FI64612C - Foerfarande foer framstaellning av ett kolhydrat-fenolharts oc anvaendning av detta - Google Patents
Foerfarande foer framstaellning av ett kolhydrat-fenolharts oc anvaendning av detta Download PDFInfo
- Publication number
- FI64612C FI64612C FI772250A FI772250A FI64612C FI 64612 C FI64612 C FI 64612C FI 772250 A FI772250 A FI 772250A FI 772250 A FI772250 A FI 772250A FI 64612 C FI64612 C FI 64612C
- Authority
- FI
- Finland
- Prior art keywords
- resin
- process according
- phenol
- carbohydrate
- reaction
- Prior art date
Links
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 89
- 229920005989 resin Polymers 0.000 claims description 79
- 239000011347 resin Substances 0.000 claims description 79
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 71
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 48
- 238000006243 chemical reaction Methods 0.000 claims description 46
- 239000004202 carbamide Substances 0.000 claims description 36
- 150000001720 carbohydrates Chemical class 0.000 claims description 30
- 235000014633 carbohydrates Nutrition 0.000 claims description 29
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical group O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 26
- 229920002472 Starch Polymers 0.000 claims description 23
- 235000019698 starch Nutrition 0.000 claims description 22
- 238000009833 condensation Methods 0.000 claims description 20
- 230000005494 condensation Effects 0.000 claims description 20
- 229920003987 resole Polymers 0.000 claims description 19
- -1 phenylene, substituted phenylene Chemical group 0.000 claims description 17
- 239000008107 starch Substances 0.000 claims description 17
- 230000008569 process Effects 0.000 claims description 15
- 150000002989 phenols Chemical class 0.000 claims description 14
- 239000003054 catalyst Substances 0.000 claims description 12
- 239000007788 liquid Substances 0.000 claims description 10
- 239000011120 plywood Substances 0.000 claims description 8
- 239000007787 solid Substances 0.000 claims description 8
- 239000000853 adhesive Substances 0.000 claims description 7
- 230000001070 adhesive effect Effects 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 6
- 229920001568 phenolic resin Polymers 0.000 claims description 6
- 239000005011 phenolic resin Substances 0.000 claims description 6
- 239000003377 acid catalyst Substances 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 150000002402 hexoses Chemical class 0.000 claims description 4
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical group [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims description 3
- 239000000920 calcium hydroxide Substances 0.000 claims description 3
- 229910001861 calcium hydroxide Inorganic materials 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 239000003431 cross linking reagent Substances 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- TWNIBLMWSKIRAT-VFUOTHLCSA-N levoglucosan Chemical group O[C@@H]1[C@@H](O)[C@H](O)[C@H]2CO[C@@H]1O2 TWNIBLMWSKIRAT-VFUOTHLCSA-N 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 31
- 239000008121 dextrose Substances 0.000 description 31
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 10
- 238000009835 boiling Methods 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 8
- 239000007822 coupling agent Substances 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 239000000376 reactant Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000007654 immersion Methods 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 150000001299 aldehydes Chemical class 0.000 description 5
- 238000006482 condensation reaction Methods 0.000 description 5
