GB1575366A - Process for producing particulate resoles from aqueous dispersion - Google Patents
Process for producing particulate resoles from aqueous dispersion Download PDFInfo
- Publication number
- GB1575366A GB1575366A GB13258/77A GB1325877A GB1575366A GB 1575366 A GB1575366 A GB 1575366A GB 13258/77 A GB13258/77 A GB 13258/77A GB 1325877 A GB1325877 A GB 1325877A GB 1575366 A GB1575366 A GB 1575366A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phenol
- resole
- water
- reaction
- particulate
- 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 94
- 238000000034 method Methods 0.000 title claims description 53
- 230000008569 process Effects 0.000 title claims description 44
- 239000006185 dispersion Substances 0.000 title claims description 38
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 145
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 100
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 59
- 239000000203 mixture Substances 0.000 claims description 44
- 238000006243 chemical reaction Methods 0.000 claims description 43
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 39
- 239000000084 colloidal system Substances 0.000 claims description 34
- 230000001681 protective effect Effects 0.000 claims description 31
- 239000007787 solid Substances 0.000 claims description 29
- 235000010489 acacia gum Nutrition 0.000 claims description 27
- 229920000084 Gum arabic Polymers 0.000 claims description 26
- 239000000205 acacia gum Substances 0.000 claims description 26
- 244000215068 Acacia senegal Species 0.000 claims description 25
- -1 amine compound Chemical class 0.000 claims description 23
- 239000002245 particle Substances 0.000 claims description 22
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 22
- 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 claims description 20
- 238000001816 cooling Methods 0.000 claims description 17
- 238000001035 drying Methods 0.000 claims description 17
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 claims description 17
- 229910021529 ammonia Inorganic materials 0.000 claims description 16
- 238000001914 filtration Methods 0.000 claims description 16
- 239000004372 Polyvinyl alcohol Substances 0.000 claims description 14
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 12
- 239000012736 aqueous medium Substances 0.000 claims description 11
- 239000011541 reaction mixture Substances 0.000 claims description 11
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 claims description 10
- 229920001187 thermosetting polymer Polymers 0.000 claims description 10
- 244000106483 Anogeissus latifolia Species 0.000 claims description 8
- 235000011514 Anogeissus latifolia Nutrition 0.000 claims description 8
- 239000001922 Gum ghatti Substances 0.000 claims description 8
- 235000019314 gum ghatti Nutrition 0.000 claims description 8
- 239000004312 hexamethylene tetramine Substances 0.000 claims description 8
- 235000010299 hexamethylene tetramine Nutrition 0.000 claims description 8
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 229920002907 Guar gum Polymers 0.000 claims description 6
- 238000007865 diluting Methods 0.000 claims description 6
- 239000000665 guar gum Substances 0.000 claims description 6
- 235000010417 guar gum Nutrition 0.000 claims description 6
- 229960002154 guar gum Drugs 0.000 claims description 6
- 150000002989 phenols Chemical class 0.000 claims description 6
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 claims description 5
- 238000013019 agitation Methods 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 claims description 3
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 3
- 239000000853 adhesive Substances 0.000 claims description 2
- 230000001070 adhesive effect Effects 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 239000002657 fibrous material Substances 0.000 claims 1
- 239000000706 filtrate Substances 0.000 claims 1
- 229920005989 resin Polymers 0.000 description 56
- 239000011347 resin Substances 0.000 description 56
- 239000000047 product Substances 0.000 description 50
- 239000000499 gel Substances 0.000 description 40
- 235000019256 formaldehyde Nutrition 0.000 description 30
- 229920001568 phenolic resin Polymers 0.000 description 29
- 239000005011 phenolic resin Substances 0.000 description 29
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 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
- 238000009472 formulation Methods 0.000 description 21
- 239000000843 powder Substances 0.000 description 21
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 18
- 238000012360 testing method Methods 0.000 description 18
- 238000002474 experimental method Methods 0.000 description 17
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 16
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 14
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 11
- 239000000463 material Substances 0.000 description 11
- 239000000523 sample Substances 0.000 description 11
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 10
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 10
- 238000009833 condensation Methods 0.000 description 10
- 230000005494 condensation Effects 0.000 description 10
- 238000005245 sintering Methods 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 9
- 239000012071 phase Substances 0.000 description 9
- 235000013824 polyphenols Nutrition 0.000 description 9
- 239000000376 reactant Substances 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 229940106691 bisphenol a Drugs 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 239000008346 aqueous phase Substances 0.000 description 6
- 238000012512 characterization method Methods 0.000 description 6
- 238000009826 distribution Methods 0.000 description 6
- 239000003607 modifier 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
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 5
- 241000282372 Panthera onca Species 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 5
- 229930003836 cresol Natural products 0.000 description 5
- 230000009477 glass transition Effects 0.000 description 5
- 229920002866 paraformaldehyde Polymers 0.000 description 5
- 239000006187 pill 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
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 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
- 238000004458 analytical method Methods 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 238000005119 centrifugation Methods 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 239000010419 fine particle Substances 0.000 description 4
- 238000001879 gelation Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 238000002955 isolation Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 4
- 229920003986 novolac Polymers 0.000 description 4
- 230000020477 pH reduction Effects 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000008107 starch Substances 0.000 description 4
- 235000019698 starch Nutrition 0.000 description 4
- 238000010626 work up procedure Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 3
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 3
- 229920000877 Melamine resin Polymers 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- IZZOKZMGQDMCAE-XQZFLANJSA-N alpha-L-Rhap-(1->2)-[beta-D-GlcpNAc-(1->3)]-alpha-L-Rhap-(1->3)-alpha-L-Rhap-(1->2)-[beta-D-GlcpNAc-(1->3)]-alpha-L-Rhap Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@@H]1[C@H](O[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](O)[C@H](C)O[C@H]1O[C@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H]([C@@H](O)[C@H](C)O[C@H]2O)O[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)NC(C)=O)O[C@@H](C)[C@@H]1O IZZOKZMGQDMCAE-XQZFLANJSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- 239000001768 carboxy methyl cellulose Substances 0.000 description 3
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000012065 filter cake Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 230000002209 hydrophobic effect Effects 0.000 description 3
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 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
- 238000001556 precipitation Methods 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 238000005406 washing Methods 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
- 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 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical compound CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-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
- 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
- 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
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical class CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- 229920002125 Sokalan® Polymers 0.000 description 2
- 238000005054 agglomeration Methods 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- 150000003973 alkyl amines Chemical class 0.000 description 2
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- 230000001427 coherent effect Effects 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 150000001896 cresols Chemical class 0.000 description 2
- 238000010908 decantation Methods 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 2
- 230000004927 fusion Effects 0.000 description 2
