DE2713852C3 - Verfahren zur Herstellung eines fein zerteilten, festen, wärmereaktionsfähigen, praktisch wasserunlöslichen Resols - Google Patents
Verfahren zur Herstellung eines fein zerteilten, festen, wärmereaktionsfähigen, praktisch wasserunlöslichen ResolsInfo
- Publication number
- DE2713852C3 DE2713852C3 DE2713852A DE2713852A DE2713852C3 DE 2713852 C3 DE2713852 C3 DE 2713852C3 DE 2713852 A DE2713852 A DE 2713852A DE 2713852 A DE2713852 A DE 2713852A DE 2713852 C3 DE2713852 C3 DE 2713852C3
- Authority
- DE
- Germany
- Prior art keywords
- phenol
- water
- finely divided
- resin
- hexamethylenetetramine
- 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
- 229920003987 resole Polymers 0.000 title claims description 73
- 238000000034 method Methods 0.000 title claims description 45
- 239000007787 solid Substances 0.000 title claims description 31
- 230000008569 process Effects 0.000 title claims description 29
- 238000004519 manufacturing process Methods 0.000 title claims description 25
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 claims description 103
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 87
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 60
- 235000010299 hexamethylene tetramine Nutrition 0.000 claims description 51
- 239000004312 hexamethylene tetramine Substances 0.000 claims description 51
- 230000001681 protective effect Effects 0.000 claims description 51
- 239000000084 colloidal system Substances 0.000 claims description 44
- 239000006185 dispersion Substances 0.000 claims description 36
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 31
- -1 amine compound Chemical class 0.000 claims description 18
- 229910021529 ammonia Inorganic materials 0.000 claims description 15
- 239000011541 reaction mixture Substances 0.000 claims description 11
- 239000012736 aqueous medium Substances 0.000 claims description 10
- 229920001187 thermosetting polymer Polymers 0.000 claims description 9
- 230000015572 biosynthetic process Effects 0.000 claims description 8
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 4
- 230000006641 stabilisation Effects 0.000 claims description 4
- 238000011105 stabilization Methods 0.000 claims description 4
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 112
- 229920005989 resin Polymers 0.000 description 73
- 239000011347 resin Substances 0.000 description 73
- 239000000203 mixture Substances 0.000 description 52
- 229960004011 methenamine Drugs 0.000 description 50
- 239000000047 product Substances 0.000 description 49
- 238000006243 chemical reaction Methods 0.000 description 45
- 239000000499 gel Substances 0.000 description 37
- 238000012360 testing method Methods 0.000 description 37
- 235000019256 formaldehyde Nutrition 0.000 description 30
- 238000009472 formulation Methods 0.000 description 30
- 239000005011 phenolic resin Substances 0.000 description 28
- 229920001568 phenolic resin Polymers 0.000 description 27
- 239000002245 particle Substances 0.000 description 26
- 244000215068 Acacia senegal Species 0.000 description 24
- 229920000084 Gum arabic Polymers 0.000 description 24
- 239000000205 acacia gum Substances 0.000 description 24
- 235000010489 acacia gum Nutrition 0.000 description 24
- 239000000463 material Substances 0.000 description 24
- 238000005245 sintering Methods 0.000 description 24
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 239000008098 formaldehyde solution Substances 0.000 description 21
- 238000002474 experimental method Methods 0.000 description 20
- 229920002451 polyvinyl alcohol Polymers 0.000 description 19
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 19
- 239000000843 powder Substances 0.000 description 19
- 238000013459 approach Methods 0.000 description 16
- 239000004372 Polyvinyl alcohol Substances 0.000 description 15
- 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 15
- 238000009833 condensation Methods 0.000 description 15
- 230000005494 condensation Effects 0.000 description 15
- 238000001035 drying Methods 0.000 description 15
- 238000001914 filtration Methods 0.000 description 15
- 238000001816 cooling Methods 0.000 description 14
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 14
- 239000000523 sample Substances 0.000 description 13
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 12
- 239000012071 phase Substances 0.000 description 11
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 10
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 9
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 8
- 238000001879 gelation Methods 0.000 description 8
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 229920002907 Guar gum Polymers 0.000 description 7
- 239000000420 anogeissus latifolia wall. gum Substances 0.000 description 7
- 239000000839 emulsion Substances 0.000 description 7
- 230000009477 glass transition Effects 0.000 description 7
- 239000000665 guar gum Substances 0.000 description 7
- 235000010417 guar gum Nutrition 0.000 description 7
- 229960002154 guar gum Drugs 0.000 description 7
- 235000019314 gum ghatti Nutrition 0.000 description 7
- 230000035484 reaction time Effects 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 229940106691 bisphenol a Drugs 0.000 description 6
- 238000009826 distribution Methods 0.000 description 6
- 239000003607 modifier Substances 0.000 description 6
