NL7905001A - Gesubstitueerde oxazoline-verbindingen, alsmede organische materialen die met behulp van deze verbin- dingen gestabiliseerd zijn. - Google Patents

Gesubstitueerde oxazoline-verbindingen, alsmede organische materialen die met behulp van deze verbin- dingen gestabiliseerd zijn. Download PDF

Info

Publication number: NL7905001A
Authority: NL; Netherlands
Prior art keywords: chj; oxazoline; formula; group; chs
Prior art date: 1978-10-18

Application number

NL7905001A

Other languages

English (en)

Dutch (nl)

Original Assignee

Cincinnati Milacron Chem

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.)

1978-10-18

Filing date

1979-06-27

Publication date

1980-04-22

1979-06-27 Application filed by Cincinnati Milacron Chem filed Critical Cincinnati Milacron Chem

1980-04-22 Publication of NL7905001A publication Critical patent/NL7905001A/nl

Links

150000002918 oxazolines Chemical class 0.000 title claims description 40
150000001875 compounds Chemical class 0.000 title description 36
239000011368 organic material Chemical class 0.000 title description 9
-1 Oxazoline compound Chemical class 0.000 claims description 72
125000004432 carbon atom Chemical group C* 0.000 claims description 27
239000002253 acid Substances 0.000 claims description 26
238000000034 method Methods 0.000 claims description 23
125000000217 alkyl group Chemical group 0.000 claims description 15
230000006866 deterioration Effects 0.000 claims description 15
125000001183 hydrocarbyl group Chemical group 0.000 claims description 14
230000001590 oxidative effect Effects 0.000 claims description 14
239000000463 material Substances 0.000 claims description 11
125000003504 2-oxazolinyl group Chemical group O1C(=NCC1)* 0.000 claims description 10
239000000203 mixture Substances 0.000 claims description 10
229920001577 copolymer Polymers 0.000 claims description 8
229910052799 carbon Inorganic materials 0.000 claims description 7
229920000098 polyolefin Polymers 0.000 claims description 7
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 6
239000005977 Ethylene Substances 0.000 claims description 6
125000002947 alkylene group Chemical group 0.000 claims description 6
150000002148 esters Chemical group 0.000 claims description 6
229920001519 homopolymer Polymers 0.000 claims description 6
238000010525 oxidative degradation reaction Methods 0.000 claims description 6
230000000087 stabilizing effect Effects 0.000 claims description 6
239000000126 substance Substances 0.000 claims description 6
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
229920000642 polymer Polymers 0.000 claims description 3
239000003381 stabilizer Substances 0.000 claims 5
241000906142 Balistes polylepis Species 0.000 claims 1
ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical compound O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims 1
229920001384 propylene homopolymer Polymers 0.000 claims 1
238000002844 melting Methods 0.000 description 17
230000008018 melting Effects 0.000 description 17
239000000178 monomer Substances 0.000 description 11
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
239000000047 product Substances 0.000 description 8
239000007787 solid Substances 0.000 description 8
229920006395 saturated elastomer Polymers 0.000 description 7
125000001424 substituent group Chemical group 0.000 description 7
229920002554 vinyl polymer Polymers 0.000 description 7
IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 description 6
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
125000001931 aliphatic group Chemical group 0.000 description 6
239000003921 oil Substances 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
235000019198 oils Nutrition 0.000 description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 5
239000008096 xylene Substances 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
239000000654 additive Substances 0.000 description 4
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
238000002845 discoloration Methods 0.000 description 4
150000002825 nitriles Chemical class 0.000 description 4
230000003647 oxidation Effects 0.000 description 4
238000007254 oxidation reaction Methods 0.000 description 4
239000002904 solvent Substances 0.000 description 4
UXFQFBNBSPQBJW-UHFFFAOYSA-N 2-amino-2-methylpropane-1,3-diol Chemical compound OCC(N)(C)CO UXFQFBNBSPQBJW-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
239000003963 antioxidant agent Substances 0.000 description 3
230000003078 antioxidant effect Effects 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
238000010533 azeotropic distillation Methods 0.000 description 3
239000011521 glass Substances 0.000 description 3
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 3
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
230000000379 polymerizing effect Effects 0.000 description 3
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
229930195735 unsaturated hydrocarbon Natural products 0.000 description 3
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 2
IOAOAKDONABGPZ-UHFFFAOYSA-N 2-amino-2-ethylpropane-1,3-diol Chemical compound CCC(N)(CO)CO IOAOAKDONABGPZ-UHFFFAOYSA-N 0.000 description 2
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
239000004215 Carbon black (E152) Substances 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
239000004952 Polyamide Substances 0.000 description 2
239000004698 Polyethylene Substances 0.000 description 2
239000004743 Polypropylene Substances 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
235000021355 Stearic acid Nutrition 0.000 description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
230000000996 additive effect Effects 0.000 description 2
239000001361 adipic acid Substances 0.000 description 2
235000011037 adipic acid Nutrition 0.000 description 2
125000005907 alkyl ester group Chemical group 0.000 description 2
229940067597 azelate Drugs 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
239000011248 coating agent Substances 0.000 description 2
238000000576 coating method Methods 0.000 description 2
239000013078 crystal Substances 0.000 description 2
150000001993 dienes Chemical class 0.000 description 2
150000002009 diols Chemical class 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
230000003301 hydrolyzing effect Effects 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
125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
239000000314 lubricant Substances 0.000 description 2
239000010687 lubricating oil Substances 0.000 description 2
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
229910052753 mercury Inorganic materials 0.000 description 2
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
125000002347 octyl 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])[H] 0.000 description 2
239000005416 organic matter Substances 0.000 description 2
229920002647 polyamide Polymers 0.000 description 2
229920000573 polyethylene Polymers 0.000 description 2
229920001155 polypropylene Polymers 0.000 description 2
229920002635 polyurethane Polymers 0.000 description 2
239000004814 polyurethane Substances 0.000 description 2
229920000915 polyvinyl chloride Polymers 0.000 description 2
239000004800 polyvinyl chloride Substances 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
229920005989 resin Polymers 0.000 description 2
239000011347 resin Substances 0.000 description 2
239000008117 stearic acid Substances 0.000 description 2
239000010689 synthetic lubricating oil Substances 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
229920006305 unsaturated polyester Polymers 0.000 description 2
235000015112 vegetable and seed oil Nutrition 0.000 description 2
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 description 1
UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 description 1
PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 description 1
125000004825 2,2-dimethylpropylene group Chemical group [H]C([H])([H])C(C([H])([H])[H])(C([H])([H])[*:1])C([H])([H])[*:2] 0.000 description 1
SFRDXVJWXWOTEW-UHFFFAOYSA-N 2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)CO SFRDXVJWXWOTEW-UHFFFAOYSA-N 0.000 description 1
GUXJXWKCUUWCLX-UHFFFAOYSA-N 2-methyl-2-oxazoline Chemical compound CC1=NCCO1 GUXJXWKCUUWCLX-UHFFFAOYSA-N 0.000 description 1
BNCADMBVWNPPIZ-UHFFFAOYSA-N 2-n,2-n,4-n,4-n,6-n,6-n-hexakis(methoxymethyl)-1,3,5-triazine-2,4,6-triamine Chemical compound COCN(COC)C1=NC(N(COC)COC)=NC(N(COC)COC)=N1 BNCADMBVWNPPIZ-UHFFFAOYSA-N 0.000 description 1
125000006024 2-pentenyl group Chemical group 0.000 description 1
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
BKZXZGWHTRCFPX-UHFFFAOYSA-N 2-tert-butyl-6-methylphenol Chemical compound CC1=CC=CC(C(C)(C)C)=C1O BKZXZGWHTRCFPX-UHFFFAOYSA-N 0.000 description 1
239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
229920000089 Cyclic olefin copolymer Polymers 0.000 description 1
229920002943 EPDM rubber Polymers 0.000 description 1
229920006385 Geon Polymers 0.000 description 1
239000004831 Hot glue Substances 0.000 description 1
229920000877 Melamine resin Polymers 0.000 description 1
235000019482 Palm oil Nutrition 0.000 description 1
229930040373 Paraformaldehyde Natural products 0.000 description 1
235000019483 Peanut oil Nutrition 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
239000005062 Polybutadiene Substances 0.000 description 1
229920002367 Polyisobutene Polymers 0.000 description 1
239000004793 Polystyrene Substances 0.000 description 1
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
239000012963 UV stabilizer Substances 0.000 description 1
229920001807 Urea-formaldehyde Polymers 0.000 description 1
XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 1
125000002015 acyclic group Chemical group 0.000 description 1
GZCGUPFRVQAUEE-SLPGGIOYSA-N aldehydo-D-glucose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O GZCGUPFRVQAUEE-SLPGGIOYSA-N 0.000 description 1
125000002723 alicyclic group Chemical group 0.000 description 1
229920000180 alkyd Polymers 0.000 description 1
IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 description 1
125000001204 arachidyl 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])C([H])([H])C([H])([H])[H] 0.000 description 1
125000002029 aromatic hydrocarbon group Chemical group 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
239000003899 bactericide agent Substances 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
238000009835 boiling Methods 0.000 description 1
125000000837 carbohydrate group Chemical group 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
235000013351 cheese Nutrition 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
239000003240 coconut oil Substances 0.000 description 1
235000019864 coconut oil Nutrition 0.000 description 1
235000012716 cod liver oil Nutrition 0.000 description 1
239000003026 cod liver oil Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
235000005687 corn oil Nutrition 0.000 description 1
239000002285 corn oil Substances 0.000 description 1
230000007797 corrosion Effects 0.000 description 1
238000005260 corrosion Methods 0.000 description 1
239000002385 cottonseed oil Substances 0.000 description 1
235000012343 cottonseed oil Nutrition 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
125000002704 decyl 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])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
PWEVMPIIOJUPRI-UHFFFAOYSA-N dimethyltin Chemical compound C[Sn]C PWEVMPIIOJUPRI-UHFFFAOYSA-N 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000000975 dye Substances 0.000 description 1
VXNZUUAINFGPBY-UHFFFAOYSA-N ethyl ethylene Natural products CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
239000003925 fat Substances 0.000 description 1
235000019197 fats Nutrition 0.000 description 1
239000000945 filler Substances 0.000 description 1
239000003063 flame retardant Substances 0.000 description 1
125000001188 haloalkyl group Chemical group 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229920005669 high impact polystyrene Polymers 0.000 description 1
239000004797 high-impact polystyrene Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
125000002768 hydroxyalkyl group Chemical group 0.000 description 1
125000005027 hydroxyaryl group Chemical group 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
239000000944 linseed oil Substances 0.000 description 1
235000021388 linseed oil Nutrition 0.000 description 1
239000007788 liquid Substances 0.000 description 1
JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
229920003052 natural elastomer Polymers 0.000 description 1
239000000025 natural resin Substances 0.000 description 1
229920001194 natural rubber Polymers 0.000 description 1
229920006173 natural rubber latex Polymers 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 1
229960002446 octanoic acid Drugs 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
239000002540 palm oil Substances 0.000 description 1
125000000913 palmityl 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])[H] 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
229920002866 paraformaldehyde Polymers 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
239000000049 pigment Substances 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
229920002239 polyacrylonitrile Polymers 0.000 description 1
229920002857 polybutadiene Polymers 0.000 description 1
229920001748 polybutylene Polymers 0.000 description 1
229920001195 polyisoprene Polymers 0.000 description 1
229920002959 polymer blend Polymers 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
230000005855 radiation Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
238000009331 sowing Methods 0.000 description 1
238000001228 spectrum Methods 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
239000012258 stirred mixture Substances 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
229920003051 synthetic elastomer Polymers 0.000 description 1
239000012209 synthetic fiber Substances 0.000 description 1
229920002994 synthetic fiber Polymers 0.000 description 1
229920003002 synthetic resin Polymers 0.000 description 1
239000000057 synthetic resin Substances 0.000 description 1
239000005061 synthetic rubber Substances 0.000 description 1
239000003784 tall oil Substances 0.000 description 1
229920001897 terpolymer Polymers 0.000 description 1
229940071127 thioglycolate Drugs 0.000 description 1
CWERGRDVMFNCDR-UHFFFAOYSA-M thioglycolate(1-) Chemical compound [O-]C(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-M 0.000 description 1
125000002469 tricosyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000002966 varnish Substances 0.000 description 1
235000019871 vegetable fat Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
238000004383 yellowing Methods 0.000 description 1
239000004711 α-olefin Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/62—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by introduction of halogen; by substitution of halogen atoms by other halogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/08—Preparation of carboxylic acids or their salts, halides or anhydrides from nitriles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/10—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D263/14—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with radicals substituted by oxygen atoms
- 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
- C08K5/35—Heterocyclic compounds having nitrogen in the ring having also oxygen in the ring
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S524/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S524/925—Natural rubber compositions having nonreactive materials, i.e. NRM, other than: carbon, silicon dioxide, glass titanium dioxide, water, hydrocarbon or halohydrocarbon
- Y10S524/926—Natural rubber compositions having nonreactive materials, i.e. NRM, other than: carbon, silicon dioxide, glass titanium dioxide, water, hydrocarbon or halohydrocarbon with water as NRM, exemplified

