DD144411A5 - Verfahren zur herstellung von 1,3,5-triazacycloheptan-2,4-dionderivaten - Google Patents

Verfahren zur herstellung von 1,3,5-triazacycloheptan-2,4-dionderivaten Download PDF

Info

Publication number: DD144411A5
Authority: DD; German Democratic Republic
Prior art keywords: formula; carbon atoms; compound; hydrogen; compounds
Prior art date: 1978-06-20

Application number

DD79213781A

Other languages

German (de)

English (en)

Inventor

Guiseppe Cantatore

Paolo It Cassandrini

Original Assignee

Chimosa Chimica Organica Spa

Priority date (The priority date 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 date listed.)

1978-06-20

Filing date

1979-06-20

Publication date

1980-10-15

1979-06-20 Application filed by Chimosa Chimica Organica Spa filed Critical Chimosa Chimica Organica Spa

1980-10-15 Publication of DD144411A5 publication Critical patent/DD144411A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 14
238000002360 preparation method Methods 0.000 title claims abstract description 5
CVLAODKSTMIFRC-UHFFFAOYSA-N 1,3,5-triazepane-2,4-dione Chemical class O=C1NCCNC(=O)N1 CVLAODKSTMIFRC-UHFFFAOYSA-N 0.000 title abstract description 4
150000001875 compounds Chemical class 0.000 claims abstract description 58
229910052739 hydrogen Inorganic materials 0.000 claims description 23
239000001257 hydrogen Substances 0.000 claims description 23
125000004432 carbon atom Chemical group C* 0.000 claims description 22
125000000217 alkyl group Chemical group 0.000 claims description 13
150000002431 hydrogen Chemical class 0.000 claims description 12
229910052757 nitrogen Inorganic materials 0.000 claims description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 9
OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 claims description 9
239000004202 carbamide Substances 0.000 claims description 9
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
238000006243 chemical reaction Methods 0.000 claims description 5
125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
125000003342 alkenyl group Chemical group 0.000 claims description 4
125000006289 hydroxybenzyl group Chemical group 0.000 claims description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 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
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 3
125000003118 aryl group Chemical group 0.000 claims description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
229910052794 bromium Inorganic materials 0.000 claims description 3
239000000460 chlorine Substances 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 2
125000000304 alkynyl group Chemical group 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 claims description 2
235000019253 formic acid Nutrition 0.000 claims description 2
125000000623 heterocyclic group Chemical group 0.000 claims description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims 2
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 2
125000002947 alkylene group Chemical group 0.000 claims 1
125000003710 aryl alkyl group Chemical group 0.000 claims 1
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical class O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims 1
239000000126 substance Substances 0.000 claims 1
239000003381 stabilizer Substances 0.000 abstract description 12
229920001059 synthetic polymer Polymers 0.000 abstract description 7
230000003647 oxidation Effects 0.000 abstract description 3
238000007254 oxidation reaction Methods 0.000 abstract description 3
-1 n-octyl Chemical group 0.000 description 30
QUAMTGJKVDWJEQ-UHFFFAOYSA-N octabenzone Chemical compound OC1=CC(OCCCCCCCC)=CC=C1C(=O)C1=CC=CC=C1 QUAMTGJKVDWJEQ-UHFFFAOYSA-N 0.000 description 18
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
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239000004611 light stabiliser Substances 0.000 description 9
229920000642 polymer Polymers 0.000 description 9
239000003963 antioxidant agent Substances 0.000 description 7
239000000047 product Substances 0.000 description 7
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 5
