WO2013179660A1 - 液状レゾール型フェノール樹脂および湿式ペーパー摩擦材 - Google Patents
液状レゾール型フェノール樹脂および湿式ペーパー摩擦材 Download PDFInfo
- Publication number
- WO2013179660A1 WO2013179660A1 PCT/JP2013/003385 JP2013003385W WO2013179660A1 WO 2013179660 A1 WO2013179660 A1 WO 2013179660A1 JP 2013003385 W JP2013003385 W JP 2013003385W WO 2013179660 A1 WO2013179660 A1 WO 2013179660A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- resol type
- liquid resol
- phenol resin
- type phenol
- hydrocarbon group
- Prior art date
Links
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 title claims abstract description 65
- 239000007788 liquid Substances 0.000 title claims abstract description 61
- 229920003987 resole Polymers 0.000 title claims abstract description 47
- 239000002783 friction material Substances 0.000 title claims description 32
- 229920005989 resin Polymers 0.000 title abstract description 6
- 239000011347 resin Substances 0.000 title abstract description 6
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims abstract description 27
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 5
- 239000005011 phenolic resin Substances 0.000 claims description 74
- 150000002989 phenols Chemical class 0.000 claims description 28
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
- 150000001299 aldehydes Chemical class 0.000 claims description 21
- 239000003054 catalyst Substances 0.000 claims description 18
- 239000011134 resol-type phenolic resin Substances 0.000 claims description 14
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 claims description 9
- 239000003377 acid catalyst Substances 0.000 claims description 9
- JOLVYUIAMRUBRK-UHFFFAOYSA-N 11',12',14',15'-Tetradehydro(Z,Z-)-3-(8-Pentadecenyl)phenol Natural products OC1=CC=CC(CCCCCCCC=CCC=CCC=C)=C1 JOLVYUIAMRUBRK-UHFFFAOYSA-N 0.000 claims description 8
- YLKVIMNNMLKUGJ-UHFFFAOYSA-N 3-Delta8-pentadecenylphenol Natural products CCCCCCC=CCCCCCCCC1=CC=CC(O)=C1 YLKVIMNNMLKUGJ-UHFFFAOYSA-N 0.000 claims description 8
- JOLVYUIAMRUBRK-UTOQUPLUSA-N Cardanol Chemical compound OC1=CC=CC(CCCCCCC\C=C/C\C=C/CC=C)=C1 JOLVYUIAMRUBRK-UTOQUPLUSA-N 0.000 claims description 8
- FAYVLNWNMNHXGA-UHFFFAOYSA-N Cardanoldiene Natural products CCCC=CCC=CCCCCCCCC1=CC=CC(O)=C1 FAYVLNWNMNHXGA-UHFFFAOYSA-N 0.000 claims description 8
- PTFIPECGHSYQNR-UHFFFAOYSA-N cardanol Natural products CCCCCCCCCCCCCCCC1=CC=CC(O)=C1 PTFIPECGHSYQNR-UHFFFAOYSA-N 0.000 claims description 8
- KVVSCMOUFCNCGX-UHFFFAOYSA-N cardol Chemical compound CCCCCCCCCCCCCCCC1=CC(O)=CC(O)=C1 KVVSCMOUFCNCGX-UHFFFAOYSA-N 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 239000000463 material Substances 0.000 claims description 8
- 229920001568 phenolic resin Polymers 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- LDBPJTXLCRXBIJ-UHFFFAOYSA-N 11,12,14,15-Tetrahydro-(Z,Z)-2-Methyl-5-(8,11,14-pentadecatrienyl)-1,3-benzenediol Natural products CCCCCCC=CCCCCCCCC1=CC(O)=C(C)C(O)=C1 LDBPJTXLCRXBIJ-UHFFFAOYSA-N 0.000 claims description 4
- LDBPJTXLCRXBIJ-HJWRWDBZSA-N 2-Methyl-5-(8-pentadecenyl)-1,3-benzenediol Chemical compound CCCCCC\C=C/CCCCCCCC1=CC(O)=C(C)C(O)=C1 LDBPJTXLCRXBIJ-HJWRWDBZSA-N 0.000 claims description 4
- IZGYQWUVUWZOPQ-UHFFFAOYSA-N 2-Methylcardol Natural products CCCC=CCC=CCCCCCCCC1=CC(O)=C(C)C(O)=C1 IZGYQWUVUWZOPQ-UHFFFAOYSA-N 0.000 claims description 4
- UFMJCOLGRWKUKO-UHFFFAOYSA-N cardol diene Natural products CCCC=CCC=CCCCCCCCC1=CC(O)=CC(O)=C1 UFMJCOLGRWKUKO-UHFFFAOYSA-N 0.000 claims description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- 150000002430 hydrocarbons Chemical group 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 11
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- 239000002585 base Substances 0.000 description 7
- 208000034189 Sclerosis Diseases 0.000 description 6
- 239000000835 fiber Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- -1 5-tridecenylresorcinol 5-pentadecenyl resorcinol Chemical compound 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 229920000049 Carbon (fiber) Polymers 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 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