- 230000005484 gravity Effects 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- CKFGINPQOCXMAZ-UHFFFAOYSA-N methanediol Chemical compound OCO CKFGINPQOCXMAZ-UHFFFAOYSA-N 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 229910017464 nitrogen compound Inorganic materials 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 230000001737 promoting effect Effects 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000012925 reference material Substances 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000008399 tap water Substances 0.000 description 2
- 235000020679 tap water Nutrition 0.000 description 2
- 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
- KUFFULVDNCHOFZ-UHFFFAOYSA-N 2,4-xylenol Chemical compound CC1=CC=C(O)C(C)=C1 KUFFULVDNCHOFZ-UHFFFAOYSA-N 0.000 description 1
- XNHIYJUZXZOGBW-UHFFFAOYSA-N 3-benzyl-2H-1,2-benzoxazine Chemical compound C(C1=CC=CC=C1)C=1NOC2=C(C1)C=CC=C2 XNHIYJUZXZOGBW-UHFFFAOYSA-N 0.000 description 1
- KJWMCPYEODZESQ-UHFFFAOYSA-N 4-Dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC=C(O)C=C1 KJWMCPYEODZESQ-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
- IGFHQQFPSIBGKE-UHFFFAOYSA-N 4-nonylphenol Chemical compound CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- NTDQQZYCCIDJRK-UHFFFAOYSA-N 4-octylphenol Chemical compound CCCCCCCCC1=CC=C(O)C=C1 NTDQQZYCCIDJRK-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
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- 229920006384 Airco Polymers 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
- 229910001369 Brass Inorganic materials 0.000 description 1
- 244000303965 Cyamopsis psoralioides Species 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 239000004716 Ethylene/acrylic acid copolymer Substances 0.000 description 1
- 244000151282 Eucalyptus cambageana Species 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- ISWSIDIOOBJBQZ-QNKSCLMFSA-N Hexadeuterophenol Chemical compound [2H]OC1=C([2H])C([2H])=C([2H])C([2H])=C1[2H] ISWSIDIOOBJBQZ-QNKSCLMFSA-N 0.000 description 1
- 238000003109 Karl Fischer titration Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical group CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 239000001785 acacia senegal l. willd gum Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- WGQKYBSKWIADBV-UHFFFAOYSA-N aminomethyl benzene Natural products NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 230000003466 anti-cipated effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 229910001863 barium hydroxide Inorganic materials 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000003939 benzylamines Chemical class 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
- 239000010951 brass Substances 0.000 description 1
- STIAPHVBRDNOAJ-UHFFFAOYSA-N carbamimidoylazanium;carbonate Chemical compound NC(N)=N.NC(N)=N.OC(O)=O STIAPHVBRDNOAJ-UHFFFAOYSA-N 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- MMVILKIFGQPOLE-UHFFFAOYSA-N diazanium;carbonate;hydrate Chemical compound [NH4+].[NH4+].[OH-].OC([O-])=O MMVILKIFGQPOLE-UHFFFAOYSA-N 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- 239000012470 diluted sample Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- QHZOMAXECYYXGP-UHFFFAOYSA-N ethene;prop-2-enoic acid Chemical compound C=C.OC(=O)C=C QHZOMAXECYYXGP-UHFFFAOYSA-N 0.000 description 1
- 229920006226 ethylene-acrylic acid Polymers 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229920013818 hydroxypropyl guar gum Polymers 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 239000011872 intimate mixture Substances 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229940100630 metacresol Drugs 0.000 description 1
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical class [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 1
- VHWYCFISAQVCCP-UHFFFAOYSA-N methoxymethanol Chemical compound COCO VHWYCFISAQVCCP-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 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
- ZLDHYRXZZNDOKU-UHFFFAOYSA-N n,n-diethyl-3-trimethoxysilylpropan-1-amine Chemical compound CCN(CC)CCC[Si](OC)(OC)OC ZLDHYRXZZNDOKU-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 125000005704 oxymethylene group Chemical group [H]C([H])([*:2])O[*:1] 0.000 description 1
- QBDSZLJBMIMQRS-UHFFFAOYSA-N p-Cumylphenol Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=CC=C1 QBDSZLJBMIMQRS-UHFFFAOYSA-N 0.000 description 1
- NKTOLZVEWDHZMU-UHFFFAOYSA-N p-cumyl phenol Natural products CC1=CC=C(C)C(O)=C1 NKTOLZVEWDHZMU-UHFFFAOYSA-N 0.000 description 1
- FTDXCHCAMNRNNY-UHFFFAOYSA-N phenol Chemical compound OC1=CC=CC=C1.OC1=CC=CC=C1 FTDXCHCAMNRNNY-UHFFFAOYSA-N 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 238000010079 rubber tapping Methods 0.000 description 1
