CA1100711A - Process for the production of a storable, scorch- resistant rubber-fabric bonding agent combination - Google Patents
Process for the production of a storable, scorch- resistant rubber-fabric bonding agent combinationInfo
- Publication number
- CA1100711A CA1100711A CA283,607A CA283607A CA1100711A CA 1100711 A CA1100711 A CA 1100711A CA 283607 A CA283607 A CA 283607A CA 1100711 A CA1100711 A CA 1100711A
- Authority
- CA
- Canada
- Prior art keywords
- resorcinol
- bis
- parts
- rubber
- composition
- 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
- 238000000034 method Methods 0.000 title claims description 11
- 239000007767 bonding agent Substances 0.000 title description 3
- 239000004744 fabric Substances 0.000 title description 2
- 238000004519 manufacturing process Methods 0.000 title description 2
- 239000000203 mixture Substances 0.000 claims abstract description 58
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 48
- 229920001971 elastomer Polymers 0.000 claims abstract description 37
- 239000005060 rubber Substances 0.000 claims abstract description 37
- 150000005207 1,3-dihydroxybenzenes Chemical class 0.000 claims abstract description 12
- 239000004753 textile Substances 0.000 claims abstract description 11
- 239000000378 calcium silicate Substances 0.000 claims abstract description 9
- 229910052918 calcium silicate Inorganic materials 0.000 claims abstract description 9
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229910052751 metal Inorganic materials 0.000 claims abstract description 9
- 239000002184 metal Substances 0.000 claims abstract description 9
- 230000000737 periodic effect Effects 0.000 claims abstract description 8
- 229910044991 metal oxide Inorganic materials 0.000 claims abstract description 6
- 150000004706 metal oxides Chemical class 0.000 claims abstract description 6
- -1 alkenyl radical Chemical class 0.000 claims description 152
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 73
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 229920000570 polyether Polymers 0.000 claims description 7
- 150000005840 aryl radicals Chemical class 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 239000000047 product Substances 0.000 claims description 4
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
- 238000002844 melting Methods 0.000 claims description 3
- 230000008018 melting Effects 0.000 claims description 3
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical class OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims description 3
- 125000005504 styryl group Chemical group 0.000 claims description 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- PELYILSDOPJJQD-UHFFFAOYSA-N benzene-1,3-diol ethyl carbamate Chemical class CCOC(N)=O.OC1=CC=CC(O)=C1 PELYILSDOPJJQD-UHFFFAOYSA-N 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 2
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- IPZJQDSFZGZEOY-UHFFFAOYSA-N dimethylmethylene Chemical group C[C]C IPZJQDSFZGZEOY-UHFFFAOYSA-N 0.000 claims description 2
- 230000032050 esterification Effects 0.000 claims description 2
- 238000005886 esterification reaction Methods 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 2
- 125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 claims 1
- ZZJVDYQPZOHNIK-UHFFFAOYSA-N 2,6-dihydroxybenzenesulfonic acid Chemical class OC1=CC=CC(O)=C1S(O)(=O)=O ZZJVDYQPZOHNIK-UHFFFAOYSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims 1
- 230000003014 reinforcing effect Effects 0.000 claims 1
- 125000003396 thiol group Chemical class [H]S* 0.000 claims 1
