DE2330815A1 - Verfahren zur herstellung von dispersionen waermehaertbarer reaktionsprodukte - Google Patents
Verfahren zur herstellung von dispersionen waermehaertbarer reaktionsprodukteInfo
- Publication number
- DE2330815A1 DE2330815A1 DE2330815A DE2330815A DE2330815A1 DE 2330815 A1 DE2330815 A1 DE 2330815A1 DE 2330815 A DE2330815 A DE 2330815A DE 2330815 A DE2330815 A DE 2330815A DE 2330815 A1 DE2330815 A1 DE 2330815A1
- Authority
- DE
- Germany
- Prior art keywords
- formaldehyde
- phenol
- phenols
- weight
- water
- 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
- 239000006185 dispersion Substances 0.000 title claims description 58
- 238000000034 method Methods 0.000 title claims description 33
- 239000007795 chemical reaction product Substances 0.000 title claims description 13
- 238000002360 preparation method Methods 0.000 title description 8
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 193
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 90
- 150000002989 phenols Chemical class 0.000 claims description 78
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 51
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 45
- 239000000203 mixture Substances 0.000 claims description 41
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 40
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 32
- 229920001568 phenolic resin Polymers 0.000 claims description 32
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 30
- 239000004372 Polyvinyl alcohol Substances 0.000 claims description 28
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 27
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 26
- 239000005011 phenolic resin Substances 0.000 claims description 25
- 229910017464 nitrogen compound Inorganic materials 0.000 claims description 22
- 150000002830 nitrogen compounds Chemical class 0.000 claims description 22
- 238000004519 manufacturing process Methods 0.000 claims description 20
- 238000003756 stirring Methods 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 239000000123 paper Substances 0.000 claims description 19
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 claims description 17
- 239000012043 crude product Substances 0.000 claims description 17
- 239000004354 Hydroxyethyl cellulose Substances 0.000 claims description 16
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 claims description 16
- -1 aliphatic radical Chemical class 0.000 claims description 16
- 239000003995 emulsifying agent Substances 0.000 claims description 16
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 claims description 16
- 229910021529 ammonia Inorganic materials 0.000 claims description 14
- 239000000126 substance Substances 0.000 claims description 14
- 150000003141 primary amines Chemical class 0.000 claims description 11
- 150000003335 secondary amines Chemical class 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 229920001187 thermosetting polymer Polymers 0.000 claims description 10
- 235000006408 oxalic acid Nutrition 0.000 claims description 9
- 150000003440 styrenes Chemical class 0.000 claims description 9
- 239000011230 binding agent Substances 0.000 claims description 8
- 239000000047 product Substances 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 239000004744 fabric Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 239000000084 colloidal system Substances 0.000 claims description 5
- 239000012875 nonionic emulsifier Substances 0.000 claims description 5
- 239000003921 oil Substances 0.000 claims description 5
- 230000001681 protective effect Effects 0.000 claims description 5
- HMNKTRSOROOSPP-UHFFFAOYSA-N 3-Ethylphenol Chemical compound CCC1=CC=CC(O)=C1 HMNKTRSOROOSPP-UHFFFAOYSA-N 0.000 claims description 4
- MPWGZBWDLMDIHO-UHFFFAOYSA-N 3-propylphenol Chemical compound CCCC1=CC=CC(O)=C1 MPWGZBWDLMDIHO-UHFFFAOYSA-N 0.000 claims description 4
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 claims description 4
- RGIBXDHONMXTLI-UHFFFAOYSA-N chavicol Chemical compound OC1=CC=C(CC=C)C=C1 RGIBXDHONMXTLI-UHFFFAOYSA-N 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 claims description 4
- 239000002023 wood Substances 0.000 claims description 4
- 150000001555 benzenes Chemical group 0.000 claims description 3
- 239000011521 glass Substances 0.000 claims description 3
- 239000000376 reactant Substances 0.000 claims description 3
- QIRNGVVZBINFMX-UHFFFAOYSA-N 2-allylphenol Chemical compound OC1=CC=CC=C1CC=C QIRNGVVZBINFMX-UHFFFAOYSA-N 0.000 claims description 2