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125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
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150000003254 radicals Chemical class 0.000 description 4
239000002904 solvent Substances 0.000 description 4
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239000008096 xylene Substances 0.000 description 4
NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000000654 additive Substances 0.000 description 3
230000003078 antioxidant effect Effects 0.000 description 3
CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 3
239000008116 calcium stearate Substances 0.000 description 3
235000013539 calcium stearate Nutrition 0.000 description 3
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
238000010992 reflux Methods 0.000 description 3
KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 2
JKXHAXGBTMSGDP-UHFFFAOYSA-N 1,5-bis(2,2,6,6-tetramethylpiperidin-4-yl)-1,3,5-triazepane-2,4-dione Chemical compound C1C(C)(C)NC(C)(C)CC1N1C(=O)NC(=O)N(C2CC(C)(C)NC(C)(C)C2)CC1 JKXHAXGBTMSGDP-UHFFFAOYSA-N 0.000 description 2
125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 description 2
125000006491 4-t-butyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])*)C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
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AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
239000004743 Polypropylene Substances 0.000 description 2
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
239000006096 absorbing agent Substances 0.000 description 2
229910052793 cadmium Inorganic materials 0.000 description 2
BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 2
229910052791 calcium Inorganic materials 0.000 description 2
239000011575 calcium Substances 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
238000001816 cooling Methods 0.000 description 2
229920001577 copolymer Polymers 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
NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
229920001903 high density polyethylene Polymers 0.000 description 2
239000004700 high-density polyethylene Substances 0.000 description 2
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
229920001684 low density polyethylene Polymers 0.000 description 2
239000004702 low-density polyethylene Substances 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
238000000465 moulding Methods 0.000 description 2
125000004108 n-butyl group Chemical group [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
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
229910052759 nickel Inorganic materials 0.000 description 2
125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
ZQBAKBUEJOMQEX-UHFFFAOYSA-N phenyl salicylate Chemical compound OC1=CC=CC=C1C(=O)OC1=CC=CC=C1 ZQBAKBUEJOMQEX-UHFFFAOYSA-N 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
229920001155 polypropylene Polymers 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000000843 powder Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
229910052725 zinc Inorganic materials 0.000 description 2
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ARVUDIQYNJVQIW-UHFFFAOYSA-N (4-dodecoxy-2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC(OCCCCCCCCCCCC)=CC=C1C(=O)C1=CC=CC=C1 ARVUDIQYNJVQIW-UHFFFAOYSA-N 0.000 description 1
ZBBLRPRYYSJUCZ-GRHBHMESSA-L (z)-but-2-enedioate;dibutyltin(2+) Chemical compound [O-]C(=O)\C=C/C([O-])=O.CCCC[Sn+2]CCCC ZBBLRPRYYSJUCZ-GRHBHMESSA-L 0.000 description 1
FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 description 1
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MQQKTNDBASEZSD-UHFFFAOYSA-N 1-(octadecyldisulfanyl)octadecane Chemical compound CCCCCCCCCCCCCCCCCCSSCCCCCCCCCCCCCCCCCC MQQKTNDBASEZSD-UHFFFAOYSA-N 0.000 description 1
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UPYPTOCXMIWHSG-UHFFFAOYSA-N 1-dodecylsulfanyldodecane Chemical compound CCCCCCCCCCCCSCCCCCCCCCCCC UPYPTOCXMIWHSG-UHFFFAOYSA-N 0.000 description 1
IHWDIGHWDQPQMQ-UHFFFAOYSA-N 1-octadecylsulfanyloctadecane Chemical compound CCCCCCCCCCCCCCCCCCSCCCCCCCCCCCCCCCCCC IHWDIGHWDQPQMQ-UHFFFAOYSA-N 0.000 description 1