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Oil, Petroleum & Natural Gas (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Compositions Of Macromolecular Compounds (AREA)

NL7905001A 1978-10-18 1979-06-27 Gesubstitueerde oxazoline-verbindingen, alsmede organische materialen die met behulp van deze verbin- dingen gestabiliseerd zijn. NL7905001A (nl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US05/952,492 US4205176A (en)	1978-10-18	1978-10-18	Ester substituted oxazolines
US95249278		1978-10-18

Publications (1)

Publication Number	Publication Date
NL7905001A true NL7905001A (nl)	1980-04-22

Family

ID=25492959

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL7905001A NL7905001A (nl)	1978-10-18	1979-06-27	Gesubstitueerde oxazoline-verbindingen, alsmede organische materialen die met behulp van deze verbin- dingen gestabiliseerd zijn.

Country Status (9)

Country	Link
US (1)	US4205176A (fr)
JP (1)	JPS5555172A (fr)
AU (1)	AU515167B2 (fr)
BE (1)	BE878550A (fr)
CA (1)	CA1122988A (fr)
DE (1)	DE2929341A1 (fr)
FR (1)	FR2439190A1 (fr)
GB (1)	GB2031891A (fr)
NL (1)	NL7905001A (fr)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4755167A (en) *	1984-04-10	1988-07-05	Research Corporation	In vivo method for distribution and stirring of therapeutic agents
US4723941A (en) *	1985-09-06	1988-02-09	Research Corporation	Pump for oscillating a fluid in vivo
JPH0694500B2 (ja) *	1987-10-02	1994-11-24	ポリプラスチックス株式会社	難燃性改良成形用熱可塑性ポリエステル樹脂の製造法
US5037867A (en) *	1990-04-12	1991-08-06	Ciba-Geigy Corporation	Stabilized compositions containing substituted isoxazolidines
US5405727A (en) *	1993-12-22	1995-04-11	Eastman Kodak Company	N-(carbonyl, carbonimidoyl, carbonothioyl) sulfonamide charge control agents and toners and developers
US5962683A (en) *	1996-06-28	1999-10-05	Ciba Specialty Chemicals Corp.	Oxazoline compounds as stabilizers
US5698017A (en) *	1996-09-27	1997-12-16	Xerox Corporation	Oxazoline hot melt ink compositions

