CA1043977A - Phenolic resin fibers and production thereof - Google Patents
Phenolic resin fibers and production thereofInfo
- Publication number
- CA1043977A CA1043977A CA137,091A CA137091A CA1043977A CA 1043977 A CA1043977 A CA 1043977A CA 137091 A CA137091 A CA 137091A CA 1043977 A CA1043977 A CA 1043977A
- Authority
- CA
- Canada
- Prior art keywords
- fiber
- set forth
- fibers
- groups
- resin
- 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
- 239000000835 fiber Substances 0.000 title claims abstract description 163
- 229920001568 phenolic resin Polymers 0.000 title claims abstract description 48
- 239000005011 phenolic resin Substances 0.000 title claims abstract description 48
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 title claims abstract description 38
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 51
- 229920005989 resin Polymers 0.000 claims abstract description 43
- 239000011347 resin Substances 0.000 claims abstract description 43
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 36
- 230000032050 esterification Effects 0.000 claims abstract description 24
- 238000005886 esterification reaction Methods 0.000 claims abstract description 24
- 230000003647 oxidation Effects 0.000 claims abstract description 19
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 19
- 239000002253 acid Substances 0.000 claims abstract description 18
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 17
- 238000006266 etherification reaction Methods 0.000 claims abstract description 17
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims abstract description 8
- 150000008064 anhydrides Chemical class 0.000 claims abstract description 7
- 150000004820 halides Chemical class 0.000 claims abstract description 7
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229940008406 diethyl sulfate Drugs 0.000 claims abstract description 4
- 239000007788 liquid Substances 0.000 claims description 29
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical group CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 27
- 229920003986 novolac Polymers 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- 150000007513 acids Chemical class 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 125000002252 acyl group Chemical group 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 5
- 230000003197 catalytic effect Effects 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 159000000000 sodium salts Chemical class 0.000 claims description 2
- 239000007859 condensation product Substances 0.000 claims 1
- 150000001735 carboxylic acids Chemical class 0.000 abstract description 2
- 230000000903 blocking effect Effects 0.000 description 24
- 239000000376 reactant Substances 0.000 description 21
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- 230000008961 swelling Effects 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
- 238000009835 boiling Methods 0.000 description 11
- 229920003987 resole Polymers 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- 238000004132 cross linking Methods 0.000 description 8
- 230000021736 acetylation Effects 0.000 description 7
- 238000006640 acetylation reaction Methods 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 150000001768 cations Chemical class 0.000 description 6
- 150000001805 chlorine compounds Chemical class 0.000 description 6
- -1 methylol groups Chemical group 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 229940032330 sulfuric acid Drugs 0.000 description 6
- 230000004584 weight gain Effects 0.000 description 6
- 235000019786 weight gain Nutrition 0.000 description 6
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 5
- 239000003085 diluting agent Substances 0.000 description 5
- 230000006872 improvement Effects 0.000 description 5
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 5
- 241000282326 Felis catus Species 0.000 description 4
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 4
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- 229950011008 tetrachloroethylene Drugs 0.000 description 4
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-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
- 230000010933 acylation Effects 0.000 description 3
