DE2401149C2 - Addukt aus Maleinsäureanhydrid und einem elastomeren Äthylen-Copolymerisat und dessen Verwendung zur Herstellung von thermoplastischen Elastomeren - Google Patents
Addukt aus Maleinsäureanhydrid und einem elastomeren Äthylen-Copolymerisat und dessen Verwendung zur Herstellung von thermoplastischen ElastomerenInfo
- Publication number
- DE2401149C2 DE2401149C2 DE2401149A DE2401149A DE2401149C2 DE 2401149 C2 DE2401149 C2 DE 2401149C2 DE 2401149 A DE2401149 A DE 2401149A DE 2401149 A DE2401149 A DE 2401149A DE 2401149 C2 DE2401149 C2 DE 2401149C2
- Authority
- DE
- Germany
- Prior art keywords
- adduct
- maleic anhydride
- copolymer
- ethylene copolymer
- vulcanization
- 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
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 title claims description 76
- 229920002725 thermoplastic elastomer Polymers 0.000 title claims description 15
- 229920001038 ethylene copolymer Polymers 0.000 title claims description 8
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- 239000000203 mixture Substances 0.000 claims description 29
- 238000004073 vulcanization Methods 0.000 claims description 26
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- 229910052751 metal Inorganic materials 0.000 claims description 12
- 239000002184 metal Substances 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 9
- AHAREKHAZNPPMI-UHFFFAOYSA-N hexa-1,3-diene Chemical compound CCC=CC=C AHAREKHAZNPPMI-UHFFFAOYSA-N 0.000 claims description 8
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 6
- 229950011008 tetrachloroethylene Drugs 0.000 claims description 6
- 238000009835 boiling Methods 0.000 claims description 4
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 150000007524 organic acids Chemical class 0.000 claims description 3
- 235000005985 organic acids Nutrition 0.000 claims description 3
- 230000000737 periodic effect Effects 0.000 claims description 3
- 150000002989 phenols Chemical class 0.000 claims description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 3
- 150000003573 thiols Chemical class 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 2
- 150000001993 dienes Chemical class 0.000 claims 2
- 229920001577 copolymer Polymers 0.000 description 62
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 42
- 229920001971 elastomer Polymers 0.000 description 33
- 229920000642 polymer Polymers 0.000 description 25
- 150000008064 anhydrides Chemical class 0.000 description 21
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
- 239000005060 rubber Substances 0.000 description 21
- 239000011787 zinc oxide Substances 0.000 description 21
- 239000003795 chemical substances by application Substances 0.000 description 19
- 239000000047 product Substances 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 239000000806 elastomer Substances 0.000 description 12
- 150000003254 radicals Chemical class 0.000 description 12
- 235000021355 Stearic acid Nutrition 0.000 description 10
- 238000004458 analytical method Methods 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 10
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 10
- 239000008117 stearic acid Substances 0.000 description 10
- 239000006229 carbon black Substances 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- -1 zinc oxide Chemical class 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 8
- 238000004898 kneading Methods 0.000 description 8
- 239000000654 additive Substances 0.000 description 7
