CA2138904A1 - Low-flammability copolyamides - Google Patents
Low-flammability copolyamidesInfo
- Publication number
- CA2138904A1 CA2138904A1 CA002138904A CA2138904A CA2138904A1 CA 2138904 A1 CA2138904 A1 CA 2138904A1 CA 002138904 A CA002138904 A CA 002138904A CA 2138904 A CA2138904 A CA 2138904A CA 2138904 A1 CA2138904 A1 CA 2138904A1
- Authority
- CA
- Canada
- Prior art keywords
- copolyamide
- phosphoric acid
- flammability
- flame
- composition according
- 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.)
- Abandoned
Links
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
- C08K5/53—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
- C08K5/5357—Esters of phosphonic acids cyclic
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Fireproofing Substances (AREA)
Abstract
A copolyamide composition which has a reduced flammability and which is transparent includes at least one copolyamide and a flame-retardant additive composed of at least one alkyl phosphoric acid compound which is dissolved in the copolyamide and which is present in an amount effective to reduce flammability. Preferably the at least one alkyl phosphoric acid compound is present in an amount ranging from about 0.5 to about 40.0 weight %, most preferably from about 4.0 to about 10.0 weight %, based on the weight of the copolyamide. These copolyamides attain desired Vo values in the Standard UL Burning Test with even proportionally low amounts of flame-retardant additive.
Preferred alkyl phosphoric acid compounds include an ester of an aliphatic polyol and an alkylated phosphoric acid, and a trimethyl propanol ester of a methyl phosphoric acid.
Preferred alkyl phosphoric acid compounds include an ester of an aliphatic polyol and an alkylated phosphoric acid, and a trimethyl propanol ester of a methyl phosphoric acid.
Description
~ ~, :: : : ::
LOW- Pl.UlMa~ILITY COPOLYAMIDES
. :
R~.'W"~IINI. OP TE~ lNVL llON
1. Fleld of he In~rent$on The invention relates to a copolyamide composition which ha~ a reduced flammability and which is transparent, and method~of producing same, to a molded article produced from the copolyamide composltion, and to use of a flame-retardant additive to reduce flammability of the copolyamide composition and the article molded therefrom. In particular, the invention relates to use of a flame-retardant additive comprised of at least one alkyl phoæphoric acid compound to reduce flammability of the copolyamide com~osition and the articlè molded therefrom.
:
.2. Des~cril~tion of the Related Art Flame-retardant additives for polymers, especially polyamides, are well-known prior art. These include melamine compounds, especially melamine cyanurate, magnesium and aluminum hydroxide, halogenated and especially brominated .
~ organic compounds, especially in combination with heavy metal : :
-.
` : ~
.
salts, and phosphorus alone and in combination with halogen-containing compounds.
These additives are unsuitable for use with transparent polyamide and copolyamide compositions, however, because they are deleterious to the transparency of such composltions and articles molded therefrom.
It is therefore an object of the present invention to provide a transparent, low-flammability copolyamide composltion.
It iB another object of the present invention to provide a transparent, low-flammability article molded from the foregoing transparent, low-flammability copolyamide composition. --It is yet another object of the present invention to .~ .
provide a method of producing a molded article which has reduced fl~mmAhility and which is transparent from the foregoing transparent, low-flammability copolyamide compDs i tion.
It is still another object of the present invention to provLde a method of reducing flammability of a transparent copolyamide and of a molded article which is molded from the foregoing copolyamide composition.
. , - :
~. ... -~138904 O
SUMMA~Y OF THE lN V~ ON
These objects are attained by the present invention which provides a copolyamlde composition which has a reduced flammability and which is transparent. The copolyamide composition comprises at least one copolyamide and a flame-retardant additive comprised of at least one alkyl phosphoric acid compound which is dissolved in the at least one copolyamide and which is present in an amount effective to reduced flammability of the copolyamide composition.
The at least one alkyl phosphoric acid compound is advantageously present in an amount ranging from about 0.5 to about 40.0 weight ~, preferably from about 4.0 to about 10.0 weight ~, based on the weight of the at least- one copolyamide.
The at least one copolyamide is advantageously based on at least one monomer selected from the group consisting of PA
6, PA 11, and PA 12. The at least one copolyamide is preferably based on at least one first monomer selected from the group consisting of (a) aliphatic diamines having from 4 to 12 carbon atoms, ~b) cycloaliphatic diamines having from 7 to 22 carbon atoms, and (c~ aromatic diamines having from 6 to 22 carbon atoms, in combination with at least one second monomer selected from the group consisting of (d) aliphatic dicarboxylic acids havlng from 4 to 36 carbon atoms, (e) cycloaliphatic dicarboxylic acids having from 8 to 24 carbon : , .
~ .. . , .. ~
-213890~
.
atoms, and (f) aromatic dicarboxylic acids having from 8 to 20 carbon atoms. In particular, the at least one copolyamide is a blend of a plurality of copolyamides which are transparent.
The flame-retardant additive is preferably an ester of an aliphatic polyol and an alkylated phosphoric acid, such as a trimethyl propanol ester of a methyl phosphoric acid.
The objects of the present invention are additionally attained by providing a molded article which has reduced flammability, which is transparent, and which is comprised of the foregoing copolyamide composition.
The objects of the present invention are additionally attained by providing a method of producing -a molded article which has reduc~d flammability and which is transparent. The method includes the steps of (a) preparing a copolyamide composition for molding by adding to at least one copolyamide a flame-retardant additive comprised of at least one alkyl phosphoric acid compound which is dissolved in the copolyamide and which is added in an amount effective to reduce flammability; and (b) molding the copolyamide composition to provide the molded article.
The objects of the present invention are additionally attained by reducing flammability of a copolyamide composition or of a molded article which is molded from a copolyamide composition using addition to at least one ~13890~
.
copolyamide a flame-retardant additive comprising at least one alkyl phosphoric acid compound which is dissolved in the copolyamide and which is present in an amount effective to reduce flammability thereof.
DESCRIPTION OF THE PREFERRED EMBODIMENTS
It is a special advantage of the present invention that the copolyamide compositions are characterized by having very little or no migration of the dissolved phosphoric acid compounds. Hence, molded articles made from the copolyamide compositions of the invention have no annoying deposits as have been known to form on prior art molded articles molded from copolyamide compositions containing fla~e-retardant additives previously known and employed in the art.
Another advantage of the present invention is that the mechanlcal properties of the copolyamides or molded articles made from the copolyamides are virtually unchanged by the dissolved flame-retardant additives according to the invention.
It is also especially advantageous that the copolyamides of the invention are already substantially flame-retardant even when modified with additive amounts which are relatively low and range from 4 to 10 weight ~. Transparent copolyamides having from 0.5 to 40 parts by weight of at least one alkyl phosphoric acid compound are suitable to produce reduced flammability according to the present invention. However, an additive amount of 4 weight ~ or more is generally preferred in order to achieve a desirable VO in the Standard UL Burning Test.
For example, a copolyamide composition containing a copolyamide of the type PA 61/MACM T or of the type PA
12/MACM I was prepared and it was determined that 5 weight of the flame-retardant additive was necessary in order to achieve 94 V, in the Standard UL Burning Test. The flame-retardant tested was a trimethyl propanol ester of a methyl phosphoric acid.
Copolyamides that are suitable copolyamides according to the invention are ~hose that are condensed f-~om the monomers of PA 6, PA 11 or PA 12, or aliphatic diamines having from 4 to 12 carbon atoms, cycloaliphatic diamines having from 7 to 22 carbon atoms, or aromatic or araliphatic diamines having from 6 to 22 carbon atoms and aliphatic dicarboxylic acids having from 4 to 36 carbon atoms, cycloaliphatic dicarboxylic acids having from 8 to 24 carbon atoms, and aromatic dicarboxylic acids having from 8 to 20 carbon atoms. The copolyamides may a-so be blends of a plurality of copolyamides or copolyamides with semicrystalline polyamides, as long as they are transparent. The flame-retardant additive suitable or the present invention is at least one alkyl phosphoric acid compound, such as an aliphatic polyol 21389D~
ester of an alkylated phosphoric acid. The trimethyl propanol ester of a methyl phosphoric acid of the formula each of R and Rl is an o o o o P~ ~C-CH2 - o -~!-o-cl~2-c~ 2 ~. alkylgroup having O - CH2~ ¦ I I CH2 _ 0~ I
R R ' R R ' 1~ 2 to 4 C-atoms is a preferred additive. --Molded articles made from the transparent copolyamide compositions of the present invention are transparent and have low-flammability. Moreover, they are not limited in their shape or length, especially since the mechanical properties are not affected by the proportional amounts of flame-retardant additive in the copolyamide. That is, an -additive amount of 4 weigth ~ or more, especially 5 weight to lO weigth ~ is generally preferred in order to achieve a desirable VO in the Standard UL Burning Test, does not affect the value of the mechanical properties.
