AU2001234222A1 - Salt of a melamine condensation product and a phosphorus-containing acid - Google Patents
Salt of a melamine condensation product and a phosphorus-containing acidInfo
- Publication number
- AU2001234222A1 AU2001234222A1 AU2001234222A AU2001234222A AU2001234222A1 AU 2001234222 A1 AU2001234222 A1 AU 2001234222A1 AU 2001234222 A AU2001234222 A AU 2001234222A AU 2001234222 A AU2001234222 A AU 2001234222A AU 2001234222 A1 AU2001234222 A1 AU 2001234222A1
- Authority
- AU
- Australia
- Prior art keywords
- phosphorus
- acid
- salt
- melamine
- condensation product
- 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.)
- Granted
Links
Description
SALT OF A MELAMINE CONDENSATION PRODUCT AND A PHOSPHORUS-CONTAINING ACID
The invention relates to a salt of a melamine condensation product and a phosphorus-containing acid, a method for the preparation of this salt and the use thereof as a flame retardant in flame-retardant polymer compositions.
The use of the combination of a melamine condensation product and a phosphorus compound in flame-retardant polymer compositions is known from NL-B- 1006525. Said patent describes a flame-retardant polyester composition in which a nitrogen-containing compound and a phosphorus-containing compound form the flame- proofing combination. The disadvantage of the polymer composition according to NL-B- 1006525 is that the phosphorus-containing compound and the nitrogen-containing compound must be prepared separately. As the nitrogen-containing compound in NL-B- 1006525 use is made inter alia of melam. However, the preparation of almost pure melam is a multi-step process that is difficult to carry out and economically little attractive, in a first step melamine and a catalyst are used to form a salt of melam and the relevant catalyst. From this salt almost pure melam is to be obtained in a number of subsequent steps. Known catalysts mentioned in the literature are zinc chloride and sulphonic acids such as paratoluene sulphonic acid.
The object of the invention is to obtain a flame retardant on the basis of a melamine condensation product and a phosphorus-containing compound which can be prepared in an economic way in a single process step. In particular the object of the invention is to obtain a flame retardant on the basis of melam and a phosphorus- containing compound which can be prepared in an economic way in one single process step.
It has been found that this object is attained by preparing a phosphorus-containing salt of a melamine condensation product and a phosphorus- containing acid while using a monobasic phosphorus-containing acid as the phosphorus-containing acid. Melam is preferably used as the melamine condensation product.
Monobasic phosphorus-containing acids that are applicable in the present invention are compounds that contain at least a phosphoric acid, phosphonic acid or phosphinic acid group possessing only one acid equivalent.
Examples of phosphoric acid, phosphonic acid or phosphinic acid groups that possess only one acid equivalent are phosphate ester groups that can be
represented by the general formula (I), alkyl phosphonic acid esters that can be represented by the general formula (II) and phosphinic acids that can be represented by the general formula (III):
(R1O-)(R2O-)-P(=O)-OH (I)
(R3O-)R4P(=O)-OH, (II)
R5R6P(=O)-OH, (III)
in which R. up to and including R6 represent substituted or non-substituted alkyl, aryl, cycloalkyl, aralkyl or alkaryl substituents.
Preferably compounds are used that contain groups according to formula (II) and/or formula (III). Examples of suitable phosphinic acids according to formula (III) are ethylmethylphosphinic acid, diethylphosphinic acid, diethylphosphinic acid, a substituted or non-substituted 1 -hydroxydihydrophospholoxide, a substituted or non-substituted 1 -hydroxyphospholane oxide and diphosphinic acids. Diphosphinic acids are compounds with two phosphinic acid groups. Examples of suitable phosphonic acid esters according to formula (II) are the methyl, ethyl and propyl ester of methylphosphonic acid.
The phosphorus-containing salt of the monobasic phosphorus- containing acid and the nitrogen-containing compound comprises at least 50-95 mol% of a melamine condensation product, in particular melam.
In EP-A-363,321 a melamine phosphonate or dimelamine phosphonate is described and applied as a flame retardant in polymer compositions.
