DE1645358A1 - Verfahren zur Herstellung von Urethanelastomeren - Google Patents
Verfahren zur Herstellung von UrethanelastomerenInfo
- Publication number
- DE1645358A1 DE1645358A1 DE19661645358 DE1645358A DE1645358A1 DE 1645358 A1 DE1645358 A1 DE 1645358A1 DE 19661645358 DE19661645358 DE 19661645358 DE 1645358 A DE1645358 A DE 1645358A DE 1645358 A1 DE1645358 A1 DE 1645358A1
- Authority
- DE
- Germany
- Prior art keywords
- urethane
- polymer
- oil
- diene
- parts
- 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- Withdrawn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
- 229920006311 Urethane elastomer Polymers 0.000 title claims description 27
- 238000000034 method Methods 0.000 title claims description 20
- 230000008569 process Effects 0.000 title claims description 5
- 239000003921 oil Substances 0.000 claims description 114
- 229920000642 polymer Polymers 0.000 claims description 110
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 107
- 229920001971 elastomer Polymers 0.000 claims description 91
- 150000001993 dienes Chemical class 0.000 claims description 58
- 239000000806 elastomer Substances 0.000 claims description 46
- 239000005060 rubber Substances 0.000 claims description 44
- KAKZBPTYRLMSJV-UHFFFAOYSA-N butadiene group Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 36
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 35
- 229920000728 polyester Polymers 0.000 claims description 25
- 239000004606 Fillers/Extenders Substances 0.000 claims description 24
- 239000000178 monomer Substances 0.000 claims description 21
- 239000006229 carbon black Substances 0.000 claims description 19
- 150000002430 hydrocarbons Chemical class 0.000 claims description 19
- 229930195733 hydrocarbon Natural products 0.000 claims description 18
- 238000004519 manufacturing process Methods 0.000 claims description 18
- -1 1,3-diene hydrocarbon Chemical class 0.000 claims description 16
- 239000004215 Carbon black (E152) Substances 0.000 claims description 16
- 125000005442 diisocyanate group Chemical group 0.000 claims description 15
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 14
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 12
- 239000007787 solid Substances 0.000 claims description 10
- 125000000746 allylic group Chemical group 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 229920001228 polyisocyanate Polymers 0.000 claims description 7
- 239000005056 polyisocyanate Substances 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 239000004202 carbamide Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 239000012467 final product Substances 0.000 claims description 2
- 150000005673 monoalkenes Chemical class 0.000 claims description 2
- 239000002480 mineral oil Substances 0.000 claims 2
- 235000010446 mineral oil Nutrition 0.000 claims 2
- HOSGXJWQVBHGLT-UHFFFAOYSA-N 6-hydroxy-3,4-dihydro-1h-quinolin-2-one Chemical group N1C(=O)CCC2=CC(O)=CC=C21 HOSGXJWQVBHGLT-UHFFFAOYSA-N 0.000 claims 1
- 102100032578 Adenosine deaminase domain-containing protein 1 Human genes 0.000 claims 1
- 101000797006 Homo sapiens Adenosine deaminase domain-containing protein 1 Proteins 0.000 claims 1
- 241000607479 Yersinia pestis Species 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- 235000019198 oils Nutrition 0.000 description 112
- 239000000463 material Substances 0.000 description 59
- 239000000203 mixture Substances 0.000 description 49
- 239000005062 Polybutadiene Substances 0.000 description 34
- 229920002857 polybutadiene Polymers 0.000 description 34
- 238000006243 chemical reaction Methods 0.000 description 33
- 229920001519 homopolymer Polymers 0.000 description 32
- 229920001577 copolymer Polymers 0.000 description 30
- 239000000047 product Substances 0.000 description 30
- 239000007788 liquid Substances 0.000 description 27
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 27
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 24
- 230000000704 physical effect Effects 0.000 description 23
- 229920000570 polyether Polymers 0.000 description 21
- 238000006116 polymerization reaction Methods 0.000 description 21
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 19
- 239000012948 isocyanate Substances 0.000 description 19
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 19
- 150000002513 isocyanates Chemical class 0.000 description 18
- 239000011347 resin Substances 0.000 description 16
- 229920005989 resin Polymers 0.000 description 16
- 239000000945 filler Substances 0.000 description 15
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 14
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 13
- OYQYHJRSHHYEIG-UHFFFAOYSA-N ethyl carbamate;urea Chemical compound NC(N)=O.CCOC(N)=O OYQYHJRSHHYEIG-UHFFFAOYSA-N 0.000 description 13
- 150000004985 diamines Chemical class 0.000 description 12
- 239000000377 silicon dioxide Substances 0.000 description 12
- 239000003054 catalyst Substances 0.000 description 10
- 229920001451 polypropylene glycol Polymers 0.000 description 10
- 230000008901 benefit Effects 0.000 description 9
- 239000004071 soot Substances 0.000 description 9
- 229910052717 sulfur Inorganic materials 0.000 description 9
- 239000011593 sulfur Substances 0.000 description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 8
- 238000004132 cross linking Methods 0.000 description 8
- 229920001194 natural rubber Polymers 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 150000003673 urethanes Chemical class 0.000 description 8
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 7
- 239000010426 asphalt Substances 0.000 description 7
- 239000012975 dibutyltin dilaurate Substances 0.000 description 7
- 229920003052 natural elastomer Polymers 0.000 description 7
- 229920001195 polyisoprene Polymers 0.000 description 7
- 244000043261 Hevea brasiliensis Species 0.000 description 6
- 239000004721 Polyphenylene oxide Substances 0.000 description 6
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- 150000002334 glycols Chemical class 0.000 description 6
- 150000002978 peroxides Chemical class 0.000 description 6
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 238000010790 dilution Methods 0.000 description 5
- 239000012895 dilution Substances 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 230000003301 hydrolyzing effect Effects 0.000 description 5
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 5
- 229910052740 iodine Inorganic materials 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- 229920001083 polybutene Polymers 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- 230000002787 reinforcement Effects 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 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 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000003963 antioxidant agent Substances 0.000 description 4
- 150000001721 carbon Chemical group 0.000 description 4
- 239000003431 cross linking reagent Substances 0.000 description 4
- 239000011630 iodine Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 229920002587 poly(1,3-butadiene) polymer Polymers 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 239000004970 Chain extender Substances 0.000 description 3
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229920000459 Nitrile rubber Polymers 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 230000003078 antioxidant effect Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 230000009969 flowable effect Effects 0.000 description 3
- 238000005755 formation reaction Methods 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229920003225 polyurethane elastomer Polymers 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 230000000717 retained effect Effects 0.000 description 3
- 238000004448 titration Methods 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- 239000011787 zinc oxide Substances 0.000 description 3
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 2
- LRRMGPGVHYPBPL-UHFFFAOYSA-N 2,6-ditert-butyl-4-[2-(3,5-ditert-butyl-4-hydroxyphenyl)ethyl]phenol Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 LRRMGPGVHYPBPL-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 2
- HUWXDEQWWKGHRV-UHFFFAOYSA-N 3,3'-Dichlorobenzidine Chemical compound C1=C(Cl)C(N)=CC=C1C1=CC=C(N)C(Cl)=C1 HUWXDEQWWKGHRV-UHFFFAOYSA-N 0.000 description 2
- IBOFVQJTBBUKMU-UHFFFAOYSA-N 4,4'-methylene-bis-(2-chloroaniline) Chemical compound C1=C(Cl)C(N)=CC=C1CC1=CC=C(N)C(Cl)=C1 IBOFVQJTBBUKMU-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 229920013646 Hycar Polymers 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 2
- 241001112258 Moca Species 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 229920002367 Polyisobutene Polymers 0.000 description 2
- GCTFWCDSFPMHHS-UHFFFAOYSA-M Tributyltin chloride Chemical compound CCCC[Sn](Cl)(CCCC)CCCC GCTFWCDSFPMHHS-UHFFFAOYSA-M 0.000 description 2
- 238000005299 abrasion Methods 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical group 0.000 description 2
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- NTXGQCSETZTARF-UHFFFAOYSA-N buta-1,3-diene;prop-2-enenitrile Chemical compound C=CC=C.C=CC#N NTXGQCSETZTARF-UHFFFAOYSA-N 0.000 description 2
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 230000001055 chewing effect Effects 0.000 description 2
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 description 2
- 239000003245 coal Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- 239000013536 elastomeric material Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 230000035515 penetration Effects 0.000 description 2
- 239000011295 pitch Substances 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- 229920000412 polyarylene Polymers 0.000 description 2
- 229920000151 polyglycol Polymers 0.000 description 2
- 239000010695 polyglycol Substances 0.000 description 2
- 230000000379 polymerizing effect Effects 0.000 description 2
- 229920000098 polyolefin Chemical group 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 239000012744 reinforcing agent Substances 0.000 description 2
- 230000003014 reinforcing effect Effects 0.000 description 2
- 239000003566 sealing material Substances 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 238000010186 staining Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 229920003051 synthetic elastomer Polymers 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- 238000004073 vulcanization Methods 0.000 description 2
- PCTMTFRHKVHKIS-BMFZQQSSSA-N (1s,3r,4e,6e,8e,10e,12e,14e,16e,18s,19r,20r,21s,25r,27r,30r,31r,33s,35r,37s,38r)-3-[(2r,3s,4s,5s,6r)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-19,25,27,30,31,33,35,37-octahydroxy-18,20,21-trimethyl-23-oxo-22,39-dioxabicyclo[33.3.1]nonatriaconta-4,6,8,10 Chemical compound C1C=C2C[C@@H](OS(O)(=O)=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2.O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 PCTMTFRHKVHKIS-BMFZQQSSSA-N 0.000 description 1
- RHLWQEFHFQTKNT-UHFFFAOYSA-N (2z)-1-cyclooctyl-2-diazocyclooctane Chemical compound [N-]=[N+]=C1CCCCCCC1C1CCCCCCC1 RHLWQEFHFQTKNT-UHFFFAOYSA-N 0.000 description 1
- MTZUIIAIAKMWLI-UHFFFAOYSA-N 1,2-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC=C1N=C=O MTZUIIAIAKMWLI-UHFFFAOYSA-N 0.000 description 1
- ZXHZWRZAWJVPIC-UHFFFAOYSA-N 1,2-diisocyanatonaphthalene Chemical compound C1=CC=CC2=C(N=C=O)C(N=C=O)=CC=C21 ZXHZWRZAWJVPIC-UHFFFAOYSA-N 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- KPAPHODVWOVUJL-UHFFFAOYSA-N 1-benzofuran;1h-indene Chemical compound C1=CC=C2CC=CC2=C1.C1=CC=C2OC=CC2=C1 KPAPHODVWOVUJL-UHFFFAOYSA-N 0.000 description 1
- DIPUOCQXXYYIJO-UHFFFAOYSA-N 1-n,2-n-bis(5-methylhexan-2-yl)benzene-1,2-diamine Chemical compound CC(C)CCC(C)NC1=CC=CC=C1NC(C)CCC(C)C DIPUOCQXXYYIJO-UHFFFAOYSA-N 0.000 description 1
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 1
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- UIFVCPMLQXKEEU-UHFFFAOYSA-N 2,3-dimethylbenzaldehyde Chemical compound CC1=CC=CC(C=O)=C1C UIFVCPMLQXKEEU-UHFFFAOYSA-N 0.000 description 1
- ZDXGQHXSMPGQRI-UHFFFAOYSA-N 2,6-ditert-butyl-3-[(2,4-ditert-butyl-3-hydroxyphenyl)methyl]phenol Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC=C1CC1=CC=C(C(C)(C)C)C(O)=C1C(C)(C)C ZDXGQHXSMPGQRI-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 1
- LEKIODFWYFCUER-UHFFFAOYSA-N 2-methylidenebut-3-enenitrile Chemical compound C=CC(=C)C#N LEKIODFWYFCUER-UHFFFAOYSA-N 0.000 description 1
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- A61F5/44—Devices worn by the patient for reception of urine, faeces, catamenial or other discharge; Colostomy devices
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- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
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- C08C19/30—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule
- C08C19/34—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule reacting with oxygen or oxygen-containing groups
- C08C19/38—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule reacting with oxygen or oxygen-containing groups with hydroxy radicals
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/67—Unsaturated compounds having active hydrogen
- C08G18/69—Polymers of conjugated dienes
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
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- C08G18/83—Chemically modified polymers
- C08G18/87—Chemically modified polymers by sulfur
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- C—CHEMISTRY; METALLURGY
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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- C—CHEMISTRY; METALLURGY
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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- C08L2555/24—Asphalt produced between 100°C and 140°C, e.g. warm mix asphalt
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- C—CHEMISTRY; METALLURGY
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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- 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
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- 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
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- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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Landscapes
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- Chemical Kinetics & Catalysis (AREA)
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- Civil Engineering (AREA)
- Materials Engineering (AREA)
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- Polyurethanes Or Polyureas (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US46516165A | 1965-06-18 | 1965-06-18 | |
| US53629266A | 1966-03-22 | 1966-03-22 | |
| US53630166A | 1966-03-22 | 1966-03-22 | |
| US71354368A | 1968-03-15 | 1968-03-15 | |
| US79734769A | 1969-01-23 | 1969-01-23 | |
| US10905971A | 1971-01-22 | 1971-01-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1645358A1 true DE1645358A1 (de) | 1970-09-24 |
Family
ID=27557759
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661645358 Withdrawn DE1645358A1 (de) | 1965-06-18 | 1966-06-18 | Verfahren zur Herstellung von Urethanelastomeren |
| DE1694887A Expired DE1694887C3 (de) | 1965-06-18 | 1966-06-18 | Polymerenverschnitte, bestehend aus Kohlenwasserstoffkautschuk und Polyurethan und deren Verwendung |
| DE1966S0104339 Granted DE1620854B2 (de) | 1965-06-18 | 1966-06-18 | Verfahren zur herstellung von haertbaren mischungen aus bitumen und urethan- bzw. urethanharnstoffpolymeren |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1694887A Expired DE1694887C3 (de) | 1965-06-18 | 1966-06-18 | Polymerenverschnitte, bestehend aus Kohlenwasserstoffkautschuk und Polyurethan und deren Verwendung |
| DE1966S0104339 Granted DE1620854B2 (de) | 1965-06-18 | 1966-06-18 | Verfahren zur herstellung von haertbaren mischungen aus bitumen und urethan- bzw. urethanharnstoffpolymeren |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3175997A (en) * | 1959-10-23 | 1965-03-30 | Phillips Petroleum Co | Method of preparing polymers containing hydroxy end groups |
| US3338861A (en) * | 1964-03-30 | 1967-08-29 | Goodyear Tire & Rubber | Polyurethanes based on hydroxylterminated polydienes |
-
1966
- 1966-05-12 NL NL6606553A patent/NL6606553A/xx unknown
- 1966-06-17 GB GB27109/66A patent/GB1146645A/en not_active Expired
- 1966-06-17 GB GB27108/66A patent/GB1150429A/en not_active Expired
- 1966-06-18 DE DE19661645358 patent/DE1645358A1/de not_active Withdrawn
- 1966-06-18 JP JP41039395A patent/JPS5220518B1/ja active Pending
- 1966-06-18 DE DE1694887A patent/DE1694887C3/de not_active Expired
- 1966-06-18 DE DE1966S0104339 patent/DE1620854B2/de active Granted
- 1966-06-20 BE BE682834D patent/BE682834A/xx not_active IP Right Cessation
- 1966-06-20 BE BE682835D patent/BE682835A/xx not_active IP Right Cessation
- 1966-06-20 GB GB27446/66A patent/GB1145338A/en not_active Expired
- 1966-06-20 NL NL6608552A patent/NL6608552A/xx unknown
- 1966-06-20 BE BE682836D patent/BE682836A/xx unknown
- 1966-06-20 NL NL666608553A patent/NL150140B/xx not_active IP Right Cessation
-
1968
- 1968-03-15 US US713543A patent/US3427366A/en not_active Expired - Lifetime
-
1969
- 1969-01-23 US US797347*A patent/US3637558A/en not_active Expired - Lifetime
-
1971
- 1971-01-22 US US00109059A patent/US3714110A/en not_active Expired - Lifetime
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2018059931A1 (de) * | 2016-09-30 | 2018-04-05 | Tesa Se | Thermisch vulkanisierbarer klebstoff und daraus hergestelltes klebeband |
| US11208581B2 (en) | 2016-09-30 | 2021-12-28 | Tesa Se | Thermally vulcanisable adhesive and adhesive strip produced therefrom |
| EP3539997A1 (de) * | 2018-03-14 | 2019-09-18 | tesa SE | Thermisch vulkanisierbares, während der aufheiz- und härtungsphase scherfestes klebeband |
| US11111423B2 (en) | 2018-03-14 | 2021-09-07 | Tesa Se | Thermally vulcanizable adhesive tape with shear strength during the heating and curing phase |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1694887B2 (de) | 1978-11-09 |
| NL150140B (nl) | 1976-07-15 |
| DE1694887C3 (de) | 1979-07-12 |
| BE682836A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1966-12-20 |
| NL6608553A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1966-12-19 |
| GB1145338A (en) | 1969-03-12 |
| US3714110A (en) | 1973-01-30 |
| BE682835A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1966-12-20 |
| DE1694887A1 (de) | 1971-10-21 |
| GB1150429A (en) | 1969-04-30 |
| GB1146645A (en) | 1969-03-26 |
| BE682834A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1966-12-20 |
| JPS5220518B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-06-03 |
| NL6608552A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1966-12-19 |
| DE1620854A1 (de) | 1970-02-26 |
| US3427366A (en) | 1969-02-11 |
| US3637558A (en) | 1972-01-25 |
| DE1620854B2 (de) | 1976-08-26 |
| NL6606553A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1967-11-13 |
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