FR2707288A1 - tert-Butylaminoethyl methacrylate chloride, its process of preparation and its applications - Google Patents
tert-Butylaminoethyl methacrylate chloride, its process of preparation and its applications Download PDFInfo
- Publication number
- FR2707288A1 FR2707288A1 FR9308184A FR9308184A FR2707288A1 FR 2707288 A1 FR2707288 A1 FR 2707288A1 FR 9308184 A FR9308184 A FR 9308184A FR 9308184 A FR9308184 A FR 9308184A FR 2707288 A1 FR2707288 A1 FR 2707288A1
- Authority
- FR
- France
- Prior art keywords
- butylaminoethyl methacrylate
- tert
- chloride
- formula
- preparation
- 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.)
- Granted
Links
- JFXIVKSCAJLVOW-UHFFFAOYSA-N 2-(tert-butylamino)ethyl 2-methylprop-2-enoate;hydrochloride Chemical compound Cl.CC(=C)C(=O)OCCNC(C)(C)C JFXIVKSCAJLVOW-UHFFFAOYSA-N 0.000 title claims abstract description 5
- 238000000034 method Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 4
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims abstract description 10
- BEWCNXNIQCLWHP-UHFFFAOYSA-N 2-(tert-butylamino)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCNC(C)(C)C BEWCNXNIQCLWHP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229940050176 methyl chloride Drugs 0.000 claims abstract description 4
- 238000006243 chemical reaction Methods 0.000 claims description 8
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 3
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- 239000002270 dispersing agent Substances 0.000 claims description 2
- 239000008394 flocculating agent Substances 0.000 claims description 2
- 239000002351 wastewater Substances 0.000 claims description 2
- 125000002091 cationic group Chemical group 0.000 abstract 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- -1 acetonitrile Chemical class 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- KGQLBLGDIQNGSB-UHFFFAOYSA-N benzene-1,4-diol;methoxymethane Chemical compound COC.OC1=CC=C(O)C=C1 KGQLBLGDIQNGSB-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007787 solid Substances 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
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/16—Amines or polyamines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C219/00—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C219/02—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C219/04—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C219/08—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having at least one of the hydroxy groups esterified by a carboxylic acid having the esterifying carboxyl group bound to an acyclic carbon atom of an acyclic unsaturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/52—Treatment of water, waste water, or sewage by flocculation or precipitation of suspended impurities
- C02F1/54—Treatment of water, waste water, or sewage by flocculation or precipitation of suspended impurities using organic material
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
- D21H17/03—Non-macromolecular organic compounds
- D21H17/05—Non-macromolecular organic compounds containing elements other than carbon and hydrogen only
- D21H17/07—Nitrogen-containing compounds
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
- D21H17/03—Non-macromolecular organic compounds
- D21H17/05—Non-macromolecular organic compounds containing elements other than carbon and hydrogen only
- D21H17/14—Carboxylic acids; Derivatives thereof
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H21/00—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties
- D21H21/06—Paper forming aids
- D21H21/08—Dispersing agents for fibres
Abstract
Description
Chlorure de méthacrylate de tertiobutylaminoéthyle, sonTertiary butylaminoethyl methacrylate chloride, bran
procédé de préparation et ses applications. preparation process and its applications.
La présente invention a pour objet le chlorure de méthacrylate de tertiobutylaminoéthyle de formule: The subject of the present invention is tertiary butylaminoethyl methacrylate chloride of formula:
CH2 = C-(I)CH2 = C- (I)
CH3 O-(CH2)2-N{H2-C(CH3)3, Cl que l'on peut préparer par un procédé qui consiste à faire réagir du méthacrylate de tertiobutylaminoéthyle de formule: CH3 O- (CH2) 2-N {H2-C (CH3) 3, Cl which can be prepared by a process which consists in reacting tert-butylaminoethyl methacrylate of formula:
CH2 = C-C (II)CH2 = C-C (II)
CH3 O-(CH2)2-NH-C (CH3)3CH3 O- (CH2) 2-NH-C (CH3) 3
avec du chlorure de méthyle de formule CH3Cl. with methyl chloride of formula CH3Cl.