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical class NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 claims description 2
- 229920000742 Cotton Polymers 0.000 claims description 2
- 239000003082 abrasive agent Substances 0.000 claims description 2
- 150000001336 alkenes Chemical class 0.000 claims description 2
- 230000029936 alkylation Effects 0.000 claims description 2
- 238000005804 alkylation reaction Methods 0.000 claims description 2
- YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical compound C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 claims description 2
- 239000004922 lacquer Substances 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- 239000011490 mineral wool Substances 0.000 claims description 2
- 235000010292 orthophenyl phenol Nutrition 0.000 claims description 2
- 239000011120 plywood Substances 0.000 claims description 2
- 238000000746 purification Methods 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- WUQYBSRMWWRFQH-UHFFFAOYSA-N 2-prop-1-en-2-ylphenol Chemical compound CC(=C)C1=CC=CC=C1O WUQYBSRMWWRFQH-UHFFFAOYSA-N 0.000 claims 1
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 claims 1
- 239000011093 chipboard Substances 0.000 claims 1
- 239000011248 coating agent Substances 0.000 claims 1
- 238000000227 grinding Methods 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000007769 metal material Substances 0.000 claims 1
- 239000012778 molding material Substances 0.000 claims 1
- 239000000243 solution Substances 0.000 description 30
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 24
- 229920005989 resin Polymers 0.000 description 17
- 239000011347 resin Substances 0.000 description 17
- IGFHQQFPSIBGKE-UHFFFAOYSA-N 4-nonylphenol Chemical compound CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 12
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 12
- 239000000839 emulsion Substances 0.000 description 10
- 239000008367 deionised water Substances 0.000 description 7
- 229910021641 deionized water Inorganic materials 0.000 description 7
- 239000008098 formaldehyde solution Substances 0.000 description 7
- 238000012545 processing Methods 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 5
- 150000001299 aldehydes Chemical class 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 230000008901 benefit Effects 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
- 235000011114 ammonium hydroxide Nutrition 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000005260 corrosion Methods 0.000 description 4
- 230000007797 corrosion Effects 0.000 description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 4
- 239000004014 plasticizer Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 238000003912 environmental pollution Methods 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 229920003987 resole Polymers 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
- DMAXMXPDVWTIRV-UHFFFAOYSA-N 2-(2-phenylethyl)phenol Chemical compound OC1=CC=CC=C1CCC1=CC=CC=C1 DMAXMXPDVWTIRV-UHFFFAOYSA-N 0.000 description 2
- 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 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000006887 Ullmann reaction Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 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
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 238000005470 impregnation Methods 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
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- 238000002203 pretreatment Methods 0.000 description 2
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- WHGXZPQWZJUGEP-UHFFFAOYSA-N 2-prop-1-enylphenol Chemical compound CC=CC1=CC=CC=C1O WHGXZPQWZJUGEP-UHFFFAOYSA-N 0.000 description 1
- MQSXUKPGWMJYBT-UHFFFAOYSA-N 3-butylphenol Chemical compound CCCCC1=CC=CC(O)=C1 MQSXUKPGWMJYBT-UHFFFAOYSA-N 0.000 description 1
- WJPFLNFZBVCBPB-UHFFFAOYSA-N 3-methyl-2-(2-phenylethyl)phenol Chemical compound CC1=CC=CC(O)=C1CCC1=CC=CC=C1 WJPFLNFZBVCBPB-UHFFFAOYSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- BTXXTMOWISPQSJ-UHFFFAOYSA-N 4,4,4-trifluorobutan-2-one Chemical compound CC(=O)CC(F)(F)F BTXXTMOWISPQSJ-UHFFFAOYSA-N 0.000 description 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
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- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
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- 239000004094 surface-active agent Substances 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- 239000002383 tung oil Substances 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
- 239000008096 xylene Substances 0.000 description 1
- 239000004246 zinc acetate 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 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 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 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-06-21 | 1972-06-21 | |
| CH1367472 | 1972-09-19 | ||
| CH1367572 | 1972-09-19 | ||
| CH679673A CH587790A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-06-19 | 1973-05-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2330815A1 true DE2330815A1 (de) | 1974-01-17 |
Family
ID=27561124
Family Applications (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2330815A Pending DE2330815A1 (de) | 1972-06-19 | 1973-06-16 | Verfahren zur herstellung von dispersionen waermehaertbarer reaktionsprodukte |
| DE19732330851 Ceased DE2330851B2 (de) | 1972-06-19 | 1973-06-16 | Verfahren zur herstellung von resolen und deren verwendung |
| DE2330816A Expired DE2330816C3 (de) | 1972-06-19 | 1973-06-16 | Verfahren zur Herstellung von Dispersionen wärmehärtbarer Reaktionsprodukte und deren Verwendung |
| DE2330849A Pending DE2330849A1 (de) | 1972-06-19 | 1973-06-16 | Verfahren zur herstellung von dispersionen waermehaertbarer reaktionsprodukte |
| 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 (4)
| 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 |
| DE2330816A Expired DE2330816C3 (de) | 1972-06-19 | 1973-06-16 | Verfahren zur Herstellung von Dispersionen wärmehärtbarer Reaktionsprodukte und deren Verwendung |
| DE2330849A Pending DE2330849A1 (de) | 1972-06-19 | 1973-06-16 | Verfahren zur herstellung von dispersionen waermehaertbarer reaktionsprodukte |
| 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 |
Country Status (9)
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 |
| 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 |
| 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 |
| 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 |
| ATE130860T1 (de) * | 1989-09-28 | 1995-12-15 | Indspec Chemical Corp | Zumischharz für gummi. |
| 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 |
| US20070207917A1 (en) * | 2006-02-14 | 2007-09-06 | Chester Wayne Sink | Activated carbon monoliths and methods of making them |
| US20070191571A1 (en) * | 2006-02-14 | 2007-08-16 | Sink Chester W | Resol beads, methods of making them, and methods of using 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 |
| KR20250099439A (ko) * | 2022-11-01 | 2025-07-01 | 혼슈우 카가쿠고교 가부시키가이샤 | 경화성 조성물 |
Family Cites Families (14)
| 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 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 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 |
| US3703494A (en) * | 1971-03-01 | 1972-11-21 | Monsanto Co | Resole varnishes wherein phenol is alkylated with a dicyclopentadiene-containing mixture and then condensed with formaldehyde to produce the resole |
| 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 CA174,121A patent/CA1010172A/en not_active Expired
- 1973-06-15 CA CA174,117A patent/CA1013086A/en not_active Expired
- 1973-06-16 DE DE2330815A patent/DE2330815A1/de active Pending
- 1973-06-16 DE DE19732330851 patent/DE2330851B2/de not_active Ceased
- 1973-06-16 DE DE2330816A patent/DE2330816C3/de not_active Expired
- 1973-06-16 DE DE2330849A patent/DE2330849A1/de active Pending
- 1973-06-16 DE DE2330850A patent/DE2330850B2/de not_active Withdrawn
- 1973-06-18 AT AT535273A patent/AT329872B/de active
- 1973-06-18 AT AT532073A patent/AT329870B/de not_active IP Right Cessation
- 1973-06-18 US US370771A patent/US3875089A/en not_active Expired - Lifetime
- 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 GB GB2902273A patent/GB1406944A/en not_active Expired
- 1973-06-19 BE BE132435A patent/BE801118A/xx unknown
- 1973-06-19 FR FR7323580A patent/FR2219199B1/fr not_active Expired
- 1973-06-19 GB GB2902173A patent/GB1422883A/en not_active Expired
- 1973-06-19 BE BE132437A patent/BE801120A/xx unknown
- 1973-06-19 BE BE132433A patent/BE801116A/xx unknown
- 1973-06-19 NL NL7308484A patent/NL7308484A/xx unknown
- 1973-06-19 BE BE132436A patent/BE801119A/xx unknown
- 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 FR7323582A patent/FR2189457B1/fr not_active Expired
- 1973-06-19 NL NL7308486A patent/NL7308486A/xx unknown
- 1973-06-19 FR FR7323581A patent/FR2189357B1/fr not_active Expired
- 1973-06-19 NL NL7308489A patent/NL7308489A/xx unknown
- 1973-06-19 FR FR7323583A patent/FR2189458B1/fr not_active Expired
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHN | Withdrawal |