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000004917 carbon fiber Substances 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 238000005470 impregnation Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000003607 modifier Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 239000002383 tung oil Substances 0.000 description 2
- 239000003981 vehicle Substances 0.000 description 2
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- RQWDMLWKYZKPMV-UHFFFAOYSA-N 3-dodec-1-enylphenol Chemical compound CCCCCCCCCCC=CC1=CC=CC(O)=C1 RQWDMLWKYZKPMV-UHFFFAOYSA-N 0.000 description 1
- XRFYZEHRLUNWIJ-UHFFFAOYSA-N 3-pentadec-1-enylphenol Chemical compound CCCCCCCCCCCCCC=CC1=CC=CC(O)=C1 XRFYZEHRLUNWIJ-UHFFFAOYSA-N 0.000 description 1
- LYWIUCZXQCDUJA-UHFFFAOYSA-N 3-tridec-1-enylphenol Chemical compound CCCCCCCCCCCC=CC1=CC=CC(O)=C1 LYWIUCZXQCDUJA-UHFFFAOYSA-N 0.000 description 1
- FEPBITJSIHRMRT-UHFFFAOYSA-N 4-hydroxybenzenesulfonic acid Chemical compound OC1=CC=C(S(O)(=O)=O)C=C1 FEPBITJSIHRMRT-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 244000226021 Anacardium occidentale Species 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 238000003811 acetone extraction Methods 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- AYJRCSIUFZENHW-UHFFFAOYSA-L barium carbonate Inorganic materials [Ba+2].[O-]C([O-])=O AYJRCSIUFZENHW-UHFFFAOYSA-L 0.000 description 1
- 150000007514 bases Chemical group 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 235000020226 cashew nut Nutrition 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- KUCOHFSKRZZVRO-UHFFFAOYSA-N terephthalaldehyde Chemical compound O=CC1=CC=C(C=O)C=C1 KUCOHFSKRZZVRO-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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
-
- 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
- C08G10/00—Condensation polymers of aldehydes or ketones with aromatic hydrocarbons or halogenated aromatic hydrocarbons only
- C08G10/02—Condensation polymers of aldehydes or ketones with aromatic hydrocarbons or halogenated aromatic hydrocarbons only of aldehydes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/18—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring monocyclic with unsaturation outside the aromatic ring
-
- 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
-
- 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
-
- 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
- C08G8/10—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ with phenol
-
- 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
- C08G8/20—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ with polyhydric phenols
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F16—ENGINEERING ELEMENTS AND UNITS; GENERAL MEASURES FOR PRODUCING AND MAINTAINING EFFECTIVE FUNCTIONING OF MACHINES OR INSTALLATIONS; THERMAL INSULATION IN GENERAL
- F16D—COUPLINGS FOR TRANSMITTING ROTATION; CLUTCHES; BRAKES
- F16D69/00—Friction linings; Attachment thereof; Selection of coacting friction substances or surfaces
- F16D69/02—Composition of linings ; Methods of manufacturing
- F16D69/025—Compositions based on an organic binder
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F16—ENGINEERING ELEMENTS AND UNITS; GENERAL MEASURES FOR PRODUCING AND MAINTAINING EFFECTIVE FUNCTIONING OF MACHINES OR INSTALLATIONS; THERMAL INSULATION IN GENERAL
- F16D—COUPLINGS FOR TRANSMITTING ROTATION; CLUTCHES; BRAKES
- F16D69/00—Friction linings; Attachment thereof; Selection of coacting friction substances or surfaces
- F16D69/02—Composition of linings ; Methods of manufacturing
- F16D69/025—Compositions based on an organic binder
- F16D69/026—Compositions based on an organic binder containing fibres
-
- 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
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/90—Applications
Definitions
- the present invention relates to a liquid resol type phenol resin and a wet paper friction material.