- 150000003579 thiophosphoric acid derivatives Chemical class 0.000 claims 1
- 150000002739 metals Chemical class 0.000 abstract description 5
- 239000011521 glass Substances 0.000 abstract description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 39
- 239000000395 magnesium oxide Substances 0.000 description 23
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
- 239000002253 acid Substances 0.000 description 18
- 229920000728 polyester Polymers 0.000 description 17
- 239000008117 stearic acid Substances 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 14
- 150000002148 esters Chemical class 0.000 description 14
- 235000021355 Stearic acid Nutrition 0.000 description 12
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 12
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 12
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 12
- 229920000297 Rayon Polymers 0.000 description 10
- JQALNNOQTGZTJZ-UHFFFAOYSA-N [[4,6-bis[bis(methoxymethyl)amino]-1,3,5-triazin-2-yl]-(methoxymethyl)amino]methanol Chemical compound COCN(CO)C1=NC(N(COC)COC)=NC(N(COC)COC)=N1 JQALNNOQTGZTJZ-UHFFFAOYSA-N 0.000 description 10
- 239000002964 rayon Substances 0.000 description 10
- 229920001084 poly(chloroprene) Polymers 0.000 description 9
- 239000000377 silicon dioxide Substances 0.000 description 9
- 229910000831 Steel Inorganic materials 0.000 description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 8
- 239000005864 Sulphur Substances 0.000 description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 8
- 229920002635 polyurethane Polymers 0.000 description 8
- 239000004814 polyurethane Substances 0.000 description 8
- 239000010959 steel Substances 0.000 description 8
- 239000004677 Nylon Substances 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 229920001778 nylon Polymers 0.000 description 7
- OPNUROKCUBTKLF-UHFFFAOYSA-N 1,2-bis(2-methylphenyl)guanidine Chemical compound CC1=CC=CC=C1N\C(N)=N\C1=CC=CC=C1C OPNUROKCUBTKLF-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 239000004721 Polyphenylene oxide Substances 0.000 description 6
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 6
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- 229920003052 natural elastomer Polymers 0.000 description 6
- 229920001194 natural rubber Polymers 0.000 description 6
- 239000011787 zinc oxide Substances 0.000 description 6
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 5
- 244000043261 Hevea brasiliensis Species 0.000 description 5
- 150000001733 carboxylic acid esters Chemical class 0.000 description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 5
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- DPZNOMCNRMUKPS-UHFFFAOYSA-N 1,3-Dimethoxybenzene Chemical compound COC1=CC=CC(OC)=C1 DPZNOMCNRMUKPS-UHFFFAOYSA-N 0.000 description 4
- VPDZKXNFJWXDGF-UHFFFAOYSA-N 5-butoxy-5-oxo-2,4-bis(sulfanyl)pentanoic acid Chemical compound CCCCOC(=O)C(S)CC(S)C(O)=O VPDZKXNFJWXDGF-UHFFFAOYSA-N 0.000 description 4
- 101100087530 Caenorhabditis elegans rom-1 gene Proteins 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 101100305983 Mus musculus Rom1 gene Proteins 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- REQPQFUJGGOFQL-UHFFFAOYSA-N dimethylcarbamothioyl n,n-dimethylcarbamodithioate Chemical compound CN(C)C(=S)SC(=S)N(C)C REQPQFUJGGOFQL-UHFFFAOYSA-N 0.000 description 3
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical compound [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- 235000010446 mineral oil Nutrition 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 125000003107 substituted aryl group Chemical group 0.000 description 3
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
- 125000003229 2-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 2
- BTXXTMOWISPQSJ-UHFFFAOYSA-N 4,4,4-trifluorobutan-2-one Chemical compound CC(=O)CC(F)(F)F BTXXTMOWISPQSJ-UHFFFAOYSA-N 0.000 description 2
- BQACOLQNOUYJCE-FYZZASKESA-N Abietic acid Natural products CC(C)C1=CC2=CC[C@]3(C)[C@](C)(CCC[C@@]3(C)C(=O)O)[C@H]2CC1 BQACOLQNOUYJCE-FYZZASKESA-N 0.000 description 2
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 2
- DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- 229920002943 EPDM rubber Polymers 0.000 description 2
- 229920000877 Melamine resin Polymers 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 239000005062 Polybutadiene Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
- YGCOKJWKWLYHTG-UHFFFAOYSA-N [[4,6-bis[bis(hydroxymethyl)amino]-1,3,5-triazin-2-yl]-(hydroxymethyl)amino]methanol Chemical compound OCN(CO)C1=NC(N(CO)CO)=NC(N(CO)CO)=N1 YGCOKJWKWLYHTG-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 229940105289 carbon black Drugs 0.000 description 2
- 235000019241 carbon black Nutrition 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- JKWMSGQKBLHBQQ-UHFFFAOYSA-N diboron trioxide Chemical compound O=BOB=O JKWMSGQKBLHBQQ-UHFFFAOYSA-N 0.000 description 2
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 2
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 2
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 229920003246 polypentenamer Polymers 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- IATRAKWUXMZMIY-UHFFFAOYSA-N strontium oxide Chemical compound [O-2].[Sr+2] IATRAKWUXMZMIY-UHFFFAOYSA-N 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 2
- 238000004073 vulcanization Methods 0.000 description 2
- KAORMOYKRFIJDJ-BUXJGYRWSA-N (2E,4E)-2-[3-[(1E,3E)-1,4-dicarboxybuta-1,3-dienyl]-2,4-dihydroxyphenyl]hexa-2,4-dienedioic acid Chemical compound C1=CC(=C(C(=C1/C(=C\C=C\C(=O)O)/C(=O)O)O)/C(=C\C=C\C(=O)O)/C(=O)O)O KAORMOYKRFIJDJ-BUXJGYRWSA-N 0.000 description 1
- STOUHHBZBQBYHH-UHFFFAOYSA-N (3-acetyloxyphenyl) acetate Chemical compound CC(=O)OC1=CC=CC(OC(C)=O)=C1 STOUHHBZBQBYHH-UHFFFAOYSA-N 0.000 description 1
- UKDWCDFYKUAITL-UHFFFAOYSA-N (3-propanoyloxyphenyl) propanoate Chemical compound CCC(=O)OC1=CC=CC(OC(=O)CC)=C1 UKDWCDFYKUAITL-UHFFFAOYSA-N 0.000 description 1
- PRBHEGAFLDMLAL-GQCTYLIASA-N (4e)-hexa-1,4-diene Chemical compound C\C=C\CC=C PRBHEGAFLDMLAL-GQCTYLIASA-N 0.000 description 1
- OJOWICOBYCXEKR-KRXBUXKQSA-N (5e)-5-ethylidenebicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(=C/C)/CC1C=C2 OJOWICOBYCXEKR-KRXBUXKQSA-N 0.000 description 1
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- AGLSFOYZWUIESQ-UHFFFAOYSA-N 1,3-bis(3-methylbutoxy)benzene Chemical compound CC(C)CCOC1=CC=CC(OCCC(C)C)=C1 AGLSFOYZWUIESQ-UHFFFAOYSA-N 0.000 description 1
- RESHZVQZWMQUMB-UHFFFAOYSA-N 1,3-bis(phenylmethoxy)benzene Chemical compound C=1C=CC=CC=1COC(C=1)=CC=CC=1OCC1=CC=CC=C1 RESHZVQZWMQUMB-UHFFFAOYSA-N 0.000 description 1
- OIPUSGXLZPNABH-UHFFFAOYSA-N 1,3-dibutoxybenzene Chemical compound CCCCOC1=CC=CC(OCCCC)=C1 OIPUSGXLZPNABH-UHFFFAOYSA-N 0.000 description 1
- MKGFYMKFBCWNCP-UHFFFAOYSA-N 1,3-diethoxybenzene Chemical compound CCOC1=CC=CC(OCC)=C1 MKGFYMKFBCWNCP-UHFFFAOYSA-N 0.000 description 1
- RAXJNVWFDRAINI-UHFFFAOYSA-N 1,3-dihexoxybenzene Chemical compound CCCCCCOC1=CC=CC(OCCCCCC)=C1 RAXJNVWFDRAINI-UHFFFAOYSA-N 0.000 description 1
- SCWFYCTYTFSJNZ-UHFFFAOYSA-N 1,3-dipentoxybenzene Chemical compound CCCCCOC1=CC=CC(OCCCCC)=C1 SCWFYCTYTFSJNZ-UHFFFAOYSA-N 0.000 description 1
- UTFRNSPYRPYKDV-UHFFFAOYSA-N 1,3-dipropoxybenzene Chemical compound CCCOC1=CC=CC(OCCC)=C1 UTFRNSPYRPYKDV-UHFFFAOYSA-N 0.000 description 1
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- ZSYKCEAWKWRSGX-UHFFFAOYSA-N 2-[3-(1,3-dicarboxypropyl)-2,4-dihydroxyphenyl]pentanedioic acid Chemical compound C=1(O)C(=C(O)C(=CC=1)C(CCC(=O)O)C(=O)O)C(CCC(=O)O)C(=O)O ZSYKCEAWKWRSGX-UHFFFAOYSA-N 0.000 description 1
- YHNXRUUVFJCVKY-UHFFFAOYSA-N 2-[3-(2-carboxyphenyl)-2,4-dihydroxyphenyl]benzoic acid Chemical compound C1=CC=C(C(=C1)C2=C(C(=C(C=C2)O)C3=CC=CC=C3C(=O)O)O)C(=O)O YHNXRUUVFJCVKY-UHFFFAOYSA-N 0.000 description 1
- DLGDCSLVUIRTGW-UHFFFAOYSA-N 2-[[3-(2-carboxyprop-2-enyl)-2,4-dihydroxyphenyl]methyl]prop-2-enoic acid Chemical compound C=C(CC1=C(C(=C(C=C1)O)CC(=C)C(=O)O)O)C(=O)O DLGDCSLVUIRTGW-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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
- C08J5/10—Reinforcing macromolecular compounds with loose or coherent fibrous material characterised by the additives used in the polymer mixture
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/20—Oxides; Hydroxides
- C08K3/22—Oxides; Hydroxides of metals
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/34—Silicon-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L21/00—Compositions of unspecified rubbers
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- 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
- C08L61/12—Condensation polymers of aldehydes or ketones with phenols only of aldehydes with phenols with polyhydric phenols
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2913—Rod, strand, filament or fiber
- Y10T428/2933—Coated or with bond, impregnation or core
- Y10T428/294—Coated or with bond, impregnation or core including metal or compound thereof [excluding glass, ceramic and asbestos]
- Y10T428/296—Rubber, cellulosic or silicic material in coating
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2913—Rod, strand, filament or fiber
- Y10T428/2933—Coated or with bond, impregnation or core
- Y10T428/2964—Artificial fiber or filament
- Y10T428/2967—Synthetic resin or polymer
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2913—Rod, strand, filament or fiber
- Y10T428/2933—Coated or with bond, impregnation or core
- Y10T428/2964—Artificial fiber or filament
- Y10T428/2967—Synthetic resin or polymer
- Y10T428/2969—Polyamide, polyimide or polyester
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Materials Engineering (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Lining Or Joining Of Plastics Or The Like (AREA)
- Reinforced Plastic Materials (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP2634034.1 | 1976-07-29 | ||
| DE2634034A DE2634034C3 (de) | 1976-07-29 | 1976-07-29 | Verwendung einer Mischung aus Resorcinester, Hexamethylolmelamin, Calciumsilicat und einem Metalloxid zur Haftverbesserung von Polychloroprenkautschuk und Textilien oder Metallen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1100711A true CA1100711A (en) | 1981-05-12 |
Family
ID=5984181
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA283,607A Expired CA1100711A (en) | 1976-07-29 | 1977-07-27 | Process for the production of a storable, scorch- resistant rubber-fabric bonding agent combination |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4125512A (show.php) |
| JP (1) | JPS587663B2 (show.php) |
| BE (1) | BE857253A (show.php) |
| BR (1) | BR7704974A (show.php) |
| CA (1) | CA1100711A (show.php) |
| DE (1) | DE2634034C3 (show.php) |
| ES (1) | ES461111A1 (show.php) |
| FR (1) | FR2359877A1 (show.php) |
| GB (1) | GB1552097A (show.php) |