- 235000013312 flour Nutrition 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 240000008042 Zea mays Species 0.000 description 4
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 4
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 4
- 235000005822 corn Nutrition 0.000 description 4
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 4
- 239000012263 liquid product Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 229920001187 thermosetting polymer Polymers 0.000 description 4
- 150000007945 N-acyl ureas Chemical class 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000005452 bending Methods 0.000 description 3
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 238000000465 moulding Methods 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 240000000968 Parkia biglobosa Species 0.000 description 2
- 235000015754 Parkia biglobosa Nutrition 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 238000004026 adhesive bonding Methods 0.000 description 2
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 2
- 239000000292 calcium oxide Substances 0.000 description 2
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 2
- 235000013339 cereals Nutrition 0.000 description 2
- 230000032798 delamination Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000003292 glue Substances 0.000 description 2
- 239000004312 hexamethylene tetramine Substances 0.000 description 2
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- 150000002772 monosaccharides Chemical class 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- AVMNUONQLWZXGR-FAOVPRGRSA-N (2r,3s,4r,5r)-2,3,4,5,6-pentahydroxyhexanal;phenol;urea Chemical compound NC(N)=O.OC1=CC=CC=C1.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O AVMNUONQLWZXGR-FAOVPRGRSA-N 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 1
- VADKRMSMGWJZCF-UHFFFAOYSA-N 2-bromophenol Chemical compound OC1=CC=CC=C1Br VADKRMSMGWJZCF-UHFFFAOYSA-N 0.000 description 1
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 1
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
- 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 1
- DBTMGCOVALSLOR-UHFFFAOYSA-N 32-alpha-galactosyl-3-alpha-galactosyl-galactose Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(OC2C(C(CO)OC(O)C2O)O)OC(CO)C1O DBTMGCOVALSLOR-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- FNGLQNMQHOAIJQ-UHFFFAOYSA-N Cl[S](Cl)Cl Chemical compound Cl[S](Cl)Cl FNGLQNMQHOAIJQ-UHFFFAOYSA-N 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- RXVWSYJTUUKTEA-UHFFFAOYSA-N D-maltotriose Natural products OC1C(O)C(OC(C(O)CO)C(O)C(O)C=O)OC(CO)C1OC1C(O)C(O)C(O)C(CO)O1 RXVWSYJTUUKTEA-UHFFFAOYSA-N 0.000 description 1
- 108010068370 Glutens Proteins 0.000 description 1
- 229920002527 Glycogen Polymers 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 1
- 240000003183 Manihot esculenta Species 0.000 description 1
- 235000016735 Manihot esculenta subsp esculenta Nutrition 0.000 description 1
- 229920000881 Modified starch Polymers 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
- 235000011613 Pinus brutia Nutrition 0.000 description 1
- 241000018646 Pinus brutia Species 0.000 description 1
- 244000062793 Sorghum vulgare Species 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 244000269722 Thea sinensis Species 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 235000007264 Triticum durum Nutrition 0.000 description 1
- 241000209143 Triticum turgidum subsp. durum Species 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- GZCGUPFRVQAUEE-SLPGGIOYSA-N aldehydo-D-glucose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O GZCGUPFRVQAUEE-SLPGGIOYSA-N 0.000 description 1