The disadvantage of these salts is that it contains melamine, which can sublime during processing into polymer compositions. The method of preparing these salts stated in EP-A-363,321 is not applicable to condensation products of melamine, such as melam, due to the poor solubility of these in water. Applicant has also found that the preparation of the phosphorus- containing salt of a melamine condensation product, in particular melam, can be carried out simply by heating a triazine compound and the monobasic phosphorus- containing acid together to a temperature between 250 and 400°C, preferably between 280°C and 350°C. Suitable triazine compounds are melamine, ammeline and ammelide or mixtures of these. Preferably melamine is used. Impurities such as urea,
dicyanodiamide, guanidine and ureidomelamine can be present without objection.
The quantity of monobasic phosphorus-containing acid used amounts to 0.05-0.5 mole per mole of triazine compound. Preferably, 0.1 -0.5 mole is used. The monobasic phosphorus-containing acid can also be used in the form of its ammonium or melamine salt. When its melamine salt is used, allowance shall be made for the possible participation of the melamine in a condensation reaction, for instance to melam. The quantity of triazine compound metered to the reactor can be reduced accordingly.
The reaction is carried out by heating a mixture comprising a triazine compound and a monobasic phosphorus-containing acid, or the melamine or ammonium salt of it, to around 250-350°C. Preferably the reaction is carried out between 280 and 320°C. Preferably the reaction is carried out in an almost horizontal stirred reactor. During the reaction ammonia is formed, which can be removed by purging the reactor with an inert gas such as for example nitrogen. Besides melam, whether or not in the form of a phosphorus-containing salt, also small quantities of other triazine condensation products, such as for example melem, melon and methon, whether or not in the form of a phosphorus-containing salt can be formed during the reaction. It is also possible for a small part of the monobasic phosphorus-containing acid to be converted to an anhydride compound. If desired the phosphorus-containing salt of the melamine condensation product, in particular melam, can be treated further. This further treatment is preferably scrubbing with water so that a part of the melamine and/or other water-soluble components dissolve and are removed from the phosphorus-containing salt of the melamine condensation product. Applicant has also found that the phosphorus-containing salt of melam according to the invention brings about flame retardancy of polymer compositions.
The polymer composition then comprises, besides the phosphorus- containing salt of the melamine condensation product, in particular melam, at least a polymer. In addition it can comprise reinforcing agents and/or fillers and/or compounds having a synergistic effect for the phosphorus-containing salt of meiam can contain compounds and/or flame-retardant components other than those according to the invention. Also the usual additives can further be present, such as for example heat and UV stabilizers, release agents, flow-promoting agents, plasticisers, lubricants, dispersing agents, dyestuffs and/or pigments, in quantities that are generally applicable
for these additives insofar as the properties are not adversely influenced.
Polymer compositions that can be made flame-retardant with the phosphorus-containing salt of melam, contain polymers that require heat-resistant flame retardants, such as for example polyamides, polyimides, polyesters, polyurethanes and mixtures and blends of these materials.
Examples of polyamides are polyamides and copolyamides which are derived from diamine and dicarboxylic acids and/or of amino carboxylic acids or the corresponding lactams, such as polyamide 4, polyamide 6, polyamide 6/6,4/6, partially aromatic (co)polyamides, for example polyamides based on an aromatic diamine and adipic acid; polyamides prepared from an alkylene diamine and iso-and/or terephthalic acid and copolyamides thereof, etc..
Examples of polyester are polyester, derived from dicarboxylic acids and dialcohols and/or from hydroxycarboxylic acids or the corresponding lactones such as polyethylene terephthalate, polybutylene terephthalate, poly-1 ,4- dimethylolcyclohexane terephthalate, polycaprolacton and copolyesters thereof, etc..
Preferably the phosphorus-containing salt of melam is used in polymer compositions with polyethylene terephthalate and/or polybutylene terephthalate, with polybutylene terephthalate being specially preferred, or with polyamides such as nylon-6, nylon 6,6 or nylon 4,6. If reinforcing agents and/or fillers are used in the polymer composition, the content of these can vary between broad limits and this content is determined in part by the level of mechanical properties that one wants to attain. In general the reinforcing agents content will amount to no more than 50 wt.% of the total polymer composition. Preferably a reinforced polymer composition will contain 5-50 wt.% reinforcing agents, more preferably 15-45 wt.%. Examples of reinforcing agents are mica, clay, talc, glass fibres, aramid fibres and carbon fibres. Different reinforcing agents can be combined. However, glass fibres are preferred.
