GB648651A - Treatment of cellulose esters and ethers with imidazolidine derivatives to inhibit gas fading - Google Patents
Treatment of cellulose esters and ethers with imidazolidine derivatives to inhibit gas fadingInfo
- Publication number
- GB648651A GB648651A GB21426/48A GB2142648A GB648651A GB 648651 A GB648651 A GB 648651A GB 21426/48 A GB21426/48 A GB 21426/48A GB 2142648 A GB2142648 A GB 2142648A GB 648651 A GB648651 A GB 648651A
- Authority
- GB
- United Kingdom
- Prior art keywords
- imidazolidine
- phenyl
- dibenzyl
- methyl
- reaction
- Prior art date
- 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
Links
- 229920002678 cellulose Polymers 0.000 title abstract 3
- 229920003086 cellulose ether Polymers 0.000 title abstract 2
- 238000005562 fading Methods 0.000 title abstract 2
- 150000002461 imidazolidines Chemical class 0.000 title abstract 2
- 150000002170 ethers Chemical class 0.000 title 1
- -1 methoxyphenyl Chemical group 0.000 abstract 7
- 238000006243 chemical reaction Methods 0.000 abstract 5
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 abstract 4
- 229920002301 cellulose acetate Polymers 0.000 abstract 3
- 239000006185 dispersion Substances 0.000 abstract 3
- PQCMJEAYQOJNGZ-UHFFFAOYSA-N 1,3-bis(furan-2-ylmethyl)-2-phenylimidazolidine Chemical compound C1(=CC=CC=C1)C1N(CCN1CC1=CC=CO1)CC1=CC=CO1 PQCMJEAYQOJNGZ-UHFFFAOYSA-N 0.000 abstract 2
- ZRIPMKIKIZGQLM-UHFFFAOYSA-N 1,3-dibenzyl-2-(furan-2-yl)imidazolidine Chemical compound C=1C=CC=CC=1CN(C1C=2OC=CC=2)CCN1CC1=CC=CC=C1 ZRIPMKIKIZGQLM-UHFFFAOYSA-N 0.000 abstract 2
- DBFSGTXNKFBZCH-UHFFFAOYSA-N 1,3-dibenzyl-2-phenylimidazolidine Chemical compound C=1C=CC=CC=1CN(C1C=2C=CC=CC=2)CCN1CC1=CC=CC=C1 DBFSGTXNKFBZCH-UHFFFAOYSA-N 0.000 abstract 2
- WVKVIIZOIXEUDN-UHFFFAOYSA-N 1,3-diethyl-2-phenylimidazolidine Chemical compound CCN1CCN(CC)C1C1=CC=CC=C1 WVKVIIZOIXEUDN-UHFFFAOYSA-N 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- 125000001931 aliphatic group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 238000004043 dyeing Methods 0.000 abstract 2
- PGPVQYFVWZLFEP-UHFFFAOYSA-N 1,3-dibutyl-2-(2-chlorophenyl)imidazolidine Chemical compound ClC1=C(C=CC=C1)C1N(CCN1CCCC)CCCC PGPVQYFVWZLFEP-UHFFFAOYSA-N 0.000 abstract 1
- OWPSIYXUNCYYDB-UHFFFAOYSA-N 1,3-diethyl-2-methylimidazolidine Chemical compound CCN1CCN(CC)C1C OWPSIYXUNCYYDB-UHFFFAOYSA-N 0.000 abstract 1
- PAZPNGYXNBABCM-UHFFFAOYSA-N 1,4-bis(2-hydroxyethylamino)anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(NCCO)=CC=C2NCCO PAZPNGYXNBABCM-UHFFFAOYSA-N 0.000 abstract 1
- QOSTVEDABRQTSU-UHFFFAOYSA-N 1,4-bis(methylamino)anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(NC)=CC=C2NC QOSTVEDABRQTSU-UHFFFAOYSA-N 0.000 abstract 1
- JOIIEYIBZDNPMY-UHFFFAOYSA-N 1-(ethylamino)-4-(methylamino)anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(NC)=CC=C2NCC JOIIEYIBZDNPMY-UHFFFAOYSA-N 0.000 abstract 1
- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 abstract 1
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 abstract 1
- JAFISWGICQIWSA-UHFFFAOYSA-N 2-(1,3-dibenzylimidazolidin-2-yl)quinoline Chemical compound N1=C(C=CC2=CC=CC=C12)C1N(CCN1CC1=CC=CC=C1)CC1=CC=CC=C1 JAFISWGICQIWSA-UHFFFAOYSA-N 0.000 abstract 1
- XRXYETHFOIYPTR-UHFFFAOYSA-N 2-(4-bromophenyl)-1,3-bis[(4-methoxyphenyl)methyl]imidazolidine Chemical compound BrC1=CC=C(C=C1)C1N(CCN1CC1=CC=C(C=C1)OC)CC1=CC=C(C=C1)OC XRXYETHFOIYPTR-UHFFFAOYSA-N 0.000 abstract 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 239000007868 Raney catalyst Substances 0.000 abstract 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 abstract 1
- 229910000564 Raney nickel Inorganic materials 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 239000000987 azo dye Substances 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 235000010290 biphenyl Nutrition 0.000 abstract 1
- 239000004305 biphenyl Substances 0.000 abstract 1
- 125000006267 biphenyl group Chemical group 0.000 abstract 1
- 125000005997 bromomethyl group Chemical group 0.000 abstract 1
- 125000004799 bromophenyl group Chemical group 0.000 abstract 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 239000001913 cellulose Substances 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 125000000068 chlorophenyl group Chemical group 0.000 abstract 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 1
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 abstract 1
- 239000000975 dye Substances 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000002541 furyl group Chemical group 0.000 abstract 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000001041 indolyl group Chemical group 0.000 abstract 1
- 230000001939 inductive effect Effects 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 abstract 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- MJGFBOZCAJSGQW-UHFFFAOYSA-N mercury sodium Chemical compound [Na].[Hg] MJGFBOZCAJSGQW-UHFFFAOYSA-N 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 abstract 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000005936 piperidyl group Chemical group 0.000 abstract 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 125000000168 pyrrolyl group Chemical group 0.000 abstract 1
- 125000004151 quinonyl group Chemical group 0.000 abstract 1
- 229910001023 sodium amalgam Inorganic materials 0.000 abstract 1
- 125000005425 toluyl group Chemical group 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
- D06P1/64—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
- D06P1/642—Compounds containing nitrogen
- D06P1/6426—Heterocyclic compounds
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
Abstract
Substituted imidazolidines are prepared by the following series of reactions <FORM:0648651/IV (b)/1> in which R and R1 are aliphatic, aromatic or heterocyclic radicals. The first reaction is effected at 20 DEG to 120 DEG C. in the presence or absence of an inert solvent; the second reaction may be effected by electrolytic reduction, by means of sodium amalgam or by means of hydrogen in the presence of Raney nickel; the third reaction is preferably effected on the reaction product of the second reaction, at temperatures from room temperature to about 70 DEG C. R and R1 may be methyl, ethyl, propyl, isopropyl, butyl, isobutyl, amyl, isoamyl, hexyl, heptyl, dichloromethyl, bromomethyl, a -bromethyl, b -chlorethyl, a a -dichloropropyl, a b -dibromopropyl, a -chlorisopropyl,g - bromisobutyl, cyclohexyl, benzyl, phenyl ethyl, phenyl, naphthyl, diphenyl, chlorophenyl, 2,4-dichlorophenyl, bromophenyl, methoxyphenyl, ethoxyphenyl, toluyl, ethyl phenyl, 2,4-dimethylphenyl, isopropyl phenyl, furyl, thiofuryl, 5-methyl furyl, piperidyl, N-ethyl-piperidyl, quinonyl, quinaldyl, pyrrolyl and indolyl. The compounds, several of which are specified, must be free from groups inducing solubility in water.ALSO:The resistance of dyeings on cellulose ester or ether fibres to acid fading is enhanced by incorporating, before, during or after dyeing, an imidazolidine free from water-solubilizing groups and having the general formula <FORM:0648651/IV (c)/1> wherein both R's are alike and R and R1 are aliphatic, p aromatic or heterocyclic radicals. Suitable compounds specified are 2-furyl-1,3-dibenzyl imidazolidine, 2-phenyl-1,3-difurfuryl imidazolidine, 2-phenyl-1,3-dibenzyl imidazolidine, 2-phenyl-1,3-diethyl imidazolidine, 2-butyl-1,3-diquinaldyl imidazolidine, 2-quinolyl-1,3-dibenzyl imidazolidine, 2-pyrrolyl-1,3-di-(o-methyl)-toluyl imidazolidine, 2-o-chlorophenyl-1,3-dibutyl imidazolidine, 2-methyl-1,3-diethyl imidazolidine, 2 - naphthyl - 1,3 - di - (a - pyrrolyl methyl) imidazolidine, and 2-(p-bromophenyl)-1,3-di-(p-methoxybenzyl) imidazolidine, and many other alternatives for the radicals R and R1 are referred to. The process is particularly applied to the treatment of cellulose derivative fibres when dyes with aminoanthraquinone and certain azo dyes. In examples: (1) cellulose acetate silk is dyed with an aqueous dispersion of 2-furyl-1,3-dibenzyl imidazolidine and 1 - methylamino - 4 - ethylaminoanthraquinone; (2) and (5) cellulose acetate silk pre-dyed with 1,4-di-(monomethylamino)-anthraquinone is treated with an aqueous dispersion of 2-phenyl-1,3-difurfuryl imidazolidine or 2-butyl-1,3-diquinaldyl imidazolidine; (3) and (4) cellulose acetate silk is dyed with an aqueous dispersion of 2-phenyl-1,3-dibenzyl imidazolidine or 2-phenyl-1,3-diethyl imidazolidine and 1,4 - di - (monohydroxyethylamino) - anthraquinone.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US778749A US2525898A (en) | 1947-10-09 | 1947-10-09 | 1, 3-diphenylimidazolidine and certain derivatives thereof used as acid fading inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB648651A true GB648651A (en) | 1951-01-10 |
Family
ID=25114294
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB21426/48A Expired GB648651A (en) | 1947-10-09 | 1948-08-13 | Treatment of cellulose esters and ethers with imidazolidine derivatives to inhibit gas fading |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US2525898A (en) |
| BE (1) | BE484907A (en) |
| FR (1) | FR988496A (en) |
| GB (1) | GB648651A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4208182A (en) * | 1976-02-17 | 1980-06-17 | Toyo Ink Manufacturing Co., Ltd. | Process for transfer printing at elevated temperatures |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2762680A (en) * | 1952-10-02 | 1956-09-11 | Celanese Corp | Production of inhibitor gel compositions |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE369938A (en) * | 1929-06-25 | |||
| GB404940A (en) * | 1932-07-19 | 1934-01-19 | British Celanese | Improvements in or relating to the manufacture of artificial filaments, threads, films and the like |
| US2148655A (en) * | 1937-09-29 | 1939-02-28 | Celanese Corp | Coloration of textile materials |
| US2176506A (en) * | 1938-03-14 | 1939-10-17 | Eastman Kodak Co | Treatment of textile and other materials |
| US2255090A (en) * | 1940-02-13 | 1941-09-09 | Du Pont | Inhibiting the gas fading of dyed acetate silk |
| US2298401A (en) * | 1940-08-22 | 1942-10-13 | Eastman Kodak Co | Treatment of textile material |
| US2340375A (en) * | 1940-09-02 | 1944-02-01 | Ici Ltd | Treatment of cellulose esters and ethers |
| US2416380A (en) * | 1942-07-18 | 1947-02-25 | Ici Ltd | Inhibition of acid-fading on dyed cellulose acetate with n:n' diphenylethylene diamine |
-
0
- BE BE484907D patent/BE484907A/xx unknown
-
1947
- 1947-10-09 US US778749A patent/US2525898A/en not_active Expired - Lifetime
-
1948
- 1948-08-13 GB GB21426/48A patent/GB648651A/en not_active Expired
- 1948-09-02 FR FR988496D patent/FR988496A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4208182A (en) * | 1976-02-17 | 1980-06-17 | Toyo Ink Manufacturing Co., Ltd. | Process for transfer printing at elevated temperatures |
Also Published As
| Publication number | Publication date |
|---|---|
| US2525898A (en) | 1950-10-17 |
| BE484907A (en) | |
| FR988496A (en) | 1951-08-28 |
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