Cette réaction est inattendue puisqu'il est connu, par exemple par le brevet des Etats-Unis d'Amérique numéro 2.744.884, que les composés du type du méthacrylate de tertiobutylaminoéthyle réagissent sur des composés électrophiles du type RC1 pour donner des produits: CH3 This reaction is unexpected since it is known, for example from United States patent number 2,744,884, that compounds of the tert-butylaminoethyl methacrylate type react on electrophilic compounds of the RC1 type to give products: CH3
CH2=C-COOCH2CH2NC(CH3)3CH2 = C-COOCH2CH2NC (CH3) 3
R R étant CN ou C6H5C0 et, étant donné que de manière analogue, l'oxyde d'éthylène et l'anhydride acétique donnent aussi des dérivés du type: CH3 R R being CN or C6H5C0 and, since in an analogous manner, ethylene oxide and acetic anhydride also give derivatives of the type: CH3
CH2=C-COOCH2CH2NC(CH3)3CH2 = C-COOCH2CH2NC (CH3) 3
E E étant CH2CH2OH ou COCH3, ce procédé de préparation est particulièrement intéressant par rapport à un procédé utilisant HCl comme E E being CH2CH2OH or COCH3, this preparation process is particularly advantageous compared to a process using HCl as
réactif, car il se forme, outre le chlorure visé, comme sous- reactive, because it forms, in addition to the targeted chloride, as a
produit, un méthacrylate de formule: product, a methacrylate of formula:
CH2=C - C - O- CH2 - CH2 -N- C (CH3)3 CH2 = C - C - O- CH2 - CH2 -N- C (CH3) 3
I II!I II!
CH3 O CH3CH3 O CH3
polymérisable et donc valorisable, alors que le procédé utilisant HCl peut donner, outre le produit visé, deux produits de formule: CH3 CH3-C- C -O-CH2-CH2-NH-C(CH3)3 et ilq polymerizable and therefore recoverable, while the process using HCl can give, in addition to the targeted product, two products of formula: CH3 CH3-C- C -O-CH2-CH2-NH-C (CH3) 3 and ilq
C 10C 10
CH3 1 3' CH3-C- C -O-CH2-CH2-N\H2-C(CH3)3, Cl Cl O non polymérisables et qui ne peuvent donc pas être CH3 1 3 'CH3-C- C -O-CH2-CH2-N \ H2-C (CH3) 3, Cl Cl O non-polymerizable and which therefore cannot be
valorisés facilement.easily valued.
On effectue, de préférence, la réaction dans un solvant organique tel qu'un hydrocarbure aromatique comme le toluène, ou une cétone comme l'acétone, la méthyléthylcétone, la méthylisobutylcétone, ou dans un nitrile comme l'acétonitrile, de préférence en présence d'un agent inhibant la polymérisation, tel que l'oxyde méthylique de l'hydroquinone, l'hydroquinone et la phénothiazine, utilisé en présence d'air. La température réactionnelle dépend du solvant utilisé. En général, on effectue la réaction à une température comprise entre 50 C et 120 C et, de préférence, entre 85 C et 100 C avec un rapport molaire du méthacrylate de formule (II) au chlorure de méthyle, compris entre 0,5 et The reaction is preferably carried out in an organic solvent such as an aromatic hydrocarbon such as toluene, or a ketone such as acetone, methyl ethyl ketone, methyl isobutyl ketone, or in a nitrile such as acetonitrile, preferably in the presence of a polymerization-inhibiting agent, such as hydroquinone methyl oxide, hydroquinone and phenothiazine, used in the presence of air. The reaction temperature depends on the solvent used. In general, the reaction is carried out at a temperature between 50 C and 120 C and, preferably, between 85 C and 100 C with a molar ratio of the methacrylate of formula (II) to methyl chloride, between 0.5 and
2 et, de préférence, entre 1 et 1,5. 2 and preferably between 1 and 1.5.
La réaction peut être conduite sous pression The reaction can be carried out under pressure
normale ou sous pression d'air.normal or under air pressure.
L'invention vise également l'utilisation du chlorure de méthacrylate de tertiobutylaminoéthyle comme produit tensio-actif cationique, notamment comme agent floculant pour le traitement des eaux usées et comme The invention also relates to the use of tert-butylaminoethyl methacrylate chloride as cationic surfactant, in particular as a flocculating agent for the treatment of waste water and as
dispersant pour le traitement du papier. dispersant for paper processing.
Les exemples suivants illustrent l'invention. The following examples illustrate the invention.
Exemples 1 à 7Examples 1 to 7
On effectue la réaction dans un réacteur en verre d'une capacité de 1 litre à double enveloppe, en vue de réguler la température. Le réacteur est muni d'une agitation mécanique à vitesse variable, d'une spire de refroidissement et de deux cames plongeantes, l'une pour le gaz réactif, The reaction is carried out in a glass reactor with a capacity of 1 liter with a double jacket, with a view to regulating the temperature. The reactor is fitted with mechanical agitation at variable speed, a cooling coil and two plunging cams, one for the reactive gas,
l'autre pour l'air.the other for air.
On charge le réacteur de 370 g de méthacrylate de tertiobutylaminoéthyle, de 0,48 g, d'oxyde méthylique de l'hydroquinone et de 1000 g du solvant à pression atmosphérique. On introduit à la température indiquée au tableau 1, sous bullage d'air lll,lg de chlorure de méthyle, en la durée indiquée au tableau 1. En fin de réaction, on élimine le chlorure de méthyle n'ayant pas réagi par entraînement à l'air à 60 C pendant 1 heure. On refroidit le milieu à 40 C et on vidange. Après retour à la température ambiante, on filtre le chlorure de méthacrylate de tertiobutylaminoéthyle qui a précipité, on le lave par 250 g d'hexane, on le sèche The reactor is charged with 370 g of tert-butylaminoethyl methacrylate, 0.48 g, hydroquinone methyl oxide and 1000 g of the solvent at atmospheric pressure. Is introduced at the temperature indicated in Table 1, with air bubbling III, lg of methyl chloride, over the time indicated in Table 1. At the end of the reaction, the unreacted methyl chloride is removed by entrainment in air at 60 C for 1 hour. The medium is cooled to 40 ° C. and drained. After returning to room temperature, the tert-butylaminoethyl methacrylate chloride which has precipitated is filtered, washed with 250 g of hexane and dried.
sous pression réduite à 40 C pendant 3 heures. under reduced pressure at 40 C for 3 hours.
Ce produit se présente sous la forme d'un solide blanc fondant à 103 C dont la structure a pu être déterminée par spectrométrie de masse et par analyse en R.M.N. (C13 et This product is in the form of a white solid melting at 103 C, the structure of which could be determined by mass spectrometry and by analysis in R.M.N. (C13 and
4 27072884 2707288
Hi).Hi).
Les résultats des essais sont résumés dans le tableau. The results of the tests are summarized in the table.
TableauBoard
Exemple Solvant Température Durée Rendement* ( C) (heures) (%) 1 Acetone 50 6 12 2 Acétonitrile 70 6 12 3 Méthyl ethyl 70 6 16 cetone 4 Méthyl ethyl 70 12 20 cetone Méthyl ethyl 85 12 54 cetone 6 Toluene 85 12 40 7 Méthyl isobuty_ 100 12 94 cetone * C'est le rendement stoechiométrique déterminé à partir du Example Solvent Temperature Duration Yield * (C) (hours) (%) 1 Acetone 50 6 12 2 Acetonitrile 70 6 12 3 Methyl ethyl 70 6 16 ketone 4 Methyl ethyl 70 12 20 ketone Methyl ethyl 85 12 54 ketone 6 Toluene 85 12 40 7 Methyl isobuty_ 100 12 94 cetone * This is the stoichiometric yield determined from the
dosage de chlorures présents dans le sel et le filtrat. determination of chlorides present in the salt and the filtrate.