The flame-retardant property of the polymer composition can be strengthened by the presence of a compound that has synergistic effects for the phosphorus-containing salt of melam. As a consequence the content of the phosphorus-containing salt of melam according to the invention can generally be chosen lower. An example of a compound with a synergistic effect is a chat-forming compound, whether or not in combination with a catalyst promoting the formation of chat. As chat-forming compounds in principle all known substances are eligible that can strengthen the flame-retardant properties of flame-retardant polymer compositions
by means of the formation of chat caused by the fire. Examples of these are phenol resins, epoxy resins, melamine resins, alkyd resins, silicone resins, urethane resins, polyphenylene ether, polyvinyl alcohol, poly (ethylene-co-vinyl) and compounds with at least two hydroxyl groups. Examples of compounds with at least two hydroxyl groups are alcohols with at least two hydroxyl groups, for example pentaerythritol, dipentaerythritol, tripentaerythritol and mixtures of these. The concentration of the chat- forming compound with a synergistic effect for the phosphorus-containing salt of melam is in general between 0 and 30 wt.%. of the total polymer composition
As a catalyst promoting the formation of chat use can be made of, inter alia, metal salts of tungstic acid, a complex acid oxide of tungsten with a metalloid, salts of tin oxide, ammonium sulphamate and/or the dimer thereof. Metal salts of tungstic acid are preferably alkali metal salts of tungstic acid and in particular sodium tungstate. A complex acid oxide of tungsten with a metalloid is understood to be complex acid oxides which are formed from a metalloid such as silicon or phosphorus and tungsten such as silicotungstic acid or phosphotungstic acid. The quantity of catalyst promoting the formation of chat that is used in the polymer composition amounts to 0.1-5 wt%, preferably 0.1-2.5 wt%.
The flame-retardant properties of the phosphorus-containing salt of melam according to the invention can be further strengthened when the polymer composition comprises one or more other flame-retardant components. As flame- retardant component in principle all known flame retardants are eligible. Examples of these are antimony oxides, such as for example antimony trioxide, in combination with halogen compounds; alkaline-earth metal oxides, for example zinc oxide, magnesium oxide; other metal oxides, for example alumina, silica, iron oxide and manganese oxide; metal hydroxides, for example magnesium hydroxide and aluminium hydroxide; nano composites; clay such as for example montmorillonite clay and kaolin clay; treated clay such as clay treated with primary ammonium compounds or with quaternary ammonium compounds or with melamine or with phosphorus-containing compounds; silicon-containing compounds such as for example silicates, organosilicon compounds, aromatic organosilicon compounds and silanes; metal borates, for example hydrated or non-hydrated zinc borate; sulphur-containing compounds such as for example zinc sulphide, ammonium sulphate, ammonium sulphamate and melamine sulphate; phosphorus-containing compounds such as for example phosphates, phosphonates, phosphinates, phosphines, phosphine oxides and phosphites. Examples of phosphates are aromatic orthophosphate esters such as for example tris
(p-cresyl) phosphate and tris (p-tert-buytyl phenyl) phosphate, Fyrolfiex RDP® (AKZO- Nobel) cyclic phosphate esters, tetraphenylbisphenol-A diphosphate, as well as mixtures of the above-mentioned phosphates. Examples of phosphonates are phosphonate esters and mixed phosphonate esters. Further examples of phosphonates are 1 ,3,2-dioxaphosphorinane-5,5-dimethyl-2-phenoxy-2-oxide, polymeric pentaerythrityl phospohonates such as for example poly [3(-9) alkylene- 2,4,8,10-tetraoxa-3,9-diphosphaspiro [5.5] undecane-3,9-dioxide], cyclic phosphonate esters, bicyclic phosphonate esters such as for example pentaerythrityl diphosphonates, the linear or cyclic esters of trimethylolpropane and methylphosphonic acid, such as for example Antiblaze® 1045 LV (Albright&Wilson), cyclic neopentylene pentaerythritol alcohol phosphate. Examples of phosphinates are phosphinate salts such as for example alicylic phosphinate salts and phosphinate esters. Further examples of phosphinates are diphosphinic acids, dimethylphosphinic acid, ethylmethylphosphinic acid, diethylphosphinic acid, and the salts of these acids, such as for example the aluminium salts and the zinc salts. Examples of phosphine oxides are isobutylbis (hydroxyalkyl) phosphine oxide and 1 ,4-diisobutylene-2,3,5,6- tetrahydroxy-1 ,4-diphosphine oxide or 1 ,4-diisobutylene-1 ,4-diphosphoryl-2,3-5,6- tetrahydroxycyclohexane. Further examples of phosphorus-containing compounds are NH1197® (Great Lakes), NH1511® (Great Lakes), NcendX P-30® (Albemarle), Hostaflam OP550® (Clariant), Hostaflam OP910® (Clariant) and Cyagard RF 1204®, Cyagard RF 1241® and Cyagard RF 1243® (Cyagard are products of Cytec Industries). Preferably phosphates, phosphinates and/or phosphonates are used as the phosphorus-containing compound. The content of phosphorus-containing compound can vary between 0 wt.% and 25 wt.% of the total of the flame-retardant mixture. Other known compounds present in flame-retardant compositions, such as the antidrip agent polytetrafluorethylene, can also be present.
