WO2018065070A1 - Aminosiloxanes secondaires et son procédé de production - Google Patents
Aminosiloxanes secondaires et son procédé de production Download PDFInfo
- Publication number
- WO2018065070A1 WO2018065070A1 PCT/EP2016/074062 EP2016074062W WO2018065070A1 WO 2018065070 A1 WO2018065070 A1 WO 2018065070A1 EP 2016074062 W EP2016074062 W EP 2016074062W WO 2018065070 A1 WO2018065070 A1 WO 2018065070A1
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- WIPO (PCT)
- Prior art keywords
- general formula
- radical
- number equal
- aminosiloxanes
- atoms
- Prior art date
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- -1 aminosiloxanes Chemical group 0.000 title claims abstract description 107
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 15
- 239000000203 mixture Substances 0.000 claims abstract description 14
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims abstract description 12
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 10
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims abstract description 8
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims abstract description 8
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 8
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 8
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 8
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 8
- 229910002092 carbon dioxide Inorganic materials 0.000 claims abstract description 6
- 229920001400 block copolymer Polymers 0.000 claims abstract description 5
- 239000001569 carbon dioxide Substances 0.000 claims abstract description 5
- 239000002537 cosmetic Substances 0.000 claims abstract description 5
- 238000009472 formulation Methods 0.000 claims abstract description 5
- 238000009988 textile finishing Methods 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 43
- 238000006243 chemical reaction Methods 0.000 claims description 25
- 150000001412 amines Chemical class 0.000 claims description 23
- 150000001875 compounds Chemical class 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 11
- 150000003377 silicon compounds Chemical class 0.000 claims description 10
- 238000009833 condensation Methods 0.000 claims description 9
- 230000005494 condensation Effects 0.000 claims description 9
- 229930195733 hydrocarbon Natural products 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 230000003301 hydrolyzing effect Effects 0.000 claims description 8
- 239000004215 Carbon black (E152) Substances 0.000 claims description 7
- 125000004122 cyclic group Chemical group 0.000 claims description 7
- 239000007789 gas Substances 0.000 claims description 7
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims description 6
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 claims description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000011630 iodine Substances 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- ORGHESHFQPYLAO-UHFFFAOYSA-N vinyl radical Chemical compound C=[CH] ORGHESHFQPYLAO-UHFFFAOYSA-N 0.000 claims description 2
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 abstract description 2
- 239000002912 waste gas Substances 0.000 abstract 1
- 239000002585 base Substances 0.000 description 24
- 239000000047 product Substances 0.000 description 23
- 238000004821 distillation Methods 0.000 description 13
- 150000003839 salts Chemical class 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000012071 phase Substances 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- 238000011067 equilibration Methods 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 8
- 150000004820 halides Chemical group 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 238000000926 separation method Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 6
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 5
- 229910000077 silane Inorganic materials 0.000 description 5
- BPGIOCZAQDIBPI-UHFFFAOYSA-N 2-ethoxyethanamine Chemical compound CCOCCN BPGIOCZAQDIBPI-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 3
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- 239000012454 non-polar solvent Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 230000001681 protective effect Effects 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- ILRZBPLDJKEWRW-UHFFFAOYSA-N 1-ethoxyethanamine Chemical compound CCOC(C)N ILRZBPLDJKEWRW-UHFFFAOYSA-N 0.000 description 2