- 238000004132 cross linking Methods 0.000 description 7
- 239000004071 soot Substances 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- 229910021529 ammonia Inorganic materials 0.000 description 6
- 238000001125 extrusion Methods 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 229910052717 sulfur Inorganic materials 0.000 description 6
- 239000011593 sulfur Substances 0.000 description 6
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 5
- 239000005977 Ethylene Substances 0.000 description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 5
- GUOSQNAUYHMCRU-UHFFFAOYSA-N 11-Aminoundecanoic acid Chemical compound NCCCCCCCCCCC(O)=O GUOSQNAUYHMCRU-UHFFFAOYSA-N 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 239000004927 clay Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 230000002349 favourable effect Effects 0.000 description 4
- 150000002430 hydrocarbons Chemical group 0.000 description 4
- 239000000395 magnesium oxide Substances 0.000 description 4
- 238000006386 neutralization reaction Methods 0.000 description 4
- 229920006029 tetra-polymer Polymers 0.000 description 4
- 229920001169 thermoplastic Polymers 0.000 description 4
- 239000004416 thermosoftening plastic Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 150000001450 anions Chemical class 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000011049 filling Methods 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
- 239000011976 maleic acid Substances 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- 150000001451 organic peroxides Chemical class 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 229930195734 saturated hydrocarbon Natural products 0.000 description 3
- RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical class O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- NHXVNEDMKGDNPR-UHFFFAOYSA-N zinc;pentane-2,4-dione Chemical compound [Zn+2].CC(=O)[CH-]C(C)=O.CC(=O)[CH-]C(C)=O NHXVNEDMKGDNPR-UHFFFAOYSA-N 0.000 description 3
- YPRMWCKXOZFJGF-UHFFFAOYSA-N 3-bromofuran-2,5-dione Chemical compound BrC1=CC(=O)OC1=O YPRMWCKXOZFJGF-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229920002943 EPDM rubber Polymers 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- COZKIZRZDYVVHC-UHFFFAOYSA-N benzene-1,2-diol;zinc Chemical compound [Zn].OC1=CC=CC=C1O COZKIZRZDYVVHC-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 230000006835 compression Effects 0.000 description 2
- 238000007906 compression Methods 0.000 description 2
- 238000000748 compression moulding Methods 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000011888 foil Substances 0.000 description 2
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 2
- 229920000578 graft copolymer Polymers 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 238000001746 injection moulding Methods 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 238000007789 sealing Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000010059 sulfur vulcanization Methods 0.000 description 2
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- YZYKBQUWMPUVEN-UHFFFAOYSA-N zafuleptine Chemical compound OC(=O)CCCCCC(C(C)C)NCC1=CC=C(F)C=C1 YZYKBQUWMPUVEN-UHFFFAOYSA-N 0.000 description 2
- BOXSVZNGTQTENJ-UHFFFAOYSA-L zinc dibutyldithiocarbamate Chemical compound [Zn+2].CCCCN(C([S-])=S)CCCC.CCCCN(C([S-])=S)CCCC BOXSVZNGTQTENJ-UHFFFAOYSA-L 0.000 description 2
