GB1587436A - Permanently stabilized polymers - Google Patents
Permanently stabilized polymers Download PDFInfo
- Publication number
- GB1587436A GB1587436A GB39105/77A GB3910577A GB1587436A GB 1587436 A GB1587436 A GB 1587436A GB 39105/77 A GB39105/77 A GB 39105/77A GB 3910577 A GB3910577 A GB 3910577A GB 1587436 A GB1587436 A GB 1587436A
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- GB
- United Kingdom
- Prior art keywords
- group
- carbon atoms
- radical
- polymer
- parts
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
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- 229920000642 polymer Polymers 0.000 title claims description 77
- 125000004432 carbon atom Chemical group C* 0.000 claims description 128
- -1 alkyl radical Chemical class 0.000 claims description 122
- 229910052739 hydrogen Inorganic materials 0.000 claims description 66
- 239000001257 hydrogen Substances 0.000 claims description 58
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 49
- 150000001875 compounds Chemical class 0.000 claims description 38
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 33
- 150000003254 radicals Chemical class 0.000 claims description 32
- 230000003019 stabilising effect Effects 0.000 claims description 28
- 229910052757 nitrogen Inorganic materials 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 125000002947 alkylene group Chemical group 0.000 claims description 12
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 150000005840 aryl radicals Chemical class 0.000 claims description 10
- 125000000732 arylene group Chemical group 0.000 claims description 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
- 229920002635 polyurethane Polymers 0.000 claims description 10
- 239000004814 polyurethane Substances 0.000 claims description 10
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 7
- 229920001577 copolymer Chemical class 0.000 claims description 7
- 238000007493 shaping process Methods 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 239000004952 Polyamide Substances 0.000 claims description 2
- 239000005038 ethylene vinyl acetate Substances 0.000 claims description 2
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 claims description 2
- 229920002647 polyamide Polymers 0.000 claims description 2
- 229920000515 polycarbonate Polymers 0.000 claims description 2
- 239000004417 polycarbonate Substances 0.000 claims description 2
- 241000605281 Anaplasma phagocytophilum Species 0.000 claims 1
- 239000003381 stabilizer Substances 0.000 description 124
- 239000000243 solution Substances 0.000 description 78
- 239000010408 film Substances 0.000 description 60
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 52
- 150000002431 hydrogen Chemical group 0.000 description 36
- 238000012360 testing method Methods 0.000 description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 25
- 239000000203 mixture Substances 0.000 description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
- 238000000605 extraction Methods 0.000 description 22
- 238000009835 boiling Methods 0.000 description 21
- 239000000975 dye Substances 0.000 description 21
- 239000012948 isocyanate Substances 0.000 description 20
- 150000003053 piperidines Chemical class 0.000 description 18
- 230000006641 stabilisation Effects 0.000 description 18
- 238000005299 abrasion Methods 0.000 description 17
- 238000007792 addition Methods 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 15
- 229920001971 elastomer Polymers 0.000 description 15
- 239000000806 elastomer Substances 0.000 description 15
- 239000007787 solid Substances 0.000 description 15
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 14
- HTVHSOYSKFBUGY-UHFFFAOYSA-N isocyanato(methoxy)methane Chemical compound COCN=C=O HTVHSOYSKFBUGY-UHFFFAOYSA-N 0.000 description 14
- 239000007858 starting material Substances 0.000 description 14
- 239000002904 solvent Substances 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 238000001035 drying Methods 0.000 description 12
- 230000000694 effects Effects 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 238000002844 melting Methods 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidine Chemical compound CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 11
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 10
- 238000004043 dyeing Methods 0.000 description 10
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 9
- 229920000728 polyester Polymers 0.000 description 9
- 238000011282 treatment Methods 0.000 description 9
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 8
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 8
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 8
- XITRBUPOXXBIJN-UHFFFAOYSA-N bis(2,2,6,6-tetramethylpiperidin-4-yl) decanedioate Chemical compound C1C(C)(C)NC(C)(C)CC1OC(=O)CCCCCCCCC(=O)OC1CC(C)(C)NC(C)(C)C1 XITRBUPOXXBIJN-UHFFFAOYSA-N 0.000 description 8
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 8
- 229950011008 tetrachloroethylene Drugs 0.000 description 8
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 7
- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 7
- 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 7
- UWSMKYBKUPAEJQ-UHFFFAOYSA-N 5-Chloro-2-(3,5-di-tert-butyl-2-hydroxyphenyl)-2H-benzotriazole Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC(N2N=C3C=C(Cl)C=CC3=N2)=C1O UWSMKYBKUPAEJQ-UHFFFAOYSA-N 0.000 description 6
- 239000004970 Chain extender Substances 0.000 description 6
- 239000000654 additive Substances 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 238000009987 spinning Methods 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- 239000000980 acid dye Substances 0.000 description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
- 150000004985 diamines Chemical class 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- 229920003225 polyurethane elastomer Polymers 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 5
- DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 210000002268 wool Anatomy 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- BGYHLZZASRKEJE-UHFFFAOYSA-N [3-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]-2,2-bis[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxymethyl]propyl] 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCC(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 BGYHLZZASRKEJE-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 239000004202 carbamide Substances 0.000 description 4
- XLJMAIOERFSOGZ-UHFFFAOYSA-N cyanic acid Chemical compound OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 description 4
- 125000005442 diisocyanate group Chemical group 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- ARZLUCYKIWYSHR-UHFFFAOYSA-N hydroxymethoxymethanol Chemical group OCOCO ARZLUCYKIWYSHR-UHFFFAOYSA-N 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- CGXOAAMIQPDTPE-UHFFFAOYSA-N 1,2,2,6,6-pentamethylpiperidin-4-amine Chemical compound CN1C(C)(C)CC(N)CC1(C)C CGXOAAMIQPDTPE-UHFFFAOYSA-N 0.000 description 3
- CTKXYQMUGQCAQH-UHFFFAOYSA-N 1-ethyl-2,2,6,6-tetramethylpiperidin-4-amine Chemical compound CCN1C(C)(C)CC(N)CC1(C)C CTKXYQMUGQCAQH-UHFFFAOYSA-N 0.000 description 3
- 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 description 3
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- 239000006096 absorbing agent Substances 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- XEVRDFDBXJMZFG-UHFFFAOYSA-N carbonyl dihydrazine Chemical compound NNC(=O)NN XEVRDFDBXJMZFG-UHFFFAOYSA-N 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 3
- 238000005108 dry cleaning Methods 0.000 description 3
- ZHCJJZJPLRFHMH-UHFFFAOYSA-N ethyl n-(methoxymethyl)carbamate Chemical compound CCOC(=O)NCOC ZHCJJZJPLRFHMH-UHFFFAOYSA-N 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 3
- 239000002649 leather substitute Substances 0.000 description 3
- 239000004611 light stabiliser Substances 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 229920003226 polyurethane urea Polymers 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 239000001044 red dye Substances 0.000 description 3
- 230000000717 retained effect Effects 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 230000002195 synergetic effect Effects 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- YAXWOADCWUUUNX-UHFFFAOYSA-N 1,2,2,3-tetramethylpiperidine Chemical class CC1CCCN(C)C1(C)C YAXWOADCWUUUNX-UHFFFAOYSA-N 0.000 description 2
- XULIXFLCVXWHRF-UHFFFAOYSA-N 1,2,2,6,6-pentamethylpiperidine Chemical compound CN1C(C)(C)CCCC1(C)C XULIXFLCVXWHRF-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- AMAMTFYJXKJFBH-UHFFFAOYSA-N 1-benzyl-2,2,6,6-tetramethylpiperidin-4-amine Chemical compound CC1(C)CC(N)CC(C)(C)N1CC1=CC=CC=C1 AMAMTFYJXKJFBH-UHFFFAOYSA-N 0.000 description 2
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- KZDQWJBGWATWKM-UHFFFAOYSA-N 4-hydroxy-2,2,6,6-tetramethylpiperidine-4-carbohydrazide Chemical compound CC1(C)CC(O)(C(=O)NN)CC(C)(C)N1 KZDQWJBGWATWKM-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 101150065749 Churc1 gene Proteins 0.000 description 2
- GHKOFFNLGXMVNJ-UHFFFAOYSA-N Didodecyl thiobispropanoate Chemical compound CCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCC GHKOFFNLGXMVNJ-UHFFFAOYSA-N 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- 102100038239 Protein Churchill Human genes 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000001414 amino alcohols Chemical class 0.000 description 2
- 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 2
- 239000004305 biphenyl Substances 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 125000006267 biphenyl group Chemical group 0.000 description 2
- 235000013877 carbamide Nutrition 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 230000015271 coagulation Effects 0.000 description 2
- 238000005345 coagulation Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 229940113088 dimethylacetamide Drugs 0.000 description 2
- 238000000578 dry spinning Methods 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- LBKPGNUOUPTQKA-UHFFFAOYSA-N ethyl n-phenylcarbamate Chemical compound CCOC(=O)NC1=CC=CC=C1 LBKPGNUOUPTQKA-UHFFFAOYSA-N 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 229920001281 polyalkylene Polymers 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 239000011527 polyurethane coating Substances 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 230000000087 stabilizing effect Effects 0.000 description 2
- 229920001059 synthetic polymer Polymers 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 235000012222 talc Nutrition 0.000 description 2
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 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
- UUEQKILBVWQUCI-UHFFFAOYSA-N (1,2,2,6,6-pentamethylpiperidin-4-yl)urea Chemical compound CN1C(CC(CC1(C)C)NC(=O)N)(C)C UUEQKILBVWQUCI-UHFFFAOYSA-N 0.000 description 1
- RLXQIDNEIUKWPC-UHFFFAOYSA-N (2,2,6,6-tetramethylpiperidin-4-yl)urea Chemical compound CC1(C)CC(NC(N)=O)CC(C)(C)N1 RLXQIDNEIUKWPC-UHFFFAOYSA-N 0.000 description 1
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- 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
- 239000000758 substrate Substances 0.000 description 1
- 239000004291 sulphur dioxide Substances 0.000 description 1
- 235000010269 sulphur dioxide Nutrition 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229940117958 vinyl acetate Drugs 0.000 description 1
- 238000002166 wet spinning Methods 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 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
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3432—Six-membered rings
- C08K5/3435—Piperidines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
- C08F8/32—Introducing nitrogen atoms or nitrogen-containing groups by reaction with amines
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/83—Chemically modified polymers
- C08G18/833—Chemically modified polymers by nitrogen containing compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Hydrogenated Pyridines (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762642461 DE2642461A1 (de) | 1976-09-21 | 1976-09-21 | Permanent stabilisierte polymere |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1587436A true GB1587436A (en) | 1981-04-01 |
Family
ID=5988461
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB39105/77A Expired GB1587436A (en) | 1976-09-21 | 1977-09-20 | Permanently stabilized polymers |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4153596A (enExample) |
| JP (1) | JPS5339385A (enExample) |
| CA (1) | CA1109587A (enExample) |
| DE (1) | DE2642461A1 (enExample) |
| FR (1) | FR2364943A1 (enExample) |
| GB (1) | GB1587436A (enExample) |
| NL (1) | NL7710263A (enExample) |
Families Citing this family (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH626109A5 (enExample) * | 1976-05-11 | 1981-10-30 | Ciba Geigy Ag | |
| DE2862332D1 (en) | 1977-12-30 | 1983-11-10 | Ciba Geigy Ag | Stabilisation of heat-curable metallic enamel paints against the action of light, humidity and oxygen by the addition of polyalkylpiperidine derivatives |
| DE2834455A1 (de) * | 1978-08-05 | 1980-02-28 | Hoechst Ag | Neue harnstoffderivate, ihre herstellung und ihre verwendung als lichtschutzmittel fuer polymere |
| DE3066156D1 (en) * | 1979-06-21 | 1984-02-23 | Ciba Geigy Ag | Polyalkylpiperidyl ureas, their application as stabilizers and polymers thus stabilized |
| US4265805A (en) * | 1980-04-01 | 1981-05-05 | American Cyanamid Company | Polymeric light stabilizers containing tetralkyl piperidine moieties |
| JPS5832642A (ja) * | 1981-08-20 | 1983-02-25 | Adeka Argus Chem Co Ltd | 安定化された合成樹脂組成物 |
| DE3408948C2 (de) * | 1983-03-21 | 1995-07-27 | Sandoz Ag | 4-Amino-polyalkylpiperidinverbindungen |
| DE3630762A1 (de) * | 1985-09-13 | 1987-03-19 | Sandoz Ag | 2,2,6,6-tetraalkylpiperidin-oxalsaeureamide |
| US4895901A (en) * | 1987-05-28 | 1990-01-23 | Ferro Corporation | Polymetic hindered amine light stabilizers |
| US4804717A (en) * | 1987-05-28 | 1989-02-14 | Ferro Corporation | Polymeric hindered amine light stabilizers |
| US4824884A (en) * | 1987-08-12 | 1989-04-25 | Pennwalt Corporation | Cyclic anhydride derivatives of hydrazide functionalized hindered amine light stabilizers |
| US5300545A (en) * | 1987-08-12 | 1994-04-05 | Elf Atochem North America, Inc. | Process for stabilizing polymer compositions against heat or light effects |
| US4983738A (en) * | 1987-08-12 | 1991-01-08 | Atochem North America, Inc. | Reactive hindered amine light stabilizers |
| US5214147A (en) * | 1987-08-12 | 1993-05-25 | Elf Atochem North America, Inc. | Process for preparing reactive hindered amine light stabilizers |
| US4981915A (en) * | 1987-08-12 | 1991-01-01 | Atochem North America, Inc. | Multipurpose polymer bound stabilizers |
| US5101033A (en) * | 1987-08-12 | 1992-03-31 | Atochem North America, Inc. | Process for preparing reactive hindered amine light stabilizers |
| US4863999A (en) * | 1987-08-12 | 1989-09-05 | Pennwalt Corporation | Multipurpose polymer bound stabilizers |
| US5096974A (en) * | 1987-08-12 | 1992-03-17 | Atochem North America, Inc. | Process for preparing multipurpose polymer bound stabilizers and polymer bound stabilizer produced thereby |
| US4882412A (en) * | 1987-11-30 | 1989-11-21 | Eastman Kodak Company | Polyester polymer containing the residue of the UV absorbing benzopyran compound and shaped articles produced therefrom |
| US4892923A (en) * | 1988-02-22 | 1990-01-09 | Eastman Kodak Company | Polyester compositions containing the residue of a naphthopyran compound and shaped articles produced therefrom |
| KR890014686A (ko) * | 1988-03-08 | 1989-10-25 | 나가이 야다로 | 열가소성 메타크릴이미드 그룹-함유 수지 조성물 |
