PL80662B1 - Process for preparing pigment compositions [gb1249912a] - Google Patents

Process for preparing pigment compositions [gb1249912a] Download PDF

Info

Publication number: PL80662B1
Authority: PL; Poland
Prior art keywords: radical; carbon atoms; amino; methyl; pattern
Prior art date: 1969-05-01

Application number

PL13952569A

Other languages

English (en)

Polish (pl)

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.)

1969-05-01

Filing date

1969-08-15

Publication date

1975-08-30

1969-08-15 Application filed filed Critical

1975-08-30 Publication of PL80662B1 publication Critical patent/PL80662B1/pl

Links

239000000203 mixture Substances 0.000 title abstract description 11
239000000049 pigment Substances 0.000 title abstract 8
238000004519 manufacturing process Methods 0.000 title 1
238000000034 method Methods 0.000 claims abstract description 23
150000003839 salts Chemical class 0.000 claims abstract description 6
-1 acyl radicals Chemical class 0.000 claims description 52
125000004432 carbon atom Chemical group C* 0.000 claims description 34
150000001875 compounds Chemical class 0.000 claims description 20
150000003254 radicals Chemical class 0.000 claims description 18
125000000217 alkyl group Chemical group 0.000 claims description 10
MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical group [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 9
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
125000004430 oxygen atom Chemical group O* 0.000 claims description 8
YWBFPKPWMSWWEA-UHFFFAOYSA-O triazolopyrimidine Chemical class BrC1=CC=CC(C=2N=C3N=CN[N+]3=C(NCC=3C=CN=CC=3)C=2)=C1 YWBFPKPWMSWWEA-UHFFFAOYSA-O 0.000 claims description 6
239000002253 acid Substances 0.000 claims description 5
125000005843 halogen group Chemical group 0.000 claims description 5
238000006243 chemical reaction Methods 0.000 claims description 4
239000002904 solvent Substances 0.000 claims description 4
125000003342 alkenyl group Chemical group 0.000 claims description 3
229910052799 carbon Inorganic materials 0.000 claims description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
239000000460 chlorine Substances 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
238000002360 preparation method Methods 0.000 claims description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
230000002378 acidificating effect Effects 0.000 claims 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
125000001309 chloro group Chemical group Cl* 0.000 claims 1
239000003085 diluting agent Substances 0.000 claims 1
229910052736 halogen Chemical group 0.000 claims 1
150000002367 halogens Chemical group 0.000 claims 1
TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical group [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 claims 1
229910052740 iodine Chemical group 0.000 claims 1
239000011630 iodine Chemical group 0.000 claims 1
229910052760 oxygen Inorganic materials 0.000 claims 1
239000001301 oxygen Substances 0.000 claims 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
239000006185 dispersion Substances 0.000 abstract description 14
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 abstract description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract description 2
229910052700 potassium Inorganic materials 0.000 abstract description 2
239000011591 potassium Substances 0.000 abstract description 2
229910052708 sodium Inorganic materials 0.000 abstract description 2
239000011734 sodium Substances 0.000 abstract description 2
102000011632 Caseins Human genes 0.000 abstract 6
108010076119 Caseins Proteins 0.000 abstract 6
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 4
BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 abstract 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 3
239000005018 casein Substances 0.000 abstract 3
235000021240 caseins Nutrition 0.000 abstract 3
229920000159 gelatin Polymers 0.000 abstract 3
235000019322 gelatine Nutrition 0.000 abstract 3
239000003292 glue Substances 0.000 abstract 3
239000001828 Gelatine Substances 0.000 abstract 2
235000013877 carbamide Nutrition 0.000 abstract 2
239000004202 carbamide Substances 0.000 abstract 2
230000001376 precipitating effect Effects 0.000 abstract 2
IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 abstract 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract 1
239000005977 Ethylene Substances 0.000 abstract 1
108010010803 Gelatin Proteins 0.000 abstract 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 1
239000012736 aqueous medium Substances 0.000 abstract 1
239000008346 aqueous phase Substances 0.000 abstract 1
JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 abstract 1
235000010233 benzoic acid Nutrition 0.000 abstract 1
150000001559 benzoic acids Chemical class 0.000 abstract 1
239000000969 carrier Substances 0.000 abstract 1
239000003795 chemical substances by application Substances 0.000 abstract 1
239000007859 condensation product Substances 0.000 abstract 1
239000002270 dispersing agent Substances 0.000 abstract 1
239000008273 gelatin Substances 0.000 abstract 1
235000011852 gelatine desserts Nutrition 0.000 abstract 1
229910052500 inorganic mineral Inorganic materials 0.000 abstract 1
239000001023 inorganic pigment Substances 0.000 abstract 1
229920005610 lignin Polymers 0.000 abstract 1
239000011707 mineral Substances 0.000 abstract 1
150000007522 mineralic acids Chemical class 0.000 abstract 1
PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 abstract 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
239000012860 organic pigment Substances 0.000 abstract 1
239000000843 powder Substances 0.000 abstract 1
239000003755 preservative agent Substances 0.000 abstract 1
150000003870 salicylic acids Chemical class 0.000 abstract 1
235000010413 sodium alginate Nutrition 0.000 abstract 1
229940005550 sodium alginate Drugs 0.000 abstract 1
239000000661 sodium alginate Substances 0.000 abstract 1
229940080237 sodium caseinate Drugs 0.000 abstract 1
159000000000 sodium salts Chemical class 0.000 abstract 1
239000002699 waste material Substances 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 12
229910000104 sodium hydride Inorganic materials 0.000 description 12
239000012312 sodium hydride Substances 0.000 description 12
CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
238000002425 crystallisation Methods 0.000 description 9
230000008025 crystallization Effects 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
238000002844 melting Methods 0.000 description 7
230000008018 melting Effects 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
238000010992 reflux Methods 0.000 description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 4
239000002585 base Substances 0.000 description 4
230000000694 effects Effects 0.000 description 4
QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 4
PKWIYNIDEDLDCJ-UHFFFAOYSA-N guanazole Chemical compound NC1=NNC(N)=N1 PKWIYNIDEDLDCJ-UHFFFAOYSA-N 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
239000007858 starting material Substances 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
208000009079 Bronchial Spasm Diseases 0.000 description 3
208000014181 Bronchial disease Diseases 0.000 description 3
206010006482 Bronchospasm Diseases 0.000 description 3
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
238000003756 stirring Methods 0.000 description 3
239000000725 suspension Substances 0.000 description 3
MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
229930194542 Keto Natural products 0.000 description 2
PMDCZENCAXMSOU-UHFFFAOYSA-N N-ethylacetamide Chemical compound CCNC(C)=O PMDCZENCAXMSOU-UHFFFAOYSA-N 0.000 description 2
208000008589 Obesity Diseases 0.000 description 2
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 description 2
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
238000009835 boiling Methods 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
239000003480 eluent Substances 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
238000001914 filtration Methods 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
125000000468 ketone group Chemical group 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
235000020824 obesity Nutrition 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
238000005406 washing Methods 0.000 description 2
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
WQWSMVWRGAFPJX-UHFFFAOYSA-N (3-amino-1h-1,2,4-triazol-5-yl)methanol Chemical compound NC1=NNC(CO)=N1 WQWSMVWRGAFPJX-UHFFFAOYSA-N 0.000 description 1
SWXXKWPYNMZFTE-UHFFFAOYSA-N (c-ethylsulfanylcarbonimidoyl)azanium;bromide Chemical compound Br.CCSC(N)=N SWXXKWPYNMZFTE-UHFFFAOYSA-N 0.000 description 1
GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
UPSXAPQYNGXVBF-UHFFFAOYSA-N 2-bromobutane Chemical compound CCC(C)Br UPSXAPQYNGXVBF-UHFFFAOYSA-N 0.000 description 1
IIVWHGMLFGNMOW-UHFFFAOYSA-N 2-methylpropane Chemical compound C[C](C)C IIVWHGMLFGNMOW-UHFFFAOYSA-N 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
BLNVISNJTIRAHF-UHFFFAOYSA-N 4-chlorobenzamide Chemical compound NC(=O)C1=CC=C(Cl)C=C1 BLNVISNJTIRAHF-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
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
102100022404 E3 ubiquitin-protein ligase Midline-1 Human genes 0.000 description 1
101710102210 E3 ubiquitin-protein ligase Midline-1 Proteins 0.000 description 1
IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical class CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 description 1
241000490229 Eucephalus Species 0.000 description 1
206010023644 Lacrimation increased Diseases 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 1
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
BQOWUDKEXDCGQS-UHFFFAOYSA-N [CH]1CCCC1 Chemical compound [CH]1CCCC1 BQOWUDKEXDCGQS-UHFFFAOYSA-N 0.000 description 1
210000000577 adipose tissue Anatomy 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
229910000102 alkali metal hydride Inorganic materials 0.000 description 1
150000008046 alkali metal hydrides Chemical class 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
125000004448 alkyl carbonyl group Chemical group 0.000 description 1
BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical compound [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 description 1
230000003266 anti-allergic effect Effects 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
WVDDGKGOMKODPV-UHFFFAOYSA-N benzyl alcohol Substances OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
206010006451 bronchitis Diseases 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000006114 decarboxylation reaction Methods 0.000 description 1
206010061428 decreased appetite Diseases 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000000428 dust Substances 0.000 description 1
238000010828 elution Methods 0.000 description 1
SSVFMICWXDVRQN-UHFFFAOYSA-N ethanol;sodium Chemical compound [Na].CCO SSVFMICWXDVRQN-UHFFFAOYSA-N 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
238000007429 general method Methods 0.000 description 1
FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
239000004922 lacquer Substances 0.000 description 1
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
UZJLYRRDVFWSGA-UHFFFAOYSA-N n-benzylacetamide Chemical compound CC(=O)NCC1=CC=CC=C1 UZJLYRRDVFWSGA-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000003880 negative regulation of appetite Effects 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
239000004533 oil dispersion Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
ORTFAQDWJHRMNX-UHFFFAOYSA-M oxidooxomethyl Chemical compound [O-][C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-M 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
230000002265 prevention Effects 0.000 description 1
239000000047 product Substances 0.000 description 1
230000000069 prophylactic effect Effects 0.000 description 1
229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
150000003230 pyrimidines Chemical class 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
239000000932 sedative agent Substances 0.000 description 1
230000001624 sedative effect Effects 0.000 description 1
239000013049 sediment Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
150000008634 thiazolopyrimidines Chemical class 0.000 description 1
150000003852 triazoles Chemical class 0.000 description 1
POFDSYGXHVPQNX-UHFFFAOYSA-N triazolo[1,5-a]pyrimidine Chemical compound C1=CC=NC2=CN=NN21 POFDSYGXHVPQNX-UHFFFAOYSA-N 0.000 description 1
LENLQGBLVGGAMF-UHFFFAOYSA-N tributyl([1,2,4]triazolo[1,5-a]pyridin-6-yl)stannane Chemical compound C1=C([Sn](CCCC)(CCCC)CCCC)C=CC2=NC=NN21 LENLQGBLVGGAMF-UHFFFAOYSA-N 0.000 description 1
229940070710 valerate Drugs 0.000 description 1
230000004580 weight loss Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/0092—Dyes in solid form

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Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Chemistry (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Pigments, Carbon Blacks, Or Wood Stains (AREA)

PL13952569A 1969-05-01 1969-08-15 Process for preparing pigment compositions [gb1249912a] PL80662B1 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB2226669		1969-05-01

Publications (1)

Publication Number	Publication Date
PL80662B1 true PL80662B1 (en)	1975-08-30

Family

ID=10176594

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
PL13952569A PL80662B1 (en)	1969-05-01	1969-08-15	Process for preparing pigment compositions [gb1249912a]
PL13952769A PL80664B1 (en)	1969-05-01	1969-08-15	Process for preparing pigment compositions [gb1249912a]

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
PL13952769A PL80664B1 (en)	1969-05-01	1969-08-15	Process for preparing pigment compositions [gb1249912a]

Country Status (5)

Country	Link
AT (2)	AT292696B (de)
CS (1)	CS163197B2 (de)
GB (1)	GB1249912A (de)
PL (2)	PL80662B1 (de)
SU (1)	SU432719A3 (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE19905269A1 (de)	1999-02-09	2000-08-10	Bayer Ag	Feste Pigmentpräparationen
GB2385594B (en) *	1999-02-09	2003-10-08	Bayer Ag	Solid pigment prepartions

1969
- 1969-01-02 GB GB26669A patent/GB1249912A/en not_active Expired
- 1969-08-15 PL PL13952569A patent/PL80662B1/pl unknown
- 1969-08-15 PL PL13952769A patent/PL80664B1/pl unknown
- 1969-09-02 SU SU1445877A patent/SU432719A3/ru active
- 1969-09-03 CS CS275669A patent/CS163197B2/cs unknown
- 1969-09-12 AT AT866770A patent/AT292696B/de not_active IP Right Cessation
- 1969-09-12 AT AT867070A patent/AT292699B/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
GB1249912A (en)	1971-10-13
CS163197B2 (de)	1975-08-29
AT292699B (de)	1971-09-10
SU432719A3 (ru)	1974-06-15
PL80664B1 (en)	1975-08-30
AT292696B (de)	1971-09-10

Publication	Publication Date	Title
WO1993016076A1 (en)	1993-08-19	3-(1h^_-tetrazol-5-yl)-4h^_-pyrido[1,2-a^_]pyrimidine-4-ones, pharmaceutical compositions containing the same and the preparation thereof
EP0018139B1 (de)	1983-05-04	Pyrido (2,3-d) pyrimidin-Derivate, sie enthaltende pharmazeutische Zusammensetzungen und Verfahren zur Herstellung der Pyrido (2,3-d) pyrimidin-Derivate
IL32992A (en)	1972-08-30	Triazolopyrimidine derivatives
PL80662B1 (en)	1975-08-30	Process for preparing pigment compositions [gb1249912a]
WO1995007265A1 (en)	1995-03-16	Improved process for preparing 2-amino-4,6-dichloropyrimidine
AU6036490A (en)	1991-02-22	Process for preparing 2,5-diamino-4,6-dichloropyrimidine
US4650892A (en)	1987-03-17	Process for the preparation of herbicidal sulfonamides
WO1995023153A1 (en)	1995-08-31	Quinolonylcarboxamidocephalosporin derivatives and pharmaceutical compositions containing them
AU676413B2 (en)	1997-03-06	5-alkoxy-1,2,4-triazolo(4,3-C)pyrimidine-3(2H)-thione compounds and their use in the preparation of 5-alkoxy(1,2,4)triazolo(1,5-C)pyrimidine-2(3H)-thione and 3-hydrocarbylthio-5-alkoxy-1,2,4-triazolo(4,3-C)pyrimidine compounds
PL123812B1 (en)	1982-11-30	Process for preparing novel derivatives of pyran-4-one
Hildick et al.	1971	Purines, pyrimidines, and imidazoles. Part XXXVII. Some new syntheses of pyrazolo [3, 4-d] pyrimidines, including allopurinol
US3773949A (en)	1973-11-20	Certain s-triazolo(1,5-a)pyrimidines for preventing bronchospasm or reducing body fat
US6455696B2 (en)	2002-09-24	Process for preparing 2,6-dichloropurine
US3525747A (en)	1970-08-25	Method for producing heterocyclic dicarboximides
US2963480A (en)	1960-12-06	6-pteridinehydrazine and amidrazone derivatives
PL80261B1 (en)	1975-08-30	New heterocyclic compounds[za6905832b]
EP0188225B1 (de)	1988-01-07	Verfahren zur Herstellung von herbiziden, sich von substituierten 2-Amino-1,2,4-triazolo(1,5-a)pyrimidinen ableitenden Sulfonamiden und hierbei vorgesehene neue Zwischenprodukte
Hamby et al.	1987	A comparison of nucleophilic reactions of 3‐benzenesulfonyloxyalloxazine and its 1‐methyl analog
EP0107165B1 (de)	1987-04-15	Substituierte 9H-8-Oxo-pyrimido(2,1-f)purin-2,4-dione, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Zubereitungen
US3251875A (en)	1966-05-17	N-nitroso derivatives
PL98547B1 (pl)	1978-05-31	Sposob wytwarzania amidow kwasu karboksylowego
Westerlund	1980	The synthetic utility of heteroaromatic azido compounds. Part VII. Preparation of some 2‐and 4‐substituted thieno [3, 2‐d] pyrimidines
PL80663B1 (de)	1975-08-30
Ismail et al.	1968	Pyridopyrimidines. Part IV. The preparation of pyrido [4, 3-d] pyrimidines from pryano [4, 3-d] pyrimidin-5-ones
CZ83394A3 (en)	1995-02-15	Novel derivatives of fluoroquinoline-3-carboxylic acid and process for preparing such derivatives