- 125000006017 1-propenyl group Chemical group 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical class [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 150000005840 aryl radicals Chemical class 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- HCFPRFJJTHMING-UHFFFAOYSA-N ethane-1,2-diamine;hydron;chloride Chemical compound [Cl-].NCC[NH3+] HCFPRFJJTHMING-UHFFFAOYSA-N 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 238000006459 hydrosilylation reaction Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 150000004686 pentahydrates Chemical class 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 150000004756 silanes Chemical class 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- MFGOFGRYDNHJTA-UHFFFAOYSA-N 2-amino-1-(2-fluorophenyl)ethanol Chemical compound NCC(O)C1=CC=CC=C1F MFGOFGRYDNHJTA-UHFFFAOYSA-N 0.000 description 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 1
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Inorganic materials [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- NBGGEWGFZUDQKZ-UHFFFAOYSA-N chloromethyl-[chloromethyl(dimethyl)silyl]oxy-dimethylsilane Chemical compound ClC[Si](C)(C)O[Si](C)(C)CCl NBGGEWGFZUDQKZ-UHFFFAOYSA-N 0.000 description 1
- ZCSLOBFDVTWIBL-UHFFFAOYSA-N chloromethyl-methoxy-dimethylsilane Chemical compound CO[Si](C)(C)CCl ZCSLOBFDVTWIBL-UHFFFAOYSA-N 0.000 description 1
- 230000003749 cleanliness Effects 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- JJQZDUKDJDQPMQ-UHFFFAOYSA-N dimethoxy(dimethyl)silane Chemical compound CO[Si](C)(C)OC JJQZDUKDJDQPMQ-UHFFFAOYSA-N 0.000 description 1
- CVQVSVBUMVSJES-UHFFFAOYSA-N dimethoxy-methyl-phenylsilane Chemical compound CO[Si](C)(OC)C1=CC=CC=C1 CVQVSVBUMVSJES-UHFFFAOYSA-N 0.000 description 1
- YYLGKUPAFFKGRQ-UHFFFAOYSA-N dimethyldiethoxysilane Chemical compound CCO[Si](C)(C)OCC YYLGKUPAFFKGRQ-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- ZLNAFSPCNATQPQ-UHFFFAOYSA-N ethenyl-dimethoxy-methylsilane Chemical compound CO[Si](C)(OC)C=C ZLNAFSPCNATQPQ-UHFFFAOYSA-N 0.000 description 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000002803 fossil fuel Substances 0.000 description 1
- 230000009395 genetic defect Effects 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052756 noble gas Inorganic materials 0.000 description 1
- 150000002835 noble gases Chemical class 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- HMMGMWAXVFQUOA-UHFFFAOYSA-N octamethylcyclotetrasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 HMMGMWAXVFQUOA-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- DJFBJKSMACBYBD-UHFFFAOYSA-N phosphane;hydrate Chemical group O.P DJFBJKSMACBYBD-UHFFFAOYSA-N 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000009419 refurbishment Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- CPRMKOQKXYSDML-UHFFFAOYSA-M rubidium hydroxide Inorganic materials [OH-].[Rb+] CPRMKOQKXYSDML-UHFFFAOYSA-M 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 229940125723 sedative agent Drugs 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- BJQWBACJIAKDTJ-UHFFFAOYSA-N tetrabutylphosphanium Chemical compound CCCC[P+](CCCC)(CCCC)CCCC BJQWBACJIAKDTJ-UHFFFAOYSA-N 0.000 description 1
- ZOMVKCHODRHQEV-UHFFFAOYSA-M tetraethylphosphanium;hydroxide Chemical compound [OH-].CC[P+](CC)(CC)CC ZOMVKCHODRHQEV-UHFFFAOYSA-M 0.000 description 1
- MYXKPFMQWULLOH-UHFFFAOYSA-M tetramethylazanium;hydroxide;pentahydrate Chemical compound O.O.O.O.O.[OH-].C[N+](C)(C)C MYXKPFMQWULLOH-UHFFFAOYSA-M 0.000 description 1
- CRUVUWATNULHFA-UHFFFAOYSA-M tetramethylphosphanium;hydroxide Chemical compound [OH-].C[P+](C)(C)C CRUVUWATNULHFA-UHFFFAOYSA-M 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000007669 thermal treatment Methods 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 238000010626 work up procedure Methods 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
- C07F7/0834—Compounds having one or more O-Si linkage
- C07F7/0838—Compounds with one or more Si-O-Si sequences
- C07F7/0872—Preparation and treatment thereof
- C07F7/0874—Reactions involving a bond of the Si-O-Si linkage
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
- A61K8/89—Polysiloxanes
- A61K8/896—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate
- A61K8/898—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate containing nitrogen, e.g. amodimethicone, trimethyl silyl amodimethicone or dimethicone propyl PG-betaine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- 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
- C07F7/0834—Compounds having one or more O-Si linkage
- C07F7/0838—Compounds with one or more Si-O-Si sequences
-
- 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
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/643—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
- D06M15/6436—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain containing amino groups
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/10—General cosmetic use
Definitions
- the invention relates to aminosiloxanes, a process for their preparation and use for textile finishing, for cosmetic formulations, the treatment of surfaces, for the preparation of block copolymers or for the binding and removal of carbon dioxide from exhaust gases.
