EP4373678A1 - Composé, mélange de caoutchouc contenant le composé, pneu de véhicule comportant au moins un élément comprenant le mélange de caoutchouc, procédé de préparation du composé, et utilisation du composé en tant qu'agent de protection contre le vieillissement et/ou antiozonant et/ou colorant - Google Patents
Composé, mélange de caoutchouc contenant le composé, pneu de véhicule comportant au moins un élément comprenant le mélange de caoutchouc, procédé de préparation du composé, et utilisation du composé en tant qu'agent de protection contre le vieillissement et/ou antiozonant et/ou colorantInfo
- Publication number
- EP4373678A1 EP4373678A1 EP22740285.6A EP22740285A EP4373678A1 EP 4373678 A1 EP4373678 A1 EP 4373678A1 EP 22740285 A EP22740285 A EP 22740285A EP 4373678 A1 EP4373678 A1 EP 4373678A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- radicals
- residues
- rubber
- compound
- compound according
- 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.)
- Pending
Links
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- 239000005060 rubber Substances 0.000 title claims abstract description 116
- 239000000203 mixture Substances 0.000 title claims abstract description 96
- 150000001875 compounds Chemical class 0.000 title claims abstract description 87
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 10
- 230000032683 aging Effects 0.000 title abstract description 10
- 239000011814 protection agent Substances 0.000 title abstract description 3
- 239000003086 colorant Substances 0.000 title abstract 2
- 125000003118 aryl group Chemical group 0.000 claims abstract description 24
- 125000001424 substituent group Chemical group 0.000 claims abstract description 20
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 16
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 11
- -1 aromatic radical Chemical class 0.000 claims description 102
- 150000003254 radicals Chemical class 0.000 claims description 39
- 239000003795 chemical substances by application Substances 0.000 claims description 27
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- 239000005062 Polybutadiene Substances 0.000 claims description 22
- 150000002367 halogens Chemical group 0.000 claims description 22
- 150000002576 ketones Chemical group 0.000 claims description 22
- 229920001194 natural rubber Polymers 0.000 claims description 21
- 229920003048 styrene butadiene rubber Polymers 0.000 claims description 19
- 230000003712 anti-aging effect Effects 0.000 claims description 18
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 239000011737 fluorine Substances 0.000 claims description 12
- 229910052731 fluorine Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 229920000642 polymer Polymers 0.000 claims description 12
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 11
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 11
- 150000005840 aryl radicals Chemical class 0.000 claims description 11
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 11
- 229910052794 bromium Inorganic materials 0.000 claims description 11
- 239000000460 chlorine Substances 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 125000004122 cyclic group Chemical group 0.000 claims description 9
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- 150000002148 esters Chemical group 0.000 claims description 9
- 125000001033 ether group Chemical group 0.000 claims description 9
- 238000005984 hydrogenation reaction Methods 0.000 claims description 9
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- 238000000576 coating method Methods 0.000 claims description 2
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- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 5
- 239000002966 varnish Substances 0.000 claims 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 32
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- 235000019241 carbon black Nutrition 0.000 description 21
- 239000000945 filler Substances 0.000 description 19
- 239000000377 silicon dioxide Substances 0.000 description 15
- 244000043261 Hevea brasiliensis Species 0.000 description 13
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 13
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- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 7
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- 239000006087 Silane Coupling Agent Substances 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- 150000004989 p-phenylenediamines Chemical class 0.000 description 6
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 6
- 239000011787 zinc oxide Substances 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- OUBMGJOQLXMSNT-UHFFFAOYSA-N N-isopropyl-N'-phenyl-p-phenylenediamine Chemical compound C1=CC(NC(C)C)=CC=C1NC1=CC=CC=C1 OUBMGJOQLXMSNT-UHFFFAOYSA-N 0.000 description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- 229920003211 cis-1,4-polyisoprene Polymers 0.000 description 5
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 5
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 4
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 4
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 4
- UTGQNNCQYDRXCH-UHFFFAOYSA-N N,N'-diphenyl-1,4-phenylenediamine Chemical compound C=1C=C(NC=2C=CC=CC=2)C=CC=1NC1=CC=CC=C1 UTGQNNCQYDRXCH-UHFFFAOYSA-N 0.000 description 4
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 4
- 238000005299 abrasion Methods 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 238000007306 functionalization reaction Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 4
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 4
- 150000002475 indoles Chemical class 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
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- 239000000047 product Substances 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 239000011593 sulfur Substances 0.000 description 4
- RRUHMDSGRHUALW-UHFFFAOYSA-N 1-n-phenyl-4-n-(1-phenylethyl)benzene-1,4-diamine Chemical compound C=1C=CC=CC=1C(C)NC(C=C1)=CC=C1NC1=CC=CC=C1 RRUHMDSGRHUALW-UHFFFAOYSA-N 0.000 description 3
- ZZMVLMVFYMGSMY-UHFFFAOYSA-N 4-n-(4-methylpentan-2-yl)-1-n-phenylbenzene-1,4-diamine Chemical compound C1=CC(NC(C)CC(C)C)=CC=C1NC1=CC=CC=C1 ZZMVLMVFYMGSMY-UHFFFAOYSA-N 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 239000012190 activator Substances 0.000 description 3
- 229940054051 antipsychotic indole derivative Drugs 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 239000002041 carbon nanotube Substances 0.000 description 3
- 150000004678 hydrides Chemical class 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 230000006698 induction Effects 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
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- 239000000344 soap Substances 0.000 description 3
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- OWRCNXZUPFZXOS-UHFFFAOYSA-N 1,3-diphenylguanidine Chemical compound C=1C=CC=CC=1NC(=N)NC1=CC=CC=C1 OWRCNXZUPFZXOS-UHFFFAOYSA-N 0.000 description 2
- PIBIAJQNHWMGTD-UHFFFAOYSA-N 1-n,3-n-bis(4-methylphenyl)benzene-1,3-diamine Chemical compound C1=CC(C)=CC=C1NC1=CC=CC(NC=2C=CC(C)=CC=2)=C1 PIBIAJQNHWMGTD-UHFFFAOYSA-N 0.000 description 2
- HPGLJHGYYVLNTR-UHFFFAOYSA-N 4-n-(2-methylphenyl)-1-n-(4-methylphenyl)benzene-1,4-diamine Chemical compound C1=CC(C)=CC=C1NC(C=C1)=CC=C1NC1=CC=CC=C1C HPGLJHGYYVLNTR-UHFFFAOYSA-N 0.000 description 2
- UHJVLUYSDYOULM-UHFFFAOYSA-N 4-n-(5-methylhexan-2-yl)-1-n-phenylbenzene-1,4-diamine Chemical compound C1=CC(NC(C)CCC(C)C)=CC=C1NC1=CC=CC=C1 UHJVLUYSDYOULM-UHFFFAOYSA-N 0.000 description 2
- 229920000049 Carbon (fiber) Polymers 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- 229920002943 EPDM rubber Polymers 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 2
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- 241000341871 Taraxacum kok-saghyz Species 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
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- 125000003545 alkoxy group Chemical group 0.000 description 2
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 238000000113 differential scanning calorimetry Methods 0.000 description 2
- 125000005044 dihydroquinolinyl group Chemical group N1(CC=CC2=CC=CC=C12)* 0.000 description 2
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 2
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- DEQZTKGFXNUBJL-UHFFFAOYSA-N n-(1,3-benzothiazol-2-ylsulfanyl)cyclohexanamine Chemical compound C1CCCCC1NSC1=NC2=CC=CC=C2S1 DEQZTKGFXNUBJL-UHFFFAOYSA-N 0.000 description 2
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- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- LOVYCUYJRWLTSU-UHFFFAOYSA-N 2-(3,4-dichlorophenoxy)-n,n-diethylethanamine Chemical compound CCN(CC)CCOC1=CC=C(Cl)C(Cl)=C1 LOVYCUYJRWLTSU-UHFFFAOYSA-N 0.000 description 1
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- DCQBZYNUSLHVJC-UHFFFAOYSA-N 3-triethoxysilylpropane-1-thiol Chemical compound CCO[Si](OCC)(OCC)CCCS DCQBZYNUSLHVJC-UHFFFAOYSA-N 0.000 description 1
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- 238000009411 base construction Methods 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- VLLYOYVKQDKAHN-UHFFFAOYSA-N buta-1,3-diene;2-methylbuta-1,3-diene Chemical compound C=CC=C.CC(=C)C=C VLLYOYVKQDKAHN-UHFFFAOYSA-N 0.000 description 1
- RTACIUYXLGWTAE-UHFFFAOYSA-N buta-1,3-diene;2-methylbuta-1,3-diene;styrene Chemical compound C=CC=C.CC(=C)C=C.C=CC1=CC=CC=C1 RTACIUYXLGWTAE-UHFFFAOYSA-N 0.000 description 1
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical class C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- 125000003636 chemical group Chemical group 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical compound [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 150000001925 cycloalkenes Chemical class 0.000 description 1
- 125000000000 cycloalkoxy group Chemical group 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920005558 epichlorohydrin rubber Polymers 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- QQBWQAURZPGDOG-UHFFFAOYSA-N ethyl hexanoate;zinc Chemical compound [Zn].CCCCCC(=O)OCC QQBWQAURZPGDOG-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229910021389 graphene Inorganic materials 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 239000000383 hazardous chemical Substances 0.000 description 1
- 231100000206 health hazard Toxicity 0.000 description 1
- 229920006270 hydrocarbon resin Polymers 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 238000010077 mastication Methods 0.000 description 1
- 230000018984 mastication Effects 0.000 description 1
- 231100000647 material safety data sheet Toxicity 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 150000001282 organosilanes Chemical class 0.000 description 1
- 230000036542 oxidative stress Effects 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical group N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000636 poly(norbornene) polymer Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 230000001698 pyrogenic effect Effects 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- JPPLPDOXWBVPCW-UHFFFAOYSA-N s-(3-triethoxysilylpropyl) octanethioate Chemical compound CCCCCCCC(=O)SCCC[Si](OCC)(OCC)OCC JPPLPDOXWBVPCW-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 125000005372 silanol group Chemical group 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000004945 silicone rubber Substances 0.000 description 1
- 125000005373 siloxane group Chemical group [SiH2](O*)* 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000012721 stereospecific polymerization Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- TXDNPSYEJHXKMK-UHFFFAOYSA-N sulfanylsilane Chemical class S[SiH3] TXDNPSYEJHXKMK-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- VTHOKNTVYKTUPI-UHFFFAOYSA-N triethoxy-[3-(3-triethoxysilylpropyltetrasulfanyl)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCSSSSCCC[Si](OCC)(OCC)OCC VTHOKNTVYKTUPI-UHFFFAOYSA-N 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B60—VEHICLES IN GENERAL
- B60C—VEHICLE TYRES; TYRE INFLATION; TYRE CHANGING; CONNECTING VALVES TO INFLATABLE ELASTIC BODIES IN GENERAL; DEVICES OR ARRANGEMENTS RELATED TO TYRES
- B60C1/00—Tyres characterised by the chemical composition or the physical arrangement or mixture of the composition
- B60C1/0016—Compositions of the tread
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B60—VEHICLES IN GENERAL
- B60C—VEHICLE TYRES; TYRE INFLATION; TYRE CHANGING; CONNECTING VALVES TO INFLATABLE ELASTIC BODIES IN GENERAL; DEVICES OR ARRANGEMENTS RELATED TO TYRES
- B60C1/00—Tyres characterised by the chemical composition or the physical arrangement or mixture of the composition
- B60C1/0025—Compositions of the sidewalls
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/02—Elements
- C08K3/04—Carbon
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3415—Five-membered rings
- C08K5/3417—Five-membered rings condensed with carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L7/00—Compositions of natural rubber
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L9/00—Compositions of homopolymers or copolymers of conjugated diene hydrocarbons
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F1/00—General methods for the manufacture of artificial filaments or the like
- D01F1/02—Addition of substances to the spinning solution or to the melt
- D01F1/06—Dyes
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H21/00—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties
- D21H21/14—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties characterised by function or properties in or on the paper
- D21H21/28—Colorants ; Pigments or opacifying agents
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B60—VEHICLES IN GENERAL
- B60C—VEHICLE TYRES; TYRE INFLATION; TYRE CHANGING; CONNECTING VALVES TO INFLATABLE ELASTIC BODIES IN GENERAL; DEVICES OR ARRANGEMENTS RELATED TO TYRES
- B60C1/00—Tyres characterised by the chemical composition or the physical arrangement or mixture of the composition
- B60C2001/005—Compositions of the bead portions, e.g. clinch or chafer rubber or cushion rubber
Definitions
- Vehicle tire which has the rubber mixture in at least one component, method for producing the compound and use of the compound as anti-aging agent and/or anti-ozone agent and/or dye
- the invention relates to a compound, a rubber compound containing the compound, a vehicle tire which has the rubber compound in at least one component, a method for producing the compound and the use of the compound as an aging inhibitor and/or antiozonant and/or dye.
- Natural rubber, synthetic polymers such as IR, BR, SSBR, ESBR, etc.
- natural and synthetic oils, greases and lubricants are subject to oxidation reactions when stored for a long period of time and especially in the target application, which often takes place at higher temperatures, which can have adverse effects affect the original desired properties.
- the polymer chains are shortened to the point of liquefying the material, or the material is subsequently hardened.
- Anti-aging agents therefore make a significant contribution to the longevity of vehicle tires and other technical rubber items.
- antioxidants are aromatic amines, such as 6-PPD (N-(1,3-dimethylbutyl)-N'-phenyl-p-phenylenediamine),
- IPPD N-isopropyl-N'-phenyl-p-phenylenediamine
- SPPD N-(1-phenylethyl)-N'-phenyl-p-phenylenediamine
- Anti-aging agents that react with ozone in particular and intercept it are also referred to as “ozone protection agents” or “antiozonants”.
- the invention is based on the object of providing a novel compound which can be used in particular as an anti-aging agent in vehicle tires or other technical rubber articles with a lower risk potential and sufficient solubility in the respective matrix, for example and in particular in the polymer. This is intended to ensure continued optimal protection against oxygen and ozone while reducing the health hazards and to prevent the tendency to bloom.
- the object is achieved by the compound according to the invention as claimed in claim 1, the rubber mixture according to the invention containing the compound and the vehicle tire according to the invention which has the rubber mixture according to the invention in at least one component.
- the object is achieved through the use of the compound as an anti-aging agent and/or an anti-ozone agent.
- the compound according to claim 1 can further be used as a dye. Furthermore, the object is achieved by the process according to the invention for preparing the compound according to the invention.
- the compound according to claim 1 has the general formula I): I) wherein A is an aromatic radical optionally bearing additional substituents; and wherein R 1 is selected from the group consisting of xi) aromatic residues, the aromatic residues optionally having substituents selected from the group consisting of halogen residues, cyano residues, ester residues, ketone residues, ether residues and thioether radicals, and xii) linear, branched and cyclic aliphatic Ci to Ci2 radicals, and xiii) combinations of aromatic and aliphatic Ci to C12 radicals; and wherein R 3 is selected from the group consisting of linear, branched and cyclic, saturated and unsaturated, aliphatic C 1 to C 12 radicals optionally bearing one or more halogen substituents, aryl radicals optionally bearing one or more carry halogen substituents, and halogen radicals, with fluorine, bromine and chlorine being preferred, cyano radicals, ester radicals,
- A is an aromatic radical which optionally bears additional substituents; and wherein R 1 is selected from the group consisting of benzyl and C 1 to C 12 linear, branched and cyclic aliphatic radicals; and wherein R 3 is selected from the group consisting of linear, branched and cyclic aliphatic C 1 to C-12 radicals, as well as aryl radicals, cyano radicals, halogen radicals, with fluorine, bromine and chlorine being preferred, ether radicals and thioether radicals, and where n is 0 or 1 or 2 or 3 or 4, where the radicals R 3 when n is 2 or 3 or 4 are independently the same or different. It is clear to the person skilled in the art that when n is 0 or 1 or 2 or 3 all other free positions on the benzene ring of the indole skeleton are hydrogen atoms.
- Ci is also used to designate the position of the most oxidized carbon atom or the highest priority according to the Cahn-Ingold-Prelog Convention (CIP). It is clear to the person skilled in the art in the respective context what is meant.
- the compound according to the invention is an indole derivative and has a lower risk potential than known anti-aging agents based on aniline (possible cleavage product of 6-PPD). If one compares the safety data sheets for the base substances aniline and indole, it is striking that, unlike aniline, indole is neither mutagenic nor mutagenic. This is a decisive advantage, especially in a technical application such as in vehicle tires or other rubber products, since the rubber ingredients can be released through abrasion or other degradation processes. In addition, the oxidation products of 6-PPD pose a particular risk to coho salmon. It can therefore be assumed that this applies to aquatic life in general (Tian et al, Science, 2020 Z. Tian, Science, 2021, 371 (6525), 185-189).
- indole derivatives are proposed in pharmaceutical compositions or compositions for skin care, as disclosed in US 20200339581 A1 and JP 2004196699A.
- JP06147585B2 discloses indole derivatives of the formula S1) where R 1 and R 2 are defined differently in JP06147585B2 than here.
- the compound according to the invention has the advantage that it does not have any vulcanizable groups (such as --SH) which allow attachment to rubber or polymers.
- the molecules By being attached, the molecules would be bound locally and thus could not act at a remote site where oxidative stress occurs. The molecules would therefore not develop their full protection as anti-aging agents and/or anti-ozone agents as a result of binding.
- the invention also includes configurations that result from the combination of different features of different gradations when these features are preferred, so that a combination of a first feature referred to as “preferred” or a feature described in the context of an advantageous embodiment with a further feature, e.g. B. "particularly preferred” designated feature is covered by the invention.
- A is preferably selected from the group consisting of phenylene, naphthylene and antracenylene radicals and phenylene, naphthylene and antracenylene radicals having one or more substituents, the substituents preferably being selected from the group consisting of linear, branched and cyclic ones aliphatic Ci to Ci2 radicals, and aryl radicals, cyano radicals, halogen radicals, with fluorine, bromine and chlorine being preferred, ether radicals and thioether radicals.
- A is particularly preferably a phenylene radical and thus a phenyl radical having two or more attached substituents. This results in a particularly advantageous solubility of these compounds according to the invention in rubber mixtures, in particular for vehicle tires and other technical rubber articles.
- the indole radical and the group NHR 1 on the benzene ring (of the phenylene radical) are preferably arranged in the para position to one another.
- the compound according to the invention preferably has the structure according to formula II): wherein R 1 is selected from the group consisting of xi) aromatic residues, the aromatic residues optionally having substituents selected from the group consisting of halogen residues, cyano residues, ester residues, ketone residues, ether residues and thioether radicals, and xii) linear, branched and cyclic aliphatic Ci to Ci2 radicals, and xiii) combinations of aromatic and aliphatic Ci to C12 radicals; and wherein R 2 is selected from the group consisting of linear, branched and cyclic, saturated and unsaturated, aliphatic C 1 to C 12 radicals optionally bearing one or more halogen substituents, aryl radicals optionally bearing one or more carry halogen substituents, and halogen radicals, with fluorine, bromine and chlorine being preferred, cyano radicals, ester radicals, ketone radicals, ether radicals and thioether
- n is 0 or 1 or 2 or 4
- the free positions on the benzene ring are hydrogen atoms.
- n is preferably equal to 0, which applies to formula I) and II).
- the radical R 1 is selected from the group consisting of xi) aromatic radicals, where the aromatic radicals optionally have substituents selected from the group consisting of halogen radicals, cyano radicals,
- the aromatic radical from subgroup xi) is, for example and preferably, a phenyl radical.
- the aromatic radicals of subgroup xi) can carry substituents. As stated above, these are selected from the group consisting of halogen radicals, cyano radicals, ester radicals, ketone radicals, ether radicals and thioether radicals.
- the substituents are preferably selected from the group consisting of ester residues, ketone residues, ether residues and thioether residues.
- the aromatic radical is not substituted on the two C atoms which are adjacent to the Ci atom, ie the carbon atom which is bonded to the N atom.
- the aromatic radical is not substituted on the two C atoms which are adjacent to the Ci atom, ie the carbon atom which is bonded to the N atom.
- the aromatic radical of subgroup xi) is unsubstituted.
- R 1 is bonded to the nitrogen atom (N) through a tertiary carbon atom.
- the Ci atom is therefore preferably a tertiary carbon atom.
- tertiary carbon atom means a carbon atom which is bonded to only one hydrogen atom.
- the mixed aromatic and aliphatic radical from subgroup xiii) is, for example and preferably, selected from the group consisting of benzyl and 1-phenylalkyl radicals having a total of 7 to 18 carbon atoms, in particular selected from benzyl and 1-phenylethyl radicals, where 1 -Phenylalkyl radicals, in particular 1-phenylethyl, are particularly preferred because of the tertiary carbon atom.
- R 1 is particularly preferably a branched alkyl radical having 3 to 12 carbon atoms, again preferably 3 to 8 carbon atoms.
- at least one branch is preferably present on the Ci atom, ie on the on the nitrogen atom (N) bonded carbon atom, making the Ci atom a tertiary carbon atom.
- R 1 is very particularly preferably selected from 1,3-dimethylbutyl and cyclohexyl radicals, and R 1 is again very particularly preferably a 1,3-dimethylbutyl radical.
- the radical or radicals R 2 are independently identical or different and are selected from the group consisting of linear, branched and cyclic, saturated and unsaturated, aliphatic Ci - to Ci2 radicals, which optionally carry one or more halogen substituents, Aryl radicals optionally bearing one or more halogen substituents, and halogen radicals, with fluorine, bromine and chlorine being preferred, cyano radicals, ester radicals, ketone radicals, ether radicals and thioether radicals.
- R 2 radicals mentioned can already be attached to the respective benzene ring or its precursor, in particular by selecting suitable starting substances.
- n in formula II is preferably 0 (zero).
- the indole radical and the group NHR 1 on the benzene ring (of the phenylene radical) are preferably arranged in the para position to one another.
- the compound has the structure according to formula III):
- the compound according to the invention according to formula I) or formula II) and formula III) or all of the above statements is particularly useful as an anti-aging agent and/or anti-ozone agent in vehicle tires and/or technical rubber articles, such as in particular an air spring, a bellows, conveyor belt, belt, belt , hoses, rubber bands, profiles, a seal, a membrane, tactile sensors for medical applications or robotic applications, or a shoe sole or parts thereof, and/or oils and/or lubricants.
- a further object of the present invention is therefore the use of the compound according to the invention as an anti-aging agent and/or an anti-ozone agent in vehicle tires and/or technical rubber articles, such as in particular an air spring, a bellows, a conveyor belt, a belt, a belt, a hose, a rubber band, a profile, a seal, a membrane, tactile sensors for medical applications or robotic applications, or a shoe sole or parts thereof, and/or oils and/or lubricants.
- an air spring, a bellows, a conveyor belt, a belt, a belt, a hose, a rubber band, a profile, a seal, a membrane, tactile sensors for medical applications or robotic applications, or a shoe sole or parts thereof, and/or oils and/or lubricants such as in particular an air spring, a bellows, a conveyor belt, a belt, a belt, a hose, a rubber band, a profile, a seal, a membrane, tactile sensors for medical applications or robotic
- Another object of the invention is the use of the compound according to the invention of formula I) or formula II) and formula III) or all of the above statements as a dye in fibers and/or polymers and/or paper and/or in (coating) inks and paints.
- Another aspect of the present invention is a process for preparing the compound of the formula I), which comprises the following process steps: a) Provision of the compound according to formula A)
- n is preferably equal to zero.
- hydrogenation reagent a compound that enables hydrogenation.
- hydrides in particular metal hydrides.
- a suitable hydride is e.g. B. sodium borohydride.
- hydrogen is not additionally listed under “hydrogenation reagent” since it is explicitly mentioned as an alternative. Of course, all reagents that generate hydrogen in situ, which causes the hydrogenation, are still included under “hydrogenation reagent”.
- the reaction in step b) preferably takes place with hydrogen (H2) and the ketone or aldehyde, preferably ketone, using a hydrogenation catalyst and preferably at a temperature of 50 to 70° C., in particular 60° C., for example.
- Hydrogen is preferably injected at a pressure of 15 to 25 bar, in particular 20 bar, for example, and stirring is then preferably carried out for 1 to 20 hours, preferably 8 to 13 hours, in particular 10 hours, for example.
- the ketone in step b) is the ketone derivative of the later radical R 1 ; With an aldehyde corresponding to the aldehyde derivative.
- the ketone methyl isobutyl ketone is preferably used here.
- a suitable catalyst referred to as “hydrogenation catalyst” in the context of the present invention, is preferably used in the process steps in which a reaction with hydrogen takes place.
- the hydrogenation catalyst of the process is preferably a noble metal catalyst, such as in particular palladium (Pd) or platinum (Pt).
- the noble metal on carbon (C) is preferably used, such as palladium on carbon (Pd/C).
- the reaction with hydrogen in step b) preferably takes place in a container suitable for the comparatively high pressures, such as in particular an autoclave or another pressure reactor.
- A is preferably a phenylene radical and m is zero.
- the linkages on the benzene ring (of the phenylene radical) are preferably arranged in the para position to one another.
- a further object of the invention is a rubber mixture.
- the rubber mixture according to the invention contains the compound of the formula I), in particular of the formula II), in particular of the formula III).
- the rubber mixture according to the invention can be any rubber mixture, in particular in which the novel compound according to the invention of the formula I), in particular of the formula II), in particular according to formula III), acts as an anti-aging agent and/or an anti-ozone agent with lower toxicity.
- the rubber mixture according to the invention contains at least one rubber.
- the rubber mixture according to the invention preferably contains 0.1 to 10 phr, particularly preferably 0.1 to 7 phr, very particularly preferably 1 to 6 phr, of the compound of the formula I), in particular of the formula II), in particular of the formula III).
- the specification phr (parts per hundred parts of rubber by weight) used in this document is the quantity specification for compound formulations customary in the rubber industry.
- the dosage of the parts by weight of the individual substances is based on 100 parts by weight of the total mass of all high molecular weight (Mw greater than 20,000 g/mol) rubbers present in the mixture.
- the rubber mixture according to the invention contains at least one diene rubber.
- the rubber mixture can thus contain a diene rubber or a mixture of two or more different diene rubbers.
- the diene rubber is preferably selected from the group consisting of natural polyisoprene (NR), synthetic polyisoprene (IR), epoxidized polyisoprene (ENR), butadiene rubber (BR), butadiene-isoprene rubber, solution-polymerized styrene-butadiene rubber (SSBR ), emulsion-polymerized styrene-butadiene rubber (ESBR), styrene-isoprene rubber, liquid rubbers with a molecular weight Mw greater than 20000 g/mol, flalobutyl rubber, polynorbornene, isoprene isobutylene copolymer, ethylene propylene diene rubber,
- nitrile rubber chloroprene rubber, acrylate rubber, fluorine rubber, silicone rubber, polysulfide rubber, epichlorohydrin rubber, styrene-isoprene-butadiene terpolymer, hydrogenated acrylonitrile-butadiene rubber and hydrogenated styrene-butadiene rubber.
- nitrile rubber hydrogenated acrylonitrile butadiene rubber, chloroprene rubber, butyl rubber, halobutyl rubber and/or ethylene-propylene-diene rubber are used in the production of technical rubber articles, such as belts, belts and hoses, and/or shoe soles.
- the mixture compositions known to those skilled in the art for these rubbers, which are particular with regard to fillers, plasticizers, vulcanization systems and additives, are preferably used.
- the natural and/or synthetic polyisoprene of all embodiments can be either cis-1,4-polyisoprene or 3,4-polyisoprene. However, preference is given to using cis-1,4-polyisoprenes with a cis-1,4 content>90% by weight. On the one hand, such a polyisoprene can be obtained by stereospecific polymerization in solution with Ziegler-Natta catalysts or using finely divided lithium alkyls. On the other hand, natural rubber (NR) is a cis-1,4-polyisoprene in which the cis-1,4 content in the natural rubber is greater than 99% by weight.
- a mixture of one or more natural polyisoprenes with one or more synthetic polyisoprene(s) is also conceivable.
- the term "natural rubber” means naturally occurring rubber that can be obtained from Hevea rubber trees and "non-Hevea” sources.
- Non-Hevea sources include guayule shrubs and dandelions such as TKS (Taraxacum kok-saghyz; Russian dandelion).
- TKS Teraxacum kok-saghyz; Russian dandelion.
- BR polybutadiene
- BR polybutadiene
- it can be of any type known to the person skilled in the art. These include the so-called high-cis and low-cis types, polybutadiene with a cis content greater than or equal to 90% by weight being the high-cis type and polybutadiene with a cis content of less than 90% by weight.
- a low-cis polybutadiene is, for example, Li-BR (lithium-catalyzed butadiene rubber) with a cis content of 20 to 50% by weight. Particularly good properties and low flysteresis of the rubber compound are achieved with a high-cis BR.
- Li-BR lithium-catalyzed butadiene rubber
- the polybutadiene(s) used can/can be end-group-modified with modifications and functionalizations and/or functionalized along the polymer chains.
- the modification can involve those with hydroxyl groups and/or ethoxy groups and/or epoxy groups and/or siloxane groups and/or amino groups and/or aminosiloxane and/or carboxy groups and/or Act phthalocyanine groups and / or silane sulfide groups.
- modifications known to those skilled in the art, also referred to as functionalizations are also possible.
- Metal atoms can be part of such functionalizations.
- styrene-butadiene rubber styrene-butadiene copolymer
- SSBR solution-polymerized styrene-butadiene rubber
- ESBR emulsion-polymerized styrene-butadiene rubber
- the styrene-butadiene copolymer used can be end-group-modified with the modifications and functionalizations mentioned above for polybutadiene and/or functionalized along the polymer chains.
- the at least one diene rubber is preferably selected from the group consisting of natural polyisoprene (NR, natural rubber), synthetic polyisoprene (IR), butadiene rubber (BR), solution polymerized styrene butadiene rubber (SSBR), emulsion polymerized styrene butadiene rubber (ESBR), butyl rubber (IIR), and halobutyl rubber.
- the at least one diene rubber is selected from the group consisting of natural polyisoprene (NR), synthetic polyisoprene (IR),
- BR butadiene rubber
- SSBR solution polymerized styrene butadiene rubber
- ESBR emulsion polymerized styrene butadiene rubber
- the rubber mixture contains at least one natural polyisoprene (NR) and/or synthetic polyisoprene (IR), preferably in amounts of 50 to 100 phr, and according to a particularly advantageous embodiment of the invention 80 to 100 phr, entirely more preferably 95 to 100 phr, again preferably 100 phr.
- NR natural polyisoprene
- IR synthetic polyisoprene
- the rubber mixture contains less than 100 phr NR and/or IR, it preferably contains at least one diene rubber selected from the group consisting of butadiene rubber (BR), solution-polymerized styrene-butadiene rubber (SSBR) and emulsion polymerized styrene butadiene rubber (ESBR).
- BR butadiene rubber
- SSBR solution-polymerized styrene-butadiene rubber
- ESBR emulsion polymerized styrene butadiene rubber
- the rubber mixture contains at least one natural polyisoprene (NR), preferably in amounts of 5 to 55 phr, and according to a particularly advantageous embodiment of the invention 5 to 25 phr, very particularly preferably 5 to 20 phr.
- NR natural polyisoprene
- a rubber mixture of this type shows, in particular, good processability and reversion stability, as well as optimized tear properties and optimum rolling resistance behavior.
- the rubber mixture contains at least one polybutadiene (BR, butadiene rubber), preferably in amounts of 10 to 80 phr, particularly preferably 10 to 50 phr, and according to a particularly advantageous embodiment of the invention 15 to 40 phr. This achieves particularly good tear and abrasion properties for the rubber mixture according to the invention and optimum braking performance.
- the rubber mixture contains at least one solution-polymerized styrene-butadiene rubber (SSBR), preferably in amounts of 10 to 80 phr, particularly preferably 30 to 80 phr, and according to a particularly advantageous embodiment of the invention 50 to 70 phr.
- SSBR solution-polymerized styrene-butadiene rubber
- SSBR is used in combination with at least one other rubber in order to achieve an optimal and balanced property profile.
- the rubber mixture preferably contains at least one filler, preferably in amounts of 30 to 500 phr, particularly preferably 50 to 400 phr, again preferably 80 to 300 phr.
- the filler is a reinforcing filler, preferably selected from the group consisting of carbon blacks and silica.
- Suitable carbon blacks are all types of carbon black known to those skilled in the art.
- the carbon black is preferably selected from carbon blacks and pyrolysis carbon blacks, carbon blacks being more preferred.
- the carbon black preferably has an iodine number, according to ASTM D 1510, which is also referred to as the iodine adsorption number, between 30 and 250 g/kg, preferably 30 to 180 g/kg, particularly preferably 40 to 180 g/kg, and very particularly preferably 40 to 130 g/kg, and a DBP number according to ASTM D 2414 of 30 to 200 ml/100 g, preferably 70 to 200 ml/100 g, particularly preferably 90 to 200 ml/100 g.
- ASTM D 1510 which is also referred to as the iodine adsorption number
- the DBP number according to ASTM D 2414 determines the specific absorption volume of a carbon black or a light-colored filler using dibutyl phthalate.
- Particularly suitable and preferred is a carbon black with an iodine adsorption number of between 80 and 110 g/kg and a DBP number of 100 to 130 ml/100 g, such as in particular carbon black of the N339 type.
- the silica is preferably amorphous silica, for example precipitated silicic acid, also referred to as precipitated silica.
- precipitated silica also referred to as precipitated silica.
- pyrogenic silicon dioxide can also be used.
- a finely divided, precipitated silica which has a nitrogen surface area (BET surface area) (according to DIN ISO 9277 and DIN 66132) from 35 to 400 m 2 /g, preferably from 35 to 350 m 2 / g, more preferably from 85 to 320 m 2 / g and most preferably from 120 to 235 m 2 / g, and a CTAB surface area (according to ASTM D 3765) from 30 to 400 m 2 / g, preferably from 30 to 330 m 2 /g, more preferably from 80 to 300 m 2 /g and most preferably from 115 to 200 m 2 /g.
- BET surface area nitrogen surface area
- CTAB surface area accordinging to ASTM D 3765
- silicas z. B both those of the type Ultrasil® VN3 (Flanderlsname) from Evonik and highly dispersible silicas, so-called FID silicas (e.g. Zeosil® 1165 MP from Solvay), can be used.
- FID silicas e.g. Zeosil® 1165 MP from Solvay
- the rubber mixture contains at least one silica as a filler, preferably in Amounts of 30 to 500 phr, more preferably 50 to 400 phr, again preferably 80 to 300 phr.
- silicic acid is present in particular as the sole or main filler (more than 50% by weight, based on the total amount of filler).
- the rubber mixture contains at least one silica as an additional filler, preferably in amounts of 5 to 100 phr, particularly preferably 5 to 80 phr, again preferably 10 to 60 phr.
- Silicic acid is contained in these amounts in particular as a further filler in addition to another main filler, such as in particular a carbon black.
- silicic acid and “silica” are used synonymously in the context of the present invention.
- the rubber mixture according to the invention contains from 0.1 to 60 phr, preferably from 3 to 40 phr, particularly preferably from 5 to 30 phr, very particularly preferably from 5 to 15 phr, of at least one carbon black.
- carbon black is contained in particular as a further filler in addition to a main filler, such as in particular silica.
- the rubber mixture according to the invention contains 30 to 300 phr, preferably 30 to 200 phr, particularly preferably 40 to 100 phr of at least one carbon black.
- carbon black is present as the only filler or as the main filler and optionally in combination with silica in the smaller amounts mentioned above.
- the rubber mixture contains 5 to 60 phr, particularly preferably 5 to 40 phr, of at least one carbon black and 50 to 300 phr, preferably 80 to 200 phr of at least one silica.
- the rubber mixture can also contain other fillers that have a reinforcing effect or do not have a reinforcing effect.
- the other (non-reinforcing) fillers include aluminosilicates, kaolin, chalk, starch, magnesium oxide, titanium dioxide or rubber gels and fibers (such as, for example, aramid fibers, glass fibers, carbon fibers, cellulose fibers).
- CNT carbon nanotubes
- FICF hollow carbon fibers
- modified CNT containing one or more functional groups such as flydroxy, carboxy and carbonyl groups
- zinc oxide does not belong to the fillers.
- the rubber mixture can contain customary additives in customary parts by weight, which are preferably added in at least one basic mixing stage during its production.
- additives include a) anti-aging agents known in the prior art, such as e.g. B. p-phenylenediamines, such as
- N-phenyl-N'-(1,3-dimethylbutyl)-p-phenylenediamine (6PPD), N,N'-diphenyl-p-phenylenediamine (DPPD),
- SPPD N-(1-phenylethyl)-N'-phenyl-p-phenylenediamine
- DTPD N,N'-ditolyl-p-phenylenediamine
- IPPD N-isopropyl-N'-phenyl-p-phenylenediamine
- TMQ 2,2,4-Trimethyl,2-dihydroquinoline
- activators such as e.g. B. zinc oxide and fatty acids (z. B.
- stearic acid and / or other activators such as zinc complexes such as zinc ethylhexanoate, c) activators and / or agents for the binding of fillers, in particular carbon black or silica, such as S - (3-aminopropyl ) thiosulfuric acid and/or its metal salts (connection to carbon black) and silane coupling agents (connection to silicon dioxide, in particular silicic acid), d) antiozonant waxes, e) resins, in particular adhesive resins, f) mastication aids, such as e.g. B.
- fillers in particular carbon black or silica, such as S - (3-aminopropyl ) thiosulfuric acid and/or its metal salts (connection to carbon black) and silane coupling agents (connection to silicon dioxide, in particular silicic acid), d) antiozonant waxes, e) resins, in particular adhesive resins, f) mastication aid
- plasticizers
- mineral oil this is preferably selected from the group consisting of DAE (Distillated Aromatic Extracts), RAE (Residual Aromatic Extract), TDAE (Treated Distillated Aromatic Extracts), MES (Mild Extracted Solvents) and naphthenic oils.
- the rubber mixture according to the invention does not contain any aging inhibitors from the group of p-phenylenediamines, in particular those from list a) above.
- the rubber mixture according to the invention contains from 0 to 0.1 phr, in particular 0 phr, of further aging inhibitors based on p-phenylenediamines, which are selected from the group containing, preferably consisting of, N-phenyl-N'- (1,3-dimethylbutyl)-p-phenylenediamine (6PPD),
- SPPD N-(1-phenylethyl)-N'-phenyl-p-phenylenediamine
- N,N'-diphenyl-p-phenylenediamine DPPD
- N,N'-ditolyl-p-phenylenediamine DTPD
- N-isopropyl-N'-phenyl-p-phenylenediamine IPPD
- At least one other of the p-phenylenediamine anti-aging agents mentioned is also present, so that the compound according to the invention only partially replaces the p-phenylenediamines known in the prior art. Flier also achieves the advantage of the invention, just not to the optimum extent.
- aging inhibitors based on dihydroquinoline such as TMQ
- TMQ dihydroquinoline
- the amount of dihydroquinolines present, such as TMQ in particular, is preferably from 0.1 to 3, in particular from 0.5 to 1.5 phr.
- Anti-ozone waxes (group d above) are considered separately and, according to preferred embodiments of the invention, are present in the rubber mixture, regardless of whether additional anti-aging agents a) are present.
- the silane coupling agents can be of any type known to those skilled in the art.
- the rubber mixture can thus contain a mixture of different silanes.
- silane coupling agents react with the surface silanol groups of the silicon dioxide, in particular the silicic acid, or other polar groups during the mixing of the rubber or the rubber mixture (in situ) or even before the filler is added to the rubber in the sense of a pretreatment (premodification).
- Coupling agents known from the prior art are bifunctional organosilanes which have at least one alkoxy, cycloalkoxy or phenoxy group as a leaving group on the silicon atom and which have a group as another functionality which, after cleavage, can undergo a chemical reaction with the double bonds of the polymer.
- the latter group can be z. Examples are the following chemical groups:
- Blocked mercaptosilanes as z. B. are known from WO 99/09036, can be used as a silane coupling agent.
- Silanes as described in WO 2008/083241 A1, WO 2008/083242 A1, WO 2008/083243 A1 and WO 2008/083244 A1, can also be used.
- the proportion of the total amount of further additives is preferably 3 to 150 phr, particularly preferably 3 to 100 phr and very particularly preferably 5 to 80 phr.
- Zinc oxide (ZnO) can be contained in the abovementioned amounts in the total proportion of the other additives.
- the conventionally used zinc oxide usually has a BET surface area of less than 10 m 2 /g. But it can a zinc oxide with a BET surface area of 10 to 100 m 2 /g, such as so-called “nano-zinc oxides”, can also be used.
- the rubber mixture according to the invention is preferably used in vulcanized form, in particular in vehicle tires or other vulcanized technical rubber articles.
- the vulcanization of the rubber mixture according to the invention is preferably carried out in the presence of sulfur and/or sulfur donors with the aid of vulcanization accelerators, it being possible for some vulcanization accelerators to also act as sulfur donors.
- the accelerator is selected from the group consisting of thiazole accelerators, mercapto accelerators, sulfenamide accelerators, thiocarbamate accelerators, thiuram accelerators, thiophosphate accelerators, thiourea accelerators, xanthogenate accelerators and guanidine accelerators.
- a sulfenamide accelerator selected from the group consisting of N-cyclohexyl-2-benzothiazole sulfenamide (CBS), N,N-dicyclohexylbenzothiazole-2-sulfenamide (DCBS),
- benzothiazyl-2-sulfenmorpholide MMS
- N-tert-butyl-2-benzothiazylsulfenamide TBBS
- guanidine accelerators such as diphenylguanidine (DPG).
- vulcanization retarders can be present in the rubber compound.
- the production of the rubber mixture is preferably otherwise carried out according to the process customary in the rubber industry, in which first, in one or more mixing stages, a basic mixture with all the components apart from the vulcanization system (e.g. sulfur and vulcanization-influencing substances) is produced.
- the finished mixture is produced by adding the vulcanization system in a final mixing stage.
- the finished mixture is further processed, e.g. by an extrusion process or calendering, and brought into the appropriate shape.
- the rubber mixture according to the invention is particularly suitable for use in vehicle tires, in particular pneumatic vehicle tires.
- vehicle tires in particular pneumatic vehicle tires.
- the use in all tire components is conceivable in principle, in particular in an outer component, in particular and preferably in the horn profile, tread strip and/or the sidewall tread strip.
- the rubber mixture according to the invention is preferably used at least in the cap.
- the mixture is brought into the appropriate form, preferably an outer component, as a ready-to-use mixture before vulcanization and applied in the known manner during the production of the vehicle tire blank.
- the rubber mixture according to the invention for use as other body mixture in vehicle tires is produced as already described.
- the difference lies in the shaping after the extrusion process or the calendering of the mixture.
- the forms of the still unvulcanized rubber mixture obtained in this way for one or more different body mixtures are then used to build up a green tire.
- the rubber mixtures for the inner components of a tire such as essentially squeegee, inner liner (inner layer), core profile, belt, shoulder, belt profile, carcass, bead reinforcement, bead profile, horn profile and bandage, are referred to as body mixture.
- the still unvulcanized green tire is then vulcanized.
- the extruded rubber mixture is still unvulcanized Mixture brought into the appropriate form and often provided with reinforcements, eg synthetic fibers or steel cords.
- reinforcements eg synthetic fibers or steel cords.
- a further subject of the present invention is a vehicle tire which has the rubber mixture according to the invention containing the compound according to the invention in at least one component.
- At least one component of the vulcanized vehicle tire has a vulcanizate of at least one rubber mixture according to the invention. It is known to those skilled in the art that most substances, e.g. B. the contained rubbers are present or can be present in a chemically modified form either after mixing or only after vulcanization.
- vehicle tires are understood to mean pneumatic vehicle tires and solid rubber tires, including tires for industrial and construction site vehicles, truck, passenger car and two-wheeler tires.
- the vehicle tire according to the invention preferably has the rubber mixture according to the invention in at least one outer component, the outer component preferably being a tread strip, a side wall and/or a horn profile.
- the vehicle tire according to the invention can have the rubber mixture according to the invention containing the compound according to the invention according to formula I), in particular according to formula II), in particular according to formula III), thus also in several components in a possibly adapted composition.
- the invention is to be explained in more detail below using exemplary embodiments.
- the compound according to formula III) was examined for its potential protective effect as an anti-aging agent by measuring the oxidation induction time under laboratory conditions.
- IR liquid synthetic polyisoprene
- LIR-50 LIR-50
- the sample was kept isothermally under an N2 atmosphere at 180°C for 5 minutes and then switched to an O2 atmosphere (with a flow rate of 50 mL/min).
- the oxidation was determined via a peak using DSC (differential scanning calorimetry).
- the compound according to formula III is an adequate substitute for the more harmful compound 6-PPD.
- the compound according to the invention according to formula I), for example according to formula III for example instead of the anti-aging agents known in the prior art, such as 6PPD, 7PPD or IPPD etc., in a manner known to the person skilled in the art in one of the Added mixing stages in the Fier ein of the rubber compound.
- the compound according to formula III) was then mixed into an exemplary rubber mixture according to the invention, as shown in Table 2.
- the resulting example according to the invention is marked E1.
- a rubber mixture C1 containing 6PPD serves as anti-aging agent instead of the compound of the formula III) with an otherwise identical composition.
- the amounts in Table 2 are given in units of phr.
- the mixture was produced according to the process customary in the rubber industry under customary conditions in three stages in a laboratory mixer with a volume of 300 milliliters to 3 liters, in which initially in the first mixing stage (basic mixing stage) all the components apart from the vulcanization system (sulphur and substances that influence vulcanization) were mixed for 200 to 600 seconds at 145 to 165°C, target temperatures of 152 to 157°C. In the second stage, the mixture from the first stage was mixed again. The ready mix was produced by adding the vulcanization system in the third stage (ready mix stage), with mixing at 90 to 120° C. for 180 to 300 seconds.
- Test specimens were produced from all the mixtures by vulcanization according to t95 to t100 (measured on a moving die rheometer according to ASTM D 5289-12/ISO 6502) under pressure at 160° C. to 170° C.
- test specimens of both V1 and E1 were aged (70 °C for 28 days in air).
- V1 The values obtained for V1 were each normalized to 100% as a reference.
- E1 difference between unaged and aged are given as performance % in relation to this respective V1 reference, with values greater than 100% being advantageous.
- the compound according to the invention according to formula III) as a representative of the compound according to formula I) results in improved protection against aging, since important properties such as the stress value at 300% elongation (modulus 300), the elongation at break and the rebound resilience are at a higher level for E1 after aging than for V1.
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Abstract
L'invention concerne un composé, un mélange de caoutchouc contenant ledit composé, un pneu de véhicule comprenant le mélange de caoutchouc dans au moins un élément, un procédé de préparation du composé et l'utilisation du composé en tant qu'agent de protection contre le vieillissement et/ou antiozonant et/ou colorant. Le composé selon l'invention présente la formule (I), dans laquelle A représente un radical aromatique portant éventuellement des substituants supplémentaires; et dans laquelle R1 est choisi dans le groupe constitué par xi) des radicaux aromatiques, les radicaux aromatiques portant éventuellement des substituants qui sont choisis dans le groupe constitué par les radicaux halogène, les radicaux cyano, les radicaux ester, les radicaux cétone, les radicaux éther et les radicaux thioéther, et xii) des radicaux aliphatiques linéaires, ramifiés et cycliques en C1 à C12, et xiii) des combinaisons de radicaux aromatiques et aliphatiques en C1 à C12.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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DE102021207926.1A DE102021207926A1 (de) | 2021-07-23 | 2021-07-23 | Verbindung, Verfahren zu deren Herstellung sowie Verwendung der Verbindung als Alterungsschutzmittel und/oder Ozonschutzmittel und/oder Farbstoff |
PCT/DE2022/200130 WO2023001340A1 (fr) | 2021-07-23 | 2022-06-14 | Composé, mélange de caoutchouc contenant le composé, pneu de véhicule comportant au moins un élément comprenant le mélange de caoutchouc, procédé de préparation du composé, et utilisation du composé en tant qu'agent de protection contre le vieillissement et/ou antiozonant et/ou colorant |
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EP4373678A1 true EP4373678A1 (fr) | 2024-05-29 |
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EP22740285.6A Pending EP4373678A1 (fr) | 2021-07-23 | 2022-06-14 | Composé, mélange de caoutchouc contenant le composé, pneu de véhicule comportant au moins un élément comprenant le mélange de caoutchouc, procédé de préparation du composé, et utilisation du composé en tant qu'agent de protection contre le vieillissement et/ou antiozonant et/ou colorant |
Country Status (5)
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EP (1) | EP4373678A1 (fr) |
KR (1) | KR20240067865A (fr) |
CN (1) | CN117693429A (fr) |
DE (1) | DE102021207926A1 (fr) |
WO (1) | WO2023001340A1 (fr) |
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DE3009547A1 (de) * | 1980-03-13 | 1981-09-24 | Henkel Kgaa | Desodorierende kosmetische zusammensetzungen |
ES2199454T5 (es) | 1997-08-21 | 2009-03-01 | Momentive Performance Materials Inc. | Agentes de acoplamiento de mercaptosilano bloqueados para cauchos con sustancia de relleno. |
DE60326735D1 (de) * | 2002-08-02 | 2009-04-30 | Genesoft Pharmaceuticals Inc | Biaryl-verbindungen mit antiinfektiver wirkung |
JP2004196699A (ja) | 2002-12-18 | 2004-07-15 | Shiseido Co Ltd | インドール誘導体及びその用途 |
US7968636B2 (en) | 2006-12-28 | 2011-06-28 | Continental Ag | Tire compositions and components containing silated cyclic core polysulfides |
US7968635B2 (en) | 2006-12-28 | 2011-06-28 | Continental Ag | Tire compositions and components containing free-flowing filler compositions |
US7968634B2 (en) | 2006-12-28 | 2011-06-28 | Continental Ag | Tire compositions and components containing silated core polysulfides |
US7968633B2 (en) | 2006-12-28 | 2011-06-28 | Continental Ag | Tire compositions and components containing free-flowing filler compositions |
JP6147585B2 (ja) | 2013-06-25 | 2017-06-14 | 東洋ゴム工業株式会社 | ゴム組成物及び空気入りタイヤ |
CA3086431A1 (fr) | 2017-12-20 | 2019-06-27 | Bristol-Myers Squibb Company | Composes indole amino utiles en tant qu'inhibiteurs de tlr |
DE102019212916A1 (de) * | 2019-08-28 | 2021-03-04 | Continental Reifen Deutschland Gmbh | Vernetzbare Kautschukmischung, Vulkanisat und Fahrzeugreifen |
-
2021
- 2021-07-23 DE DE102021207926.1A patent/DE102021207926A1/de active Pending
-
2022
- 2022-06-14 WO PCT/DE2022/200130 patent/WO2023001340A1/fr active Application Filing
- 2022-06-14 CN CN202280050354.XA patent/CN117693429A/zh active Pending
- 2022-06-14 KR KR1020247005039A patent/KR20240067865A/ko unknown
- 2022-06-14 EP EP22740285.6A patent/EP4373678A1/fr active Pending
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DE102021207926A1 (de) | 2023-01-26 |
CN117693429A (zh) | 2024-03-12 |
WO2023001340A1 (fr) | 2023-01-26 |
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