- Phenol resins which are thermosetting resins, are widely used mainly as binders to bond materials that are the base materials of molded products, and have excellent mechanical properties, electrical properties, and adhesive properties. Used in. In particular, in recent years, the amount of friction materials using phenolic resin as a binder is increasing in automobiles, railway vehicles, and the like.
- a liquid resol type phenol resin is generally used for a friction material used in an automatic transmission such as an automatic vehicle, which is called a wet paper friction material.
- the required characteristics of the phenolic resin for wet paper friction materials are increasing year by year, and the demand for improving the flexibility of the phenolic resin has been increasing particularly for the purpose of improving the frictional characteristics.
- a cured product of a general phenol resin is excellent in mechanical properties, but has a property of being hard and brittle, and cannot be said to be excellent in flexibility.
- Patent Document 1 an attempt to improve flexibility using a drying oil or the like as a modifier in a reaction when synthesizing a phenol resin has been studied (for example, Patent Document 1).
- a dry oil-modified phenolic resin is characterized by high flexibility as compared with an unmodified phenolic resin since a flexible aliphatic hydrocarbon group is introduced.
- the dry oil-modified phenol resin described in Patent Document 1 has the disadvantage that not all the aliphatic hydrocarbon groups are bonded to the phenol structural unit, and the effect of improving flexibility is not sufficient.
- the reaction point of the phenol resin is decreased, and thus there is a disadvantage that curability is lowered.
- the present invention has been made in view of the above circumstances, and is excellent in terms of curability, which is a characteristic of a phenol resin, and further a liquid resol type phenol resin capable of obtaining a wet paper friction material having excellent flexibility, And a wet paper friction material using the same.
- the present inventor is a phenol resin having excellent properties in terms of curability, and provides a liquid resol type phenol resin capable of obtaining a wet paper friction material having excellent flexibility.
- the present inventors have intensively studied the existing substituents. As a result, it has been found that it is effective to obtain a phenol resin in which a linear unsaturated hydrocarbon group having 10 or more carbon atoms is bonded to at least one or more meta positions of all phenol structural units. It came to.
- liquid resol type phenol resin in which a linear unsaturated hydrocarbon group having 10 or more carbon atoms is bonded to at least one meta position of all phenol structural units.
- a wet paper friction material characterized by using the liquid resol type phenol resin.
- liquid resol type phenolic resin that is excellent in terms of curability, which is a characteristic of a phenolic resin, and capable of obtaining a wet paper friction material excellent in flexibility, and wet paper friction using the same Material can be provided.
- liquid resol type phenol resin and the wet paper friction material according to the present embodiment will be described in detail.
- the liquid resol type phenol resin according to the present embodiment is characterized in that a linear unsaturated hydrocarbon group having 10 or more carbon atoms is bonded to at least one meta position of all phenol structural units.
- a linear unsaturated hydrocarbon group having 10 or more carbon atoms is bonded to at least one meta position of all phenol structural units.
- the phenol structural unit means a structural unit having at least a structure in which a hydroxyl group (—OH) is directly bonded to carbon of a benzene ring.
- liquid resol type phenolic resin according to the present embodiment is obtained by reacting phenols (A) in which a linear unsaturated hydrocarbon group having 10 or more carbon atoms is bonded to at least one meta position. It is preferable that By carrying out like this, in order to obtain the wet paper friction material which was further excellent in the softness
- the phenols (A) according to this embodiment preferably include a structure represented by the following general formula (1).
- R represents a linear unsaturated hydrocarbon group having 10 or more carbon atoms. However, a hydrogen atom bonded to a benzene ring having a phenolic hydroxyl group may be substituted with a substituent.
- the substituent for substituting the hydrogen atom bonded to the benzene ring having a phenolic hydroxyl group is not particularly limited, and examples thereof include an acetyl group and a methyl group.
