CS273098B1 - Substituted polyaminotriazines and method of their preparation - Google Patents

Substituted polyaminotriazines and method of their preparation Download PDF

Info

Publication number: CS273098B1
Authority: CS; Czechoslovakia
Prior art keywords: vii; mol; formula; dichlorotriazine; tetramethyl
Prior art date: 1989-01-02

Application number

CS1389A

Other languages

Czech (cs)

English (en)

Slovak (sk)

Other versions

CS1389A1 (en

Inventor

Zdenek Ing Csc Manasek

Pavol Rndr Csc Hrdlovic

Stefan Csc Chmela

Jozef Ing Csc Rychly

Peter Rndr Danko

Milan Ing Csc Karvas

Frantisek Rndr Csc Vass

Julius Ing Csc Durmis

Jan Ing Masek

Original Assignee

Manasek Zdenek

Hrdlovic Pavol

Stefan Csc Chmela

Jozef Ing Csc Rychly

Danko Peter

Karvas Milan

Vass Frantisek

Durmis Julius

Masek Jan

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.)

1989-01-02

Filing date

1989-01-02

Publication date

1991-03-12

1989-01-02 Application filed by Manasek Zdenek, Hrdlovic Pavol, Stefan Csc Chmela, Jozef Ing Csc Rychly, Danko Peter, Karvas Milan, Vass Frantisek, Durmis Julius, Masek Jan filed Critical Manasek Zdenek