- 238000005917 acylation reaction Methods 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000007069 methylation reaction Methods 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- 239000004753 textile Substances 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- OHLUUHNLEMFGTQ-UHFFFAOYSA-N N-methylacetamide Chemical compound CNC(C)=O OHLUUHNLEMFGTQ-UHFFFAOYSA-N 0.000 description 2
- 229930040373 Paraformaldehyde Chemical group 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- OEBRKCOSUFCWJD-UHFFFAOYSA-N dichlorvos Chemical compound COP(=O)(OC)OC=C(Cl)Cl OEBRKCOSUFCWJD-UHFFFAOYSA-N 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical group C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 2
- 238000002074 melt spinning Methods 0.000 description 2
- 230000011987 methylation Effects 0.000 description 2
- 229920002866 paraformaldehyde Chemical group 0.000 description 2
- 230000035515 penetration Effects 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- PNVPNXKRAUBJGW-UHFFFAOYSA-N (2-chloroacetyl) 2-chloroacetate Chemical compound ClCC(=O)OC(=O)CCl PNVPNXKRAUBJGW-UHFFFAOYSA-N 0.000 description 1
- OZDGMOYKSFPLSE-UHFFFAOYSA-N 2-Methylaziridine Chemical compound CC1CN1 OZDGMOYKSFPLSE-UHFFFAOYSA-N 0.000 description 1
- 238000012935 Averaging Methods 0.000 description 1
- 229920000049 Carbon (fiber) Polymers 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 235000013382 Morus laevigata Nutrition 0.000 description 1
- 244000278455 Morus laevigata Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical group OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 230000000397 acetylating effect Effects 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 230000002730 additional effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001351 alkyl iodides Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 150000001541 aziridines Chemical class 0.000 description 1
- FYXKZNLBZKRYSS-UHFFFAOYSA-N benzene-1,2-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC=C1C(Cl)=O FYXKZNLBZKRYSS-UHFFFAOYSA-N 0.000 description 1
- FDQSRULYDNDXQB-UHFFFAOYSA-N benzene-1,3-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC(C(Cl)=O)=C1 FDQSRULYDNDXQB-UHFFFAOYSA-N 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical class CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000004917 carbon fiber Substances 0.000 description 1
- GPUADMRJQVPIAS-QCVDVZFFSA-M cerivastatin sodium Chemical compound [Na+].COCC1=C(C(C)C)N=C(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O)=C1C1=CC=C(F)C=C1 GPUADMRJQVPIAS-QCVDVZFFSA-M 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 229940113088 dimethylacetamide Drugs 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- WTDFFADXONGQOM-UHFFFAOYSA-N formaldehyde;hydrochloride Chemical compound Cl.O=C WTDFFADXONGQOM-UHFFFAOYSA-N 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000004312 hexamethylene tetramine Substances 0.000 description 1
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical group O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 238000002103 osmometry Methods 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene 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
- C08G8/28—Chemically modified polycondensates
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F6/00—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
- D01F6/58—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products
- D01F6/76—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products from other polycondensation products
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Phenolic Resins Or Amino Resins (AREA)
- Artificial Filaments (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13001771A | 1971-03-31 | 1971-03-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1043977A true CA1043977A (en) | 1978-12-12 |
Family
ID=22442654
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA137,091A Expired CA1043977A (en) | 1971-03-31 | 1972-03-14 | Phenolic resin fibers and production thereof |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3716521A (enExample) |
| JP (1) | JPS5032360B1 (enExample) |
| AU (1) | AU459298B2 (enExample) |
| CA (1) | CA1043977A (enExample) |
| DE (1) | DE2214281C3 (enExample) |
| FR (1) | FR2132246B1 (enExample) |
| GB (1) | GB1385502A (enExample) |
| ZA (1) | ZA722164B (enExample) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4001477A (en) * | 1971-01-18 | 1977-01-04 | The Carborundum Company | Flame resistant cloth |
