DE2636187A1 - Petrolharze - Google Patents
PetrolharzeInfo
- Publication number
- DE2636187A1 DE2636187A1 DE19762636187 DE2636187A DE2636187A1 DE 2636187 A1 DE2636187 A1 DE 2636187A1 DE 19762636187 DE19762636187 DE 19762636187 DE 2636187 A DE2636187 A DE 2636187A DE 2636187 A1 DE2636187 A1 DE 2636187A1
- Authority
- DE
- Germany
- Prior art keywords
- resin
- olefins
- resins
- weight
- rubber
- 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.)
- Withdrawn
Links
- 229920005989 resin Polymers 0.000 title claims description 148
- 239000011347 resin Substances 0.000 title claims description 148
- 150000001336 alkenes Chemical class 0.000 claims description 47
- 238000000034 method Methods 0.000 claims description 34
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 26
- 239000003208 petroleum Substances 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 24
- 238000006116 polymerization reaction Methods 0.000 claims description 18
- -1 aliphatic Olefin Chemical class 0.000 claims description 16
- 150000001993 dienes Chemical class 0.000 claims description 12
- 238000012546 transfer Methods 0.000 claims description 12
- 239000003674 animal food additive Substances 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 10
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 8
- FXNDIJDIPNCZQJ-UHFFFAOYSA-N 2,4,4-trimethylpent-1-ene Chemical compound CC(=C)CC(C)(C)C FXNDIJDIPNCZQJ-UHFFFAOYSA-N 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 238000005336 cracking Methods 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 150000001491 aromatic compounds Chemical class 0.000 claims description 4
- 150000002989 phenols Chemical class 0.000 claims description 4
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 claims description 4
- 150000008064 anhydrides Chemical class 0.000 claims description 3
- 150000001983 dialkylethers Chemical class 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- LRTOHSLOFCWHRF-UHFFFAOYSA-N 1-methyl-1h-indene Chemical compound C1=CC=C2C(C)C=CC2=C1 LRTOHSLOFCWHRF-UHFFFAOYSA-N 0.000 claims description 2
- SBYMUDUGTIKLCR-UHFFFAOYSA-N 2-chloroethenylbenzene Chemical compound ClC=CC1=CC=CC=C1 SBYMUDUGTIKLCR-UHFFFAOYSA-N 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 238000000576 coating method Methods 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 238000011068 loading method Methods 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 239000011248 coating agent Substances 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 48
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 38
- 229920001971 elastomer Polymers 0.000 description 35
- 239000000853 adhesive Substances 0.000 description 31
- 239000005060 rubber Substances 0.000 description 30
- 239000003054 catalyst Substances 0.000 description 24
- 239000000654 additive Substances 0.000 description 22
- 230000001070 adhesive effect Effects 0.000 description 18
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 16
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 15
- 238000005096 rolling process Methods 0.000 description 15
- 230000000996 additive effect Effects 0.000 description 13
- 238000009835 boiling Methods 0.000 description 12
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 12
- 239000003921 oil Substances 0.000 description 12
- 125000003118 aryl group Chemical group 0.000 description 11
