CN1219845C - 包含c.i.活性紫5染料的防冻浓缩物 - Google Patents
包含c.i.活性紫5染料的防冻浓缩物 Download PDFInfo
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- CN1219845C CN1219845C CNB028095197A CN02809519A CN1219845C CN 1219845 C CN1219845 C CN 1219845C CN B028095197 A CNB028095197 A CN B028095197A CN 02809519 A CN02809519 A CN 02809519A CN 1219845 C CN1219845 C CN 1219845C
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- antifreeze concentrates
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- 230000002528 anti-freeze Effects 0.000 title claims abstract description 34
- 239000012141 concentrate Substances 0.000 title claims abstract description 34
- DLPITEUCXDBWSF-UHFFFAOYSA-K trisodium N-[8-oxido-7-[[2-oxido-4-(2-sulfooxyethylsulfonyl)phenyl]diazenyl]-3,6-disulfonaphthalen-1-yl]ethanimidate Chemical compound CC(=NC1=C2C(=CC(=C1)S(=O)(=O)O)C=C(C(=C2[O-])N=NC3=C(C=C(C=C3)S(=O)(=O)CCOS(=O)(=O)O)[O-])S(=O)(=O)O)[O-].[Na+].[Na+].[Na+] DLPITEUCXDBWSF-UHFFFAOYSA-K 0.000 title claims abstract description 16
- -1 alkylene glycols Chemical class 0.000 claims abstract description 26
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims abstract description 24
- 235000011187 glycerol Nutrition 0.000 claims abstract description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 58
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 30
- 239000000203 mixture Substances 0.000 claims description 28
- 239000000975 dye Substances 0.000 claims description 25
- 239000000463 material Substances 0.000 claims description 25
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 14
- 229910052783 alkali metal Inorganic materials 0.000 claims description 12
- 125000001931 aliphatic group Chemical group 0.000 claims description 11
- 150000003863 ammonium salts Chemical class 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 10
- 239000002826 coolant Substances 0.000 claims description 10
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000002723 alicyclic group Chemical group 0.000 claims description 5
- 150000001735 carboxylic acids Chemical class 0.000 claims description 5
- 125000000524 functional group Chemical group 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000004135 Bone phosphate Substances 0.000 claims description 3
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 3
- 229910052910 alkali metal silicate Inorganic materials 0.000 claims description 3
- 150000004982 aromatic amines Chemical class 0.000 claims description 3
- 238000007710 freezing Methods 0.000 claims description 3
- 230000008014 freezing Effects 0.000 claims description 3
