TW200808886A - Derivatives of pyrimidines as flame retardants - Google Patents

Info

Publication number

TW200808886A

TW200808886A TW096115294A TW96115294A TW200808886A TW 200808886 A TW200808886 A TW 200808886A TW 096115294 A TW096115294 A TW 096115294A TW 96115294 A TW96115294 A TW 96115294A TW 200808886 A TW200808886 A TW 200808886A

Authority

TW

Taiwan

Prior art keywords

group

aryl

alkyl

substituted

compound

Prior art date

2006-05-02

Links

• Espacenet
• Global Dossier
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• 239000003063 flame retardant Substances 0.000 title claims abstract description 73
• 150000003230 pyrimidines Chemical class 0.000 title description 2
• 239000000203 mixture Substances 0.000 claims abstract description 57
• RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 claims abstract description 53
• 229920000620 organic polymer Polymers 0.000 claims abstract description 39
• 238000000034 method Methods 0.000 claims abstract description 25
• 230000000979 retarding effect Effects 0.000 claims abstract description 8
• -1 Aralkylene Chemical group 0.000 claims description 175
• 125000003118 aryl group Chemical group 0.000 claims description 82
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 60
• 150000001875 compounds Chemical class 0.000 claims description 57
• 125000000217 alkyl group Chemical group 0.000 claims description 56
• 125000003342 alkenyl group Chemical group 0.000 claims description 36
• 229920000642 polymer Polymers 0.000 claims description 36
• 229920000768 polyamine Polymers 0.000 claims description 31
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 28
• 239000002253 acid Substances 0.000 claims description 24
• 125000004104 aryloxy group Chemical group 0.000 claims description 23
• 150000003839 salts Chemical class 0.000 claims description 23
• 125000003545 alkoxy group Chemical group 0.000 claims description 18
• 125000000304 alkynyl group Chemical group 0.000 claims description 17
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 17
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 17
• 229920000877 Melamine resin Polymers 0.000 claims description 16
• 150000001412 amines Chemical class 0.000 claims description 16
• JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 claims description 16
• 239000000654 additive Substances 0.000 claims description 15
• 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 14
• 125000002947 alkylene group Chemical group 0.000 claims description 13
• 239000003054 catalyst Substances 0.000 claims description 12
• 239000003795 chemical substances by application Substances 0.000 claims description 12
• 239000000052 vinegar Substances 0.000 claims description 12
• 235000021419 vinegar Nutrition 0.000 claims description 12
• 229910052736 halogen Inorganic materials 0.000 claims description 11
• 150000002367 halogens Chemical class 0.000 claims description 11
• 239000003381 stabilizer Substances 0.000 claims description 11
• 229920000728 polyester Polymers 0.000 claims description 10
• XQRLCLUYWUNEEH-UHFFFAOYSA-N diphosphonic acid Chemical compound OP(=O)OP(O)=O XQRLCLUYWUNEEH-UHFFFAOYSA-N 0.000 claims description 9
• 239000000945 filler Substances 0.000 claims description 9
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
• 230000000996 additive effect Effects 0.000 claims description 8
• MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 8
• ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 claims description 8
• 239000012744 reinforcing agent Substances 0.000 claims description 8
• KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 7
• 229910019142 PO4 Inorganic materials 0.000 claims description 7
• 125000005015 aryl alkynyl group Chemical group 0.000 claims description 7
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 7
• 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 7
• 239000010452 phosphate Substances 0.000 claims description 7
• LNDZXOWGUAIUBG-UHFFFAOYSA-N 6-aminouracil Chemical compound NC1=CC(=O)NC(=O)N1 LNDZXOWGUAIUBG-UHFFFAOYSA-N 0.000 claims description 6
• OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 6
• 125000003302 alkenyloxy group Chemical group 0.000 claims description 6
• 229910052698 phosphorus Inorganic materials 0.000 claims description 6
• 239000011574 phosphorus Substances 0.000 claims description 6
• 239000004417 polycarbonate Substances 0.000 claims description 6
• 238000006116 polymerization reaction Methods 0.000 claims description 6
• 150000003254 radicals Chemical class 0.000 claims description 6
• 229910052707 ruthenium Inorganic materials 0.000 claims description 6
• 239000002216 antistatic agent Substances 0.000 claims description 5
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
• 239000003995 emulsifying agent Substances 0.000 claims description 5
• 229910052739 hydrogen Inorganic materials 0.000 claims description 5
• 150000002576 ketones Chemical class 0.000 claims description 5
• 239000000314 lubricant Substances 0.000 claims description 5
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
• 230000003287 optical effect Effects 0.000 claims description 5
• 239000000049 pigment Substances 0.000 claims description 5
• 239000004014 plasticizer Substances 0.000 claims description 5
• 239000006254 rheological additive Substances 0.000 claims description 5
• KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 5
• BISHACNKZIBDFM-UHFFFAOYSA-N 5-amino-1h-pyrimidine-2,4-dione Chemical compound NC1=CNC(=O)NC1=O BISHACNKZIBDFM-UHFFFAOYSA-N 0.000 claims description 4
• 239000006096 absorbing agent Substances 0.000 claims description 4
• 150000001336 alkenes Chemical class 0.000 claims description 4
• 125000005133 alkynyloxy group Chemical group 0.000 claims description 4
• 239000013078 crystal Substances 0.000 claims description 4
• 125000004122 cyclic group Chemical group 0.000 claims description 4
• NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 4
• 239000004615 ingredient Substances 0.000 claims description 4
• 239000012796 inorganic flame retardant Substances 0.000 claims description 4
• 239000006078 metal deactivator Substances 0.000 claims description 4
• 238000002156 mixing Methods 0.000 claims description 4
• 150000002894 organic compounds Chemical class 0.000 claims description 4
• XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical class OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 claims description 4
• 229920000515 polycarbonate Polymers 0.000 claims description 4
• 125000003107 substituted aryl group Chemical group 0.000 claims description 4
• 230000002195 synergetic effect Effects 0.000 claims description 4
• 239000004952 Polyamide Substances 0.000 claims description 3
• KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 3
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 3
• 150000001408 amides Chemical class 0.000 claims description 3
• RHDGNLCLDBVESU-UHFFFAOYSA-N but-3-en-4-olide Chemical compound O=C1CC=CO1 RHDGNLCLDBVESU-UHFFFAOYSA-N 0.000 claims description 3
• 239000004088 foaming agent Substances 0.000 claims description 3
• 229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
• 239000004611 light stabiliser Substances 0.000 claims description 3
• 239000011707 mineral Substances 0.000 claims description 3
• SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical compound ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 claims description 3
• 229920002647 polyamide Polymers 0.000 claims description 3
• 239000002689 soil Substances 0.000 claims description 3
• 239000000126 substance Substances 0.000 claims description 3
• 229910052717 sulfur Inorganic materials 0.000 claims description 3
• 150000003573 thiols Chemical class 0.000 claims description 3
• 239000004604 Blowing Agent Substances 0.000 claims description 2
• AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 2
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 2
• BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims description 2
• 150000001335 aliphatic alkanes Chemical class 0.000 claims description 2
• 239000003963 antioxidant agent Substances 0.000 claims description 2
• 125000004429 atom Chemical group 0.000 claims description 2
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
• 229910052797 bismuth Inorganic materials 0.000 claims description 2
• JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims description 2
• 239000004202 carbamide Substances 0.000 claims description 2
• 230000006378 damage Effects 0.000 claims description 2
• 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
• 239000003112 inhibitor Substances 0.000 claims description 2
• 239000007800 oxidant agent Substances 0.000 claims description 2
• 239000001384 succinic acid Substances 0.000 claims description 2
• 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 2
• 125000000081 (C5-C8) cycloalkenyl group Chemical group 0.000 claims 2
• 150000001450 anions Chemical class 0.000 claims 2
• 125000005018 aryl alkenyl group Chemical group 0.000 claims 2
• 125000005418 aryl aryl group Chemical group 0.000 claims 2
• OTAFHZMPRISVEM-UHFFFAOYSA-N chromone Chemical compound C1=CC=C2C(=O)C=COC2=C1 OTAFHZMPRISVEM-UHFFFAOYSA-N 0.000 claims 2
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 2
• 229910052703 rhodium Inorganic materials 0.000 claims 2
• DJHGAFSJWGLOIV-UHFFFAOYSA-K Arsenate3- Chemical compound [O-][As]([O-])([O-])=O DJHGAFSJWGLOIV-UHFFFAOYSA-K 0.000 claims 1
• 241000206761 Bacillariophyta Species 0.000 claims 1
• 229940122361 Bisphosphonate Drugs 0.000 claims 1
• 101100294106 Caenorhabditis elegans nhr-3 gene Proteins 0.000 claims 1
• 229910052787 antimony Inorganic materials 0.000 claims 1
• WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims 1
• 229940000489 arsenate Drugs 0.000 claims 1
• 150000001622 bismuth compounds Chemical class 0.000 claims 1
• 150000004663 bisphosphonates Chemical class 0.000 claims 1
• 239000004067 bulking agent Substances 0.000 claims 1
• 239000000470 constituent Substances 0.000 claims 1
• 125000003493 decenyl group Chemical group [H]C([*])=C([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
• 125000006612 decyloxy group Chemical group 0.000 claims 1
• IIRVGTWONXBBAW-UHFFFAOYSA-M disodium;dioxido(oxo)phosphanium Chemical compound [Na+].[Na+].[O-][P+]([O-])=O IIRVGTWONXBBAW-UHFFFAOYSA-M 0.000 claims 1
• 229920001038 ethylene copolymer Polymers 0.000 claims 1
• 125000002541 furyl group Chemical group 0.000 claims 1
• 229910052760 oxygen Inorganic materials 0.000 claims 1
• 239000001301 oxygen Substances 0.000 claims 1
• 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims 1
• OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims 1
• 150000004032 porphyrins Chemical class 0.000 claims 1
• 150000007944 thiolates Chemical class 0.000 claims 1
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 abstract description 3
• PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical group C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 53
• 229920001577 copolymer Polymers 0.000 description 40
• VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 24
• 239000002585 base Substances 0.000 description 22
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 21
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
• 239000005977 Ethylene Substances 0.000 description 19
• 229910052757 nitrogen Inorganic materials 0.000 description 18
• 150000002148 esters Chemical class 0.000 description 17
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 16
• MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 15
• NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 15
• ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 13
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
• 239000000178 monomer Substances 0.000 description 12
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• 239000007983 Tris buffer Substances 0.000 description 11
• 229910052751 metal Inorganic materials 0.000 description 11
• 239000002184 metal Substances 0.000 description 11
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
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• 238000012360 testing method Methods 0.000 description 9
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• QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 8
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• 229940099514 low-density polyethylene Drugs 0.000 description 8
• 229920002857 polybutadiene Polymers 0.000 description 8
• KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 7
• 150000007513 acids Chemical class 0.000 description 7
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• FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 6
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• 239000007859 condensation product Substances 0.000 description 6
• 150000001993 dienes Chemical class 0.000 description 6
• 229920001903 high density polyethylene Polymers 0.000 description 6
• GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 6
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• 239000000463 material Substances 0.000 description 5
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• 229920006324 polyoxymethylene Polymers 0.000 description 5
• 239000000047 product Substances 0.000 description 5
• GXURZKWLMYOCDX-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol;dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O.OCC(CO)(CO)CO GXURZKWLMYOCDX-UHFFFAOYSA-N 0.000 description 4
• GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical compound CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 4
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• UZQJQLCWGVJXEE-UHFFFAOYSA-N 5-chlorobenzotriazole Chemical compound [CH]1C(Cl)=CC=C2N=NN=C21 UZQJQLCWGVJXEE-UHFFFAOYSA-N 0.000 description 4
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• 229910052794 bromium Inorganic materials 0.000 description 4
• 238000004132 cross linking Methods 0.000 description 4
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
• 150000002009 diols Chemical class 0.000 description 4
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• NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 4
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• 229920000098 polyolefin Polymers 0.000 description 4
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• 238000003672 processing method Methods 0.000 description 4
• YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 4
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• 229920001897 terpolymer Polymers 0.000 description 4
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
• 239000004416 thermosoftening plastic Substances 0.000 description 4
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• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
• 239000011701 zinc Substances 0.000 description 4
• JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 3
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