AZELNFRNNQTCKD-UHFFFAOYSA-N 2,6-ditert-butyl-4-(isocyanatomethyl)phenol Chemical compound CC(C)(C)C1=CC(CN=C=O)=CC(C(C)(C)C)=C1O AZELNFRNNQTCKD-UHFFFAOYSA-N 0.000 description 1
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ZMWRRFHBXARRRT-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4,6-bis(2-methylbutan-2-yl)phenol Chemical compound CCC(C)(C)C1=CC(C(C)(C)CC)=CC(N2N=C3C=CC=CC3=N2)=C1O ZMWRRFHBXARRRT-UHFFFAOYSA-N 0.000 description 1
POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
JDJYCULXEUECID-UHFFFAOYSA-N 2-dodecyl-2-methyltetradecanethioic s-acid Chemical compound CCCCCCCCCCCCC(C)(C(S)=O)CCCCCCCCCCCC JDJYCULXEUECID-UHFFFAOYSA-N 0.000 description 1
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
229940093475 2-ethoxyethanol Drugs 0.000 description 1
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
YOHAKKRKLXGANL-UHFFFAOYSA-N 2-methyl-2-octadecylicosanethioic s-acid Chemical compound CCCCCCCCCCCCCCCCCCC(C)(C(S)=O)CCCCCCCCCCCCCCCCCC YOHAKKRKLXGANL-UHFFFAOYSA-N 0.000 description 1
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
HXIQYSLFEXIOAV-UHFFFAOYSA-N 2-tert-butyl-4-(5-tert-butyl-4-hydroxy-2-methylphenyl)sulfanyl-5-methylphenol Chemical compound CC1=CC(O)=C(C(C)(C)C)C=C1SC1=CC(C(C)(C)C)=C(O)C=C1C HXIQYSLFEXIOAV-UHFFFAOYSA-N 0.000 description 1
ODJQKYXPKWQWNK-UHFFFAOYSA-N 3,3'-Thiobispropanoic acid Chemical compound OC(=O)CCSCCC(O)=O ODJQKYXPKWQWNK-UHFFFAOYSA-N 0.000 description 1
NMAGCVWUISAHAP-UHFFFAOYSA-N 3,5-ditert-butyl-2-(2,4-ditert-butylphenyl)-4-hydroxybenzoic acid Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1C1=C(C(O)=O)C=C(C(C)(C)C)C(O)=C1C(C)(C)C NMAGCVWUISAHAP-UHFFFAOYSA-N 0.000 description 1
CFDIRMCJYJMOKR-UHFFFAOYSA-N 3-butyl-1,5-bis(2,2,6,6-tetramethylpiperidin-4-yl)-1,3,5-triazepane-2,4-dione Chemical compound O=C1N(CCCC)C(=O)N(C2CC(C)(C)NC(C)(C)C2)CCN1C1CC(C)(C)NC(C)(C)C1 CFDIRMCJYJMOKR-UHFFFAOYSA-N 0.000 description 1
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MVMDLSOLQZOZSF-UHFFFAOYSA-N CCCCN1C(CC(CC1(C)C)N2CCNC(=O)NC2=O)(C)C Chemical compound CCCCN1C(CC(CC1(C)C)N2CCNC(=O)NC2=O)(C)C MVMDLSOLQZOZSF-UHFFFAOYSA-N 0.000 description 1
PJGDNMJQXGPFSC-UHFFFAOYSA-N CCCN1C(CC(CC1(C)C)N2CCNC(=O)NC2=O)(C)C Chemical compound CCCN1C(CC(CC1(C)C)N2CCNC(=O)NC2=O)(C)C PJGDNMJQXGPFSC-UHFFFAOYSA-N 0.000 description 1
QFUWIZMVNQSGQH-UHFFFAOYSA-N CCN1C(=O)NCCN(C1=O)C2CC(NC(C2)(C)C)(C)C Chemical compound CCN1C(=O)NCCN(C1=O)C2CC(NC(C2)(C)C)(C)C QFUWIZMVNQSGQH-UHFFFAOYSA-N 0.000 description 1
JMJZPZNNBONDSQ-UHFFFAOYSA-N CCN1C(CC(CC1(C)C)N2CCNC(=O)NC2=O)(C)C Chemical compound CCN1C(CC(CC1(C)C)N2CCNC(=O)NC2=O)(C)C JMJZPZNNBONDSQ-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
238000006824 Eschweiler-Clarke methylation reaction Methods 0.000 description 1
229930040373 Paraformaldehyde Natural products 0.000 description 1
JKIJEFPNVSHHEI-UHFFFAOYSA-N Phenol, 2,4-bis(1,1-dimethylethyl)-, phosphite (3:1) Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP(OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC1=CC=C(C(C)(C)C)C=C1C(C)(C)C JKIJEFPNVSHHEI-UHFFFAOYSA-N 0.000 description 1
239000004952 Polyamide Substances 0.000 description 1
239000005062 Polybutadiene Substances 0.000 description 1
239000004793 Polystyrene Substances 0.000 description 1
239000003490 Thiodipropionic acid Substances 0.000 description 1
239000007983 Tris buffer Substances 0.000 description 1
BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
BLXLSQIOCCHAHJ-UHFFFAOYSA-N [2,3,4-tri(nonyl)phenyl] dihydrogen phosphite Chemical compound CCCCCCCCCC1=CC=C(OP(O)O)C(CCCCCCCCC)=C1CCCCCCCCC BLXLSQIOCCHAHJ-UHFFFAOYSA-N 0.000 description 1
UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 description 1
229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 1
239000004676 acrylonitrile butadiene styrene Substances 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
229920000180 alkyd Polymers 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
239000002216 antistatic agent Substances 0.000 description 1
238000010533 azeotropic distillation Methods 0.000 description 1
229910052788 barium Inorganic materials 0.000 description 1
DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
RYTAZQLUNUCPFQ-UHFFFAOYSA-L barium(2+);dodecanoate Chemical class [Ba+2].CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O RYTAZQLUNUCPFQ-UHFFFAOYSA-L 0.000 description 1
JBIROUFYLSSYDX-UHFFFAOYSA-M benzododecinium chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 JBIROUFYLSSYDX-UHFFFAOYSA-M 0.000 description 1
PZGVVCOOWYSSGB-UHFFFAOYSA-L but-2-enedioate;dioctyltin(2+) Chemical compound CCCCCCCC[Sn]1(CCCCCCCC)OC(=O)C=CC(=O)O1 PZGVVCOOWYSSGB-UHFFFAOYSA-L 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
238000005266 casting Methods 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
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 1
150000004985 diamines Chemical class 0.000 description 1
229940117389 dichlorobenzene Drugs 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
150000002019 disulfides Chemical class 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
239000003822 epoxy resin Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
239000000835 fiber Substances 0.000 description 1
239000000945 filler Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000012467 final product Substances 0.000 description 1
239000003063 flame retardant Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
150000002367 halogens Chemical group 0.000 description 1
LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
230000000937 inactivator Effects 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
239000001023 inorganic pigment Substances 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
239000004922 lacquer Substances 0.000 description 1
239000011133 lead Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
238000002156 mixing Methods 0.000 description 1
125000002757 morpholinyl group Chemical group 0.000 description 1
LZZWTDIRGVWWJL-UHFFFAOYSA-N n'-(2,2,6,6-tetramethylpiperidin-4-yl)ethane-1,2-diamine Chemical compound CC1(C)CC(NCCN)CC(C)(C)N1 LZZWTDIRGVWWJL-UHFFFAOYSA-N 0.000 description 1
JMWUYEFBFUCSAK-UHFFFAOYSA-L nickel(2+);octadecanoate Chemical class [Ni+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O JMWUYEFBFUCSAK-UHFFFAOYSA-L 0.000 description 1
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000012860 organic pigment Substances 0.000 description 1
238000006053 organic reaction Methods 0.000 description 1
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
XDZUKIGDGNQFBD-UHFFFAOYSA-N phenol;4-(2,4,4-trimethylpentan-2-yl)phenol Chemical compound OC1=CC=CC=C1.CC(C)(C)CC(C)(C)C1=CC=C(O)C=C1 XDZUKIGDGNQFBD-UHFFFAOYSA-N 0.000 description 1
239000002530 phenolic antioxidant Substances 0.000 description 1
229960000969 phenyl salicylate Drugs 0.000 description 1
229940099800 pigment red 48 Drugs 0.000 description 1
125000004193 piperazinyl group Chemical group 0.000 description 1
125000003386 piperidinyl group Chemical group 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
229920000058 polyacrylate Polymers 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
229920002857 polybutadiene Polymers 0.000 description 1
229920000515 polycarbonate Polymers 0.000 description 1
239000004417 polycarbonate Substances 0.000 description 1
229920000647 polyepoxide Polymers 0.000 description 1
229920001195 polyisoprene Polymers 0.000 description 1
229920006324 polyoxymethylene Polymers 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
229920002635 polyurethane Polymers 0.000 description 1
239000004814 polyurethane Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
238000003825 pressing Methods 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000005932 reductive alkylation reaction Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
238000013112 stability test Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
238000012360 testing method Methods 0.000 description 1
235000019303 thiodipropionic acid Nutrition 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
IVIIAEVMQHEPAY-UHFFFAOYSA-N tridodecyl phosphite Chemical compound CCCCCCCCCCCCOP(OCCCCCCCCCCCC)OCCCCCCCCCCCC IVIIAEVMQHEPAY-UHFFFAOYSA-N 0.000 description 1
125000005065 undecenyl group Chemical group C(=CCCCCCCCCC)* 0.000 description 1
229920006305 unsaturated polyester Polymers 0.000 description 1

Classifications

- 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
- C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Compositions Of Macromolecular Compounds (AREA)
Hydrogenated Pyridines (AREA)
Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Plural Heterocyclic Compounds (AREA)

DD79213781A 1978-06-20 1979-06-20 Verfahren zur herstellung von 1,3,5-triazacycloheptan-2,4-dionderivaten DD144411A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
IT24744/78A IT1096590B (it)	1978-06-20	1978-06-20	Derivati dell'1,3,5-triazacicloeptan-2,4-dione,processo per la loro preparazione e loro impiego come stabilizzanti per polimeri

Publications (1)

Publication Number	Publication Date
DD144411A5 true DD144411A5 (de)	1980-10-15

Family

ID=11214601

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD79213781A DD144411A5 (de)	1978-06-20	1979-06-20	Verfahren zur herstellung von 1,3,5-triazacycloheptan-2,4-dionderivaten

Country Status (16)

Country	Link
US (1)	US4238388A (fr)
JP (1)	JPS557273A (fr)
AU (1)	AU4820679A (fr)
BE (1)	BE877116A (fr)
BR (1)	BR7903890A (fr)
CS (1)	CS212235B2 (fr)
DD (1)	DD144411A5 (fr)
DE (1)	DE2924894A1 (fr)
DK (1)	DK255279A (fr)
ES (1)	ES481700A1 (fr)
FR (1)	FR2429215A1 (fr)
GB (1)	GB2024217A (fr)
IT (1)	IT1096590B (fr)
LU (1)	LU81406A1 (fr)
NL (1)	NL7904838A (fr)
ZA (1)	ZA793077B (fr)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IT7921841A0 (it) *	1979-04-13	1979-04-13	Chimosa Chimica Organica Spa	Nuovi composti piperidinici, processo per la loro preparazione e loro impiego come stabilizzanti per polimeri sintetici.
JPS573842A (en) *	1980-06-10	1982-01-09	Sumitomo Chem Co Ltd	Stabilized polyolefin composition
IT1195277B (it) *	1981-10-02	1988-10-12	Chimosa Chimica Organica Spa	Piperidil derivati di composti triazinici macrociclici,aventi attivita' stabilizzante per i polimeri e processi per la loro preparazione
US4631339A (en) *	1983-04-18	1986-12-23	Eli Lilly And Company	1,3,5-triazepinones
JPS6227430A (ja) *	1985-07-30	1987-02-05	Ube Ind Ltd	耐候性の優れたポリアミドの製法
DE3643890A1 (de) *	1986-12-22	1988-06-30	Basf Ag	Neue polyalkylpiperidinderivate mit alkylenbruecken, ihre verwendung als stabilisator und zwischenprodukte
IT1205119B (it) *	1987-06-02	1989-03-15	Ciba Geigy Spa	Composti piperidinici biciclici utilizzabili come stabilizzanti per polimeri sintetici
JP2007039443A (ja) *	2005-07-01	2007-02-15	Mitsui Chemicals Inc	１，３−ジアルキル−２−イミダゾリジノンおよび１，５−ジアルキル−［１，３，５］トリアゼパン−２，４−ジオンの製造方法

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3878199A (en) *	1973-07-23	1975-04-15	Dow Chemical Co	Hydroxyalkyl derivatives of 1,3,5-triazacycloheptane-2,4-diones

1978
- 1978-06-20 IT IT24744/78A patent/IT1096590B/it active
1979
- 1979-06-19 DK DK255279A patent/DK255279A/da unknown
- 1979-06-20 DD DD79213781A patent/DD144411A5/de unknown
- 1979-06-20 JP JP7694179A patent/JPS557273A/ja active Pending
- 1979-06-20 ES ES481700A patent/ES481700A1/es not_active Expired
- 1979-06-20 DE DE19792924894 patent/DE2924894A1/de not_active Withdrawn
- 1979-06-20 US US06/050,207 patent/US4238388A/en not_active Expired - Lifetime
- 1979-06-20 FR FR7915777A patent/FR2429215A1/fr not_active Withdrawn
- 1979-06-20 LU LU81406A patent/LU81406A1/fr unknown
- 1979-06-20 CS CS794246A patent/CS212235B2/cs unknown
- 1979-06-20 AU AU48206/79A patent/AU4820679A/en not_active Abandoned
- 1979-06-20 NL NL7904838A patent/NL7904838A/xx not_active Application Discontinuation
- 1979-06-20 BR BR7903890A patent/BR7903890A/pt unknown
- 1979-06-20 GB GB7921539A patent/GB2024217A/en not_active Withdrawn
- 1979-06-20 ZA ZA793077A patent/ZA793077B/xx unknown
- 1979-06-20 BE BE0/195853A patent/BE877116A/fr unknown