- the linear unsaturated hydrocarbon group bonded to at least one or more meta positions of all phenol structural units preferably has 10 or more carbon atoms, and more preferably has 12 or more carbon atoms.
- the linear unsaturated hydrocarbon group bonded to at least one meta position of all phenol structural units preferably has 20 or less carbon atoms, and more preferably has 18 or less carbon atoms.
- the phenols (A) according to the present embodiment are not particularly limited.
- cardanol, cardol, and 2-methylcardol are preferably used from the viewpoint of handleability. In addition, you may use these individually or may use 2 or more types together.
- the liquid resol type phenolic resin according to the present embodiment is a basic compound of the phenolic compound (B) obtained by reacting the phenols (A) in the presence of an acid catalyst with the aldehydes (C). Even what was obtained by making it react under a catalyst may be obtained by making it react under the above-mentioned phenols (A) and aldehydes (C) under a basic catalyst.
- the liquid resol type phenol resin according to the present embodiment is not particularly limited.
- (A) can be obtained by reacting a phenol compound (B) obtained by reacting in the presence of an acid catalyst with an aldehyde (C) in the presence of a basic catalyst. By doing so, the flexibility of the wet paper friction material can be further improved.
- phenols (A) itself in which a linear unsaturated hydrocarbon group having 10 or more carbon atoms is bonded to at least one meta position is acidic, the reaction can be performed without adding an acid catalyst. You can also.
- the phenolic compound (B) obtained by reacting the liquid resol type phenolic resin according to the present embodiment with the above phenols (A) in the presence of an acid catalyst, and the aldehydes (C) as a base.
- a neutral catalyst it is considered that the reaction described below is in progress.
- a proton (H + ) supplied from an acid catalyst is added to the carbon-carbon multiple bond of a straight-chain unsaturated hydrocarbon group having 10 or more carbon atoms in the phenol (A) to generate a carbocation.
- the liquid resol type phenol resin according to the present embodiment can be obtained by reacting the phenolic compound (B) thus produced with the aldehyde (C) in the presence of a basic catalyst.
- the acid catalyst used for obtaining the phenol compound (B) is not particularly limited.
- organic acids such as acetic acid and oxalic acid
- mineral acids such as hydrochloric acid, sulfuric acid and phosphoric acid, diethyl sulfuric acid, para
- para Examples include toluene sulfonic acid and paraphenol sulfonic acid.
- the liquid resol type phenol resin according to the present embodiment includes phenols (A) in which a linear unsaturated hydrocarbon group having 10 or more carbon atoms is bonded to at least one meta position. Even if it reacts with an aldehyde (C) and a basic catalyst, without making it react in presence of an acid catalyst, it can obtain. By carrying out like this, it is excellent in the viewpoint of sclerosis
- the liquid resol type phenol resin according to the present embodiment is obtained by reacting the phenols (A) and aldehydes (C) with a basic catalyst
- the liquid resol type phenol resin has the following general formula: It is preferable that the structural unit represented by (2) is repeatedly included. By carrying out like this, it is excellent in the viewpoint of sclerosis
- R represents a linear unsaturated hydrocarbon group having 10 or more carbon atoms. However, a hydrogen atom bonded to a benzene ring having a phenolic hydroxyl group may be substituted with a substituent.
- the reaction is carried out under a neutral catalyst, the molar ratio (C) / ⁇ (A) + (B) ⁇ of the reactants is preferably 0.2 or more and 1.5 or less, and 0.6 or more and 1.2 or less. Is more preferable. By setting the molar ratio during the reaction to the above range, it is possible to reduce the aldehydes (C) remaining without reacting and to obtain a phenol resin having sufficient curability.
- Phenols (A) and / or phenol compounds (B) and aldehydes (C) are reacted in the presence of a basic catalyst, or phenols (A) and aldehydes (C) are reacted with a basic catalyst
- the basic catalyst used is not particularly limited, and examples thereof include alkali metal hydroxides such as sodium hydroxide, lithium hydroxide and potassium hydroxide, tertiary amines such as aqueous ammonia and triethylamine, Examples thereof include basic substances such as oxides and hydroxides of alkaline earth metals such as calcium, magnesium and barium, and sodium carbonate. These may be used alone or in combination of two or more.
- the usage-amount of a basic catalyst is not specifically limited, What is necessary is just to be 1 mass part or more and 50 mass parts or less with respect to 1000 mass parts of phenols (A) or phenol compounds (B).
- the liquid resol type phenol resin according to the present embodiment is characterized in that a linear unsaturated hydrocarbon group having 10 or more carbon atoms is bonded to at least one or more meta positions of all phenol structural units.
- the phenols (A) and / or the phenol compounds (B) can be obtained by reacting the aldehydes (C) with a basic catalyst.
- the aldehydes (C) are not particularly limited, and examples thereof include formaldehyde, acetaldehyde, butyraldehyde, propionaldehyde, terephthalaldehyde, benzaldehyde, paraformaldehyde, acrolein and the like.
- the use is not limited to one type, and these aldehydes can be used alone or in combination of two or more.
- an organic solvent may be used for the liquid resol type phenolic resin according to the present embodiment in order to dilute the resin.
- the organic solvent used for the dilution of the resin is not particularly limited, for example, alcohol organic solvents such as methanol, ethanol, isopropanol, butanol, ketone organic solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, toluene, Aromatic hydrocarbon solvents such as ethylbenzene and mixtures thereof.
- the liquid resol type phenolic resin according to this embodiment is preferably used by impregnating the base material.
- the base material which used fibers such as a natural fiber, a metal fiber, carbon fiber, and a chemical fiber, individually or in 2 types or more is mentioned.
- the liquid resol type phenolic resin according to this embodiment is preferably used by being included in a wet paper friction material.
- a method for producing a wet paper friction material containing the liquid resol type phenol resin include, for example, a liquid resol type phenol resin, a metal fiber, a carbon fiber and a chemical fiber, a friction modifier such as cashew dust, diatomaceous earth, etc.
- a friction modifier such as cashew dust, diatomaceous earth, etc.
- the wet paper friction material according to the present embodiment uses the liquid resol type phenol resin. By carrying out like this, it is excellent in the viewpoint of the heat resistance and sclerosis
- a liquid resol type phenolic resin having a C10 or higher linear unsaturated hydrocarbon group in at least one or more meta positions of all phenol skeletons [2] A phenol compound (B) obtained by reacting a phenol (A) having a C10 or more linear unsaturated hydrocarbon group at at least one meta position in the presence of an acid catalyst, and an aldehyde (C ) And a liquid resol type phenol resin as described in [1] obtained by reacting with a basic catalyst.
- [3] Obtained by reacting a phenol (A) having a C10 or more straight chain unsaturated hydrocarbon group at at least one meta position with an aldehyde (C) in the presence of a basic catalyst, [1 ] The liquid resol type phenol resin of description. [4] The liquid resol type phenol resin according to [2] or [3], wherein the phenol (A) is at least one phenol selected from cardanol, cardol, and 2-methylcardol. [5] The liquid resol type phenol resin according to any one of [1] to [4], which is used for impregnation. [6] The liquid resol type phenol resin according to any one of [1] to [5], which is used for wet paper friction material applications. [7] A wet paper friction material comprising the liquid resol type phenol resin according to [6].
- Impregnated paper was prepared using the liquid resol type phenol resins a to d obtained in Examples and Comparative Examples.
- a commercially available filter paper 120 mm ⁇ 10 mm ⁇ thickness 1 mm was used as the substrate.
- liquid resol type phenol resins a to d obtained in Examples and Comparative Examples were diluted with acetone to impregnate the filter paper in a solution having a resin concentration of 30%, and then dried in an oven at 190 ° C. for 30 minutes. And cured to obtain a test piece.
- Test item Tensile strength: The obtained test piece was measured according to JIS P8113. The unit is MPa. The measurement conditions were as follows. The test piece prepared by the above method was used at a test speed of 1 mm / min under normal temperature and normal pressure using a precision universal testing machine AG-IS 5 kN (manufactured by Shimadzu Corporation).
- Tensile elongation at break The obtained test piece was measured according to JIS P 8113. The unit is%. The measurement conditions were as follows. The test piece produced by the above method was subjected to a test speed of 1 mm / min under normal temperature and normal pressure using a precision universal testing machine AG-IS 5 kN (manufactured by Shimadzu Corporation).
- Liquid resol type phenol resins a to d obtained in Examples and Comparative Examples were cured at 190 ° C. for 30 minutes, then pulverized with a bead mill, sieved, passed through 149 ⁇ m, and remained above 63 ⁇ m. Minutes were used as samples. About 20 glass beads were placed in a Soxhlet flask, and 200 ml of acetone was added. Put a cylindrical filter paper in the extraction tube, put about 3 g of the weighed sample in the filter paper, attach a condenser and fix it in a water bath state, reflux, and soak the sample in acetone for 6 hours. After drying with a vacuum drier, the acetone extraction rate was calculated from the remaining weight. In addition, it can be judged that hardening is progressing, so that there is little acetone melt
- the cured products of the phenol resins a and b obtained in Examples 1 and 2 are excellent in curability because of a small amount of acetone dissolved, and excellent in flexibility because of a high tensile elongation at break. I understand that there is. Actually, when a wet paper friction material was produced using the phenol resins a and b described in Examples, a wet paper friction material having excellent flexibility could be obtained.
- the phenolic resin c obtained in Comparative Example 1 is an unmodified liquid resol type phenolic resin obtained from phenol and formaldehyde, and the phenolic resin d obtained in Comparative Example 2 was modified with tung oil which is a drying oil. It is a liquid resol type phenol resin.
- the phenol resin d of Comparative Example 2 was larger in tensile elongation at break than the phenol resin c of Comparative Example 1 and was excellent in flexibility. However, it was more flexible than the phenol resins a and b in Examples 1 and 2. Was inferior.
- the phenol resin d of the comparative example 2 has many acetone melt
- the liquid resol-type phenolic resin of the present invention has excellent properties of phenolic resins such as curability and is capable of obtaining a molded product having excellent flexibility, and is particularly suitable for use as a friction material. It is something that can be done.
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Abstract
Description
本実施形態に係る液状レゾール型フェノール樹脂は、すべてのフェノール構造単位の少なくとも1つ以上のメタ位に、炭素数10以上の直鎖不飽和炭化水素基が結合していることを特徴とする。こうすることで、フェノール樹脂の特性である硬化性という観点において優れており、かつ柔軟性に優れた湿式ペーパー摩擦材を得るために好適な液状レゾール型フェノール樹脂を得ることができる。
まず、フェノール類(A)における炭素数10以上の直鎖不飽和炭化水素基の炭素-炭素多重結合に、酸触媒から供給されたプロトン(H+)が付加してカルボカチオンが生成する。次に、生成したカルボカチオンと、その他のフェノール類(A)分子におけるベンゼン環との間で置換反応が生じ、フェノール類化合物(B)は生成しているものと考えられる。なお、上記その他のフェノール類(A)分子に結合している炭素数10以上の直鎖不飽和炭化水素基についても、別のフェノール類(A)分子におけるベンゼン環との間で置換反応が生じているものと考えられる。このようにして生成したフェノール類化合物(B)と、アルデヒド類(C)と、を塩基性触媒下で反応させることにより、本実施形態に係る液状レゾール型フェノール樹脂を得ることができる。
本実施形態に係る湿式ペーパー摩擦材は、上記液状レゾール型フェノール樹脂を用いてなるものである。こうすることで、フェノール樹脂の特性である耐熱性や硬化性という観点において優れており、さらに柔軟性に優れた湿式ペーパー摩擦材を実現することができる。
以下、参考形態の例を付記する。
[1]すべてのフェノール骨格の、少なくとも1つ以上のメタ位にC10以上の直鎖不飽和炭化水素基を有することを特徴とする液状レゾール型フェノール樹脂。
[2]少なくとも1つ以上のメタ位にC10以上の直鎖不飽和炭化水素基を有するフェノール類(A)を酸触媒下で反応させて得られるフェノール類化合物(B)と、アルデヒド類(C)とを塩基性触媒下で反応させて得られる、[1]に記載の液状レゾール型フェノール樹脂。
[3]少なくとも1つ以上のメタ位にC10以上の直鎖不飽和炭化水素基を有するフェノール類(A)と、アルデヒド類(C)とを塩基性触媒下で反応させて得られる、[1]に記載の液状レゾール型フェノール樹脂。
[4]前記フェノール類(A)がカルダノール、カルドール、2-メチルカルドールの中から選ばれる少なくとも一つ以上のフェノール類である、[2]又は[3]に記載の液状レゾール型フェノール樹脂。
[5]含浸用途に用いられるものである、[1]ないし[4]のいずれか一つに記載の液状レゾール型フェノール樹脂。
[6]湿式ペーパー摩擦材用途に用いられるものである、[1]ないし[5]のいずれか一つに記載の液状レゾール型フェノール樹脂。
[7][6]に記載の液状レゾール型フェノール樹脂を用いてなることを特徴とする湿式ペーパー摩擦材。
(実施例1)
撹拌装置、還流冷却器及び温度計を備えた反応装置に、カルダノール1000部、パラトルエンスルホン酸15部を添加し、140℃に加熱昇温させ1時間撹拌しながら反応させた。これに、37%ホルマリン水溶液180部(カルダノール反応物とのモル比=0.8)、トリエチルアミン5部、50%水酸化ナトリウム水溶液10部を添加し、60℃で2時間撹拌しながら反応させた。その後、91kPaの減圧下で脱水を行いながら、系内の温度が65℃に達したところでトルエン280部、メタノール670部を加えて溶解・冷却した。こうすることで、不揮発分45%の液状レゾール型フェノール樹脂aを、2100部得た。
撹拌装置、還流冷却器及び温度計を備えた反応装置に、カルダノール1000部、37%ホルマリン水溶液180部(カルダノールとのモル比=0.8)、トリエチルアミン5部、50%水酸化ナトリウム水溶液10部を添加し、60℃で2時間撹拌しながら反応させた。その後91kPaの減圧下で脱水を行いながら、系内の温度が65℃に達したところでトルエン280部、メタノール670部を加えて溶解・冷却した。こうすることで、不揮発分45%の液状レゾール型フェノール樹脂bを、2100部得た。
撹拌装置、還流冷却器及び温度計を備えた反応装置に、フェノール1000部、37%ホルマリン水溶液740部(フェノールとのモル比=1.0)、50%水酸化ナトリウム水溶液20部を添加し、100℃で30分間撹拌しながら反応させた。その後91kPaの減圧下で脱水を行いながら、系内の温度が65℃に達したところでメタノール1000部を加えて溶解・冷却した。こうすることで、不揮発分45%の液状レゾール型フェノール樹脂cを、2100部得た。
撹拌装置、還流冷却器及び温度計を備えた反応装置に、フェノール1000部、桐油540部、パラトルエンスルホン酸1部を添加し、60℃に加熱昇温させ30分間撹拌しながら反応させた。これに、37%ホルマリン水溶液770部(フェノールとのモル比=1.2)、トリエタノールアミン1部、25%アンモニア水溶液20部を添加し、100℃で2時間撹拌しながら反応させた。その後68cmHgの減圧下で脱水を行いながら、系内の温度が70℃に達したところでトルエン280部、メタノール670部を加えて溶解・冷却した。こうすることで、不揮発分45%の液状レゾール型フェノール樹脂dを、2100部得た。
実施例および比較例で得られた液状レゾール型フェノール樹脂a~dを用いて、含浸紙を作製した。基材には市販の濾紙(120mm×10mm×厚さ1mm)を使用した。
引張り強さ:得られた試験片について、JIS P 8113に準じて測定した。なお、単位は、MPaである。測定条件は、上記方法で作製した試験片を、精密万能試験機AG-IS 5kN(島津製作所社製)を用いて、常温常圧下、1mm/minの試験速度で実施した。
Claims (9)
- すべてのフェノール構造単位の少なくとも1つ以上のメタ位に、炭素数10以上の直鎖不飽和炭化水素基が結合している液状レゾール型フェノール樹脂。
- 少なくとも1つ以上のメタ位に炭素数10以上の直鎖不飽和炭化水素基が結合しているフェノール類(A)を、反応させて得られる請求項1に記載の液状レゾール型フェノール樹脂。
- フェノール類(A)を、酸触媒存在下、反応させて得られるフェノール類化合物(B)と、アルデヒド類(C)と、を塩基性触媒下で反応させて得られる、請求項1乃至3のいずれか一項に記載の液状レゾール型フェノール樹脂。
- フェノール類(A)と、アルデヒド類(C)と、を塩基性触媒下で反応させて得られる、請求項1乃至3のいずれか一項に記載の液状レゾール型フェノール樹脂。
- 前記フェノール類(A)が、カルダノール、カルドール、2-メチルカルドールの中からなる群より選択される少なくとも一つ以上のフェノール類である、請求項2乃至6のいずれか一項に記載の液状レゾール型フェノール樹脂。
- 基材に含浸させて用いる、請求項1乃至7のいずれか一項に記載の液状レゾール型フェノール樹脂。
- 請求項1乃至8のいずれか一項に記載の液状レゾール型フェノール樹脂を用いてなることを特徴とする湿式ペーパー摩擦材。
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CN201380028050.4A CN104364283A (zh) | 2012-05-31 | 2013-05-29 | 液态甲阶型酚醛树脂和湿式纸摩擦材料 |
EP13797608.0A EP2857426A1 (en) | 2012-05-31 | 2013-05-29 | Liquid phenolic resole resin and wet paper friction material |
CA2869290A CA2869290A1 (en) | 2012-05-31 | 2013-05-29 | Liquid resol-type phenolic resin and wet paper friction material |
KR20147030868A KR20150023240A (ko) | 2012-05-31 | 2013-05-29 | 액상 레졸형 페놀 수지 및 습식 페이퍼 마찰재 |
US14/391,256 US9163106B2 (en) | 2012-05-31 | 2013-05-29 | Liquid resol-type phenolic resin and wet paper friction material |
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CN106866906B (zh) * | 2017-01-24 | 2019-04-12 | 美国保利瑞公司 | 一种植物多烯双酚摩擦粉的制备方法 |
EP4053240A4 (en) * | 2019-11-01 | 2023-11-29 | Sumitomo Bakelite Co., Ltd. | ADHESIVE AGENT COMPOSITION FOR WET TYPE FRICTION ELEMENT |
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CN100463949C (zh) * | 2007-02-14 | 2009-02-25 | 西北工业大学 | 柔性纸基摩擦材料 |
CN101805589B (zh) * | 2010-02-09 | 2013-03-20 | 陕西科技大学 | 一种高性能环保纸基摩擦材料原纸及摩擦片的制作方法 |
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2013
- 2013-05-29 US US14/391,256 patent/US9163106B2/en not_active Expired - Fee Related
- 2013-05-29 CA CA2869290A patent/CA2869290A1/en not_active Abandoned
- 2013-05-29 EP EP13797608.0A patent/EP2857426A1/en not_active Withdrawn
- 2013-05-29 CN CN201380028050.4A patent/CN104364283A/zh active Pending
- 2013-05-29 JP JP2014518285A patent/JP6225900B2/ja not_active Expired - Fee Related
- 2013-05-29 KR KR20147030868A patent/KR20150023240A/ko not_active Application Discontinuation
- 2013-05-29 WO PCT/JP2013/003385 patent/WO2013179660A1/ja active Application Filing
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JPS4829530B1 (ja) * | 1969-04-02 | 1973-09-11 | ||
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2017068866A1 (ja) * | 2015-10-21 | 2017-04-27 | 住友ベークライト株式会社 | 液状レゾール型フェノール樹脂、液状レゾール型フェノール樹脂の製造方法、および物品 |
JP2017078127A (ja) * | 2015-10-21 | 2017-04-27 | 住友ベークライト株式会社 | 液状レゾール型フェノール樹脂、液状レゾール型フェノール樹脂の製造方法、および物品 |
Also Published As
Publication number | Publication date |
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EP2857426A1 (en) | 2015-04-08 |
CN104364283A (zh) | 2015-02-18 |
CA2869290A1 (en) | 2013-12-05 |
JPWO2013179660A1 (ja) | 2016-01-18 |
JP6225900B2 (ja) | 2017-11-08 |
US9163106B2 (en) | 2015-10-20 |
KR20150023240A (ko) | 2015-03-05 |
US20150065756A1 (en) | 2015-03-05 |
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