| JPS5010408B2 (enExample) * | 1971-11-06 | 1975-04-21 | ||
| US4021410A (en) * | 1971-11-13 | 1977-05-03 | Nippon Kynol Inc. | Melt-spun drawn or undrawn flame-resistant and antifusing cured epoxy-modified novolak filaments and process for production thereof |
| JPS5034125B2 (enExample) * | 1972-02-22 | 1975-11-06 | ||
| JPS515090B2 (enExample) * | 1972-02-24 | 1976-02-17 | ||
| US4008304A (en) * | 1972-02-23 | 1977-02-15 | Nippon Kynol Incorporated | Process for producing cured phenolic filaments having improved drawability |
| US3918901A (en) * | 1972-04-14 | 1975-11-11 | Kaneko Ltd | Method for coloring fibrous material composed of phenolic resins |
| JPS539311B2 (enExample) * | 1972-04-20 | 1978-04-05 | ||
| US4207408A (en) * | 1972-05-22 | 1980-06-10 | The Carborundum Company | High tenacity phenolic resin fibers |
| JPS5021568B2 (enExample) * | 1972-06-03 | 1975-07-24 | ||
| US4067769A (en) * | 1972-09-05 | 1978-01-10 | Kanebo, Ltd. | Heat resistant and flame resistant papers |
| US3903220A (en) * | 1972-12-04 | 1975-09-02 | Carborundum Co | Method for producing carbon fibers |
| JPS5133231B2 (enExample) * | 1973-10-24 | 1976-09-18 | ||
| US3967925A (en) * | 1974-09-19 | 1976-07-06 | The Carborundum Company | Cationic dyeing of novoloid fibers |
| US3993442A (en) * | 1974-09-19 | 1976-11-23 | The Carborundum Company | Anionic dyeing of novoloid fibers |
| US3942947A (en) * | 1974-09-19 | 1976-03-09 | The Carborundum Company | Dyeing novoloid fibers with disperse dyes |
| DE2650025A1 (de) * | 1976-10-30 | 1978-05-11 | Zimmer Ag | Verfahren zur herstellung von linearen phenol-formaldehyd-kondensaten |
| US4965325A (en) * | 1987-11-23 | 1990-10-23 | E. I. Du Pont De Nemours And Company | Stain resistant polymers & textiles |
| US5541263A (en) * | 1995-03-16 | 1996-07-30 | Shipley Company, L.L.C. | Polymer having inert blocking groups |
| JPH11131385A (ja) * | 1997-11-05 | 1999-05-18 | Oji Paper Co Ltd | 積層板用基材及びその製造法ならびにプリプレグ及び積層板 |
| US6478998B1 (en) * | 2000-09-13 | 2002-11-12 | Borden Chemical, Inc. | Hybrid phenol-formaldehyde and polymeric isocyanate based adhesive and methods of synthesis and use |
| US7070709B2 (en) * | 2002-07-02 | 2006-07-04 | Grain Processing Corporation | Dust suppressant and soil stabilization composition |
| CN109721697B (zh) * | 2017-10-30 | 2021-11-02 | 彤程化学（中国）有限公司 | 一种改性腰果酚-苯酚-甲醛树脂及其制备和应用 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2101642A (en) * | 1932-10-08 | 1937-12-07 | Bakelite Corp | Molding composition |
| US2091965A (en) * | 1934-10-25 | 1937-09-07 | Glidden Co | Phenol resin ester and method of preparing |
| US2212509A (en) * | 1935-04-02 | 1940-08-27 | Glidden Co | Method of esterifying phenolic hydroxyls |
| FR839668A (fr) * | 1937-07-13 | 1939-04-07 | Ig Farbenindustrie Ag | Procédé pour diminuer la gonflabilité de résines synthétiques de phénols |
| US2470130A (en) * | 1945-02-07 | 1949-05-17 | Bakelite Corp | Caustic resistant etherified phenolformaldehyde resins |
| US2840542A (en) * | 1955-01-28 | 1958-06-24 | Westinghouse Electric Corp | Etherified phenolic resins |
| FR1500512A (fr) * | 1965-10-23 | 1967-11-03 | Archer Daniels Midland Co | Procédé de modification par un carbène de surfaces en une substance organique |
| CA1043523A (en) * | 1970-10-02 | 1978-12-05 | Nobuo Yoshizumi | Cured phenol-formaldehyde fibers and method for the production thereof |
-
1971
- 1971-03-31 US US00130017A patent/US3716521A/en not_active Expired - Lifetime
- 1971-12-07 JP JP46098383A patent/JPS5032360B1/ja active Pending
-
1972
- 1972-03-14 CA CA137,091A patent/CA1043977A/en not_active Expired
- 1972-03-22 GB GB1344372A patent/GB1385502A/en not_active Expired
- 1972-03-24 DE DE2214281A patent/DE2214281C3/de not_active Expired
- 1972-03-29 ZA ZA722164A patent/ZA722164B/xx unknown
- 1972-03-29 AU AU40514/72A patent/AU459298B2/en not_active Expired
- 1972-03-30 FR FR7211266A patent/FR2132246B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| AU459298B2 (en) | 1975-03-04 |
| AU4051472A (en) | 1973-10-04 |
| ZA722164B (en) | 1972-12-27 |
| FR2132246A1 (enExample) | 1972-11-17 |
| JPS5032360B1 (enExample) | 1975-10-20 |
| US3716521A (en) | 1973-02-13 |
| DE2214281C3 (de) | 1981-02-26 |
| DE2214281B2 (de) | 1980-06-19 |
| DE2214281A1 (de) | 1972-10-12 |
| GB1385502A (en) | 1975-02-26 |
| FR2132246B1 (enExample) | 1976-01-16 |
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