The invention has been described in detail with re-spect to preferred embodiments, and it will now be apparent from the foregoing to those skilled in the art that changes and modifications may be made without departing from the invention in its broader aspects, and the invention, therefore, as defined in the appended claims is intended to cover all such changes and modifications as fall within the true spirit of the invention.
Concerning to ISO-Standard 1874-1 PA 6I/MACMT is a co-polyamide of hexamethylene/diamine (6), isophthalic acid (I), 3.3'-dimethyl-4.4'-diamino dicyclohexyl methane (MACM) and terephthalic acid (T), while PA 12/MACMI is a copolyamide of dodecanelactam, MACM and I.
LOW- Pl.UlMa~ILITY COPOLYAMIDES
. :
R~.'W"~IINI. OP TE~ lNVL llON
1. Fleld of he In~rent$on The invention relates to a copolyamide composition which ha~ a reduced flammability and which is transparent, and method~of producing same, to a molded article produced from the copolyamide composltion, and to use of a flame-retardant additive to reduce flammability of the copolyamide composition and the article molded therefrom. In particular, the invention relates to use of a flame-retardant additive comprised of at least one alkyl phoæphoric acid compound to reduce flammability of the copolyamide com~osition and the articlè molded therefrom.
:
.2. Des~cril~tion of the Related Art Flame-retardant additives for polymers, especially polyamides, are well-known prior art. These include melamine compounds, especially melamine cyanurate, magnesium and aluminum hydroxide, halogenated and especially brominated .
~ organic compounds, especially in combination with heavy metal : :
-.
` : ~
.
salts, and phosphorus alone and in combination with halogen-containing compounds.
These additives are unsuitable for use with transparent polyamide and copolyamide compositions, however, because they are deleterious to the transparency of such composltions and articles molded therefrom.
It is therefore an object of the present invention to provide a transparent, low-flammability copolyamide composltion.
It iB another object of the present invention to provide a transparent, low-flammability article molded from the foregoing transparent, low-flammability copolyamide composition. --It is yet another object of the present invention to .~ .
provide a method of producing a molded article which has reduced fl~mmAhility and which is transparent from the foregoing transparent, low-flammability copolyamide compDs i tion.
It is still another object of the present invention to provLde a method of reducing flammability of a transparent copolyamide and of a molded article which is molded from the foregoing copolyamide composition.
. , - :
~. ... -~138904 O
SUMMA~Y OF THE lN V~ ON
These objects are attained by the present invention which provides a copolyamlde composition which has a reduced flammability and which is transparent. The copolyamide composition comprises at least one copolyamide and a flame-retardant additive comprised of at least one alkyl phosphoric acid compound which is dissolved in the at least one copolyamide and which is present in an amount effective to reduced flammability of the copolyamide composition.
The at least one alkyl phosphoric acid compound is advantageously present in an amount ranging from about 0.5 to about 40.0 weight ~, preferably from about 4.0 to about 10.0 weight ~, based on the weight of the at least- one copolyamide.
The at least one copolyamide is advantageously based on at least one monomer selected from the group consisting of PA
6, PA 11, and PA 12. The at least one copolyamide is preferably based on at least one first monomer selected from the group consisting of (a) aliphatic diamines having from 4 to 12 carbon atoms, ~b) cycloaliphatic diamines having from 7 to 22 carbon atoms, and (c~ aromatic diamines having from 6 to 22 carbon atoms, in combination with at least one second monomer selected from the group consisting of (d) aliphatic dicarboxylic acids havlng from 4 to 36 carbon atoms, (e) cycloaliphatic dicarboxylic acids having from 8 to 24 carbon : , .
~ .. . , .. ~
-213890~
.
atoms, and (f) aromatic dicarboxylic acids having from 8 to 20 carbon atoms. In particular, the at least one copolyamide is a blend of a plurality of copolyamides which are transparent.
The flame-retardant additive is preferably an ester of an aliphatic polyol and an alkylated phosphoric acid, such as a trimethyl propanol ester of a methyl phosphoric acid.
The objects of the present invention are additionally attained by providing a molded article which has reduced flammability, which is transparent, and which is comprised of the foregoing copolyamide composition.
The objects of the present invention are additionally attained by providing a method of producing -a molded article which has reduc~d flammability and which is transparent. The method includes the steps of (a) preparing a copolyamide composition for molding by adding to at least one copolyamide a flame-retardant additive comprised of at least one alkyl phosphoric acid compound which is dissolved in the copolyamide and which is added in an amount effective to reduce flammability; and (b) molding the copolyamide composition to provide the molded article.
The objects of the present invention are additionally attained by reducing flammability of a copolyamide composition or of a molded article which is molded from a copolyamide composition using addition to at least one ~13890~
.
copolyamide a flame-retardant additive comprising at least one alkyl phosphoric acid compound which is dissolved in the copolyamide and which is present in an amount effective to reduce flammability thereof.
DESCRIPTION OF THE PREFERRED EMBODIMENTS
It is a special advantage of the present invention that the copolyamide compositions are characterized by having very little or no migration of the dissolved phosphoric acid compounds. Hence, molded articles made from the copolyamide compositions of the invention have no annoying deposits as have been known to form on prior art molded articles molded from copolyamide compositions containing fla~e-retardant additives previously known and employed in the art.
Another advantage of the present invention is that the mechanlcal properties of the copolyamides or molded articles made from the copolyamides are virtually unchanged by the dissolved flame-retardant additives according to the invention.
It is also especially advantageous that the copolyamides of the invention are already substantially flame-retardant even when modified with additive amounts which are relatively low and range from 4 to 10 weight ~. Transparent copolyamides having from 0.5 to 40 parts by weight of at least one alkyl phosphoric acid compound are suitable to produce reduced flammability according to the present invention. However, an additive amount of 4 weight ~ or more is generally preferred in order to achieve a desirable VO in the Standard UL Burning Test.
For example, a copolyamide composition containing a copolyamide of the type PA 61/MACM T or of the type PA
12/MACM I was prepared and it was determined that 5 weight of the flame-retardant additive was necessary in order to achieve 94 V, in the Standard UL Burning Test. The flame-retardant tested was a trimethyl propanol ester of a methyl phosphoric acid.
Copolyamides that are suitable copolyamides according to the invention are ~hose that are condensed f-~om the monomers of PA 6, PA 11 or PA 12, or aliphatic diamines having from 4 to 12 carbon atoms, cycloaliphatic diamines having from 7 to 22 carbon atoms, or aromatic or araliphatic diamines having from 6 to 22 carbon atoms and aliphatic dicarboxylic acids having from 4 to 36 carbon atoms, cycloaliphatic dicarboxylic acids having from 8 to 24 carbon atoms, and aromatic dicarboxylic acids having from 8 to 20 carbon atoms. The copolyamides may a-so be blends of a plurality of copolyamides or copolyamides with semicrystalline polyamides, as long as they are transparent. The flame-retardant additive suitable or the present invention is at least one alkyl phosphoric acid compound, such as an aliphatic polyol 21389D~
ester of an alkylated phosphoric acid. The trimethyl propanol ester of a methyl phosphoric acid of the formula each of R and Rl is an o o o o P~ ~C-CH2 - o -~!-o-cl~2-c~ 2 ~. alkylgroup having O - CH2~ ¦ I I CH2 _ 0~ I
R R ' R R ' 1~ 2 to 4 C-atoms is a preferred additive. --Molded articles made from the transparent copolyamide compositions of the present invention are transparent and have low-flammability. Moreover, they are not limited in their shape or length, especially since the mechanical properties are not affected by the proportional amounts of flame-retardant additive in the copolyamide. That is, an -additive amount of 4 weigth ~ or more, especially 5 weight to lO weigth ~ is generally preferred in order to achieve a desirable VO in the Standard UL Burning Test, does not affect the value of the mechanical properties.
The invention has been described in detail with re-spect to preferred embodiments, and it will now be apparent from the foregoing to those skilled in the art that changes and modifications may be made without departing from the invention in its broader aspects, and the invention, therefore, as defined in the appended claims is intended to cover all such changes and modifications as fall within the true spirit of the invention.
Concerning to ISO-Standard 1874-1 PA 6I/MACMT is a co-polyamide of hexamethylene/diamine (6), isophthalic acid (I), 3.3'-dimethyl-4.4'-diamino dicyclohexyl methane (MACM) and terephthalic acid (T), while PA 12/MACMI is a copolyamide of dodecanelactam, MACM and I.
Claims (12)
1. A copolyamide composition which has a reduced flammability and which is transparent, comprising:
at least one copolyamide; and a flame-retardant additive comprised of at least one alkyl phosphoric acid compound which is dissolved in the at least one copolyamide and which is present in an amount effective to reduced flammability of the copolyamide composition.
at least one copolyamide; and a flame-retardant additive comprised of at least one alkyl phosphoric acid compound which is dissolved in the at least one copolyamide and which is present in an amount effective to reduced flammability of the copolyamide composition.
2. The copolyamide composition according to claim 1, wherein the at least one alkyl phosphoric acid compound is present in an amount ranging from about 0.5 to about 40.0 weight % based on the weight of the at least one copolyamide.
3. The copolyamide composition according to claim 1, wherein the at least one alkyl phosphoric acid compound is present in an amount ranging from about 4.0 to about 10.0 weight % based on the weight of the copolyamide.
4. The copolyamide composition according to claim 1, wherein the at least one copolyamide is based on at least one monomer selected from the group consisting of PA 6, PA 11, and PA 12.
5. The copolyamide composition according to claim 1, wherein the at least one copolyamide is based on at least one first monomer selected from the group consisting of (a) aliphatic diamines having from 4 to 12 carbon atoms, (b) cycloaliphatic diamines having from 7 to 22 carbon atoms, and (c) aromatic diamines having from 6 to 22 carbon atoms, in combination with at least one second monomer selected from the group consisting of (d) aliphatic dicarboxylic acids having from 4 to 36 carbon atoms, (e) cycloaliphatic dicarboxylic acids having from 8 to 24 carbon atoms, and (f) aromatic dicarboxylic acids having from 8 to 20 carbon atoms.
6. The copolyamide composition according to claim 1, wherein the at least one copolyamide is a blend of a plurality of copolyamides which are transparent.
7. The copolyamide composition according to claim 1, wherein the flame-retardant additive is an ester of an aliphatic polyol and an alkylated phosphoric acid.
8. The copolyamide composition according to claim 1, wherein the flame-retardant additive is a trimethyl propanol ester of a methyl phosphoric acid of the formula each of R and R1 is an alkylgroup having 2 to 4 C-atoms
9. A molded article which has reduced flammability, which is transparent, and which is comprised of the copolyamide composition of claim 1.
10. A method of producing a molded article which has reduced flammability and which is transparent, comprising:
(a) preparing the copolyamide composition according to claim 1 by adding to at least one copolyamide a flame-retardant additive comprised of at least one alkyl phosphoric acid compound which is dissolved in the copolyamide and which is added in an amount effective to reduce flammability; and (b) molding the copolyamide composition to provide the molded article.
(a) preparing the copolyamide composition according to claim 1 by adding to at least one copolyamide a flame-retardant additive comprised of at least one alkyl phosphoric acid compound which is dissolved in the copolyamide and which is added in an amount effective to reduce flammability; and (b) molding the copolyamide composition to provide the molded article.
11. A method of reducing flammability of a molded article which is molded from the copolyamide composition according to claim 1, the method comprising:
adding to at least one copolyamide a flame-retardant additive comprised of at least one alkyl phosphoric acid compound which is dissolved in the copolyamide and which is present in an amount effective to reduce flammability thereof.
adding to at least one copolyamide a flame-retardant additive comprised of at least one alkyl phosphoric acid compound which is dissolved in the copolyamide and which is present in an amount effective to reduce flammability thereof.
12. A method of reducing flammability of the copolyamide composition according to claim 1, the method comprising:
adding to at least one copolyamide a flame-retardant additive comprised of at least one alkyl phosphoric acid compound of the formula each of R and R1 is an Alkylgroup having 2 to 4 C-atoms which is dissolved in the copolyamide and which is present in an amount of 5 weigth % to 10 weight % to achieve the VO
qualification of Standard UL Burning Test.
adding to at least one copolyamide a flame-retardant additive comprised of at least one alkyl phosphoric acid compound of the formula each of R and R1 is an Alkylgroup having 2 to 4 C-atoms which is dissolved in the copolyamide and which is present in an amount of 5 weigth % to 10 weight % to achieve the VO
qualification of Standard UL Burning Test.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH03840/93-0 | 1993-12-23 | ||
| CH3840/93A CH685499A5 (en) | 1993-12-23 | 1993-12-23 | Flame retardant copolyamides. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2138904A1 true CA2138904A1 (en) | 1995-06-24 |
Family
ID=4264613
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002138904A Abandoned CA2138904A1 (en) | 1993-12-23 | 1994-12-22 | Low-flammability copolyamides |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPH07238223A (en) |
| CA (1) | CA2138904A1 (en) |
| CH (1) | CH685499A5 (en) |
| DE (2) | DE4406857C2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6306941B1 (en) | 1996-09-13 | 2001-10-23 | Basf Aktiengesellschaft | Flame-proof thermoplastic moulding materials |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5859147A (en) * | 1993-12-23 | 1999-01-12 | Ems-Inventa Ag | Amorphous, transparent polyamide compositions and articles having reduced flammability |
| CH685500A5 (en) * | 1993-12-23 | 1995-07-31 | Inventa Ag | Flame retardant polyamides. |
| US6153677A (en) * | 1993-12-23 | 2000-11-28 | Ems-Inventa Ag | Flame-retardant thermoplastic polyamide molding composition and article molded therefrom |
| FR2843121B3 (en) * | 2002-08-02 | 2004-09-10 | Rhodia Chimie Sa | FLAME RETARDANT, PROCESS FOR PREPARING THE SAME AND THE USE THEREOF |
| FR2843122B1 (en) * | 2002-08-02 | 2006-10-27 | Rhodia Chimie Sa | (EN) NOVEL FLAVORING AGENT BASED ON A LIQUID DEFINIENT IMPREGNATED ON A LARGE POROSITY MINERAL OXIDE, PROCESS FOR PREPARING THE SAME AND USE THEREOF. |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3849368A (en) * | 1971-11-15 | 1974-11-19 | Mobil Oil Corp | Fire retardant polymers containing thermally stable cyclic phosphonate esters |
| US3789091A (en) * | 1971-11-15 | 1974-01-29 | Mobil Oil Corp | Cyclic phosphonate esters and their preparation |
-
1993
- 1993-12-23 CH CH3840/93A patent/CH685499A5/en not_active IP Right Cessation
-
1994
- 1994-03-02 DE DE4406857A patent/DE4406857C2/en not_active Revoked
- 1994-12-22 JP JP6320640A patent/JPH07238223A/en active Pending
- 1994-12-22 CA CA002138904A patent/CA2138904A1/en not_active Abandoned
- 1994-12-23 DE DE59409790T patent/DE59409790D1/en not_active Expired - Fee Related
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6306941B1 (en) | 1996-09-13 | 2001-10-23 | Basf Aktiengesellschaft | Flame-proof thermoplastic moulding materials |
Also Published As
| Publication number | Publication date |
|---|---|
| CH685499A5 (en) | 1995-07-31 |
| JPH07238223A (en) | 1995-09-12 |
| DE4406857C2 (en) | 1996-03-28 |
| DE4406857A1 (en) | 1995-06-29 |
| DE59409790D1 (en) | 2001-07-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Dead |