CA1173580A - Methode pour preparer une resine d'aldehyde phenolique, et compositon de resine pour systeme adhesif applique sur des fibres de verre - Google Patents
Methode pour preparer une resine d'aldehyde phenolique, et compositon de resine pour systeme adhesif applique sur des fibres de verreInfo
- Publication number
- CA1173580A CA1173580A CA000368266A CA368266A CA1173580A CA 1173580 A CA1173580 A CA 1173580A CA 000368266 A CA000368266 A CA 000368266A CA 368266 A CA368266 A CA 368266A CA 1173580 A CA1173580 A CA 1173580A
- Authority
- CA
- Canada
- Prior art keywords
- resorcinol
- range
- aldehyde
- resin
- mixture
- 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
- 239000000853 adhesive Substances 0.000 title claims abstract description 83
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 83
- 239000003365 glass fiber Substances 0.000 title claims abstract description 69
- 238000000034 method Methods 0.000 title claims abstract description 45
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 title claims abstract description 37
- RCHKEJKUUXXBSM-UHFFFAOYSA-N n-benzyl-2-(3-formylindol-1-yl)acetamide Chemical compound C12=CC=CC=C2C(C=O)=CN1CC(=O)NCC1=CC=CC=C1 RCHKEJKUUXXBSM-UHFFFAOYSA-N 0.000 title claims abstract description 29
- 239000011342 resin composition Substances 0.000 title description 3
- 239000000203 mixture Substances 0.000 claims abstract description 122
- 229920005989 resin Polymers 0.000 claims abstract description 116
- 239000011347 resin Substances 0.000 claims abstract description 116
- 229920001971 elastomer Polymers 0.000 claims abstract description 79
- 239000005060 rubber Substances 0.000 claims abstract description 75
- 229920000126 latex Polymers 0.000 claims abstract description 74
- 238000006243 chemical reaction Methods 0.000 claims abstract description 70
- 150000001299 aldehydes Chemical class 0.000 claims abstract description 54
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 53
- 150000002989 phenols Chemical class 0.000 claims abstract description 52
- 229920000642 polymer Polymers 0.000 claims abstract description 49
- 239000004816 latex Substances 0.000 claims abstract description 44
- 239000000463 material Substances 0.000 claims abstract description 30
- 239000013638 trimer Substances 0.000 claims abstract description 27
- 229920001169 thermoplastic Polymers 0.000 claims abstract description 26
- 239000004416 thermosoftening plastic Substances 0.000 claims abstract description 26
- 238000004132 cross linking Methods 0.000 claims abstract description 23
- 239000000539 dimer Substances 0.000 claims abstract description 16
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 14
- 230000002378 acidificating effect Effects 0.000 claims abstract description 8
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 7
- 150000001412 amines Chemical class 0.000 claims abstract 3
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 189
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical group O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 158
- 239000008199 coating composition Substances 0.000 claims description 45
- 238000000576 coating method Methods 0.000 claims description 28
- 239000011248 coating agent Substances 0.000 claims description 27
- -1 phenol alcohols Chemical class 0.000 claims description 24
- 239000007787 solid Substances 0.000 claims description 23
- 239000000835 fiber Substances 0.000 claims description 22
- 239000007864 aqueous solution Substances 0.000 claims description 18
- 239000003054 catalyst Substances 0.000 claims description 18
- 239000003963 antioxidant agent Substances 0.000 claims description 17
- 230000009975 flexible effect Effects 0.000 claims description 16
- 230000003078 antioxidant effect Effects 0.000 claims description 14
- 239000005062 Polybutadiene Substances 0.000 claims description 12
- 230000015572 biosynthetic process Effects 0.000 claims description 10
- 229920002857 polybutadiene Polymers 0.000 claims description 9
- 239000003377 acid catalyst Substances 0.000 claims description 8
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 8
- 239000011541 reaction mixture Substances 0.000 claims description 8
- 230000032683 aging Effects 0.000 claims description 6
- 229920001897 terpolymer Polymers 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- 239000002585 base Substances 0.000 claims description 4
