GB1076696A - Organic phosphites containing polycyclic aromatic groups and synthetic resin compositions containing the same - Google Patents
Organic phosphites containing polycyclic aromatic groups and synthetic resin compositions containing the sameInfo
- Publication number
- GB1076696A GB1076696A GB4651263A GB4651263A GB1076696A GB 1076696 A GB1076696 A GB 1076696A GB 4651263 A GB4651263 A GB 4651263A GB 4651263 A GB4651263 A GB 4651263A GB 1076696 A GB1076696 A GB 1076696A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- groups
- phosphite
- phosphites
- aryl
- 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
Links
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 title abstract 9
- 239000000203 mixture Substances 0.000 title abstract 4
- 229920003002 synthetic resin Polymers 0.000 title 1
- 239000000057 synthetic resin Substances 0.000 title 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 abstract 19
- -1 cycloalkyl radicals Chemical class 0.000 abstract 14
- 125000003118 aryl group Chemical group 0.000 abstract 13
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 10
- 238000006243 chemical reaction Methods 0.000 abstract 8
- 229920001021 polysulfide Chemical group 0.000 abstract 6
- 229920000915 polyvinyl chloride Polymers 0.000 abstract 6
- 125000000217 alkyl group Chemical group 0.000 abstract 5
- 150000001875 compounds Chemical class 0.000 abstract 5
- 150000002148 esters Chemical class 0.000 abstract 5
- 125000005647 linker group Chemical group 0.000 abstract 5
- 125000003367 polycyclic group Chemical group 0.000 abstract 5
- 229920000642 polymer Polymers 0.000 abstract 5
- 150000003568 thioethers Chemical class 0.000 abstract 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 4
- 125000001931 aliphatic group Chemical group 0.000 abstract 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 4
- 229910052760 oxygen Inorganic materials 0.000 abstract 4
- 239000001301 oxygen Substances 0.000 abstract 4
- 150000003254 radicals Chemical class 0.000 abstract 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- 125000002837 carbocyclic group Chemical group 0.000 abstract 3
- 239000003054 catalyst Substances 0.000 abstract 3
- 229920001577 copolymer Polymers 0.000 abstract 3
- 125000000623 heterocyclic group Chemical group 0.000 abstract 3
- 229920000098 polyolefin Polymers 0.000 abstract 3
- 239000004800 polyvinyl chloride Substances 0.000 abstract 3
- 239000003381 stabilizer Substances 0.000 abstract 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 abstract 2
- 239000004215 Carbon black (E152) Substances 0.000 abstract 2
- 239000004593 Epoxy Substances 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- POKBBTHLULVRMF-UHFFFAOYSA-N OP(O)O.OP(O)O.O.O.O Chemical compound OP(O)O.OP(O)O.O.O.O POKBBTHLULVRMF-UHFFFAOYSA-N 0.000 abstract 2
- 239000004698 Polyethylene Substances 0.000 abstract 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 2
- 230000001476 alcoholic effect Effects 0.000 abstract 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract 2
- 150000001340 alkali metals Chemical class 0.000 abstract 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 2
- 150000001342 alkaline earth metals Chemical class 0.000 abstract 2
- 125000002947 alkylene group Chemical group 0.000 abstract 2
- 125000001118 alkylidene group Chemical group 0.000 abstract 2
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 abstract 2
- 125000000732 arylene group Chemical group 0.000 abstract 2
- 230000015572 biosynthetic process Effects 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 abstract 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 229930195733 hydrocarbon Natural products 0.000 abstract 2
- 239000000178 monomer Substances 0.000 abstract 2
- 125000001624 naphthyl group Chemical group 0.000 abstract 2
- 125000005561 phenanthryl group Chemical group 0.000 abstract 2
- 150000002989 phenols Chemical class 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 229920000573 polyethylene Polymers 0.000 abstract 2
- 125000001725 pyrenyl group Chemical group 0.000 abstract 2