- BHMLFPOTZYRDKA-IRXDYDNUSA-N (2s)-2-[(s)-(2-iodophenoxy)-phenylmethyl]morpholine Chemical compound IC1=CC=CC=C1O[C@@H](C=1C=CC=CC=1)[C@H]1OCCNC1 BHMLFPOTZYRDKA-IRXDYDNUSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
- QTYUSOHYEPOHLV-FNORWQNLSA-N 1,3-Octadiene Chemical compound CCCC\C=C\C=C QTYUSOHYEPOHLV-FNORWQNLSA-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
- QUVMSYUGOKEMPX-UHFFFAOYSA-N 2-methylpropan-1-olate;titanium(4+) Chemical compound [Ti+4].CC(C)C[O-].CC(C)C[O-].CC(C)C[O-].CC(C)C[O-] QUVMSYUGOKEMPX-UHFFFAOYSA-N 0.000 description 1
- HXIQYSLFEXIOAV-UHFFFAOYSA-N 2-tert-butyl-4-(5-tert-butyl-4-hydroxy-2-methylphenyl)sulfanyl-5-methylphenol Chemical compound CC1=CC(O)=C(C(C)(C)C)C=C1SC1=CC(C(C)(C)C)=C(O)C=C1C HXIQYSLFEXIOAV-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- ULKFLOVGORAZDI-UHFFFAOYSA-N 3,3-dimethyloxetan-2-one Chemical compound CC1(C)COC1=O ULKFLOVGORAZDI-UHFFFAOYSA-N 0.000 description 1
- AGULWIQIYWWFBJ-UHFFFAOYSA-N 3,4-dichlorofuran-2,5-dione Chemical compound ClC1=C(Cl)C(=O)OC1=O AGULWIQIYWWFBJ-UHFFFAOYSA-N 0.000 description 1
- XBIUWALDKXACEA-UHFFFAOYSA-N 3-[bis(2,4-dioxopentan-3-yl)alumanyl]pentane-2,4-dione Chemical compound CC(=O)C(C(C)=O)[Al](C(C(C)=O)C(C)=O)C(C(C)=O)C(C)=O XBIUWALDKXACEA-UHFFFAOYSA-N 0.000 description 1
- CXWBKBJQRJQRKC-UHFFFAOYSA-N 3-bromooxolane-2,5-dione Chemical compound BrC1CC(=O)OC1=O CXWBKBJQRJQRKC-UHFFFAOYSA-N 0.000 description 1
- SLXKOJJOQWFEFD-UHFFFAOYSA-N 6-aminohexanoic acid Chemical compound NCCCCCC(O)=O SLXKOJJOQWFEFD-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 241000221020 Hevea Species 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 229910017976 MgO 4 Inorganic materials 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
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- 229910010413 TiO 2 Inorganic materials 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 229960002684 aminocaproic acid Drugs 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- HQMRIBYCTLBDAK-UHFFFAOYSA-M bis(2-methylpropyl)alumanylium;chloride Chemical compound CC(C)C[Al](Cl)CC(C)C HQMRIBYCTLBDAK-UHFFFAOYSA-M 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
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- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- YCIMNLLNPGFGHC-UHFFFAOYSA-L catecholate(2-) Chemical compound [O-]C1=CC=CC=C1[O-] YCIMNLLNPGFGHC-UHFFFAOYSA-L 0.000 description 1
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- LZKLAOYSENRNKR-LNTINUHCSA-N iron;(z)-4-oxoniumylidenepent-2-en-2-olate Chemical compound [Fe].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O LZKLAOYSENRNKR-LNTINUHCSA-N 0.000 description 1
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- 230000006855 networking Effects 0.000 description 1
- BMGNSKKZFQMGDH-FDGPNNRMSA-L nickel(2+);(z)-4-oxopent-2-en-2-olate Chemical compound [Ni+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O BMGNSKKZFQMGDH-FDGPNNRMSA-L 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 description 1
- XZZXKVYTWCYOQX-UHFFFAOYSA-J octanoate;tin(4+) Chemical compound [Sn+4].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O.CCCCCCCC([O-])=O.CCCCCCCC([O-])=O XZZXKVYTWCYOQX-UHFFFAOYSA-J 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
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- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid group Chemical group C(CCC(=O)O)(=O)O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- JBIQAPKSNFTACH-UHFFFAOYSA-K vanadium oxytrichloride Chemical compound Cl[V](Cl)(Cl)=O JBIQAPKSNFTACH-UHFFFAOYSA-K 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