- 239000003973 paint Substances 0.000 description 10
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 9
- 238000009472 formulation Methods 0.000 description 9
- 229920003052 natural elastomer Polymers 0.000 description 9
- 229920001194 natural rubber Polymers 0.000 description 9
- 239000000123 paper Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 229920003048 styrene butadiene rubber Polymers 0.000 description 9
- 239000001993 wax Substances 0.000 description 9
- 125000001931 aliphatic group Chemical group 0.000 description 8
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 229940078552 o-xylene Drugs 0.000 description 8
- 244000043261 Hevea brasiliensis Species 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical class C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 6
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 229920004939 Cariflex™ Polymers 0.000 description 5
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 5
- 239000002174 Styrene-butadiene Substances 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 5
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 238000009826 distribution Methods 0.000 description 5
- 239000000806 elastomer Substances 0.000 description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- WGECXQBGLLYSFP-UHFFFAOYSA-N (+-)-2,3-dimethyl-pentane Natural products CCC(C)C(C)C WGECXQBGLLYSFP-UHFFFAOYSA-N 0.000 description 4
- 239000004606 Fillers/Extenders Substances 0.000 description 4
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 4
- 229920002633 Kraton (polymer) Polymers 0.000 description 4
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000005038 ethylene vinyl acetate Substances 0.000 description 4
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 4
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 4
- 239000010802 sludge Substances 0.000 description 4
- 229920001169 thermoplastic Polymers 0.000 description 4
- 239000004416 thermosoftening plastic Substances 0.000 description 4
- PMJHHCWVYXUKFD-PLNGDYQASA-N (3z)-penta-1,3-diene Chemical compound C\C=C/C=C PMJHHCWVYXUKFD-PLNGDYQASA-N 0.000 description 3
- BZHMBWZPUJHVEE-UHFFFAOYSA-N 2,4-dimethylpentane Chemical compound CC(C)CC(C)C BZHMBWZPUJHVEE-UHFFFAOYSA-N 0.000 description 3
- ROGIWVXWXZRRMZ-UHFFFAOYSA-N 2-methylbuta-1,3-diene;styrene Chemical compound CC(=C)C=C.C=CC1=CC=CC=C1 ROGIWVXWXZRRMZ-UHFFFAOYSA-N 0.000 description 3
- 239000004831 Hot glue Substances 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 229920001400 block copolymer Polymers 0.000 description 3
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000005194 fractionation Methods 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 229920003049 isoprene rubber Polymers 0.000 description 3
- 239000004816 latex Substances 0.000 description 3
- 229920000126 latex Polymers 0.000 description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 239000000025 natural resin Substances 0.000 description 3
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 229920002725 thermoplastic elastomer Polymers 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- 150000003738 xylenes Chemical class 0.000 description 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- FLTJDUOFAQWHDF-UHFFFAOYSA-N 2,2-dimethylhexane Chemical compound CCCCC(C)(C)C FLTJDUOFAQWHDF-UHFFFAOYSA-N 0.000 description 2
- CXOWYJMDMMMMJO-UHFFFAOYSA-N 2,2-dimethylpentane Chemical compound CCCC(C)(C)C CXOWYJMDMMMMJO-UHFFFAOYSA-N 0.000 description 2
- HDGQICNBXPAKLR-UHFFFAOYSA-N 2,4-dimethylhexane Chemical compound CCC(C)CC(C)C HDGQICNBXPAKLR-UHFFFAOYSA-N 0.000 description 2
- UWNADWZGEHDQAB-UHFFFAOYSA-N 2,5-dimethylhexane Chemical compound CC(C)CCC(C)C UWNADWZGEHDQAB-UHFFFAOYSA-N 0.000 description 2
- MHNNAWXXUZQSNM-UHFFFAOYSA-N 2-methylbut-1-ene Chemical compound CCC(C)=C MHNNAWXXUZQSNM-UHFFFAOYSA-N 0.000 description 2
- GXDHCNNESPLIKD-UHFFFAOYSA-N 2-methylhexane Chemical compound CCCCC(C)C GXDHCNNESPLIKD-UHFFFAOYSA-N 0.000 description 2
- KUMXLFIBWFCMOJ-UHFFFAOYSA-N 3,3-dimethylhexane Chemical compound CCCC(C)(C)CC KUMXLFIBWFCMOJ-UHFFFAOYSA-N 0.000 description 2
- RNTWWGNZUXGTAX-UHFFFAOYSA-N 3,4-dimethylhexane Chemical compound CCC(C)C(C)CC RNTWWGNZUXGTAX-UHFFFAOYSA-N 0.000 description 2
- LAIUFBWHERIJIH-UHFFFAOYSA-N 3-Methylheptane Chemical compound CCCCC(C)CC LAIUFBWHERIJIH-UHFFFAOYSA-N 0.000 description 2
- AORMDLNPRGXHHL-UHFFFAOYSA-N 3-ethylpentane Chemical compound CCC(CC)CC AORMDLNPRGXHHL-UHFFFAOYSA-N 0.000 description 2
- VLJXXKKOSFGPHI-UHFFFAOYSA-N 3-methylhexane Chemical compound CCCC(C)CC VLJXXKKOSFGPHI-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 229910015900 BF3 Inorganic materials 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 239000013032 Hydrocarbon resin Substances 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000004820 Pressure-sensitive adhesive Substances 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 238000004026 adhesive bonding Methods 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- DQXBYHZEEUGOBF-UHFFFAOYSA-N but-3-enoic acid;ethene Chemical group C=C.OC(=O)CC=C DQXBYHZEEUGOBF-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- 239000000539 dimer Substances 0.000 description 2
- KWKXNDCHNDYVRT-UHFFFAOYSA-N dodecylbenzene Chemical compound CCCCCCCCCCCCC1=CC=CC=C1 KWKXNDCHNDYVRT-UHFFFAOYSA-N 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229920006270 hydrocarbon resin Polymers 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 2
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- NFWSQSCIDYBUOU-UHFFFAOYSA-N methylcyclopentadiene Chemical compound CC1=CC=CC1 NFWSQSCIDYBUOU-UHFFFAOYSA-N 0.000 description 2
- 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 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229920003051 synthetic elastomer Polymers 0.000 description 2
- 239000005061 synthetic rubber Substances 0.000 description 2
- ZISSAWUMDACLOM-UHFFFAOYSA-N triptane Chemical compound CC(C)C(C)(C)C ZISSAWUMDACLOM-UHFFFAOYSA-N 0.000 description 2
- JXPOLSKBTUYKJB-UHFFFAOYSA-N xi-2,3-Dimethylhexane Chemical compound CCCC(C)C(C)C JXPOLSKBTUYKJB-UHFFFAOYSA-N 0.000 description 2
- KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 description 1
- SZFRZEBLZFTODC-UHFFFAOYSA-N 2,3,4-trimethylpent-2-ene Chemical compound CC(C)C(C)=C(C)C SZFRZEBLZFTODC-UHFFFAOYSA-N 0.000 description 1
- RLPGDEORIPLBNF-UHFFFAOYSA-N 2,3,4-trimethylpentane Chemical compound CC(C)C(C)C(C)C RLPGDEORIPLBNF-UHFFFAOYSA-N 0.000 description 1
- LAAVYEUJEMRIGF-UHFFFAOYSA-N 2,4,4-trimethylpent-2-ene Chemical compound CC(C)=CC(C)(C)C LAAVYEUJEMRIGF-UHFFFAOYSA-N 0.000 description 1
- FEXBEKLLSUWSIM-UHFFFAOYSA-N 2-Butyl-4-methylphenol Chemical compound CCCCC1=CC(C)=CC=C1O FEXBEKLLSUWSIM-UHFFFAOYSA-N 0.000 description 1
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