- 150000002989 phenols Chemical class 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- 238000003860 storage Methods 0.000 description 6
- 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 5
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 5
- 229930003836 cresol Natural products 0.000 description 5
- 238000007865 diluting Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000010419 fine particle Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 229920001817 Agar Polymers 0.000 description 4
- 229920000877 Melamine resin Polymers 0.000 description 4
- 229920002472 Starch Polymers 0.000 description 4
- 239000008272 agar Substances 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 238000005119 centrifugation Methods 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 239000012530 fluid Substances 0.000 description 4
- 238000002955 isolation Methods 0.000 description 4
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 4
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 4
- 229920003986 novolac Polymers 0.000 description 4
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 4
- 239000006187 pill Substances 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000008107 starch Substances 0.000 description 4
- 235000019698 starch Nutrition 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 229930040373 Paraformaldehyde Natural products 0.000 description 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical class CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- 239000001768 carboxy methyl cellulose Substances 0.000 description 3
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 3
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000007859 condensation product Substances 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 239000012065 filter cake Substances 0.000 description 3
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 230000002209 hydrophobic effect Effects 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 229920002866 paraformaldehyde Polymers 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 229920001282 polysaccharide Polymers 0.000 description 3
- 239000005017 polysaccharide Substances 0.000 description 3
- 229920001296 polysiloxane Polymers 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- ICKWICRCANNIBI-UHFFFAOYSA-N 2,4-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C(C(C)(C)C)=C1 ICKWICRCANNIBI-UHFFFAOYSA-N 0.000 description 2
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 2
- WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-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
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 229920001807 Urea-formaldehyde Polymers 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000003973 alkyl amines Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 230000001427 coherent effect Effects 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 230000009969 flowable effect Effects 0.000 description 2
- 230000005484 gravity Effects 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- CKFGINPQOCXMAZ-UHFFFAOYSA-N methanediol Chemical compound OCO CKFGINPQOCXMAZ-UHFFFAOYSA-N 0.000 description 2
- 229910017464 nitrogen compound Inorganic materials 0.000 description 2
- 150000002830 nitrogen compounds Chemical class 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 230000020477 pH reduction Effects 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 235000018102 proteins Nutrition 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
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- 239000012265 solid product Substances 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- 239000008399 tap water Substances 0.000 description 2
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- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- DKCPKDPYUFEZCP-UHFFFAOYSA-N 2,6-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1O DKCPKDPYUFEZCP-UHFFFAOYSA-N 0.000 description 1
- CMLFRMDBDNHMRA-UHFFFAOYSA-N 2h-1,2-benzoxazine Chemical compound C1=CC=C2C=CNOC2=C1 CMLFRMDBDNHMRA-UHFFFAOYSA-N 0.000 description 1
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
- UFTHEDBYLPFRDP-UHFFFAOYSA-N 5,6-dihydro-2h-oxazine Chemical compound C1CC=CNO1 UFTHEDBYLPFRDP-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 241001474374 Blennius Species 0.000 description 1
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- 244000007835 Cyamopsis tetragonoloba Species 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
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- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
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- 125000000217 alkyl group Chemical group 0.000 description 1
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- 150000004982 aromatic amines Chemical class 0.000 description 1
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- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
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- PCHPORCSPXIHLZ-UHFFFAOYSA-N diphenhydramine hydrochloride Chemical compound [Cl-].C=1C=CC=CC=1C(OCC[NH+](C)C)C1=CC=CC=C1 PCHPORCSPXIHLZ-UHFFFAOYSA-N 0.000 description 1
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- MXHTZQSKTCCMFG-UHFFFAOYSA-N n,n-dibenzyl-1-phenylmethanamine Chemical compound C=1C=CC=CC=1CN(CC=1C=CC=CC=1)CC1=CC=CC=C1 MXHTZQSKTCCMFG-UHFFFAOYSA-N 0.000 description 1
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- 229910000069 nitrogen hydride Inorganic materials 0.000 description 1