- aminosiloxanes are among the most important organically functionalized organopolysiloxanes and are used successfully in many different fields of application. These include textile equipment (eg US
- WO 2009/019161 describes a process for the production of primary and secondary aminoorganyl-triorganylsilanes of the general formula R '3-n R 1 n Si-R 2 -NR 3 R 4 by reacting cyclic or acyclic amines of the general formula H-NR 3 R 4 with (haloorganyl) silanes of the general formula R 3 '_ n R 1 n Si-R 2 -X, where first the (haloorganyl) silane and the amine are reacted, and then releases the amine by addition of a base from the salt formed is, wherein the salt of the base formed at temperature ⁇ 200 ° C is liquid and can be separated.
- Haloalkylsiloxanes in which the alkyl group between Si and N ⁇ 3 contain methylene units are generally prepared by transition metal-catalyzed reaction of an Si-H group with allyl halides (hydrosilylation) and subsequent nucleophilic substitution of the halide by the desired amine.
- transition metal catalysts mostly Pt,
- Allyl halides are harmful substances.
- allyl chloride is suspected to cause genetic defects or to cause cancer.
- the invention relates to aminosiloxanes (A) of the general formula 1 in which
- R 1 , R 4 are independently a substituted or
- Heteroatom selected from the group consisting of N, O, S, and P may be replaced,
- R 2 , R 3 are independently a substituted or
- n is a number equal to 1 or 2 and
- n is an integer equal to or greater than 0
- Aminosiloxanes (A) are inexpensive and safe in good
- Yields can be produced. They are suitable, for example, for textile finishing, for cosmetic formulations, for the treatment of surfaces, for the production of block copolymers and in particular for the binding and removal of carbon dioxide from exhaust gases.
- the hydrocarbon radicals R 1 , R 4 may be alkyl radicals, such as the methyl, ethyl, n-propyl, iso-propyl, 1-n-butyl, 2-n-butyl, iso-butyl, tert. Butyl, n-pentyl, iso-pentyl, neo-pentyl, tert.
- -Pentyl radical Hexyl radicals, such as the n-hexyl radical; Heptyl radicals, such as the n-heptyl radical; Octyl radicals, such as the n-octyl radical and iso-octyl radicals, such as the 2,2,4-trimethylpentyl radical; Nonyl radicals, such as the n-nonyl radical; Decyl radicals, such as the n-decyl radical; Dodecyl radicals, such as the n-dodecyl radical; Octadecyl radicals, such as the n-octadecyl radical; Cycloalkyl radicals such as the cyclopentyl, cyclohexyl, cycloheptyl and methylcyclohexyl radicals; Alkenyl radicals, such as the vinyl, 1-propenyl and the 2-propenyl radical; Aryl radicals, such as the pheny
- a is a number equal to 1, 2, 3, 4, 5 or 6,
- b is a number equal to 1, 2 or 3,
- c is a number equal to 1, 2, 3, 4 or 5
- d is a number equal to 0 or 1
- e is a number equal to 1, 2, 3, 4, 5 or 6,
- f is a number equal to 1, 2 or 3,
- g is a number equal to 1, 2, 3 or 4,
- h is a number equal to 0 or 1
- R 6 is a hydrocarbon radical having 1-6 C atoms, in particular ethyl or methyl and
- R 7 is a hydrocarbon radical having 1-6 C atoms, in particular ethyl or methyl.
- radicals R 1 , R 4 are independently of each other preferably selected from alkoxyalkyl radicals or alkylaminoalkyl radicals.
- the radicals R 1 , R 4 independently of one another are an alkoxyalkyl radical, in particular Cl-3-alkoxyCl-3-alkyl radical.
- the hydrocarbon radicals R 2 , R 3 may be alkyl radicals, such as the methyl, ethyl, n-propyl, iso-propyl, 1-n-butyl, 2-n-butyl, iso-butyl, tert. Butyl, n-pentyl, iso-pentyl, neo-pentyl, tert.
- -Pentyl radical Hexyl radicals, such as the n-hexyl radical; Heptyl radicals, such as the n-heptyl radical; Octyl radicals, such as the n-octyl residual and iso-octyl radicals, such as the 2,2,4-trimethylpentyl radical; Nonyl radicals, such as the n-nonyl radical; Decyl radicals, such as the n-decyl radical; Dodecyl radicals, such as the n-dodecyl radical; Octadecyl radicals, such as the n-octadecyl radical; Cycloalkyl radicals such as the cyclopentyl, cyclohexyl, cycloheptyl and methylcyclohexyl radicals; Alkenyl radicals, such as the vinyl, 1-propenyl and the 2-propenyl radical; Aryl radicals, such as the pheny
- R 2 , R 3 is the methyl, ethyl, iso and n-propyl, iso and n-butyl, phenyl or vinyl radical.
- R 2 , R 3 is particularly preferably the methyl or ethyl radical.
- n preferably has the value 1.
- m preferably has the value 0 or 1.
- Another object of the invention is a method for
- Condensation in the presence of further reactive compounds of the general formula 7 can take place to a product of the general formula (1), or by b) hydrolytic condensation of (haloorganyl) silicium compounds of the general formula (5), wherein the hydrolytic condensation can take place in the presence of further reactive compounds of the general formula 7 to a product the general formula (8) and reaction with amines of the general formula (4),
- R ' is an acyloxy radical and an alkoxy radical having in each case 1-10 C atoms
- R '' is a radical of general formula 10
- X, Y are independently chlorine, bromine or iodine and
- p is an integer equal to or greater than 3
- R 1 , R 2 , R 3 , R 4 , n and m have the abovementioned meanings.
- the amine of general formula (4) is preferably in excess, i. H. in molar ratios based on the proportion of the reactive groups X and Y from 1.1 to 1 to 100 to 1, preferably from 1.5 to 1 to 50 to 1, particularly preferably from 2 to 1 to 20 to 1, in particular from 3 used to 1 to 10 to 1.
- the base (B) is preferably in molar ratios based on the proportion of the reactive groups X and Y of 0.5 to 1 to 10 to 1, preferably from 0.7 to 1 to 5 to 1, more preferably from 0.8 to 1 to 2 to 1, in particular from 0.9 to 1 to 1.0 to 1 used.
- step al) and a2) can take place successively or simultaneously. It is also possible to carry out a time-delayed procedure in which the start of step a2), ie the addition of the base (B), is begun after the start but before the end of step al). If a base (B) which has free NH or NH 2 groups is used in the processes according to the invention, step a2), ie the addition of the oligoamine, is preferably carried out after the reaction in step al). Preference is given to using bases (B) which, in process step a2), form salts which, even at temperatures ⁇ 150.degree. C., form particularly preferably ⁇ 100.degree. C. or ⁇ 90.degree. C. liquids. Step al) of the method according to the invention is preferably carried out at temperatures of 50 to 250 ° C. To one
- temperatures of 50 to 220 ° C, in particular from 80 ° C to 150 ° C have proven to be particularly advantageous.
- the steps a2) and a3) of the processes according to the invention are carried out at a temperature at which the halide of the base (B) is present as a separate liquid phase, preferably at temperatures of 0-250 ° C., preferably at temperatures of 20 to 150 ° C. and especially preferably carried out at temperatures of 50 to 100 ° C.
- the pressure in the reaction steps al), a2) and a3) is preferably 0.05 to 2 MPa (abs.), More preferably 0.08 to 1.5 MPa (abs.), In particular 0.09 to 1 MPa (abs .).
- All reaction steps are preferably carried out under protective gas, e.g. Nitrogen and argon carried out.
- protective gas e.g. Nitrogen and argon carried out.
- the processes according to the invention can also have one or more of the following additional process steps:
- step al) if the amine of the general formula (4) in step al) was used in excess, this excess can be completely or partially separated before the addition of the base (B) in step a2).
- the separation is preferably carried out by distillation. This measure is preferably used to reduce the solubility of the respective salts or in the organic phase.
- nonpolar solvents (L) adding one or more nonpolar solvents (L) to the product-containing phase.
- the additional solvent (L) can be added before, during or after the process steps a1), a2), a3) and a4). This measure serves to reduce the solubility of the respective salts in the organic phase.
- the nonpolar solvent is added after process step a3), the salts precipitated in this step are separated in an additional separation step, eg filtration.
- the amounts of salt to be separated off are extremely small compared with the original amount of salt in step a3), and the separation is correspondingly simple.
- the addition of the nonpolar solvent is carried out before or during step a3), the respective salts from the product phase are forced into the liquid phase, which essentially consists of the halide of the base (B), and are separated together therewith.
- halides of the base (B) remain in the organic phase during the phase separation in step a3), these are preferably removed by distillation. The same applies to the solvent (L) additionally added if necessary in step a5).
- a recovery or recycling of the amine of general formula (4) used in step a) optionally in excess and of the amine released in step a2) takes place. If the amine of general formula (4) wholly or at least in part can not be obtained by a simple distillation in sufficient cleanliness, the interfering products, by-products or even residues of in
- Step a2) added base (B) are separated by one or more further purification steps.
- a recovery of the base (B) used in step a2) is preferably carried out by salification of the
- the respective bases in bulk or in aqueous or non-aqueous solution or suspension
- Ethylenediamine used as the base (B) this separation by distillation is preferably carried out at such high pressure that ethylenediamine and water no longer form an azeotrope.
- the base (B) is a compound, e.g., an amine which is itself reactive with the silane of the general formula (5)
- the amine of the general formulas (4) is preferably purified by the said process steps so far that the content of the base (B) in the amines of the general formulas (4) is less than 3%, preferably less than 1% and especially less than 0.5%.
- the amine of the general formula (4) is used in excess, wherein the excess amine is removed by a step a4) by distillation substantially or at least in parts.
- the base (B) is added (step a2)) and the salt phase separated (step a3)).
- the amine of general formulas (2) liberated in step a2) is removed by distillation.
- the distillate of the amine of the general formula (4) is preferably obtained with such high purity that it is used directly again without further purification.
- the process step a) both batchwise, eg in stirred tanks, as well as be carried out continuously. The latter z. B.
- Contacting the product of general formula 6 with water in the second process step (a6) can be carried out by any means known to those skilled in the art. This can be done either discontinuously or continuously.
- the product of general formula 6 can be stirred or shaken together with water to ensure a particularly good distribution of the components of such a mixture.
- a particularly preferred embodiment of the process according to the invention is the continuous contacting by passing the product of the general formula 6 through a reaction tube in which optionally also static mixers can be present.
- the product of the general formula 6 is brought into contact with water in a loop reactor, it being possible where appropriate for the mixing to be improved by static mixers.
- the ratio of the product of general formula 6 to water. can be targeted by the expert with regard to the desired Properties of the final product can be selected. In this case, the molar amount of water must be sufficient in order to reactivate all hydrolyzable groups R 'present in the product of the general formula 6.
- the second step (a6) of the process according to the invention can also be carried out in the presence of further hydrolysis-labile compounds of the general formula 7.
- the second step (a6) of the process according to the invention can also be carried out in the presence of a solvent inert to the reactants.
- solvents are at 20 ° C (1013 mbar) liquid hydrocarbons and halogenated hydrocarbons, such as benzene, toluene, xylene, methylene chloride, petroleum ether.
