FI64609B - Foerfarande foer framstaellning av ett kolhydrat-fenolharts - Google Patents
Foerfarande foer framstaellning av ett kolhydrat-fenolharts Download PDFInfo
- Publication number
- FI64609B FI64609B FI772249A FI772249A FI64609B FI 64609 B FI64609 B FI 64609B FI 772249 A FI772249 A FI 772249A FI 772249 A FI772249 A FI 772249A FI 64609 B FI64609 B FI 64609B
- Authority
- FI
- Finland
- Prior art keywords
- reaction
- carbohydrate
- resin
- phenol
- catalyst
- Prior art date
Links
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 39
- 229920005989 resin Polymers 0.000 claims description 31
- 239000011347 resin Substances 0.000 claims description 31
- 150000001720 carbohydrates Chemical class 0.000 claims description 24
- 235000014633 carbohydrates Nutrition 0.000 claims description 24
- 239000003054 catalyst Substances 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 19
- 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 claims description 17
- 239000008121 dextrose Substances 0.000 claims description 17
- 230000008569 process Effects 0.000 claims description 16
- 229920002472 Starch Polymers 0.000 claims description 15
- 235000019698 starch Nutrition 0.000 claims description 14
- -1 phenol compound Chemical class 0.000 claims description 11
- 239000011541 reaction mixture Substances 0.000 claims description 8
- 239000007787 solid Substances 0.000 claims description 8
- 239000008107 starch Substances 0.000 claims description 8
- 239000011968 lewis acid catalyst Substances 0.000 claims description 7
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- 229920001568 phenolic resin Polymers 0.000 claims description 6
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 5
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 5
- 229910052782 aluminium Inorganic materials 0.000 claims description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 5
- 239000005011 phenolic resin Substances 0.000 claims description 5
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical group Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 claims description 5
- 229910052725 zinc Inorganic materials 0.000 claims description 5
- 239000011701 zinc Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- 229910052718 tin Inorganic materials 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical group Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 43
- 229910001868 water Inorganic materials 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 16
- 238000009833 condensation Methods 0.000 description 13
- 230000005494 condensation Effects 0.000 description 12
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 10
- 150000003839 salts Chemical class 0.000 description 8
- 150000002989 phenols Chemical class 0.000 description 7
- NOEGNKMFWQHSLB-UHFFFAOYSA-N 5-hydroxymethylfurfural Chemical compound OCC1=CC=C(C=O)O1 NOEGNKMFWQHSLB-UHFFFAOYSA-N 0.000 description 6
- 238000006482 condensation reaction Methods 0.000 description 6
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 6
- 239000011787 zinc oxide Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 235000011149 sulphuric acid Nutrition 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000004312 hexamethylene tetramine Substances 0.000 description 3
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 3
- RJGBSYZFOCAGQY-UHFFFAOYSA-N hydroxymethylfurfural Natural products COC1=CC=C(C=O)O1 RJGBSYZFOCAGQY-UHFFFAOYSA-N 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 229920001187 thermosetting polymer Polymers 0.000 description 3
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 229920002261 Corn starch Polymers 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000008120 corn starch Substances 0.000 description 2
- 239000003431 cross linking reagent Substances 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 235000013312 flour Nutrition 0.000 description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
- 239000003365 glass fiber Substances 0.000 description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 2
- 238000007654 immersion Methods 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 230000001737 promoting effect Effects 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 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
- 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
- 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
- 235000016068 Berberis vulgaris Nutrition 0.000 description 1
- 241000335053 Beta vulgaris Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 229920002527 Glycogen Polymers 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 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
- 239000002841 Lewis acid Substances 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
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 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
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- FAPDDOBMIUGHIN-UHFFFAOYSA-K antimony trichloride Chemical compound Cl[Sb](Cl)Cl FAPDDOBMIUGHIN-UHFFFAOYSA-K 0.000 description 1
- 239000010425 asbestos Substances 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-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
- 239000008116 calcium stearate Substances 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000002542 deteriorative effect Effects 0.000 description 1
- PXJJSXABGXMUSU-UHFFFAOYSA-N disulfur dichloride Chemical compound ClSSCl PXJJSXABGXMUSU-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005265 energy consumption Methods 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
- 150000004665 fatty acids Chemical class 0.000 description 1
- 150000004673 fluoride salts Chemical class 0.000 description 1
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 1
- 150000004675 formic acid derivatives Chemical class 0.000 description 1
- 229930182478 glucoside Natural products 0.000 description 1
- 150000008131 glucosides Chemical class 0.000 description 1
- 229940096919 glycogen Drugs 0.000 description 1
- 150000002402 hexoses Chemical class 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 150000004668 long chain fatty acids Chemical class 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 235000019713 millet Nutrition 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002772 monosaccharides Chemical class 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 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
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)
- Catalysts (AREA)
- Reinforced Plastic Materials (AREA)
Claims (12)
1. Förfarande för framställning av ett kolhydrat-fenolharts, kännetecknat därav, att 1. dextros eller ett kolhydrat, som vid hydrolys bildar extros, och 2. en fenolförening med formeln OH där R är Cj^-alkyl, C^_.j-alkoxI, halogen, hydroxi eller väte, omsätts med varandra i närvaro av en metallsalt-Lewis-syrakatalysator, som är ett sait av aluminium, zink eller tenn, varvid bildas ett fast lätt smältbart harts, och hartset separeras frän reaktionsblandningen.
2. Förfarande enligt patentkravet 1, kännetecknat därav, att katalysatorn är tennklorid.
3. Förfarande enligt patentkravet 1, kännetecknat därav, att katalysatorn är aluminiumklorid.
4. Förfarande enligt nägot av patentkraven 1-3, kännetecknat därav, att fenolföreningen är fenol.
5. Förfarande enligt nägot av patentkraven 1-4, kännetecknat därav, att kolhydratet är stärkelse.
6. Förfarande enligt nägot av patentkraven 1-4, kännetecknat därav, att komponenten (1) är dextros.
7. Förfarande enligt nägot av patentkraven 1-4, kännetecknat därav, att hexossackariden är stärkelse eller dess hyd-rolysprodukt med formeln CH2OH ! jCH2OH ! ch2oh hJ—q P · h J—a h ' H A—H Hofe)L_ 6 _ ό OH H* OH i ° 0H ; H °H i · ' ' n .... - -i
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/707,598 US4048126A (en) | 1976-07-22 | 1976-07-22 | Process for producing carbohydrate-phenol condensation resins |
| US70759876 | 1976-07-22 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI772249A FI772249A (sv) | 1978-01-23 |
| FI64609B true FI64609B (fi) | 1983-08-31 |
| FI64609C FI64609C (fi) | 1983-12-12 |
Family
ID=24842339
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI772249A FI64609C (fi) | 1976-07-22 | 1977-07-21 | Foerfarande foer framstaellning av ett kolhydrat-fenolharts |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US4048126A (sv) |
| AT (1) | AT368764B (sv) |
| BE (1) | BE856963A (sv) |
| CA (1) | CA1078983A (sv) |
| CH (1) | CH627766A5 (sv) |
| DE (1) | DE2732991C2 (sv) |
| ES (1) | ES460909A1 (sv) |
| FI (1) | FI64609C (sv) |
| FR (1) | FR2359166A1 (sv) |
| GB (1) | GB1531706A (sv) |
| IT (1) | IT1081548B (sv) |
| MY (1) | MY7900168A (sv) |
| NL (1) | NL186323C (sv) |
| NO (1) | NO145579C (sv) |
| SE (1) | SE7707500L (sv) |
| ZA (1) | ZA774448B (sv) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4339361A (en) * | 1980-07-28 | 1982-07-13 | Fiberglas Canada, Inc. | Phenol-formaldehyde resins extended with carbohydrates for use in binder compositions |
| US4692478A (en) * | 1986-03-14 | 1987-09-08 | Chemical Process Corporation | Process for preparation of resin and resin obtained |
| FR2625203B1 (fr) * | 1987-12-23 | 1992-03-13 | Clavier Philippe | Procede pour la fabrication de resines thermodurcissables et resines obtenues |
| FR2630119B2 (fr) * | 1987-12-23 | 1993-08-13 | Clavier Philippe | Procede pour la fabrication de resines thermodurcissables et resines obtenues |
| FR2641282B1 (fr) * | 1988-12-29 | 1992-08-07 | Clavier Philippe | Procede pour la fabrication de resines thermodurcissables resistant a l'eau bouillante et resines obtenues |
| WO2015123781A1 (en) * | 2014-02-20 | 2015-08-27 | The University Of Western Ontario | Formaldehyde-free phenolic resins, downstream products, their synthesis and use |
| WO2015187178A1 (en) * | 2014-06-06 | 2015-12-10 | Halliburton Energy Services, Inc. | Acidizing fluids and methods for use in subterranean formations |
| TWI563018B (en) | 2014-10-14 | 2016-12-21 | Ind Tech Res Inst | Hmf-based phenol formaldehyde resin |
| 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 |
| EP3366712A1 (de) | 2017-02-27 | 2018-08-29 | AVALON Industries AG | Neue hmf-oligomere |
| EP3366714B1 (de) * | 2017-02-27 | 2022-03-30 | AVA Biochem AG | Verfahren zur herstellung thermisch härtbarer phenolharze sowie durch das verfahren erhältliche phenolharze |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1107107A (en) * | 1914-06-26 | 1914-08-11 | Basf Ag | Compounds for tanning skins and process of making them. |
