CA1057744A - Produits comprenant des composes photographiques fixes positifs - Google Patents

Produits comprenant des composes photographiques fixes positifs

Info

Publication number: CA1057744A
Authority: CA; Canada
Prior art keywords: dye; compound; moiety; group; image
Prior art date: 1973-01-26
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA310,053A

Other languages

English (en)

Inventor

Paul B. Condit

Jerald C. Hinshaw

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Eastman Kodak Co

Original Assignee

Eastman Kodak Co

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1973-01-26

Filing date

1978-08-25

Publication date

1979-07-03

1974-01-15 Priority claimed from CA190,141A external-priority patent/CA1052610A/fr

1978-08-25 Application filed by Eastman Kodak Co filed Critical Eastman Kodak Co

1978-08-25 Priority to CA310,053A priority Critical patent/CA1057744A/fr

1979-07-03 Application granted granted Critical

1979-07-03 Publication of CA1057744A publication Critical patent/CA1057744A/fr

Status Expired legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 201
-1 silver halide Chemical class 0.000 claims abstract description 102
229910052709 silver Inorganic materials 0.000 claims abstract description 97
239000004332 silver Substances 0.000 claims abstract description 97
239000000839 emulsion Substances 0.000 claims abstract description 65
239000000463 material Substances 0.000 claims abstract description 55
238000006243 chemical reaction Methods 0.000 claims abstract description 40
239000003795 chemical substances by application Substances 0.000 claims abstract description 39
238000000034 method Methods 0.000 claims abstract description 33
239000002243 precursor Substances 0.000 claims abstract description 28
230000008569 process Effects 0.000 claims abstract description 20
230000000269 nucleophilic effect Effects 0.000 claims description 74
239000000203 mixture Substances 0.000 claims description 66
238000011161 development Methods 0.000 claims description 43
230000018109 developmental process Effects 0.000 claims description 43
238000012545 processing Methods 0.000 claims description 36
238000006073 displacement reaction Methods 0.000 claims description 34
125000004429 atom Chemical group 0.000 claims description 31
238000007254 oxidation reaction Methods 0.000 claims description 14
125000004432 carbon atom Chemical group C* 0.000 claims description 11
230000003647 oxidation Effects 0.000 claims description 11
230000000694 effects Effects 0.000 claims description 9
125000003118 aryl group Chemical group 0.000 claims description 8
239000003112 inhibitor Substances 0.000 claims description 8
239000000126 substance Substances 0.000 claims description 6
FUAXXVSVFLEVSF-UHFFFAOYSA-N 1h-2,1-benzoxazol-3-one Chemical group C1=CC=C2C(=O)ONC2=C1 FUAXXVSVFLEVSF-UHFFFAOYSA-N 0.000 claims description 5
238000009826 distribution Methods 0.000 claims description 5
125000000962 organic group Chemical group 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims description 4
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
239000007800 oxidant agent Substances 0.000 claims description 4
125000004430 oxygen atom Chemical group O* 0.000 claims description 4
230000000737 periodic effect Effects 0.000 claims description 4
230000001590 oxidative effect Effects 0.000 claims description 3
125000003277 amino group Chemical group 0.000 claims description 2
229910052717 sulfur Inorganic materials 0.000 claims description 2
230000007062 hydrolysis Effects 0.000 claims 1
238000006460 hydrolysis reaction Methods 0.000 claims 1
125000004434 sulfur atom Chemical group 0.000 claims 1
239000007795 chemical reaction product Substances 0.000 abstract description 3
239000010410 layer Substances 0.000 description 137