- the second step (a6) of the process according to the invention is preferably carried out at temperatures of 20 to 200 ° C., in particular 20 to 100 ° C. More preferably, the reaction temperature is in a range of 40-80 ° C.
- the residence time T 'in the reaction vessel can be selected from a range of 1 second ⁇ T' ⁇ 24 h.
- the residence time T ' is in a range of 60 minutes ⁇ T' ⁇ 600 minutes, more preferably in a range of 120 minutes -5 T '-5 480 minutes.
- the hydrolyzable group R "which is released during the hydrolysis can be separated off either directly in gaseous form or dissolved in an excess of water in its protonated form HR.”
- the separation can be carried out by any type known to the person skilled in the art.
- reaction may be carried out by any means known to those skilled in the art. This can be done both discontinuously and continuously.
- the ratio of the product of the general formula 9 with linear or cyclic siloxanes can be selected by the person skilled in the art specifically with regard to the desired properties of the end product.
- the reaction may also be in the presence of a solvent inert to the reactants be performed.
- solvents are at 20 ° C (1013 mbar) liquid hydrocarbons and halogenated hydrocarbons, such as benzene, toluene, xylene, methylene chloride, petroleum ether.
- no additional solvent is used.
- this step is carried out at temperatures of 20 to 200 ° C, especially at 20 - 150 ° C. More preferably, the reaction temperature is in a range of 40-120 ° C.
- the residence time T 'in the reaction vessel can be selected from a range of 1 second ⁇ T' ⁇ 24 h.
- the residence time T ' is in a range of 60 minutes ⁇ T' ⁇ 600 minutes, more preferably in a range of 120 minutes ⁇ T ' ⁇ 480 minutes.
- Suitable catalyst K for the equilibration is any suitable compound known to the person skilled in the art.
- equilibration catalysts examples include alkali metal hydroxides, in particular potassium, rubidium and cesium hydroxide, alkali metal alcoholates, quaternary ammonium hydroxides, such as tetramethylammonium hydroxide (TMAH) or its pentahydrate, tetrabutylammonium hydroxide, benzyltrimethylammonium hydroxide, benzyltrimethylammonium hydroxide.
- TMAH tetramethylammonium hydroxide
- TMAH tetramethylammonium hydroxide
- benzyltrimethylammonium hydroxide benzyltrimethylammonium hydroxide.
- Ethylammoniunihydroxid also mixtures thereof, as aqueous or alcoholic solution, Benzyltrimethylammoniumbutylat, ß- hydroxyethyltrimethylammonium 2-ethylhexanoat, quaternary phosphonium hydroxides, such as tetramethylphosphonium hydroxide, tetra- ethylphosphonium hydroxide, tetra-n-butylphosphonium hydroxide and tri-n-butyl-3- [tris - (trimethylsiloxy) silyl] -n-propyl-phosphonium hydroxide, their mixtures, and their silanolates and siloxanolates.
- quaternary phosphonium hydroxides such as tetramethylphosphonium hydroxide, tetra- ethylphosphonium hydroxide, tetra-n-butylphosphonium hydroxide and tri-n-butyl-3- [tri
- the alkali metal hydroxides are particularly preferably NaOH, KOH or quaternary ammonium hydroxides, such as tetramethylammonium hydride or benzyltrimethylammonium hydroxide.
- the equilibration step is preferably carried out with the greatest possible exclusion of atmospheric moisture and preferably in an inert gas atmosphere, such as e.g. Nitrogen and noble gases, preferably nitrogen or argon performed.
- an inert gas atmosphere such as e.g. Nitrogen and noble gases, preferably nitrogen or argon performed.
- the reaction mixture obtained can be worked up by any desired methods known hitherto.
- the calibration catalyst K is deactivated and / or
- the equilibration catalyst K is deactivated after the end of the equilibration.
- the reaction mixture is preferably treated thermally, more preferably at least one or more hours heated to 150 ° C.
- the pressure is first lowered, preferably to 500 to 800 mbar, then on is lowered, preferably to 0.1 to 10 mbar, wherein the cleavage products of the catalysts and further volatile compounds are distilled off. Subsequently, the thus obtained, turbid reaction mixture is filtered, the filtration
- Catalyst is after equilibration b2) the reaction mixture with inorganic or organic acids or neutralized with CO2 and the salts are then filtered, the filtration can optionally be carried out under an elevated pressure of preferably 2 to 5 bar, to obtain a clear, colorless liquid.
- amino-siloxane compositions and processes for their preparation shown here have the advantage that the resulting costs can be minimized by economies of scale. Further, the amino-siloxane compositions have relatively low viscosity, high thermal stability, and can be readily provided by the synthetic methods disclosed herein.
- Formulas is the silicon atom tetravalent.
- Salt phase (ethylenediamine hydrochloride) at 90 ° C in one
- Salt phase (ethylenediamine hydrochloride) at 90 ° C in one
- Octamethylcyclotetrasiloxane presented at 25 ° C. To this mixture was added 0.1 g (0.6 mmol) of tetramethylammonium hydroxide
- Viscosity (DIN 51562-1) 69 mm2 / s
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Abstract
L'invention concerne des aminosiloxanes (A) de formule générale 1 R1-NH- (CH2)n-R2
2Si-O-[SiR3
2-O]m-SiR2
2-(CH2)n-NH-R4 (1), dans laquelle R1, R4 représentent, indépendamment l'un de l'autre, un radical hydrocarboné substitué ou non substitué, saturé ou insaturé, ramifié ou non ramifié, linéaire ou cyclique, aliphatique ou aromatique, comprenant 1-20 atomes de carbone, un ou plusieurs motifs de méthylène, qui ne sont pas adjacents à un autre hétéroatome choisi dans le groupe contenant N, O, S et P, peuvent être remplacés par un hétéroatome choisi dans le groupe contenant N, O, S et P, R2, R3 représentent, indépendamment l'un de l'autre, un radical hydrocarboné substitué ou non substitué, saturé ou insaturé, ramifié ou non ramifié, linéaire ou cyclique, aliphatique ou aromatique comprenant 1-20 atomes de carbone, n représente un nombre valant 1 ou 2 et m représente un nombre identique ou supérieur à 0 ; un procédé pour la préparation des aminosiloxanes (A) et leur utilisation pour l'apprêt de textiles, pour des formulations cosmétiques, le traitement de surface, pour la préparation de copolymères séquencés ou pour la fixation et l'élimination de dioxyde de carbone de gaz d'échappement.
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Citations (2)
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CN103215815A (zh) * | 2013-03-20 | 2013-07-24 | 苏州经贸职业技术学院 | 一种羊毛改性工艺 |
WO2015011258A1 (fr) * | 2013-07-26 | 2015-01-29 | L'oreal | Procédé de traitement capillaire avec au moins un polymère de silicone fonctionnalisé par au mois une unité alcoxysilane et au moins un alcoxysilane spécifique |
-
2016
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CN103215815A (zh) * | 2013-03-20 | 2013-07-24 | 苏州经贸职业技术学院 | 一种羊毛改性工艺 |
WO2015011258A1 (fr) * | 2013-07-26 | 2015-01-29 | L'oreal | Procédé de traitement capillaire avec au moins un polymère de silicone fonctionnalisé par au mois une unité alcoxysilane et au moins un alcoxysilane spécifique |
Non-Patent Citations (4)
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DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; 1965, ANDRIANOV, K. A. ET AL: "Tridimensional condensation of silicon-containing diamines with tetrafunctional ester acids", XP002771394, retrieved from STN Database accession no. 1965:481032 * |
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; 1974, SHELUDYAKOV, V. D. ET AL: "Properties of 2,5-disilapiperazine derivatives", XP002771393, retrieved from STN Database accession no. 1974:505614 * |
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; 1975, ANDRIANOV, K. A. ET AL: "Organosilicon oligomers containing symmetric triazine rings", XP002771392, retrieved from STN Database accession no. 1975:531966 * |
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