- QUEICCDHEFTIQD-UHFFFAOYSA-N buta-1,3-diene;2-ethenylpyridine;styrene Chemical compound C=CC=C.C=CC1=CC=CC=C1.C=CC1=CC=CC=N1 QUEICCDHEFTIQD-UHFFFAOYSA-N 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- 229920002959 polymer blend Polymers 0.000 claims description 4
- 239000002174 Styrene-butadiene Substances 0.000 claims description 3
- 239000002270 dispersing agent Substances 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 3
- 229920000728 polyester Polymers 0.000 claims description 3
- 239000003381 stabilizer Substances 0.000 claims description 3
- 229920003048 styrene butadiene rubber Polymers 0.000 claims description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 2
- 150000008041 alkali metal carbonates Chemical class 0.000 claims description 2
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 239000011115 styrene butadiene Substances 0.000 claims description 2
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims 2
- 229910000272 alkali metal oxide Inorganic materials 0.000 claims 2
- 150000001340 alkali metals Chemical class 0.000 claims 2
- KVBYPTUGEKVEIJ-UHFFFAOYSA-N benzene-1,3-diol;formaldehyde Chemical compound O=C.OC1=CC=CC(O)=C1 KVBYPTUGEKVEIJ-UHFFFAOYSA-N 0.000 claims 2
- 229910052791 calcium Inorganic materials 0.000 claims 2
- 239000011575 calcium Substances 0.000 claims 2
- 229910052749 magnesium Inorganic materials 0.000 claims 2
- 239000011777 magnesium Substances 0.000 claims 2
- 230000003014 reinforcing effect Effects 0.000 claims 2
- 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 claims 1
- 239000004952 Polyamide Substances 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 229920002301 cellulose acetate Polymers 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 229910000000 metal hydroxide Inorganic materials 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- QQBPIHBUCMDKFG-UHFFFAOYSA-N phenazopyridine hydrochloride Chemical compound Cl.NC1=NC(N)=CC=C1N=NC1=CC=CC=C1 QQBPIHBUCMDKFG-UHFFFAOYSA-N 0.000 claims 1
- 229920002647 polyamide Polymers 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 1
- 229920002554 vinyl polymer Polymers 0.000 claims 1
- 230000006835 compression Effects 0.000 abstract description 9
- 238000007906 compression Methods 0.000 abstract description 9
- 230000002787 reinforcement Effects 0.000 abstract description 4
- 239000000654 additive Substances 0.000 abstract description 3
- 229960001755 resorcinol Drugs 0.000 description 55
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 46
- 229960004279 formaldehyde Drugs 0.000 description 45
- 235000019256 formaldehyde Nutrition 0.000 description 39
- DGXAGETVRDOQFP-UHFFFAOYSA-N 2,6-dihydroxybenzaldehyde Chemical compound OC1=CC=CC(O)=C1C=O DGXAGETVRDOQFP-UHFFFAOYSA-N 0.000 description 31
- 235000013824 polyphenols Nutrition 0.000 description 28
- 238000012360 testing method Methods 0.000 description 23
- 239000008367 deionised water Substances 0.000 description 15
- 229910021641 deionized water Inorganic materials 0.000 description 15
- 238000007792 addition Methods 0.000 description 14
- 235000006708 antioxidants Nutrition 0.000 description 14
- 239000002253 acid Substances 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 10
- 235000011114 ammonium hydroxide Nutrition 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000908 ammonium hydroxide Substances 0.000 description 9
- 239000006185 dispersion Substances 0.000 description 8
- 238000005755 formation reaction Methods 0.000 description 8
- 239000011521 glass Substances 0.000 description 8
- 238000002156 mixing Methods 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 239000011152 fibreglass Substances 0.000 description 7
- 239000000376 reactant Substances 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 5
- 239000004744 fabric Substances 0.000 description 5
- 230000001965 increasing effect Effects 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 239000012260 resinous material Substances 0.000 description 4
- 238000004513 sizing Methods 0.000 description 4
- 230000035882 stress Effects 0.000 description 4
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-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
- 238000005470 impregnation Methods 0.000 description 3
- 238000011068 loading method Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- 229920001084 poly(chloroprene) Polymers 0.000 description 3
- 229920003987 resole Polymers 0.000 description 3
- 229920003051 synthetic elastomer Polymers 0.000 description 3
- 239000005061 synthetic rubber Substances 0.000 description 3
- 238000007039 two-step reaction Methods 0.000 description 3
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 238000005844 autocatalytic reaction Methods 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 239000003518 caustics Substances 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- MIHINWMALJZIBX-UHFFFAOYSA-N cyclohexa-2,4-dien-1-ol Chemical compound OC1CC=CC=C1 MIHINWMALJZIBX-UHFFFAOYSA-N 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 239000000806 elastomer Substances 0.000 description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- 229920001778 nylon Polymers 0.000 description 2
- OIPPWFOQEKKFEE-UHFFFAOYSA-N orcinol Chemical compound CC1=CC(O)=CC(O)=C1 OIPPWFOQEKKFEE-UHFFFAOYSA-N 0.000 description 2
- 229920001568 phenolic resin Polymers 0.000 description 2
- 239000005011 phenolic resin Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000012779 reinforcing material Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 229920005992 thermoplastic resin Polymers 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
- 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
- QJATYMSFGSZXPG-UHFFFAOYSA-N 3-[ethoxy(dimethoxy)silyl]propyl prop-2-enoate Chemical compound CCO[Si](OC)(OC)CCCOC(=O)C=C QJATYMSFGSZXPG-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 240000008564 Boehmeria nivea Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 244000043261 Hevea brasiliensis Species 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- JPYHHZQJCSQRJY-UHFFFAOYSA-N Phloroglucinol Natural products CCC=CCC=CCC=CCC=CCCCCC(=O)C1=C(O)C=C(O)C=C1O JPYHHZQJCSQRJY-UHFFFAOYSA-N 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- 241000220010 Rhode Species 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229920005549 butyl rubber Polymers 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- 230000002844 continuous effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 1
- 239000004312 hexamethylene tetramine Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- HTUMBQDCCIXGCV-UHFFFAOYSA-N lead oxide Chemical compound [O-2].[Pb+2] HTUMBQDCCIXGCV-UHFFFAOYSA-N 0.000 description 1
- YEXPOXQUZXUXJW-UHFFFAOYSA-N lead(II) oxide Inorganic materials [Pb]=O YEXPOXQUZXUXJW-UHFFFAOYSA-N 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 229960004011 methenamine Drugs 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 229920006173 natural rubber latex Polymers 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000010979 pH adjustment Methods 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 1
- 229960001553 phloroglucinol Drugs 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 230000036647 reaction Effects 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000003340 retarding agent Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000002256 xylenyl group Chemical class C1(C(C=CC=C1)C)(C)* 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/04—Reinforcing macromolecular compounds with loose or coherent fibrous material
- C08J5/06—Reinforcing macromolecular compounds with loose or coherent fibrous material using pretreated fibrous materials
- C08J5/08—Reinforcing macromolecular compounds with loose or coherent fibrous material using pretreated fibrous materials glass fibres
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29D—PRODUCING PARTICULAR ARTICLES FROM PLASTICS OR FROM SUBSTANCES IN A PLASTIC STATE
- B29D30/00—Producing pneumatic or solid tyres or parts thereof
- B29D30/06—Pneumatic tyres or parts thereof (e.g. produced by casting, moulding, compression moulding, injection moulding, centrifugal casting)
- B29D30/38—Textile inserts, e.g. cord or canvas layers, for tyres; Treatment of inserts prior to building the tyre
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B60—VEHICLES IN GENERAL
- B60C—VEHICLE TYRES; TYRE INFLATION; TYRE CHANGING; CONNECTING VALVES TO INFLATABLE ELASTIC BODIES IN GENERAL; DEVICES OR ARRANGEMENTS RELATED TO TYRES
- B60C1/00—Tyres characterised by the chemical composition or the physical arrangement or mixture of the composition
-
- 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
- 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
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J121/00—Adhesives based on unspecified rubbers
- C09J121/02—Latex
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J161/00—Adhesives based on condensation polymers of aldehydes or ketones; Adhesives based on derivatives of such polymers
- C09J161/04—Condensation polymers of aldehydes or ketones with phenols only
- C09J161/06—Condensation polymers of aldehydes or ketones with phenols only of aldehydes with phenols
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29D—PRODUCING PARTICULAR ARTICLES FROM PLASTICS OR FROM SUBSTANCES IN A PLASTIC STATE
- B29D30/00—Producing pneumatic or solid tyres or parts thereof
- B29D30/06—Pneumatic tyres or parts thereof (e.g. produced by casting, moulding, compression moulding, injection moulding, centrifugal casting)
- B29D30/38—Textile inserts, e.g. cord or canvas layers, for tyres; Treatment of inserts prior to building the tyre
- B29D2030/383—Chemical treatment of the reinforcing elements, e.g. cords, wires and filamentary materials, to increase the adhesion to the rubber
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29L—INDEXING SCHEME ASSOCIATED WITH SUBCLASS B29C, RELATING TO PARTICULAR ARTICLES
- B29L2030/00—Pneumatic or solid tyres or parts thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2321/00—Characterised by the use of unspecified rubbers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
- C08L2666/02—Organic macromolecular compounds, natural resins, waxes or and bituminous materials
- C08L2666/14—Macromolecular compounds according to C08L59/00 - C08L87/00; Derivatives thereof
- C08L2666/16—Addition or condensation polymers of aldehydes or ketones according to C08L59/00 - C08L61/00; Derivatives thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Mechanical Engineering (AREA)
- Materials Engineering (AREA)
- Textile Engineering (AREA)
- Manufacturing & Machinery (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Reinforced Plastic Materials (AREA)
- Laminated Bodies (AREA)
- Lining Or Joining Of Plastics Or The Like (AREA)
- Phenolic Resins Or Amino Resins (AREA)
- Moulding By Coating Moulds (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US16335580A | 1980-06-26 | 1980-06-26 | |
| US163,355 | 1980-06-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1173580A true CA1173580A (fr) | 1984-08-28 |
Family
ID=22589667
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000368266A Expired CA1173580A (fr) | 1980-06-26 | 1981-01-12 | Methode pour preparer une resine d'aldehyde phenolique, et compositon de resine pour systeme adhesif applique sur des fibres de verre |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS5714614A (fr) |
| BE (1) | BE887384A (fr) |
| CA (1) | CA1173580A (fr) |
| DE (1) | DE3121382A1 (fr) |
| FR (1) | FR2485435A1 (fr) |
| GB (1) | GB2082607A (fr) |
| IT (1) | IT1146738B (fr) |
| NL (1) | NL8100369A (fr) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2125451B (en) * | 1982-08-13 | 1986-01-02 | Borg Warner | Extrusion coated continuous tape |
| JP4460581B2 (ja) * | 2004-06-28 | 2010-05-12 | 日本板硝子株式会社 | ゴム補強用コードおよびその製造方法ならびにそれを用いたゴム製品 |
| FR2978769B1 (fr) | 2011-08-04 | 2013-09-27 | Michelin Soc Tech | Composition adhesive aqueuse a base de polyaldehyde et de polyphenol |
| FR2978771B1 (fr) | 2011-08-04 | 2013-09-27 | Michelin Soc Tech | Composition adhesive aqueuse a base de polyaldehyde et 2,2', 4,4'-tetrahydroxydiphenyl sulfide |
| FR2978770B1 (fr) | 2011-08-04 | 2013-09-27 | Michelin Soc Tech | Composition adhesive aqueuse a base de polyaldehyde et phloroglucinol |
| FR3008707B1 (fr) * | 2013-07-16 | 2017-11-10 | Michelin & Cie | Composition adhesive aqueuse a base d'aldehyde biosource et de polyphenol |
| FR3017070B1 (fr) * | 2014-02-06 | 2017-08-25 | Michelin & Cie | Element de renfort en acier revetu par une composition adhesive a base d'aldehyde aromatique et de polyphenol |
| FR3031746A1 (fr) | 2015-01-21 | 2016-07-22 | Michelin & Cie | Composition de caoutchouc a haute rigidite |
| FR3031745A1 (fr) | 2015-01-21 | 2016-07-22 | Michelin & Cie | Composition de caoutchouc a haute rigidite |
| US10604613B2 (en) | 2015-01-21 | 2020-03-31 | Compagnie Generale Des Etablissements Michelin | High-rigidity rubber composition |
| CN109266283A (zh) * | 2018-08-06 | 2019-01-25 | 岳西县明杰电子有限公司 | 一种变压器用耐老化绝缘胶黏剂 |
| CN109456516B (zh) * | 2018-11-19 | 2021-03-05 | 北京彤程创展科技有限公司 | 一种双酚化合物改性间苯二酚树脂、橡胶组合物及其制备方法 |
| CN111088700A (zh) * | 2019-12-03 | 2020-05-01 | 浙江尤夫科技工业有限公司 | 橡胶帆布浸胶配方及其制备方法和橡胶帆布的制备方法 |
| CN115353710A (zh) * | 2022-08-19 | 2022-11-18 | 山东北方现代化学工业有限公司 | 一种尼龙增强高强度玻璃纤维酚醛复合材料及其制备方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE365286C (de) * | 1920-06-17 | 1922-12-14 | Hoechst Ag | Verfahren zur Herstellung von harzartigen Kondensationsprodukten aus Phenolen und Acetaldehyd |
| US2494537A (en) * | 1946-07-26 | 1950-01-17 | Glen E Babcock | Cold-setting resorcinol glue composition and process of preparation |
| GB1034950A (en) * | 1963-11-15 | 1966-07-06 | Pirelli | Improvements in or relating to the preparation of liquid adhesive compositions for the treatment of textile materials and to the treatment of textile materials with suchcompositions |
-
1981
- 1981-01-12 CA CA000368266A patent/CA1173580A/fr not_active Expired
- 1981-01-27 NL NL8100369A patent/NL8100369A/nl not_active Application Discontinuation
- 1981-02-03 IT IT67145/81A patent/IT1146738B/it active
- 1981-02-04 BE BE0/203697A patent/BE887384A/fr not_active IP Right Cessation
- 1981-02-17 FR FR8103100A patent/FR2485435A1/fr not_active Withdrawn
- 1981-03-24 JP JP4384881A patent/JPS5714614A/ja active Pending
- 1981-05-29 DE DE19813121382 patent/DE3121382A1/de not_active Withdrawn
- 1981-06-04 GB GB8117118A patent/GB2082607A/en not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| DE3121382A1 (de) | 1982-02-25 |
| FR2485435A1 (fr) | 1981-12-31 |
| NL8100369A (nl) | 1982-01-18 |
| JPS5714614A (en) | 1982-01-25 |
| GB2082607A (en) | 1982-03-10 |
| BE887384A (fr) | 1981-08-04 |
| IT1146738B (it) | 1986-11-19 |
| IT8167145A0 (it) | 1981-02-03 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4476191A (en) | Resorcinol-aldehyde resin composition for an adhesive system to be applied to glass fibers | |
| CA1173580A (fr) | Methode pour preparer une resine d'aldehyde phenolique, et compositon de resine pour systeme adhesif applique sur des fibres de verre | |
| US7589164B2 (en) | Flexibilized resorcinolic novolak resins and method of making same | |
| US4461859A (en) | Method of preparing a phenolic aldehyde resin and resin composition for an adhesive system to be applied to glass fibers | |
| US3991027A (en) | Method for bonding polyamides to rubber, adhesive for the same, and adhesive coated polyamide reinforcing elements | |
| US3226276A (en) | Method of bonding cord to rubber with a phenol-aldehyde blocked polyisocyanate | |
| CA1043025A (fr) | Adherence du caoutchouc a des materiaux d'armement | |
| US3437122A (en) | Cord dip of improved stability | |
| US4314050A (en) | Method of preparing a phenolic aldehyde resin and resin composition for an adhesive system to be applied to glass fibers | |
| US3663268A (en) | Process for adhering polyester tire cord to rubber | |
| US2691614A (en) | Adhesive composition and article containing said adhesive and methods for making thesame | |
| US3256137A (en) | Adhering textile materials to rubber | |
| US3325333A (en) | Adhesion of polyester materials to a rubber compound | |
| US4393189A (en) | Method of preparing a phenolic aldehyde resin and resin composition for an adhesive system to be applied to glass fibers | |
| KR960006406B1 (ko) | 아닐린-레조르신-포롬알데히드 공중축합 생성물 | |
| EP3957494A1 (fr) | Adhésif de renforcement de caoutchouc | |
| US3538972A (en) | Adhesive systems method of bonding reinforcement to rubber and resulting products | |
| US3698935A (en) | Reinforcing elements for rubber | |
| US4016119A (en) | Lignin sulfonate for glass cord adhesives | |
| US4049603A (en) | Adhesion of glass fibers to rubber | |
| US4246144A (en) | Modified phenolic aldehyde resin to produce an improved adhesive coating and method of making same | |
| US3638703A (en) | Heat stable polyester cord reinforced rubber structure | |
| US2211960A (en) | Artificial cellulosic material bonded to rubber and method of producing the bond | |
| JPS6310751B2 (fr) | ||
| US2643207A (en) | Bonding of textile yarns to rubber |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |