MXPA96003466A - Mixture of stabilizers from chromine derivatives, phosphites or organic phosphonites yami - Google Patents
Mixture of stabilizers from chromine derivatives, phosphites or organic phosphonites yamiInfo
- Publication number
- MXPA96003466A MXPA96003466A MXPA/A/1996/003466A MX9603466A MXPA96003466A MX PA96003466 A MXPA96003466 A MX PA96003466A MX 9603466 A MX9603466 A MX 9603466A MX PA96003466 A MXPA96003466 A MX PA96003466A
- Authority
- MX
- Mexico
- Prior art keywords
- alkyl
- stabilizers
- mixture
- groups
- organic
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 42
- 239000003381 stabilizer Substances 0.000 title claims abstract description 33
- AQSJGOWTSHOLKH-UHFFFAOYSA-N Phosphite Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 title claims abstract description 15
- LROMFDHROPKFSO-UHFFFAOYSA-N dioxidophosphane Chemical class [O-]P[O-] LROMFDHROPKFSO-UHFFFAOYSA-N 0.000 title claims abstract description 10
- 150000001412 amines Chemical class 0.000 claims abstract description 14
- VZWXIQHBIQLMPN-UHFFFAOYSA-N Chromane Chemical class C1=CC=C2CCCOC2=C1 VZWXIQHBIQLMPN-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229920003023 plastic Polymers 0.000 claims description 21
- 239000004033 plastic Substances 0.000 claims description 21
- 239000011368 organic material Substances 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000004432 carbon atoms Chemical group C* 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 7
- 238000011105 stabilization Methods 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 3
- 125000004430 oxygen atoms Chemical group O* 0.000 claims description 3
- 150000003512 tertiary amines Chemical class 0.000 claims description 3
- 150000003335 secondary amines Chemical class 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 1
- 150000003141 primary amines Chemical class 0.000 claims 1
- -1 isononyl Chemical group 0.000 description 9
- 229920000642 polymer Polymers 0.000 description 7
- 230000001131 transforming Effects 0.000 description 5
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 150000001993 dienes Chemical class 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- 239000002076 α-tocopherol Substances 0.000 description 3
- 235000004835 α-tocopherol Nutrition 0.000 description 3
- 241001483078 Phyto Species 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 229940087168 alpha Tocopherol Drugs 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 239000004922 lacquer Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 150000005673 monoalkenes Chemical class 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920001955 polyphenylene ether Polymers 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 229920000915 polyvinyl chloride Polymers 0.000 description 2
- 239000004800 polyvinyl chloride Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000000087 stabilizing Effects 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 229960000984 tocofersolan Drugs 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- LVTYICIALWPMFW-UHFFFAOYSA-N 1-(2-hydroxypropylamino)propan-2-ol Chemical compound CC(O)CNCC(C)O LVTYICIALWPMFW-UHFFFAOYSA-N 0.000 description 1
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-Amino-2-propanol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 1
- HCOZFPULQBXXSS-UHFFFAOYSA-N 2-(2,5,7,8-tetramethyl-3,4-dihydrochromen-2-yl)ethyl octadecanoate Chemical compound C1=C(C)C(C)=C2OC(CCOC(=O)CCCCCCCCCCCCCCCCC)(C)CCC2=C1C HCOZFPULQBXXSS-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
- FFODZTFGFDDGQQ-UHFFFAOYSA-N 2-methylprop-2-enoic acid;5-phenylpenta-2,4-dienenitrile Chemical compound CC(=C)C(O)=O.N#CC=CC=CC1=CC=CC=C1 FFODZTFGFDDGQQ-UHFFFAOYSA-N 0.000 description 1
- KXYDGGNWZUHESZ-UHFFFAOYSA-N 4-(2,2,4-trimethyl-3H-chromen-4-yl)phenol Chemical class C12=CC=CC=C2OC(C)(C)CC1(C)C1=CC=C(O)C=C1 KXYDGGNWZUHESZ-UHFFFAOYSA-N 0.000 description 1
- MTAZNLWOLGHBHU-UHFFFAOYSA-N Butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-L CHEBI:8154 Chemical class [O-]P([O-])=O ABLZXFCXXLZCGV-UHFFFAOYSA-L 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L Calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 235000001815 DL-alpha-tocopherol Nutrition 0.000 description 1
- 239000011627 DL-alpha-tocopherol Substances 0.000 description 1
- JQVDAXLFBXTEQA-UHFFFAOYSA-N Dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N Diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- PWWSSIYVTQUJQQ-UHFFFAOYSA-N Distearyl thiodipropionate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCCCCCCC PWWSSIYVTQUJQQ-UHFFFAOYSA-N 0.000 description 1
- 239000002656 Distearyl thiodipropionate Substances 0.000 description 1