The content of other flame-retardant components used in the polymer composition can vary between broad limits but in general is not more than the content of phosphorus-containing salt of melam. The polymer composition according to the invention can be prepared using the conventional techniques that are known in themselves, by for example dry- mixing all or a number of components in a tumbler mixer, followed by melting in a melt mixer, for example a Brabender mixer or a single- or twin-screw extruder or a kneader. Preferably a twin-screw extruder is used. The different components of the polymer composition can be metered
together to the throat of the extruder. They can be also metered to the extruder at different places. A number of the components that may be present, such as for example dyestuffs, stabilizers, the flame-retardant composition, compounds with a synergistic effect for the triazine flame retardant and/or other flame-retardant components, can be added to the polymer for example in the form of a masterbatch.
The flame-retardant polymer composition according to the invention can be processed with techniques known to one skilled in the art, for example injection moulding, to form semi-finished products or final products.
The invention is explained further on the basis of the following examples:
Example 1
In a 4 litre reactor a mixture of 400 g melamine and 170 g ethylmethylphosphinic acid (CH3.) (CH3CH2-) P(= O)-OH) is introduced. The reactor is heated to 290°C in two hours. The ammonia formed is removed by means of a nitrogen gas flow. The reaction mixture is heated for another hour, after which the product is cooled off. According to HPLC analysis the product contains 67 wt.% melam and 1 wt.% melamine. According to elementary analysis the phosphorus content of the product is 9 wt.%, which corresponds to an ethylmethylphosphinic acid content of 0.5.102 mol%.
Example 2
A 4 litre reactor is charged with a mixture of 400 g melamine and 175 g methylmethylphosphonic acid (CH3-) (CH3O-)P(=O)-OH). The reactor is heated to 290°C in two hours. The ammonia formed is removed by means of a nitrogen gas flow.
The reaction mixture is heated for another hour, after which the product is cooled off. According to HPLC analysis the product contains 66 wt.% melam and 2 wt.% melamine. According to elementary analysis the phosphorus content of the product is 9 wt.%, which corresponds to a methylmethylphosphonic acid content of 0.5.102 mol%.
Example 3
A co-rotating twin-screw extruder (Werner & Pfleiderer, type ZSK 30/33) was fed with: 45 parts of polybutylene terephthalate, 30 parts of glass fibre, 25 parts of the product of example 1. The barrel temperature was set to 250°C and the screw speed to 200 revolutions per minute. From the compounds obtained test rods
with a thickness of 1.6 mm were made. A set of test bars was made which was subjected to the UL94 fire test. The fire behaviour classification was VO. The E- modulus of the test bars was 10.0 mPa and the elongation at failure in each case was 2.0% (ISO 527/1 ).
Example 4
A co-rotating twin-screw extruder (Werner & Pfleiderer, type ZSK 30/33) was fed with: 45 parts of polybutylene terephthalate, 30 parts of glass fibre, 8 parts of Antiblaze® 1045 (Albright&Wilson) and 17 parts of the product of example 1. The barrel temperature was set to 250°C and the screw speed to 200 revolutions per minute. From the compounds obtained test bars with a thickness of 1.6 mm were made. A set of test bars was manufactured which was subjected to the UL94 fire test. The fire behaviour classification is VO. The E-modulus of the test bars was 10.3 mPa and the elongation at failure in each case was 2.1% (ISO 527/1 ).
Example 5
A co-rotating twin-screw extruder (Werner & Pfleiderer, type ZSK 30/33) was fed with: 45 parts of polybutylene terephthalate, 30 parts of glass fibre, 8 parts of aluminium ethylmethylphosphinate, 17 parts of the product of example 1. The barrel temperature was set to 250°C and the screw speed to 200 revolutions per minute. From the compounds obtained test bars with a thickness of 1.6 mm were made. A set of test bars was made which was subjected to the UL94 fire test. The fire behaviour classification is VO. The E-modulus of the test bars was 10.3 mPa and the elongation at failure in each case was 2.1 % (ISO 527/1).
Example 6
A small-scale mini-extruder (self-built) was fed with: 75 parts of polybutylene terephthalate and 25 parts of the product of example 2. The barrel temperature was set to 270°C and the screw speed to 100 revolutions per minute. From the compounds obtained test bars with a thickness of 2.0 mm were made. A set of test specimens was made which was subjected to the UL94 fire test. The fire behaviour classification is VO.
Example 7
A small-scale mini-extruder (self-built) was fed with: 75 parts of polyamide-6 and 25 parts of the product of example 2. The barrel temperature was set to 270°C and the screw speed to 100 revolutions per minute. From the compounds obtained test bars with a thickness of 2.0 mm were made. A set of test specimens was made which was subjected to the UL94 fire test. The fire behaviour classification is VO.
Claims (10)
1. Salt of a melamine condensation product and a phosphorus-containing acid, characterised in that a monobasic phosphorus-containing acid is used as the phosphorus-containing acid.
2. Salt according to claim 1 , characterised in that the monobasic phosphorus- containing acid is a compound that at least contains: a phosphoric acid, phosphonic acid or phosphinic acid group which possess only one acid equivalent.
3. Salt according to claims 1 -2, characterised in that alkyl phosphonic acid esters or phosphinic acids are used as the monobasic phosphorus-containing acid.
4. Salt according to claims 1 -3, characterised in that melam is used as melamine condensation product.
5. Method for the preparation of a phosphorus-containing salt of a melamine condensation product, characterised in that a triazine compound and a monobasic phosphorus-containing acid are heated together to a temperature between 250° and 400°C.
6. Method according to claim 5, characterised in that the temperature is between 280°C and 350°C.
7. Method according to claims 5-6, characterised in that melamine, ammeline and/or ammelide are used as the triazine compounds.
8. Method according to claim 7, characterised in that melamine is used as the triazine compound.
9. Method according to claims 5-8, characterised in that use is made of phosphonic acid esters or phosphinic acid as the monobasic phosphorus- containing acid.