- 229940006486 zinc cation Drugs 0.000 description 1
- ZUBNXRHITOZMOO-UHFFFAOYSA-N zinc;octadecanoic acid;oxygen(2-) Chemical compound [O-2].[Zn+2].CCCCCCCCCCCCCCCCCC(O)=O ZUBNXRHITOZMOO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L55/00—Compositions of homopolymers or copolymers, obtained by polymerisation reactions only involving carbon-to-carbon unsaturated bonds, not provided for in groups C08L23/00 - C08L53/00
- C08L55/04—Polyadducts obtained by the diene synthesis
-
- 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
- C08F8/00—Chemical modification by after-treatment
- C08F8/12—Hydrolysis
-
- 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
- C08F8/00—Chemical modification by after-treatment
- C08F8/46—Reaction with unsaturated dicarboxylic acids or anhydrides thereof, e.g. maleinisation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
- C08L23/26—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers modified by chemical after-treatment
-
- 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
- C08F2800/00—Copolymer characterised by the proportions of the comonomers expressed
- C08F2800/20—Copolymer characterised by the proportions of the comonomers expressed as weight or mass percentages
-
- 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
- C08F2810/00—Chemical modification of a polymer
- C08F2810/20—Chemical modification of a polymer leading to a crosslinking, either explicitly or inherently
-
- 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
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S266/00—Metallurgical apparatus
- Y10S266/903—Safety shields
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Paints Or Removers (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US322360A US3884882A (en) | 1973-01-10 | 1973-01-10 | Certain EPDM copolymer/maleic anhydride adducts and thermoplastic elastomers therefrom |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2401149A1 DE2401149A1 (de) | 1974-07-18 |
| DE2401149C2 true DE2401149C2 (de) | 1986-03-13 |
Family
ID=23254541
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2401149A Expired DE2401149C2 (de) | 1973-01-10 | 1974-01-10 | Addukt aus Maleinsäureanhydrid und einem elastomeren Äthylen-Copolymerisat und dessen Verwendung zur Herstellung von thermoplastischen Elastomeren |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3884882A (en, 2012) |
| JP (2) | JPS5243677B2 (en, 2012) |
| CA (1) | CA1032688A (en, 2012) |
| DE (1) | DE2401149C2 (en, 2012) |
| FR (1) | FR2323708A1 (en, 2012) |
| GB (1) | GB1436981A (en, 2012) |
| IT (1) | IT1006834B (en, 2012) |
| NL (1) | NL7400353A (en, 2012) |
Families Citing this family (79)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3997487A (en) * | 1973-10-12 | 1976-12-14 | E. I. Du Pont De Nemours And Company | Thermoplastic elastomer |
| US4026967A (en) * | 1976-06-25 | 1977-05-31 | E. I. Du Pont De Nemours And Company | Process for making grafted polymeric material |
| JPS53111390A (en) * | 1977-03-10 | 1978-09-28 | Nitto Electric Ind Co Ltd | Modification of olefin terpolymer |
| US4320019A (en) | 1978-04-17 | 1982-03-16 | The Lubrizol Corporation | Multi-purpose additive compositions and concentrates containing same |
| US4230830A (en) * | 1979-03-30 | 1980-10-28 | E. I. Du Pont De Nemours And Company | Adhesive blends containing thermally grafted ethylene polymer |