| US4978699A (en) * | 1988-10-24 | 1990-12-18 | Atochem North America, Inc. | Light stabilizing flame retardants |
| US5043372A (en) * | 1989-12-22 | 1991-08-27 | Atochem North America, Inc. | N,N'-hydrocarbylenebis[N-hals-substituted amic acid hydrazides] and their derivatives |
| US5116976A (en) * | 1990-07-17 | 1992-05-26 | Atochem North America, Inc | Hindered amine light stabilizer hydrazides |
| US5132387A (en) * | 1991-01-07 | 1992-07-21 | Elf Atochem North America, Inc. | Hindered amine light stabilizer hydrazides for stabilizing polyurethane, polyurea and polyurethane-polyurea polymers |
| JP3218771B2 (ja) * | 1992-05-13 | 2001-10-15 | 住友化学工業株式会社 | ヒンダードピペリジン化合物による有機材料の安定化および該化合物の製造 |
| US5380828A (en) * | 1993-10-05 | 1995-01-10 | Ciba-Geigy Corporation | Azodicarboxylic acid derivatives containing hindered amine moieties as polymer stabilizers |
| NZ284802A (en) | 1994-04-15 | 1998-01-26 | Basf Ag | Use of 4-amino-2,2,6,6-tetramethyl piperidine derivatives in a process for producing inherently light- and heat-stabilised polyamides |
| US5994264A (en) * | 1995-06-07 | 1999-11-30 | American Trim, Llc | Transfer printing of metal using protective overcoat |
| US5851238A (en) * | 1996-07-31 | 1998-12-22 | Basf Corporation | Photochemically stabilized polyamide compositions |
| US6136433A (en) * | 1997-05-01 | 2000-10-24 | Basf Corporation | Spinning and stability of solution-dyed nylon fibers |
| US5976296A (en) * | 1998-04-27 | 1999-11-02 | American Trim, Llc | Transfer printing of complex objects |
| CN100374881C (zh) * | 1999-12-16 | 2008-03-12 | 旭化成爱美株式会社 | 可长期配戴的软性隐形镜片 |
| EP1184442A1 (en) * | 2000-08-30 | 2002-03-06 | Clariant International Ltd. | Liquid crystal mixture |
| US6620208B2 (en) | 2001-03-30 | 2003-09-16 | Honeywell International Inc. | Wetfast polyamide fiber with high amino end group content |
| US6761974B1 (en) * | 2001-05-04 | 2004-07-13 | Seagate Technology Llc | Polymeric lubricants with improved stability and thin film recording media comprising same |
| DE10125137A1 (de) * | 2001-05-22 | 2002-12-05 | Basf Ag | Polymere Masse |
| WO2003035642A1 (en) * | 2001-10-23 | 2003-05-01 | Council Of Scientific And Industrial Research | Tinuvin p-hindred amine light stabilizer and derivatives thereof, and a process for the preparation thereof |
| US6492518B1 (en) | 2001-10-30 | 2002-12-10 | Council Of Scientific And Industrial Research | Tinuvin P-hindred amine light stabilizer and derivatives thereof |
| US9322958B2 (en) | 2004-08-27 | 2016-04-26 | Coopervision International Holding Company, Lp | Silicone hydrogel contact lenses |
| KR101367538B1 (ko) | 2004-08-27 | 2014-02-26 | 쿠퍼비젼 인터내셔날 홀딩 캄파니, 엘피 | 실리콘 히드로겔 콘택트 렌즈 |
| EP2202260B1 (de) | 2008-12-23 | 2012-12-12 | Ems-Patent Ag | Inhärent stabilisiertes Polyamid-Elastomer sowie Verfahren zu dessen Herstellung |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3640928A (en) * | 1968-06-12 | 1972-02-08 | Sankyo Co | Stabilization of synthetic polymers |
| US3992390A (en) * | 1971-11-30 | 1976-11-16 | Brian Holt | Esters of piperidinols |
| JPS4962543A (enExample) * | 1972-10-20 | 1974-06-18 |
-
1976
- 1976-09-21 DE DE19762642461 patent/DE2642461A1/de not_active Withdrawn
-
1977
- 1977-09-19 NL NL7710263A patent/NL7710263A/xx not_active Application Discontinuation
- 1977-09-19 US US05/834,764 patent/US4153596A/en not_active Expired - Lifetime
- 1977-09-19 CA CA286,985A patent/CA1109587A/en not_active Expired
- 1977-09-20 GB GB39105/77A patent/GB1587436A/en not_active Expired
- 1977-09-21 JP JP11278177A patent/JPS5339385A/ja active Pending
- 1977-09-21 FR FR7728493A patent/FR2364943A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| FR2364943A1 (fr) | 1978-04-14 |
| NL7710263A (nl) | 1978-03-23 |
| DE2642461A1 (de) | 1978-03-30 |
| CA1109587A (en) | 1981-09-22 |
| JPS5339385A (en) | 1978-04-11 |
| FR2364943B1 (enExample) | 1984-03-02 |
| US4153596A (en) | 1979-05-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |