US2989562A - Method of preparing bis (3-dialkylphosphonopropyl) esters - Google Patents
Method of preparing bis (3-dialkylphosphonopropyl) esters Download PDFInfo
- Publication number
- US2989562A US2989562A US23105A US2310560A US2989562A US 2989562 A US2989562 A US 2989562A US 23105 A US23105 A US 23105A US 2310560 A US2310560 A US 2310560A US 2989562 A US2989562 A US 2989562A
- Authority
- US
- United States
- Prior art keywords
- esters
- dialkylphosphonopropyl
- phosphonate
- compounds
- bis
- 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 - Lifetime
Links
- 238000000034 method Methods 0.000 title claims description 11
- 150000002148 esters Chemical class 0.000 title description 9
- 238000002360 preparation method Methods 0.000 claims description 2
- -1 PHOSPHONOPROPYL Chemical class 0.000 description 12
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 150000007513 acids Chemical class 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical group C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 4
- 239000003999 initiator Substances 0.000 description 4
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 4
- WPWHSFAFEBZWBB-UHFFFAOYSA-N 1-butyl radical Chemical group [CH2]CCC WPWHSFAFEBZWBB-UHFFFAOYSA-N 0.000 description 3
- 150000002978 peroxides Chemical class 0.000 description 3
- 125000004437 phosphorous atom Chemical group 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- 238000007342 radical addition reaction Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- DSAYAFZWRDYBQY-UHFFFAOYSA-N 2,5-dimethylhexa-1,5-diene Chemical group CC(=C)CCC(C)=C DSAYAFZWRDYBQY-UHFFFAOYSA-N 0.000 description 1
- YWLXLRUDGLRYDR-ZHPRIASZSA-N 5beta,20-epoxy-1,7beta,10beta,13alpha-tetrahydroxy-9-oxotax-11-ene-2alpha,4alpha-diyl 4-acetate 2-benzoate Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](O)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 YWLXLRUDGLRYDR-ZHPRIASZSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- OJVABJMSSDUECT-UHFFFAOYSA-L berberin sulfate Chemical compound [O-]S([O-])(=O)=O.C1=C2CC[N+]3=CC4=C(OC)C(OC)=CC=C4C=C3C2=CC2=C1OCO2.C1=C2CC[N+]3=CC4=C(OC)C(OC)=CC=C4C=C3C2=CC2=C1OCO2 OJVABJMSSDUECT-UHFFFAOYSA-L 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- XQRLCLUYWUNEEH-UHFFFAOYSA-L diphosphonate(2-) Chemical class [O-]P(=O)OP([O-])=O XQRLCLUYWUNEEH-UHFFFAOYSA-L 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical group C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000009970 fire resistant effect Effects 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000003879 lubricant additive Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 125000005498 phthalate group Chemical class 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- IOVGROKTTNBUGK-SJCJKPOMSA-N ritodrine Chemical compound N([C@@H](C)[C@H](O)C=1C=CC(O)=CC=1)CCC1=CC=C(O)C=C1 IOVGROKTTNBUGK-SJCJKPOMSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229940116351 sebacate Drugs 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
- C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
-
- 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
-
- 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
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon 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
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
- C08K5/5317—Phosphonic compounds, e.g. R—P(:O)(OR')2
- C08K5/5333—Esters of phosphonic acids
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
- C10M2223/065—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds containing sulfur
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/08—Hydraulic fluids, e.g. brake-fluids
Definitions
- This invention relates to'cominthe molecule have ,heretofor e been very diflicultto pre- ""parel'
- An object of the present invention is to provide a P c h r y c mpau con ni WQ'P Q P atoms are'read'ily obtained in good yields.
- An e o je t a t th s ntion i tqprepare a novel group ofcompounds'inwhich polar groups are distributed throughout the molecule.
- a further object is toprepare compounds containing two-phosphorus atoms per molecule for use aswfire resistant, low-temperature plasticizers for polymers'such "as polyvinyl chloride-and for use as functional-fluids.
- diphosphonate compounds of the general Formula I wherein n is an integer from 0 to 8 and R is an alkyl radical, are prepared by the free radical addition of dialkyl phosphonates to diallyl esters of aliphatic dibasic acids, as illustrated in the equation:
- dialkyl phosphonate is exemplified with alkyl radicals such as methyl, ethyl, n-butyl and 2-ethylhexyl, it is considered that the dialkyl phosphonate may contain any alkyl group and that the alkly groups may be different instead of identical as in present examples.
- Diallyl esters of the general formula wherein n is an integer from 0 to 8 were prepared by conventional esterification procedures or by purification of commercial esters.
- diallyl esters of oxalic, malonic, succinic, adipic, azelaic and sebacic zoate (0.0075' mole) were placed in a 200 m1. roundat n e t me. 2. 901.
- The'free radical addition of the phosphonate with the allyl ester is preferably initiated by the use of a peroxide such as t-butyl perbenzoate or benzoyl peroxide or ambisisobutyronitrile with moderate heating of the reaction mixture.
- a peroxide such as t-butyl perbenzoate or benzoyl peroxide or ambisisobutyronitrile with moderate heating of the reaction mixture.
- the preferred initiator in terms of yield "and shortness of reaction time ist-butyl perbenzoate.
- A-reaction temperature of about C. is. a convenient selection in the range of temperatures which may be employed with peroxides. 'When' the temperature is too low the initiator may not decompose at a practicable rate; there-. action will be slow and take an undue amount of time to obtain a practical yield. If the temperature is too high the initiator may: decompose too rapidly.
- reaction is carried out under a layer of inert gas such as nitrogen to prevent the undue formation ofsi'de products, especially-compounds which would interfere with the desired reaction.
- a typical procedure for preparing the compounds of th s invention is as follows: Preparatian o f bisi3-dialkylphosphonopropyl) esters 1 Dialkyl' phosphonate (0.90 mole) and t-buty-l erben bottom.3.-necked flask equipped with a magnetic stirrer, a nitrogen inlet tube, dropping funnel and thermometer. The contents of the flask Were heated to 100 C., with stirring, and diallyl ester (0.15 mole) was added dropwise at a slow rate while the temperature was maintained at about 100 to C. Additional t-butyl perbenzoate (0.0075 mole) was added after 2 hours and 4 hours of elapsed reaction time.
- Total t-butyl perbenzoate added was 2.5 mole percent of the dialkyl phosphonate.
- the addition of diallyl ester was complete after about 5 hours and the solution was stirred for an additional 1% hours at the same temperature.
- the reaction mixture was degassed at l or less mercury pressure to remove the excess phosphonate and other volatiles and then molecularly distilled. (It should be noted that the residue after removal of excess dialkyl phosphonate is essentially the desired product.)
- the main, constant boiling fraction was collected and weighed. Yields were calculated from this weightso that the values listed do not represent all the product.
- the chemical composition of the compounds of this invention imparts fire resistant properties, and in addition to their use as low temperature plasticizers, they are important for use as functional fluids and lubricant additives.
- aryl radicals instead of alkyl radicals on the phosphonates
- other unsaturated diesters such as divinyl, dimethallyl or dicrotyl esters of the dibasic acids
- unsaturated or aromatic dibasic acids such as maleataes or phthalates.
- Example n Ester Yield, -B.P., 1m" 115 percent C./mm.- 16
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL263689D NL263689A (fr) | 1960-04-18 | ||
| US23105A US2989562A (en) | 1960-04-18 | 1960-04-18 | Method of preparing bis (3-dialkylphosphonopropyl) esters |
| DEA37180A DE1145171B (de) | 1960-04-18 | 1961-04-12 | Verfahren zur Herstellung von Bis-Phosphonester organischer Saeuren |
| GB13152/61A GB938108A (en) | 1960-04-18 | 1961-04-12 | Phosphono esters of organic acids |
| FR859001A FR1292428A (fr) | 1960-04-18 | 1961-04-17 | Nouveaux esters bis (dialcoyle phosphonoalcoyle) et bis (diaryle phosphonoalcoyle) des acides organiques, leur procédé de préparation et leurs applications |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US23105A US2989562A (en) | 1960-04-18 | 1960-04-18 | Method of preparing bis (3-dialkylphosphonopropyl) esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2989562A true US2989562A (en) | 1961-06-20 |
Family
ID=21813155
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US23105A Expired - Lifetime US2989562A (en) | 1960-04-18 | 1960-04-18 | Method of preparing bis (3-dialkylphosphonopropyl) esters |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US2989562A (fr) |
| DE (1) | DE1145171B (fr) |
| GB (1) | GB938108A (fr) |
| NL (1) | NL263689A (fr) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3899549A (en) * | 1973-03-10 | 1975-08-12 | Basf Ag | Poly(dialkylphosphonoalkyl)carbamates |
| US4022757A (en) * | 1974-01-17 | 1977-05-10 | Bayer Aktiengesellschaft | Dicarbamic acid diesters containing phosphorus |
| US4024207A (en) * | 1974-07-04 | 1977-05-17 | Societe Nationale Des Poudres Et Explosifs | Diethyl hydroxymethylphosphonate esters, their preparation and use |
| US5023312A (en) * | 1988-07-19 | 1991-06-11 | Erickson Frank L | Meadowfoam oil and meadowfoam oil derivatives as lubricant additives |
| US5302305A (en) * | 1989-02-09 | 1994-04-12 | The Lubrizol Corporation | Carboxylic esters, liquid compositions containing said carboxylic esters and methods of lubricating metal parts |
| EP1964880A1 (fr) | 2007-03-02 | 2008-09-03 | Lanxess Deutschland GmbH | Mousses de polyuréthane sans halogène protégées contres les flammes |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110451599A (zh) * | 2019-08-30 | 2019-11-15 | 东南大学 | 一种通过紫外光活化甲酸去除水体中硝态氮的方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2710301A (en) * | 1952-09-30 | 1955-06-07 | Shell Dev | Phosphorus esters and a process for the preparation of the same |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL145897B (nl) * | 1948-04-12 | Union Carbide Corp | Werkwijze voor het bereiden van korrelvormige wasmiddelen. | |
| US2492994A (en) * | 1948-05-11 | 1950-01-03 | Shell Dev | Bituminous compositions |
| US2753368A (en) * | 1950-11-13 | 1956-07-03 | Shell Dev | Higher alkyl esters of phosphonic acids |
| US2725359A (en) * | 1951-03-07 | 1955-11-29 | Shell Dev | Lubricating oil composition |
| US2770610A (en) * | 1952-10-30 | 1956-11-13 | Monsanto Chemicals | Esters of epoxidized phosphonic acids and halogenated organic materials stabilized therewith |
| US2837481A (en) * | 1955-03-31 | 1958-06-03 | California Research Corp | Metal alkyl phosphonate thickened lubricating oils |
| US2875231A (en) * | 1956-02-14 | 1959-02-24 | Eastman Kodak Co | Catalytic process of reacting a phosphite and lactone |
-
0
- NL NL263689D patent/NL263689A/xx unknown
-
1960
- 1960-04-18 US US23105A patent/US2989562A/en not_active Expired - Lifetime
-
1961
- 1961-04-12 DE DEA37180A patent/DE1145171B/de active Pending
- 1961-04-12 GB GB13152/61A patent/GB938108A/en not_active Expired
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2710301A (en) * | 1952-09-30 | 1955-06-07 | Shell Dev | Phosphorus esters and a process for the preparation of the same |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3899549A (en) * | 1973-03-10 | 1975-08-12 | Basf Ag | Poly(dialkylphosphonoalkyl)carbamates |
| US4022757A (en) * | 1974-01-17 | 1977-05-10 | Bayer Aktiengesellschaft | Dicarbamic acid diesters containing phosphorus |
| US4024207A (en) * | 1974-07-04 | 1977-05-17 | Societe Nationale Des Poudres Et Explosifs | Diethyl hydroxymethylphosphonate esters, their preparation and use |
| US5023312A (en) * | 1988-07-19 | 1991-06-11 | Erickson Frank L | Meadowfoam oil and meadowfoam oil derivatives as lubricant additives |
| US5302305A (en) * | 1989-02-09 | 1994-04-12 | The Lubrizol Corporation | Carboxylic esters, liquid compositions containing said carboxylic esters and methods of lubricating metal parts |
| EP1964880A1 (fr) | 2007-03-02 | 2008-09-03 | Lanxess Deutschland GmbH | Mousses de polyuréthane sans halogène protégées contres les flammes |
| DE102007010160A1 (de) | 2007-03-02 | 2008-09-04 | Lanxess Deutschland Gmbh | Halogenfreie, flammgeschützte Polyurethanschaumstoffe |
| US20080275152A1 (en) * | 2007-03-02 | 2008-11-06 | Lanxess Deutschland Gmbh | Halogen-free, flame-retardant polyurethane foams |
Also Published As
| Publication number | Publication date |
|---|---|
| NL263689A (fr) | |
| GB938108A (en) | 1963-09-25 |
| DE1145171B (de) | 1963-03-14 |
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