1989-01-02 Priority to CS1389A priority Critical patent/CS273098B1/cs

1989-12-27 Priority to EP19890313616 priority patent/EP0377324A3/fr

1990-07-12 Publication of CS1389A1 publication Critical patent/CS1389A1/cs

1991-03-12 Publication of CS273098B1 publication Critical patent/CS273098B1/cs

Links

238000000034 method Methods 0.000 title claims abstract description 31
238000002360 preparation method Methods 0.000 title claims abstract description 8
-1 1,2.2, 6,6 - pentamethyl - 4 - piperidyl group Chemical group 0.000 claims abstract description 68
150000004985 diamines Chemical class 0.000 claims abstract description 25
238000006243 chemical reaction Methods 0.000 claims abstract description 19
MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 claims abstract description 18
229910052801 chlorine Inorganic materials 0.000 claims abstract description 16
150000007529 inorganic bases Chemical class 0.000 claims abstract description 16
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims abstract description 14
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 claims abstract description 11
239000001257 hydrogen Substances 0.000 claims abstract description 10
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
239000003960 organic solvent Substances 0.000 claims abstract description 8
125000000217 alkyl group Chemical group 0.000 claims abstract description 7
150000001875 compounds Chemical class 0.000 claims description 62
229920001577 copolymer Polymers 0.000 claims description 30
IHDBZCJYSHDCKF-UHFFFAOYSA-N 4,6-dichlorotriazine Chemical compound ClC1=CC(Cl)=NN=N1 IHDBZCJYSHDCKF-UHFFFAOYSA-N 0.000 claims description 26
239000000460 chlorine Substances 0.000 claims description 17
125000001309 chloro group Chemical group Cl* 0.000 claims description 11
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 4
125000003282 alkyl amino group Chemical group 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 2
150000003973 alkyl amines Chemical class 0.000 claims description 2
239000012442 inert solvent Substances 0.000 claims description 2
125000004435 hydrogen atom Chemical class [H]* 0.000 claims 3
101100347612 Arabidopsis thaliana VIII-B gene Proteins 0.000 claims 1
ADIGAFWLDDSRAG-UHFFFAOYSA-N [ClH]1[ClH]N=NN=C1 Chemical class [ClH]1[ClH]N=NN=C1 ADIGAFWLDDSRAG-UHFFFAOYSA-N 0.000 claims 1
125000004414 alkyl thio group Chemical group 0.000 claims 1
239000004611 light stabiliser Substances 0.000 abstract description 16
FTVFPPFZRRKJIH-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidin-4-amine Chemical compound CC1(C)CC(N)CC(C)(C)N1 FTVFPPFZRRKJIH-UHFFFAOYSA-N 0.000 abstract description 5
150000001412 amines Chemical class 0.000 abstract description 5
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 abstract description 4
125000001424 substituent group Chemical group 0.000 abstract description 3
OMRXVBREYFZQHU-UHFFFAOYSA-N 2,4-dichloro-1,3,5-triazine Chemical compound ClC1=NC=NC(Cl)=N1 OMRXVBREYFZQHU-UHFFFAOYSA-N 0.000 abstract description 2
238000009833 condensation Methods 0.000 abstract 1
230000005494 condensation Effects 0.000 abstract 1
230000006735 deficit Effects 0.000 abstract 1
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 56
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 52
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 45
239000000243 solution Substances 0.000 description 42
239000003381 stabilizer Substances 0.000 description 30
239000000047 product Substances 0.000 description 24
239000000203 mixture Substances 0.000 description 23
238000003756 stirring Methods 0.000 description 23
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 21
239000008096 xylene Substances 0.000 description 21
239000011541 reaction mixture Substances 0.000 description 14
239000004743 Polypropylene Substances 0.000 description 12
229920001155 polypropylene Polymers 0.000 description 12
229920000642 polymer Polymers 0.000 description 11
125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 10
239000012298 atmosphere Substances 0.000 description 9
238000010438 heat treatment Methods 0.000 description 9
239000002904 solvent Substances 0.000 description 9
