
- styrene
- dispersions
- 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
- 239000006185 dispersion Substances 0.000 title claims description 26
- 238000000034 method Methods 0.000 title claims description 16
- 229920001187 thermosetting polymer Polymers 0.000 title claims description 9
- 239000007795 chemical reaction product Substances 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title claims description 8
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 82
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical class OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 48
- 150000002989 phenols Chemical class 0.000 claims description 33
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 30
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- 238000004519 manufacturing process Methods 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 235000006408 oxalic acid Nutrition 0.000 claims description 10
- 150000003440 styrenes Chemical class 0.000 claims description 10
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- 239000011230 binding agent Substances 0.000 claims description 4
- 239000004744 fabric Substances 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- 239000000084 colloidal system Substances 0.000 claims description 3
- 239000011521 glass Substances 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 229920000742 Cotton Polymers 0.000 claims description 2
- 229920001568 phenolic resin Polymers 0.000 description 17
- 239000000243 solution Substances 0.000 description 17
- 239000005011 phenolic resin Substances 0.000 description 9
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 8
- 239000000839 emulsion Substances 0.000 description 7
- -1 monohydroxybenzene compound Chemical class 0.000 description 7
- 238000012545 processing Methods 0.000 description 7
- 150000003335 secondary amines Chemical class 0.000 description 7
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- 229920002451 polyvinyl alcohol Polymers 0.000 description 4
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000004372 Polyvinyl alcohol Substances 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 3
- 239000000123 paper Substances 0.000 description 3
- 239000004014 plasticizer Substances 0.000 description 3
- 235000013824 polyphenols Nutrition 0.000 description 3
- 231100000331 toxic Toxicity 0.000 description 3
- 230000002588 toxic effect Effects 0.000 description 3
- NKTOLZVEWDHZMU-UHFFFAOYSA-N 2,5-xylenol Chemical compound CC1=CC=C(C)C(O)=C1 NKTOLZVEWDHZMU-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
- MPWGZBWDLMDIHO-UHFFFAOYSA-N 3-propylphenol Chemical compound CCCC1=CC=CC(O)=C1 MPWGZBWDLMDIHO-UHFFFAOYSA-N 0.000 description 2
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 2
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 2
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000006887 Ullmann reaction Methods 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 2
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 2
- RGIBXDHONMXTLI-UHFFFAOYSA-N chavicol Chemical compound OC1=CC=C(CC=C)C=C1 RGIBXDHONMXTLI-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
- 238000003912 environmental pollution Methods 0.000 description 2
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 2
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 2
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- GJYCVCVHRSWLNY-UHFFFAOYSA-N ortho-butylphenol Natural products CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 229920003987 resole Polymers 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
- DMAXMXPDVWTIRV-UHFFFAOYSA-N 2-(2-phenylethyl)phenol Chemical compound OC1=CC=CC=C1CCC1=CC=CC=C1 DMAXMXPDVWTIRV-UHFFFAOYSA-N 0.000 description 1
- QIRNGVVZBINFMX-UHFFFAOYSA-N 2-allylphenol Chemical compound OC1=CC=CC=C1CC=C QIRNGVVZBINFMX-UHFFFAOYSA-N 0.000 description 1
- WUQYBSRMWWRFQH-UHFFFAOYSA-N 2-prop-1-en-2-ylphenol Chemical compound CC(=C)C1=CC=CC=C1O WUQYBSRMWWRFQH-UHFFFAOYSA-N 0.000 description 1
