TWI507429B

TWI507429B - 聚合物鍵合之雙醯基膦氧化物

聚合物鍵合之雙醯基膦氧化物 Download PDF

Info

Publication number: TWI507429B
Authority: TW; Taiwan
Prior art keywords: bis; alkyl; polymer; oxide; hydrogen
Prior art date: 2009-07-06

Application number

TW099122046A

Other languages

English (en)

Chinese (zh)

Other versions

TW201111399A (en

Inventor

Hansjorg Grutzmacher

Timo Ott

Kurt Dietliker

Original Assignee

Basf Se

Priority date

2009-07-06

Filing date

2010-07-05

Publication date

2015-11-11

2010-07-05 Application filed by Basf Se filed Critical Basf Se

2011-04-01 Publication of TW201111399A publication Critical patent/TW201111399A/zh

2015-11-11 Application granted granted Critical

2015-11-11 Publication of TWI507429B publication Critical patent/TWI507429B/zh

Links

229920000642 polymer Polymers 0.000 title claims description 152
-1 bis-decylphosphine oxide compound Chemical class 0.000 claims description 132
238000002360 preparation method Methods 0.000 claims description 76
150000001875 compounds Chemical class 0.000 claims description 69
238000000034 method Methods 0.000 claims description 62
239000000203 mixture Substances 0.000 claims description 59
229910052739 hydrogen Inorganic materials 0.000 claims description 53
239000001257 hydrogen Substances 0.000 claims description 45
229920001577 copolymer Polymers 0.000 claims description 38
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 38
XJKCOLXPDGFOGQ-UHFFFAOYSA-N C1(=CC=CC=2C3=CC=CC=C3CC12)P(C1=CC=CC=2C3=CC=CC=C3CC12)=O Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)P(C1=CC=CC=2C3=CC=CC=C3CC12)=O XJKCOLXPDGFOGQ-UHFFFAOYSA-N 0.000 claims description 33
125000000524 functional group Chemical group 0.000 claims description 33
238000006243 chemical reaction Methods 0.000 claims description 30
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 28
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 27
239000000178 monomer Substances 0.000 claims description 25
238000006116 polymerization reaction Methods 0.000 claims description 24
125000000217 alkyl group Chemical group 0.000 claims description 21
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
XOQRLXHLTSYZBF-UHFFFAOYSA-N 1-decylphosphonoyldecane Chemical compound CCCCCCCCCCP(=O)CCCCCCCCCC XOQRLXHLTSYZBF-UHFFFAOYSA-N 0.000 claims description 19
230000015572 biosynthetic process Effects 0.000 claims description 19
150000002431 hydrogen Chemical class 0.000 claims description 18
239000004744 fabric Substances 0.000 claims description 17
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 16
239000000758 substrate Substances 0.000 claims description 16
229920001222 biopolymer Polymers 0.000 claims description 14
229910052751 metal Inorganic materials 0.000 claims description 14
239000002184 metal Substances 0.000 claims description 14
239000003054 catalyst Substances 0.000 claims description 12
230000003647 oxidation Effects 0.000 claims description 12
238000007254 oxidation reaction Methods 0.000 claims description 12
125000005010 perfluoroalkyl group Chemical group 0.000 claims description 12
229910052698 phosphorus Inorganic materials 0.000 claims description 12
125000003118 aryl group Chemical group 0.000 claims description 11
229920002554 vinyl polymer Polymers 0.000 claims description 11
239000000654 additive Substances 0.000 claims description 10
229910052799 carbon Inorganic materials 0.000 claims description 9
150000001768 cations Chemical class 0.000 claims description 9
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 9
125000004437 phosphorous atom Chemical group 0.000 claims description 9
229910000073 phosphorus hydride Inorganic materials 0.000 claims description 9
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 9
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 8
229910052794 bromium Inorganic materials 0.000 claims description 8
229910052801 chlorine Inorganic materials 0.000 claims description 8
229920000058 polyacrylate Polymers 0.000 claims description 8
229920000123 polythiophene Polymers 0.000 claims description 8
125000006832 (C1-C10) alkylene group Chemical group 0.000 claims description 7
125000000896 monocarboxylic acid group Chemical group 0.000 claims description 7
239000004793 Polystyrene Substances 0.000 claims description 6
229920002223 polystyrene Polymers 0.000 claims description 6
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 6
239000000412 dendrimer Substances 0.000 claims description 5
229920000736 dendritic polymer Polymers 0.000 claims description 5
229910052740 iodine Inorganic materials 0.000 claims description 5
229920000636 poly(norbornene) polymer Polymers 0.000 claims description 5
230000002194 synthesizing effect Effects 0.000 claims description 5
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
125000000753 cycloalkyl group Chemical group 0.000 claims description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
WSFJFIDCQBAQQZ-UHFFFAOYSA-N hydroxy(sulfido)phosphanium Chemical group S[PH2]=O WSFJFIDCQBAQQZ-UHFFFAOYSA-N 0.000 claims description 3
238000003384 imaging method Methods 0.000 claims description 3
229920001290 polyvinyl ester Polymers 0.000 claims description 3
239000007800 oxidant agent Substances 0.000 claims description 2
239000002245 particle Substances 0.000 claims description 2
238000005728 strengthening Methods 0.000 claims description 2
AVGTVQFKPVYWEW-UHFFFAOYSA-N C1(C=CC2=CC=CC=C12)P(C1C=CC2=CC=CC=C12)=O Chemical compound C1(C=CC2=CC=CC=C12)P(C1C=CC2=CC=CC=C12)=O AVGTVQFKPVYWEW-UHFFFAOYSA-N 0.000 claims 1
238000007306 functionalization reaction Methods 0.000 claims 1
125000003367 polycyclic group Chemical group 0.000 claims 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 105
239000000243 solution Substances 0.000 description 90
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 58
238000005160 1H NMR spectroscopy Methods 0.000 description 52
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 44
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 42
238000005481 NMR spectroscopy Methods 0.000 description 41
239000002904 solvent Substances 0.000 description 38
239000011734 sodium Substances 0.000 description 31
229920000742 Cotton Polymers 0.000 description 29
238000000576 coating method Methods 0.000 description 29
239000000047 product Substances 0.000 description 28
NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 26
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 25
239000011248 coating agent Substances 0.000 description 25
229910052708 sodium Inorganic materials 0.000 description 25
239000003921 oil Substances 0.000 description 24
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 23
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 22
DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 22
239000000463 material Substances 0.000 description 22
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 21
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 21
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 20
230000008569 process Effects 0.000 description 20
239000007858 starting material Substances 0.000 description 19
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
238000000607 proton-decoupled 31P nuclear magnetic resonance spectroscopy Methods 0.000 description 18
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 18
229920002678 cellulose Polymers 0.000 description 17
239000001913 cellulose Substances 0.000 description 17
AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 16
JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 16
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
238000001914 filtration Methods 0.000 description 15
239000000976 ink Substances 0.000 description 15
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
239000011541 reaction mixture Substances 0.000 description 15
238000003756 stirring Methods 0.000 description 15
238000007334 copolymerization reaction Methods 0.000 description 14
238000007639 printing Methods 0.000 description 14
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 14
238000003786 synthesis reaction Methods 0.000 description 14
239000012267 brine Substances 0.000 description 11
239000007788 liquid Substances 0.000 description 11
230000004048 modification Effects 0.000 description 11
238000012986 modification Methods 0.000 description 11
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 11
UHOVQNZJYSORNB-MZWXYZOWSA-N benzene-d6 Chemical compound [2H]C1=C([2H])C([2H])=C([2H])C([2H])=C1[2H] UHOVQNZJYSORNB-MZWXYZOWSA-N 0.000 description 10
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
125000002887 hydroxy group Chemical group [H]O* 0.000 description 10
238000004519 manufacturing process Methods 0.000 description 10
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 10
229910052753 mercury Inorganic materials 0.000 description 10
KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 10
239000002244 precipitate Substances 0.000 description 10
230000005855 radiation Effects 0.000 description 10
235000017557 sodium bicarbonate Nutrition 0.000 description 10
229910000030 sodium bicarbonate Inorganic materials 0.000 description 10
125000006850 spacer group Chemical group 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
239000000853 adhesive Substances 0.000 description 9
230000001070 adhesive effect Effects 0.000 description 9
238000001723 curing Methods 0.000 description 9
239000006185 dispersion Substances 0.000 description 9
229920005862 polyol Polymers 0.000 description 9
RNBKMOTVGAUZHX-UHFFFAOYSA-N CC1=C(C=P=CC2=C(C=C(C=C2C)C)C)C(=CC(=C1)C)C Chemical compound CC1=C(C=P=CC2=C(C=C(C=C2C)C)C)C(=CC(=C1)C)C RNBKMOTVGAUZHX-UHFFFAOYSA-N 0.000 description 8
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
239000004820 Pressure-sensitive adhesive Substances 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
239000012153 distilled water Substances 0.000 description 8
238000001035 drying Methods 0.000 description 8
239000000049 pigment Substances 0.000 description 8
229920000647 polyepoxide Polymers 0.000 description 8
229920000728 polyester Polymers 0.000 description 8
239000000843 powder Substances 0.000 description 8
229910052938 sodium sulfate Inorganic materials 0.000 description 8