| US1820816A (en) * | 1920-08-12 | 1931-08-25 | Continental Diamond Fibre Co | Synthetic resin and method of making same |
| US1753030A (en) * | 1920-08-12 | 1930-04-01 | Continental Diamond Fibre Co | Phenol-carbohydrate resin and method of making same |
| US1886353A (en) * | 1922-04-27 | 1932-11-01 | John Stogdell Stokes | Synthetic resin and method of making same |
| US1832038A (en) * | 1922-07-17 | 1931-11-17 | Meigsoid Corp | Artificial resin and process of making same |
| DE529322C (de) * | 1926-02-14 | 1931-07-11 | Joseph Vincent Meigs | Verfahren zur Herstellung von haertbaren harzartigen Kondensationsprodukten aus Phenolen und Kohlehydraten |
| US1868215A (en) * | 1926-03-05 | 1932-07-19 | Plastix Corp | Carbohydrate resinous material and process of making same |
| US1868216A (en) * | 1927-01-15 | 1932-07-19 | Plastix Corp | Resinous product and process of making same |
| US1923321A (en) * | 1927-01-15 | 1933-08-22 | Plastix Corp | Resinous product and process of making same |
| US2069178A (en) * | 1932-06-27 | 1937-01-26 | Gen Plastics Inc | Method of dispersing resins and composition produced thereby |
| USRE26881E (en) | 1969-07-10 | 1970-05-19 | Method of producing an ortho-directed phenolic resin by condensing phenol and hcho in the presence of a bivalent metal ion and then adding resorcinol, and the resultant product |
-
1976
- 1976-07-22 US US05/707,598 patent/US4048126A/en not_active Expired - Lifetime
-
1977
- 1977-06-29 SE SE7707500A patent/SE7707500L/sv not_active Application Discontinuation
- 1977-07-15 GB GB29854/77A patent/GB1531706A/en not_active Expired
- 1977-07-15 IT IT25792/77A patent/IT1081548B/it active
- 1977-07-15 CA CA282,841A patent/CA1078983A/en not_active Expired
- 1977-07-19 NL NLAANVRAGE7708039,A patent/NL186323C/xx not_active IP Right Cessation
- 1977-07-20 BE BE2056096A patent/BE856963A/xx not_active IP Right Cessation
- 1977-07-21 FI FI772249A patent/FI64609C/fi not_active IP Right Cessation
- 1977-07-21 AT AT0528377A patent/AT368764B/de not_active IP Right Cessation
- 1977-07-21 NO NO772602A patent/NO145579C/no unknown
- 1977-07-21 FR FR7722409A patent/FR2359166A1/fr active Granted
- 1977-07-21 DE DE2732991A patent/DE2732991C2/de not_active Expired
- 1977-07-21 CH CH908877A patent/CH627766A5/de not_active IP Right Cessation
- 1977-07-21 ES ES460909A patent/ES460909A1/es not_active Expired
- 1977-07-22 ZA ZA00774448A patent/ZA774448B/xx unknown
-
1979
- 1979-12-30 MY MY168/79A patent/MY7900168A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| MY7900168A (en) | 1979-12-31 |
| SE7707500L (sv) | 1978-01-23 |
| DE2732991C2 (de) | 1986-08-14 |
| FR2359166B1 (sv) | 1984-04-13 |
| CA1078983A (en) | 1980-06-03 |
| ZA774448B (en) | 1978-06-28 |
| FI64609C (fi) | 1983-12-12 |
| NL7708039A (nl) | 1978-01-24 |
| CH627766A5 (de) | 1982-01-29 |
| US4048126A (en) | 1977-09-13 |
| NO772602L (no) | 1978-01-24 |
| IT1081548B (it) | 1985-05-21 |
| NO145579B (no) | 1982-01-11 |
| DE2732991A1 (de) | 1978-02-02 |
| ES460909A1 (es) | 1978-05-16 |
| NO145579C (no) | 1982-04-21 |
| ATA528377A (de) | 1982-03-15 |
| NL186323C (nl) | 1990-11-01 |
| FI772249A (sv) | 1978-01-23 |
| AT368764B (de) | 1982-11-10 |
| GB1531706A (en) | 1978-11-08 |
| NL186323B (nl) | 1990-06-01 |
| BE856963A (fr) | 1978-01-20 |
| FR2359166A1 (fr) | 1978-02-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: CPC INTERNATIONAL, INC. |