DK3280744T3 - [Bis(trihydrocarbylsilyl)aminosilyl]-funktionaliseret styren og fremgangsmåde til fremstilling deraf. - Google Patents
[Bis(trihydrocarbylsilyl)aminosilyl]-funktionaliseret styren og fremgangsmåde til fremstilling deraf. Download PDFInfo
- Publication number
- DK3280744T3 DK3280744T3 DK16718258.3T DK16718258T DK3280744T3 DK 3280744 T3 DK3280744 T3 DK 3280744T3 DK 16718258 T DK16718258 T DK 16718258T DK 3280744 T3 DK3280744 T3 DK 3280744T3
- Authority
- DK
- Denmark
- Prior art keywords
- carbon atoms
- group containing
- integer
- aryl
- alkyl group
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 16
- 238000000034 method Methods 0.000 title claims description 7
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 title description 33
- 125000004432 carbon atom Chemical group C* 0.000 claims description 48
- 125000003118 aryl group Chemical group 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 22
- 239000002904 solvent Substances 0.000 claims description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 16
- 229920001577 copolymer Polymers 0.000 claims description 13
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 9
- 229910000077 silane Inorganic materials 0.000 claims description 9
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 8
- 239000000178 monomer Substances 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 239000011593 sulfur Substances 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
- 150000001993 dienes Chemical class 0.000 claims description 4
- 229920002554 vinyl polymer Polymers 0.000 claims description 4
- 150000002681 magnesium compounds Chemical class 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 239000012298 atmosphere Substances 0.000 claims description 2
- 150000004292 cyclic ethers Chemical class 0.000 claims description 2
- 239000011261 inert gas Substances 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 125000003011 styrenyl group Chemical class [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 6
- -1 cyclic lithium amides Chemical class 0.000 description 34
- 150000003440 styrenes Chemical class 0.000 description 27
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 20
- 229920000642 polymer Polymers 0.000 description 18
- 239000000945 filler Substances 0.000 description 12
- 239000011777 magnesium Substances 0.000 description 12
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 11
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
- 229920003048 styrene butadiene rubber Polymers 0.000 description 11
- 229910052749 magnesium Inorganic materials 0.000 description 10
- 239000000377 silicon dioxide Substances 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 229920001971 elastomer Polymers 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000005060 rubber Substances 0.000 description 8
- 239000006229 carbon black Substances 0.000 description 7
- WGGLDBIZIQMEGH-UHFFFAOYSA-N 1-bromo-4-ethenylbenzene Chemical compound BrC1=CC=C(C=C)C=C1 WGGLDBIZIQMEGH-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 5
- 230000003993 interaction Effects 0.000 description 5
- 239000011630 iodine Chemical group 0.000 description 5
- 229910052740 iodine Chemical group 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 239000002174 Styrene-butadiene Substances 0.000 description 4
- 230000004913 activation Effects 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- 239000012300 argon atmosphere Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 230000000977 initiatory effect Effects 0.000 description 3
- 150000002680 magnesium Chemical class 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 239000012451 post-reaction mixture Substances 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- ZRZHXNCATOYMJH-UHFFFAOYSA-N 1-(chloromethyl)-4-ethenylbenzene Chemical compound ClCC1=CC=C(C=C)C=C1 ZRZHXNCATOYMJH-UHFFFAOYSA-N 0.000 description 2
- 238000005133 29Si NMR spectroscopy Methods 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- 125000002015 acyclic group Chemical group 0.000 description 2
- 238000009835 boiling Methods 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
- 239000006227 byproduct Substances 0.000 description 2
- 230000008034 disappearance Effects 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 229920001198 elastomeric copolymer Polymers 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 239000011256 inorganic filler Substances 0.000 description 2
- 229910003475 inorganic filler Inorganic materials 0.000 description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- NLLMRAQUKLLMHE-UHFFFAOYSA-M magnesium;ethenylbenzene;bromide Chemical compound [Mg+2].[Br-].C=CC1=CC=[C-]C=C1 NLLMRAQUKLLMHE-UHFFFAOYSA-M 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 150000002901 organomagnesium compounds Chemical class 0.000 description 2
- 125000002524 organometallic group Chemical group 0.000 description 2
- 229920002857 polybutadiene Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000004611 spectroscopical analysis Methods 0.000 description 2
- 239000011115 styrene butadiene Substances 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- HMDQPBSDHHTRNI-UHFFFAOYSA-N 1-(chloromethyl)-3-ethenylbenzene Chemical compound ClCC1=CC=CC(C=C)=C1 HMDQPBSDHHTRNI-UHFFFAOYSA-N 0.000 description 1
- IWTYTFSSTWXZFU-UHFFFAOYSA-N 3-chloroprop-1-enylbenzene Chemical class ClCC=CC1=CC=CC=C1 IWTYTFSSTWXZFU-UHFFFAOYSA-N 0.000 description 1
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 125000005002 aryl methyl group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 229910052681 coesite Inorganic materials 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 229910052906 cristobalite Inorganic materials 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 1
- AHNJTQYTRPXLLG-UHFFFAOYSA-N lithium;diethylazanide Chemical compound [Li+].CC[N-]CC AHNJTQYTRPXLLG-UHFFFAOYSA-N 0.000 description 1
- 238000010551 living anionic polymerization reaction Methods 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000002715 modification method Methods 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 150000005041 phenanthrolines Chemical class 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 125000005372 silanol group Chemical group 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 229910052682 stishovite Inorganic materials 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
- VOSJXMPCFODQAR-UHFFFAOYSA-N trisilylamine group Chemical class [SiH3]N([SiH3])[SiH3] VOSJXMPCFODQAR-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F12/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F12/02—Monomers containing only one unsaturated aliphatic radical
- C08F12/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F12/14—Monomers containing only one unsaturated aliphatic radical containing one ring substituted by hetero atoms or groups containing heteroatoms
- C08F12/26—Nitrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F212/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F212/02—Monomers containing only one unsaturated aliphatic radical
- C08F212/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F212/14—Monomers containing only one unsaturated aliphatic radical containing one ring substituted by heteroatoms or groups containing heteroatoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F212/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F212/02—Monomers containing only one unsaturated aliphatic radical
- C08F212/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F212/14—Monomers containing only one unsaturated aliphatic radical containing one ring substituted by heteroatoms or groups containing heteroatoms
- C08F212/26—Nitrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F230/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
- C08F230/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal
- C08F230/08—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F236/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F236/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F236/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
- C08F236/10—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated with vinyl-aromatic monomers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/40—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals
- C07C15/42—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals monocyclic
- C07C15/44—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals monocyclic the hydrocarbon substituent containing a carbon-to-carbon double bond
- C07C15/46—Styrene; Ring-alkylated styrenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Claims (11)
1. Styrenderivat med formlen (I)
(I) hvor R1 og R2 kan være ens eller forskellige og betegner et led udvalgt fra gruppen bestående af: a) en enkeltbinding; b) -(CH2)n-, hvor n står for et heltal fra 1 til 12; c) -(CH2CH2Y)n-, hvor n står for et heltal fra 1 til 12, og Y kan uafhængigt være oxygen eller svovl; d) -CH2-(CH2CH2Y)n-CH2-, hvor n står for et heltal fra 1 til 12, og Y kan uafhængigt være oxygen eller svovl; e) -(CH2CH2NR)n-, hvor n står for et heltal fra 1 til 12, og R kan uafhængigt stå for en alkylgruppe indeholdende fra 1 til 10 carbonatomer, eller en aryl- eller aralkylgruppe indeholdende fra 6 til 10 carbonatomer; f) -CH2-(CH2CH2NR)n-CH2-, hvor n står for et heltal fra 1 til 12, og R kan uafhængigt stå for en alkylgruppe indeholdende fra 1 til 10 carbonatomer, eller en aryl- eller aralkylgruppe indeholdende fra 6 til 10 carbonatomer; g) -(CH2SiR2)n-, hvor n står for et heltal fra 1 til 12, og R kan uafhængigt stå for en alkylgruppe indeholdende fra 1 til 10 carbonatomer, eller en aryl- eller aralkylgruppe indeholdende fra 6 til 10 carbonatomer; h) -CH2-(CH2SiR2)n-CH2-, hvor n står for et heltal fra 1 til 12, og R kan uafhængigt stå for en alkylgruppe indeholdende fra 1 til 10 carbonatomer, eller en aryl- eller aralkylgruppe indeholdende fra 6 til 10 carbonatomer; i) -(OSiR2)n-, hvor n står for et heltal fra 1 til 12, og R kan uafhængigt stå for en alkylgruppe indeholdende fra 1 til 10 carbonatomer, eller en aryl- eller aralkylgruppe indeholdende fra 6 til 10 carbonatomer; og j) -CH2-(OSiR2)n-CH2-, hvor n står for et heltal fra 1 til 12, og R kan uafhængigt stå for en alkylgruppe indeholdende fra 1 til 10 carbonatomer, eller en aryl- eller aralkylgruppe indeholdende fra 6 til 10 carbonatomer; hvor R3, R4, R5 og R5 kan være ens eller forskellige og står for en alkylgruppe indeholdende fra 1 til 10 carbonatomer, eller en aryl- eller aralkylgruppe indeholdende fra 6 til 10 carbonatomer; og R7 og R8 kan være ens eller forskellige, og hver R7 og R8 står uafhængigt for en alkylgruppe indeholdende fra 1 til 10 carbonatomer, eller en aryl- eller aralkylgruppe indeholdende fra 6 til 10 carbonatomer.
2. Styrenderivat ifølge krav 1, som er af formlen (la) eller (Ib)
(la) , (lb) .
3. Styrenderivat ifølge krav 1 eller krav 2, hvor R1 er udvalgt fra gruppen bestående af: a) en enkeltbinding; og b) -(CH2)n-, hvor n står for et heltal fra 1 til 12, fortrinsvis hvor n er 1 eller 2, navnlig hvor n er 1.
4. Styrenderivat ifølge krav 3 hvor R1 er -(CH2)n-, hvor n står for et heltal fra 1 til 5, fortrinsvis hvor n står for et heltal fra 1 til 3, navnlig hvor n er 1.
5. Styrenderivat ifølge et hvilket som helst af de foregående krav, hvor R2 er b) -(CH2)n-, hvor n står for et heltal fra 1 til 12, fortrinsvis hvor n står for et heltal fra 1 til 5, mere foretrukket hvor n står for et heltal fra 1 til 3, navnlig hvor n er 2.
6. Styrenderivat ifølge et hvilket som helst af de foregående krav, hvor R3, R4, R5 og R5 kan være ens eller forskellige og står for CH3 eller C6H5, fortrinsvis hvor R3, R4, R5 og R5 alle står for CH3.
7. Styrenderivat ifølge et hvilket som helst af de foregående krav, hvor R7 og R8 alle står for CH3, fortrinsvis hvor styrenderivatet er af formlen (1), (2), (3), (4), (5), eller (6)
fortrinsvis hvor styrenderivatet er af formlen (1), (2), (4) eller (5); mest foretrukket hvor styrenderivatet er af formlen (1), (4), eller (5).
8. Fremgangsmåde til fremstilling af et styrenderivat med formlen (I)
(i), hvor R1 og R2 kan være ens eller forskellige og betegner et led udvalgt fra gruppen bestående af: a) en enkeltbinding; b) -(CH2)n-, hvor n står for et heltal fra 1 til 12; c) -(CH2CH2Y)n-, hvor n står for et heltal fra 1 til 12, og Y kan uafhængigt være oxygen eller svovl; d) -CH2-(CH2CH2Y)n-CH2-, hvor n står for et heltal fra 1 til 12, og Y kan uafhængigt være oxygen eller svovl; e) -(CH2CH2NR)n-, hvor n står for et heltal fra 1 til 12, og R kan uafhængigt stå for en alkylgruppe indeholdende fra 1 til 10 carbonatomer, eller en aryl- eller aralkylgruppe indeholdende fra 6 til 10 carbonatomer; f) -CH2-(CH2CH2NR)n-CH2-, hvor n står for et heltal fra 1 til 12, og R kan uafhængigt stå for en alkylgruppe indeholdende fra 1 til 10 carbonatomer, eller en aryl- eller aralkylgruppe indeholdende fra 6 til 10 carbonatomer; g) -(CH2SiR2)n-, hvor n står for et heltal fra 1 til 12, og R kan uafhængigt stå for en alkylgruppe indeholdende fra 1 til 10 carbonatomer, eller en aryl- eller aralkylgruppe indeholdende fra 6 til 10 carbonatomer; h) -CH2-(CH2SiR2)n-CH2-, hvor n står for et heltal fra 1 til 12, og R kan uafhængigt stå for en alkylgruppe indeholdende fra 1 til 10 carbonatomer, eller en aryl- eller aralkylgruppe indeholdende fra 6 til 10 carbonatomer; i) -(OSiR2)n-, hvor n står for et heltal fra 1 til 12, og R kan uafhængigt stå for en alkylgruppe indeholdende fra 1 til 10 carbonatomer, eller en aryl- eller aralkylgruppe indeholdende fra 6 til 10 carbonatomer; og j) -CH2-(OSiR2)n-CH2-, hvor n står for et heltal fra 1 til 12, og R kan uafhængigt stå for en alkylgruppe indeholdende fra 1 til 10 carbonatomer, eller en aryl- eller aralkylgruppe indeholdende fra 6 til 10 carbonatomer; hvor R3, R4, R5 og R5 kan være ens eller forskellige og står for en alkylgruppe indeholdende
fra 1 til 10 carbonatomer, eller en aryl- eller aralkylgruppe indeholdende fra 6 til 10 carbonatomer; og R7 og R8 kan være ens eller forskellige, og hver R7 og R8 står uafhængigt for en alkylgruppe indeholdende fra 1 til 10 carbonatomer, eller en aryl- eller aralkylgruppe indeholdende fra 6 til 10 carbonatomer; hvor en silanmed formlen (II)
di), hvor X1 er udvalgt blandt chlor-, brom- og iodatomer, og R2, R3, R4, R5, R5, R7 og R8 er som defineret ovenfor, omsættes med en magnesiumforbindelse med formlen (III),
(III) hvor X2 er udvalgt blandt chlor-, brom- og iodatomer, og R1 er som defineret ovenfor.
9. Fremgangsmåde ifølge krav 8, hvor reaktionen udføres i et organisk opløsningsmiddel i en inert gasatmosfære, fortrinsvis hvor reaktionen udføres i et alifatisk eller cyklisk etheropløsningsmiddel, navnlig hvor opløsningsmidlet er tetrahydrofuran (THF).
10. Anvendelse af styrenderivatet ifølge et hvilket som helst af kravene 1 til 7 til fremstilling af en copolymer deraf.
11. Anvendelse ifølge krav 10, hvor copolymeren omfatter gentagelsesenheder, der er afledt af A) 20 % efter vægt til 99,95 % efter vægt af copolymeren af en eller flere dienmonomerer; B) 0 % efter vægt til 60 % efter vægt af copolymeren af en eller flere vinylaromatiske monomerer; og C) 0,05 % efter vægt til 50 % efter vægt af copolymeren af en eller flere styrenderivater med formlen (I)
(I), hvor R1 og R2 kan være ens eller forskellige.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP15461526 | 2015-04-10 | ||
PCT/EP2016/057735 WO2016162473A1 (en) | 2015-04-10 | 2016-04-08 | [bis(trihydrocarbylsilyl)aminosilyl]-functionalized styrene and a method for its preparation |
Publications (1)
Publication Number | Publication Date |
---|---|
DK3280744T3 true DK3280744T3 (da) | 2018-10-29 |
Family
ID=52991679
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DK16718258.3T DK3280744T3 (da) | 2015-04-10 | 2016-04-08 | [Bis(trihydrocarbylsilyl)aminosilyl]-funktionaliseret styren og fremgangsmåde til fremstilling deraf. |
Country Status (20)
Country | Link |
---|---|
US (1) | US10259830B2 (da) |
EP (1) | EP3280744B1 (da) |
JP (1) | JP6488423B2 (da) |
KR (1) | KR102205883B1 (da) |
CN (1) | CN107690444B (da) |
AU (1) | AU2016244358A1 (da) |
BR (1) | BR112017021376A2 (da) |
CA (1) | CA2981118A1 (da) |
DK (1) | DK3280744T3 (da) |
EA (1) | EA036381B1 (da) |
ES (1) | ES2692043T3 (da) |
HU (1) | HUE039808T2 (da) |
IL (1) | IL254878A0 (da) |
MX (1) | MX2017013013A (da) |
PL (1) | PL3280744T3 (da) |
RS (1) | RS57959B1 (da) |
SG (1) | SG11201707912WA (da) |
TN (1) | TN2017000435A1 (da) |
WO (1) | WO2016162473A1 (da) |
ZA (1) | ZA201707594B (da) |
Families Citing this family (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
SG11201707986VA (en) * | 2015-04-10 | 2017-10-30 | Synthos Sa | Elastomeric copolymers based on [bis(trihydrocarbylsilyl)aminosilyl]-functionalized styrene and their use in the preparation of rubbers |
RS58418B1 (sr) | 2015-04-10 | 2019-04-30 | Synthos Sa | Inicijatori kopolimerizacije dienskih monomera i vinil-aromatičnih monomera |
ES2714552T3 (es) | 2016-10-06 | 2019-05-29 | Synthos Dwory 7 Spolka Z Ograniczona Odpowiedzialnoscia Spolka Jawna | Estireno funcionalizado con [bis(trihidrocarbilsilil aminosililo] y un método para su preparación |
CA3011781A1 (en) | 2016-10-06 | 2018-04-12 | Synthos S.A. | Elastomeric copolymers based on [bis(trihydrocarbylsilyl)aminosilyl]-functionalized styrene and their use in the preparation of rubbers |
US11312843B2 (en) | 2017-08-08 | 2022-04-26 | Synthos Dwory 7 Spolka Z Ograniczona Odpowiedzialnoscia Spolka Jawna | Bissilylaminosilyl-functionalized conjugated dienes and their use in the production of rubbers |
WO2019030059A1 (en) | 2017-08-08 | 2019-02-14 | Synthos Dwory 7 Spolka Z Ograniczona Odpowiedzialnoscia Spolka Jawna | CONJUGATED DIENNA FUNCTIONALIZED BY BISSILYLAMINOSILYL AND METHODS FOR THEIR PREPARATION |
WO2019118678A1 (en) | 2017-12-14 | 2019-06-20 | Bridgestone Corporation | Coupled polymer products, methods of making and compositions containing |
WO2019197455A1 (en) * | 2018-04-11 | 2019-10-17 | Synthos S.A. | Mixtures of aminosilyl-functionalized styrenes, their preparation and their use in the production of elastomeric copolymers |
EA202190668A1 (ru) | 2018-09-03 | 2021-05-27 | Синтос С.А. | Аминосилил-функционализованные сопряженные диены, их получение и их использование при производстве каучуков |
KR20210121115A (ko) | 2019-01-24 | 2021-10-07 | 신도스 에스.에이. | 비스실릴아미노-작용기화된 컨쥬게이션 다이엔, 이의 제조 및 고무의 제조에서 이의 용도 |
Family Cites Families (37)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CH415623A (de) | 1960-11-11 | 1966-06-30 | Monsanto Co | Verfahren zur Herstellung von Stickstoff-Silicium-Verbindungen |
US3109871A (en) | 1960-12-27 | 1963-11-05 | Phillips Petroleum Co | Production and curing of polyfunctional terminally reactive polymers |
US4196154A (en) | 1977-10-11 | 1980-04-01 | The Dow Chemical Company | Soluble multifunctional lithium containing initiator |
JPS5953515A (ja) * | 1982-09-22 | 1984-03-28 | Tounen Sekiyu Kagaku Kk | 新規リビングブロツク共重合体及びその製造方法 |
JPS63118343A (ja) | 1986-11-07 | 1988-05-23 | Japan Synthetic Rubber Co Ltd | 共役ジエン系ゴム組成物 |
JPH0778151B2 (ja) * | 1987-07-17 | 1995-08-23 | 日本合成ゴム株式会社 | ゴム組成物 |
DE3729144A1 (de) | 1987-09-01 | 1989-03-09 | Basf Ag | Bifunktionelle alkaliverbindungen, verfahren zu ihrer herstellung und verwendung als polymerisationsinitiatoren |
US4935471A (en) | 1987-10-15 | 1990-06-19 | The Goodyear Tire & Rubber Company | Capped polydienes |
JP3141958B2 (ja) * | 1992-02-28 | 2001-03-07 | ホーヤ株式会社 | 気体透過性重合体およびその製造方法 |
US5329005A (en) | 1992-10-02 | 1994-07-12 | Bridgestone Corporation | Soluble anionic polymerization initiators and preparation thereof |
US5527753A (en) | 1994-12-13 | 1996-06-18 | Fmc Corporation | Functionalized amine initiators for anionic polymerization |
DE19536843A1 (de) * | 1995-10-02 | 1997-04-03 | Bayer Ag | (Co)Polymerisate auf Basis von Vinyl-Einheiten und ihre Verwendung in elektrolumineszierenden Anordnungen |
US6627721B1 (en) | 2002-09-19 | 2003-09-30 | The Goodyear Tire & Rubber Company | Functionalized elastomers |
US6627722B2 (en) | 2000-12-05 | 2003-09-30 | Stephan Rodewald | Functionalized elastomers |
US6515087B2 (en) | 2000-12-14 | 2003-02-04 | The Goodyear Tire & Rubber Company | Synthesis of elastomers having low hysteresis |
JP2004059781A (ja) | 2002-07-30 | 2004-02-26 | Jsr Corp | ブロック共重合体及び該共重合体を含有するアスファルト組成物 |
US6825306B2 (en) | 2002-08-16 | 2004-11-30 | The Goodyear Tire & Rubber Company | Functionalized monomers for synthesis of rubbery polymers |
US6933358B2 (en) | 2002-08-16 | 2005-08-23 | The Goodyear Tire & Rubber Company | Functionalized monomers for synthesis of rubbery polymers |
US6753447B2 (en) | 2002-08-16 | 2004-06-22 | The Goodyear Tire & Rubber Company | Functionalized monomers for synthesis of rubbery polymers |
DE602005017635D1 (de) * | 2004-08-10 | 2009-12-24 | Jsr Corp | Harzzusammensetzung und formteil daraus |
BRPI0604797A (pt) * | 2005-11-30 | 2007-10-09 | Goodyear Tire & Rubber | polìmeros de borracha funcionalizados |
EP2130842B1 (en) * | 2007-03-23 | 2013-05-15 | JSR Corporation | Method for producing modified conjugated diene polymer, modified conjugated diene polymer, and rubber composition |
JPWO2009133888A1 (ja) | 2008-04-30 | 2011-09-01 | 株式会社ブリヂストン | 変性共役ジエン系共重合体の製造方法、その方法により得られた変性共役ジエン系共重合体、ゴム組成物及びタイヤ |
CN101724184B (zh) | 2008-10-29 | 2013-05-01 | 住友橡胶工业株式会社 | 橡胶组合物及轮胎 |
US20100116404A1 (en) | 2008-11-11 | 2010-05-13 | Annette Lechtenboehmer | Tire with component containing polyketone short fiber and functionalized elastomer |
US20100152364A1 (en) | 2008-12-12 | 2010-06-17 | The Goodyear Tire & Rubber Company | Polymers, rubber compositions, and tires |
JP2011074310A (ja) * | 2009-10-01 | 2011-04-14 | Sumitomo Rubber Ind Ltd | 共重合体ならびにそれを用いたゴム組成物および空気入りタイヤ |
EP2516478B1 (en) | 2009-12-21 | 2014-06-11 | Styron Europe GmbH | Modified polymer compositions |
JP2011252137A (ja) | 2010-05-06 | 2011-12-15 | Sumitomo Chemical Co Ltd | 共役ジエン系重合体、共役ジエン系重合体組成物、及び、共役ジエン系重合体の製造方法 |
US8334339B2 (en) | 2010-08-11 | 2012-12-18 | Sumitomo Chemical Co., Ltd. | Conjugated diene-based polymer, conjugated diene-based polymer composition, and process for producing conjugated diene-based polymer |
EA201490496A1 (ru) | 2011-08-26 | 2014-08-29 | Асахи Касеи Кемикалз Корпорейшн | Способ получения модифицированных полимеров сопряженных диенов, модифицированные полимеры сопряженных диенов, композиции модифицированных полимеров сопряженных диенов, композиции каучука и автомобильные шины |
US9120890B2 (en) | 2011-11-24 | 2015-09-01 | Sumitomo Rubber Industries, Ltd. | Rubber composition and pneumatic tire |
JP5862509B2 (ja) * | 2012-08-09 | 2016-02-16 | Jsr株式会社 | 樹脂組成物及びその製造方法 |
SG11201707986VA (en) | 2015-04-10 | 2017-10-30 | Synthos Sa | Elastomeric copolymers based on [bis(trihydrocarbylsilyl)aminosilyl]-functionalized styrene and their use in the preparation of rubbers |
RS58418B1 (sr) | 2015-04-10 | 2019-04-30 | Synthos Sa | Inicijatori kopolimerizacije dienskih monomera i vinil-aromatičnih monomera |
CA3011781A1 (en) | 2016-10-06 | 2018-04-12 | Synthos S.A. | Elastomeric copolymers based on [bis(trihydrocarbylsilyl)aminosilyl]-functionalized styrene and their use in the preparation of rubbers |
ES2714552T3 (es) | 2016-10-06 | 2019-05-29 | Synthos Dwory 7 Spolka Z Ograniczona Odpowiedzialnoscia Spolka Jawna | Estireno funcionalizado con [bis(trihidrocarbilsilil aminosililo] y un método para su preparación |
-
2016
- 2016-04-08 RS RS20181325A patent/RS57959B1/sr unknown
- 2016-04-08 EA EA201792252A patent/EA036381B1/ru not_active IP Right Cessation
- 2016-04-08 WO PCT/EP2016/057735 patent/WO2016162473A1/en active Application Filing
- 2016-04-08 SG SG11201707912WA patent/SG11201707912WA/en unknown
- 2016-04-08 US US15/565,338 patent/US10259830B2/en not_active Expired - Fee Related
- 2016-04-08 MX MX2017013013A patent/MX2017013013A/es active IP Right Grant
- 2016-04-08 EP EP16718258.3A patent/EP3280744B1/en active Active
- 2016-04-08 PL PL16718258T patent/PL3280744T3/pl unknown
- 2016-04-08 KR KR1020177032696A patent/KR102205883B1/ko active IP Right Grant
- 2016-04-08 JP JP2018503713A patent/JP6488423B2/ja active Active
- 2016-04-08 AU AU2016244358A patent/AU2016244358A1/en not_active Abandoned
- 2016-04-08 CN CN201680033779.4A patent/CN107690444B/zh active Active
- 2016-04-08 DK DK16718258.3T patent/DK3280744T3/da active
- 2016-04-08 ES ES16718258.3T patent/ES2692043T3/es active Active
- 2016-04-08 CA CA2981118A patent/CA2981118A1/en not_active Abandoned
- 2016-04-08 TN TNP/2017/000435A patent/TN2017000435A1/en unknown
- 2016-04-08 BR BR112017021376A patent/BR112017021376A2/pt active Search and Examination
- 2016-04-08 HU HUE16718258A patent/HUE039808T2/hu unknown
-
2017
- 2017-10-03 IL IL254878A patent/IL254878A0/en unknown
- 2017-11-09 ZA ZA2017/07594A patent/ZA201707594B/en unknown
Also Published As
Publication number | Publication date |
---|---|
MX2017013013A (es) | 2018-03-12 |
JP6488423B2 (ja) | 2019-03-20 |
SG11201707912WA (en) | 2017-10-30 |
EA201792252A1 (ru) | 2018-02-28 |
HUE039808T2 (hu) | 2019-02-28 |
KR20180016355A (ko) | 2018-02-14 |
EA036381B1 (ru) | 2020-11-02 |
JP2018513907A (ja) | 2018-05-31 |
PL3280744T3 (pl) | 2019-03-29 |
BR112017021376A2 (pt) | 2018-07-03 |
AU2016244358A1 (en) | 2017-11-02 |
ES2692043T3 (es) | 2018-11-29 |
IL254878A0 (en) | 2017-12-31 |
EP3280744A1 (en) | 2018-02-14 |
WO2016162473A1 (en) | 2016-10-13 |
TN2017000435A1 (en) | 2019-04-12 |
RS57959B1 (sr) | 2019-01-31 |
CA2981118A1 (en) | 2016-10-13 |
US20180065996A1 (en) | 2018-03-08 |
CN107690444A (zh) | 2018-02-13 |
US10259830B2 (en) | 2019-04-16 |
EP3280744B1 (en) | 2018-08-15 |
CN107690444B (zh) | 2020-02-11 |
KR102205883B1 (ko) | 2021-01-22 |
ZA201707594B (en) | 2018-11-28 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
DK3280744T3 (da) | [Bis(trihydrocarbylsilyl)aminosilyl]-funktionaliseret styren og fremgangsmåde til fremstilling deraf. | |
DK3341423T3 (da) | [Bis(trihydrocarbylsilyl)aminosilyl]-funktionaliseret styren og fremgangsmåde til fremstilling deraf | |
US10066076B1 (en) | Method for preparing conjugated diene polymer, composition comprising the same and tire comprising the composition | |
DK3280766T3 (da) | Elastomere copolymerer på basis af [bis(trihydrocarbylsilyl)aminosilyl]-funktionaliseret styren og deres anvendelse til fremstilling af gummistoffer | |
JP5473952B2 (ja) | 官能化ポリマー及びその製造のための開始剤 | |
CN104718224A (zh) | 氨基硅烷改性的聚合物 | |
CN102933609A (zh) | 改性聚合物组合物 | |
CN102482382A (zh) | 羟芳基官能化聚合物 | |
CN108137621B (zh) | 制备氨基硅烷类化合物的新方法 | |
CN110655697B (zh) | 改性共轭二烯系聚合物混合物的制造方法 | |
JP2009209306A5 (da) | ||
CN110248969B (zh) | 用氨基化锂引发剂连续合成经改性的二烯弹性体的方法 | |
CA2414045A1 (en) | Polymers modified by functional groups | |
KR20210124053A (ko) | 공액 디엔계 중합체, 공액 디엔계 중합체의 제조 방법, 공액 디엔계 중합체 조성물, 및 고무 조성물 | |
CN111971316B (zh) | 氨基硅烷基官能化苯乙烯的混合物、它们的制备及它们在弹性体共聚物生产中的使用 |