CS229063B1 - Compound for cationizing polymeric materials and method of preparing same - Google Patents

Compound for cationizing polymeric materials and method of preparing same Download PDF

Info

Publication number: CS229063B1
Authority: CS; Czechoslovakia
Prior art keywords: temperature; compounds; formula; bis; epichlorohydrin
Prior art date: 1981-03-04

Application number

CS153781A

Other languages

Czech (cs)

English (en)

Inventor

Drahomir Dvorsky

Karel Cerovsky

Original Assignee

Drahomir Dvorsky

Karel Cerovsky

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.)

1981-03-04

Filing date

1981-03-04

Publication date

1984-05-14

1981-03-04 Application filed by Drahomir Dvorsky, Karel Cerovsky filed Critical Drahomir Dvorsky

1981-03-04 Priority to CS153781A priority Critical patent/CS229063B1/cs

1982-01-29 Priority to FR8201484A priority patent/FR2509302A1/fr

1982-02-15 Priority to NL8200574A priority patent/NL8200574A/nl

1982-02-17 Priority to GB8204743A priority patent/GB2094298B/en

1982-02-18 Priority to BG5545882A priority patent/BG41403A1/xx

1982-02-22 Priority to DD23755482A priority patent/DD245571A3/de

1982-02-23 Priority to YU00397/82A priority patent/YU39782A/xx

1982-02-23 Priority to SU827772299A priority patent/SU1315453A1/ru

1982-02-24 Priority to IT19828/82A priority patent/IT1150197B/it

1982-03-02 Priority to PL1982235285A priority patent/PL134615B2/xx

1982-03-03 Priority to PT74518A priority patent/PT74518B/pt

1982-03-03 Priority to BR8201120A priority patent/BR8201120A/pt

1982-03-03 Priority to HU82651A priority patent/HU190790B/hu

1982-03-04 Priority to BE0/207471A priority patent/BE892364A/fr

1982-03-04 Priority to JP3314782A priority patent/JPS57167975A/ja

1982-03-04 Priority to CH133282A priority patent/CH670351GA3/de

1982-03-04 Priority to DE19823207845 priority patent/DE3207845A1/de

1982-03-04 Priority to RO106812A priority patent/RO85280B/ro

1983-07-21 Priority to US06/516,147 priority patent/US4499282A/en

1983-07-21 Priority to US06/516,134 priority patent/US4468228A/en

1984-05-11 Priority to CS350484A priority patent/CS241919B3/cs

1984-05-14 Publication of CS229063B1 publication Critical patent/CS229063B1/cs

1984-11-06 Priority to US06/668,669 priority patent/US4547574A/en

1984-11-06 Priority to US06/668,645 priority patent/US4542217A/en

Links

150000001875 compounds Chemical class 0.000 title claims description 18
238000000034 method Methods 0.000 title claims description 4
239000000463 material Substances 0.000 title claims 2
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 12
KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 8
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 6
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 5
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 5
PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 4
238000002360 preparation method Methods 0.000 claims description 4
DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 claims description 4
239000007864 aqueous solution Substances 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
150000007522 mineralic acids Chemical class 0.000 claims description 3
150000007524 organic acids Chemical class 0.000 claims description 3
USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 claims description 3
PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 3
150000001450 anions Chemical group 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
238000004172 nitrogen cycle Methods 0.000 claims description 2
150000003839 salts Chemical class 0.000 claims description 2
125000002768 hydroxyalkyl group Chemical group 0.000 claims 3
239000003513 alkali Substances 0.000 claims 1
229910052757 nitrogen Inorganic materials 0.000 claims 1
235000005985 organic acids Nutrition 0.000 claims 1
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 15
-1 1,3-bis (3-chloro-2-hydroxypropyl) pyrimidinediyl chloride Chemical compound 0.000 description 13
238000001816 cooling Methods 0.000 description 12
239000011541 reaction mixture Substances 0.000 description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
239000000460 chlorine Substances 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 7
239000000203 mixture Substances 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
229910021653 sulphate ion Inorganic materials 0.000 description 5
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
239000011521 glass Substances 0.000 description 4
239000000243 solution Substances 0.000 description 4
238000005516 engineering process Methods 0.000 description 3
RXYPXQSKLGGKOL-UHFFFAOYSA-N 1,4-dimethylpiperazine Chemical compound CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
239000013543 active substance Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 description 1
BTTNYQZNBZNDOR-UHFFFAOYSA-N 2,4-dichloropyrimidine Chemical compound ClC1=CC=NC(Cl)=N1 BTTNYQZNBZNDOR-UHFFFAOYSA-N 0.000 description 1
APHUIPGIURQXRC-UHFFFAOYSA-N C(C)(=O)[O-].ClCC(C[NH+]1C=NCC1)O Chemical compound C(C)(=O)[O-].ClCC(C[NH+]1C=NCC1)O APHUIPGIURQXRC-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
RPMIGOQKXYPPPX-UHFFFAOYSA-N ClCC(O)CC1=CC=CN1 Chemical compound ClCC(O)CC1=CC=CN1 RPMIGOQKXYPPPX-UHFFFAOYSA-N 0.000 description 1
RQAYNWCTEURSQH-UHFFFAOYSA-N S(=O)(=O)([O-])[O-].C(C1CO1)[NH+]1CN(CC1)CC1CO1.C(C1CO1)[NH+]1CN(CC1)CC1CO1 Chemical compound S(=O)(=O)([O-])[O-].C(C1CO1)[NH+]1CN(CC1)CC1CO1.C(C1CO1)[NH+]1CN(CC1)CC1CO1 RQAYNWCTEURSQH-UHFFFAOYSA-N 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
MNNIVROUZOHKTH-UHFFFAOYSA-M [Cl-].ClCC(C[N+]1(N(CCC1)CC(CCl)O)C)O Chemical compound [Cl-].ClCC(C[N+]1(N(CCC1)CC(CCl)O)C)O MNNIVROUZOHKTH-UHFFFAOYSA-M 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
125000000129 anionic group Chemical group 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
239000000975 dye Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
230000007613 environmental effect Effects 0.000 description 1
239000012530 fluid Substances 0.000 description 1
150000002391 heterocyclic compounds Chemical class 0.000 description 1
150000004678 hydrides Chemical group 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
230000004941 influx Effects 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000007670 refining Methods 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000000126 substance Substances 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
239000004753 textile Substances 0.000 description 1
238000004448 titration Methods 0.000 description 1
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical class CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/385—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen containing epoxy groups
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Textile Engineering (AREA)
Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Plural Heterocyclic Compounds (AREA)
Coloring (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Crystals, And After-Treatments Of Crystals (AREA)

CS153781A 1981-03-03 1981-03-04 Compound for cationizing polymeric materials and method of preparing same CS229063B1 (en)

Priority Applications (23)

Application Number	Priority Date	Filing Date	Title
CS153781A CS229063B1 (en)	1981-03-04	1981-03-04	Compound for cationizing polymeric materials and method of preparing same
FR8201484A FR2509302A1 (fr)	1981-03-04	1982-01-29	Composes d'ammonium quaternaire, procede pour leur fabrication et utilisation de ces produits dans les apprets de finissage des tissus
NL8200574A NL8200574A (nl)	1981-03-04	1982-02-15	Kwaternaire ammoniumverbindingen, werkwijze voor het bereiden daarvan, alsmede de toepassing daarvan voor het appreteren van textielweefsel.
GB8204743A GB2094298B (en)	1981-03-04	1982-02-17	Quaternary ammonium compounds and use thereof for finishing textile fabrics
BG5545882A BG41403A1 (en)	1981-03-04	1982-02-18	Compound for cationizing polymer materials and method for its preparing
DD23755482A DD245571A3 (de)	1981-03-04	1982-02-22	Verfahren zur herstellung von loesungen quarternaerer ammoniumsalze zur behandlung von zellulosestoffen
YU00397/82A YU39782A (en)	1981-03-04	1982-02-23	Process for prodcing quaternary ammonium compounds
SU827772299A SU1315453A1 (ru)	1981-03-04	1982-02-23	Способ получени растворов четвертичных аммониевых солей
IT19828/82A IT1150197B (it)	1981-03-04	1982-02-24	Composti di ammonio quaternario,metodo di loro preparazione loro uso per il finissaggio di tessuti
PL1982235285A PL134615B2 (en)	1981-03-04	1982-03-02	Method of manufacture of quaternary ammonium compounds
BR8201120A BR8201120A (pt)	1981-03-04	1982-03-03	Processo para preparacao de compostos de amonio quaternario e sua aplicacao para o enobrecimento de materiais texteis
PT74518A PT74518B (de)	1981-03-04	1982-03-03	Verfahren zur vorbereitung von quarternaeren ammoniumverbindun-gen und deren verwendung zum veredeln von textilmaterialien
HU82651A HU190790B (en)	1981-03-04	1982-03-03	Process for preparing quaternary ammonium compounds and for dyeing textiles and making them crease-resistant by using the compounds
RO106812A RO85280B (ro)	1981-03-04	1982-03-04	Procedeu pentru prepararea unor compusi de amoniu cuaternari
JP3314782A JPS57167975A (en)	1981-03-04	1982-03-04	Quaternary ammonium compound, manufacture and use for fiber material finishing
CH133282A CH670351GA3 (fr)	1981-03-04	1982-03-04
DE19823207845 DE3207845A1 (de)	1981-03-04	1982-03-04	Quaternaere ammoniumverbindungen, ihre herstellung und ihre verwendung zum veredeln von textilmaterialien
BE0/207471A BE892364A (fr)	1981-03-04	1982-03-04	Composes d'ammonium quaternaire, procede pour leur preparation et leur utilisation pour l'ennoblissement des matieres textiles
US06/516,147 US4499282A (en)	1981-03-04	1983-07-21	Quaternary ammonium compounds
US06/516,134 US4468228A (en)	1981-03-03	1983-07-21	Quaternary ammonium compounds and method for preparation thereof
CS350484A CS241919B3 (en)	1981-03-04	1984-05-11	Method of textile fibrous materials finishing from triacetate fibres and from their mixtures
US06/668,669 US4547574A (en)	1981-03-04	1984-11-06	Quaternary pyrazinium compounds
US06/668,645 US4542217A (en)	1981-03-04	1984-11-06	Quaternary pyrimidinium compounds

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CS153781A CS229063B1 (en)	1981-03-04	1981-03-04	Compound for cationizing polymeric materials and method of preparing same

Publications (1)

Publication Number	Publication Date
CS229063B1 true CS229063B1 (en)	1984-05-14

Family

ID=5349978

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS153781A CS229063B1 (en)	1981-03-03	1981-03-04	Compound for cationizing polymeric materials and method of preparing same

Country Status (6)

Country	Link
JP (1)	JPS57167975A (fr)
BE (1)	BE892364A (fr)
BG (1)	BG41403A1 (fr)
CS (1)	CS229063B1 (fr)
DD (1)	DD245571A3 (fr)
SU (1)	SU1315453A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3225877A1 (de) *	1982-07-10	1984-01-12	Basf Ag, 6700 Ludwigshafen	Verfahren zum faerben von textilen materialien aus polyacrylnitril

1981
- 1981-03-04 CS CS153781A patent/CS229063B1/cs unknown
1982
- 1982-02-18 BG BG5545882A patent/BG41403A1/xx unknown
- 1982-02-22 DD DD23755482A patent/DD245571A3/de not_active IP Right Cessation
- 1982-02-23 SU SU827772299A patent/SU1315453A1/ru active
- 1982-03-04 BE BE0/207471A patent/BE892364A/fr not_active IP Right Cessation
- 1982-03-04 JP JP3314782A patent/JPS57167975A/ja active Pending

Also Published As

Publication number	Publication date
BE892364A (fr)	1982-07-01
BG41403A1 (en)	1987-06-15
DD245571A3 (de)	1987-05-13
SU1315453A1 (ru)	1987-06-07
JPS57167975A (en)	1982-10-16

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US5659011A (en)	1997-08-19	Agents having high nitrogen content and high cationic charge based on dicyanimide dicyandiamide or guanidine and inorganic ammonium salts
US2423262A (en)	1947-07-01	Compounds having the formula
US3658827A (en)	1972-04-25	Soluble benzimidazole derivatives usable as fungicides
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CS229063B1 (en)	1984-05-14	Compound for cationizing polymeric materials and method of preparing same
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