Also Published As

Publication number	Publication date
CS212235B2 (en)	1982-03-26
FR2429215A1 (fr)	1980-01-18
LU81406A1 (fr)	1979-09-12
IT1096590B (it)	1985-08-26
DK255279A (da)	1979-12-21
AU4820679A (en)	1980-01-03
US4238388A (en)	1980-12-09
IT7824744A0 (it)	1978-06-20
BE877116A (fr)	1979-10-15
JPS557273A (en)	1980-01-19
BR7903890A (pt)	1980-03-04
GB2024217A (en)	1980-01-09
NL7904838A (nl)	1979-12-27
ZA793077B (en)	1980-07-30
ES481700A1 (es)	1980-03-01
DE2924894A1 (de)	1980-01-10

Publication	Publication Date	Title
DE2647452C2 (fr)	1991-08-08
EP0031304B1 (fr)	1984-06-13	Dérivés de pipéridine comme stabilisants de polymères synthétiques
DE2319816C2 (de)	1982-07-29	Piperidin-Derivate, Verfahren zu deren Herstellung und deren Verwendung
DE2636144B2 (de)	1979-10-31	Polytriazinverbindungen
DE3236070C2 (fr)	1992-05-14
DE2258752A1 (de)	1973-06-07	Neue piperidin-derivate
DE2930397C2 (fr)	1988-05-26
DE2654058A1 (de)	1977-06-23	Hydroxybenzylmalonsaeurederivate
JPS6038432A (ja)	1985-02-28	ピペリジン基及びトリアジン基を含有する高分子化合物及び該化合物を含有する合成高分子重合体用安定剤
DE2926897A1 (de)	1980-01-24	Neue stabilisatoren
DE2128757A1 (de)	1971-12-23	Piperidinderivate und deren Verwendung als Stabilisatoren
EP0002261A1 (fr)	1979-06-13	Esters d'acides 2,2'-biphénylène phosphoneux alcoylés et compositions stabilisées les contenant
EP0019578B1 (fr)	1983-03-30	Dérivés de la pipéridine, procédé pour leur préparation et compositions polymères les contenant
IL44629A (en)	1977-02-28	Stabilization of synthetic polymers by means of certain 1-substituted piperidine derivatives
DD144411A5 (de)	1980-10-15	Verfahren zur herstellung von 1,3,5-triazacycloheptan-2,4-dionderivaten
DE2337796A1 (de)	1974-02-07	Neue piperidinderivate
DE2233122A1 (de)	1973-01-25	Piperidin-spiro-hydantoin-derivate und ihre verwendung als stabilisatoren
EP0000487A1 (fr)	1979-02-07	Composés portant des groupes énols, leurs chélates métalliques, leur préparation et leur emploi comme stabilisants contre la lumière, en particulier pour des substances polymères.
EP0232224A2 (fr)	1987-08-12	Composés de pipéridine
DE2330906A1 (de)	1974-01-10	Nickel-stabilisatoren fuer synthetische polymere
DE2254476A1 (de)	1973-05-17	Nickel-komplexe von 2-(2'-hydroxyphenyl)-v-triazolen
DE2459381A1 (de)	1975-07-10	Gehinderte piperidin-carbonsaeuren und ihre metallsalze
DE2656766A1 (de)	1977-07-07	Neue phosphit-stabilisatoren
DE3602367A1 (de)	1986-07-31	Neue triazolderivate und ihre verwendung zum stabilisieren von organischen polymeren
DE2321526A1 (de)	1973-11-15	Acylderivate substituierter piperazine und deren verwendung zum stabilisieren von polymerisatzusammensetzungen