- CQRYARSYNCAZFO-UHFFFAOYSA-N salicyl alcohol Chemical class OCC1=CC=CC=C1O CQRYARSYNCAZFO-UHFFFAOYSA-N 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 238000013341 scale-up Methods 0.000 description 1
- 238000007560 sedimentation technique Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- FVEFRICMTUKAML-UHFFFAOYSA-M sodium tetradecyl sulfate Chemical compound [Na+].CCCCC(CC)CCC(CC(C)C)OS([O-])(=O)=O FVEFRICMTUKAML-UHFFFAOYSA-M 0.000 description 1
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000002023 wood 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
- 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 (1)
| Publication Number | Publication Date |
|---|---|
| GB1575366A true GB1575366A (en) | 1980-09-17 |
Family
ID=27100682
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB13258/77A Expired GB1575366A (en) | 1976-03-30 | 1977-03-29 | Process for producing particulate resoles from aqueous dispersion |
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) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110402262A (zh) * | 2016-12-23 | 2019-11-01 | 胡坦斯·阿尔伯图斯化学厂有限公司 | 用于在双组分粘合剂体系的酚醛树脂组分中使用的酚醛树脂 |
Families Citing this family (10)
| 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 |
| AU717690B2 (en) * | 1996-06-19 | 2000-03-30 | Nevamar Company, Llc | Resin encapsulated particles |
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 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 JP JP3405577A patent/JPS52141893A/ja active Granted
- 1977-03-29 IT IT21847/77A patent/IT1075684B/it active
- 1977-03-29 ES ES457291A patent/ES457291A1/es not_active Expired
- 1977-03-29 FR FR7709408A patent/FR2346383A1/fr active Granted
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110402262A (zh) * | 2016-12-23 | 2019-11-01 | 胡坦斯·阿尔伯图斯化学厂有限公司 | 用于在双组分粘合剂体系的酚醛树脂组分中使用的酚醛树脂 |
| US11230623B2 (en) | 2016-12-23 | 2022-01-25 | HÜTTENES-ALBERTUS Chemische Werke Gesellschaft mit beschränkter Haftung | Phenol resin for use in the phenol resin component of a two-component binder system |
| CN110402262B (zh) * | 2016-12-23 | 2022-11-04 | 胡坦斯·阿尔伯图斯化学厂有限公司 | 用于在双组分粘合剂体系的酚醛树脂组分中使用的酚醛树脂 |
Also Published As
| Publication number | Publication date |
|---|---|
| ES457291A1 (es) | 1978-02-16 |
| JPS52141893A (en) | 1977-11-26 |
| DE2713852A1 (de) | 1977-10-06 |
| DE2713852B2 (de) | 1980-06-26 |
| JPS619967B2 (enrdf_load_stackoverflow) | 1986-03-27 |
| FR2346383B1 (enrdf_load_stackoverflow) | 1984-02-03 |
| DE2713852C3 (de) | 1981-02-26 |
| MX144451A (es) | 1981-10-16 |
| AU2369277A (en) | 1978-10-05 |
| IT1075684B (it) | 1985-04-22 |
| AU518241B2 (en) | 1981-09-24 |
| FR2346383A1 (fr) | 1977-10-28 |
| SE7703628L (sv) | 1977-11-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4206095A (en) | Process for producing particulate resoles from aqueous dispersion | |
| US4366303A (en) | Particulate resoles with improved cure rate and sinter resistance | |
| EP1874866B1 (en) | Stable aqueous dispersions of hydrophilic phenolic resins having low xylenol and bisphenol-a content | |
| US4182696A (en) | Process for producing particulate filler-containing resole molding compositions from aqueous dispersion | |
| GB1575366A (en) | Process for producing particulate resoles from aqueous dispersion | |
| CA1185042A (en) | Granular or powdery phenol-formaldehyde resin and process for production thereof | |
| US4788236A (en) | Process for producing particulate novolac resins and aqueous dispersions | |
| CA1262001A (en) | Microspherical cured phenolic resin particles and process for production thereof | |
| EP0071061B1 (en) | Granular or powdery nitrogen-containing phenol-aldehyde copolymer resin and process for production thereof | |
| US2956033A (en) | Lignin-phenol-formaldehyde resins, and method of preparation | |
| CA1216697A (en) | Process for producing particulate novolac resins and aqueous dispersions | |
| US3472915A (en) | Process of preparing seemingly one-stage novolacs | |
| JP5586150B2 (ja) | 粒状フェノール樹脂およびその製造方法、ならびに粒状フェノール樹脂分散液 | |
| JPH1160664A (ja) | 感圧熱自硬化性球状フェノール樹脂の製造方法 | |
| CA1120186A (en) | Process for producing particulate resoles from aqueous dispersion | |
| CA1049174A (en) | Process for the production of phenol-acetone formaldehyde binders for weather-proof wood materials and product | |
| JPS61115920A (ja) | 粒子状固形レゾ−ル樹脂組成物の製造方法 | |
| JPH07119268B2 (ja) | ノボラック型フェノール樹脂の製造方法 | |
| US2965601A (en) | Brittle furfurylated phenolic resins and method of making same | |
| US1980987A (en) | Xylenitic resin and process of making same | |
| JPS6051490B2 (ja) | レゾルシン系共重合体の製造方法 | |
| JPS62235312A (ja) | 微小球状硬化フエノ−ル樹脂粒子の製造法 | |
| JPH1081809A (ja) | 大粒径フェノール樹脂組成物の製造方法 | |
| JPH03265619A (ja) | 粉末フェノール系樹脂の製造方法 | |
| JPH0641502B2 (ja) | レゾール型フェノール樹脂の製造方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19930329 |