239000004698 Polyethylene Substances 0.000 description 8
229920000573 polyethylene Polymers 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
238000001816 cooling Methods 0.000 description 7
238000002844 melting Methods 0.000 description 7
230000008018 melting Effects 0.000 description 7
238000010992 reflux Methods 0.000 description 7
NPYDPROENPLGBR-UHFFFAOYSA-N 4,6-dichloro-n-cyclohexyl-1,3,5-triazin-2-amine Chemical compound ClC1=NC(Cl)=NC(NC2CCCCC2)=N1 NPYDPROENPLGBR-UHFFFAOYSA-N 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 5
235000013539 calcium stearate Nutrition 0.000 description 5
239000008116 calcium stearate Substances 0.000 description 5
238000000605 extraction Methods 0.000 description 5
239000000835 fiber Substances 0.000 description 5
239000011888 foil Substances 0.000 description 5
NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical class NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 5
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
150000002431 hydrogen Chemical group 0.000 description 4
238000002835 absorbance Methods 0.000 description 3
235000010354 butylated hydroxytoluene Nutrition 0.000 description 3
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
239000008187 granular material Substances 0.000 description 3
239000012535 impurity Substances 0.000 description 3
239000000049 pigment Substances 0.000 description 3
125000005936 piperidyl group Chemical group 0.000 description 3
229920000098 polyolefin Polymers 0.000 description 3
230000005855 radiation Effects 0.000 description 3
HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 description 2
FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 2
RFTJIJFLPFVJKR-UHFFFAOYSA-N 2,2,5,6-tetramethylpiperidin-4-amine Chemical compound CC1NC(C)(C)CC(N)C1C RFTJIJFLPFVJKR-UHFFFAOYSA-N 0.000 description 2
XOUQAVYLRNOXDO-UHFFFAOYSA-N 2-tert-butyl-5-methylphenol Chemical compound CC1=CC=C(C(C)(C)C)C(O)=C1 XOUQAVYLRNOXDO-UHFFFAOYSA-N 0.000 description 2
UQAMDAUJTXFNAD-UHFFFAOYSA-N 4-(4,6-dichloro-1,3,5-triazin-2-yl)morpholine Chemical compound ClC1=NC(Cl)=NC(N2CCOCC2)=N1 UQAMDAUJTXFNAD-UHFFFAOYSA-N 0.000 description 2
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
239000004793 Polystyrene Substances 0.000 description 2
WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Chemical class 0.000 description 2
239000003963 antioxidant agent Substances 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
230000005540 biological transmission Effects 0.000 description 2
238000009835 boiling Methods 0.000 description 2
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
238000006731 degradation reaction Methods 0.000 description 2
125000003963 dichloro group Chemical class Cl* 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
239000000284 extract Substances 0.000 description 2
239000012632 extractable Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
238000002156 mixing Methods 0.000 description 2
IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 2
AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 2
238000007539 photo-oxidation reaction Methods 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
238000006068 polycondensation reaction Methods 0.000 description 2
229920002223 polystyrene Polymers 0.000 description 2
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
230000000087 stabilizing effect Effects 0.000 description 2
239000000126 substance Substances 0.000 description 2
238000012360 testing method Methods 0.000 description 2
HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 2
229940089401 xylon Drugs 0.000 description 2
ATLWFAZCZPSXII-UHFFFAOYSA-N (2-octylphenyl) 2-hydroxybenzoate Chemical compound CCCCCCCCC1=CC=CC=C1OC(=O)C1=CC=CC=C1O ATLWFAZCZPSXII-UHFFFAOYSA-N 0.000 description 1
ZEBMSMUPGIOANU-UHFFFAOYSA-N (3,5-ditert-butyl-4-hydroxyphenyl)methylphosphonic acid Chemical class CC(C)(C)C1=CC(CP(O)(O)=O)=CC(C(C)(C)C)=C1O ZEBMSMUPGIOANU-UHFFFAOYSA-N 0.000 description 1
MARCAKLHFUYDJE-UHFFFAOYSA-N 1,2-xylene;hydrate Chemical compound O.CC1=CC=CC=C1C MARCAKLHFUYDJE-UHFFFAOYSA-N 0.000 description 1
