GB944726A - The production of tertiary phosphites including new cyclic phosphites - Google Patents
The production of tertiary phosphites including new cyclic phosphitesInfo
- Publication number
- GB944726A GB944726A GB1781/61A GB178161A GB944726A GB 944726 A GB944726 A GB 944726A GB 1781/61 A GB1781/61 A GB 1781/61A GB 178161 A GB178161 A GB 178161A GB 944726 A GB944726 A GB 944726A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phosphite
- tris
- chloropropyl
- alcohol
- phosphites
- 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
- -1 cyclic phosphites Chemical class 0.000 title abstract 16
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical group [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 title abstract 2
- 239000007983 Tris buffer Substances 0.000 abstract 6
- SSMFJUHKXRYPMF-UHFFFAOYSA-N 2-chloropropyl dihydrogen phosphite Chemical compound CC(Cl)COP(O)O SSMFJUHKXRYPMF-UHFFFAOYSA-N 0.000 abstract 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 4
- 238000009835 boiling Methods 0.000 abstract 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- 150000005846 sugar alcohols Polymers 0.000 abstract 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 2
- YYTSGNJTASLUOY-UHFFFAOYSA-N 1-chloropropan-2-ol Chemical compound CC(O)CCl YYTSGNJTASLUOY-UHFFFAOYSA-N 0.000 abstract 2
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 abstract 2
- FTOKYBLHOYVORA-UHFFFAOYSA-N 2-chlorobutan-1-ol Chemical compound CCC(Cl)CO FTOKYBLHOYVORA-UHFFFAOYSA-N 0.000 abstract 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 abstract 2
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 abstract 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 abstract 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 150000002009 diols Chemical class 0.000 abstract 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical group CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 abstract 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 abstract 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 abstract 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 abstract 2
- 150000008301 phosphite esters Chemical group 0.000 abstract 2
- IVDFJHOHABJVEH-UHFFFAOYSA-N pinacol Chemical compound CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 abstract 2
- 239000004014 plasticizer Substances 0.000 abstract 2
- 229920005989 resin Polymers 0.000 abstract 2
- 239000011347 resin Substances 0.000 abstract 2
- 239000003381 stabilizer Substances 0.000 abstract 2
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N 1-Tetradecanol Natural products CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 abstract 1
- DSKYSDCYIODJPC-UHFFFAOYSA-N 2-butyl-2-ethylpropane-1,3-diol Chemical compound CCCCC(CC)(CO)CO DSKYSDCYIODJPC-UHFFFAOYSA-N 0.000 abstract 1
- VZIQXGLTRZLBEX-UHFFFAOYSA-N 2-chloro-1-propanol Chemical compound CC(Cl)CO VZIQXGLTRZLBEX-UHFFFAOYSA-N 0.000 abstract 1
- XCRYZUBWTDJYOO-UHFFFAOYSA-N 2-chlorobutyl dihydrogen phosphite Chemical compound CCC(Cl)COP(O)O XCRYZUBWTDJYOO-UHFFFAOYSA-N 0.000 abstract 1
- MQWCXKGKQLNYQG-UHFFFAOYSA-N 4-methylcyclohexan-1-ol Chemical compound CC1CCC(O)CC1 MQWCXKGKQLNYQG-UHFFFAOYSA-N 0.000 abstract 1
- 229960000541 cetyl alcohol Drugs 0.000 abstract 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 abstract 1
- 150000002334 glycols Chemical class 0.000 abstract 1
- XVEOUOTUJBYHNL-UHFFFAOYSA-N heptane-2,4-diol Chemical compound CCCC(O)CC(C)O XVEOUOTUJBYHNL-UHFFFAOYSA-N 0.000 abstract 1
- AVIYEYCFMVPYST-UHFFFAOYSA-N hexane-1,3-diol Chemical compound CCCC(O)CCO AVIYEYCFMVPYST-UHFFFAOYSA-N 0.000 abstract 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 abstract 1
- 239000002917 insecticide Substances 0.000 abstract 1
- 229940043348 myristyl alcohol Drugs 0.000 abstract 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 abstract 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 abstract 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 abstract 1
- 229940117969 neopentyl glycol Drugs 0.000 abstract 1
- WCVRQHFDJLLWFE-UHFFFAOYSA-N pentane-1,2-diol Chemical compound CCCC(O)CO WCVRQHFDJLLWFE-UHFFFAOYSA-N 0.000 abstract 1
- GTCCGKPBSJZVRZ-UHFFFAOYSA-N pentane-2,4-diol Chemical compound CC(O)CC(C)O GTCCGKPBSJZVRZ-UHFFFAOYSA-N 0.000 abstract 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical group OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 abstract 1
- 229920003023 plastic Polymers 0.000 abstract 1
- 239000004033 plastic Substances 0.000 abstract 1
- XRVCFZPJAHWYTB-UHFFFAOYSA-N prenderol Chemical compound CCC(CC)(CO)CO XRVCFZPJAHWYTB-UHFFFAOYSA-N 0.000 abstract 1
- 229950006800 prenderol Drugs 0.000 abstract 1
- 229940012831 stearyl alcohol Drugs 0.000 abstract 1
- 238000005809 transesterification reaction Methods 0.000 abstract 1
- IAJUERZLKBLICB-UHFFFAOYSA-N tris(2-chlorobutyl) phosphite Chemical compound CCC(Cl)COP(OCC(Cl)CC)OCC(Cl)CC IAJUERZLKBLICB-UHFFFAOYSA-N 0.000 abstract 1
- ZLOPAJAMUJNFFN-UHFFFAOYSA-N tris(2-chloropropyl) phosphite Chemical compound CC(Cl)COP(OCC(C)Cl)OCC(C)Cl ZLOPAJAMUJNFFN-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- 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
- C07F9/65746—Esters of oxyacids of phosphorus the molecule containing more than one cyclic phosphorus atom
-
- 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
- C07F9/65742—Esters of oxyacids of phosphorus non-condensed with carbocyclic rings or heterocyclic rings or ring systems
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
Abstract
A tertiary phosphite is obtained by transesterifying tris 2-chloropropyl phosphite with an alcohol having a higher boiling point than propylene chlorhydrin or by transesterifying tris 2-chlorobutyl phosphite with an alcohol having a higher boiling point than 2-chlorobutanol. The alcohol may be monohydric or polyhydric, e.g. an alkanol or cycloalkanol such as n-hexanol, n-heptanol, n-octanol, 2-ethylhexanol, isoctyl alcohol, octanol-2, 2-methyl-heptanol-2, n-decyl, isodecyl-, lauryl-, myristyl-, cetyl- or stearyl alcohol, cyclohexanol, or methyl cyclohexanol, or a glycol e.g. ethylene-, propylene-, trimethylene-, 1, 2-butylene-, 2, 3-butylene-, 1, 4-butylene-, 1, 3-butylene- or neopentyl-glycol, 1, 6-hexanediol, pinacol, 1, 2-pentanediol, 2-methyl-2, 4-pentanediol, 2-ethyl, 1, 3-hexanediol, 2, 4-pentanediol, 2, 4-heptanediol, 2, 2-diethyl-1, 3-propanediol and 2-ethyl-2-n-butyl 1, 3-propanediol. The transesterification of the tris-2-chloropropyl phosphite can be carried out at from room temperature to the boiling point of propylene chlorhydrin and at atmospheric or sub-atmospheric pressure, preferably the latter, e.g. a pressure of 50 mm or less. Mixed phosphites, e.g. diceryl (or distearyl) 2-chloropropyl phosphite, may be obtained by using less than 3 moles of the monohydric alcohol per mole of tris 2-chloropropyl phosphite. When using a , b or a , g glycols in an amount of one equivalent (or more) of the polyhydric alcohol per equivalent of tris 2-chloropropyl phosphite, e.g. 3 moles of glycol with 2-moles of tris 2-chloropropyl phosphite cyclic phosphites of the general formula: <FORM:0944726/C2/1> are obtained wherein R1, R2, R3, R4, R5 and R6 are hydrogen or C1-C4 alkyl radicals and n is 0 or 1. If less than one equivalent of the diol is used products are formed which still contain a 2-chloropropyl group, thus when reacting one mole of tris 2-chloropropyl phosphite with one mole (or less) of the above diols there are formed products of the general formula: <FORM:0944726/C2/2> wherein R1, R2, R3, R4, R5 and R6 are hydrogen or C1-C4 alkyl and n is 0 or 1. The invention includes per se compounds of the first general formula given above and compounds of the second general formula given above in which n is 1. The products are useful as insecticides and as stabilizers or plasticizers for plastics, e.g. vinyl chloride resins (see Division C3).ALSO:Tertiary phosphite esters obtainable by reacting tris (2-chloropropyl) phosphite with a mono- or polyhydric alcohol having a higher boiling point than 2-chloropropanol or by reacting tris (2-chlorobutyl) phosphite with a mono- or polyhydric alcohol having a higher boilding point than 2-chloro-butanol (see Division C2) are useful as stabilizers and plasticizers for vinyl chloride resins. The tertiary phosphite esters include cyclic phosphites having the general formulae: <FORM:0944726/C3/1> and <FORM:0944726/C3/2> wherein R1, R2, R3, R4, R5 and R6 are hydrogen or C1-C4 alkyl groups and n is 0 or 1.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US4888A US2961454A (en) | 1960-01-27 | 1960-01-27 | Ester interchange |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB944726A true GB944726A (en) | 1963-12-18 |
Family
ID=21713021
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1781/61A Expired GB944726A (en) | 1960-01-27 | 1961-01-16 | The production of tertiary phosphites including new cyclic phosphites |
| GB30398/62A Expired GB943731A (en) | 1960-01-27 | 1961-01-16 | Novel tertiary spiro phosphites and their production |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB30398/62A Expired GB943731A (en) | 1960-01-27 | 1961-01-16 | Novel tertiary spiro phosphites and their production |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US2961454A (en) |
| GB (2) | GB944726A (en) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3189545A (en) * | 1965-06-15 | Lubricating composition | ||
| US3205269A (en) * | 1960-05-10 | 1965-09-07 | Union Carbide Corp | Stabilization of ethers with phosphorous compounds |
| US3047608A (en) * | 1960-09-15 | 1962-07-31 | Weston Chemical Corp | Phosphites |
| US3081331A (en) * | 1961-08-07 | 1963-03-12 | Weston Chemical Corp | Poly phosphorus ester condensates and their preparation |
| US3053878A (en) * | 1961-05-23 | 1962-09-11 | Weston Chemical Corp | Pentaerythritol phosphite esters |
| NL282705A (en) * | 1961-09-01 | |||
| US3153036A (en) * | 1961-09-04 | 1964-10-13 | Bayer Ag | Phosphorous acid esters derived from transesterification of phosphite triesters with mono-, di-, and trisaccharides |
| US3205250A (en) * | 1961-11-20 | 1965-09-07 | Hooker Chemical Corp | 3, 9-alkoxy and 3, 9-chloropropyl-2, 4, 8, 10-tetraoxa-3, 9-phosphospiro (6, 6) hendeanes |
| US3192243A (en) * | 1962-04-10 | 1965-06-29 | Delaware Chemicals Inc | Phosphorous derivatives of pentaerythritol |
| US3201437A (en) * | 1962-06-11 | 1965-08-17 | Union Carbide Corp | Neoalkyl phosphites |
| US3179689A (en) * | 1962-08-28 | 1965-04-20 | Union Carbide Corp | Chloro compounds prepared by reacting a trimethyloalkane and phosphorus trichloride |
| US4290976A (en) * | 1975-03-24 | 1981-09-22 | Borg-Warner Chemicals, Inc. | Process for the preparation of phenol-free phosphites |
| US4064100A (en) * | 1975-07-22 | 1977-12-20 | Weston Chemical Co., Inc. | Friable distearyl pentaerythritol diphosphite |
| DE2633393C3 (en) * | 1976-07-24 | 1980-02-07 | Hoechst Ag, 6000 Frankfurt | Cyclic phosphites of polyalcohols, their manufacture and use |
| JPS53127552A (en) * | 1977-03-14 | 1978-11-07 | Daicel Chem Ind Ltd | Cellulose organic acid ester resin composition |
| US4665211A (en) * | 1985-12-03 | 1987-05-12 | Borg-Warner Chemicals, Inc. | Process for preparing bis(dialkylphenyl) pentaerythritol diphosphites |
| US6451888B1 (en) | 1994-06-01 | 2002-09-17 | General Electric Company | Solid stabilizer composition with improved hydrolytic stability |
| JP4181127B2 (en) * | 2003-01-06 | 2008-11-12 | 帝人化成株式会社 | Method for producing pentaerythritol diphosphonate |
| JP5069436B2 (en) * | 2006-07-24 | 2012-11-07 | 帝人株式会社 | Method for producing aliphatic phosphite |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2883411A (en) * | 1953-06-18 | 1959-04-21 | Union Carbide Corp | Production of heterocyclic phosphoruscontaining compounds |
| US2841608A (en) * | 1956-05-21 | 1958-07-01 | Shea Chemical Corp | Cyclic glycol phosphites |
| US2834798A (en) * | 1957-12-20 | 1958-05-13 | Shea Chemical Corp | Heterocyclic phosphorus compounds |
-
1960
- 1960-01-27 US US4888A patent/US2961454A/en not_active Expired - Lifetime
-
1961
- 1961-01-16 GB GB1781/61A patent/GB944726A/en not_active Expired
- 1961-01-16 GB GB30398/62A patent/GB943731A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| US2961454A (en) | 1960-11-22 |
| GB943731A (en) | 1963-12-04 |
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