GB927281A - Organic antimony complexes - Google Patents
Organic antimony complexesInfo
- Publication number
- GB927281A GB927281A GB2742458A GB2742458A GB927281A GB 927281 A GB927281 A GB 927281A GB 2742458 A GB2742458 A GB 2742458A GB 2742458 A GB2742458 A GB 2742458A GB 927281 A GB927281 A GB 927281A
- Authority
- GB
- United Kingdom
- Prior art keywords
- antimony
- esters
- tartrate
- dibromopropyl
- alkoxide
- 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
- 150000001462 antimony Chemical class 0.000 title abstract 3
- 150000002148 esters Chemical class 0.000 abstract 14
- 150000004703 alkoxides Chemical class 0.000 abstract 10
- 229910052787 antimony Inorganic materials 0.000 abstract 10
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 abstract 10
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 abstract 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 6
- 229910052794 bromium Inorganic materials 0.000 abstract 6
- 150000001875 compounds Chemical class 0.000 abstract 5
- 239000000203 mixture Substances 0.000 abstract 5
- 239000000654 additive Substances 0.000 abstract 4
- 229910000410 antimony oxide Inorganic materials 0.000 abstract 4
- 125000001246 bromo group Chemical group Br* 0.000 abstract 4
- VTRUBDSFZJNXHI-UHFFFAOYSA-N oxoantimony Chemical compound [Sb]=O VTRUBDSFZJNXHI-UHFFFAOYSA-N 0.000 abstract 4
- 229920000728 polyester Polymers 0.000 abstract 4
- 229920005749 polyurethane resin Polymers 0.000 abstract 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 3
- ACIAHEMYLLBZOI-ZZXKWVIFSA-N Unsaturated alcohol Chemical compound CC\C(CO)=C/C ACIAHEMYLLBZOI-ZZXKWVIFSA-N 0.000 abstract 3
- 235000019445 benzyl alcohol Nutrition 0.000 abstract 3
- -1 bromo alcohols Chemical class 0.000 abstract 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 abstract 3
- 239000003063 flame retardant Substances 0.000 abstract 3
- 229920005989 resin Polymers 0.000 abstract 3
- 239000011347 resin Substances 0.000 abstract 3
- 150000003870 salicylic acids Chemical class 0.000 abstract 3
- 229920006395 saturated elastomer Polymers 0.000 abstract 3
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 abstract 2
- OGRFZEDAMCUTCN-UHFFFAOYSA-N 4-(3,3-dibromopropoxy)-2,3-dihydroxy-4-oxobutanoic acid Chemical compound C(COC(=O)C(C(C(=O)O)O)O)C(Br)Br OGRFZEDAMCUTCN-UHFFFAOYSA-N 0.000 abstract 2
- ZKHJKRQZGJKQKW-UPHRSURJSA-N BrC(CCOC(\C=C/C(=O)O)=O)Br Chemical class BrC(CCOC(\C=C/C(=O)O)=O)Br ZKHJKRQZGJKQKW-UPHRSURJSA-N 0.000 abstract 2
- 229920005830 Polyurethane Foam Polymers 0.000 abstract 2
- 230000000996 additive effect Effects 0.000 abstract 2
- 229940058905 antimony compound for treatment of leishmaniasis and trypanosomiasis Drugs 0.000 abstract 2
- 150000001463 antimony compounds Chemical class 0.000 abstract 2
- GJNSTPMYZQJUGD-UHFFFAOYSA-N bis(2,3-dibromopropyl) 2,3-dihydroxybutanedioate Chemical compound C(=O)(OCC(CBr)Br)C(O)C(O)C(=O)OCC(CBr)Br GJNSTPMYZQJUGD-UHFFFAOYSA-N 0.000 abstract 2
- 238000009835 boiling Methods 0.000 abstract 2
- PCYQQSKDZQTOQG-NXEZZACHSA-N dibutyl (2r,3r)-2,3-dihydroxybutanedioate Chemical compound CCCCOC(=O)[C@H](O)[C@@H](O)C(=O)OCCCC PCYQQSKDZQTOQG-NXEZZACHSA-N 0.000 abstract 2
- 125000005442 diisocyanate group Chemical group 0.000 abstract 2
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 abstract 2
- 239000006260 foam Substances 0.000 abstract 2
- 150000001261 hydroxy acids Chemical class 0.000 abstract 2
- 125000005498 phthalate group Chemical class 0.000 abstract 2
- 239000011496 polyurethane foam Substances 0.000 abstract 2
- 150000003890 succinate salts Chemical class 0.000 abstract 2
- MWIWYLOKNZKHNV-UHFFFAOYSA-K C(=O)(OCC(CBr)Br)C(O)C(O)C(=O)[O-].[Sb+3].BrC(COC(=O)C(O)C(O)C(=O)[O-])CBr.BrC(COC(=O)C(O)C(O)C(=O)[O-])CBr Chemical compound C(=O)(OCC(CBr)Br)C(O)C(O)C(=O)[O-].[Sb+3].BrC(COC(=O)C(O)C(O)C(=O)[O-])CBr.BrC(COC(=O)C(O)C(O)C(=O)[O-])CBr MWIWYLOKNZKHNV-UHFFFAOYSA-K 0.000 abstract 1
- OEKWFJCGEIGCCK-UHFFFAOYSA-N C(=O)(OCC)C(O)C(O)C(=O)OCC.[Sb] Chemical compound C(=O)(OCC)C(O)C(O)C(=O)OCC.[Sb] OEKWFJCGEIGCCK-UHFFFAOYSA-N 0.000 abstract 1
- VZOTVEFYVWBGDG-UHFFFAOYSA-N C(=O)(OCCCC)C(O)C(O)C(=O)OCCCC.[Sb] Chemical compound C(=O)(OCCCC)C(O)C(O)C(=O)OCCCC.[Sb] VZOTVEFYVWBGDG-UHFFFAOYSA-N 0.000 abstract 1
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 abstract 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 abstract 1
- 239000004800 polyvinyl chloride Substances 0.000 abstract 1
- 229920000915 polyvinyl chloride Polymers 0.000 abstract 1
- 238000002360 preparation method Methods 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
- C08K5/59—Arsenic- or antimony-containing 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
- C07F9/90—Antimony compounds
- C07F9/902—Compounds without antimony-carbon linkages
-
- 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
- C08G18/08—Processes
- C08G18/16—Catalysts
- C08G18/22—Catalysts containing metal compounds
- C08G18/227—Catalysts containing metal compounds of antimony, bismuth or arsenic
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polyurethanes Or Polyureas (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
A flame retardant additive for resins, particularly polyvinyl chloride and polyurethane resins, comprises an antimony complex prepared by reacting an antimony trialkoxide with an ester of a hydroxy carboxylic acid (the carboxylic group being that which is esterified), each mole of alkoxide being reacted with 1 to 3 moles of ester. The esters may be mixed esters and may be derived from lactic, malic, tartaric, citric or salicylic acids, while the esterifying alcohol may be a C1-12 saturated or unsaturated alcohol or benzyl alcohol or their halogenated derivatives. The alkoxide may be derived from a C1-5 alkanol. In examples: "antimony dibutyl tartrate" is incorporated in (1) a P.V.C., allyl phthalate, "Epikote" (Registered Trade Mark) 834 mix and (2) a polyester, diisocyanate, dibromopropyl tartrate mix which is processed into a foam. The second Provisional Specification refers to the use of bromine-containing compounds, particularly esters of bromo alcohols with hydroxy acids and also high boiling bromo esters such as dibromopropyl maleates, fumarates, succinates and phthalates as fire-retardant additives for polyurethane resins. Antimony compounds may be used in conjunction with the bromo compounds, e.g. antimony oxide, alkoxides, acylates or mixed alkoxides/acylates or the antimony complexes disclosed above, particularly ones containing bromine when the same compound may provide both the bromine and the antimony. In an example a polyurethane foam is produced by adding diphenylmethane 4,41-diisocyanate to a polyester mix containing di-(2,3-dibromopropyl) tartrate and antimony oxide. Specification 837,696 is referred to.ALSO:An antimony complex is prepared by reacting an antimony trialkoxide with an ester of a hydroxy carboxylic acid (the carboxylic group being that which is esterified), each mole of alkoxide being reacted with 1 to 3 moles of ester. The esters may be mixed esters and may be derived from lactic, malic, tartaric, citric or salicylic acids, while the esterifying alcohol may be a C1\12 saturated or unsaturated alcohol, or benzyl alcohol or their halogenated derivatives. The alkoxide may be derived from a C1-5 alkanol. Examples describe the preparation of compounds designated antimony dibutyl tartrate, antimony diethyl tartrate and antimony 2,3-dibromo-propyl tartrate. The products are used to impart flame retardant properties to resins (see Groups IV(a) and V). Specification 837,696 is referred to.ALSO:A flame retardent additive for resins, particularly foamed polyurethane resins, comprises an antimony complex prepared by reacting an antimony trialkoxide with an ester of a hydroxy carboxylic acid (the carboxylic group being that which is esterified), each mole of alkoxide being reacted with 1 to 3 moles of ester. The esters may be mixed esters and may be derived from lactic malic, tartaric, citric or salicylic acids, while the esterifying alcohol may be a C1-12 saturated or unsaturated alcohol or benzyl alcohol or their halogenated derivatives. The alkoxide may be derived from a C1-5 alkanol. In Example (2) "antimony dibutyl tartrate" is incorporated in a polyester, diisocyanate, dibromopropyl tartrate mix which is processed into a foam. The second Provisional Specification refers to the use of bromine-containing compounds, particularly esters of bromo alcohols with hydroxy acids and also high boiling bromo esters such as dibromopropyl maleates, fumerates, succinates and phthalates as fire-retardent additives for polyurethane resins. Antimony compounds may be used in conjunction with the bromo compounds, e.g. antimony oxide, alkoxides, acylates or mixed alkoxides/acylates or the antimony complexes disclosed above, particularly ones containing bromine when the same compound may provide both the bromine and the antimony. In an example a polyurethane foam is produced by adding diphenylmethane 4, 41-diisocyanate to a polyester mix containing di-(2, 3-dibromopropyl) tartrate and antimony oxide. Specification 837,696 is referred to.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2742458A GB927281A (en) | 1958-08-27 | 1958-08-27 | Organic antimony complexes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2742458A GB927281A (en) | 1958-08-27 | 1958-08-27 | Organic antimony complexes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB927281A true GB927281A (en) | 1963-05-29 |
Family
ID=10259353
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2742458A Expired GB927281A (en) | 1958-08-27 | 1958-08-27 | Organic antimony complexes |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB927281A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3465031A (en) * | 1962-12-13 | 1969-09-02 | Monsanto Chemicals | Flame-retarding agents |
-
1958
- 1958-08-27 GB GB2742458A patent/GB927281A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3465031A (en) * | 1962-12-13 | 1969-09-02 | Monsanto Chemicals | Flame-retarding agents |
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