- 229940102253 ISOPROPANOLAMINE Drugs 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N N-Butylamine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 239000004698 Polyethylene (PE) Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 229920002396 Polyurea Polymers 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 239000002174 Styrene-butadiene Substances 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N Tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- RKBCYCFRFCNLTO-UHFFFAOYSA-N Triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 description 1
- 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 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Tris Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- GVJHHUAWPYXKBD-UHFFFAOYSA-N VITAMIN E Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 1
- 229930003427 Vitamin E Natural products 0.000 description 1
- 229940046009 Vitamin E Drugs 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 1
- 230000003078 antioxidant Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- SXXILWLQSQDLDL-UHFFFAOYSA-N bis(8-methylnonyl) phenyl phosphite Chemical compound CC(C)CCCCCCCOP(OCCCCCCCC(C)C)OC1=CC=CC=C1 SXXILWLQSQDLDL-UHFFFAOYSA-N 0.000 description 1
- NZOUSWWZFYETEV-UHFFFAOYSA-N buta-1,3-diene;ethyl prop-2-enoate;styrene Chemical compound C=CC=C.CCOC(=O)C=C.C=CC1=CC=CC=C1 NZOUSWWZFYETEV-UHFFFAOYSA-N 0.000 description 1
- WWNGFHNQODFIEX-UHFFFAOYSA-N buta-1,3-diene;methyl 2-methylprop-2-enoate;styrene Chemical compound C=CC=C.COC(=O)C(C)=C.C=CC1=CC=CC=C1 WWNGFHNQODFIEX-UHFFFAOYSA-N 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000002537 cosmetic Substances 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
- 229940043276 diisopropanolamine Drugs 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 235000019305 distearyl thiodipropionate Nutrition 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drugs Drugs 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N ethanolamine Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 description 1
- QBKVWLAQSQPTNL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate;styrene Chemical compound CCOC(=O)C(C)=C.C=CC1=CC=CC=C1 QBKVWLAQSQPTNL-UHFFFAOYSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229920001903 high density polyethylene Polymers 0.000 description 1
- 239000004700 high-density polyethylene Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 229920001684 low density polyethylene Polymers 0.000 description 1
- 239000004702 low-density polyethylene Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000006078 metal deactivator Substances 0.000 description 1
- 125000001400 nonyl 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])[H] 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 239000002674 ointment Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920002496 poly(ether sulfone) Polymers 0.000 description 1
- 229920002492 poly(sulfones) Polymers 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- ZUZSFMQBICMDEZ-UHFFFAOYSA-N prop-1-enylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CC=CC1=CC=CC=C1 ZUZSFMQBICMDEZ-UHFFFAOYSA-N 0.000 description 1
- REYJJPSVUYRZGE-UHFFFAOYSA-N stearylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
- 239000011145 styrene acrylonitrile resin Substances 0.000 description 1
- 239000011115 styrene butadiene Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000002195 synergetic Effects 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 150000003712 vitamin E derivatives Chemical class 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N α-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 150000003772 α-tocopherols Chemical class 0.000 description 1
Abstract
The present invention relates to a mixture of stabilizers containing a) one or more chroman derivatives of the general formula (I): b) one or more organic phosphites of the general formula (II): or an organic phosphonite of the formula III c) one or more amines of the general formula IV, wherein the components (a) and (b) are present in a weight ratio of 1: 5 to 1:14 and the component (c) is present in the mixture of stabilizers in an amount of 0.01 to 2.0% in pe
Description
Mixture of stabilizers from chroman derivatives, phosphites or organic fophephites and amines
Description
The present invention relates to a new mixture of stabilizers from chroman derivatives, phosphites or organic phosphonates and amines for the stabilization of organic materials, especially plastics, against the action of light, oxygen and especially against heat .
DE-A 36 34 531 discloses mixtures of stabilizers for the stabilization of plastics and which are composed of chroman derivative (vitamin E, α-tocopherol) and organic phosphites or phosphonites. However, mixtures have the disadvantage that they are not stable either during storage or after incorporation into plastics. Probably due to hydrolysis reactions in the presence of traces of humidity of the air a decrease in the content of chroman derivatives is observed and with it a reduction of the stabilizing action on the plastics.
The object of the present invention is therefore to provide a stable stabilizer mixture.
It was found, now, a mixture of stabilizers composed of
(a) one or more chroman derivatives of the general formula I
wherein R1 means a group of the formula
- (CH2) 3-CH- (CH2) 3-CH- (CH2) 3-CH-CH3, CH3 CH3 CH3
-CHj- CH2- -C-Z, where Z signifies C -C3o-alkyl,
preferably Ci3-Ci9-alkyl,
-CH2CH2-S- (C? -C3o-alkyl), preferably CH2CH2-S- (C8-C20-alkyl), or
(b) one or more organic phosphites of the general formula II OR3 / R20-P ¡II) \ OR4
wherein the radicals R2 to R4 mean each time C2-Ci2 ~ alkyl, preferably Cg-Cn-alkyl, especially Cß-Cι-alkyl, or C 6 -C 8 -aryl, preferably phenyl, and which may be substituted or groups C? -C? 8-alkyl, preferably one to three C4-C? 2-alkyl groups,
or an organic phosphonite of formula III
r or mixtures from phosphites II and phosphonite III and
c) one or more amines of the general formula IV
R6 / R5-N (IV) R7 in which the radicals R5 to R7 each mean hydrogen, C] -Ci8-alkyl, which may be interrupted by up to 5 non-neighboring oxygen atoms or groups of the formula -NR8- and they are substituted by up to 3 hydroxyl groups, meaning R8 hydrogen or C? -C4-alkyl, or represents phenyl which may be substituted by up to 3 C4-Ci8-alkyl groups, with the exception of NH3 as amine IV,
Components (a) and (b) are present in the weight ratio between 1: 5 to 1:14, preferably 1: 6 to 1:10, and the components (c) present in the mixture of stabilizers in one amount of 0.01 to 2.0% by weight, preferably 0.02 to 1.0% by weight, especially 0.03 to 0.5% by weight, with respect to the mixture of (a) + ( b)
Suitable chromanyl derivatives I are, in particular, 2,5,7,8-tetramethyl-2- (2'-stearoyloxyethyl) chroman (R- -CH 2 CH 2 -O-CO-C 17 H 35) and especially α-tocopherols, preferably DL- a-tocopherol (R! = - (CH2) 3-CH (CH3) - (CH2) 3-CH (CH3) - (CH2) 3-C (CH3) 2 >
The organic phosphites II to be used according to the invention are both liquid and crystalline products. As examples of such phosphites may be mentioned:
trisalkylphosphites with preferably long-chain alkyl groups, such as octyl, nonyl, isononyl, decyl or isodecyl groups;
triaryl phosphites with unsubstituted or mono-aryl groups trisubstituted by alkyl groups, such as phenyl, nonylphenyl or 2,4-di-tert. -butylphenyl;
mixed arylalkylphosphites, such as diisodecylphenylphosphite or diphenylpentaeerytriladiphosphite.
The phosphites of the formula II can be synthesized according to known methods, for example, by reaction of PC13 with monovalent or polyvalent alcohols, in the presence of an organic base or with optionally substituted phenols, without solvent at 20 to 250 ° C. The mixed alkylaryl phosphites are prepared, for example, by reaction of triphenyl phosphite with mono- or poly-lens alcohols, in the presence of a basic catalyst, preferably without solvent.
Phosphonite III is known and is commercially available under the name Irgafos® P-EPQ from the company Ciba-Geigy.
The amines IV to be used according to the invention can be primary, secondary amines, preferably tertiary amines.
As examples of such amines are mentioned: butylamine, dibutylamine, tributylamine, tripropylamine, triisopropylamine, octylamine, diisobutylamine or stearylamine.
In addition, amines possessing radicals having 2 to 18 carbon atoms containing hydroxyl groups for R 5 to R 7 are preferred, eg ethanolamine, diethanolamine, triethanolamine, propane-sheet, dipropanolamine, tripropanolamine, isopropanolamine, diisopropanolamine and especially triisopropanolamine.
However, IV amines should not have too high a moisture content, so ammonia (NH) is not appropriate for the mixture of stabilizers of the invention.
The mixture of stabilizers of the invention is excellently suitable for the stabilization of organic materials against the action of light, oxygen and especially heat. It is also suitable as a metal deactivator. The organic material will be added to stabilize at a concentration of 0.05 to 5% by weight, preferably from 0.01 to 2% by weight, especially from 0.05 to 1% by weight, with respect to the organic material, while during its obtaining.
The stabilizer mixture of the invention also represents not only an excellent antioxidant, especially for plastics, but also an effective dispersant for pigments in liquid paints.
Organic materials are understood, for example, as cosmetic preparations, such as ointments and lotions, drug formulations, such as tablets and suppositories, photographic recording materials, especially photographic emulsions, intermediates for plastics and lacquers or lacquers themselves, but especially the plastics themselves.
Another object of the present invention are organic materials stabilized against the action of light of oxygen and, above all, heat, especially plastics, which contain the mixture of stabilizers of the invention in the concentration indicated above.
To mix the mixture of stabilizers of the invention especially with plastics, all known equipment and methods for the incorporation of stabilizers or other additives into polymers can be used.
The mixture of stabilizers of the invention can be used mainly for the stabilization of plastics in their transformation. Such mixtures of stabilizers are added to the plastics during or before the transformation, in order to protect the plastics from decomposition, being able, as is known, to add the actions of different stabilizer systems.
In addition to the stabilizer system of the invention from components (a), (b) and (c), other stabilizing additives may also be incorporated into the plastics, for example the synergistic substances calcium stearate and distearyl thiodipropionate ( S- (CH2CH2-COOCi8H7) 2) known for stabilization purposes, in the usual amounts.
With the stabilizers described, concentrates can also be prepared in combination with plastics, which can then be processed together with the plastics to be stabilized. In the transformation, the concentrates can be advantageous, according to the respective field of application, since the concentrates are easier to handle and dose in the transformation.
As plastics that can be stabilized with the mixture of stabilizers of the invention, there may be mentioned, for example:
polymers of mono and diolefins, such as, for example, low or high density polyethylene, polypropylene, polybut-1-ene, polyisoprene, polybutadiene, as well as copolymers from mono or diolefins or mixtures of the said polymers;
polystyrene and copolymers of styrene or α-methylstyrene with dienes and / or acrylic derivatives, such as, for example, styrene-butadiene, styrene-acrylonitrile (SAN), styrene-ethyl methacrylate, styrene-butadiene-ethyl acrylate, styrene-acrylonitrile -methacrylate, acrylonitrile-butadiene-styrene (ABS) or methyl methacrylate-butadiene-styrene (MBS);
halogen-containing polymers, such as, for example, vinyl polychloride, vinyl polyvinyl chloride, vinylidene polyfluoride, and their copolymers;
polymers deriving from α, β-unsaturated acids and their derivatives, such as wie polyacrylates, polymethacrylates, polyacrylamides and polyacrylonitriles;
polymers derived from unsaturated alcohols and amines or their acrylic or acetal derivatives, eg polyvinyl alcohol and vinyl polyacetate;
Polyurethanes, polyamides, polyureas, polyphenylene ethers, polyesters, polycarbonates, polysulfones, polyethersulfones and polyether ketones.
Plastics which are easy to stabilize are, in particular, thermoplastics, such as polyvinyl chloride, styrene polymers, polyamides, polycarbonates, polyphenylene oxide, polyesters, polyolefins, preferably polyethylene and polypropylene, polyurethanes, and also duroplastics.
For the suitability and effectiveness of the mixture of stabilizers of the invention, it is particularly important, together with the own color and the stability in the transformation, above all, the stability against hydrolysis and the stable content in derivatives of chroman I.
Compared to the mixtures described in DE-A 36 34 531, the stability to hydrolysis, measured on the basis of water absorption, has been considerably improved. This will be illustrated more clearly by the following example.
Example
The absorption was determined in the mixture of stabilizers at 100%. Given a relative humidity of 98% and a temperature of 22 ° C in the desiccator, the increase in weight was determined as a function of storage time.
Mixture 1 1 part by weight of D, L-α-tocopherol, according to the invention, 10 parts by weight of trisnonylphenylphosphine) phyto, 0.05 parts by weight of triisopropanolamine
Mixture 2: 1 part by weight of D, α-tocopherol, (comparative according to 10 parts by weight of trisnonilfenilfosla DE-A 36 34 531) phyto
The results are represented in the following table.
