EP0093361A2 - Composés alcoxyalcoylés d'ammonium quaternaire, procédé de préparation et utilisation - Google Patents

Composés alcoxyalcoylés d'ammonium quaternaire, procédé de préparation et utilisation Download PDF

Info

Publication number: EP0093361A2
Authority: EP; European Patent Office
Prior art keywords: oder; und; benzyl; methyl; ethyl
Prior art date: 1982-04-29
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.): Granted

Application number

EP83104004A

Other languages

German (de)

English (en)

Other versions

EP0093361A3 (en

EP0093361B1 (fr

Inventor

Francesco Dr. Cargnino

Marco Levis

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.)

Hoechst Italia SpA

Original Assignee

Hoechst Italia SpA

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.)

1982-04-29

Filing date

1983-04-23

Publication date

1983-11-09

1983-04-23 Application filed by Hoechst Italia SpA filed Critical Hoechst Italia SpA

1983-04-23 Priority to AT83104004T priority Critical patent/ATE25967T1/de

1983-11-09 Publication of EP0093361A2 publication Critical patent/EP0093361A2/fr

1984-09-26 Publication of EP0093361A3 publication Critical patent/EP0093361A3/de

1987-03-18 Application granted granted Critical

1987-03-18 Publication of EP0093361B1 publication Critical patent/EP0093361B1/fr

Status Expired legal-status Critical Current

Links

239000000835 fiber Substances 0.000 claims abstract description 43
239000003795 chemical substances by application Substances 0.000 claims abstract description 24
238000004043 dyeing Methods 0.000 claims abstract description 20
150000001875 compounds Chemical class 0.000 claims abstract description 17
229920002239 polyacrylonitrile Polymers 0.000 claims abstract description 16
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 15
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 13
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 12
125000000217 alkyl group Chemical group 0.000 claims abstract description 11
229920000728 polyester Polymers 0.000 claims abstract description 9
125000003342 alkenyl group Chemical group 0.000 claims abstract description 5
QLAJNZSPVITUCQ-UHFFFAOYSA-N 1,3,2-dioxathietane 2,2-dioxide Chemical group O=S1(=O)OCO1 QLAJNZSPVITUCQ-UHFFFAOYSA-N 0.000 claims abstract description 4
ZPFAVCIQZKRBGF-UHFFFAOYSA-N 1,3,2-dioxathiolane 2,2-dioxide Chemical group O=S1(=O)OCCO1 ZPFAVCIQZKRBGF-UHFFFAOYSA-N 0.000 claims abstract description 4
229910052736 halogen Inorganic materials 0.000 claims abstract description 4
229940100198 alkylating agent Drugs 0.000 claims description 10
239000002168 alkylating agent Substances 0.000 claims description 10
238000000034 method Methods 0.000 claims description 10
150000002367 halogens Chemical class 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 abstract description 3
239000000975 dye Substances 0.000 description 47
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
239000000047 product Substances 0.000 description 13
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 11
238000004040 coloring Methods 0.000 description 7
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
239000003513 alkali Substances 0.000 description 6
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 6
229940073608 benzyl chloride Drugs 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
238000005804 alkylation reaction Methods 0.000 description 5
239000000203 mixture Substances 0.000 description 5
125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
238000009835 boiling Methods 0.000 description 4
238000010411 cooking Methods 0.000 description 4
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
238000005956 quaternization reaction Methods 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
125000001931 aliphatic group Chemical group 0.000 description 3
230000029936 alkylation Effects 0.000 description 3
239000004744 fabric Substances 0.000 description 3
239000003925 fat Substances 0.000 description 3
-1 for example Substances 0.000 description 3
239000000463 material Substances 0.000 description 3
239000000243 solution Substances 0.000 description 3
239000003760 tallow Substances 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
150000001350 alkyl halides Chemical class 0.000 description 2
150000001450 anions Chemical class 0.000 description 2
239000012736 aqueous medium Substances 0.000 description 2
125000001204 arachidyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
239000000981 basic dye Substances 0.000 description 2
150000001555 benzenes Chemical class 0.000 description 2
JBIROUFYLSSYDX-UHFFFAOYSA-M benzododecinium chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 JBIROUFYLSSYDX-UHFFFAOYSA-M 0.000 description 2
235000019445 benzyl alcohol Nutrition 0.000 description 2
125000002091 cationic group Chemical group 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
QWIGSMCPAKBYLY-UHFFFAOYSA-O 2,4-dimethoxy-n-[2-(1,3,3-trimethylindol-1-ium-2-yl)ethenyl]aniline Chemical compound COC1=CC(OC)=CC=C1NC=CC1=[N+](C)C2=CC=CC=C2C1(C)C QWIGSMCPAKBYLY-UHFFFAOYSA-O 0.000 description 1
TZXATTMVGZDPHM-UHFFFAOYSA-N 2-[4-[(2-chloro-4-nitrophenyl)diazenyl]-n-ethylanilino]ethyl-trimethylazanium Chemical compound C1=CC(N(CC[N+](C)(C)C)CC)=CC=C1N=NC1=CC=C([N+]([O-])=O)C=C1Cl TZXATTMVGZDPHM-UHFFFAOYSA-N 0.000 description 1
235000013162 Cocos nucifera Nutrition 0.000 description 1
244000060011 Cocos nucifera Species 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
235000019482 Palm oil Nutrition 0.000 description 1
RFQSMLBZXQOMKK-UHFFFAOYSA-N [3-[(4,8-diamino-6-bromo-1,5-dioxonaphthalen-2-yl)amino]phenyl]-trimethylazanium;chloride Chemical compound [Cl-].C[N+](C)(C)C1=CC=CC(NC=2C(C3=C(N)C=C(Br)C(=O)C3=C(N)C=2)=O)=C1 RFQSMLBZXQOMKK-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
239000002253 acid Substances 0.000 description 1
239000000654 additive Substances 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
239000002518 antifoaming agent Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
230000000903 blocking effect Effects 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
239000003093 cationic surfactant Substances 0.000 description 1
230000003750 conditioning effect Effects 0.000 description 1
150000004292 cyclic ethers Chemical class 0.000 description 1
230000006735 deficit Effects 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
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000003792 electrolyte Substances 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000005187 foaming Methods 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
230000001788 irregular Effects 0.000 description 1
239000012263 liquid product Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
238000002844 melting Methods 0.000 description 1
SYHRPJPCZWZVSR-UHFFFAOYSA-M n-benzyl-4-[(2,4-dimethyl-1,2,4-triazol-4-ium-3-yl)diazenyl]-n-methylaniline;bromide Chemical compound [Br-].C=1C=C(N=NC2=[N+](C=NN2C)C)C=CC=1N(C)CC1=CC=CC=C1 SYHRPJPCZWZVSR-UHFFFAOYSA-M 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
239000002540 palm oil Substances 0.000 description 1
125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000000979 retarding effect Effects 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000003549 soybean oil Substances 0.000 description 1
235000012424 soybean oil Nutrition 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical group COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
238000004804 winding Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Images

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
- D06P1/655—Compounds containing ammonium groups
- D06P1/66—Compounds containing ammonium groups containing quaternary ammonium groups
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/92—Synthetic fiber dyeing
- Y10S8/922—Polyester fiber
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/92—Synthetic fiber dyeing
- Y10S8/927—Polyacrylonitrile fiber

Definitions

the permanent retarders are usually very effective. In competition with the dyes, they bond firmly to the fibers. They are therefore only used in low concentrations and their amount must be calculated precisely by taking into account the saturation factors of the dyes and the fiber (true technical equivalents).
This type of retarders has the disadvantage that, in the event of an overdose, it does not allow the dye liquor to be completely depleted in the bath, or that it makes it difficult for the dyeing of goods already dyed from polyacrylonitrile fibers or anionically modified polyester fibers in those cases in which a further, subsequent dyeing is necessary is.
the aforementioned permanent retarders generally consist of quaternary ammonium salts, the best known of which is lauryldimethylbenzylammonium chloride.
the temporary retarders consist of various products that have a less pronounced ionic charge than the aforementioned. Therefore, the temporary retarders connect to the fiber in a more labile manner. Their connection to the active groups of the fiber is such that they can be displaced by the dye, since this has more pronounced ionic properties. In other words, in contrast to the permanent retarders, the temporary retarders block the active centers of the fiber to a lesser extent. As is known, the temporary retarders are used in relatively high concentrations and cannot guarantee complete uniformity of the coloring under all application conditions.
radicals R which are derived from naturally occurring fats, such as, for example, tallow fatty alkyl, coconut fatty alkyl, soybean oil alkyl, palm oil alkyl or the like. Since these naturally occurring fats are mixtures of compounds with different chain lengths, the radical R in these cases is accordingly a mixture of alkyl or alkenyl groups with different chain lengths.
the terms "product of formula (1)”, “retarders and / or leveling agents of formula (1)”, “product of the present invention”, and “retarders and / or leveling agents of the present invention” include both a single compound falling under the formula (1), and also a mixture of two or more compounds of the formula (1), as can also be seen from the examples.
the retarders and / or leveling agents of the present invention are capable of blocking the fiber enough to guarantee normal dye uptake. At the same time, they are able to slowly detach from the fiber if there is an excess of dye in the dye liquor or if the retarder and / or leveling agent is overdosed by accident.
the new retarder and / or leveling agent is used in the dyeing of polyacrylonitrile fibers and anionically modified polyester fibers by the methods which are generally known for permanent retarders.
the optimal amount of retarders and / or leveling agents to be added to the dye liquor is to be calculated by taking into account the saturation factors of the fiber to be dyed and the dyes used, as is generally known to the person skilled in the art in this field. If, in addition to the retarders and / or leveling agents of the formula 1, retarders of known type are also added to the process according to the present invention, these retarders should always be present in a smaller amount compared to the compounds according to the invention.
the material to be dyed which consists of polyacrylonitrile or anionically modified polyester fibers, can be in different stages of processing, e.g. as yarn, tops (special cuts of the yarn), Tows (special cuts of the fabric), fabric or knitted fabric.
the aqueous dye liquor contains the necessary amount of dye, electrolytes, any additives (wetting agents, anti-foaming agents and the like) and a lot of retarders and / or leveling agents of the formula 1. The respective amounts depend on the saturation factor of the fiber, the dye or the dyes, the substantivity of the dye or dyes and the characteristics of the dyeing equipment used.
the liquor ratio is usually between 1: 1 and 1: 200, preferably between 1: 2 and 1:40.
the retarders and / or Leveling agents of the invention can be added directly to the dye liquor.
the dyeing liquor is heated to a temperature of between 80 and 110 ° C and so long that complete exhaustion of the dye is guaranteed. This period is usually between 20 and 120 minutes.
the amount of retarders and / or leveling agents is generally between 0.1 and 4% by weight, based on the material to be colored.
the pH of the dye liquor is adjusted to values between 1 and 7, preferably between 3 and 6.
the retarders and / or leveling agents of the present invention can be prepared as described in "Cationic Surfactants", edited by Eric Jungermann, Marcel Dekker Inc., New York (1970), p. 29.
compounds of the formula (3) implemented with alkylating agents.
the reaction takes place in an aqueous medium or in an organic solvent in the presence of alkali.
suitable organic solvents are lower aliphatic alcohols, ethers, especially cyclic ethers such as tetrahydrofuran or dioxane and benzene derivatives such as benzene, toluene, xylene and chlorinated benzenes.
Alkali can be mentioned above all as alkali hydroxides and alkali carbonates. It is preferred to work in an aqueous medium in the presence of sodium hydroxide.
Preferred alkylating agents are methyl or ethyl halides, preferably chloride, dimethyl or diethyl sulfate or trimethyl or triethyl phosphate.
the alkylation reaction is generally carried out at temperatures between 55 and 100 ° C, preferably between 80 and 95 ° C. If complete quaternization is desired, it is advisable to use an excess of alkylating agents. After the alkylation, the excess of alkylating agents can be removed by evaporation from the reaction mixture, for example if alkyl halides are used.
alkyl is a linear aliphatic chain derived from hydrogenated tallow, which is a mixture of octadecyl, hexadecyl, tetradecyl radicals
alkyl is a linear aliphatic chain derived from hydrogenated tallow, which is a mixture of octadecyl, hexadecyl, tetradecyl radicals
the reaction is exothermic and the addition of benzyl chloride must therefore be adjusted so that the temperature does not exceed 95-98 ° C to avoid foaming caused by boiling the water at 100 ° C. It is best to work in a reaction vessel with a reflux condenser. It is also possible to work in a closed apparatus under light pressure.
the pH must be kept between 2 and 7, preferably between 4 and 7.
the reaction is stopped by heating to 80-100 ° C, better between 90-98 ° C, until the benzyl chloride has completely disappeared. This gives 680-690 parts of the desired product at a concentration of 100% by weight, the product has a melting point of 80-95 ° C.
Example 1 As described in Example 1, 1200 parts of water and 65 parts of 30% sodium hydroxide are added to 374 parts (1 mol) of N'-dodecyl-N'-N "-trihydroxyethylpropylenediamine at 80 ° C. to form a homogeneous paste. 252 parts Benzyl chloride (2 moles) are added between 60-95 ° C, preferably between 80-90 ° C and at a temperature of 95-98 ° C (exothermic) the pH of the reaction mixture is between 1 and 7, preferably between 4 and 7. To complete the reaction, 250 parts of water are distilled off, thereby removing about 10 parts of benzyl alcohol which has formed in the course of the reaction.
Example 2 As described in Example 2, 456 parts (1 mole) of N'-octadecenyl-N'-N "-trihydroxyethyl-propylenediamine at 60-90 ° C, preferably at 70-80 ° C, 1200 parts of water and 60 parts of 30% Sodium hydroxide is added to form a homogeneous paste, 189 parts (1.5 moles) of benzyl chloride are then added between 50-95 ° C., preferably between 80-90 ° C.
Example 4 The procedure described in Example 4 is repeated, by extending the cooking time to 90 minutes and increasing the concentration of the retarder to 0.35 g / 1.
the dyeing carried out with a cooking time of 45 minutes leads to a gradual and complete exhaustion of the dye liquor and to a completely uniform blue dyeing of the fiber.
the fibers are dyed the same as the fibers dyed with the retarder and / or leveling agent of the present invention, but show a higher antistatic value than those dyed with the conventional retarders.
the numbers in the table represent the dye content in the dye liquor at the various times, expressed as a percentage, based on the initial amount (100%).
the table shows that the quaternization of all two nitrogen atoms in the molecule of the retarder and / or leveling agent of the formula (1) has a greater retarding effect.
a dye liquor which is composed as follows:
the process is carried out by heating the dye liquor to 98 ° C., the temperature being reduced by 1 ° C./minute lets rise and holds the dye liquor for one hour at cooking temperature. (Curve 1 in FIG. 1)
Another 10 g of the same fiber are treated in parallel in a dyeing liquor which is prepared like the first, but contains 0.4 g of a tallow fat propylene diamine quaternized with dimethyl sulfate as a retarder.
Example 10 The procedure is as given in Example 10 using a reaction product of 2.5 mol of ethylene oxide and 1 mol of stearylamine as a retarder. This product is a commercially available temporary retarder.
the retarder and / or leveling agent of the present invention proves that it has remarkable temporary characteristics.

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Engineering & Computer Science (AREA)
Textile Engineering (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Coloring (AREA)

EP83104004A 1982-04-29 1983-04-23 Composés alcoxyalcoylés d'ammonium quaternaire, procédé de préparation et utilisation Expired EP0093361B1 (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
AT83104004T ATE25967T1 (de)	1982-04-29	1983-04-23	Quartaere alkoxyalkylammoniumverbindungen, verfahren zu deren herstellung und deren verwendung.

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
IT21002/82A IT1151548B (it)	1982-04-29	1982-04-29	Procedimento di tintura uniforme di fibre poliacrilonitriliche e fibre poliestere modificate anioniche e prodotti ritardanti e/o egualizzanti per esso
IT2100282		1982-04-29

Publications (3)

Publication Number	Publication Date
EP0093361A2 true EP0093361A2 (fr)	1983-11-09
EP0093361A3 EP0093361A3 (en)	1984-09-26
EP0093361B1 EP0093361B1 (fr)	1987-03-18

Family

ID=11175243

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
EP83104004A Expired EP0093361B1 (fr)	1982-04-29	1983-04-23	Composés alcoxyalcoylés d'ammonium quaternaire, procédé de préparation et utilisation

Country Status (7)

Country	Link
US (1)	US4579560A (fr)
EP (1)	EP0093361B1 (fr)
JP (1)	JPS591451A (fr)
AT (1)	ATE25967T1 (fr)
BR (1)	BR8302201A (fr)
DE (1)	DE3370321D1 (fr)
IT (1)	IT1151548B (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH0524276Y2 (fr) *	1986-04-04	1993-06-21
US6458999B1 (en) *	1999-12-13	2002-10-01	Nova Molecular Technologies Inc	Ether diamines and derivatives
WO2007053235A1 (fr) *	2005-11-04	2007-05-10	Sachem, Inc.	Processus chromatographie par deplacement a echange de cations et composes cationiques organiques servant de composes deplaceurs dans un tel processus
USD657110S1 (en)	2011-08-10	2012-04-03	Schlomann Brian K	Brake maintenance cart

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2759975A (en) *	1952-05-28	1956-08-21	Gen Aniline & Film Corp	Mixed alkyl-benzyl-alkylol quaternary ammonium salts
GB852548A (en) *	1957-02-05	1960-10-26	Sandoz Ltd	Polyethoxy quaternary ammonium compounds as levelling and stripping agents for dyestuffs
US3466247A (en) *	1967-03-20	1969-09-09	Kao Corp	Method of preparing cationic bitumen emulsions
CH1633473A4 (fr) *	1973-11-20	1975-04-15
LU75088A1 (fr) *	1976-06-04	1978-01-18
DE2633138A1 (de) *	1976-07-23	1978-01-26	Cassella Farbwerke Mainkur Ag	Verfahren zur erzeugung egaler faerbungen auf gebilden aus polyacrylnitril oder sauer modifizierten polyestern

1982
- 1982-04-29 IT IT21002/82A patent/IT1151548B/it active
1983
- 1983-04-23 AT AT83104004T patent/ATE25967T1/de not_active IP Right Cessation
- 1983-04-23 EP EP83104004A patent/EP0093361B1/fr not_active Expired
- 1983-04-23 DE DE8383104004T patent/DE3370321D1/de not_active Expired
- 1983-04-28 JP JP58074181A patent/JPS591451A/ja active Pending
- 1983-04-28 BR BR8302201A patent/BR8302201A/pt unknown
1984
- 1984-07-06 US US06/628,250 patent/US4579560A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
BR8302201A (pt)	1983-12-27
DE3370321D1 (en)	1987-04-23
EP0093361A3 (en)	1984-09-26
EP0093361B1 (fr)	1987-03-18
IT8221002A0 (it)	1982-04-29
JPS591451A (ja)	1984-01-06
US4579560A (en)	1986-04-01
IT1151548B (it)	1986-12-24
ATE25967T1 (de)	1987-04-15

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DE2843659A1 (de)	1980-04-10	Verwendung quaternierter etheramine als faserpraeparationsmittel
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DE692895C (de)	1940-06-28	ffen
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