239000000975 dye Substances 0.000 description 106
229940009188 silver Drugs 0.000 description 88
239000000243 solution Substances 0.000 description 72
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 50
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
108010010803 Gelatin Proteins 0.000 description 33
239000008273 gelatin Substances 0.000 description 33
229920000159 gelatin Polymers 0.000 description 33
235000019322 gelatine Nutrition 0.000 description 33
235000011852 gelatine desserts Nutrition 0.000 description 33
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical class CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 26
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 25
239000000047 product Substances 0.000 description 25
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 25
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 24
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 22
239000007787 solid Substances 0.000 description 22
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
229910052757 nitrogen Inorganic materials 0.000 description 20
CWNSVVHTTQBGQB-UHFFFAOYSA-N N,N-Diethyldodecanamide Chemical compound CCCCCCCCCCCC(=O)N(CC)CC CWNSVVHTTQBGQB-UHFFFAOYSA-N 0.000 description 18
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 18
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 17
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
238000012546 transfer Methods 0.000 description 15
239000002253 acid Substances 0.000 description 13
230000006870 function Effects 0.000 description 13
239000003921 oil Substances 0.000 description 13
239000002244 precipitate Substances 0.000 description 13
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
239000000706 filtrate Substances 0.000 description 11
238000002360 preparation method Methods 0.000 description 11
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 10
230000002378 acidificating effect Effects 0.000 description 10
238000007792 addition Methods 0.000 description 10
229920000642 polymer Polymers 0.000 description 10
239000011541 reaction mixture Substances 0.000 description 10
229940076134 benzene Drugs 0.000 description 9
238000003776 cleavage reaction Methods 0.000 description 9
OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 9
230000007017 scission Effects 0.000 description 9
239000000741 silica gel Substances 0.000 description 9
229910002027 silica gel Inorganic materials 0.000 description 9
238000003756 stirring Methods 0.000 description 9
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 8
229910000041 hydrogen chloride Inorganic materials 0.000 description 8
229960005419 nitrogen Drugs 0.000 description 8
CMCWWLVWPDLCRM-UHFFFAOYSA-N phenidone Chemical compound N1C(=O)CCN1C1=CC=CC=C1 CMCWWLVWPDLCRM-UHFFFAOYSA-N 0.000 description 8
238000010992 reflux Methods 0.000 description 8
ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 8
MRIBCCHYZOSDOM-UHFFFAOYSA-N 3-(1-phenyltetrazol-5-yl)sulfanylpropanenitrile Chemical compound N#CCCSC1=NN=NN1C1=CC=CC=C1 MRIBCCHYZOSDOM-UHFFFAOYSA-N 0.000 description 7
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 7
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 7
235000013350 formula milk Nutrition 0.000 description 7
235000011118 potassium hydroxide Nutrition 0.000 description 7
229940093932 potassium hydroxide Drugs 0.000 description 7
239000002904 solvent Substances 0.000 description 7
238000012360 testing method Methods 0.000 description 7
WTUWTDFYNGZJAO-UHFFFAOYSA-N 3-oxo-1h-2,1-benzoxazole-5,7-dicarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C2NOC(=O)C2=C1 WTUWTDFYNGZJAO-UHFFFAOYSA-N 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 6
229940081735 acetylcellulose Drugs 0.000 description 6
239000007864 aqueous solution Substances 0.000 description 6