10. Polymer composition comprising a salt of a melamine condensation product and a monobasic phosphorus-containing acid.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL1014232 | 2000-01-31 | ||
| NL1014232A NL1014232C2 (en) | 2000-01-31 | 2000-01-31 | Salt of a melamine condensation product and a phosphorus-containing acid. |
| PCT/NL2001/000024 WO2001057051A1 (en) | 2000-01-31 | 2001-01-15 | Salt of a melamine condensation product and a phosphorus-containing acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2001234222A1 true AU2001234222A1 (en) | 2001-10-25 |
| AU2001234222B2 AU2001234222B2 (en) | 2005-10-20 |
Family
ID=19770703
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2001234222A Expired - Fee Related AU2001234222B2 (en) | 2000-01-31 | 2001-01-15 | Salt of a melamine condensation product and a phosphorus-containing acid |
| AU3422201A Pending AU3422201A (en) | 2000-01-31 | 2001-01-15 | Salt of a melamine condensation product and a phosphorus-containing acid |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU3422201A Pending AU3422201A (en) | 2000-01-31 | 2001-01-15 | Salt of a melamine condensation product and a phosphorus-containing acid |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US6730773B2 (en) |
| EP (1) | EP1252168B1 (en) |
| JP (1) | JP4913971B2 (en) |
| KR (1) | KR100725245B1 (en) |
| CN (1) | CN1193031C (en) |
| AT (1) | ATE298756T1 (en) |
| AU (2) | AU2001234222B2 (en) |
| BR (1) | BR0107959A (en) |
| CA (1) | CA2398697A1 (en) |
| DE (1) | DE60111720T2 (en) |
| ES (1) | ES2243449T3 (en) |
| IL (2) | IL150693A0 (en) |
| MX (1) | MXPA02007328A (en) |
| NL (1) | NL1014232C2 (en) |
| TW (1) | TWI263654B (en) |
| WO (1) | WO2001057051A1 (en) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2001254634A1 (en) | 2000-02-11 | 2001-08-20 | Proteosys Ag | Use of neuregulin-beta as an indicator and/or target |
| NL1016340C2 (en) | 2000-10-05 | 2002-04-08 | Dsm Nv | Halogen-free flame-retardant composition and flame-retardant polyamide composition. |
| US20050113496A1 (en) * | 2003-10-03 | 2005-05-26 | Yuji Saga | Flame resistant polyamide resin composition containing phenolic resin and articles made therefrom |
| DE10359816B4 (en) * | 2003-12-19 | 2006-11-16 | Clariant Produkte (Deutschland) Gmbh | Flame retardant stabilizer combination for polyesters and polyamides as well as plastic molding compounds produced therewith |
| US7452159B2 (en) * | 2004-01-14 | 2008-11-18 | Karoleen B. Alexander | Method of making a multi-layered structure for tree well skirt and sidewalks |
| DE102004019716A1 (en) * | 2004-04-20 | 2005-08-04 | Ticona Gmbh | Flame retardant composition useful in polyester or polyamide molding materials comprises a polyhydroxy compound and a phosphinate salt |
| US20080071013A1 (en) * | 2006-07-12 | 2008-03-20 | David Abecassis | Novel thermoplastic pelletizing technology |
| MX340564B (en) | 2007-11-16 | 2016-07-14 | Mind-Nrg Sa | Active soluble post-translationally modified neuregulin isoforms. |
| EP2184958A1 (en) * | 2008-11-11 | 2010-05-12 | DSM IP Assets B.V. | Electronic assembly comprising a socket mounted on a pcb |
| CN101570518B (en) * | 2009-06-12 | 2010-11-17 | 东华大学 | Preparation method for expansion type melamine hypophosphite fire retardant |
| WO2011092194A1 (en) | 2010-01-27 | 2011-08-04 | Ecoatech Gmbh | N-methyl-melaminium salt of monomethylmethane phosphonic acid ester as a flame retardant |
| US8629206B2 (en) | 2011-01-20 | 2014-01-14 | Basf Se | Flame-retardant thermoplastic molding composition |
| WO2012146624A1 (en) | 2011-04-28 | 2012-11-01 | Basf Se | Flame-retardant molding materials |
| US8653168B2 (en) | 2011-05-10 | 2014-02-18 | Basf Se | Flame-retardant thermoplastic molding composition |
| RU2471788C1 (en) * | 2011-07-07 | 2013-01-10 | Лев Давидович Раснецов | Method of producing melamine cyanurate |
| US20160281001A1 (en) | 2013-09-17 | 2016-09-29 | Thor Gmbh | Flame retardant composition |
| WO2015073296A2 (en) | 2013-11-18 | 2015-05-21 | Russo Joseph M | Mixed detergent composition for intake valve deposit control |