| IT1112946B (it) * | 1979-04-04 | 1986-01-20 | Anic Spa | Processo per la preparazione di copolimeri graffati di alfa sostituiti da beta propiolattone su eptm |
| IT1165058B (it) * | 1979-05-14 | 1987-04-22 | Anic Spa | Processo per la preparazione di polimeri graffati di alfa,alfa' disostituiti beta-propiolattoni su copolieri a base di isobutilene e trieni |
| US4251424A (en) * | 1979-08-30 | 1981-02-17 | E. I. Du Pont De Nemours And Company | Plasticized nylon 612 with improved zinc chloride resistance |
| US4283317A (en) * | 1980-09-15 | 1981-08-11 | E. I. Du Pont De Nemours And Company | Wax-free, hot melt adhesive compositions |
| JPS5876005U (ja) * | 1981-11-18 | 1983-05-23 | 松下精工株式会社 | 電気スト−ブの反射板固定装置 |
| DE3306008A1 (de) * | 1983-02-22 | 1984-08-23 | Chemische Werke Hüls AG, 4370 Marl | Kaelteschlagzaehe, thermoplastisch verarbeitbare formmasse aus poly(butylenterephthalat) |
| US4589804A (en) * | 1983-03-28 | 1986-05-20 | Uniroyal Chemical Company, Inc. | Method for waterproofing surfaces |
| US4670515A (en) * | 1983-08-15 | 1987-06-02 | Copolymer Rubber & Chemical Corp. | Grafted and cross-linked epm |
| DE3335706A1 (de) * | 1983-10-01 | 1985-04-11 | Chemische Werke Hüls AG, 4370 Marl | Verfahren zur herstellung eines funktionalisierten poly-(alpha)-olefinkautschuks und seine verwendung zur herstellung von schlagzaehen, thermoplastischen massen |
| US4739016A (en) * | 1984-06-11 | 1988-04-19 | Uniroyal Chemical Company, Inc. | Modified ionic elastomer and blend with nylon |
| US4544702A (en) * | 1984-06-11 | 1985-10-01 | Uniroyal, Inc. | Modified ionic elastomer and blend with nylon |
| JPS61148262A (ja) * | 1984-12-21 | 1986-07-05 | Polyplastics Co | ポリブチレンテレフタレ−ト樹脂組成物 |
| US4798874A (en) * | 1985-12-23 | 1989-01-17 | General Electric Company | Thermoplastic blends comprising polycarbonate resin and amorphous polyamide |
| JPS62121755U (en, 2012) * | 1986-01-24 | 1987-08-01 | ||
| US5006603A (en) * | 1986-09-26 | 1991-04-09 | Ube Industries, Ltd. | Fiber-reinforced rubber composition and production process and use thereof |
| US5194509A (en) * | 1986-11-20 | 1993-03-16 | Basf Aktiengesellschaft | Peroxide-free grafting of homopolymers and copolymers of ethylene having densities equal to or greater than 0.930 g/cm3, and use of the graft copolymers for the preparation of ionomers of adhesion promoters |
| US5189120A (en) * | 1986-11-20 | 1993-02-23 | Basf Aktiengesellschaft | Peroxide-free grafting of homopolymers and copolymers of ethylene having densities less than 0.930 g/cm3, and use of the graft copolymers for the preparation of ionomers or adhesion promoters |
| US4965111A (en) * | 1987-01-16 | 1990-10-23 | General Electric Company | Olefinic impact modifiers for, and blends with, thermoplastic polyester resins |
| US5179169A (en) * | 1987-01-16 | 1993-01-12 | Copolymer Rubber & Chemical Corporation | Olefinic impact modifiers for, and blends with, thermoplastic polyester resins |
| US5244972A (en) * | 1987-01-16 | 1993-09-14 | General Electric Company | Single step bulk process for high impact polyester masterbatches, products thereof and blends with polyesters |
| US5151466A (en) * | 1987-01-16 | 1992-09-29 | Phadke Shrikant V | Single step bulk process for high impact polyester masterbatches, products thereof and blends with polyesters |
| US4863999A (en) * | 1987-08-12 | 1989-09-05 | Pennwalt Corporation | Multipurpose polymer bound stabilizers |