- 101100153168 Arabidopsis thaliana TIC21 gene Proteins 0.000 description 1
- HIBWGGKDGCBPTA-UHFFFAOYSA-N C=CC1=CC=CC=C1.C=CC1=CC=CC=C1 Chemical compound C=CC1=CC=CC=C1.C=CC1=CC=CC=C1 HIBWGGKDGCBPTA-UHFFFAOYSA-N 0.000 description 1
- 101150110330 CRAT gene Proteins 0.000 description 1
- 229920000298 Cellophane Polymers 0.000 description 1
- AEXMKKGTQYQZCS-UHFFFAOYSA-N Dimethyl-diaethyl-methan Natural products CCC(C)(C)CC AEXMKKGTQYQZCS-UHFFFAOYSA-N 0.000 description 1
- 229920002943 EPDM rubber Polymers 0.000 description 1
- 229920003345 Elvax® Polymers 0.000 description 1
- 101100273813 Homo sapiens CDKN1A gene Proteins 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- 108700038981 SUMO-1 Proteins 0.000 description 1
- 101100083337 Schizosaccharomyces pombe (strain 972 / ATCC 24843) pic1 gene Proteins 0.000 description 1
- 102100026940 Small ubiquitin-related modifier 1 Human genes 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 241000746181 Therates Species 0.000 description 1
- 240000007591 Tilia tomentosa Species 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- ILXDAXZQNSOSAE-UHFFFAOYSA-N [AlH3].[Cl] Chemical compound [AlH3].[Cl] ILXDAXZQNSOSAE-UHFFFAOYSA-N 0.000 description 1
- 239000002313 adhesive film Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 229920005557 bromobutyl Polymers 0.000 description 1
- 150000001721 carbon Chemical class 0.000 description 1
- 238000010538 cationic polymerization reaction Methods 0.000 description 1
- 238000007385 chemical modification Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229920005556 chlorobutyl Polymers 0.000 description 1
- 101150116749 chuk gene Proteins 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000000895 extractive distillation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000003502 gasoline Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 239000012943 hotmelt Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 239000002655 kraft paper Substances 0.000 description 1
- 230000000873 masking effect Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- 230000003606 oligomerizing effect Effects 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- QRMPKOFEUHIBNM-UHFFFAOYSA-N p-dimethylcyclohexane Natural products CC1CCC(C)CC1 QRMPKOFEUHIBNM-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- QMMOXUPEWRXHJS-UHFFFAOYSA-N pent-2-ene Chemical compound CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
- 229920001084 poly(chloroprene) Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920006267 polyester film Polymers 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 150000003097 polyterpenes Chemical class 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical group CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 238000010058 rubber compounding Methods 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000004230 steam cracking Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- PUGUQINMNYINPK-UHFFFAOYSA-N tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(C(=O)CCl)CC1 PUGUQINMNYINPK-UHFFFAOYSA-N 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 description 1
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F240/00—Copolymers of hydrocarbons and mineral oils, e.g. petroleum resins