- 229910000077 silane Inorganic materials 0.000 claims description 3
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 claims description 3
- 229940124530 sulfonamide Drugs 0.000 claims description 3
- JSYPRLVDJYQMAI-ODZAUARKSA-N (z)-but-2-enedioic acid;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)\C=C/C(O)=O JSYPRLVDJYQMAI-ODZAUARKSA-N 0.000 claims description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 2
- DBBAUITUQRZERI-UHFFFAOYSA-N 2-ethenyl-1h-imidazole;1-ethenylpyrrolidin-2-one Chemical compound C=CC1=NC=CN1.C=CN1CCCC1=O DBBAUITUQRZERI-UHFFFAOYSA-N 0.000 claims description 2
- 229920002125 Sokalan® Polymers 0.000 claims description 2
- 229910001963 alkali metal nitrate Inorganic materials 0.000 claims description 2
- 229910000318 alkali metal phosphate Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 229910001618 alkaline earth metal fluoride Inorganic materials 0.000 claims description 2
- 229910001964 alkaline earth metal nitrate Inorganic materials 0.000 claims description 2
- 150000001336 alkenes Chemical class 0.000 claims description 2
- 229910052728 basic metal Inorganic materials 0.000 claims description 2
- 150000003818 basic metals Chemical class 0.000 claims description 2
- 239000008233 hard water Substances 0.000 claims description 2
- 150000002391 heterocyclic compounds Chemical class 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 239000004584 polyacrylic acid Substances 0.000 claims description 2
- 229920001444 polymaleic acid Polymers 0.000 claims description 2
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- 239000003086 colorant Substances 0.000 abstract 1
- 238000012360 testing method Methods 0.000 description 12
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 10
- 238000001816 cooling Methods 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000005260 corrosion Methods 0.000 description 6
- 230000007797 corrosion Effects 0.000 description 6
- ZIUSSTSXXLLKKK-KOBPDPAPSA-N (1e,4z,6e)-5-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,4,6-trien-3-one Chemical compound C1=C(O)C(OC)=CC(\C=C\C(\O)=C\C(=O)\C=C\C=2C=C(OC)C(O)=CC=2)=C1 ZIUSSTSXXLLKKK-KOBPDPAPSA-N 0.000 description 5
- VFLDPWHFBUODDF-FCXRPNKRSA-N Curcumin Natural products C1=C(O)C(OC)=CC(\C=C\C(=O)CC(=O)\C=C\C=2C=C(OC)C(O)=CC=2)=C1 VFLDPWHFBUODDF-FCXRPNKRSA-N 0.000 description 5
- 239000004411 aluminium Substances 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- VFLDPWHFBUODDF-UHFFFAOYSA-N diferuloylmethane Natural products C1=C(O)C(OC)=CC(C=CC(=O)CC(=O)C=CC=2C=C(OC)C(O)=CC=2)=C1 VFLDPWHFBUODDF-UHFFFAOYSA-N 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- FPAYXBWMYIMERV-UHFFFAOYSA-L disodium;5-methyl-2-[[4-(4-methyl-2-sulfonatoanilino)-9,10-dioxoanthracen-1-yl]amino]benzenesulfonate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)C1=CC(C)=CC=C1NC(C=1C(=O)C2=CC=CC=C2C(=O)C=11)=CC=C1NC1=CC=C(C)C=C1S([O-])(=O)=O FPAYXBWMYIMERV-UHFFFAOYSA-L 0.000 description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 239000003507 refrigerant Substances 0.000 description 3
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 229910001369 Brass Inorganic materials 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 125000003368 amide group Chemical class 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 239000012964 benzotriazole Substances 0.000 description 2
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 229910021538 borax Inorganic materials 0.000 description 2
- 239000010951 brass Substances 0.000 description 2
- LJOODBDWMQKMFB-UHFFFAOYSA-N cyclohexylacetic acid Chemical compound OC(=O)CC1CCCCC1 LJOODBDWMQKMFB-UHFFFAOYSA-N 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 2
- 230000003628 erosive effect Effects 0.000 description 2
- GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 description 2
- JFCQEDHGNNZCLN-UHFFFAOYSA-N glutaric acid Chemical compound OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 2
- 125000001072 heteroaryl group Chemical group 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- YIXJRHPUWRPCBB-UHFFFAOYSA-N magnesium nitrate Chemical compound [Mg+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O YIXJRHPUWRPCBB-UHFFFAOYSA-N 0.000 description 2
- 239000002075 main ingredient Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910001092 metal group alloy Inorganic materials 0.000 description 2
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
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- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 2
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- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000004328 sodium tetraborate Substances 0.000 description 2
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- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
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- 238000012546 transfer Methods 0.000 description 2
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 2
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- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- XRIGHGYEGNDPEU-UHFFFAOYSA-N 1-anilinoanthracene-9,10-dione Chemical group C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1NC1=CC=CC=C1 XRIGHGYEGNDPEU-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- QFGCFKJIPBRJGM-UHFFFAOYSA-N 12-[(2-methylpropan-2-yl)oxy]-12-oxododecanoic acid Chemical compound CC(C)(C)OC(=O)CCCCCCCCCCC(O)=O QFGCFKJIPBRJGM-UHFFFAOYSA-N 0.000 description 1
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
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- KDVYCTOWXSLNNI-UHFFFAOYSA-N 4-t-Butylbenzoic acid Chemical compound CC(C)(C)C1=CC=C(C(O)=O)C=C1 KDVYCTOWXSLNNI-UHFFFAOYSA-N 0.000 description 1
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 1
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 1
- 229910001018 Cast iron Inorganic materials 0.000 description 1
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- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
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- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
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- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
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- 150000007513 acids Chemical class 0.000 description 1
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- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- OYTKINVCDFNREN-UHFFFAOYSA-N amifampridine Chemical compound NC1=CC=NC=C1N OYTKINVCDFNREN-UHFFFAOYSA-N 0.000 description 1
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- 239000007864 aqueous solution Substances 0.000 description 1
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- 239000012752 auxiliary agent Substances 0.000 description 1
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- FSTZWKIICVTWLA-UHFFFAOYSA-N benzenesulfonic acid;magnesium Chemical compound [Mg].OS(=O)(=O)C1=CC=CC=C1 FSTZWKIICVTWLA-UHFFFAOYSA-N 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
- 239000001045 blue dye Substances 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- ZZHNUBIHHLQNHX-UHFFFAOYSA-N butoxysilane Chemical compound CCCCO[SiH3] ZZHNUBIHHLQNHX-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
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- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 229910000397 disodium phosphate Inorganic materials 0.000 description 1
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- 238000003786 synthesis reaction Methods 0.000 description 1
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- C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
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Abstract
本发明涉及基于亚烷基二醇或其衍生物或基于甘油的防冻浓缩物,包含基于该浓缩物的总量为0.0005-0.1重量%的C.I.活性紫5(染料索引号18097)染料。
Description
本发明涉及基于亚烷基二醇或其衍生物或基于甘油的新型防冻浓缩物,包含作为染料的染料索引(“C.I.”)活性紫5(染料索引号18097)。本发明还涉及包含所述防冻浓缩物的即可使用的含水冷却剂组合物。本发明还涉及这些防冻浓缩物在制备内燃机用含水冷却剂组合物中的用途。
用于例如汽车中内燃机的冷却系统的防冻浓缩物通常包含亚烷基二醇,尤其是乙二醇或丙二醇作为主要组分。为了用于冷却系统中,将它们用水稀释,用以确保良好的散热以及提供防冻保护。
亚烷基二醇/水混合物在内燃机的操作温度下极具腐蚀性。为此,必须通过使用缓蚀剂充分保护用于冷却系统中的各种金属如钢、铸铁、铜、黄铜、铝、镁及其合金以及焊接金属如锡焊料以防各种类型的腐蚀,例如点腐蚀、裂隙腐蚀、侵蚀或气蚀。
防冻浓缩物和散热器保护组合物几乎总是通过加入染料而着色,以防止与汽车中的其它官能流体如筛网洗涤液或制动液混淆。着色也是用来在冷却系统中使用时或使用后可识别。
散热器保护组合物在实践中经历极限温度和强氧化条件。已经发现仅非常少量的染料在这类环境中保持稳定。工业上主要应用C.I.直接蓝199(C.I.74190)、C.I.直接蓝86(C.I.74180)、C.I.酸性绿25(C.I.61570)、C.I.酸性黄73(C.I.45350)和荧光素钠。C.I.酸性绿25通常与C.I.酸性黄73或荧光素钠结合,得到荧光绿色。C.I.酸性黄221通常也用作黄色染料,C.I.碱性紫10(C.I.45170)用作红色染料。
US-A 5,723,060(1)描述了具有1-氨基-4-苯胺基蒽醌结构的蓝色染料作为冷却剂组合物的着色剂。
US-A 5,725,794(2)推荐了包含聚氧化烯取代的活性染料的冷却剂组合物,据说该染料因聚合物取代基而具有改进的热稳定性;例如诸如C.I.碱性紫3或C.I.活性紫5的活性染料尤其与聚氧化烯胺类或与聚氧乙烯-二甲基硅氧烷共聚物进行化学反应。EP-B 864 616(3)同样教导了该类活性染料与聚氧乙烯-二甲基硅氧烷共聚物的反应及其在冷却剂组合物中的用途。与未取代的活性染料相比,(2)和(3)的教导所具有的缺点尤其在于额外的合成步骤以及这类染料缺少工业可得性。
从汽车工业角度来看,许多用于散热器保护组合物中的染料的缺点在于由于为了润滑水泵需要有意地轻微泄露,它们在水泵的金属外表面上形成逸出冷却剂的着色残余物,其发生可能产生生锈的印象或不正确地归因于有缺陷或受损的泵垫圈,导致消费者产生不公正的抱怨。
因此需要热稳定的染料,它们不会形成着色残余物,而是在该冷却系统的泄露点处的金属表面上干燥之后至多形成无色残余物。
令人惊奇的是,现已发现未取代的活性染料C.I.活性紫5(染料索引号18097)不仅在冷却剂中具有优异的热稳定性,而且与其它用于冷却剂中的染料形成相反的是,它不会在冷却系统的泄露处的金属表面上留下着色残余物。
本发明因此涉及一种基于亚烷基二醇或其衍生物或基于甘油的防冻浓缩物,基于该浓缩物的总量包含0.0005-0.1重量%,优选0.001-0.05重量%,尤其是0.002-0.02重量%的染料C.I.活性紫5(染料索引号18097)。
C.I.活性紫5(染料索引号18097)为5-(乙酰氨基)-4-羟基-3-[[2-羟基-4-1[2-(磺基氧基)乙基]磺酰基]苯基]偶氮]-2,7-萘二磺酸的铜络合物。其CAS登记号为12226-38-9。
C.I.活性紫5染料以未衍生形式,即以市售形式加入防冻浓缩物中。其加入方式应排除与防冻浓缩物的组分发生化学反应—至少在引入冷却系统中之前。
因此本发明还涉及一种制备防冻浓缩物的方法,其中将C.I.活性紫5(染料索引号18097)染料以基于防冻浓缩物总量为0.0005-0.1重量%,优选0.001-0.05重量%,尤其是0.002-0.02重量%的量加入基于亚烷基二醇或其衍生物或基于甘油的防冻浓缩物中。该加入通常在由该浓缩物制备即可使用的含水冷却剂组合物之前或在将即可使用的含水冷却剂组合物加入冷却系统中之前进行。
在优选的实施方案中,本发明防冻浓缩物除了染料外还包含下列化合物:
a)基于该浓缩物的总量为0.05-5重量%的一种或多种脂族、脂环族或芳族一元羧酸,其各自具有3-16个碳原子且呈其碱金属盐、铵盐或取代铵盐形式,和/或
b)基于该浓缩物的总量为0.05-5重量%的一种或多种脂族或芳族二-或三元羧酸,其各自具有3-21个碳原子且呈其碱金属盐、铵盐或取代铵盐形式,和/或
c)一种或多种碱金属硼酸盐、碱金属磷酸盐、碱金属硅酸盐、碱金属亚硝酸盐、碱金属或碱土金属硝酸盐、碱金属钼酸盐或碱金属或碱土金属氟化物,它们各自基于该浓缩物的总量为至多1重量%,和/或
d)基于该浓缩物的总量为0.05-5重量%的一种或多种具有2-15个碳原子且可以额外含有醚氧原子或羟基的脂族、脂环族或芳族胺,和/或
e)基于该浓缩物的总量为0.05-5重量%的一种或多种具有4-10个碳原子且可以苯并稠合和/或可以带有额外官能基团的单环或双环不饱和或部分不饱和杂环化合物,和/或
f)基于该浓缩物的总量为0.05-5重量%的一种或多种四(C1-C8-烷氧基)硅烷(原硅酸四-C1-C8-烷基酯),和/或
g)基于该浓缩物的总量为0.05-10重量%的一种或多种羧酰胺和/或磺酰胺,和/或
h)基于该浓缩物的总量至多为1重量%的一种或多种硬水稳定剂,该稳定剂基于聚丙烯酸、聚马来酸、丙烯酸-马来酸共聚物、聚乙烯基吡咯烷酮、聚乙烯基咪唑、乙烯基吡咯烷酮-乙烯基咪唑共聚物和/或不饱和羧酸和烯烃的共聚物。
来自a)-g)组的化合物通常为缓蚀剂。
合适的线性或支化脂族或脂环族一元羧酸a)例如为丙酸、戊酸、己酸、环己基乙酸、辛酸、2-乙基己酸、壬酸、异壬酸、癸酸、十一烷酸和十二烷酸。合适的芳族一元羧酸a)尤其为苯甲酸和例如C1-C8-烷基苯甲酸,例如邻-、间-和对-甲基苯甲酸以及对叔丁基苯甲酸,还有含羟基的芳族一元羧酸,例如邻-、间-和对-羟基苯甲酸,邻-、间-和对-(羟甲基)苯甲酸,以及卤代苯甲酸,例如邻-、间-和对-氟苯甲酸。