- 150000001323 aldoses Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- FAPDDOBMIUGHIN-UHFFFAOYSA-K antimony trichloride Chemical compound Cl[Sb](Cl)Cl FAPDDOBMIUGHIN-UHFFFAOYSA-K 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- GUBGYTABKSRVRQ-QUYVBRFLSA-N beta-maltose Chemical compound OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O GUBGYTABKSRVRQ-QUYVBRFLSA-N 0.000 description 1
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- XXUJMEYKYHETBZ-UHFFFAOYSA-N ethyl 4-nitrophenyl ethylphosphonate Chemical compound CCOP(=O)(CC)OC1=CC=C([N+]([O-])=O)C=C1 XXUJMEYKYHETBZ-UHFFFAOYSA-N 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 229930182478 glucoside Natural products 0.000 description 1
- 150000008131 glucosides Chemical class 0.000 description 1
- 235000021312 gluten Nutrition 0.000 description 1
- 229940096919 glycogen Drugs 0.000 description 1
- JYVHOGDBFNJNMR-UHFFFAOYSA-N hexane;hydrate Chemical compound O.CCCCCC JYVHOGDBFNJNMR-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- FYGDTMLNYKFZSV-UHFFFAOYSA-N mannotriose Natural products OC1C(O)C(O)C(CO)OC1OC1C(CO)OC(OC2C(OC(O)C(O)C2O)CO)C(O)C1O FYGDTMLNYKFZSV-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 235000019713 millet Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 150000002972 pentoses Chemical class 0.000 description 1
- 239000011846 petroleum-based material Substances 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 229940100486 rice starch Drugs 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 229940100445 wheat starch Drugs 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- FYGDTMLNYKFZSV-BYLHFPJWSA-N β-1,4-galactotrioside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@H](CO)O[C@@H](O[C@@H]2[C@@H](O[C@@H](O)[C@H](O)[C@H]2O)CO)[C@H](O)[C@H]1O FYGDTMLNYKFZSV-BYLHFPJWSA-N 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
- C08G8/04—Condensation polymers of aldehydes or ketones with phenols only of aldehydes
- C08G8/06—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of furfural
-
- 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
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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Adhesives Or Adhesive Processes (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/707,600 US4048127A (en) | 1976-07-22 | 1976-07-22 | Carbohydrate-based condensation resin |
| US70760076 | 1976-07-22 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI772250A FI772250A (US06650917-20031118-M00005.png) | 1978-01-23 |
| FI64612B FI64612B (fi) | 1983-08-31 |
| FI64612C true FI64612C (fi) | 1983-12-12 |
Family
ID=24842350
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI772250A FI64612C (fi) | 1976-07-22 | 1977-07-21 | Foerfarande foer framstaellning av ett kolhydrat-fenolharts oc anvaendning av detta |
Country Status (15)
Families Citing this family (44)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1571277A (en) * | 1978-05-31 | 1980-07-09 | Tate & Lyle Ltd | Phenol formaldehydr resins |
| US4339361A (en) * | 1980-07-28 | 1982-07-13 | Fiberglas Canada, Inc. | Phenol-formaldehyde resins extended with carbohydrates for use in binder compositions |
| US4524164A (en) * | 1983-12-02 | 1985-06-18 | Chemical Process Corporation | Thermosetting adhesive resins |
| US4692478A (en) * | 1986-03-14 | 1987-09-08 | Chemical Process Corporation | Process for preparation of resin and resin obtained |
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| KR102212329B1 (ko) * | 2005-07-26 | 2021-02-08 | 크나우프 인설레이션, 인크. | 접착제 및 이들로 만들어진 물질 |
| DK2826903T3 (da) | 2007-01-25 | 2023-06-06 | Knauf Insulation | Fremgangsmåde til fremstilling af mineralfiberisoleringsprodukt |