| US5096974A (en) * | 1987-08-12 | 1992-03-17 | Atochem North America, Inc. | Process for preparing multipurpose polymer bound stabilizers and polymer bound stabilizer produced thereby |
| US4868246A (en) * | 1987-08-12 | 1989-09-19 | Pennwalt Corporation | Polymer bound UV stabilizers |
| US4866136A (en) * | 1987-08-12 | 1989-09-12 | Pennwalt Corporation | Process for producing polymer bound hindered amine light stabilizers |
| US4981914A (en) * | 1987-08-12 | 1991-01-01 | Atochem North America, Inc. | Polymer bound UV stabilizers |
| US4857595A (en) * | 1987-08-12 | 1989-08-15 | Pennwalt Corporation | Polymer bound hindered amine light stabilizers |
| US4975489A (en) * | 1987-08-12 | 1990-12-04 | Atochem North America, Inc. | Process for preparing polymer bound hindered amine light stabilizers |
| US4981915A (en) * | 1987-08-12 | 1991-01-01 | Atochem North America, Inc. | Multipurpose polymer bound stabilizers |
| US5206378A (en) * | 1987-08-12 | 1993-04-27 | Elf Atochem North America, Inc. | Hydrazido functionalized 2-(2-hydroxyphenyl)-2h-benzotriazoles |
| US5096977A (en) * | 1987-08-12 | 1992-03-17 | Atochem North America, Inc. | Process for preparing polymer bound UV stabilizers |
| JPH01306204A (ja) * | 1988-06-04 | 1989-12-11 | Fuji Slate Kk | 厚型スレートの成型金型 |
| US4956416A (en) * | 1988-08-18 | 1990-09-11 | Atochem North America, Inc. | Amino or hydrazino peroxides, derivatives and their uses |
| US5272219A (en) * | 1988-08-18 | 1993-12-21 | Elf Atochem North America, Inc. | Process for preparing amino or hydrazino peroxides, derivatives and their uses |
| US5140070A (en) * | 1988-11-07 | 1992-08-18 | Elf Atochem North America, Inc | Compositions comprising polymer bond flame retardants |
| US5220015A (en) * | 1988-11-07 | 1993-06-15 | Elf Atochem North America, Inc. | Flame retardants compounds |
| US5037894A (en) * | 1988-11-07 | 1991-08-06 | Atochem North America, Inc. | Polymer bound flame retardants |
| US5177149A (en) * | 1988-11-23 | 1993-01-05 | General Electric Company | Thermoplastic blends of amorphous polyamides and poly(alkenyl aromatic) resins |
| DE3911695A1 (de) * | 1989-04-10 | 1990-10-11 | Inventa Ag | Verbundwerkstoffe und ihre verwendung |
| DE3943280A1 (de) * | 1989-12-29 | 1991-07-04 | Huels Chemische Werke Ag | Additionsprodukte aus polyoctenylen und maleinsaeureanhydrid bzw. einem fumarsaeuredialkylester, verfahren zu deren herstellung sowie deren verwendung |
| CA2061474C (en) | 1991-02-22 | 2002-03-26 | Kenneth Benjamin Higgins | Bitumen backed carpet tile |
| EP0503909A1 (en) * | 1991-03-14 | 1992-09-16 | Chevron Research And Technology Company | Substantially non-crosslinked maleic anhydride-modified ethylene polymers and process for preparing same |
| US5244971A (en) * | 1991-07-22 | 1993-09-14 | Exxon Chemical Patents Inc. | Graft polymers for use in engineering thermoplastic blends |
| DE4308591A1 (de) * | 1993-03-18 | 1994-09-22 | Basf Ag | Gepfropfte Propylencopolymerisate |
| US5346963A (en) * | 1993-04-28 | 1994-09-13 | The Dow Chemical Company | Graft-modified, substantially linear ethylene polymers and methods for their use |
| DE4342605A1 (de) * | 1993-12-14 | 1995-06-22 | Buna Gmbh | Funktionalisierte Olefinhomo- und -copolymere |
| CA2222833A1 (en) | 1997-11-28 | 1999-05-28 | Brent R. Stranix | Functional polymers bearing non-metal oxyacid derivatives on dimethylene spacers |
| CA2222837A1 (en) | 1997-11-28 | 1999-05-28 | Brent R. Stranix | Cycloaddition functional polymers from (vinyl)polystyrene |
| FR2779731B1 (fr) * | 1998-06-11 | 2000-08-11 | Hutchinson | Composition d'elastomere a base d'epdm et courroie de transmission de puissance realisee essentiellement en cet elastomere |
| US6437054B1 (en) | 1999-02-17 | 2002-08-20 | General Electric Company | Composition of polyester sulfonate salt ionomer, polyamide and polyepoxide |
| BE1012637A3 (fr) * | 1999-04-29 | 2001-01-09 | Solvay | Polyolefines et procede pour leur fabrication. |
| US6365677B1 (en) | 2000-03-01 | 2002-04-02 | General Electric | Reduction of carbonized particles |
| US6482879B2 (en) | 2000-04-17 | 2002-11-19 | General Electric Company | Composition for laser marking |
| US7022776B2 (en) * | 2001-11-07 | 2006-04-04 | General Electric | Conductive polyphenylene ether-polyamide composition, method of manufacture thereof, and article derived therefrom |
| US6858671B2 (en) * | 2001-12-04 | 2005-02-22 | General Electric Company | Method of manufacture of polyester molding compositions and articles produced therefrom |
| US6776929B2 (en) * | 2002-03-15 | 2004-08-17 | General Electric Company | Method of forming a conductive thermoplastic composition |
| US6887940B2 (en) * | 2002-11-27 | 2005-05-03 | Basell Poliolefine Italia S.P.A. | Compatibilizing agent for engineering thermoplastic/polyolefin blend |
| US7241403B2 (en) * | 2003-05-29 | 2007-07-10 | General Electric Company | Method for making a conductive thermoplastic composition |
| US20070010641A1 (en) * | 2003-08-07 | 2007-01-11 | Ashok Adur | Catalyst systems for elastomeric compositions |
| US7803856B2 (en) * | 2004-05-04 | 2010-09-28 | Sabic Innovative Plastics Ip B.V. | Halogen-free flame retardant polyamide composition with improved electrical and flammability properties |
| CA2511002C (en) * | 2004-07-06 | 2012-10-23 | Minh-Tan Ton-That | Hot-melt adhesive |
| US20070213475A1 (en) * | 2004-07-29 | 2007-09-13 | Solvay Advanced Polymers, L.L..C | Impact Modified Polyamide Compositions |
| US7230066B2 (en) * | 2004-12-16 | 2007-06-12 | General Electric Company | Polycarbonate—ultem block copolymers |
| CN101175791B (zh) * | 2005-03-18 | 2011-01-26 | 可乐丽股份有限公司 | 半芳族聚酰胺树脂 |
| US20070293626A1 (en) * | 2005-12-07 | 2007-12-20 | Shreyas Chakravarti | Polyamide blend compositions |
| US20070135586A1 (en) * | 2005-12-09 | 2007-06-14 | Shreyas Chakravarti | Polyamide blend compositions formed article and process thereof |
| US7423080B2 (en) * | 2006-03-03 | 2008-09-09 | Sabic Innovative Plastics Ip B.V. | Radiation crosslinking of halogen-free flame retardant polymer |
| JP2008162401A (ja) | 2006-12-28 | 2008-07-17 | Kyosan Denki Co Ltd | 樹脂タンク溶着部材 |
| US20090134370A1 (en) * | 2007-07-20 | 2009-05-28 | Herve Cartier | Conductive halogen free flame retardant thermoplastic composition |
| US20090030141A1 (en) * | 2007-07-23 | 2009-01-29 | Kim Gene Balfour | Poly(arylene ether) composition, method, and article |
| WO2013175452A1 (en) | 2012-05-24 | 2013-11-28 | Sabic Innovative Plastics Ip B.V. | Improved flame retardant polymer compositions |
| US20180237570A1 (en) * | 2017-02-17 | 2018-08-23 | Equistar Chemicals, Lp | Process for lowering yellowness index of polyolefin-based maleic anhydride graft copolymers and compositions made therefrom |
| WO2021162938A1 (en) | 2020-02-10 | 2021-08-19 | Sirrus, Inc. | Copolymers of dicarbonyl substituted-1-alkene and olefins and methods to make them |
| CN112300330A (zh) * | 2020-10-23 | 2021-02-02 | 无锡市锡山新材料科技有限公司 | 一种三元乙丙橡胶板的制备方法 |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2608550A (en) * | 1947-01-08 | 1952-08-26 | Interchem Corp | Reaction products of unsaturated dicarboxylic acid derivatives with cyclopentadiene polymers |