- AIHZDRMFOVBNAV-UHFFFAOYSA-N 3-(2-phenylethyl)phenol Chemical compound OC1=CC=CC(CCC=2C=CC=CC=2)=C1 AIHZDRMFOVBNAV-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical class NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N 4-nonylphenol Chemical compound CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- ZSUQOKCTHXUQGC-UHFFFAOYSA-N 4-nonylphenol;oxirane Chemical compound C1CO1.CCCCCCCCCC1=CC=C(O)C=C1 ZSUQOKCTHXUQGC-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 239000003082 abrasive agent Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- UBXYXCRCOKCZIT-UHFFFAOYSA-N biphenyl-3-ol Chemical compound OC1=CC=CC(C=2C=CC=CC=2)=C1 UBXYXCRCOKCZIT-UHFFFAOYSA-N 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
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011093 chipboard Substances 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 235000013325 dietary fiber Nutrition 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 239000004312 hexamethylene tetramine Substances 0.000 description 1
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 239000011490 mineral wool Substances 0.000 description 1
- 239000012778 molding material Substances 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- FATBGEAMYMYZAF-KTKRTIGZSA-N oleamide Chemical compound CCCCCCCC\C=C/CCCCCCCC(N)=O FATBGEAMYMYZAF-KTKRTIGZSA-N 0.000 description 1
- 229940113162 oleylamide Drugs 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 125000001477 organic nitrogen group Chemical group 0.000 description 1
- 235000010292 orthophenyl phenol Nutrition 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000011120 plywood Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000011265 semifinished product Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
- C07C37/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms by addition reactions, i.e. reactions involving at least one carbon-to-carbon unsaturated bond
-
- 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
-
- 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
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
- D06M13/152—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen having a hydroxy group bound to a carbon atom of a six-membered aromatic ring
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
- D21H17/20—Macromolecular organic compounds
- D21H17/33—Synthetic macromolecular compounds
- D21H17/46—Synthetic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D21H17/47—Condensation polymers of aldehydes or ketones
- D21H17/48—Condensation polymers of aldehydes or ketones with phenols
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Phenolic Resins Or Amino Resins (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Paints Or Removers (AREA)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH919772A CH569681A5 (en:Method) | 1972-06-19 | 1972-06-19 | |
| CH918772 | 1972-06-19 | ||
| CH934572A CH573450A5 (en) | 1972-06-21 | 1972-06-21 | Phenol formaldehyde aqs dispersions - storage stable and water soluble |
| CH934472A CH579602A5 (en:Method) | 1972-06-21 | 1972-06-21 | |
| CH1367572 | 1972-09-19 | ||
| CH1367472 | 1972-09-19 | ||
| CH679673A CH587790A5 (en:Method) | 1972-06-19 | 1973-05-14 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2330816A1 DE2330816A1 (de) | 1974-01-17 |
| DE2330816B2 DE2330816B2 (de) | 1978-07-27 |
| DE2330816C3 true DE2330816C3 (de) | 1979-03-29 |
Family
ID=27561124
Family Applications (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2330850A Withdrawn DE2330850B2 (de) | 1972-06-19 | 1973-06-16 | Verfahren zur Herstellung von Lösungen von Monoaralkylphenolen in Phenol oder substituiertem Phenol bzw. deren Gemischen und deren Verwendung zur Herstellung von Resolharzen |
| DE2330816A Expired DE2330816C3 (de) | 1972-06-19 | 1973-06-16 | Verfahren zur Herstellung von Dispersionen wärmehärtbarer Reaktionsprodukte und deren Verwendung |
| DE19732330851 Ceased DE2330851B2 (de) | 1972-06-19 | 1973-06-16 | Verfahren zur herstellung von resolen und deren verwendung |
| DE2330815A Pending DE2330815A1 (de) | 1972-06-19 | 1973-06-16 | Verfahren zur herstellung von dispersionen waermehaertbarer reaktionsprodukte |
| DE2330849A Pending DE2330849A1 (de) | 1972-06-19 | 1973-06-16 | Verfahren zur herstellung von dispersionen waermehaertbarer reaktionsprodukte |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2330850A Withdrawn DE2330850B2 (de) | 1972-06-19 | 1973-06-16 | Verfahren zur Herstellung von Lösungen von Monoaralkylphenolen in Phenol oder substituiertem Phenol bzw. deren Gemischen und deren Verwendung zur Herstellung von Resolharzen |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732330851 Ceased DE2330851B2 (de) | 1972-06-19 | 1973-06-16 | Verfahren zur herstellung von resolen und deren verwendung |
| DE2330815A Pending DE2330815A1 (de) | 1972-06-19 | 1973-06-16 | Verfahren zur herstellung von dispersionen waermehaertbarer reaktionsprodukte |
| DE2330849A Pending DE2330849A1 (de) | 1972-06-19 | 1973-06-16 | Verfahren zur herstellung von dispersionen waermehaertbarer reaktionsprodukte |
Country Status (9)
| Country | Link |
|---|---|
| US (3) | US3875089A (en:Method) |
| AT (2) | AT329870B (en:Method) |
| BE (4) | BE801118A (en:Method) |
| CA (2) | CA1013086A (en:Method) |
| CH (1) | CH569681A5 (en:Method) |
| DE (5) | DE2330850B2 (en:Method) |
| FR (4) | FR2189457B1 (en:Method) |
| GB (4) | GB1422883A (en:Method) |
| NL (3) | NL7308486A (en:Method) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4038318A (en) * | 1975-06-27 | 1977-07-26 | Nalco Chemical Company | Ionenes |
| BE831953A (fr) * | 1975-07-31 | 1976-02-02 | Acec | Procede de mesure de la position des barres de reglage d'un reacteur nucleaire |
| MX144451A (es) * | 1976-03-30 | 1981-10-16 | Union Carbide Corp | Procedimiento mejorado para la obtencion de un resol solido en particulas |
| US4206095A (en) * | 1977-03-14 | 1980-06-03 | Union Carbide Corporation | Process for producing particulate resoles from aqueous dispersion |
| DE2753418C3 (de) * | 1977-05-14 | 1981-10-01 | Matsushita Electric Works Ltd., Kadoma, Osaka | Verfahren zur Herstellung von flammbeständigen Phenolharzen |
| DE2726105A1 (de) | 1977-06-10 | 1978-12-21 | Basf Ag | Nichtbrennbarer daemmstoff |
| US4196109A (en) * | 1978-08-17 | 1980-04-01 | Schenectady Chemicals, Inc. | Phenolic resin-triazine modifier for alkyd resins |
| DE2901462A1 (de) * | 1979-01-16 | 1980-07-31 | Hoechst Ag | Pigmentdispersionen und ihre verwendung |
| DE2901461A1 (de) * | 1979-01-16 | 1980-07-24 | Hoechst Ag | Verwendung oxalkylierter novolakharze als praeparationsmittel fuer dispersionsfarbstoffe und damit hergestellte zubereitungen |
| US4284512A (en) * | 1979-11-29 | 1981-08-18 | Commonwealth Scientific And Industrial Research Organization | Iron selective resins prepared from a phenol, HCHO and a di-secondary amine |
| US4308149A (en) * | 1980-07-14 | 1981-12-29 | Nalco Chemical Company | Branched/cross-linked cationic phenol-formaldehyde polymers useful in wastewater treatment |
| US4400229A (en) * | 1980-12-13 | 1983-08-23 | Ciba-Geigy Corporation | Process for the preparation of phenolic resin-containing dispersions and their use as adhesives |
| US4795506A (en) * | 1986-07-26 | 1989-01-03 | Detrex Corporation | Process for after-treatment of metals using 2,2-bis(4-hydroxyphenyl)alkyl poly derivatives |
| US4714752A (en) * | 1986-07-26 | 1987-12-22 | Detrex Corporation | 2,2-bis (4 hydroxyphenyl) alkyl poly derivatives for use in after-treatment of conversion coated metals |
| FR2638750B1 (fr) * | 1988-11-08 | 1992-06-05 | Ceca Sa | Procede pour l'obtention de dispersions aqueuses stables de resols phenoliques a basse teneur en formol |
| GB8830252D0 (en) * | 1988-12-24 | 1989-02-22 | Hepworth Minerals & Chemicals | Method of strengthening paper |
| EP0419741B1 (en) * | 1989-09-28 | 1995-11-29 | Indspec Chemical Corporation | Rubber compounding resin |
| US5290843A (en) * | 1993-04-29 | 1994-03-01 | Georgia-Pacific Resins, Inc. | Phenolic resins for reinforced composites |
| DE59510390D1 (de) * | 1994-06-30 | 2002-10-31 | Solutia Germany Gmbh & Co Kg | Alkylierte und aralkylierte Polyhydroxyaromaten und ein Verfahren zu ihrer Herstellung |
| US20070191572A1 (en) * | 2006-02-14 | 2007-08-16 | Tustin Gerald C | Resol beads, methods of making them, and methods of using them |
| US20070191571A1 (en) * | 2006-02-14 | 2007-08-16 | Sink Chester W | Resol beads, methods of making them, and methods of using them |
| US20070207917A1 (en) * | 2006-02-14 | 2007-09-06 | Chester Wayne Sink | Activated carbon monoliths and methods of making them |
| US8247072B2 (en) * | 2006-02-14 | 2012-08-21 | Eastman Chemical Company | Resol beads, methods of making them and methods of using them |
| TR201011146A2 (tr) * | 2010-12-30 | 2012-07-23 | Çukurova Ki̇mya Endüstri̇si̇ Anoni̇m Şi̇rketi̇ | Değişiklik yapılmış fenolik rezol reçine. |
| CN108611189B (zh) * | 2016-12-09 | 2023-02-21 | 丰益(上海)生物技术研发中心有限公司 | 一种控制油脂中双酚a和烷基酚的精炼工艺 |
| CN109422857A (zh) * | 2017-08-30 | 2019-03-05 | 北京彤程创展科技有限公司 | 一种改性双酚酚醛树脂、其制备方法及应用 |
| CN109749139B (zh) * | 2017-11-03 | 2022-05-10 | 北京彤程创展科技有限公司 | 一种工程胎胎面用橡胶组合物及应用 |
| JPWO2024095521A1 (en:Method) * | 2022-11-01 | 2024-05-10 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1807545A (en) * | 1927-04-06 | 1931-05-26 | Pollopas Ltd | Process of making phenol aldehyde condensation products |
| US2245245A (en) * | 1938-04-29 | 1941-06-10 | Gen Electric | Liquid coating composition and process of making same |
| US2443893A (en) * | 1944-06-08 | 1948-06-22 | Shawinigan Chem Ltd | Process for making stable emulsions of resinous materials |
| US2482525A (en) * | 1945-10-19 | 1949-09-20 | Westinghouse Electric Corp | Odorless phenol-formaldehyde resinous products |
| US2675335A (en) * | 1948-05-22 | 1954-04-13 | Union Carbide & Carbon Corp | Thermosetting laminating composition from formaldehyde condensed with mixture of phenol, monobutyl phenol, and dibutyl phenol |
| US2736718A (en) * | 1952-08-02 | 1956-02-28 | Norton Co | Phenolic resin products and their production |
| BE541693A (en:Method) * | 1954-10-04 | 1900-01-01 | ||
| US3351612A (en) * | 1962-10-01 | 1967-11-07 | Monsanto Co | Condensation products of phenol, polycyclic phenols and formaldehyde |
| DE1447961C3 (de) * | 1965-11-09 | 1975-07-03 | Hoechst Ag, 6000 Frankfurt | Lackemulsion zur Nachbehandlung entwickelter Flachdruckformen |
| GB1187307A (en) * | 1967-06-08 | 1970-04-08 | Sterling Moulding Materials Lt | Improvements in or relating to Phenolic Resin Compositions |
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| US3761448A (en) * | 1971-03-09 | 1973-09-25 | Monsanto Co | Resin oil modified resoles |
| US3697482A (en) * | 1971-04-07 | 1972-10-10 | Jerry H Hunsucker | Heat curable resins prepared from phenol,formaldehyde,dimethylolpropionic acid and an alkanolamine |
| US3719616A (en) * | 1971-05-13 | 1973-03-06 | Monsanto Co | Anti-migratory additive for emulsified phenolic resin systems said additive being a water soluble polyacrylate |
-
1972
- 1972-06-19 CH CH919772A patent/CH569681A5/xx not_active IP Right Cessation
-
1973
- 1973-06-15 CA CA174,117A patent/CA1013086A/en not_active Expired
- 1973-06-15 CA CA174,121A patent/CA1010172A/en not_active Expired
- 1973-06-16 DE DE2330850A patent/DE2330850B2/de not_active Withdrawn
- 1973-06-16 DE DE2330816A patent/DE2330816C3/de not_active Expired
- 1973-06-16 DE DE19732330851 patent/DE2330851B2/de not_active Ceased
- 1973-06-16 DE DE2330815A patent/DE2330815A1/de active Pending
- 1973-06-16 DE DE2330849A patent/DE2330849A1/de active Pending
- 1973-06-18 US US370771A patent/US3875089A/en not_active Expired - Lifetime
- 1973-06-18 AT AT532073A patent/AT329870B/de not_active IP Right Cessation
- 1973-06-18 AT AT535273A patent/AT329872B/de active
- 1973-06-18 US US370962A patent/US3870670A/en not_active Expired - Lifetime
- 1973-06-18 US US370768A patent/US3878136A/en not_active Expired - Lifetime
- 1973-06-19 BE BE132435A patent/BE801118A/xx unknown
- 1973-06-19 NL NL7308486A patent/NL7308486A/xx unknown
- 1973-06-19 NL NL7308484A patent/NL7308484A/xx unknown
- 1973-06-19 FR FR7323582A patent/FR2189457B1/fr not_active Expired
- 1973-06-19 GB GB2902173A patent/GB1422883A/en not_active Expired
- 1973-06-19 FR FR7323581A patent/FR2189357B1/fr not_active Expired
- 1973-06-19 FR FR7323580A patent/FR2219199B1/fr not_active Expired
- 1973-06-19 GB GB2902073A patent/GB1422410A/en not_active Expired
- 1973-06-19 GB GB2901873A patent/GB1423446A/en not_active Expired
- 1973-06-19 FR FR7323583A patent/FR2189458B1/fr not_active Expired
- 1973-06-19 BE BE132436A patent/BE801119A/xx unknown
- 1973-06-19 NL NL7308489A patent/NL7308489A/xx unknown
- 1973-06-19 BE BE132433A patent/BE801116A/xx unknown
- 1973-06-19 BE BE132437A patent/BE801120A/xx unknown
- 1973-06-19 GB GB2902273A patent/GB1406944A/en not_active Expired
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