DKCPKDPYUFEZCP-UHFFFAOYSA-N 2,6-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1O DKCPKDPYUFEZCP-UHFFFAOYSA-N 0.000 description 1
LDXJRKWFNNFDSA-UHFFFAOYSA-N 2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound C1CN(CC2=NNN=C21)CC(=O)N3CCN(CC3)C4=CN=C(N=C4)NCC5=CC(=CC=C5)OC(F)(F)F LDXJRKWFNNFDSA-UHFFFAOYSA-N 0.000 description 1
FEXBEKLLSUWSIM-UHFFFAOYSA-N 2-Butyl-4-methylphenol Chemical compound CCCCC1=CC(C)=CC=C1O FEXBEKLLSUWSIM-UHFFFAOYSA-N 0.000 description 1
ZRPAUEVGEGEPFQ-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]pyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2 ZRPAUEVGEGEPFQ-UHFFFAOYSA-N 0.000 description 1
NJBCRXCAPCODGX-UHFFFAOYSA-N 2-methyl-n-(2-methylpropyl)propan-1-amine Chemical compound CC(C)CNCC(C)C NJBCRXCAPCODGX-UHFFFAOYSA-N 0.000 description 1
INMRJUGWMTWQCB-UHFFFAOYSA-N 4,6-dichloro-n,n-di(propan-2-yl)-1,3,5-triazin-2-amine Chemical compound CC(C)N(C(C)C)C1=NC(Cl)=NC(Cl)=N1 INMRJUGWMTWQCB-UHFFFAOYSA-N 0.000 description 1
HYWCPNMPNFJCMD-UHFFFAOYSA-N 4,6-dichloro-n,n-diethyl-1,3,5-triazin-2-amine Chemical compound CCN(CC)C1=NC(Cl)=NC(Cl)=N1 HYWCPNMPNFJCMD-UHFFFAOYSA-N 0.000 description 1
KUCNLYDMWLYXSD-UHFFFAOYSA-N 4,6-dichloro-n-(2,2,6,6-tetramethylpiperidin-4-yl)-1,3,5-triazin-2-amine Chemical compound C1C(C)(C)NC(C)(C)CC1NC1=NC(Cl)=NC(Cl)=N1 KUCNLYDMWLYXSD-UHFFFAOYSA-N 0.000 description 1
QJCXYBJWBBTUOQ-UHFFFAOYSA-N 4,6-dichloro-n-octyl-1,3,5-triazin-2-amine Chemical compound CCCCCCCCNC1=NC(Cl)=NC(Cl)=N1 QJCXYBJWBBTUOQ-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
RTNUTCOTGVKVBR-UHFFFAOYSA-N 4-chlorotriazine Chemical class ClC1=CC=NN=N1 RTNUTCOTGVKVBR-UHFFFAOYSA-N 0.000 description 1
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
DFMVPAMIPDBPJY-UHFFFAOYSA-N CCCCCC.CC1(NC(CC(C1)N)(C)C)C Chemical compound CCCCCC.CC1(NC(CC(C1)N)(C)C)C DFMVPAMIPDBPJY-UHFFFAOYSA-N 0.000 description 1
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
239000004705 High-molecular-weight polyethylene Substances 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
238000004566 IR spectroscopy Methods 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
XTUVJUMINZSXGF-UHFFFAOYSA-N N-methylcyclohexylamine Chemical compound CNC1CCCCC1 XTUVJUMINZSXGF-UHFFFAOYSA-N 0.000 description 1
REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
239000007983 Tris buffer Substances 0.000 description 1
239000000370 acceptor Substances 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
238000010533 azeotropic distillation Methods 0.000 description 1
QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
UJPWQPPTDGBATQ-UHFFFAOYSA-N butan-1-amine;n-butylbutan-1-amine Chemical compound CCCCN.CCCCNCCCC UJPWQPPTDGBATQ-UHFFFAOYSA-N 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
150000001804 chlorine Chemical class 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
238000004040 coloring Methods 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
229940043279 diisopropylamine Drugs 0.000 description 1
238000004821 distillation Methods 0.000 description 1
JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
MCPKSFINULVDNX-UHFFFAOYSA-N drometrizole Chemical compound CC1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 MCPKSFINULVDNX-UHFFFAOYSA-N 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000009977 dual effect Effects 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
DOPACFXNJVWVGW-UHFFFAOYSA-N ethanamine;hexane Chemical compound CCN.CCCCCC DOPACFXNJVWVGW-UHFFFAOYSA-N 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
239000000945 filler Substances 0.000 description 1
239000012467 final product Substances 0.000 description 1
239000003063 flame retardant Substances 0.000 description 1
239000008098 formaldehyde solution Substances 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
239000010931 gold Substances 0.000 description 1
229910052737 gold Inorganic materials 0.000 description 1
239000011874 heated mixture Substances 0.000 description 1
229920001903 high density polyethylene Polymers 0.000 description 1
239000004700 high-density polyethylene Substances 0.000 description 1
229920001519 homopolymer Polymers 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
