MXPA97003608A - Polim compositions - Google Patents
Polim compositionsInfo
- Publication number
- MXPA97003608A MXPA97003608A MXPA/A/1997/003608A MX9703608A MXPA97003608A MX PA97003608 A MXPA97003608 A MX PA97003608A MX 9703608 A MX9703608 A MX 9703608A MX PA97003608 A MXPA97003608 A MX PA97003608A
- Authority
- MX
- Mexico
- Prior art keywords
- composition according
- acid
- aliphatic
- aromatic
- phosphono
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 27
- 239000002253 acid Substances 0.000 claims abstract description 12
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 12
- 125000003118 aryl group Chemical group 0.000 claims abstract description 12
- 150000002148 esters Chemical class 0.000 claims abstract description 9
- 229920000642 polymer Polymers 0.000 claims abstract description 8
- -1 phosphono-substituted carboxylic acid Chemical class 0.000 claims abstract description 6
- 229920001228 Polyisocyanate Polymers 0.000 claims abstract description 3
- 150000008064 anhydrides Chemical class 0.000 claims abstract description 3
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 3
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 3
- 229920000768 polyamine Polymers 0.000 claims abstract 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 10
- KMDMOMDSEVTJTI-UHFFFAOYSA-N 2-phosphonobutanedioic acid Chemical compound OC(=O)CC(C(O)=O)P(O)(O)=O KMDMOMDSEVTJTI-UHFFFAOYSA-N 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 6
- 229940117969 NEOPENTYL GLYCOL Drugs 0.000 claims description 5
- GRSMWKLPSNHDHA-UHFFFAOYSA-N Naphthalic anhydride Chemical compound C1=CC(C(=O)OC2=O)=C3C2=CC=CC3=C1 GRSMWKLPSNHDHA-UHFFFAOYSA-N 0.000 claims description 4
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 4
- SLCVBVWXLSEKPL-UHFFFAOYSA-N 2,2-dimethylpropane-1,3-diol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims description 3
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Chemical compound C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims description 3
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 2
- 239000001384 succinic acid Substances 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N 1,2-ethanediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims 1
- LRZCOABZEULHCP-UHFFFAOYSA-N cyclohexane;methanol Chemical compound OC.C1CCCCC1 LRZCOABZEULHCP-UHFFFAOYSA-N 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 abstract description 2
- 150000007513 acids Chemical class 0.000 abstract 2
- 239000000126 substance Substances 0.000 abstract 2
- OAICVXFJPJFONN-UHFFFAOYSA-N phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract 1
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- RINCXYDBBGOEEQ-UHFFFAOYSA-N Succinic anhydride Chemical compound O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- 229940014800 succinic anhydride Drugs 0.000 description 2
- VLUVCCZLXWULOB-UHFFFAOYSA-N 2,2-dimethylpropane-1,3-diol;propane-1,2-diol Chemical compound CC(O)CO.OCC(C)(C)CO VLUVCCZLXWULOB-UHFFFAOYSA-N 0.000 description 1
- MTJGVAJYTOXFJH-UHFFFAOYSA-N 3-aminonaphthalene-1,5-disulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C2=CC(N)=CC(S(O)(=O)=O)=C21 MTJGVAJYTOXFJH-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000001804 emulsifying Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229940086735 succinate Drugs 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
Abstract
A polymer composition including phosphorus substituents comprising: (a) a phosphono-substituted carboxylic acid or a ester of said acid, and (b) a mono- or polyfunctional entity polymerizable with (a); substances suitable for use as (a) dicarboxylic acids aliphatic or phosphono-substituted aromatics or esters of these acids; substances suitable for use as (b) are polyhydric alcohols, aliphatic or aromatic mononuclear or polynuclear polycarboxylic acids or esters or anhydrides thereof. They are also suitable for use as (b) aliphatic or aromatic polyamines and aliphatic or aromatic polyisocyanates or polyepoxides
Description
CQflPQSlciES PE PQLIÍ1ERQ
DESCRIPTIVE HEARING
This invention relates to polymer compositions, in particular to polymer compositions including phosphono substituents. In accordance, the present invention provides a polymer composition comprising: (a) a substituted carboxylic acid or an ester of said acid; and (b) a mono or poly functional entity polymerizable with (a). Conveniently, (a) may be a phosphono substituted aliphatic or aromatic dicarboxylic acid or an ester of such an acid, for example phosphono succinic acid or its dimethyl ester. Entity (b) can be a polyhydric alcohol. Conveniently, (b) can be an aliphatic or cycloaliphatic dihydric alcohol, such as ethylene glycol, propylene glycol neopentyl glycol or 1,4-dimethylol-cyclohexane. Alternatively, (b) may be a trihydric alcohol such as glycerol. Again, (b) can be an aliphatic, mononuclear or aromatic polynuclear aromatic polycarboxylic acid, or an ester or anhydride of such an acid.
Therefore, (b) can be succinic acid, terephthalic acid, phthalic anhydride, naphthalic acid or naphthalic anhydride. In addition, (b) can be an aliphatic or aromatic polyarnine (eg ethylendiarnine) or an aromatic or aromatic polyisocyanate or a polyepoxide. The present invention will be illustrated, simply by means of examples, as follows:
1. Examples 1 to 3
The following polyester compositions were prepared, using phosphono-succinic acid and various polyhydric alcohols: Example 1: neopentyl glycol (NPG) Example 2: 1,4-dimethylol-cyclohexane (CHDM) Example 3: ethylene glycol (EG)
1. 1 Procedure
Equivalent amounts of phosphonic acid and of each of the aforementioned diols were charged to a round-bottomed balloon, allowing its reaction at approximately 160 ° C for several hours while the acid number was monitored, until a very viscous liquid was produced.
1. 2 RESULTS
The apparent molecular weights, measured by gel permeation chromatography, are shown in the Table (below). These values are approximate, since the polymers are very polar. One should expect the actual molecular weight to be higher.
EXAMPLE Diol M (a)
1 NPG 9.638 2 CHDM 1.162 3 EG 19.004
(a) average molecular weight
2. Examples 4 and 5
Polyesters terminated in phosphono-succinic acid were prepared as follows: 2.1 Poly (oxinatedopentyl) succinate - Finished in phosphono-succinic acid.
2. 1.1 Procedure.
Neopentyl glycol (81.777 g, 0.786 mol) and succinic anhydride (77,000 g, 0.769 mol) were charged in a 250 ml resin vessel, equipped with a mechanical stirrer, a temperature probe, nitrogen inlet and a distillation apparatus. The mixture was stirred and heated to 160 ° C by means of a heating jacket. Once the mixture had melted, nitrogen was bubbled through it. The mixture was heated from 160 ° C to 190 ° C for 40 hours. A sample of the resulting intermediate product was taken after this time elapsed. The temperature was then lowered to 100 ° C and phosphono-succinic acid (3.078 g, 0.016 mol) was added. The mixture was heated at 160 ° C for 5.5 hours before allowing it to cool to room temperature. The product was crystallized from ethyl acetate to give a fine white powder.
2. 1.2 Results Gel permeation chromatography of the intermediate product indicated that the molecular weight of the product was approximately 20,000 gmol ~.
2. 2 Polyoxineopentyl phthalate) - Finished in phosphono-succinic acid. A procedure similar to that described in 2.1.1 was employed, replacing the succinic anhydride with phthalic anhydride. A solid polymer with emulsifying properties was produced.
Claims (17)
1. - A polymer composition comprising: (a) a phosphono-substituted carboxylic acid or an ester of said acid; and (b) a poly- or polyfunctional mono- or polyfunctional entity with (a).
2. A composition according to claim 1, wherein (a) is a tosyl-substituted aliphatic or aromatic dicarboxylic acid or an ester of said acid.
3. A composition according to claim 2, wherein (a) is phosphono succinic acid or an ether thereof.
4. A composition according to claim 2 or 3, wherein (a) is the dimethyl ester of phosphono-succinic acid.
5. A composition according to any of the preceding claims, wherein (b) is a polyhydric alcohol.
6. A composition according to claim 5, wherein (b) is an aliphatic or cycloaliphatic dihydpco alcohol.
7. A composition according to claim 5 or 6, wherein (b) is ethylene glycol, propylene glycol, neopentyl glycol or 1,4-d? Methanol-cyclohexane.
8. A composition according to claim 5, wherein (b) is a tphydric alcohol.
9. A composition according to claim 5 or 8, wherein (b) is glycerol.
10. A composition according to claim 1, wherein (b) is aliphatic, aromatic, mononuclear or polynuclear aromatic polycarboxylic acid or an ester or anhydride of said acid.
11. A composition according to claim 10, wherein (b) is succinic acid.
12. A composition according to claim 10, wherein (b) is terephthalic acid or phthalic anhydride.
13. A composition according to claim 10, wherein (b) is naphthalic acid or naphthalic anhydride.
14. A composition according to any of claims 1 to 4, wherein (b) is an aliphatic or aromatic polyamine.
15. A composition according to claim 14, wherein (b) is ethylenediamine.
16. A composition according to any of claims 1 to 4, wherein (b) is an aliphatic or aromatic polyisocyanate or polyepoxide.
17. A polymer composition, substantially as described hereinabove with reference to the examples.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9610070.6 | 1996-05-14 | ||
| GB9610070A GB2313126A (en) | 1996-05-14 | 1996-05-14 | Polymer compositions containing phosphorus |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| MX9703608A MX9703608A (en) | 1998-06-30 |
| MXPA97003608A true MXPA97003608A (en) | 1998-10-30 |
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