Organic phosphorus-based compound, and flame retardant and flame-retardant product comprising the same

Patent metadata

Field	Value
Publication number	US-10919923-B2
Application number	US-201716328891-A
Country	US
Kind code	B2
Filing date	Mar 10, 2017
Priority date	Sep 16, 2016
Publication date	Feb 16, 2021
Grant date	Feb 16, 2021

Abstract

An organic phosphorus-based compound which satisfies the following requirements (i) to (viii) and is represented by the following formula (1): (i) the organic purity should be not lower than 98%; (ii) the solubility in 20° C. water should be not higher than 0.1 g/100 g of water; (iii) the total halogen component content should be not higher than 1,000 ppm; (iv) the total volatile organic matter content should be not higher than 800 ppm; (v) the Δ pH value should be not larger than 1.0; (vi) the volume standard median diameter should be not larger than 30 μm; (vii) the maximum particle diameter should be not larger than 200 μm; and (viii) the standard deviation represented by the following formula should be not larger than 20 μm. Standard deviation=(d84%+d16%)/2; wherein d84%: particle diameter at a point where the cumulative curve becomes 84% (μm), and d16%: particle diameter at a point where the cumulative curve becomes 16% (μm).

In the above formula, R 2 and R 5 may be the same or different and are each a phenyl group which may have a substituent, naphthyl group which may have a substituent, anthryl group which may have a substituent, or branched or linear alkyl group having 1 to 4 carbon atoms which may have an aromatic substituent. R 1 , R 3 , R 4 and R 6 may be the same or different and are each a hydrogen atom, branched or linear alkyl group having 1 to 4 carbon atoms, phenyl group which may have a substituent, naphthyl group which may have a substituent, or anthryl group which may have a substituent.

First claim

The invention claimed is:

1. An organic phosphorus-based compound which satisfies the following requirements (i) to (viii) and is represented by the following formula (1):
(i) the organic purity is not lower than 98%;
(ii) the solubility in 20° C. water is not higher than 0.1 g/100 g of water;
(iii) the total halogen component content is not higher than 1,000 ppm;
(iv) the total volatile organic matter content is not higher than 800 ppm;
(v) the Δ pH value is not larger than 1.0;
(vi) the volume standard median diameter is not larger than 30 μm;
(vii) the maximum particle diameter is not larger than 200 μm; and
(viii) the standard deviation represented by the following formula (6) is not larger than 15 μm;
Standard deviation=( d 84%+ d 16%)/2  (6)

 d84%: particle diameter at a point where the cumulative curve becomes 84% (μm)
 d16%: particle diameter at a point where the cumulative curve becomes 16% (μm)

wherein, in formula (1),
R 2 and R 5 may be the same or different and are each a phenyl group which may have a substituent, naphthyl group which may have a substituent, anthryl group which may have a substituent, or branched or linear alkyl group having 1 to 4 carbon atoms which may have an aromatic substituent, and
R 1 , R 3 , R 4 and R 6 may be the same or different and are each a hydrogen atom, branched or linear alkyl group having 1 to 4 carbon atoms, phenyl group which may have a substituent, naphthyl group which may have a substituent, or anthryl group which may have a substituent.

2. The organic phosphorus-based compound according to claim 1 , wherein the organic phosphorus-based compound represented by the formula (1) is at least one compound selected from the group consisting of:

3. The organic phosphorus-based compound according to claim 1 , which has (iii) a total halogen component content of not higher than 500 ppm, (iv) a total volatile organic matter content of not higher than 500 ppm, (v) a Δ pH value of not larger than 0.5, (vi) a volume-standard median diameter of not larger than 20 μm and (vii) a maximum particle diameter of not larger than 150 μm.

4. A flame retardant comprising at least 50 wt % of the organic phosphorus-based compound of claim 1 .

5. A flame-retardant product comprising the flame retardant of claim 4 .

6. A process for producing the organic phosphorus-based compound of claim 1 , comprising the steps of:
cleaning a synthesized organic phosphorus-based compound represented by the formula (1) with an aromatic organic solvent to obtain a roughly purified product (cleaning step 1);
reflux cleaning the roughly purified product with a compound represented by the following formula (7) or (8) at a cleaning temperature of 35 to 120° C. to obtain a purified product (cleaning step 2);
R 9 —OH  (7)

R 10 —C(O)—R 11   (8)

wherein R 9 is a hydrogen atom, or linear or branched alkyl group having 1 to 6 carbon atoms, and R 10 and R 11 may be the same or different and are each a linear or branched alkyl group having 1 to 6 carbon atoms; and
pulverizing the purified product to obtain the organic phosphorus-based compound (pulverizing step).

Assignees

• Teijin Ltd

Inventors

• Yamanaka Katsuhiro
• IMAZATO Kenta
• Takahashi Naoshi

Classifications

• C08J2363/04

  Epoxynovolacs · CPC title

• C07F9/657181 Primary

  the ring phosphorus atom and, at least, one ring oxygen atom being part of a (thio)phosphonic acid derivative · CPC title

• C08K5/5357

  cyclic · CPC title

• C08J5/244 Primary

  using glass fibres · CPC title

• C07F9/6574

  Esters of oxyacids of phosphorus {(C07F9/657163 takes precedence)} · CPC title