| IN (1) | IN146787B (show.php) |
| IT (1) | IT1079389B (show.php) |
| NL (1) | NL7708395A (show.php) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3033711A1 (de) * | 1980-09-08 | 1982-04-22 | Continental Gummi-Werke Ag, 3000 Hannover | Kautschukmischung zur direktbindung an metallflaechen |
| JPS61272170A (ja) * | 1985-05-28 | 1986-12-02 | Tokyo Electric Co Ltd | サ−マルヘツド駆動装置 |
| DE3538975C1 (de) * | 1985-11-02 | 1986-08-14 | Continental Gummi-Werke Ag, 3000 Hannover | Kautschukhaftmischung zur Direktbindung an metallischen Koerpern oder Glas |
| JP5471826B2 (ja) * | 2010-05-21 | 2014-04-16 | 横浜ゴム株式会社 | タイヤトレッド用ゴム組成物およびそれを用いた空気入りタイヤ |
| EP3599263A1 (de) * | 2018-07-26 | 2020-01-29 | LANXESS Deutschland GmbH | Haftmischungen für kautschuke |
| CN111172762B (zh) * | 2018-11-13 | 2021-12-21 | 北京化工大学 | 一种纤维表面处理的纳米强化环保浸渍体系及其制备方法 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1298703U (show.php) * | ||||
| DE1301475U (show.php) * | ||||
| CH433713A (de) * | 1961-12-18 | 1967-04-15 | Du Pont | Mit synthetischem Cordgarn aus Polyester oder Polyamid verstärkte elastomere Artikel |
| CH466558A (de) * | 1962-11-14 | 1968-12-15 | Du Pont | Mittels Cordgarn armierte Elastomerprodukte und Verfahren zu ihrer Herstellung |
| GB1062527A (en) * | 1962-11-30 | 1967-03-22 | Dunlop Rubber Co | Bonding textile materials to rubber |
| DE1298703B (de) * | 1964-08-14 | 1969-07-03 | Bayer Ag | Verfahren zum haftfesten Verbinden von Kautschuk mit Textilien |
| DE1301475C2 (de) * | 1965-10-02 | 1973-07-12 | Bayer Ag | Verfahren zur Erhoehung der Haftfestigkeit zwischen Gummi und Textilien |
| LU53123A1 (show.php) * | 1966-03-08 | 1967-05-03 | ||
| NL137702C (show.php) * | 1966-07-06 | |||
| GB1278940A (en) * | 1968-09-19 | 1972-06-21 | Dunlop Holdings Ltd | Polyester reinforced rubber articles |
| US3821133A (en) * | 1971-12-06 | 1974-06-28 | Ppg Industries Inc | Abrasion-resistant vulcanizates |
| JPS5143515B2 (show.php) * | 1973-02-16 | 1976-11-22 | ||
| US3969568A (en) * | 1974-12-04 | 1976-07-13 | Uniroyal Inc. | Aramid floc reinforcement of rubber using particular adhesive |
| FR2399456A1 (fr) * | 1977-08-03 | 1979-03-02 | Kleber Colombes | Articles en caoutchouc comportant une armature en polyester |
-
1976
- 1976-07-29 DE DE2634034A patent/DE2634034C3/de not_active Expired
-
1977
- 1977-07-05 IN IN1016/CAL/77A patent/IN146787B/en unknown
- 1977-07-26 US US05/819,007 patent/US4125512A/en not_active Expired - Lifetime
- 1977-07-26 GB GB31281/77A patent/GB1552097A/en not_active Expired
- 1977-07-27 CA CA283,607A patent/CA1100711A/en not_active Expired
- 1977-07-27 JP JP52089387A patent/JPS587663B2/ja not_active Expired
- 1977-07-27 IT IT50462/77A patent/IT1079389B/it active
- 1977-07-28 NL NL7708395A patent/NL7708395A/xx not_active Application Discontinuation
- 1977-07-28 BE BE179721A patent/BE857253A/xx not_active IP Right Cessation
- 1977-07-28 ES ES461111A patent/ES461111A1/es not_active Expired
- 1977-07-28 BR BR7704974A patent/BR7704974A/pt unknown
- 1977-07-29 FR FR7723494A patent/FR2359877A1/fr not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| DE2634034B2 (de) | 1978-12-21 |
| JPS587663B2 (ja) | 1983-02-10 |
| GB1552097A (en) | 1979-09-05 |
| BR7704974A (pt) | 1978-04-25 |
| BE857253A (fr) | 1978-01-30 |
| FR2359877A1 (fr) | 1978-02-24 |
| ES461111A1 (es) | 1978-06-01 |
| IN146787B (show.php) | 1979-09-08 |
| NL7708395A (nl) | 1978-01-31 |
| JPS5316095A (en) | 1978-02-14 |
| IT1079389B (it) | 1985-05-08 |
| DE2634034C3 (de) | 1985-04-04 |
| US4125512A (en) | 1978-11-14 |
| DE2634034A1 (de) | 1978-02-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |