DE2134024B2 - Oberflaechenaktive verbindungen - Google Patents
Oberflaechenaktive verbindungenInfo
- Publication number
- DE2134024B2 DE2134024B2 DE19712134024 DE2134024A DE2134024B2 DE 2134024 B2 DE2134024 B2 DE 2134024B2 DE 19712134024 DE19712134024 DE 19712134024 DE 2134024 A DE2134024 A DE 2134024A DE 2134024 B2 DE2134024 B2 DE 2134024B2
- Authority
- DE
- Germany
- Prior art keywords
- amine
- ethylene oxide
- parts
- product
- condensate
- 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.)
- Pending
Links
- 150000001412 amines Chemical class 0.000 claims description 53
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 33
- 150000001875 compounds Chemical class 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 238000005984 hydrogenation reaction Methods 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- 150000003973 alkyl amines Chemical class 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 238000007278 cyanoethylation reaction Methods 0.000 claims 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 39
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- 239000000047 product Substances 0.000 description 35
- 238000000034 method Methods 0.000 description 18
- 229910052757 nitrogen Inorganic materials 0.000 description 17
- 239000003795 chemical substances by application Substances 0.000 description 16
- 239000000243 solution Substances 0.000 description 16
- 239000000203 mixture Substances 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 12
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 10
- 238000004043 dyeing Methods 0.000 description 9
- 239000000463 material Substances 0.000 description 7
- 229920001296 polysiloxane Polymers 0.000 description 7
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 239000000839 emulsion Substances 0.000 description 6
- 229920000126 latex Polymers 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- 239000002518 antifoaming agent Substances 0.000 description 5
- 239000004753 textile Substances 0.000 description 5
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 4
- 239000004312 hexamethylene tetramine Substances 0.000 description 4
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 4
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 4
- 239000004816 latex Substances 0.000 description 4
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- -1 alkali metal salts Chemical class 0.000 description 3
- 150000003863 ammonium salts Chemical class 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 150000003141 primary amines Chemical class 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 2
- YCOXTKKNXUZSKD-UHFFFAOYSA-N 3,4-xylenol Chemical compound CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 239000004677 Nylon Substances 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- 229920002125 Sokalan® Polymers 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- VPNOHCYAOXWMAR-UHFFFAOYSA-N docosan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCCCCCN VPNOHCYAOXWMAR-UHFFFAOYSA-N 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 229920001778 nylon Polymers 0.000 description 2
- 229920000058 polyacrylate Polymers 0.000 description 2
- 239000004584 polyacrylic acid Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 210000002268 wool Anatomy 0.000 description 2
- AWMLROSUUNZXQP-UHFFFAOYSA-N 2-amino-4-phenyldiazenylphenol Chemical compound C1=C(O)C(N)=CC(N=NC=2C=CC=CC=2)=C1 AWMLROSUUNZXQP-UHFFFAOYSA-N 0.000 description 1
- NUIURNJTPRWVAP-UHFFFAOYSA-N 3,3'-Dimethylbenzidine Chemical group C1=C(N)C(C)=CC(C=2C=C(C)C(N)=CC=2)=C1 NUIURNJTPRWVAP-UHFFFAOYSA-N 0.000 description 1
- YDOOYJZNFQGRCN-UHFFFAOYSA-N 3-[2-cyanoethyl(dodecyl)amino]propanenitrile Chemical compound CCCCCCCCCCCCN(CCC#N)CCC#N YDOOYJZNFQGRCN-UHFFFAOYSA-N 0.000 description 1
- ULUIMLJNTCECJU-UHFFFAOYSA-N 3-amino-4-hydroxybenzenesulfonate;hydron Chemical compound NC1=CC(S(O)(=O)=O)=CC=C1O ULUIMLJNTCECJU-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- TZSOUYVTFYFUPB-UHFFFAOYSA-N CCCCCCCCCCCCCCCCCCCCCCN(CCC#N)CCC#N Chemical compound CCCCCCCCCCCCCCCCCCCCCCN(CCC#N)CCC#N TZSOUYVTFYFUPB-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 229920001479 Hydroxyethyl methyl cellulose Polymers 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- 229920002302 Nylon 6,6 Polymers 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 241000711981 Sais Species 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- AEDZKIACDBYJLQ-UHFFFAOYSA-N ethane-1,2-diol;hydrate Chemical group O.OCCO AEDZKIACDBYJLQ-UHFFFAOYSA-N 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- DZQXQAXLDXJEAG-UHFFFAOYSA-N n-(2-hydroxyphenyl)nitramide Chemical compound OC1=CC=CC=C1N[N+]([O-])=O DZQXQAXLDXJEAG-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000011179 visual inspection Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- 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
- D06P1/60—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 polyethers
- D06P1/607—Nitrogen-containing polyethers or their quaternary derivatives
- D06P1/6076—Nitrogen-containing polyethers or their quaternary derivatives addition products of amines and alkylene oxides or oxiranes
-
- 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
- D06P1/653—Nitrogen-free carboxylic acids or their salts
-
- 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
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/02—Material containing basic nitrogen
- D06P3/04—Material containing basic nitrogen containing amide groups
- D06P3/24—Polyamides; Polyurethanes
- D06P3/241—Polyamides; Polyurethanes using acid dyes
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Coloring (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3341870 | 1970-07-09 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2134024A1 DE2134024A1 (de) | 1972-01-13 |
| DE2134024B2 true DE2134024B2 (de) | 1973-04-05 |
Family
ID=10352700
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712134024 Pending DE2134024B2 (de) | 1970-07-09 | 1971-07-08 | Oberflaechenaktive verbindungen |
Country Status (13)
| Country | Link |
|---|---|
| AT (1) | AT304458B (enExample) |
| BE (1) | BE769718A (enExample) |
| CH (1) | CH546733A (enExample) |
| CS (1) | CS151594B2 (enExample) |
| DE (1) | DE2134024B2 (enExample) |
| ES (1) | ES393025A1 (enExample) |
| FR (1) | FR2100439A5 (enExample) |
| GB (1) | GB1317976A (enExample) |
| IL (1) | IL37212A (enExample) |
| NL (1) | NL7109464A (enExample) |
| PL (1) | PL83196B1 (enExample) |
| SU (1) | SU453826A3 (enExample) |
| ZA (1) | ZA714469B (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2841800A1 (de) | 1977-09-29 | 1979-04-12 | Ciba Geigy Ag | Verfahren zum faerben von wollhaltigen fasermaterialien |
| FR2552791B1 (fr) * | 1983-09-29 | 1986-12-05 | Sandoz Sa | Procede de teinture de substrats textiles comprenant de la laine |
| BRPI0507904A (pt) * | 2004-02-19 | 2007-07-10 | Ciba Sc Holding Ag | método de aumentar intensidade da tonalidade da cor |
| CN113372241B (zh) * | 2020-03-09 | 2023-01-13 | 万华化学集团股份有限公司 | 脂肪族伯胺一步法合成双腈乙基叔胺的方法 |
-
1970
- 1970-07-09 GB GB3341870A patent/GB1317976A/en not_active Expired
-
1971