125000001841 imino group Chemical group [H]N=* 0.000 description 1
230000006698 induction Effects 0.000 description 1
ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
238000002955 isolation Methods 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
239000004816 latex Substances 0.000 description 1
229920000126 latex Polymers 0.000 description 1
229920000092 linear low density polyethylene Polymers 0.000 description 1
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239000011159 matrix material Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
230000001035 methylating effect Effects 0.000 description 1
238000013508 migration Methods 0.000 description 1
230000005012 migration Effects 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
WBQFAPPGEOMPGO-UHFFFAOYSA-N n'-[1-(2,2,6,6-tetramethylpiperidin-4-yl)propan-2-yl]hexane-1,6-diamine Chemical compound NCCCCCCNC(C)CC1CC(C)(C)NC(C)(C)C1 WBQFAPPGEOMPGO-UHFFFAOYSA-N 0.000 description 1
UKJARPDLRWBRAX-UHFFFAOYSA-N n,n'-bis(2,2,6,6-tetramethylpiperidin-4-yl)hexane-1,6-diamine Chemical compound C1C(C)(C)NC(C)(C)CC1NCCCCCCNC1CC(C)(C)NC(C)(C)C1 UKJARPDLRWBRAX-UHFFFAOYSA-N 0.000 description 1
DRUJRGBCHIAAKR-UHFFFAOYSA-N n,n-diethylmorpholin-4-amine Chemical compound CCN(CC)N1CCOCC1 DRUJRGBCHIAAKR-UHFFFAOYSA-N 0.000 description 1
FDAKZQLBIFPGSV-UHFFFAOYSA-N n-butyl-2,2,6,6-tetramethylpiperidin-4-amine Chemical compound CCCCNC1CC(C)(C)NC(C)(C)C1 FDAKZQLBIFPGSV-UHFFFAOYSA-N 0.000 description 1
KXLFRPCCBGEZJH-UHFFFAOYSA-N n-cyclohexyl-1,3,5-triazin-2-amine Chemical compound C1CCCCC1NC1=NC=NC=N1 KXLFRPCCBGEZJH-UHFFFAOYSA-N 0.000 description 1
WSTNFGAKGUERTC-UHFFFAOYSA-N n-ethylhexan-1-amine Chemical compound CCCCCCNCC WSTNFGAKGUERTC-UHFFFAOYSA-N 0.000 description 1
UZUCIYYGGBSFAB-UHFFFAOYSA-N n-hexyl-2,2,6,6-tetramethylpiperidin-4-amine Chemical compound CCCCCCNC1CC(C)(C)NC(C)(C)C1 UZUCIYYGGBSFAB-UHFFFAOYSA-N 0.000 description 1
150000002815 nickel Chemical class 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
238000006384 oligomerization reaction Methods 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
150000003053 piperidines Chemical class 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
239000004417 polycarbonate Substances 0.000 description 1
229920000515 polycarbonate Polymers 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
229920000570 polyether Polymers 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
229920002635 polyurethane Polymers 0.000 description 1
239000004814 polyurethane Substances 0.000 description 1
239000001103 potassium chloride Substances 0.000 description 1
235000011164 potassium chloride Nutrition 0.000 description 1
239000000843 powder Substances 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
238000012545 processing Methods 0.000 description 1
239000005297 pyrex Substances 0.000 description 1
239000000376 reactant Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
230000006641 stabilisation Effects 0.000 description 1
238000011105 stabilization Methods 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
229920001169 thermoplastic Polymers 0.000 description 1
QUTZUATVZPXUJR-UHFFFAOYSA-N trinonyl phosphite Chemical compound CCCCCCCCCOP(OCCCCCCCCC)OCCCCCCCCC QUTZUATVZPXUJR-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1
238000004804 winding Methods 0.000 description 1
229920001221 xylan Polymers 0.000 description 1
150000004823 xylans Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
- C08G73/0273—Polyamines containing heterocyclic moieties in the main chain
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/0622—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms
- C08G73/0638—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms with at least three nitrogen atoms in the ring
- C08G73/0644—Poly(1,3,5)triazines
- 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
- C08K5/3477—Six-membered rings
- C08K5/3492—Triazines
- C08K5/34926—Triazines also containing heterocyclic groups other than triazine groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Compositions Of Macromolecular Compounds (AREA)

CS1389A 1989-01-02 1989-01-02 Substituted polyaminotriazines and method of their preparation CS273098B1 (en)

Priority Applications (2)

Application Number	Priority Date	Filing Date	Title
CS1389A CS273098B1 (en)	1989-01-02	1989-01-02	Substituted polyaminotriazines and method of their preparation
EP19890313616 EP0377324A3 (fr)	1989-01-02	1989-12-27	Polyaminotriazines substituées et leur méthode de préparation

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CS1389A CS273098B1 (en)	1989-01-02	1989-01-02	Substituted polyaminotriazines and method of their preparation

Publications (2)

Publication Number	Publication Date
CS1389A1 CS1389A1 (en)	1990-07-12
CS273098B1 true CS273098B1 (en)	1991-03-12

Family

ID=5331538

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS1389A CS273098B1 (en)	1989-01-02	1989-01-02	Substituted polyaminotriazines and method of their preparation

Country Status (2)

Country	Link
EP (1)	EP0377324A3 (fr)
CS (1)	CS273098B1 (fr)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IT1243433B (it) *	1990-10-03	1994-06-10	Ciba Geigy Spa	Composti piperidin-triazinici atti all'impiego come stabilizzanti per materiali organici
US5256787A (en) *	1990-09-03	1993-10-26	Ciba-Geigy Corporation	Tri-piperdine compounds as stabilizers for organic materials
TW302377B (fr) *	1993-12-24	1997-04-11	Sumitomo Chemical Co
US6046304A (en) *	1995-12-04	2000-04-04	Ciba Specialty Chemicals Corporation	Block oligomers containing 2,2,6,6-tetramethyl-4-piperidyl groups as stabilizers for organic materials
DE69719004T2 (de)	1996-12-24	2003-07-24	Ciba Speciality Chemicals Holding Inc., Basel	Triazinverbindungen die 2,2,6,6-Tetramethyl-4-piperidingruppen enthalten als Stabilisatoren für organische Materialen
TW509683B (en) *	1997-05-27	2002-11-11	Ciba Sc Holding Ag	Triazine derivatives containing 2,2,6,6-tetramethyl-4-piperidyl groups
TW589341B (en)	1997-05-27	2004-06-01	Ciba Sc Holding Ag	Block oligomers containing 1-hydrocarbyloxy-2,2,6,6-tetramethyl-4-piperidyl groups as stabilizers for organic materials
JP4332817B2 (ja)	1997-05-27	2009-09-16	チバスペシャルティケミカルズホールディングインコーポレーテッド	有機材料のための安定剤としての１−ヒドロカルビルオキシ−２，２，６，６−テトラメチル−４−ピペリジル基を含むブロックオリゴマー
TW428008B (en)	1997-05-27	2001-04-01	Ciba Sc Holding Ag	Block oligomers containing 1-hydrocarbyloxy-2,2,6,6-tetramethy1-4-piperidyl groups as stabilizers for organic materials
CN1094938C (zh)	1997-05-27	2002-11-27	西巴特殊化学品控股有限公司	作为有机材料稳定剂的含有1－烃氧基－2,2,6,6－四甲基－4－哌啶基的嵌段低聚物
TW491872B (en) *	1997-05-27	2002-06-21	Ciba Sc Holding Ag	Block oligomers containing l-hydrocarbyloxy-2,2,6,6-tetramethyl-4- piperidyl groups as stabilizers for lower polyolefin
IT1292040B1 (it) *	1997-05-30	1999-01-25	Ciba Spec Chem Spa	Processo per la preparazione di prodotti politriazinici contenenti gruppi 2,2,6,6-tetrametil-4-piperidile
JP2001525404A (ja) *	1997-12-08	2001-12-11	サイテク・テクノロジー・コーポレーシヨン	モルホリノでエンドキャップされ、ヒンダードアミンにより置換されたアミノトリアジンおよびそれらの光安定剤としての使用
EP2130854B1 (fr)	2008-05-09	2016-10-19	MCA Technologies GMBH	Composés de type polytriazinyl en tant que substances ignifuges et stabilisants à la lumière
US9562137B2 (en)	2014-09-03	2017-02-07	Battelle Memorial Institute	Synthetic polymers and methods of making and using the same
US9365676B2 (en) *	2014-09-03	2016-06-14	Battelle Memorial Institute	Synthetic polymers and methods of making and using the same

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1393551A (en) *	1972-04-21	1975-05-07	Ciba Geigy Ag	Piperidine derivatives
IT1151035B (it) *	1980-07-31	1986-12-17	Chimosa Chimica Organica Spa	Piperidil-derivati di copolimeri triazinici,processi per la loro preparazione e composizioni stabilizzate che li comprendono

1989
- 1989-01-02 CS CS1389A patent/CS273098B1/cs unknown
- 1989-12-27 EP EP19890313616 patent/EP0377324A3/fr not_active Withdrawn

Also Published As

Publication number	Publication date
EP0377324A3 (fr)	1991-10-02
EP0377324A2 (fr)	1990-07-11
CS1389A1 (en)	1990-07-12

Publication	Publication Date	Title
CS273098B1 (en)	1991-03-12	Substituted polyaminotriazines and method of their preparation
EP0070358B1 (fr)	1987-01-21	Nouveaux stabilisateurs à la lumière pour des polymères
DK167017B1 (da)	1993-08-16	2,2,6,6-tetramethylpiperidylgruppeholdige 1,3,5-triazinylforbindelser, fremgangsmaade til fremstilling deraf samt middel til stabilisering af polymerer
EP2130854B1 (fr)	2016-10-19	Composés de type polytriazinyl en tant que substances ignifuges et stabilisants à la lumière
US4629752A (en)	1986-12-16	Substituted oxo-piperazinyl-triazines and UV light stabilized compositions
US4459395A (en)	1984-07-10	Piperidyl derivatives of triazine copolymers, processes for their preparation and stabilized composition containing these derivatives
AU2002321111B2 (en)	2006-12-21	Highly compatible hydroxyphenyltriazine UV-absorbers
JPS649995B2 (fr)	1989-02-21
EP0357223A2 (fr)	1990-03-07	Polyaminotriazines et procédé pour leur préparation
US4376836A (en)	1983-03-15	Triazylaminotriazines, their preparation and their use for stabilizing synthetic polymers
US4348493A (en)	1982-09-07	Novel light stabilizers for polymers
US5210120A (en)	1993-05-11	Self-extinguishing polymeric compositions comprising oligomeric 2,4-diamino-6-hydroxy-1,3,5-triazines and phosphates and/or phosphonates
GB1580940A (en)	1980-12-10	Stabilisers for synthetic polymers and a process for their preparation
EP0475367B1 (fr)	1996-03-20	Dérivés de la diamino s-triazinone et compositions polymères auto-extinctrices les contenant
EP0448774B1 (fr)	1994-10-12	Composés triaziniques
US5629382A (en)	1997-05-13	Self-extinguishing polymeric compositions
GB2345485A (en)	2000-07-12	Sterically hindered amines as stabilisers to actinic radiation in polymers
EP0070386B1 (fr)	1989-01-11	Agents de protection contre la lumière pour polymères
CA2005235C (fr)	1999-09-21	Esters et amides oligomeriques de triazine termines par un groupement piperidyle tetramethyle
EP0542373B1 (fr)	1998-06-17	Polyphosphate d'ammonium micro-encapsulé à l'aide de résine aminoplaste
EP0551153B1 (fr)	1997-12-17	Dérivés d'acide 2,4-diamino-1,3,5-triazinyl-6-phosphonique
EP0542370B1 (fr)	1997-01-29	Compositions polymériques auto-extinctrices
US4981964A (en)	1991-01-01	Oligomeric polyesters and polyamides containing dipiperidyl triazine groups
SU600140A1 (ru)	1978-03-30	Производные 2,2,6,6- тетраметил-4пиперидиламино-бис-триазинил- алкилен диаминов в качестве светостабилизаторов полимеров
EP0189877A2 (fr)	1986-08-06	2-Céto-1,4-diazacycloalcane oligomères entravés contenant des cycles triazine ou des groupes esters et compositions stabilisées par eux