125000004122 cyclic group Chemical group 0.000 description 6
238000001914 filtration Methods 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
239000002002 slurry Substances 0.000 description 6
239000006188 syrup Substances 0.000 description 6
235000020357 syrup Nutrition 0.000 description 6
NWUNKFTVLXWQQC-UHFFFAOYSA-N 2,5-di(dodecan-2-yl)benzene-1,4-diol Chemical compound CCCCCCCCCCC(C)C1=CC(O)=C(C(C)CCCCCCCCCC)C=C1O NWUNKFTVLXWQQC-UHFFFAOYSA-N 0.000 description 5
DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 5
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
150000007513 acids Chemical class 0.000 description 5
229920002678 cellulose Polymers 0.000 description 5
229920002301 cellulose acetate Polymers 0.000 description 5
150000002148 esters Chemical class 0.000 description 5
NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 5
230000005855 radiation Effects 0.000 description 5
239000000837 restrainer Substances 0.000 description 5
238000000926 separation method Methods 0.000 description 5
229940086542 triethylamine Drugs 0.000 description 5
QLDQYRDCPNBPII-UHFFFAOYSA-N 1,2-benzoxazol-3-one Chemical group C1=CC=C2C(O)=NOC2=C1 QLDQYRDCPNBPII-UHFFFAOYSA-N 0.000 description 4
OBTZDIRUQWFRFZ-UHFFFAOYSA-N 2-(5-methylfuran-2-yl)-n-(4-methylphenyl)quinoline-4-carboxamide Chemical compound O1C(C)=CC=C1C1=CC(C(=O)NC=2C=CC(C)=CC=2)=C(C=CC=C2)C2=N1 OBTZDIRUQWFRFZ-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
239000004354 Hydroxyethyl cellulose Substances 0.000 description 4
229920000663 Hydroxyethyl cellulose Polymers 0.000 description 4
239000004372 Polyvinyl alcohol Substances 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
239000003513 alkali Substances 0.000 description 4
239000012670 alkaline solution Substances 0.000 description 4
229960001040 ammonium chloride Drugs 0.000 description 4
229940095564 anhydrous calcium sulfate Drugs 0.000 description 4
TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 4
239000011230 binding agent Substances 0.000 description 4
239000006229 carbon black Substances 0.000 description 4
239000001913 cellulose Substances 0.000 description 4
235000010980 cellulose Nutrition 0.000 description 4
239000011248 coating agent Substances 0.000 description 4
238000000576 coating method Methods 0.000 description 4
239000000084 colloidal system Substances 0.000 description 4
239000012043 crude product Substances 0.000 description 4
239000007789 gas Substances 0.000 description 4
229910052739 hydrogen Inorganic materials 0.000 description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
235000019447 hydroxyethyl cellulose Nutrition 0.000 description 4
238000009740 moulding (composite fabrication) Methods 0.000 description 4
KVKFRMCSXWQSNT-UHFFFAOYSA-N n,n'-dimethylethane-1,2-diamine Chemical compound CNCCNC KVKFRMCSXWQSNT-UHFFFAOYSA-N 0.000 description 4
125000004433 nitrogen atom Chemical group N* 0.000 description 4
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
229920002451 polyvinyl alcohol Polymers 0.000 description 4
IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 4
238000006479 redox reaction Methods 0.000 description 4
BOUYXKZEBJHJBT-UHFFFAOYSA-N 2-nitrobenzene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C([N+]([O-])=O)C(C(O)=O)=C1 BOUYXKZEBJHJBT-UHFFFAOYSA-N 0.000 description 3
FJWJYHHBUMICTP-UHFFFAOYSA-N 4,4-dimethylpyrazolidin-3-one Chemical compound CC1(C)CNNC1=O FJWJYHHBUMICTP-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
125000002252 acyl group Chemical group 0.000 description 3
235000019270 ammonium chloride Nutrition 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
239000001768 carboxy methyl cellulose Substances 0.000 description 3
239000000284 extract Substances 0.000 description 3
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 3