- 1971-06-29 CH CH952371A patent/CH546733A/xx not_active IP Right Cessation
- 1971-07-02 IL IL37212A patent/IL37212A/xx unknown
- 1971-07-06 ZA ZA714469A patent/ZA714469B/xx unknown
- 1971-07-08 CS CS5047A patent/CS151594B2/cs unknown
- 1971-07-08 AT AT597371A patent/AT304458B/de not_active IP Right Cessation
- 1971-07-08 FR FR7125102A patent/FR2100439A5/fr not_active Expired
- 1971-07-08 BE BE769718A patent/BE769718A/xx unknown
- 1971-07-08 DE DE19712134024 patent/DE2134024B2/de active Pending
- 1971-07-08 ES ES393025A patent/ES393025A1/es not_active Expired
- 1971-07-08 NL NL7109464A patent/NL7109464A/xx unknown
- 1971-07-08 PL PL1971149301A patent/PL83196B1/pl unknown
- 1971-07-08 SU SU1685173A patent/SU453826A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| PL83196B1 (enExample) | 1975-12-31 |
| CH546733A (de) | 1974-03-15 |
| CS151594B2 (enExample) | 1973-10-19 |
| NL7109464A (enExample) | 1972-01-11 |
| FR2100439A5 (enExample) | 1972-03-17 |
| SU453826A3 (ru) | 1974-12-15 |
| ES393025A1 (es) | 1974-05-16 |
| DE2134024A1 (de) | 1972-01-13 |
| AT304458B (de) | 1973-01-10 |
| ZA714469B (en) | 1972-03-29 |
| BE769718A (fr) | 1972-01-10 |
| GB1317976A (en) | 1973-05-23 |
| IL37212A (en) | 1975-06-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2633615C3 (de) | Verfahren zum Färben von synthetischen Polyamid-Fasermaterialien | |
| DE1543271A1 (de) | Verfahren zur Herstellung von N-Hydroxyalkylaethylencarbonsaeuremiden | |
| DE2555769A1 (de) | Verfahren zur herstellung von n-alkylglycinnitrilen | |
| DE1794332B2 (de) | Anthrachinonfarbstoffe. Ausscheidung aus: 1492066 | |
| DE2134024B2 (de) | Oberflaechenaktive verbindungen | |
| DE1924765B2 (de) | Polyoxyalkylierte Amine und deren Verwendung beim Färben mit Reaktivfarbstoffen | |
| US3822113A (en) | Acid dye and ethylene oxide condensate of an n-long chain alkyl dipropylene triamine | |
| DE2220710A1 (de) | Nassechtheitsverbesserungsmittel | |
| DE2537481A1 (de) | Tertiaere amide und verfahren zu ihrer herstellung | |
| DE3233830A1 (de) | Perfluoralkyl-malein- und -fumarsaeureamide, verfahren zu deren herstellung und ihre verwendung als schmutzabweisendes mittel | |
| DE633081C (de) | Verfahren zur Verbesserung der Wasserechtheit von Faerbungen auf Textilstoffen | |
| DE69014886T2 (de) | Anionische polykarboxylierte oberflächenaktive mittel als färbeegalisiermittel. | |
| DE899042C (de) | Verfahren zur Herstellung von neuen 4, 4'-Diaminostilbendisulfon- oder -dicarbonsaeuren | |
| DE2519002C3 (de) | Verfahren zur Herstellung von l-(2-Cyanathylamino)-3-acylaminobenzolen | |
| DE902090C (de) | Verfahren zur Herstellung von Kondensationsprodukten | |
| DE60223004T2 (de) | Schutz für reduktionsempfindliche farbstoffe | |
| EP0621266A1 (de) | Sterisch gehinderte Phenole und ihre Verwendung zur Stabilisierung von Polyamid-Fasermaterialen | |
| AT164024B (de) | Verfahren zur Herstellung von wasserlöslichen höhermolekularen Guanaminderivaten | |
| DE630771C (de) | Verfahren zur Herstellung von hoehermolekularen alkylierten Benzimidazolen und deren Abkoemmlingen | |
| AT226190B (de) | Verfahren zum Färben von stickstoffhaltigen Fasern mit sulfonsäuregruppenhaltigen Kupferphthalocyaninen und Mittel zur Durchführung des Verfahrens | |
| DE880589C (de) | Verfahren zur Herstellung von hypnotisch wirkenden Hydantoin-Verbindungen | |
| DE2725780A1 (de) | Stickstoffhaltige kondensationsprodukte | |
| DE1593746A1 (de) | Verfahren zur Herstellung neuer quaternaerer Ammoniumverbindungen | |
| EP0522339A2 (de) | Formazan-Farbstoffe mit einem Diffluorpyrimidinreaktivrest | |
| AT204185B (de) | Haarwaschmittel |