| BRPI0721232B1 (pt) | 2007-01-25 | 2023-01-24 | Knauf Insulation Limited | Placa de madeira compósita |
| CN101668713B (zh) | 2007-01-25 | 2012-11-07 | 可耐福保温材料有限公司 | 矿物纤维板 |
| EP3795546A1 (en) | 2007-01-25 | 2021-03-24 | Knauf Insulation GmbH | Binders and materials made therewith |
| CA2683706A1 (en) | 2007-04-13 | 2008-10-23 | Knauf Insulation Gmbh | Composite maillard-resole binders |
| GB0715100D0 (en) | 2007-08-03 | 2007-09-12 | Knauf Insulation Ltd | Binders |
| CA2770396A1 (en) | 2009-08-07 | 2011-02-10 | Knauf Insulation | Molasses binder |
| US9365963B2 (en) * | 2009-08-11 | 2016-06-14 | Johns Manville | Curable fiberglass binder |
| US9034970B2 (en) * | 2009-08-11 | 2015-05-19 | Johns Manville | Curable fiberglass binder comprising salt of inorganic acid |
| US20110040010A1 (en) * | 2009-08-11 | 2011-02-17 | Kiarash Alavi Shooshtari | Curable fiberglass binder comprising salt of inorganic acid |
| US9994482B2 (en) | 2009-08-11 | 2018-06-12 | Johns Manville | Curable fiberglass binder |
| US9604878B2 (en) | 2009-08-11 | 2017-03-28 | Johns Manville | Curable fiberglass binder comprising salt of inorganic acid |
| US9676954B2 (en) | 2009-08-11 | 2017-06-13 | Johns Manville | Formaldehyde-free binder compositions and methods of making the binders under controlled acidic conditions |
| US8708162B2 (en) | 2009-08-19 | 2014-04-29 | Johns Manville | Polymeric fiber webs with binder comprising salt of inorganic acid |
| AU2011249759B2 (en) | 2010-05-07 | 2014-11-06 | Knauf Insulation | Carbohydrate polyamine binders and materials made therewith |
| MX339649B (es) * | 2010-05-07 | 2016-06-02 | Knauf Insulation * | Aglutinantes de carbohidrato y materiales hechos con los mismos. |
| CA2801546C (en) | 2010-06-07 | 2018-07-10 | Knauf Insulation | Fiber products having temperature control additives |
| CA2834816C (en) | 2011-05-07 | 2020-05-12 | Knauf Insulation | Liquid high solids binder composition |
| BE1020571A3 (fr) * | 2011-11-04 | 2014-01-07 | Knauf Insulation | Liants et materiaux qui en decoulent. |
| BE1020570A3 (fr) * | 2011-11-04 | 2014-01-07 | Knauf Insulation | Liants et materiaux qui en decoulent. |
| FR2982268A1 (fr) * | 2011-11-07 | 2013-05-10 | Knauf Insulation | Liants et materiaux qui en decoulent |
| FR2982267A1 (fr) * | 2011-11-07 | 2013-05-10 | Knauf Insulation | Liants et materiaux qui en decoulent |
| ES2640272T3 (es) * | 2011-11-23 | 2017-11-02 | Basf Se | Aglutinante acuoso para sustratos granulados y/o fibrosos |
| GB201206193D0 (en) | 2012-04-05 | 2012-05-23 | Knauf Insulation Ltd | Binders and associated products |
| US10815593B2 (en) | 2012-11-13 | 2020-10-27 | Johns Manville | Viscosity modified formaldehyde-free binder compositions |
| US9695311B2 (en) | 2012-07-27 | 2017-07-04 | Johns Manville | Formaldehyde-free binder compositions and methods of making the binders |
| GB201214734D0 (en) | 2012-08-17 | 2012-10-03 | Knauf Insulation Ltd | Wood board and process for its production |
| WO2014086777A2 (en) | 2012-12-05 | 2014-06-12 | Knauf Insulation | Binder |
| US11401204B2 (en) | 2014-02-07 | 2022-08-02 | Knauf Insulation, Inc. | Uncured articles with improved shelf-life |
| GB201408909D0 (en) | 2014-05-20 | 2014-07-02 | Knauf Insulation Ltd | Binders |
| GB201517867D0 (en) | 2015-10-09 | 2015-11-25 | Knauf Insulation Ltd | Wood particle boards |
| JPWO2017187907A1 (ja) * | 2016-04-25 | 2019-03-07 | 株式会社ブリヂストン | ゴム配合用フェノール樹脂、ゴム組成物及びタイヤ |
| GB201610063D0 (en) | 2016-06-09 | 2016-07-27 | Knauf Insulation Ltd | Binders |
| GB201701569D0 (en) | 2017-01-31 | 2017-03-15 | Knauf Insulation Ltd | Improved binder compositions and uses thereof |