SZEGKVHRCLBFKJ-UHFFFAOYSA-N n-methyloctadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCNC SZEGKVHRCLBFKJ-UHFFFAOYSA-N 0.000 description 3
239000012044 organic layer Substances 0.000 description 3
239000003208 petroleum Substances 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
229940093956 potassium carbonate Drugs 0.000 description 3
235000011181 potassium carbonates Nutrition 0.000 description 3
230000009467 reduction Effects 0.000 description 3
230000033458 reproduction Effects 0.000 description 3
239000004408 titanium dioxide Substances 0.000 description 3
229920002554 vinyl polymer Polymers 0.000 description 3
DNXBEWIRXOIDBT-UHFFFAOYSA-N 1-ethyl-3-oxo-2,1-benzoxazole-5,7-dicarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C2N(CC)OC(=O)C2=C1 DNXBEWIRXOIDBT-UHFFFAOYSA-N 0.000 description 2
LKPJFQPGACXXKG-UHFFFAOYSA-N 1-methyl-3-oxo-2,1-benzoxazole-5,7-dicarbonyl chloride Chemical compound ClC(=O)C1=CC(C(Cl)=O)=C2N(C)OC(=O)C2=C1 LKPJFQPGACXXKG-UHFFFAOYSA-N 0.000 description 2
ZAJAQTYSTDTMCU-UHFFFAOYSA-N 3-aminobenzenesulfonic acid Chemical compound NC1=CC=CC(S(O)(=O)=O)=C1 ZAJAQTYSTDTMCU-UHFFFAOYSA-N 0.000 description 2
MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 2
LPYUENQFPVNPHY-UHFFFAOYSA-N 3-methoxycatechol Chemical compound COC1=CC=CC(O)=C1O LPYUENQFPVNPHY-UHFFFAOYSA-N 0.000 description 2
XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 2
PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 2
WSTIGTOSMOZIOA-UHFFFAOYSA-N 5-[2-(dihexylamino)-2-oxoethoxy]-2-nitrobenzene-1,3-dicarboxylic acid Chemical compound CCCCCCN(CCCCCC)C(=O)COC1=CC(C(O)=O)=C([N+]([O-])=O)C(C(O)=O)=C1 WSTIGTOSMOZIOA-UHFFFAOYSA-N 0.000 description 2
ZBIBQNVRTVLOHQ-UHFFFAOYSA-N 5-aminonaphthalen-1-ol Chemical compound C1=CC=C2C(N)=CC=CC2=C1O ZBIBQNVRTVLOHQ-UHFFFAOYSA-N 0.000 description 2
QNVNLUSHGRBCLO-UHFFFAOYSA-N 5-hydroxybenzene-1,3-dicarboxylic acid Chemical compound OC(=O)C1=CC(O)=CC(C(O)=O)=C1 QNVNLUSHGRBCLO-UHFFFAOYSA-N 0.000 description 2
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 2
239000005995 Aluminium silicate Substances 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
239000001856 Ethyl cellulose Substances 0.000 description 2
ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 2
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 2
DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 2
239000004698 Polyethylene Substances 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
125000002015 acyclic group Chemical group 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
235000012211 aluminium silicate Nutrition 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
239000000987 azo dye Substances 0.000 description 2
AGXUVMPSUKZYDT-UHFFFAOYSA-L barium(2+);octadecanoate Chemical compound [Ba+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O AGXUVMPSUKZYDT-UHFFFAOYSA-L 0.000 description 2
239000002585 base Substances 0.000 description 2
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 2
238000009835 boiling Methods 0.000 description 2
230000005587 bubbling Effects 0.000 description 2
235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
239000008112 carboxymethyl-cellulose Substances 0.000 description 2
229940105329 carboxymethylcellulose Drugs 0.000 description 2
238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
230000008859 change Effects 0.000 description 2
229910052729 chemical element Inorganic materials 0.000 description 2
238000001816 cooling Methods 0.000 description 2
229920001577 copolymer Polymers 0.000 description 2
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230000002411 adverse Effects 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
125000005250 alkyl acrylate group Chemical group 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
150000008064 anhydrides Chemical group 0.000 description 1
125000000129 anionic group Chemical group 0.000 description 1
239000001000 anthraquinone dye Substances 0.000 description 1
150000004056 anthraquinones Chemical class 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
229960005070 ascorbic acid Drugs 0.000 description 1
239000011668 ascorbic acid Substances 0.000 description 1
230000000712 assembly Effects 0.000 description 1
238000000429 assembly Methods 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
159000000009 barium salts Chemical class 0.000 description 1
230000008901 benefit Effects 0.000 description 1
MIAUJDCQDVWHEV-UHFFFAOYSA-N benzene-1,2-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1S(O)(=O)=O MIAUJDCQDVWHEV-UHFFFAOYSA-N 0.000 description 1
CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 1
150000008316 benzisoxazoles Chemical class 0.000 description 1
ZYGHJZDHTFUPRJ-UHFFFAOYSA-N benzo-alpha-pyrone Natural products C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 1
AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 1
FBVWGJQBKANTDZ-UHFFFAOYSA-N benzyl n-ethyl-n-methylcarbamate;sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O.CCN(C)C(=O)OCC1=CC=CC=C1 FBVWGJQBKANTDZ-UHFFFAOYSA-N 0.000 description 1
230000000903 blocking effect Effects 0.000 description 1
238000005282 brightening Methods 0.000 description 1
235000010410 calcium alginate Nutrition 0.000 description 1
239000000648 calcium alginate Substances 0.000 description 1
229960002681 calcium alginate Drugs 0.000 description 1
OKHHGHGGPDJQHR-YMOPUZKJSA-L calcium;(2s,3s,4s,5s,6r)-6-[(2r,3s,4r,5s,6r)-2-carboxy-6-[(2r,3s,4r,5s,6r)-2-carboxylato-4,5,6-trihydroxyoxan-3-yl]oxy-4,5-dihydroxyoxan-3-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylate Chemical compound [Ca+2].O[C@@H]1[C@H](O)[C@H](O)O[C@@H](C([O-])=O)[C@H]1O[C@H]1[C@@H](O)[C@@H](O)[C@H](O[C@H]2[C@H]([C@@H](O)[C@H](O)[C@H](O2)C([O-])=O)O)[C@H](C(O)=O)O1 OKHHGHGGPDJQHR-YMOPUZKJSA-L 0.000 description 1
125000002837 carbocyclic group Chemical group 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
AJPXTSMULZANCB-UHFFFAOYSA-N chlorohydroquinone Chemical compound OC1=CC=C(O)C(Cl)=C1 AJPXTSMULZANCB-UHFFFAOYSA-N 0.000 description 1
239000003086 colorant Substances 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
229940000425 combination drug Drugs 0.000 description 1
230000002860 competitive effect Effects 0.000 description 1
239000008139 complexing agent Substances 0.000 description 1
239000000306 component Substances 0.000 description 1
235000008504 concentrate Nutrition 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
235000001671 coumarin Nutrition 0.000 description 1
150000004775 coumarins Chemical class 0.000 description 1
230000008878 coupling Effects 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
238000005859 coupling reaction Methods 0.000 description 1
238000004132 cross linking Methods 0.000 description 1
239000013058 crude material Substances 0.000 description 1
239000010779 crude oil Substances 0.000 description 1
239000003975 dentin desensitizing agent Substances 0.000 description 1
230000009034 developmental inhibition Effects 0.000 description 1
150000008050 dialkyl sulfates Chemical class 0.000 description 1
DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
229940008406 diethyl sulfate Drugs 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
238000009792 diffusion process Methods 0.000 description 1
LGYXRWVWVYPLAY-UHFFFAOYSA-N dimethyl 5-(2-chloro-2-oxoethoxy)-2-nitrobenzene-1,3-dicarboxylate Chemical compound COC(=O)C1=CC(OCC(Cl)=O)=CC(C(=O)OC)=C1[N+]([O-])=O LGYXRWVWVYPLAY-UHFFFAOYSA-N 0.000 description 1
SJAIXFGADYLQBS-UHFFFAOYSA-N dimethyl 5-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethoxy]-2-nitrobenzene-1,3-dicarboxylate Chemical compound C(C)(C)(C)OC(COC1=CC(=C(C(=C1)C(=O)OC)[N+](=O)[O-])C(=O)OC)=O SJAIXFGADYLQBS-UHFFFAOYSA-N 0.000 description 1
PQRIBRIROFCBQX-UHFFFAOYSA-N dimethyl 5-hydroxy-2-nitrobenzene-1,3-dicarboxylate Chemical compound COC(=O)C1=CC(O)=CC(C(=O)OC)=C1[N+]([O-])=O PQRIBRIROFCBQX-UHFFFAOYSA-N 0.000 description 1
IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 1
SDIXRDNYIMOKSG-UHFFFAOYSA-L disodium methyl arsenate Chemical compound [Na+].[Na+].C[As]([O-])([O-])=O SDIXRDNYIMOKSG-UHFFFAOYSA-L 0.000 description 1
229920001971 elastomer Polymers 0.000 description 1
238000005868 electrolysis reaction Methods 0.000 description 1
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
230000001747 exhibiting effect Effects 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
239000011521 glass Substances 0.000 description 1
150000004676 glycans Chemical class 0.000 description 1
VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 1
229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
150000002429 hydrazines Chemical class 0.000 description 1
ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
238000003384 imaging method Methods 0.000 description 1
JCYWCSGERIELPG-UHFFFAOYSA-N imes Chemical class CC1=CC(C)=CC(C)=C1N1C=CN(C=2C(=CC(C)=CC=2C)C)[C]1 JCYWCSGERIELPG-UHFFFAOYSA-N 0.000 description 1
150000002466 imines Chemical class 0.000 description 1
230000037120 immobility Effects 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
230000003993 interaction Effects 0.000 description 1
238000003402 intramolecular cyclocondensation reaction Methods 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
150000002596 lactones Chemical group 0.000 description 1
239000004816 latex Substances 0.000 description 1
229920000126 latex Polymers 0.000 description 1
230000031700 light absorption Effects 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000002932 luster Substances 0.000 description 1
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
150000002678 macrocyclic compounds Chemical class 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
DZVCFNFOPIZQKX-LTHRDKTGSA-M merocyanine Chemical compound [Na+].O=C1N(CCCC)C(=O)N(CCCC)C(=O)C1=C\C=C\C=C/1N(CCCS([O-])(=O)=O)C2=CC=CC=C2O\1 DZVCFNFOPIZQKX-LTHRDKTGSA-M 0.000 description 1
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
CXKWCBBOMKCUKX-UHFFFAOYSA-M methylene blue Chemical compound [Cl-].C1=CC(N(C)C)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 CXKWCBBOMKCUKX-UHFFFAOYSA-M 0.000 description 1
GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
229960000907 methylthioninium chloride Drugs 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
CURJNMSGPBXOGK-UHFFFAOYSA-N n',n'-di(propan-2-yl)ethane-1,2-diamine Chemical compound CC(C)N(C(C)C)CCN CURJNMSGPBXOGK-UHFFFAOYSA-N 0.000 description 1
JFUCOPIALLYRGN-UHFFFAOYSA-N n,n-dihexylacetamide Chemical compound CCCCCCN(C(C)=O)CCCCCC JFUCOPIALLYRGN-UHFFFAOYSA-N 0.000 description 1
YKCHZHCCPAEVIN-UHFFFAOYSA-N n-(5-hydroxynaphthalen-1-yl)methanesulfonamide Chemical compound C1=CC=C2C(NS(=O)(=O)C)=CC=CC2=C1O YKCHZHCCPAEVIN-UHFFFAOYSA-N 0.000 description 1
WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
PXSXRABJBXYMFT-UHFFFAOYSA-N n-hexylhexan-1-amine Chemical compound CCCCCCNCCCCCC PXSXRABJBXYMFT-UHFFFAOYSA-N 0.000 description 1
150000002790 naphthalenes Chemical class 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
150000002828 nitro derivatives Chemical class 0.000 description 1
229920001220 nitrocellulos Polymers 0.000 description 1
239000012038 nucleophile Substances 0.000 description 1
239000003605 opacifier Substances 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
238000006053 organic reaction Methods 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