Family Cites Families (22)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2504951A (en) *	1944-09-11	1950-04-25	Commercial Solvents Corp	Preparation of acyloxymethyl oxazolines
US2517893A (en) *	1946-05-13	1950-08-08	Du Pont	Stabilized chlorohydrocarbon cleaning composition
US3248397A (en) *	1964-12-04	1966-04-26	Commercial Solvents Corp	Process for bodying oxazoline drying oils and product thereof
US3553124A (en) *	1965-09-30	1971-01-05	Du Pont	Coating compositions comprising acrylic polymers containing an oxazoline drying oil constituent
US3488307A (en) *	1965-09-30	1970-01-06	Du Pont	Coating compositions comprising mixtures of nitrogen-containing acrylic polymers
US3435065A (en) *	1965-10-22	1969-03-25	Geigy Chem Corp	N,n,n',n' - (ethylenediamine) - tetrakis (ethylene - 3 - (3',5' - di-tert-butyl-4' - hydroxyphenyl)propionate) and compositions stabilized therewith
US3380975A (en) *	1966-07-07	1968-04-30	Commercial Solvents Corp	Vinyl halide resins containing oxazoline heat stabilizers
US3380959A (en) *	1966-07-07	1968-04-30	Commercial Solvents Corp	Vinyl halide resins containing oxazoline heat stabilizers
US3493635A (en) *	1967-06-28	1970-02-03	Reichhold Chemicals Inc	Polyester resins containing oxazoline derivatives
US3535332A (en) *	1968-03-11	1970-10-20	Commercial Solvents Corp	Production of vinyl oxazoline esters
US3654229A (en) *	1970-05-12	1972-04-04	Commercial Solvents Corp	Baking enamel vehicle comprising the reaction product of an oxazoline with melamine and formaldehyde
US3649667A (en) *	1970-06-24	1972-03-14	American Cyanamid Co	Aryl polyesters of 3 5-dialkyl-4-hydroxy-phenyl-alkanoic acids
US3678065A (en) *	1970-12-09	1972-07-18	Commercial Solvents Corp	Production of hydroxymethyl vinyl oxazoline
FR2123880A5 (fr) *	1971-02-03	1972-09-15	Inst Francais Du Petrole
US3737408A (en) *	1971-09-30	1973-06-05	Commercial Solvents Corp	Baking enamel vehicle comprising the reaction product of an oxazoline with phenol
GB1396726A (en) *	1972-06-15	1975-06-04	Boots Co Ltd	Phenylalkanoic acids
US3967015A (en) *	1972-10-10	1976-06-29	Commercial Solvents Corporation	Process for dyeing glass textiles
HU167760B (fr) *	1972-10-20	1975-12-25
US4034097A (en) *	1973-09-27	1977-07-05	Mortell Company	Synergistic biostatic composition
US4032562A (en) *	1974-11-05	1977-06-28	Ciba-Geigy Corporation	3,5-dialkyl-4-hydroxyphenylalkanoic acid esters of polyalkylene glycols
CH611284A5 (fr) *	1975-04-10	1979-05-31	Ciba Geigy Ag
CA1133908A (fr) *	1978-08-04	1982-10-19	Edward L. Wheeler	Derives de la 2-oxazoline a proprietes anti-oxydantes

1978
- 1978-10-18 US US05/952,492 patent/US4205176A/en not_active Expired - Lifetime
1979
- 1979-05-28 AU AU47472/79A patent/AU515167B2/en not_active Expired - Fee Related
- 1979-06-27 CA CA330,738A patent/CA1122988A/fr not_active Expired
- 1979-06-27 NL NL7905001A patent/NL7905001A/nl not_active Application Discontinuation
- 1979-07-20 DE DE19792929341 patent/DE2929341A1/de not_active Withdrawn
- 1979-07-20 JP JP9250579A patent/JPS5555172A/ja active Pending
- 1979-08-08 FR FR7920302A patent/FR2439190A1/fr active Pending
- 1979-08-31 BE BE0/196978A patent/BE878550A/fr unknown
- 1979-10-01 GB GB7933963A patent/GB2031891A/en not_active Withdrawn

Also Published As

Publication number	Publication date
GB2031891A (en)	1980-04-30
AU515167B2 (en)	1981-03-19
DE2929341A1 (de)	1980-04-24
BE878550A (fr)	1979-12-17
FR2439190A1 (fr)	1980-05-16
AU4747279A (en)	1980-05-08
JPS5555172A (en)	1980-04-22
CA1122988A (fr)	1982-05-04
US4205176A (en)	1980-05-27

Legal Events

Date	Code	Title	Description
1982-02-01	BV	The patent application has lapsed

Publication	Publication Date	Title
EP0022749B1 (fr)	1983-05-18	Esters formés d'acides bêta-cétocarboxyliques et d'alcanolamides et leur utilisation pour stabiliser des matières thermoplastiques contenant du chlore
EP0511156B1 (fr)	1997-07-09	Aryl phosphites non-symétriques
NL7905000A (nl)	1980-03-27	Gehinderde fenolverbindingen, alsmede organische mate- rialen die met behulp daarvan gestabiliseerd zijn tegen oxydatieve aantasting.
JPS6322064A (ja)	1988-01-29	ペンタエリスリト−ル共エステル
DE2422158A1 (de)	1974-12-12	3-hydroxybenzyl-oxadiazolon- und thiadiazolonderivate
DE2929993A1 (de)	1980-02-07	Neue stabilisatoren
NL7905001A (nl)	1980-04-22	Gesubstitueerde oxazoline-verbindingen, alsmede organische materialen die met behulp van deze verbin- dingen gestabiliseerd zijn.
EP0466640B1 (fr)	1995-05-24	Dérivés d'alpha-carbonylphénylacéronitrile comme stabilisateurs de substances organiques
EP0019578B1 (fr)	1983-03-30	Dérivés de la pipéridine, procédé pour leur préparation et compositions polymères les contenant
EP0601973A1 (fr)	1994-06-15	HALS phosphites et HALS phosphonites comme stabilisateurs
EP0677529A1 (fr)	1995-10-18	HALS phosphites et HALS phosphénites aliphatiques oligomères comme stabilisateurs
EP0042359B1 (fr)	1984-10-31	Monoester monoamide d'acide phosphoneux et des polymers organiques stabilisés les contenant
EP0579576B1 (fr)	1998-05-20	2,4-Dialkyl-6-sec-alkylphénols
JPH02209843A (ja)	1990-08-21	有機材料中の酸化防止剤としてのフェノール基含有化合物
US4076690A (en)	1978-02-28	Phosphonates, process for their manufacture and organic materials stabilized therewith
US4288361A (en)	1981-09-08	Substituted oxazolines as stabilizers
EP0553059B1 (fr)	1996-10-09	Nouveaux phosphites de cycloalkylidène bis phénols
JPS6314766A (ja)	1988-01-21	置換３，５―ビス―（メルカプトメチル）―フェノール，その製法及び該化合物を含有する有機材料のための安定剤
DE19513585A1 (de)	1995-10-19	HALS-Phosphite und HALS-Phophoramide als Stabilisatoren
EP0031295B1 (fr)	1983-05-18	Composés organiques antimoine-soufre, leur application comme stabilisateurs pour thermoplastiques contenant du chlore et thermoplastiques ainsi stabilisés
EP0137395B1 (fr)	1987-11-04	4-(Hydroxyphénylthio)-benzoates
NL9300336A (nl)	1993-09-16	Carbonzuuresters van hydroxyfenylalkanolen als stabiliseermiddelen.
EP0240463A2 (fr)	1987-10-07	Aminooxypropionamides substituées
JPH07103113B2 (ja)	1995-11-08	新規トリアゾール誘導体及び該化合物からなる有機ポリマー用安定剤
JPS59134799A (ja)	1984-08-02	ジオキサシレピン及びジオキサシロシン並びに該化合物を含有する安定化組成物