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- 238000010298 pulverizing process Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000012925 reference material Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000004043 responsiveness Effects 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 238000009666 routine test Methods 0.000 description 1
- 238000010079 rubber tapping Methods 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000012798 spherical particle Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 238000010626 work up procedure Methods 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
-
- 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
- C08G14/00—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00
- C08G14/02—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes
- C08G14/04—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes with phenols
- C08G14/06—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes with phenols and monomers containing hydrogen attached to nitrogen
-
- 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
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)
- Processes Of Treating Macromolecular Substances (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US67207576A | 1976-03-30 | 1976-03-30 | |
| US77688177A | 1977-03-14 | 1977-03-14 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2713852A1 DE2713852A1 (de) | 1977-10-06 |
| DE2713852B2 DE2713852B2 (de) | 1980-06-26 |
| DE2713852C3 true DE2713852C3 (de) | 1981-02-26 |
Family
ID=27100682
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2713852A Expired DE2713852C3 (de) | 1976-03-30 | 1977-03-29 | Verfahren zur Herstellung eines fein zerteilten, festen, wärmereaktionsfähigen, praktisch wasserunlöslichen Resols |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS52141893A (enrdf_load_stackoverflow) |
| AU (1) | AU518241B2 (enrdf_load_stackoverflow) |
| DE (1) | DE2713852C3 (enrdf_load_stackoverflow) |
| ES (1) | ES457291A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2346383A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1575366A (enrdf_load_stackoverflow) |
| IT (1) | IT1075684B (enrdf_load_stackoverflow) |
| MX (1) | MX144451A (enrdf_load_stackoverflow) |
| SE (1) | SE7703628L (enrdf_load_stackoverflow) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5324390A (en) * | 1976-08-19 | 1978-03-07 | Lignyte Co Ltd | Continuous preparation method of phenol resin composition |
| US4182696A (en) * | 1977-12-14 | 1980-01-08 | Union Carbide Corporation | Process for producing particulate filler-containing resole molding compositions from aqueous dispersion |
| CA1187232A (en) * | 1980-04-17 | 1985-05-14 | John R. Blickensderfer | Phenolic friction particles |
| US4316827A (en) * | 1980-04-17 | 1982-02-23 | Union Carbide Corporation | Rubber modified phenolic friction particles |
| JPS5817114A (ja) * | 1981-07-24 | 1983-02-01 | Kanebo Ltd | 粒状ないし粉末状の含窒素フエノ−ル・アルデヒド系共重合樹脂及びその製造法 |
| JPS58142907A (ja) * | 1982-02-19 | 1983-08-25 | Kanebo Ltd | 粒状ないし粉末状の含窒素フエノ−ル・アルデヒド系共重合樹脂及びその製造法 |
| JPS58152045A (ja) * | 1982-03-05 | 1983-09-09 | Kanebo Ltd | 熱硬化型の樹脂組成物 |
| JPH0228200U (enrdf_load_stackoverflow) * | 1988-08-12 | 1990-02-23 | ||
| US5728797A (en) * | 1995-08-18 | 1998-03-17 | International Paper | Method of making cured resin particles |
| EP0907674B1 (en) * | 1996-06-19 | 2000-08-30 | International Paper Company | Resin encapsulated particles |
| DE102016125624A1 (de) * | 2016-12-23 | 2018-06-28 | HÜTTENES-ALBERTUS Chemische Werke Gesellschaft mit beschränkter Haftung | Phenolharz zur Verwendung in der Phenolharzkomponente eines Zweikomponenten- Bindemittelsystems |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR868523A (fr) * | 1938-10-12 | 1942-01-05 | Dynamit Nobel Ag | Procédé de préparation de résines phénoliques |
| FR974588A (fr) * | 1941-11-04 | 1951-02-23 | Perfectionnements apportés au produits résineux artificiels et à leur obtention | |
| FR2098625A5 (enrdf_load_stackoverflow) * | 1970-07-22 | 1972-03-10 | Saint Gobain Pont A Mousson | |
| CH569681A5 (enrdf_load_stackoverflow) * | 1972-06-19 | 1975-11-28 | Hoechst Ag |
-
1977
- 1977-03-27 MX MX168545A patent/MX144451A/es unknown
- 1977-03-28 AU AU23692/77A patent/AU518241B2/en not_active Expired
- 1977-03-29 FR FR7709408A patent/FR2346383A1/fr active Granted
- 1977-03-29 IT IT21847/77A patent/IT1075684B/it active
- 1977-03-29 JP JP3405577A patent/JPS52141893A/ja active Granted
- 1977-03-29 SE SE7703628A patent/SE7703628L/ unknown
- 1977-03-29 GB GB13258/77A patent/GB1575366A/en not_active Expired
- 1977-03-29 DE DE2713852A patent/DE2713852C3/de not_active Expired
- 1977-03-29 ES ES457291A patent/ES457291A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| AU518241B2 (en) | 1981-09-24 |
| JPS52141893A (en) | 1977-11-26 |
| DE2713852B2 (de) | 1980-06-26 |
| SE7703628L (sv) | 1977-11-14 |
| DE2713852A1 (de) | 1977-10-06 |
| FR2346383A1 (fr) | 1977-10-28 |
| AU2369277A (en) | 1978-10-05 |
| GB1575366A (en) | 1980-09-17 |
| ES457291A1 (es) | 1978-02-16 |
| FR2346383B1 (enrdf_load_stackoverflow) | 1984-02-03 |
| JPS619967B2 (enrdf_load_stackoverflow) | 1986-03-27 |
| MX144451A (es) | 1981-10-16 |
| IT1075684B (it) | 1985-04-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: UNION CARBIDE CORP., 06817 DANBURY, CONN., US |
|
| 8339 | Ceased/non-payment of the annual fee |