UWBHMRBRLOJJAA-UHFFFAOYSA-N oxaluric acid Chemical compound NC(=O)NC(=O)C(O)=O UWBHMRBRLOJJAA-UHFFFAOYSA-N 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
SOQBVABWOPYFQZ-UHFFFAOYSA-N oxygen(2-);titanium(4+) Chemical compound [O-2].[O-2].[Ti+4] SOQBVABWOPYFQZ-UHFFFAOYSA-N 0.000 description 1
239000008188 pellet Substances 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
150000004986 phenylenediamines Chemical class 0.000 description 1
239000000049 pigment Substances 0.000 description 1
229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 1
229920002401 polyacrylamide Polymers 0.000 description 1
239000004584 polyacrylic acid Substances 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
229920006289 polycarbonate film Polymers 0.000 description 1
239000005020 polyethylene terephthalate Substances 0.000 description 1
229920001155 polypropylene Polymers 0.000 description 1
229920001282 polysaccharide Polymers 0.000 description 1
239000005017 polysaccharide Substances 0.000 description 1
229920000136 polysorbate Polymers 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
229940005642 polystyrene sulfonic acid Drugs 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
235000007686 potassium Nutrition 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229960003975 potassium Drugs 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
238000010944 pre-mature reactiony Methods 0.000 description 1
150000003142 primary aromatic amines Chemical class 0.000 description 1
230000002633 protecting effect Effects 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
NDGRWYRVNANFNB-UHFFFAOYSA-N pyrazolidin-3-one Chemical class O=C1CCNN1 NDGRWYRVNANFNB-UHFFFAOYSA-N 0.000 description 1
MCSKRVKAXABJLX-UHFFFAOYSA-N pyrazolo[3,4-d]triazole Chemical compound N1=NN=C2N=NC=C21 MCSKRVKAXABJLX-UHFFFAOYSA-N 0.000 description 1
125000001453 quaternary ammonium group Chemical group 0.000 description 1
239000002516 radical scavenger Substances 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000012260 resinous material Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
229910052711 selenium Inorganic materials 0.000 description 1
ZUNKMNLKJXRCDM-UHFFFAOYSA-N silver bromoiodide Chemical compound [Ag].IBr ZUNKMNLKJXRCDM-UHFFFAOYSA-N 0.000 description 1
HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
KKDONKAYVYTWGY-UHFFFAOYSA-M sodium;2-(methylamino)ethanesulfonate Chemical compound [Na+].CNCCS([O-])(=O)=O KKDONKAYVYTWGY-UHFFFAOYSA-M 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000012265 solid product Substances 0.000 description 1
230000003381 solubilizing effect Effects 0.000 description 1
239000002195 soluble material Substances 0.000 description 1
241000894007 species Species 0.000 description 1
238000010183 spectrum analysis Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-M succinate(1-) Chemical compound OC(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-M 0.000 description 1
238000000967 suction filtration Methods 0.000 description 1
FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
125000000565 sulfonamide group Chemical group 0.000 description 1
125000000542 sulfonic acid group Chemical group 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
239000000725 suspension Substances 0.000 description 1
229920001059 synthetic polymer Polymers 0.000 description 1
238000003419 tautomerization reaction Methods 0.000 description 1
150000003568 thioethers Chemical class 0.000 description 1
ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 1
150000003918 triazines Chemical class 0.000 description 1
150000003852 triazoles Chemical class 0.000 description 1
239000006097 ultraviolet radiation absorber Substances 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920003176 water-insoluble polymer Polymers 0.000 description 1
230000003245 working effect Effects 0.000 description 1