| GB201804908D0 (en) | 2018-03-27 | 2018-05-09 | Knauf Insulation Ltd | Binder compositions and uses thereof |
| GB201804907D0 (en) | 2018-03-27 | 2018-05-09 | Knauf Insulation Ltd | Composite products |
| EP4389790A1 (en) | 2022-12-23 | 2024-06-26 | Lignum Technologies AG | Method for the production of aminoplast resin, aminoplast resin, method for the production of composite materials and composite material |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1820816A (en) * | 1920-08-12 | 1931-08-25 | Continental Diamond Fibre Co | Synthetic resin and method of making same |
| US1801052A (en) * | 1923-02-06 | 1931-04-14 | Meigsoid Corp | Resinous condensation product and process of making same |
| US1815930A (en) * | 1923-10-19 | 1931-07-28 | John Stogdell Stokes | Condensation product of phenols and starches |
| US1801053A (en) * | 1925-01-22 | 1931-04-14 | Meigsoid Corp | Carbohydrate product and process of making same |
| US1593342A (en) * | 1925-11-30 | 1926-07-20 | Joseph V Meigs | Dehydrated carbohydrate-phenolic resinous products and process of making same |
| US2555058A (en) * | 1940-01-24 | 1951-05-29 | Impregnation Clichy L | Plastics obtained from amylaceous materials and methods of preparing such plastics |
| US2341907A (en) * | 1941-04-09 | 1944-02-15 | Resinous Prod & Chemical Co | Process of removing acidic constituents from fluids |
| US2362086A (en) * | 1941-08-26 | 1944-11-07 | Resinous Prod & Chemical Co | Volume stabilized acid absorbing resin |
-
1976
- 1976-07-22 US US05/707,600 patent/US4048127A/en not_active Expired - Lifetime
-
1977
- 1977-06-21 US US05/808,580 patent/US4085076A/en not_active Expired - Lifetime
- 1977-06-29 SE SE7707501A patent/SE7707501L/ not_active Application Discontinuation
- 1977-07-15 GB GB29853/77A patent/GB1530580A/en not_active Expired
- 1977-07-19 NL NL7708038A patent/NL7708038A/xx not_active Application Discontinuation
- 1977-07-20 BE BE2056098A patent/BE856965A/xx not_active IP Right Cessation
- 1977-07-21 SU SU772505305A patent/SU784787A3/ru active
- 1977-07-21 FI FI772250A patent/FI64612C/fi not_active IP Right Cessation
- 1977-07-21 ES ES460911A patent/ES460911A1/es not_active Expired
- 1977-07-21 DE DE19772732992 patent/DE2732992A1/de not_active Withdrawn
- 1977-07-21 FR FR7722411A patent/FR2359168A1/fr active Granted
- 1977-07-21 AT AT0528577A patent/AT368765B/de not_active IP Right Cessation
- 1977-07-21 CH CH908977A patent/CH633815A5/de not_active IP Right Cessation
- 1977-07-21 NO NO772603A patent/NO146474C/no unknown
- 1977-07-22 ZA ZA00774445A patent/ZA774445B/xx unknown
-
1979
- 1979-12-30 MY MY164/79A patent/MY7900164A/xx unknown
-
1982
- 1982-08-11 SE SE8204645A patent/SE8204645L/sv not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| NO146474C (no) | 1982-10-20 |
| AT368765B (de) | 1982-11-10 |
| SU784787A3 (ru) | 1980-11-30 |
| DE2732992A1 (de) | 1978-02-02 |
| SE8204645D0 (sv) | 1982-08-11 |
| FI64612B (fi) | 1983-08-31 |
| NO146474B (no) | 1982-06-28 |
| FI772250A (US06650917-20031118-M00005.png) | 1978-01-23 |
| MY7900164A (en) | 1979-12-31 |
| BE856965A (fr) | 1978-01-20 |
| US4085076A (en) | 1978-04-18 |
| ES460911A1 (es) | 1978-05-16 |
| SE8204645L (sv) | 1982-08-11 |
| FR2359168B1 (US06650917-20031118-M00005.png) | 1984-04-13 |
| CH633815A5 (de) | 1982-12-31 |
| NO772603L (no) | 1978-01-24 |
| FR2359168A1 (fr) | 1978-02-17 |
| SE7707501L (sv) | 1978-01-23 |
| GB1530580A (en) | 1978-11-01 |
| ZA774445B (en) | 1978-06-28 |
| US4048127A (en) | 1977-09-13 |
| NL7708038A (nl) | 1978-01-24 |
| ATA528577A (de) | 1982-03-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: CPC INTERNATIONAL, INC. |