CA1124960A - Composition d'un modificateur pour pigments azoiques, a base d'acide 2-hydroxy-3-naphtoique - Google Patents

Composition d'un modificateur pour pigments azoiques, a base d'acide 2-hydroxy-3-naphtoique

Info

Publication number: CA1124960A
Authority: CA; Canada
Prior art keywords: hydroxy; naphthoic acid; pigment; acid; percent
Prior art date: 1980-02-18
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

CA345,853A

Other languages

English (en)

Inventor

David R. Burley

Christopher J. Brookes

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.)

Wyeth Holdings LLC

Original Assignee

American Cyanamid 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.)

1980-02-18

Filing date

1980-02-18

Publication date

1982-06-08

1980-02-18 Application filed by American Cyanamid Co filed Critical American Cyanamid Co

1980-02-18 Priority to CA345,853A priority Critical patent/CA1124960A/fr

1982-06-08 Application granted granted Critical

1982-06-08 Publication of CA1124960A publication Critical patent/CA1124960A/fr

Status Expired legal-status Critical Current

Links

239000000049 pigment Substances 0.000 title claims description 53
ALKYHXVLJMQRLQ-UHFFFAOYSA-N 3-Hydroxy-2-naphthoate Chemical compound C1=CC=C2C=C(O)C(C(=O)O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-N 0.000 title claims description 45
239000000203 mixture Substances 0.000 title claims description 31
239000003607 modifier Substances 0.000 title description 19
230000008878 coupling Effects 0.000 claims abstract description 15
238000010168 coupling process Methods 0.000 claims abstract description 15
238000005859 coupling reaction Methods 0.000 claims abstract description 15
-1 alpha-substituted-2-hydroxy-3-naphthoic acids Chemical class 0.000 claims abstract description 8
238000000034 method Methods 0.000 claims description 18
230000003647 oxidation Effects 0.000 claims description 11
238000007254 oxidation reaction Methods 0.000 claims description 11
238000002360 preparation method Methods 0.000 claims description 11
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 9
150000001875 compounds Chemical class 0.000 claims description 7
FGPKSIXNTNDIJT-UHFFFAOYSA-N 4-chloro-3-hydroxynaphthalene-2-carboxylic acid Chemical compound C1=CC=C2C(Cl)=C(O)C(C(=O)O)=CC2=C1 FGPKSIXNTNDIJT-UHFFFAOYSA-N 0.000 claims description 5
IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 claims description 5
HBUFBIFPUAHIDX-UHFFFAOYSA-N 4-bromo-3-hydroxynaphthalene-2-carboxylic acid Chemical compound C1=CC=C2C(Br)=C(O)C(C(=O)O)=CC2=C1 HBUFBIFPUAHIDX-UHFFFAOYSA-N 0.000 claims description 4
229910021578 Iron(III) chloride Inorganic materials 0.000 claims description 4
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 4
125000003118 aryl group Chemical group 0.000 claims description 3
230000006872 improvement Effects 0.000 claims description 3
RUTXIHLAWFEWGM-UHFFFAOYSA-H iron(3+) sulfate Chemical compound [Fe+3].[Fe+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O RUTXIHLAWFEWGM-UHFFFAOYSA-H 0.000 claims description 3
229910000360 iron(III) sulfate Inorganic materials 0.000 claims description 3
150000002696 manganese Chemical class 0.000 claims description 3
229910052783 alkali metal Inorganic materials 0.000 claims description 2
150000001340 alkali metals Chemical class 0.000 claims description 2
GSSHBYZKCRYYID-UHFFFAOYSA-N 3-hydroxy-4-methylnaphthalene-2-carboxylic acid Chemical compound C1=CC=C2C(C)=C(O)C(C(O)=O)=CC2=C1 GSSHBYZKCRYYID-UHFFFAOYSA-N 0.000 claims 2
WLAMQCOVSYQBOE-UHFFFAOYSA-N 3-hydroxy-4-nitronaphthalene-2-carboxylic acid Chemical compound C1=CC=C2C([N+]([O-])=O)=C(O)C(C(=O)O)=CC2=C1 WLAMQCOVSYQBOE-UHFFFAOYSA-N 0.000 claims 2
229910052784 alkaline earth metal Inorganic materials 0.000 claims 1
150000001342 alkaline earth metals Chemical class 0.000 claims 1
239000000987 azo dye Substances 0.000 abstract 1
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
239000000243 solution Substances 0.000 description 19
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 5
238000001914 filtration Methods 0.000 description 5
239000000047 product Substances 0.000 description 5
VRLPHBSFRWMMPW-UHFFFAOYSA-N 2-amino-4-chloro-5-methylbenzenesulfonic acid Chemical compound CC1=CC(S(O)(=O)=O)=C(N)C=C1Cl VRLPHBSFRWMMPW-UHFFFAOYSA-N 0.000 description 4
KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 4
229960000583 acetic acid Drugs 0.000 description 4
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
159000000007 calcium salts Chemical class 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
229940099800 pigment red 48 Drugs 0.000 description 4
239000000725 suspension Substances 0.000 description 4
KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 4
239000002023 wood Substances 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
239000011734 sodium Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
VYZCFAPUHSSYCC-UHFFFAOYSA-N 2-amino-5-chloro-4-methylbenzenesulfonic acid Chemical compound CC1=CC(N)=C(S(O)(=O)=O)C=C1Cl VYZCFAPUHSSYCC-UHFFFAOYSA-N 0.000 description 2
LTPSRQRIPCVMKQ-UHFFFAOYSA-N 2-amino-5-methylbenzenesulfonic acid Chemical compound CC1=CC=C(N)C(S(O)(=O)=O)=C1 LTPSRQRIPCVMKQ-UHFFFAOYSA-N 0.000 description 2
JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-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
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
239000000654 additive Substances 0.000 description 2
230000000996 additive effect Effects 0.000 description 2
229940063656 aluminum chloride Drugs 0.000 description 2
238000009835 boiling Methods 0.000 description 2
229910052791 calcium Inorganic materials 0.000 description 2
239000011575 calcium Substances 0.000 description 2
229960005069 calcium Drugs 0.000 description 2
235000001465 calcium Nutrition 0.000 description 2
239000001110 calcium chloride Substances 0.000 description 2
229910001628 calcium chloride Inorganic materials 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
239000007822 coupling agent Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
238000011156 evaluation Methods 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
235000014413 iron hydroxide Nutrition 0.000 description 2
NCNCGGDMXMBVIA-UHFFFAOYSA-L iron(ii) hydroxide Chemical compound [OH-].[OH-].[Fe+2] NCNCGGDMXMBVIA-UHFFFAOYSA-L 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
DHEQXMRUPNDRPG-UHFFFAOYSA-N strontium nitrate Chemical compound [Sr+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O DHEQXMRUPNDRPG-UHFFFAOYSA-N 0.000 description 2
LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 description 1
GWIAAIUASRVOIA-UHFFFAOYSA-N 2-aminonaphthalene-1-sulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(N)=CC=C21 GWIAAIUASRVOIA-UHFFFAOYSA-N 0.000 description 1
UOBYKYZJUGYBDK-UHFFFAOYSA-N 2-naphthoic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CC=C21 UOBYKYZJUGYBDK-UHFFFAOYSA-N 0.000 description 1
IUYPGBXHRROEGG-UHFFFAOYSA-N 3-amino-2-chlorobenzenesulfonic acid Chemical compound NC1=CC=CC(S(O)(=O)=O)=C1Cl IUYPGBXHRROEGG-UHFFFAOYSA-N 0.000 description 1
IOENKTGZOLKEMO-UHFFFAOYSA-N 3-hydroxynaphthalene-2-carboxylic acid Chemical compound OC1=CC2=CC=CC=C2C=C1C(=O)O.OC1=CC2=CC=CC=C2C=C1C(=O)O IOENKTGZOLKEMO-UHFFFAOYSA-N 0.000 description 1
BTXXTMOWISPQSJ-UHFFFAOYSA-N 4,4,4-trifluorobutan-2-one Chemical compound CC(=O)CC(F)(F)F BTXXTMOWISPQSJ-UHFFFAOYSA-N 0.000 description 1
UXHQLGLGLZKHTC-CUNXSJBXSA-N 4-[(3s,3ar)-3-cyclopentyl-7-(4-hydroxypiperidine-1-carbonyl)-3,3a,4,5-tetrahydropyrazolo[3,4-f]quinolin-2-yl]-2-chlorobenzonitrile Chemical compound C1CC(O)CCN1C(=O)C1=CC=C(C=2[C@@H]([C@H](C3CCCC3)N(N=2)C=2C=C(Cl)C(C#N)=CC=2)CC2)C2=N1 UXHQLGLGLZKHTC-CUNXSJBXSA-N 0.000 description 1
BQACOLQNOUYJCE-FYZZASKESA-N Abietic acid Natural products CC(C)C1=CC2=CC[C@]3(C)[C@](C)(CCC[C@@]3(C)C(=O)O)[C@H]2CC1 BQACOLQNOUYJCE-FYZZASKESA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
HFEFMUSTGZNOPY-UHFFFAOYSA-N OOOOOOOOOOOOOOOO Chemical compound OOOOOOOOOOOOOOOO HFEFMUSTGZNOPY-UHFFFAOYSA-N 0.000 description 1
HDYRYUINDGQKMC-UHFFFAOYSA-M acetyloxyaluminum;dihydrate Chemical compound O.O.CC(=O)O[Al] HDYRYUINDGQKMC-UHFFFAOYSA-M 0.000 description 1
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
229940009827 aluminum acetate Drugs 0.000 description 1
229910052788 barium Inorganic materials 0.000 description 1
DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
WDIHJSXYQDMJHN-UHFFFAOYSA-L barium chloride Chemical compound [Cl-].[Cl-].[Ba+2] WDIHJSXYQDMJHN-UHFFFAOYSA-L 0.000 description 1
229910001626 barium chloride Inorganic materials 0.000 description 1
159000000009 barium salts Chemical class 0.000 description 1
229950011260 betanaphthol Drugs 0.000 description 1
230000031709 bromination Effects 0.000 description 1
238000005893 bromination reaction Methods 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
239000003518 caustics Substances 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
230000001143 conditioned effect Effects 0.000 description 1
230000003750 conditioning effect Effects 0.000 description 1
238000006193 diazotization reaction Methods 0.000 description 1
239000012535 impurity Substances 0.000 description 1
VXWSFRMTBJZULV-UHFFFAOYSA-H iron(3+) sulfate hydrate Chemical compound O.[Fe+3].[Fe+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O VXWSFRMTBJZULV-UHFFFAOYSA-H 0.000 description 1
239000000463 material Substances 0.000 description 1
TWXDDNPPQUTEOV-FVGYRXGTSA-N methamphetamine hydrochloride Chemical compound Cl.CN[C@@H](C)CC1=CC=CC=C1 TWXDDNPPQUTEOV-FVGYRXGTSA-N 0.000 description 1
HVFSJXUIRWUHRG-UHFFFAOYSA-N oic acid Natural products C1CC2C3CC=C4CC(OC5C(C(O)C(O)C(CO)O5)O)CC(O)C4(C)C3CCC2(C)C1C(C)C(O)CC(C)=C(C)C(=O)OC1OC(COC(C)=O)C(O)C(O)C1OC(C(C1O)O)OC(COC(C)=O)C1OC1OC(CO)C(O)C(O)C1O HVFSJXUIRWUHRG-UHFFFAOYSA-N 0.000 description 1
239000002245 particle Substances 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
239000001054 red pigment Substances 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000011343 solid material Substances 0.000 description 1
239000012265 solid product Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
229910052712 strontium Inorganic materials 0.000 description 1
CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
159000000008 strontium salts Chemical class 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000011282 treatment Methods 0.000 description 1

Landscapes

Paints Or Removers (AREA)

CA345,853A 1980-02-18 1980-02-18 Composition d'un modificateur pour pigments azoiques, a base d'acide 2-hydroxy-3-naphtoique Expired CA1124960A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA345,853A CA1124960A (fr)	1980-02-18	1980-02-18	Composition d'un modificateur pour pigments azoiques, a base d'acide 2-hydroxy-3-naphtoique

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA345,853A CA1124960A (fr)	1980-02-18	1980-02-18	Composition d'un modificateur pour pigments azoiques, a base d'acide 2-hydroxy-3-naphtoique

Publications (1)

Publication Number	Publication Date
CA1124960A true CA1124960A (fr)	1982-06-08

Family

ID=4116262

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA345,853A Expired CA1124960A (fr)	1980-02-18	1980-02-18	Composition d'un modificateur pour pigments azoiques, a base d'acide 2-hydroxy-3-naphtoique

Country Status (1)

Country	Link
CA (1)	CA1124960A (fr)

1980
- 1980-02-18 CA CA345,853A patent/CA1124960A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1999-06-08	MKEX	Expiry

Publication	Publication Date	Title
US2993065A (en)	1961-07-18	Pigment and method of preparing same
US2166221A (en)	1939-07-18	Process for producing pigment titanates
EP0050313A1 (fr)	1982-04-28	Procédé de fabrication de granulés de pigment et leur utilisation
US4224221A (en)	1980-09-23	Modifier composition for azo pigments based on 2-hydroxy-3-naphthoic acid
CA1124960A (fr)	1982-06-08	Composition d'un modificateur pour pigments azoiques, a base d'acide 2-hydroxy-3-naphtoique
JPS598759A (ja)	1984-01-18	ピグメント・レツド５３：１の新規な結晶変態
US2821525A (en)	1958-01-28	Azo coloring matters
KR870000091B1 (ko)	1987-02-10	아조안료의 제조방법
US2694055A (en)	1954-11-09	Metallic azo pigments
KR910007083B1 (ko)	1991-09-16	아조 안료 제조방법
JPS60238368A (ja)	1985-11-27	アゾ顔料組成物
US4217273A (en)	1980-08-12	Process for azo pigments
US5102466A (en)	1992-04-07	Production of pigments
US2796415A (en)	1957-06-18	Red azo pigments of improved transparency
US2237768A (en)	1941-04-08	Production of azo colors
KR930010509B1 (ko)	1993-10-25	아조안료의 제조방법
US2694056A (en)	1954-11-09	Pigmentary substances of the azo type
US2117859A (en)	1938-05-17	New azo dye and color lakes and their production
JPS61126176A (ja)	1986-06-13	濃色のポリハロゲン化銅フタロシアニンの製法
US2598483A (en)	1952-05-27	Pigments from 2-chloro-5-aminoethylbenzene-4-sulfonic acid and beta naphthol
JPS6364474B2 (fr)	1988-12-12
JPH0546867B2 (fr)	1993-07-15
US4892968A (en)	1990-01-09	3,3'-Dichloro-4,4-diaminodiphenyl sulfonic acids
US4525217A (en)	1985-06-25	Process for preparing ferriferrocyanide pigments
US4400317A (en)	1983-08-23	Method of forming copper complexes of azo-dyestuffs using non-salt-forming copper (II) compounds