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Silver Salt Photography Or Processing Solution Therefor (AREA)

CA310,053A 1973-01-26 1978-08-25 Produits comprenant des composes photographiques fixes positifs Expired CA1057744A (fr)

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CA310,053A CA1057744A (fr)	1973-01-26	1978-08-25	Produits comprenant des composes photographiques fixes positifs

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Application Number	Priority Date	Filing Date	Title
US32662873A	1973-01-26	1973-01-26
CA190,141A CA1052610A (fr)	1973-01-26	1974-01-15	Composes photographiques immobiles a reaction positive et elements photographiques du meme type
CA310,053A CA1057744A (fr)	1973-01-26	1978-08-25	Produits comprenant des composes photographiques fixes positifs

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CA1057744A true CA1057744A (fr)	1979-07-03

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN111812188A (zh) *	2020-06-22	2020-10-23	中国地质科学院水文地质环境地质研究所	一种基于双路进样的地下水氯同位素质谱分析方法

1978
- 1978-08-25 CA CA310,053A patent/CA1057744A/fr not_active Expired

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN111812188A (zh) *	2020-06-22	2020-10-23	中国地质科学院水文地质环境地质研究所	一种基于双路进样的地下水氯同位素质谱分析方法

Publication	Publication Date	Title
US4108850A (en)	1978-08-22	Positive-working immobile photographic azo compounds
US4139379A (en)	1979-02-13	Photographic elements containing ballasted electron-accepting nucleophilic displacement compounds
US4232107A (en)	1980-11-04	Photographic material suited for use in diffusion transfer photography and method of diffusion transfer photography using such material
US4076529A (en)	1978-02-28	Photographic diffusion transfer films, processes and compositions with color moiety releasing compound
US4199355A (en)	1980-04-22	Positive-working immobile photographic compounds and photographic elements containing same
CA1052610A (fr)	1979-04-17	Composes photographiques immobiles a reaction positive et elements photographiques du meme type
US4139389A (en)	1979-02-13	Cleavable aromatic nitro compounds
US4199354A (en)	1980-04-22	Positive-working immobile photographic compounds and photographic elements containing same
CA1169054A (fr)	1984-06-12	Produits et procedes photographiques utilisant de nouveaux composes non diffusibles a base d'arylazo- 6-pyridinol-3, liberateurs de couleur magenta, et leurs precurseurs
US4562139A (en)	1985-12-31	Photographic products employing novel nondiffusible metal complexes of azo dyes
US4255510A (en)	1981-03-10	Development restrainer precursors for photographic elements
US4358532A (en)	1982-11-09	Photographic element
EP0059269B1 (fr)	1985-05-22	Eléments photographiques contenant des colorants bloqués ou des composés bloqués libérant des colorants et procédés pour leur utilisation
US4450223A (en)	1984-05-22	Diffusion transfer material and process
JPH0223856B2 (fr)	1990-05-25
JPS6156500B2 (fr)	1986-12-02
US3931144A (en)	1976-01-06	Magenta image-providing phenylazonaphthyl dyes
US4407931A (en)	1983-10-04	Photographic products and processes employing nondiffusible yellow azo metal complexed dye-releasing compounds and precursors thereof
CA1057744A (fr)	1979-07-03	Produits comprenant des composes photographiques fixes positifs
GB1593728A (en)	1981-07-22	Photographic light-sensitive sheet material for the colour diffusion transfer process
US4346161A (en)	1982-08-24	Photographic products and processes employing novel nondiffusible 6-(2-thienylazo)-3-pyridinol cyan dye-releasing compounds and precursors thereof
US4278598A (en)	1981-07-14	Positive-working immobile intramolecular nucleophilic displacement compounds and photographic elements containing same
JPH0234374B2 (fr)	1990-08-02
US4471045A (en)	1984-09-11	4-Hydroxyalkyl-substituted 3-pyrazolidinone electron transfer agents
US4537853A (en)	1985-08-27	Photographic silver halide material containing a ballasted electron-donor precursor compound

CA1057744A - Produits comprenant des composes photographiques fixes positifs - Google Patents

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Applications Claiming Priority (3)

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ID=27163268

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Cited By (1)

Cited By (1)

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