| US9752009B2 (en) | 2015-01-26 | 2017-09-05 | Lanxess Solutions Us Inc. | Flame retardant polymer compositions comprising heat treated phosphorus compounds and melam |
| US10273425B2 (en) | 2017-03-13 | 2019-04-30 | Afton Chemical Corporation | Polyol carrier fluids and fuel compositions including polyol carrier fluids |
| US11873461B1 (en) | 2022-09-22 | 2024-01-16 | Afton Chemical Corporation | Extreme pressure additives with improved copper corrosion |
| US11884890B1 (en) | 2023-02-07 | 2024-01-30 | Afton Chemical Corporation | Gasoline additive composition for improved engine performance |
| US11795412B1 (en) | 2023-03-03 | 2023-10-24 | Afton Chemical Corporation | Lubricating composition for industrial gear fluids |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2620715A1 (en) * | 1987-09-18 | 1989-03-24 | Sturtz Georges | Synthetic resin compositions having an improved fire behaviour containing a polyolefin, a phosphorus-containing flame retardant additive in combination with bromine compounds and antimony oxide or else used in combination or combined with a nitrogenous compound and optionally other additives and/or fillers and shaped objects produced from these compositions |
| GB8823482D0 (en) * | 1988-10-06 | 1988-11-16 | Ciba Geigy Ag | Flame retardants |
| GB8823481D0 (en) * | 1988-10-06 | 1988-11-16 | Ciba Geigy Ag | Flame retardant compositions |
| IT1246764B (en) * | 1990-07-11 | 1994-11-26 | Mini Ricerca Scient Tecnolog | SALTS OF TRIAZINIC COMPOUNDS WITH OXYGENATED ACIDS OF PHOSPHORUS AND THEIR USE IN SELF-EXTINGUISHING POLYMERIC COMPOSITIONS |
| IT1246275B (en) * | 1990-09-11 | 1994-11-17 | Mini Ricerca Scient Tecnolog | AMMELINIC COMPOUNDS AND THEIR USE IN SELF-EXTINGUISHING POLYMER COMPOSITIONS |
| BE1008947A3 (en) * | 1994-12-01 | 1996-10-01 | Dsm Nv | Process for the preparation of condensation products of melamine. |
| JP2000119514A (en) * | 1998-10-14 | 2000-04-25 | Mitsubishi Engineering Plastics Corp | Polyamide resin composition |
| NL1006525C2 (en) * | 1997-07-10 | 1999-01-12 | Dsm Nv | Halogen-free flame-retardant thermoplastic polyester composition. |
| NL1009588C2 (en) * | 1998-07-08 | 2000-01-11 | Dsm Nv | Polyphosphate salt of a high condensation 1,3,5-triazine compound, a process for its preparation and use as a flame arrester in polymer compositions. |
| DE19933901A1 (en) * | 1999-07-22 | 2001-02-01 | Clariant Gmbh | Flame retardant combination |
| NL1013105C2 (en) * | 1999-09-21 | 2001-03-22 | Dsm Nv | Flame-retardant mixture. |
-
2000
- 2000-01-31 NL NL1014232A patent/NL1014232C2/en not_active IP Right Cessation
-
2001
- 2001-01-15 AU AU2001234222A patent/AU2001234222B2/en not_active Expired - Fee Related
- 2001-01-15 TW TW090100856A patent/TWI263654B/en not_active IP Right Cessation
- 2001-01-15 CN CNB018043569A patent/CN1193031C/en not_active Expired - Fee Related
- 2001-01-15 CA CA002398697A patent/CA2398697A1/en not_active Abandoned
- 2001-01-15 ES ES01906393T patent/ES2243449T3/en not_active Expired - Lifetime
- 2001-01-15 AU AU3422201A patent/AU3422201A/en active Pending
- 2001-01-15 DE DE60111720T patent/DE60111720T2/en not_active Expired - Lifetime
- 2001-01-15 WO PCT/NL2001/000024 patent/WO2001057051A1/en active IP Right Grant
- 2001-01-15 BR BR0107959-0A patent/BR0107959A/en not_active IP Right Cessation
- 2001-01-15 IL IL15069301A patent/IL150693A0/en active IP Right Grant
- 2001-01-15 US US10/182,075 patent/US6730773B2/en not_active Expired - Fee Related
- 2001-01-15 MX MXPA02007328A patent/MXPA02007328A/en active IP Right Grant
- 2001-01-15 AT AT01906393T patent/ATE298756T1/en active
- 2001-01-15 KR KR1020027009247A patent/KR100725245B1/en not_active IP Right Cessation
- 2001-01-15 EP EP01906393A patent/EP1252168B1/en not_active Expired - Lifetime
- 2001-01-15 JP JP2001557882A patent/JP4913971B2/en not_active Expired - Fee Related
-
2002
- 2002-07-11 IL IL150693A patent/IL150693A/en not_active IP Right Cessation
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