| US2844502A (en) * | 1954-08-31 | 1958-07-22 | Us Rubber Co | Method of bonding elastomers to other materials and adhesive compositions used therefor |
| US2933480A (en) * | 1959-06-17 | 1960-04-19 | Du Pont | Sulfur vulcanizable unsaturated elastomeric interpolymers of monoolefins and diolefins |
| BR6237778D0 (pt) * | 1961-04-12 | 1973-01-11 | W Taban | Processo continuo para produzir um poli-etileno modificado por um composto de acido maleico solido e poli-etileno modificado por composto de acido maleico solido |
| BE623698A (en, 2012) * | 1961-10-18 | 1963-02-15 | Montecatina Societa Generale P | |
| US3231498A (en) * | 1963-03-28 | 1966-01-25 | Chevron Res | Lubricants containing high molecular weight succinic acid compound |
| FR1378045A (fr) * | 1963-06-04 | 1964-11-13 | Aquitaine Petrole | Modification de polyodéfines |
| GB1093794A (en) * | 1964-04-14 | 1967-12-06 | Montedison Spa | Bonding elastomeric copolymers on to articles |
| LU46240A1 (en, 2012) * | 1964-06-03 | 1964-12-03 | ||
| US3240762A (en) * | 1965-04-09 | 1966-03-15 | Velsicol Chemical Corp | Maleic anhydride hydrogenated polycyclopentadiene reaction products |
| DE1669829A1 (de) * | 1966-03-17 | 1969-10-23 | Ceskoslovenske Zd Y Gumarenske | Verfahren zur Herstellung von Polyurethan-Harnstoffloesungen |
| DE1595695A1 (de) * | 1966-04-14 | 1970-03-12 | Hoechst Ag | Verfahren zur Herstellung von Mischpolymerisaten aus AEthylen,Propylen und 5-AEthyliden-2-norbornen |
| NL6607078A (en, 2012) * | 1966-05-24 | 1967-11-27 | ||
| DE1669826A1 (de) * | 1967-02-01 | 1971-07-01 | Huels Chemische Werke Ag | Verfahren zum Vulkanisieren von Terpolymeren aus AEthylen,einem oder mehreren alpha-Olefinen und mindestens einem Multien |
| US3403011A (en) * | 1967-06-20 | 1968-09-24 | Texaco Inc | Middle distillate fuel composition |
| GB1204729A (en) * | 1967-12-28 | 1970-09-09 | Shell Int Research | Process for the improvement of synthetic diene polymers |
| GB1158980A (en) * | 1968-07-04 | 1969-07-23 | Shell Int Research | A Process for preparing a Novel Thermoplastic Rubber and a novel Thermoplastic Rubber |
| BE786747A (fr) * | 1971-07-26 | 1973-01-26 | Du Pont | Copolymeres greffes statistiques de pivalolactones |
-
1973
- 1973-01-10 US US322360A patent/US3884882A/en not_active Ceased
-
1974
- 1974-01-08 JP JP49005121A patent/JPS5243677B2/ja not_active Expired
- 1974-01-09 IT IT19249/74A patent/IT1006834B/it active
- 1974-01-09 FR FR7400701A patent/FR2323708A1/fr active Granted
- 1974-01-09 GB GB103174A patent/GB1436981A/en not_active Expired
- 1974-01-09 CA CA189,791A patent/CA1032688A/en not_active Expired
- 1974-01-10 NL NL7400353A patent/NL7400353A/xx not_active Application Discontinuation
- 1974-01-10 DE DE2401149A patent/DE2401149C2/de not_active Expired
-
1977
- 1977-06-08 JP JP6680977A patent/JPS531288A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| FR2323708A1 (fr) | 1977-04-08 |
| DE2401149A1 (de) | 1974-07-18 |
| JPS5243677B2 (en, 2012) | 1977-11-01 |
| CA1032688A (en) | 1978-06-06 |
| JPS49104992A (en, 2012) | 1974-10-04 |
| IT1006834B (it) | 1976-10-20 |
| FR2323708B1 (en, 2012) | 1978-03-24 |
| JPS5319351B2 (en, 2012) | 1978-06-20 |
| US3884882A (en) | 1975-05-20 |
| NL7400353A (en, 2012) | 1974-07-12 |
| JPS531288A (en) | 1978-01-09 |
| GB1436981A (en) | 1976-05-26 |
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