- 230000035484 reaction time Effects 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- 238000005809 transesterification reaction Methods 0.000 abstract 2
- JKTAIYGNOFSMCE-UHFFFAOYSA-N 2,3-di(nonyl)phenol Chemical compound CCCCCCCCCC1=CC=CC(O)=C1CCCCCCCCC JKTAIYGNOFSMCE-UHFFFAOYSA-N 0.000 abstract 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 abstract 1
- 239000004709 Chlorinated polyethylene Substances 0.000 abstract 1
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Chemical compound CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 abstract 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 abstract 1
- 229930040373 Paraformaldehyde Natural products 0.000 abstract 1
- 239000004743 Polypropylene Substances 0.000 abstract 1
- 239000004793 Polystyrene Substances 0.000 abstract 1
- 239000007983 Tris buffer Substances 0.000 abstract 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 abstract 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000002877 alkyl aryl group Chemical group 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 150000005840 aryl radicals Chemical class 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 239000000470 constituent Chemical group 0.000 abstract 1
- 150000001925 cycloalkenes Chemical class 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000002993 cycloalkylene group Chemical group 0.000 abstract 1
- MIHINWMALJZIBX-UHFFFAOYSA-N cyclohexa-2,4-dien-1-ol Chemical compound OC1CC=CC=C1 MIHINWMALJZIBX-UHFFFAOYSA-N 0.000 abstract 1
- 230000001419 dependent effect Effects 0.000 abstract 1
- 235000011087 fumaric acid Nutrition 0.000 abstract 1
- 150000002238 fumaric acids Chemical class 0.000 abstract 1
- 159000000011 group IA salts Chemical class 0.000 abstract 1
- 229920001519 homopolymer Polymers 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- 150000002689 maleic acids Chemical class 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000002480 mineral oil Substances 0.000 abstract 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 abstract 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 abstract 1
- YAFOVCNAQTZDQB-UHFFFAOYSA-N octyl diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)(OCCCCCCCC)OC1=CC=CC=C1 YAFOVCNAQTZDQB-UHFFFAOYSA-N 0.000 abstract 1
- 125000000962 organic group Chemical group 0.000 abstract 1
- 235000006408 oxalic acid Nutrition 0.000 abstract 1
- 239000012188 paraffin wax Substances 0.000 abstract 1
- 229920002866 paraformaldehyde Polymers 0.000 abstract 1
- 150000008301 phosphite esters Chemical class 0.000 abstract 1
- 229920001748 polybutylene Polymers 0.000 abstract 1
- 229920000306 polymethylpentene Polymers 0.000 abstract 1
- 229920001155 polypropylene Polymers 0.000 abstract 1
- 229920002223 polystyrene Polymers 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 230000002035 prolonged effect Effects 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 239000011347 resin Substances 0.000 abstract 1
- 229920005989 resin Polymers 0.000 abstract 1
- 239000011342 resin composition Substances 0.000 abstract 1
- 239000000344 soap Substances 0.000 abstract 1
- 235000012424 soybean oil Nutrition 0.000 abstract 1
- 239000003549 soybean oil Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 125000000101 thioether group Chemical group 0.000 abstract 1
- 229920002554 vinyl polymer Polymers 0.000 abstract 1
- IFNXAMCERSVZCV-UHFFFAOYSA-L zinc;2-ethylhexanoate Chemical compound [Zn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O IFNXAMCERSVZCV-UHFFFAOYSA-L 0.000 abstract 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
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/527—Cyclic esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/12—Esters of phosphoric acids with hydroxyaryl compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/141—Esters of phosphorous acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/141—Esters of phosphorous acids
- C07F9/145—Esters of phosphorous acids with hydroxyaryl compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
- C07F9/6574—Esters of oxyacids of phosphorus
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
- C07F9/6574—Esters of oxyacids of phosphorus
- C07F9/65744—Esters of oxyacids of phosphorus condensed with carbocyclic or heterocyclic rings or ring systems
-
- 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
- C08G79/00—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule
- C08G79/02—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule a linkage containing phosphorus
- C08G79/04—Phosphorus linked to oxygen or to oxygen and carbon
-
- 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
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/524—Esters of phosphorous acids, e.g. of H3PO3
-
- 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
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/524—Esters of phosphorous acids, e.g. of H3PO3
- C08K5/526—Esters of phosphorous acids, e.g. of H3PO3 with hydroxyaryl compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L101/00—Compositions of unspecified macromolecular compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Lubricants (AREA)
Abstract
Organic polyphosphite esters have at least one polycarbocyclic aromatic group attached to each phosphite wherein the carbocyclic nuclei are joined by a bivalent linking group other than a direct C-C link between ring carbons, a thioether group or a polysulphide group; and contain at least one aliphatic or cycloaliphatic group in the molecule, preferably also attached to a phosphite group; less than one phenolic -OH per phosphite group being present on the carbocyclic nuclei, and phosphite groups being joined only via the polycarbocyclic groups. The phosphites may have the general formula <FORM:1076696/C3/1> wherein m is an integer of 1 to 20, each Ar which may be the same or different, is a carbocyclic aromatic nucleus, Y is a linking group other than thioether or polysulphide or a direct link between ring carbons, and Z is hyrogen or organic monovalent or bivalent groups satisfying the remaining phosphite oxygen valences. The groups Ar may be substituted by up to four substituent groups, such as halogen, or alkyl, aryl or cycloalkyl radicals up to a total of 60 carbons per polycyclic group, such radicals usually not having more than 18 carbons each, or hydroxy groups, providing that the number of these groups is less than the total number of phosphite groups. The polycarbocyclic group, Ar-Y-Ar, may have from 10 to 60 carbon atoms and may include condensed aromatic rings; constituent groups include phenyl, naphthyl, phenanthryl, anthracenyl, pyrenyl, chrysenyl and fluorenyl. The linking group, Y, may be any bivalent group other than thioether or polysulphide, such as oxygen, C1 to C20 hydrocarbon such as alkylene, alkylidene, arylene, aralkylene, alkarylene or cycloalkene, and may include one or more oxygen or sulphur atoms. Y may also include aromatic groups having phenolic hydroxyl groups, providing such are less in number than the phosphite groups, and such -OH groups may be esterified by additional phosphite. Z may be any mono- or bivalent organic group, and may form a heterocycle with the phosphite group, and can include Ar groups as defined above. The polyphosphite are prepared by transesterification of an aryl, alkyl or alkylaryl phosphite with a polycyclic polyhydric phenol, when the alkyl or aryl radicals are replaced by polycyclic radicals, the reaction being continued until all available phenolic -OH, or at least sufficient thereof that there is below one such -OH per phosphite group, has been esterified. The structure of the product is dependent upon reaction conditions and reactant proportions; high temperatures and prolonged reaction times favour the production of three-dimensional cage-type polymers, and by avoidance of such conditions the reaction is directed to formation of linear polyphosphites as the preferred form. Linear polymers are also encouraged by introducing monovalent chain stoppers into the reaction system, either by use of an alkyl aryl phosphite as a starting material, of which the aryl groups are more easily replaceable by phenol, or, when a tri-aryl phosphite is used, by adding a monohydric phenol or alcohol with the polycyclic phenol. Also phenols which cyclize with the phosphite to form a heterocyclic O- and P-cotaining ring are preferred as producing linear polymers. The reaction is performed under anhydrous conditions, if required in a volatile alcoholic solvent, and preferably with a catalyst such as an alkaline earth- or alkali-metal, or an alkaline compound thereof, at a temperature of 40 DEG to 150 DEG C. Many examples are given, and numerous particular compounds of the invention are specified. Polyolefins and polyvinyl chlorides are stabilized with the polyphosphites or with monomeric phosphites of the general formula <FORM:1076696/C3/2> wherein each Ar represents a carbocyclic aromatic nucleus with no free phenolic -OH groups, and Z and Y are as descrieed above (see Division C2). When used in such compositions, the above proviso to the nature of the group Y does not apply, and hence Y may also be a thioether, or polysulphide group or a direct link between ring carbons. Polyvinyl chlorides include polyvinyl chloride homopolymers, after-chrlorinated polyvinyl chlorides, and copolymers of vinyl chloride with a minor proportion of copolymerizable monomers such as vinyl acetate, maleic or fumaric acids or esters, or styrene, and also mixtures of a major proportion of polyvinyl chloride with other resins such as chlorinated polyethylene or a copolymer of acrylonitrile, butadiene and styrene. The polyvinyl chloride compositions may be rigid or plasticized with di-octyl phthalate, octyl diphenyl phosphate, epoxidized soybean oil, and epoxy higher esters having from 22 to 150 carbon atoms, formed from epoxidization of esters unsaturated in the acid and/or alcohol portions. Other stabilizers may be present, such as metal soaps and various epoxy compounds. Parting agents, such as C12 to C24 aliphatic acids, mineral oils, polyvinyl stearate, polyethylene and paraffin wax may also be present. Polyolefins which are stabilized by the phosphites include polyethylene, polypropylene, polybutylene and higher polyolefins, such as poly(pentene-1), poly(3-methylbutene-1), poly-(4 - methylpentene - 1), polystyrene, and copolymers of the corresponding monomers with each other. Other stabilizers may be present, such as zinc 2-ethyl hexoate.ALSO:The invention comprises organic phosphite or polyphosphite esters wherein there is at least one polycarbocyclic aromatic group attached to each phosphite group, and an aliphatic or cycloaliphatic group in the molecule, preferably also on the phosphite group, with the provisos that the carbocyclic nuclei of the polycarbocyclic group are linked by a bivalent radical other than a direct bond between ring carbons, a direct thioether or a direct polysulphide link; that when a plurality of phosphite groups are present, they are joined only via polycarbocylic groups; and when phenolic hydroxy groups are present, less than one polycarbocyclic group per phosphite group possesses such hydroxy groups. Preferred monomeric phosphites have the general formula <FORM:1076696/C2/1> wherein each Ar represents an aromatic carbocyclic nucleus, having no free phenolic hydroxyls, Z is an aliphatic or cycloaliphatic group, and Y is a bivalent group other than a direct link between the carbons of the Ar groups, or a thioether or polysulphide group. Preferred polymeric phosphites have the structure <FORM:1076696/C2/2> wherein Ar represents an aromatic nucleus, on which may be present a number of free phenolic groups less than the total number of phosphite groups, or up to four other substituents such as halogen, alkyl, aryl, or cycloalkyl up to a total of 60 carbons per polycyclic group (or a total of 18 carbons per Ar group); m is 0 or an integer of 1 to 20; Z represents hydrogen, or monovalent or bivalent organic radicals satisfying the remaining phosphite oxygen valences, and including at least one aliphatic or cycloaliphatic group; and Y is a bivalent linking radical as above. Z may be alkyl, aryl, alkaryl or heterocyclic groups, and can be or include further groups of the type Ar-Y-Ar. The polycarbocyclic groups may comprise condensed or separate aromatic rings, and may include phenyl, naphthyl, phenanthryl, anthracenyl, pyrenyl, chrysenyl, and fluorenyl groups. Bivalent linking groups may be oxygen; C1 to C20 hydrocarbon, such as alkylene, alkylidene, arylene, aralkylene, alkarylene or cycloalkylene, and may include one or more oxygen or sulphur atoms, or may include aromatic groups having phenolic hydroxy substituents, with the proviso that there are less than one such group per phosphite group; such hydroxyls may be esterified by further phosphite groups. The phosphites are prepared by transesterification of aryl, aralkyl or alkyl phosphites with polycyclic polyhydric phenols, the process being carried sufficiently far to take up all available phenolic -OH, or at least enough that there is less than one such -OH per phosphite group. The reaction is directed towards the formation of linear polymers, such being preferred, rather than cage-type three-dimensional polymers, by avoidance of long reaction times and high temperatures, or by inclusion in the reaction system of monovalent chain stoppers (see Division C3). A catalyst is preferably used, such as an alkaline earth- or alkali-metal or an alkaline salt thereof, and the reaction is carried out at a temperature of 40 DEG C., under anhydrous conditions, if required in a volatile alcoholic solvent. Many examples are given for preparing the inventive compounds, and many of these compounds are specified by name. Also an example includes the preparation of 2,6-tris(21-hydroxy-31,5-dinonylbenzyl)-4 -nonylphenol, by reacting nonylphenol, dinonylphenol, and paraformaldehyde in boiling toluene with an oxalic acid catalyst, the said tris-phenol then being used to prepare a phosphite ester. The phosphites and polyphosphites are employed in resin compositions as stabilizers, in which use phosphites similar to those described but wherein the aforesaid proviso regarding the nature of the linking group Y, need not apply (see Division C3).
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US24075462A | 1962-11-28 | 1962-11-28 |
Publications (1)
Publication Number | Publication Date |
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GB1076696A true GB1076696A (en) | 1967-07-19 |
Family
ID=22907818
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB4651263A Expired GB1076696A (en) | 1962-11-28 | 1963-11-25 | Organic phosphites containing polycyclic aromatic groups and synthetic resin compositions containing the same |
Country Status (8)
Country | Link |
---|---|
AT (1) | AT246434B (en) |
BE (1) | BE640568A (en) |
CH (1) | CH508675A (en) |
DE (1) | DE1569380A1 (en) |
ES (1) | ES293917A1 (en) |
GB (1) | GB1076696A (en) |
NL (2) | NL132248C (en) |
SE (1) | SE347738B (en) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1136578A (en) * | 1965-10-22 | 1968-12-11 | Nat Polychemicals Inc | Phosphite-borate stabilizers for rubber polymerizates |
DE2742482C3 (en) * | 1977-09-21 | 1981-10-15 | Demidova, Geb.Rjabova, Valentina M. | Olefin polymer mixture with cyclic organic phosphite compounds as stabilizers |
JPS5699246A (en) * | 1980-01-10 | 1981-08-10 | Adeka Argus Chem Co Ltd | Stabilized synthetic resin composition |
GB2087399B (en) * | 1980-11-17 | 1983-11-02 | Ciba Geigy Ag | Polyol esters of alkylidine-2,2' -bisphenyl cyclic phosphites |
-
0
- NL NL301126D patent/NL301126A/xx unknown
- NL NL132248D patent/NL132248C/xx active
-
1963
- 1963-11-25 GB GB4651263A patent/GB1076696A/en not_active Expired
- 1963-11-27 ES ES293917A patent/ES293917A1/en not_active Expired
- 1963-11-27 DE DE19631569380 patent/DE1569380A1/en active Pending
- 1963-11-28 BE BE640568D patent/BE640568A/xx unknown
- 1963-11-28 CH CH1459263A patent/CH508675A/en not_active IP Right Cessation
- 1963-11-28 SE SE1314963A patent/SE347738B/xx unknown
- 1963-11-28 AT AT953263A patent/AT246434B/en active
Also Published As
Publication number | Publication date |
---|---|
DE1569380A1 (en) | 1970-07-02 |
CH508675A (en) | 1971-06-15 |
NL301126A (en) | |
AT246434B (en) | 1966-04-25 |
ES293917A1 (en) | 1964-04-01 |
SE347738B (en) | 1972-08-14 |
NL132248C (en) | |
BE640568A (en) | 1964-05-28 |
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