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Adhesives Or Adhesive Processes (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB33705/75A GB1538057A (en) | 1975-08-13 | 1975-08-13 | Petroleum resins |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2636187A1 true DE2636187A1 (de) | 1977-02-24 |
Family
ID=10356395
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762636187 Withdrawn DE2636187A1 (de) | 1975-08-13 | 1976-08-11 | Petrolharze |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4078132A (en, 2012) |
| JP (2) | JPS5916565B2 (en, 2012) |
| DE (1) | DE2636187A1 (en, 2012) |
| FR (1) | FR2320959A1 (en, 2012) |
| GB (1) | GB1538057A (en, 2012) |
| IT (1) | IT1062667B (en, 2012) |
| NL (1) | NL188907C (en, 2012) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4100598A1 (de) * | 1991-01-11 | 1992-07-16 | Ruetgerswerke Ag | Verfahren zur herstellung aromatischer kohlenwasserstoff-harze |
| EP3904410A1 (de) * | 2020-04-30 | 2021-11-03 | Rain Carbon Germany GmbH | Kohlenwasserstoffharz und verfahren zu seiner herstellung |
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1588299A (en) * | 1977-04-26 | 1981-04-23 | Mitsui Petrochemical Ind | Polymers of dicyclopentadienes unsaturated hydrocarbon fractions or vinyl aromatic hydrocarbons |
| GB2027721A (en) | 1978-06-27 | 1980-02-27 | Exxon Research Engineering Co | Petroleum resins |
| GB2032442A (en) * | 1978-10-20 | 1980-05-08 | Exxon Research Engineering Co | Petroleum resins |
| JPS5718712A (en) * | 1980-07-07 | 1982-01-30 | Nippon Oil Co Ltd | Improved preparation of hydrocarbon resin |
| GB8317510D0 (en) * | 1983-06-28 | 1983-08-03 | Exxon Research Engineering Co | Petroleum resins |
| US5284891A (en) * | 1985-03-25 | 1994-02-08 | Exxon Research & Engg. | Tackifiers and their use in pressure sensitive adhesives |
| US4677176A (en) * | 1986-02-18 | 1987-06-30 | Exxon Chemical Patents Inc. | Light color, low softening point petroleum hydrocarbon resins |
| CA1298026C (en) * | 1986-02-18 | 1992-03-24 | Mary E. Ahner | Light color, low softening point petroleum hydrocarbon resins and the pressure sensitive adhesives containing such resins |
| US4902766A (en) * | 1986-12-01 | 1990-02-20 | Exxon Chemical Patents Inc. | Liquid aliphatic resins |
| JPS63287882A (ja) * | 1987-05-20 | 1988-11-24 | 株式会社日立製作所 | 暗号装置 |
| EP0308137B1 (en) * | 1987-09-14 | 1992-01-08 | Exxon Chemical Patents Inc. | Hydrogenated liquid aliphatic hydrocarbon resins |
| GB9205841D0 (en) * | 1992-03-18 | 1992-04-29 | Exxon Chemical Patents Inc | Hydrocarbon resins,processes for their manufacture and adhesive compositions containing such resins |
| US5656698A (en) * | 1993-11-03 | 1997-08-12 | Exxon Chemical Patents Inc. | Aromatic tackifier resin |
| US5853874A (en) * | 1994-11-28 | 1998-12-29 | Exxon Chemical Patents, Inc. | Low viscosity hot melt pressure sensitive ashesive compositions |
| US5695837A (en) * | 1995-04-20 | 1997-12-09 | Minnesota Mining And Manufacturing Company | Tackified acrylic adhesives |
| ES2132913T3 (es) * | 1995-04-24 | 1999-08-16 | Minnesota Mining & Mfg | Adhesivos sensibles a la presion para superficies de poliolefina. |
| US6100224A (en) * | 1997-10-01 | 2000-08-08 | Exxon Chemical Patents Inc | Copolymers of ethylene α-olefin macromers and dicarboxylic monomers and derivatives thereof, useful as additives in lubricating oils and in fuels |
| CA2292925A1 (en) * | 1999-02-16 | 2000-08-16 | The Goodyear Tire & Rubber Company | Polymeric resinous material derived from limonene, dicyclopentadiene, indene and vinyl toluene |
