CA2438191A1 - Thermosetting resin-fiber composite and method and apparatus for the manufacture thereof - Google Patents
Thermosetting resin-fiber composite and method and apparatus for the manufacture thereof Download PDFInfo
- Publication number
- CA2438191A1 CA2438191A1 CA002438191A CA2438191A CA2438191A1 CA 2438191 A1 CA2438191 A1 CA 2438191A1 CA 002438191 A CA002438191 A CA 002438191A CA 2438191 A CA2438191 A CA 2438191A CA 2438191 A1 CA2438191 A1 CA 2438191A1
- Authority
- CA
- Canada
- Prior art keywords
- resin
- thermosetting resin
- curing agent
- phenol
- thermosetting
- 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.)
- Abandoned
Links
- 229920001187 thermosetting polymer Polymers 0.000 title claims abstract description 48
- 238000000034 method Methods 0.000 title claims abstract description 34
- 239000002131 composite material Substances 0.000 title claims abstract description 9
- 239000000835 fiber Substances 0.000 title claims description 31
- 238000004519 manufacturing process Methods 0.000 title abstract description 8
- 229920005989 resin Polymers 0.000 claims abstract description 65
- 239000011347 resin Substances 0.000 claims abstract description 65
- 229920003986 novolac Polymers 0.000 claims abstract description 64
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 48
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 39
- 238000002844 melting Methods 0.000 claims abstract description 25
- 230000008018 melting Effects 0.000 claims abstract description 25
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 17
- 239000011342 resin composition Substances 0.000 claims abstract description 16
- 150000001299 aldehydes Chemical class 0.000 claims abstract description 12
- 230000001588 bifunctional effect Effects 0.000 claims abstract description 12
- 238000010438 heat treatment Methods 0.000 claims abstract description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000007787 solid Substances 0.000 claims abstract description 4
- 238000009833 condensation Methods 0.000 claims abstract description 3
- 230000005494 condensation Effects 0.000 claims abstract description 3
- 229920005992 thermoplastic resin Polymers 0.000 claims abstract 12
- 239000000758 substrate Substances 0.000 claims abstract 7
- 239000002245 particle Substances 0.000 claims description 35
- 229920001568 phenolic resin Polymers 0.000 claims description 26
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 claims description 24
- 239000000463 material Substances 0.000 claims description 20
- 230000008569 process Effects 0.000 claims description 15
- 239000005011 phenolic resin Substances 0.000 claims description 14
- 229920002647 polyamide Polymers 0.000 claims description 13
- 239000003365 glass fiber Substances 0.000 claims description 12
- 239000000843 powder Substances 0.000 claims description 12
- 239000003431 cross linking reagent Substances 0.000 claims description 9
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical group C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 claims description 8
- 239000008393 encapsulating agent Substances 0.000 claims description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical class O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 6
- 238000004132 cross linking Methods 0.000 claims description 6
- 239000006185 dispersion Substances 0.000 claims description 6
- -1 propylene-ethylene-butylene Chemical group 0.000 claims description 6
- 239000002002 slurry Substances 0.000 claims description 5
- 239000011248 coating agent Substances 0.000 claims description 4
- 238000000576 coating method Methods 0.000 claims description 4
- 239000000839 emulsion Substances 0.000 claims description 4
- 239000004312 hexamethylene tetramine Substances 0.000 claims description 4
- 235000010299 hexamethylene tetramine Nutrition 0.000 claims description 4
- 239000012784 inorganic fiber Substances 0.000 claims description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 3
- 239000005977 Ethylene Substances 0.000 claims description 3
- 229920000877 Melamine resin Polymers 0.000 claims description 3
- 229930040373 Paraformaldehyde Natural products 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 239000003822 epoxy resin Substances 0.000 claims description 3
- 239000011521 glass Substances 0.000 claims description 3
- 239000006060 molten glass Substances 0.000 claims description 3
- 229920002866 paraformaldehyde Polymers 0.000 claims description 3
- 229920000647 polyepoxide Polymers 0.000 claims description 3
- 239000004645 polyester resin Substances 0.000 claims description 3
- 229920001225 polyester resin Polymers 0.000 claims description 3
- XGJZQNMUVTZITK-UHFFFAOYSA-N 2-n,2-n,4-n,4-n,6-n,6-n-hexamethoxy-1,3,5-triazine-2,4,6-triamine Chemical compound CON(OC)C1=NC(N(OC)OC)=NC(N(OC)OC)=N1 XGJZQNMUVTZITK-UHFFFAOYSA-N 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 239000011152 fibreglass Substances 0.000 claims description 2
- 239000011159 matrix material Substances 0.000 claims description 2
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 claims description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims 2
- XUMBMVFBXHLACL-UHFFFAOYSA-N Melanin Chemical compound O=C1C(=O)C(C2=CNC3=C(C(C(=O)C4=C32)=O)C)=C2C4=CNC2=C1C XUMBMVFBXHLACL-UHFFFAOYSA-N 0.000 claims 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims 2
- 229920001400 block copolymer Polymers 0.000 claims 2
- 239000003094 microcapsule Substances 0.000 claims 2
- 239000004634 thermosetting polymer Substances 0.000 claims 2
- 239000004593 Epoxy Substances 0.000 claims 1
- IWYRWIUNAVNFPE-UHFFFAOYSA-N Glycidaldehyde Chemical compound O=CC1CO1 IWYRWIUNAVNFPE-UHFFFAOYSA-N 0.000 claims 1
- 239000004640 Melamine resin Substances 0.000 claims 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims 1
- 229920006243 acrylic copolymer Polymers 0.000 claims 1
- 230000003213 activating effect Effects 0.000 claims 1
- 229910010272 inorganic material Inorganic materials 0.000 claims 1
- 239000011147 inorganic material Substances 0.000 claims 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
- 239000011134 resol-type phenolic resin Substances 0.000 claims 1
- 229920001169 thermoplastic Polymers 0.000 claims 1
- 239000004416 thermosoftening plastic Substances 0.000 claims 1
- 238000010276 construction Methods 0.000 abstract description 4
- 239000000945 filler Substances 0.000 abstract description 2
- 239000012744 reinforcing agent Substances 0.000 abstract description 2
- 230000003014 reinforcing effect Effects 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 16
- 239000004952 Polyamide Substances 0.000 description 12
- 239000000203 mixture Substances 0.000 description 10
- 150000002989 phenols Chemical class 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 239000004970 Chain extender Substances 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 8
- 230000009477 glass transition Effects 0.000 description 7
- 239000011230 binding agent Substances 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 125000005843 halogen group Chemical group 0.000 description 5
- 238000005054 agglomeration Methods 0.000 description 4
- 230000002776 aggregation Effects 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 210000002268 wool Anatomy 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 229910021485 fumed silica Inorganic materials 0.000 description 3
- 229960004011 methenamine Drugs 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- QWBBPBRQALCEIZ-UHFFFAOYSA-N 2,3-dimethylphenol Chemical compound CC1=CC=CC(O)=C1C QWBBPBRQALCEIZ-UHFFFAOYSA-N 0.000 description 2
- AQFCDVGUEQOTAC-UHFFFAOYSA-N 2,5-diethylphenol Chemical compound CCC1=CC=C(CC)C(O)=C1 AQFCDVGUEQOTAC-UHFFFAOYSA-N 0.000 description 2
- VFNUNYPYULIJSN-UHFFFAOYSA-N 2,5-diisopropylphenol Chemical compound CC(C)C1=CC=C(C(C)C)C(O)=C1 VFNUNYPYULIJSN-UHFFFAOYSA-N 0.000 description 2
- NKTOLZVEWDHZMU-UHFFFAOYSA-N 2,5-xylenol Chemical compound CC1=CC=C(C)C(O)=C1 NKTOLZVEWDHZMU-UHFFFAOYSA-N 0.000 description 2
- SEAZSNZFNABEMJ-UHFFFAOYSA-N 3,4-diethylphenol Chemical compound CCC1=CC=C(O)C=C1CC SEAZSNZFNABEMJ-UHFFFAOYSA-N 0.000 description 2
- YCOXTKKNXUZSKD-UHFFFAOYSA-N 3,4-xylenol Chemical compound CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 2
- LPCJHUPMQKSPDC-UHFFFAOYSA-N 3,5-diethylphenol Chemical compound CCC1=CC(O)=CC(CC)=C1 LPCJHUPMQKSPDC-UHFFFAOYSA-N 0.000 description 2
- TUAMRELNJMMDMT-UHFFFAOYSA-N 3,5-xylenol Chemical compound CC1=CC(C)=CC(O)=C1 TUAMRELNJMMDMT-UHFFFAOYSA-N 0.000 description 2
- HMNKTRSOROOSPP-UHFFFAOYSA-N 3-Ethylphenol Chemical compound CCC1=CC=CC(O)=C1 HMNKTRSOROOSPP-UHFFFAOYSA-N 0.000 description 2
- VLJSLTNSFSOYQR-UHFFFAOYSA-N 3-propan-2-ylphenol Chemical compound CC(C)C1=CC=CC(O)=C1 VLJSLTNSFSOYQR-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 125000001118 alkylidene group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 150000001555 benzenes Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000012634 fragment Substances 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- IXQGCWUGDFDQMF-UHFFFAOYSA-N o-Hydroxyethylbenzene Natural products CCC1=CC=CC=C1O IXQGCWUGDFDQMF-UHFFFAOYSA-N 0.000 description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- GJYCVCVHRSWLNY-UHFFFAOYSA-N ortho-butylphenol Natural products CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- NWQWQKUXRJYXFH-UHFFFAOYSA-N 2,2-Dichloroacetaldehyde Chemical compound ClC(Cl)C=O NWQWQKUXRJYXFH-UHFFFAOYSA-N 0.000 description 1
- ZEFOXNBIQIPHOP-UHFFFAOYSA-N 2,3-di(propan-2-yl)phenol Chemical compound CC(C)C1=CC=CC(O)=C1C(C)C ZEFOXNBIQIPHOP-UHFFFAOYSA-N 0.000 description 1
- UMPSXRYVXUPCOS-UHFFFAOYSA-N 2,3-dichlorophenol Chemical compound OC1=CC=CC(Cl)=C1Cl UMPSXRYVXUPCOS-UHFFFAOYSA-N 0.000 description 1
- RLEWTHFVGOXXTN-UHFFFAOYSA-N 2,3-diethylphenol Chemical compound CCC1=CC=CC(O)=C1CC RLEWTHFVGOXXTN-UHFFFAOYSA-N 0.000 description 1
- RANCECPPZPIPNO-UHFFFAOYSA-N 2,5-dichlorophenol Chemical compound OC1=CC(Cl)=CC=C1Cl RANCECPPZPIPNO-UHFFFAOYSA-N 0.000 description 1
- VADKRMSMGWJZCF-UHFFFAOYSA-N 2-bromophenol Chemical compound OC1=CC=CC=C1Br VADKRMSMGWJZCF-UHFFFAOYSA-N 0.000 description 1
- QSKPIOLLBIHNAC-UHFFFAOYSA-N 2-chloro-acetaldehyde Chemical compound ClCC=O QSKPIOLLBIHNAC-UHFFFAOYSA-N 0.000 description 1
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 1
- HFHFGHLXUCOHLN-UHFFFAOYSA-N 2-fluorophenol Chemical compound OC1=CC=CC=C1F HFHFGHLXUCOHLN-UHFFFAOYSA-N 0.000 description 1
- FIWYWGLEPWBBQU-UHFFFAOYSA-N 2-heptylphenol Chemical compound CCCCCCCC1=CC=CC=C1O FIWYWGLEPWBBQU-UHFFFAOYSA-N 0.000 description 1
- ABMULKFGWTYIIK-UHFFFAOYSA-N 2-hexylphenol Chemical compound CCCCCCC1=CC=CC=C1O ABMULKFGWTYIIK-UHFFFAOYSA-N 0.000 description 1
- CRBJBYGJVIBWIY-UHFFFAOYSA-N 2-isopropylphenol Chemical compound CC(C)C1=CC=CC=C1O CRBJBYGJVIBWIY-UHFFFAOYSA-N 0.000 description 1
- RDCHMDPGLCHQQM-UHFFFAOYSA-N 2-methyl-3-phenylphenol Chemical compound CC1=C(O)C=CC=C1C1=CC=CC=C1 RDCHMDPGLCHQQM-UHFFFAOYSA-N 0.000 description 1
- CAPGYRYSLXORFK-UHFFFAOYSA-N 2-methyl-5-phenylphenol Chemical compound C1=C(O)C(C)=CC=C1C1=CC=CC=C1 CAPGYRYSLXORFK-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
- ROMXEVFSCNLHAB-UHFFFAOYSA-N 2-pentan-2-ylphenol Chemical compound CCCC(C)C1=CC=CC=C1O ROMXEVFSCNLHAB-UHFFFAOYSA-N 0.000 description 1
- LCHYEKKJCUJAKN-UHFFFAOYSA-N 2-propylphenol Chemical compound CCCC1=CC=CC=C1O LCHYEKKJCUJAKN-UHFFFAOYSA-N 0.000 description 1
- NGFPWHGISWUQOI-UHFFFAOYSA-N 2-sec-butylphenol Chemical compound CCC(C)C1=CC=CC=C1O NGFPWHGISWUQOI-UHFFFAOYSA-N 0.000 description 1
- WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 description 1
- WDNBURPWRNALGP-UHFFFAOYSA-N 3,4-Dichlorophenol Chemical compound OC1=CC=C(Cl)C(Cl)=C1 WDNBURPWRNALGP-UHFFFAOYSA-N 0.000 description 1
- VTJCIWXYZXSECW-UHFFFAOYSA-N 3,4-di(propan-2-yl)phenol Chemical compound CC(C)C1=CC=C(O)C=C1C(C)C VTJCIWXYZXSECW-UHFFFAOYSA-N 0.000 description 1
- YNLSUGSZSCLCRF-UHFFFAOYSA-N 3,5-bis(2-methylbutan-2-yl)phenol Chemical compound CCC(C)(C)C1=CC(O)=CC(C(C)(C)CC)=C1 YNLSUGSZSCLCRF-UHFFFAOYSA-N 0.000 description 1
- PFBHMJJMZWUEAI-UHFFFAOYSA-N 3,5-di(butan-2-yl)phenol Chemical compound CCC(C)C1=CC(O)=CC(C(C)CC)=C1 PFBHMJJMZWUEAI-UHFFFAOYSA-N 0.000 description 1
- GIGTVUJRBGEYBM-UHFFFAOYSA-N 3,5-di(pentan-2-yl)phenol Chemical compound CCCC(C)C1=CC(O)=CC(C(C)CCC)=C1 GIGTVUJRBGEYBM-UHFFFAOYSA-N 0.000 description 1
- YYOQJBLGFMMRLJ-UHFFFAOYSA-N 3,5-di(propan-2-yl)phenol Chemical compound CC(C)C1=CC(O)=CC(C(C)C)=C1 YYOQJBLGFMMRLJ-UHFFFAOYSA-N 0.000 description 1
- PZFMWYNHJFZBPO-UHFFFAOYSA-N 3,5-dibromophenol Chemical compound OC1=CC(Br)=CC(Br)=C1 PZFMWYNHJFZBPO-UHFFFAOYSA-N 0.000 description 1
- VPOMSPZBQMDLTM-UHFFFAOYSA-N 3,5-dichlorophenol Chemical compound OC1=CC(Cl)=CC(Cl)=C1 VPOMSPZBQMDLTM-UHFFFAOYSA-N 0.000 description 1
- HJSSBIMVTMYKPD-UHFFFAOYSA-N 3,5-difluorophenol Chemical compound OC1=CC(F)=CC(F)=C1 HJSSBIMVTMYKPD-UHFFFAOYSA-N 0.000 description 1
- QKBSGJWVWWLQNQ-UHFFFAOYSA-N 3,5-diheptylphenol Chemical compound CCCCCCCC1=CC(O)=CC(CCCCCCC)=C1 QKBSGJWVWWLQNQ-UHFFFAOYSA-N 0.000 description 1
- ONDAPBYYWJRWEN-UHFFFAOYSA-N 3,5-dihexylphenol Chemical compound CCCCCCC1=CC(O)=CC(CCCCCC)=C1 ONDAPBYYWJRWEN-UHFFFAOYSA-N 0.000 description 1
- KYRNAIDRKAWDLJ-UHFFFAOYSA-N 3,5-diiodophenol Chemical compound OC1=CC(I)=CC(I)=C1 KYRNAIDRKAWDLJ-UHFFFAOYSA-N 0.000 description 1
- MFQKPJOZPDGWLO-UHFFFAOYSA-N 3,5-dioctylphenol Chemical compound CCCCCCCCC1=CC(O)=CC(CCCCCCCC)=C1 MFQKPJOZPDGWLO-UHFFFAOYSA-N 0.000 description 1
- ZDWSNKPLZUXBPE-UHFFFAOYSA-N 3,5-ditert-butylphenol Chemical compound CC(C)(C)C1=CC(O)=CC(C(C)(C)C)=C1 ZDWSNKPLZUXBPE-UHFFFAOYSA-N 0.000 description 1
- ZVUDLZCSBFUWEO-UHFFFAOYSA-N 3-(2-methylbutan-2-yl)phenol Chemical compound CCC(C)(C)C1=CC=CC(O)=C1 ZVUDLZCSBFUWEO-UHFFFAOYSA-N 0.000 description 1
- MNOJRWOWILAHAV-UHFFFAOYSA-N 3-bromophenol Chemical compound OC1=CC=CC(Br)=C1 MNOJRWOWILAHAV-UHFFFAOYSA-N 0.000 description 1
- NBYBZLCUXTUWBA-UHFFFAOYSA-N 3-butan-2-ylphenol Chemical compound CCC(C)C1=CC=CC(O)=C1 NBYBZLCUXTUWBA-UHFFFAOYSA-N 0.000 description 1
- MQSXUKPGWMJYBT-UHFFFAOYSA-N 3-butylphenol Chemical compound CCCCC1=CC=CC(O)=C1 MQSXUKPGWMJYBT-UHFFFAOYSA-N 0.000 description 1
- HORNXRXVQWOLPJ-UHFFFAOYSA-N 3-chlorophenol Chemical compound OC1=CC=CC(Cl)=C1 HORNXRXVQWOLPJ-UHFFFAOYSA-N 0.000 description 1
- SJTBRFHBXDZMPS-UHFFFAOYSA-N 3-fluorophenol Chemical compound OC1=CC=CC(F)=C1 SJTBRFHBXDZMPS-UHFFFAOYSA-N 0.000 description 1
- KCDFHCLOYLFCDE-UHFFFAOYSA-N 3-heptylphenol Chemical compound CCCCCCCC1=CC=CC(O)=C1 KCDFHCLOYLFCDE-UHFFFAOYSA-N 0.000 description 1
- CRIQSWIRYKZJAV-UHFFFAOYSA-N 3-hexylphenol Chemical compound CCCCCCC1=CC=CC(O)=C1 CRIQSWIRYKZJAV-UHFFFAOYSA-N 0.000 description 1
- BHUODJHOUAFKAS-UHFFFAOYSA-N 3-methyl-4-phenylphenol Chemical compound CC1=CC(O)=CC=C1C1=CC=CC=C1 BHUODJHOUAFKAS-UHFFFAOYSA-N 0.000 description 1
- QEVPNCHYTKOQMP-UHFFFAOYSA-N 3-octylphenol Chemical compound CCCCCCCCC1=CC=CC(O)=C1 QEVPNCHYTKOQMP-UHFFFAOYSA-N 0.000 description 1
- MPUFUPAZSMMGBP-UHFFFAOYSA-N 3-pentan-2-ylphenol Chemical compound CCCC(C)C1=CC=CC(O)=C1 MPUFUPAZSMMGBP-UHFFFAOYSA-N 0.000 description 1
- MPWGZBWDLMDIHO-UHFFFAOYSA-N 3-propylphenol Chemical compound CCCC1=CC=CC(O)=C1 MPWGZBWDLMDIHO-UHFFFAOYSA-N 0.000 description 1
- CYEKUDPFXBLGHH-UHFFFAOYSA-N 3-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC(O)=C1 CYEKUDPFXBLGHH-UHFFFAOYSA-N 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 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
- 239000007864 aqueous solution Substances 0.000 description 1
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-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
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 239000011491 glass wool Substances 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000011490 mineral wool Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 239000012768 molten material Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- NRZWYNLTFLDQQX-UHFFFAOYSA-N p-tert-Amylphenol Chemical compound CCC(C)(C)C1=CC=C(O)C=C1 NRZWYNLTFLDQQX-UHFFFAOYSA-N 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000012262 resinous product Substances 0.000 description 1
- 229920003987 resole Polymers 0.000 description 1
- 238000005245 sintering Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229940029273 trichloroacetaldehyde Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
- C08L61/04—Condensation polymers of aldehydes or ketones with phenols only
- C08L61/06—Condensation polymers of aldehydes or ketones with phenols only 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
- C08G8/10—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ with phenol
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Reinforced Plastic Materials (AREA)
- Building Environments (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITMI2001A000236 | 2001-02-07 | ||
| IT2001MI000236A ITMI20010236A1 (it) | 2001-02-07 | 2001-02-07 | Procedimento per la realizzazione di manufatti termo e fonoisolanti per l'edilizia e per l'industria impianto per la realizzazione di questo |
| PCT/US2002/003295 WO2002070599A2 (en) | 2001-02-07 | 2002-02-07 | Thermosetting resin-fiber composite and method and apparatus for the manufacture thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2438191A1 true CA2438191A1 (en) | 2002-09-12 |
Family
ID=11446770
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002438191A Abandoned CA2438191A1 (en) | 2001-02-07 | 2002-02-07 | Thermosetting resin-fiber composite and method and apparatus for the manufacture thereof |
Country Status (10)
| Country | Link |
|---|---|
| EP (1) | EP1358214A4 (it) |
| KR (1) | KR20030026238A (it) |
| CN (1) | CN1461311A (it) |
| CA (1) | CA2438191A1 (it) |
| EA (1) | EA005231B1 (it) |
| HU (1) | HUP0302209A2 (it) |
| IT (1) | ITMI20010236A1 (it) |
| LV (1) | LV13149B (it) |
| PL (1) | PL368324A1 (it) |
| WO (1) | WO2002070599A2 (it) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100351312C (zh) * | 2004-12-31 | 2007-11-28 | 中国兵器工业集团第五三研究所 | 一种纤维填充酚醛泡沫塑料 |
| KR101149276B1 (ko) * | 2005-12-12 | 2012-05-25 | 주식회사 한국화이바 | 절단 또는 연속 유리섬유 스트랜드 매트가 보강된 열가소성복합재료의 제조방법 및 제조장치 |
| KR100758748B1 (ko) * | 2005-12-30 | 2007-09-14 | 주식회사 동부하이텍 | 내화피복 형성용 조성물 |
| CN115625897B (zh) * | 2022-12-12 | 2023-03-28 | 北京玻钢院复合材料有限公司 | 一种增韧低密度热熔酚醛树脂预浸料、复合材料及制备方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4230471A (en) * | 1973-03-30 | 1980-10-28 | Saint-Gobain Industries | Suppression of pollution in mineral fiber manufacture |
| US4173443A (en) * | 1977-06-01 | 1979-11-06 | Celanese Corporation | Spray spinning nozzle having convergent gaseous jets |
| US4940852A (en) * | 1986-07-16 | 1990-07-10 | Milton P. Chernack | Pressure sensitive adhesive composition |
| US4840832A (en) * | 1987-06-23 | 1989-06-20 | Collins & Aikman Corporation | Molded automobile headliner |
| JPH06145420A (ja) * | 1992-11-09 | 1994-05-24 | Sumitomo Bakelite Co Ltd | フェノール樹脂成形材料 |
| TW305860B (it) * | 1994-03-15 | 1997-05-21 | Toray Industries | |
| JPH07292217A (ja) * | 1994-04-27 | 1995-11-07 | Sumitomo Bakelite Co Ltd | フェノール樹脂組成物 |
| US6114491A (en) * | 1997-12-19 | 2000-09-05 | Georgia-Pacific Resins, Inc. | Cyclic urea-formaldehyde prepolymer for use in phenol-formaldehyde and melamine-formaldehyde resin-based binders |
-
2001
- 2001-02-07 IT IT2001MI000236A patent/ITMI20010236A1/it unknown
-
2002
- 2002-02-07 EA EA200300841A patent/EA005231B1/ru not_active IP Right Cessation
- 2002-02-07 PL PL02368324A patent/PL368324A1/xx unknown
- 2002-02-07 HU HU0302209A patent/HUP0302209A2/hu unknown
- 2002-02-07 KR KR1020027013416A patent/KR20030026238A/ko not_active Application Discontinuation
- 2002-02-07 WO PCT/US2002/003295 patent/WO2002070599A2/en not_active Application Discontinuation
- 2002-02-07 CN CN02801144A patent/CN1461311A/zh active Pending
- 2002-02-07 CA CA002438191A patent/CA2438191A1/en not_active Abandoned
- 2002-02-07 EP EP02709345A patent/EP1358214A4/en not_active Withdrawn
-
2003
- 2003-08-29 LV LVP-03-95A patent/LV13149B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL368324A1 (en) | 2005-03-21 |
| EA200300841A1 (ru) | 2004-04-29 |
| KR20030026238A (ko) | 2003-03-31 |
| LV13149B (en) | 2004-07-20 |
| WO2002070599A2 (en) | 2002-09-12 |
| WO2002070599A9 (en) | 2004-07-22 |
| WO2002070599A8 (en) | 2004-06-03 |
| EA005231B1 (ru) | 2004-12-30 |
| CN1461311A (zh) | 2003-12-10 |
| EP1358214A4 (en) | 2004-08-18 |
| EP1358214A2 (en) | 2003-11-05 |
| ITMI20010236A1 (it) | 2002-08-07 |
| HUP0302209A2 (hu) | 2003-10-28 |
| WO2002070599A3 (en) | 2002-11-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued | ||
| FZDE | Discontinued |
Effective date: 20050207 |