DE2338506A1

DE2338506A1 - Feuerhemmende mittel und verfahren zu ihrer herstellung

Feuerhemmende mittel und verfahren zu ihrer herstellung

Info

Publication number: DE2338506A1
Authority: DE; Germany
Prior art keywords: radicals; group; compound according; oxygen; hydrogen
Prior art date: 1972-07-31
Legal status : Pending

Application number

DE19732338506

Other languages

German (de)

English (en)

Inventor

Albert Wayne Morgan

Ignatius Schumacher

Current Assignee

Monsanto Co

Original Assignee

Monsanto Co

Priority date

1972-07-31

Filing date

1973-07-30

Publication date

1974-02-21

1973-07-30 Application filed by Monsanto Co filed Critical Monsanto Co

1974-02-21 Publication of DE2338506A1 publication Critical patent/DE2338506A1/de

Status Pending legal-status Critical Current

Links

239000003063 flame retardant Substances 0.000 title claims description 45
238000000034 method Methods 0.000 title claims description 18
238000004519 manufacturing process Methods 0.000 title description 11
150000001875 compounds Chemical class 0.000 claims description 132
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 40
229910052760 oxygen Inorganic materials 0.000 claims description 39
239000001301 oxygen Substances 0.000 claims description 39
238000002360 preparation method Methods 0.000 claims description 27
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 26
239000001257 hydrogen Substances 0.000 claims description 24
229910052739 hydrogen Inorganic materials 0.000 claims description 24
239000000463 material Substances 0.000 claims description 24
125000000217 alkyl group Chemical group 0.000 claims description 21
125000003118 aryl group Chemical group 0.000 claims description 19
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 17
229910052717 sulfur Inorganic materials 0.000 claims description 17
239000011593 sulfur Substances 0.000 claims description 17
239000002253 acid Substances 0.000 claims description 16
125000004432 carbon atom Chemical group C* 0.000 claims description 16
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
150000008298 phosphoramidates Chemical class 0.000 claims description 13
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 11
239000005977 Ethylene Substances 0.000 claims description 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
125000002877 alkyl aryl group Chemical group 0.000 claims description 10
125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 9
239000003085 diluting agent Substances 0.000 claims description 9
150000002431 hydrogen Chemical group 0.000 claims description 8
239000003513 alkali Substances 0.000 claims description 7
229910052757 nitrogen Inorganic materials 0.000 claims description 7
125000002947 alkylene group Chemical group 0.000 claims description 6
150000003863 ammonium salts Chemical class 0.000 claims description 6
125000000753 cycloalkyl group Chemical group 0.000 claims description 6
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125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 5
125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 5
150000001447 alkali salts Chemical class 0.000 claims description 5
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125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 4
239000000908 ammonium hydroxide Substances 0.000 claims description 4
239000007864 aqueous solution Substances 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 4
150000002367 halogens Chemical class 0.000 claims description 4
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239000001856 Ethyl cellulose Substances 0.000 claims description 3
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 3
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150000001340 alkali metals Chemical class 0.000 claims description 3
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125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 3
229920001059 synthetic polymer Polymers 0.000 claims description 3
239000002023 wood Substances 0.000 claims description 3
244000043261 Hevea brasiliensis Species 0.000 claims description 2
125000000732 arylene group Chemical group 0.000 claims description 2
239000007799 cork Substances 0.000 claims description 2
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125000002757 morpholinyl group Chemical group 0.000 claims 6
229920002994 synthetic fiber Polymers 0.000 claims 4
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical group [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 3
125000004185 ester group Chemical group 0.000 claims 2
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims 2
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 2
125000000542 sulfonic acid group Chemical group 0.000 claims 2
125000005586 carbonic acid group Chemical group 0.000 claims 1
125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 1
-1 aromatic alcohols Chemical class 0.000 description 62
229910052698 phosphorus Inorganic materials 0.000 description 36
239000011574 phosphorus Substances 0.000 description 36
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239000000203 mixture Substances 0.000 description 21
150000001412 amines Chemical class 0.000 description 18
229920005989 resin Polymers 0.000 description 18
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XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 17
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MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 15
150000003254 radicals Chemical class 0.000 description 15
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229920001577 copolymer Polymers 0.000 description 13
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238000006243 chemical reaction Methods 0.000 description 12
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239000000047 product Substances 0.000 description 11
239000000243 solution Substances 0.000 description 11
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 10
239000004814 polyurethane Substances 0.000 description 10
229920002635 polyurethane Polymers 0.000 description 10
229920001897 terpolymer Polymers 0.000 description 10
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 9
229920000728 polyester Polymers 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 8
150000002148 esters Chemical class 0.000 description 8
229920002554 vinyl polymer Polymers 0.000 description 8
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 7
229910000041 hydrogen chloride Inorganic materials 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 6
IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 6
239000003795 chemical substances by application Substances 0.000 description 6
239000006260 foam Substances 0.000 description 6
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 6
150000003335 secondary amines Chemical class 0.000 description 6
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125000001931 aliphatic group Chemical group 0.000 description 5
150000008044 alkali metal hydroxides Chemical class 0.000 description 5
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238000009472 formulation Methods 0.000 description 5
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125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
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DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 4
ORLQHILJRHBSAY-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1(CO)CCCCC1 ORLQHILJRHBSAY-UHFFFAOYSA-N 0.000 description 4
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150000001408 amides Chemical class 0.000 description 4
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229920003229 poly(methyl methacrylate) Polymers 0.000 description 4
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238000010992 reflux Methods 0.000 description 4
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125000004122 cyclic group Chemical group 0.000 description 3
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125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
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