| US6605680B1 (en) | 2000-04-07 | 2003-08-12 | Eastman Chemical Resins, Inc. | Low color, aromatic modified C5 hydrocarbon resins |
| CN101838362B (zh) | 2002-10-15 | 2012-11-28 | 埃克森美孚化学专利公司 | 聚烯烃粘合剂组合物和由其制成的制品 |
| US7700707B2 (en) | 2002-10-15 | 2010-04-20 | Exxonmobil Chemical Patents Inc. | Polyolefin adhesive compositions and articles made therefrom |
| US7223822B2 (en) | 2002-10-15 | 2007-05-29 | Exxonmobil Chemical Patents Inc. | Multiple catalyst and reactor system for olefin polymerization and polymers produced therefrom |
| US8242198B2 (en) | 2008-06-09 | 2012-08-14 | Exxonmobil Chemical Patents Inc. | Polyolefin adhesive compositions |
| US20110059277A1 (en) * | 2009-09-04 | 2011-03-10 | Rainer Kolb | Elastomeric Surface Coatings for Plastic Articles |
| WO2010147706A2 (en) * | 2009-06-16 | 2010-12-23 | Exxonmobil Chemical Patents Inc. | Polyolefin compositions for coating applications |
| US20100316820A1 (en) * | 2009-06-16 | 2010-12-16 | Rainer Kolb | Composite Materials Comprising Propylene-Based Polymer Blend Coatings |
| CN102834450B (zh) | 2010-04-13 | 2015-04-08 | 埃克森美孚化学专利公司 | 粘合剂组合物和方法 |
| JP5685317B2 (ja) | 2010-10-15 | 2015-03-18 | エクソンモービル ケミカル パテンツ インコーポレイテッド | ポリプロピレンベース接着剤組成物 |
| US8946365B2 (en) | 2012-01-18 | 2015-02-03 | Eastman Chemical Company | Low molecular weight polystyrene resin and methods of making and using the same |
| CN102816280A (zh) * | 2012-08-29 | 2012-12-12 | 宁波甬华树脂有限公司 | 一种二异丁烯改性碳五石油树脂的制备方法 |
| US9605186B2 (en) | 2012-09-19 | 2017-03-28 | Exxonmobil Chemical Patents Inc. | Adhesive compositions of ethylene-based and propylene-based polymers |
| CN104411794B (zh) | 2012-09-19 | 2016-04-06 | 埃克森美孚化学专利公司 | 丙烯-基以及乙烯-基聚合物的粘合剂组合物 |
| US20200248046A1 (en) | 2019-02-04 | 2020-08-06 | Exxonmobil Chemical Patents Inc. | Hot Melt Adhesive Compositions |
| US20230046550A1 (en) | 2019-12-04 | 2023-02-16 | Exxonmobil Research And Engineering Company | Adhesive compositions |
| US20250002764A1 (en) | 2021-12-17 | 2025-01-02 | ExxonMobil Technology and Engineering Company | Hot Melt Adhesives Comprising Lao-Derived Diluents |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2835650A (en) * | 1954-07-29 | 1958-05-20 | Exxon Research Engineering Co | Hydrocarbon resins odor stabilized with an alkyl-alkoxy monophenol |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2734046A (en) * | 1956-02-07 | Steam or | ||
| US2521432A (en) * | 1948-07-14 | 1950-09-05 | Standard Oil Dev Co | Activation of friedel-crafts catalysts for polymerization of olefins |
| US2856389A (en) * | 1953-07-22 | 1958-10-14 | Exxon Research Engineering Co | Petroleum resins containing indene |
| US2849512A (en) * | 1953-10-14 | 1958-08-26 | Exxon Research Engineering Co | Preparation of olefinc-aromatic feeds for solvent extraction |
| US2994689A (en) * | 1956-04-30 | 1961-08-01 | Exxon Research Engineering Co | Utilization of high boiling fractions in preparing petroleum resins |
| US2894937A (en) * | 1956-05-01 | 1959-07-14 | Exxon Research Engineering Co | Process for preparing petroleum resins ii |
| US2964504A (en) * | 1956-12-10 | 1960-12-13 | Exxon Research Engineering Co | Steam cracking of light naphtha and preparation of resins |
| US3014012A (en) * | 1958-05-08 | 1961-12-19 | Exxon Research Engineering Co | Removal of 2-methyl butene-1 from petroleum resin feeds |
| GB1043406A (en) * | 1962-05-23 | 1966-09-21 | Nippon Oil Co Ltd | The preparation of petroleum resins |
| US3577398A (en) * | 1966-06-09 | 1971-05-04 | Goodyear Tire & Rubber | Synthetic resin |
| FR1489884A (fr) * | 1966-06-17 | 1967-07-28 | Exxon Research Engineering Co | Fabrication de résines de pétrole polydiéniques |
| US3505300A (en) * | 1968-12-18 | 1970-04-07 | Goodyear Tire & Rubber | Method of refining resins |
| US3692756A (en) * | 1970-07-02 | 1972-09-19 | Goodyear Tire & Rubber | Hydrocarbon-derived resins having low softening point |
| US3855187A (en) * | 1970-08-12 | 1974-12-17 | Exxon Research Engineering Co | Method for preparing resin feed |
| GB1360389A (en) * | 1970-09-07 | 1974-07-17 | Ici Ltd | Synthetic resins derived from petroleum |
| BE792517R (fr) * | 1971-12-15 | 1973-06-08 | Ici Ltd | Resines de |
| JPS55406B2 (en, 2012) * | 1972-07-19 | 1980-01-08 | ||
| GB1392316A (en) * | 1972-10-02 | 1975-04-30 | Ici Ltd | Synthetic resin derived from petroleum |
| IT972795B (it) * | 1972-12-22 | 1974-05-31 | Sir Soc Italiana Resine Spa | Procedimento per la produzione di resine da petrolio |
| GB1486211A (en) * | 1974-03-04 | 1977-09-21 | Exxon Research Engineering Co | Petroleum resins |
-
1975
- 1975-08-13 GB GB33705/75A patent/GB1538057A/en not_active Expired
-
1976
- 1976-08-09 US US05/712,537 patent/US4078132A/en not_active Expired - Lifetime
- 1976-08-11 DE DE19762636187 patent/DE2636187A1/de not_active Withdrawn
- 1976-08-12 IT IT50874/76A patent/IT1062667B/it active
- 1976-08-13 JP JP51096925A patent/JPS5916565B2/ja not_active Expired
- 1976-08-13 NL NLAANVRAGE7609040,A patent/NL188907C/xx not_active IP Right Cessation
- 1976-08-13 FR FR7624827A patent/FR2320959A1/fr active Granted
-
1985
- 1985-04-25 JP JP60089888A patent/JPS61280A/ja active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2835650A (en) * | 1954-07-29 | 1958-05-20 | Exxon Research Engineering Co | Hydrocarbon resins odor stabilized with an alkyl-alkoxy monophenol |
Non-Patent Citations (3)
| Title |
|---|
| Chemiches Zentralblatt, 1968, Ref. 2945 * |
| Hochmolekularbericht 1971, H. 10172/71 * |
| Hochmolekularbericht 1976, H. 2793/76 * |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4100598A1 (de) * | 1991-01-11 | 1992-07-16 | Ruetgerswerke Ag | Verfahren zur herstellung aromatischer kohlenwasserstoff-harze |
| EP3904410A1 (de) * | 2020-04-30 | 2021-11-03 | Rain Carbon Germany GmbH | Kohlenwasserstoffharz und verfahren zu seiner herstellung |
| WO2021219825A1 (de) * | 2020-04-30 | 2021-11-04 | Rain Carbon Germany Gmbh | Kohlenwasserstoffharz und verfahren zu seiner herstellung |
| CN115734976A (zh) * | 2020-04-30 | 2023-03-03 | 莱恩卡本德国有限公司 | 烃类树脂及其生产方法 |
| US11932711B2 (en) | 2020-04-30 | 2024-03-19 | Rain Carbon Germany Gmbh | Hydrocarbon resin and method for production thereof |
| CN115734976B (zh) * | 2020-04-30 | 2024-04-05 | 莱恩卡本德国有限公司 | 烃类树脂及其生产方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5223194A (en) | 1977-02-21 |
| NL188907C (nl) | 1992-11-02 |
| FR2320959A1 (fr) | 1977-03-11 |
| GB1538057A (en) | 1979-01-10 |
| NL188907B (nl) | 1992-06-01 |
| US4078132A (en) | 1978-03-07 |
| JPS61280A (ja) | 1986-01-06 |
| IT1062667B (it) | 1984-10-20 |
| FR2320959B1 (en, 2012) | 1980-08-29 |
| JPS5916565B2 (ja) | 1984-04-16 |
| JPH0326691B2 (en, 2012) | 1991-04-11 |
| NL7609040A (nl) | 1977-02-15 |
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