235000011152 sodium sulphate Nutrition 0.000 description 8
125000001424 substituent group Chemical group 0.000 description 8
150000001412 amines Chemical class 0.000 description 7
239000000975 dye Substances 0.000 description 7
150000002148 esters Chemical class 0.000 description 7
235000019439 ethyl acetate Nutrition 0.000 description 7
239000000499 gel Substances 0.000 description 7
238000006068 polycondensation reaction Methods 0.000 description 7
150000003077 polyols Chemical class 0.000 description 7
229920005989 resin Polymers 0.000 description 7
239000011347 resin Substances 0.000 description 7
239000007787 solid Substances 0.000 description 7
RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 7
OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
239000011230 binding agent Substances 0.000 description 6
229910052802 copper Inorganic materials 0.000 description 6
239000010949 copper Substances 0.000 description 6
229920001519 homopolymer Polymers 0.000 description 6
OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 6
239000003999 initiator Substances 0.000 description 6
239000002609 medium Substances 0.000 description 6
TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 6
235000009518 sodium iodide Nutrition 0.000 description 6
239000000600 sorbitol Substances 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 5
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 5
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 5
QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 5
229910052782 aluminium Inorganic materials 0.000 description 5
PXXJHWLDUBFPOL-UHFFFAOYSA-N benzamidine Chemical group NC(=N)C1=CC=CC=C1 PXXJHWLDUBFPOL-UHFFFAOYSA-N 0.000 description 5
239000013078 crystal Substances 0.000 description 5
YYLGKUPAFFKGRQ-UHFFFAOYSA-N dimethyldiethoxysilane Chemical compound CCO[Si](C)(C)OCC YYLGKUPAFFKGRQ-UHFFFAOYSA-N 0.000 description 5
239000003995 emulsifying agent Substances 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
239000010410 layer Substances 0.000 description 5
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 5
230000003287 optical effect Effects 0.000 description 5
229920000768 polyamine Polymers 0.000 description 5
229920002635 polyurethane Polymers 0.000 description 5
239000004814 polyurethane Substances 0.000 description 5
150000003254 radicals Chemical class 0.000 description 5
239000000126 substance Substances 0.000 description 5
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 4
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 4
LNRIBIFTBJLRPN-UHFFFAOYSA-N C(CCCCCCCCC)[PH2]=O Chemical class C(CCCCCCCCC)[PH2]=O LNRIBIFTBJLRPN-UHFFFAOYSA-N 0.000 description 4
RDPDBQJEELSCHK-UHFFFAOYSA-N COC1=C(C=P=CC(C(OC)=CC=C2)=C2OC)C(OC)=CC=C1 Chemical compound COC1=C(C=P=CC(C(OC)=CC=C2)=C2OC)C(OC)=CC=C1 RDPDBQJEELSCHK-UHFFFAOYSA-N 0.000 description 4
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
239000005909 Kieselgur Substances 0.000 description 4
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 4
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 4
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 4
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
150000001252 acrylic acid derivatives Chemical class 0.000 description 4
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 4
125000004432 carbon atom Chemical group C* 0.000 description 4
125000004181 carboxyalkyl group Chemical group 0.000 description 4
150000001735 carboxylic acids Chemical class 0.000 description 4
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
150000002009 diols Chemical class 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
230000008020 evaporation Effects 0.000 description 4
229910052736 halogen Inorganic materials 0.000 description 4
239000004816 latex Substances 0.000 description 4
229920000126 latex Polymers 0.000 description 4
239000011976 maleic acid Substances 0.000 description 4
239000012454 non-polar solvent Substances 0.000 description 4
239000003208 petroleum Substances 0.000 description 4
239000011574 phosphorus Substances 0.000 description 4
235000015497 potassium bicarbonate Nutrition 0.000 description 4
229910000028 potassium bicarbonate Inorganic materials 0.000 description 4
239000011736 potassium bicarbonate Substances 0.000 description 4
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 4
238000006467 substitution reaction Methods 0.000 description 4
235000012431 wafers Nutrition 0.000 description 4
239000002023 wood Substances 0.000 description 4
DIIIISSCIXVANO-UHFFFAOYSA-N 1,2-Dimethylhydrazine Chemical compound CNNC DIIIISSCIXVANO-UHFFFAOYSA-N 0.000 description 3
VEFLKXRACNJHOV-UHFFFAOYSA-N 1,3-dibromopropane Chemical compound BrCCCBr VEFLKXRACNJHOV-UHFFFAOYSA-N 0.000 description 3
CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 3
GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
XUCDSAJGHUNEQS-UHFFFAOYSA-N CC1=CC(=C(C(=C1)C)C=P)C Chemical compound CC1=CC(=C(C(=C1)C)C=P)C XUCDSAJGHUNEQS-UHFFFAOYSA-N 0.000 description 3
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