Mixture No. Absorption of water in% by weight after 0 5 10 15 20 days 1 0 0.05 0.08 0.10 0.11 2 0 2.50 3.20 5.40 8.80
Claims (1)
- CLAIMS: Mix of stabilizers containing (a) one or more chroman derivatives of the general formula I wherein R1 means a group of the formula - (CH2) 3-CH- (CH2) 3-CH- (CH2) 3-CH-CH3, CH3 CH3 CH3 -CH2-CH2-O-C-Z, where Z means C -C3o-alkyl, O -CH CH2-S- (Ci- a C3o-alkyl) (b) one or more organic phosphites of the general formula II .OR3 / R20-P (II) \ OR4 wherein the radicals R 2 to R 4 represent in each case alkyl with 2 to 12 carbon atoms or aryl with 6 to 18 carbon atoms which may be substituted by alkyl groups with 1 to 18 carbon atoms, or an organic phosphonite of formula III or mixtures from phosphites II and phosphonite III, and c) one or more amines of the general formula IV R6 / R5-N (IV) R7 wherein the radicals R5 to R7 each mean hydrogen, alkyl having 1 to 18 carbon atoms which may be interrupted by up to 5 non-neighboring oxygen atoms or groups of the formula -NR8- and which may be substituted by up to 3 groups hydroxyl, R8 being hydrogen or alkyl having 1 to 4 carbon atoms, or phenyl which may be substituted by up to 3 alkyl groups having 4 to 18 carbon atoms, with the exception of NH3 as amine IV, Components (a) and (b) are present in a weight ratio of 1: 5 to 1:14 relative to each other and the component '(c) is present in the mixture of stabilizers in an amount of 0.01 to 2.0. % in weigh. Mixture of stabilizers according to claim 1, wherein "tertiary amines are used as component (c). A stabilizer mixture according to claim 1, wherein as component (c) primary, secondary or tertiary amines are used with alkyl radicals of 2 to 18 carbon atoms containing hydroxyl groups for R5 to R7. Use of mixtures of stabilizers according to claims 1 to 3 for the stabilization of organic materials against the action of light, oxygen and heat. Use of mixtures of stabilizers according to claims 1 to 3 for the stabilization of plastics against the action of light, oxygen and heat. Organic materials stabilized against the action of light, oxygen and heat and containing 0.005 to 5.0% by weight, based on the amount of the organic material, of the mixture of stabilizers according to claims 1 to 3. Plastics stabilized against the action of light, oxygen and heat and containing 0.005 to 5.0% by weight, with respect to the amount of plastic, of the mixture of stabilizers according to claims 1 to 3. Summary of the Invention Mix of stabilizers for organic materials, especially plastics that is composed of (a) one or more chroman derivatives of the general formula I wherein R1 means a group of the formula - (CH2) 3-CH- (CH2) 3-CH- (CH2) 3-CH-CH3, CH3 CH3 CH3 - CH2- CH2-0-C-Z, where Z means C7-C or -alkyl, -CH2CH2-S- (C? -C3o-alkyl), or (b) one or more organic phosphites of the general formula II OR3 / R'O-P: ID \ OR4 wherein the radicals R2 to R4 mean each time C2-Ci2-alkyl or C6-Ci8-aryl, which may be substituted by C? -Ci8-alkyl groups, or an organic phosphonite of formula III or mixtures from phosphites II and phosphonite III and one or more amines of the general formula IV R6 / R5-N (iv) R7 in which the radicals R5 to R7 each mean hydrogen, C? -C? 8-alkyl, which may be interrupted by up to 5 non-neighboring oxygen atoms or groups of the formula -NR8 -, and to be substituted by up to 3 hydroxyl groups, meaning R8 hydrogen or C? -C4-alkyl, or represents phenyl which may be substituted by up to 3 C4-C] 8-alkyl groups, with the exception of NH as amine IV , components (a) and (b) are present in the weight ratio between them from 1: 5 to 1:14, and the components (c) present in the mixture of stabilizers in an amount of 0.01 to 2.0 % by weight with respect to the mixture of (a) + (b).
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP4405670.2 | 1994-02-23 | ||
| DE4405670A DE4405670A1 (en) | 1994-02-23 | 1994-02-23 | Stabilizer mixture of chroman derivatives, organic phosphites or phosphonites and amines |
| PCT/EP1995/000478 WO1995023182A1 (en) | 1994-02-23 | 1995-02-10 | Stabilizer mixture made up of chromane derivatives, organic phosphites or phosphonites and amines |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| MX9603466A MX9603466A (en) | 1997-12-31 |
| MXPA96003466A true MXPA96003466A (en) | 1998-09-18 |
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