二-和三元羧酸b)的典型实例是丙二酸、琥珀酸、戊二酸、己二酸、庚二酸、辛二酸、壬二酸、癸二酸、十一烷二酸、十二烷二酸、二聚环戊二烯二甲酸、邻苯二甲酸、对苯二甲酸和三嗪三亚氨基羧酸如6,6’,6”-(1,3,5-三嗪-2,4,6-三基三亚氨基)三己酸。
所有所述a)和b)组的羧酸呈碱金属盐,尤其是钠盐或钾盐形式,或呈铵盐或取代铵盐(胺盐)形式,例如与氨、三烷基胺或三链烷醇胺的盐。
在c)下提到的缓蚀剂的典型实例为四硼酸钠(硼砂)、磷酸氢二钠、磷酸三钠、偏硅酸钠、亚硝酸钠、硝酸钠、硝酸镁、氟化钠、氟化钾、氟化镁和钼酸钠。
当同时使用碱金属硅酸盐时,它们有利地由常规有机硅膦酸盐或有机硅磺酸盐以常规量稳定。
具有2-15个碳原子、优选4-8个碳原子的且可以额外含有醚氧原子,尤其是1-3个醚氧原子,或羟基,尤其是1-3个羟基的合适脂族、脂环族或芳族胺d)例如为乙胺、丙胺、异丙胺、正丁胺、异丁胺、仲丁胺、叔丁胺、正戊胺、正己胺、正庚胺、正辛胺、异壬胺、二正丙胺、二异丙胺、二正丁胺、单乙醇胺、二乙醇胺、三乙醇胺、哌啶、吗啉、苯胺和苄胺。脂族和脂环族胺d)通常为饱和的。
杂环化合物e)例如为单环的5-或6元体系,其具有1、2或3个氮原子或一个氮原子和一个硫原子且可以为苯并稠合的。也可以使用包含5-和/或6-元亚环的双环体系,其典型的是具有2、3或4个氮原子。杂环化合物e)可以额外带有官能基团,优选C1-C4-烷氧基、氨基和/或巯基。杂环骨架当然也可以带有烷基,尤其是C1-C4-烷基。
杂环化合物e)的典型实例是苯并三唑、甲苯并三唑(甲苯基三唑)、氢化甲苯并三唑、1H-1,2,4-三唑、苯并咪唑、苯并噻唑、腺嘌呤、嘌呤、6-甲氧基嘌呤、吲哚、异吲哚、二氢异吲哚、吡啶、嘧啶、3,4-二氨基吡啶、2-氨基嘧啶和2-巯基嘧啶。
合适的四(C1-C8-烷氧基)硅烷f)例如为四甲氧基硅烷、四乙氧基硅烷、四正丙氧基硅烷和四正丁氧基硅烷。
酰胺g)需要的话可以在该酰胺基团的氮原子上被烷基,例如被C1-C4-烷基取代。该分子的芳族或杂芳族骨架当然也可携带这类烷基。该分子可以含有一个或多个,优选一个或两个酰胺基团。酰胺可以带有额外官能基团,优选C1-C4-烷氧基、氨基、氯、氟、羟基和/或乙酰基;尤其是这类官能基团作为所存在的芳族或杂芳族环上的取代基存在。
在g)组中的这类羧酰胺和磺酰胺的典型实例列于DE-A 1036 031中。除了来自a)-g)组的所述抑制剂组分外,还可以以常规量将有机酸的可溶性镁盐,例如苯磺酸镁、甲磺酸镁、乙酸镁或丙酸镁,氢化咔唑或季铵化咪唑用作其它抑制剂,如DE-A 196 05 509所述。
在本发明防冻浓缩物中的上述额外组分中,优选来自a)和/或b)组的羧酸和/或来自e)组的杂环化合物。在特别优选的实施方案中,本发明防冻浓缩物除了所述染料外还包含各自为0.05-5重量%,尤其是0.5-3重量%的两种互不相同的选自a)和/或b)组的羧酸以及0.05-5重量%,尤其是0.1-0.5重量%的一种或多种选自e)组的杂环化合物。
这些互不相同的羧酸可以例如为脂族一元羧酸与脂族二元羧酸的混合物、芳族一元羧酸与脂族二元羧酸的混合物、脂族一元羧酸与芳族一元羧酸的混合物、两种脂族一元羧酸的混合物或两种脂族二元羧酸的混合物。在这里待同时使用的合适杂环化合物尤其为苯并三唑和甲苯并三唑。
本发明防冻浓缩物的pH通常为4-11,优选4-10,尤其是4.5-8.5。需要的话,所需pH在这里也可通过向配制剂中加入碱金属氢氧化物、氨或胺来设定;固体氢氧化钠或氢氧化钾和氢氧化钠水溶液或氢氧化钾水溶液特别适于该目的。待同时使用的羧酸有利地以相应碱金属盐直接加入,以自动达到所需pH范围。然而,羧酸也可以以游离酸加入,然后使用碱金属氢氧化物、氨或胺中和,产生所需pH范围。
通常构成本发明防冻浓缩物的主要组分(通常为至少75重量%,尤其为至少85重量%)的合适液体醇类冰点降低剂是亚烷基二醇及其衍生物以及甘油,特别是丙二醇且尤其是乙二醇。然而,高级二醇和二醇醚也是合适的,例如二甘醇、二丙二醇和二醇的单醚,例如乙二醇、丙二醇、二甘醇和二丙二醇的甲醚、乙醚、丙醚和丁醚。还可以使用所述二醇和二醇醚的混合物以及这些二醇与甘油以及需要的话还有这些二醇醚的混合物。
在优选的实施方案中,本发明防冻浓缩物基于乙二醇或丙二醇或亚烷基二醇的混合物或甘油与乙二醇或丙二醇的混合物,它们各自包含至少95重量%的乙二醇和/或丙二醇和/或甘油。
作为其它常规助剂,本发明防冻浓缩物还可包含消泡剂(其量通常为0.003-0.008重量%),在摄食情况下出于卫生和安全原因,包含苦味物质(例如苯甲酸变性托宁(Denatoniumbenzoat)型苦味物质。
本发明还涉及冰点降低的即可使用的含水冷却剂组合物,其尤其在汽车领域中用于保护内燃机的散热器,该组合物包含水和10-90重量%,尤其是20-60重量%的本发明防冻浓缩物。
下列实施例用来说明本发明,而不限制本发明。
实施例
使用市售防冻浓缩物进行试验,该浓缩物基于乙二醇与作为抑制剂组分的己二酸、癸二酸和甲苯并三唑的混合物。
通过将50ppm相应染料加入该浓缩物中并彻底混合而制备着不同色的样品。
借助玻璃移液吸管将两滴未着色浓缩物、两滴含有染料C.I.活性紫5的本发明配制剂和两滴用其它染料制备的对比样品施加于铝板(合金GA(10mg,直径70mm,厚度6mm)上。将各铝板置于电热板(IKA-Combimag RCT,600W,购自Janke & Kunkel/Staufen)上并加热5分钟。然后分别肉眼评价蒸发的残余物。
热板试验结果示于表1中。它们显示在使用染料C.I.活性紫5的情况下和在未着色浓缩物情况下,出现白色残余物,而在使用其它染料的情况下,在金属表面上形成不希望的着色残余物。
表2和3显示含有50ppm C.I.活性紫5的本发明配制剂在根据ASTMD 1384-97的玻璃器皿腐蚀试验中和在根据ASTM D 4340的传热腐蚀试验中的良好结果。这些试验还表明该染料在配制剂中稳定,甚至在加热时也稳定,并且没有观察到散热器保护组合物变色。
表1
热板试验
染料 | C.I.号 | CAS号 | 加入量[ppm] | 试验结果 |
无 | --- | --- | --- | 白色残余物 |
C.I.活性紫5 | 18097 | 12226-38-9 | 50 | 白色残余物 |
C.I.碱性紫10 | 45170 | 81-88-9 | 50 | 红色残余物 |
C.I.酸性绿25 | 61570 | 4403-90-1 | 50 | 浅绿色残余物 |
C.I.酸性黄221 | 61814-59-3 | 50 | 黄色残余物 | |
C.I.酸性黄73 | 45350 | 518-47-8 | 50 | 黄棕色残余物 |
C.I.直接蓝86 | 74180 | 1330-38-7 | 50 | 兰绿色残余物 |
C.I.碱性紫1 | 42535 | 8004-87-3 | 50 | 兰色残余物 |
C.I.碱性紫3 | 42555 | 548-62-9 | 50 | 兰色残余物 |
表2
按照ASTM D 1384-97的玻璃器皿腐蚀试验
含有50ppm C.I.活性紫5的防冻浓缩物;浓度:33体积%
金属合金 | 重量变化[mg/cm2] |
+0.03 | |
软焊料 | +0.07 |
黄铜 | +0.03 |
钢 | +0.03 |
灰口铁 | +0.08 |
铸铝 | -0.02 |
试验前溶液的外观:紫色透明
试验后溶液的外观:紫色透明
表3
根据ASTMD 4340的传热腐蚀试验
含有50ppm C.I.活性紫5的防冻浓缩物;浓度:25体积%
金属合金: | 重量变化[mg/cm2/周] |
铸铝 | +0.36 |
i)试验前溶液的外观:紫色透明
j)试验后溶液的外观:紫色透明
Claims (8)
1.一种基于亚烷基二醇或其衍生物或基于甘油的防冻浓缩物,包含基于该浓缩物的总量为0.0005-0.1重量%的C.I.活性紫5染料。
2.如权利要求1所述的防冻浓缩物,除了所述染料外还包含下列化合物:
a)基于该浓缩物的总量为0.05-5重量%的一种或多种脂族、脂环族或芳族一元羧酸,其各自具有3-16个碳原子且呈其碱金属盐、铵盐或取代铵盐形式,和/或
b)基于该浓缩物的总量为0.05-5重量%的一种或多种脂族或芳族二-或三元羧酸,其各自具有3-21个碳原子且呈其碱金属盐、铵盐或取代铵盐形式,和/或
c)一种或多种碱金属硼酸盐、碱金属磷酸盐、碱金属硅酸盐、碱金属亚硝酸盐、碱金属或碱土金属硝酸盐、碱金属钼酸盐或碱金属或碱土金属氟化物,它们各自基于该浓缩物的总量为至多1重量%,和/或
d)基于该浓缩物的总量为0.05-5重量%的一种或多种具有2-15个碳原子且可以额外含有醚氧原子或羟基的脂族、脂环族或芳族胺,和/或
e)基于该浓缩物的总量为0.05-5重量%的一种或多种具有4-10个碳原子且可以苯并稠合和/或可以带有额外官能基团的单环或双环不饱和或部分不饱和杂环化合物,和/或
f)基于该浓缩物的总量为0.05-5重量%的一种或多种四(C1-C8-烷氧基)硅烷,和/或
g)基于该浓缩物的总量为0.05-10重量%的一种或多种羧酰胺和/或磺酰胺,和/或
h)基于该浓缩物的总量至多为1重量%的一种或多种硬水稳定剂,该稳定剂基于聚丙烯酸、聚马来酸、丙烯酸-马来酸共聚物、聚乙烯基吡咯烷酮、聚乙烯基咪唑、乙烯基吡咯烷酮-乙烯基咪唑共聚物和/或不饱和羧酸和烯烃的共聚物。
3.如权利要求2所述的防冻浓缩物,除了所述染料外还包含各自为0.05-5重量%的两种选自a)组和/或b)组且互不相同的羧酸和0.05-5重量%的一种或多种选自e)组的杂环化合物。
4.如权利要求1-3中任一项所述的防冻浓缩物,其pH为4-11。
5.如权利要求1-3中任一项所述的防冻浓缩物,基于乙二醇或丙二醇或乙二醇和丙二醇的混合物或甘油与乙二醇或丙二醇的混合物,在每种情况下包含至少95重量%的乙二醇和/或丙二醇和/或甘油。
6.一种制备如权利要求1-5中任一项所述的防冻浓缩物的方法,其中将C.I.活性紫5染料以基于该浓缩物的总量为0.0005-0.1重量%的量加入基于亚烷基二醇或其衍生物或基于甘油的防冻浓缩物中。
7.一种冰点降低的即可使用的含水冷却剂组合物,包含水和10-90重量%的如权利要求1-5中任一项所述的防冻浓缩物。
8.如权利要求1-5中任一项所述的防冻浓缩物在制备内燃机用含水冷却剂组合物中的用途。
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DE50201627D1 (de) | 2004-12-30 |
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JP2004530017A (ja) | 2004-09-30 |
EP1390438A1 (de) | 2004-02-25 |
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WO2002090462A1 (de) | 2002-11-14 |
CA2445792C (en) | 2010-04-27 |
EP1390438B1 (de) | 2004-11-24 |
PL200841B1 (pl) | 2009-02-27 |
PL366454A1 (en) | 2005-02-07 |
BR0209293B1 (pt) | 2012-06-26 |
HU229647B1 (en) | 2014-03-28 |
ES2233830T3 (es) | 2005-06-16 |
US6818147B2 (en) | 2004-11-16 |
SK286675B6 (sk) | 2009-03-05 |
MXPA03009001A (es) | 2004-02-12 |
ZA200309538B (en) | 2005-02-23 |
CN1507486A (zh) | 2004-06-23 |
CZ299952B6 (cs) | 2009-01-07 |
CZ20032949A3 (cs) | 2004-02-18 |
NO333717B1 (no) | 2013-09-02 |
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