Le spectre RMN donne les résultats suivants. On indique ci-après dans la formule la position des différents The NMR spectrum gives the following results. We indicate below in the formula the position of the different
carbones.carbons.
déplacement chimique du carbone (13) (b) (a) CH2 =C Oc CH3 C-0-CH2- CH2 2-C (C3) 3 Cl (c) (d) (e) (f) (g){h) d 166,7 ppm b 135,2 ppm a 126,9 ppm e 59,4 ppm g 57,4 ppm f 40,3 ppm h 25,3 ppm c 18,2 ppm Déplacement chimique du proton (a) H 0 chemical shift of carbon (13) (b) (a) CH2 = C Oc CH3 C-0-CH2- CH2 2-C (C3) 3 Cl (c) (d) (e) (f) (g) {h ) d 166.7 ppm b 135.2 ppm a 126.9 ppm e 59.4 ppm g 57.4 ppm f 40.3 ppm h 25.3 ppm c 18.2 ppm Chemical displacement of the proton (a) H 0
C= C- CC = C- C
0-CH2 - CH2 - NH2 C- (CH3)3 C10-CH2 - CH2 - NH2 C- (CH3) 3 C1
(b) H CH3(g) (c) (d) (e) (f) a et b doublets à 5.6 ppm et 6.27 ppm d'intensité 1 et 1 c triplet centré à 4.63ppm d'intensité 2 d multiplet centré à 3.2ppm d'intensité 2 e massif à 9.63 ppm d'intensité 2 f singulet à 1.47 ppm d'intensité 9 g singulet à 1.94 ppm d'intensité 3 (b) H CH3 (g) (c) (d) (e) (f) a and b doublets at 5.6 ppm and 6.27 ppm intensity 1 and 1 c triplet centered at 4.63ppm intensity 2 d multiplet centered at 3.2ppm of intensity 2 nd massif at 9.63 ppm of intensity 2 f singlet at 1.47 ppm of intensity 9 g singlet at 1.94 ppm of intensity 3
6E 27072886E 2707288
Claims (4)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9308184A FR2707288B1 (en) | 1993-07-05 | 1993-07-05 | Tertiary butylaminoethyl methacrylate chloride, process for its preparation and its applications. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9308184A FR2707288B1 (en) | 1993-07-05 | 1993-07-05 | Tertiary butylaminoethyl methacrylate chloride, process for its preparation and its applications. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2707288A1 true FR2707288A1 (en) | 1995-01-13 |
| FR2707288B1 FR2707288B1 (en) | 1995-09-01 |
Family
ID=9448891
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR9308184A Expired - Fee Related FR2707288B1 (en) | 1993-07-05 | 1993-07-05 | Tertiary butylaminoethyl methacrylate chloride, process for its preparation and its applications. |
Country Status (1)
| Country | Link |
|---|---|
| FR (1) | FR2707288B1 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0862858A1 (en) * | 1997-03-06 | 1998-09-09 | Hüls Aktiengesellschaft | Process for preparing antimicrobial plastics |
| EP0862859A1 (en) * | 1997-03-06 | 1998-09-09 | Hüls Aktiengesellschaft | Process for preparing antimicrobial plastics |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2744884A (en) * | 1954-07-20 | 1956-05-08 | Rohm & Haas | N-tert-alkylaminoalkyl esters |
| EP0376813A1 (en) * | 1988-12-28 | 1990-07-04 | Elf Atochem S.A. | Process for water purification using a polymeric flocculant |
| EP0398022A1 (en) * | 1989-04-20 | 1990-11-22 | Chemische Fabrik Stockhausen GmbH | Method for the separation of oil in water emulsions |
| EP0428970A1 (en) * | 1989-11-21 | 1991-05-29 | BASF Aktiengesellschaft | Process for preparing aqueous solutions or suspensions of quaternization products of tertiary aminoalkylesters or tertiary aminoalkylamides of acrylic or methacrylic acid, for instance of dimethylaminoethyl-acrylate-methochloride |
-
1993
- 1993-07-05 FR FR9308184A patent/FR2707288B1/en not_active Expired - Fee Related
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2744884A (en) * | 1954-07-20 | 1956-05-08 | Rohm & Haas | N-tert-alkylaminoalkyl esters |
| EP0376813A1 (en) * | 1988-12-28 | 1990-07-04 | Elf Atochem S.A. | Process for water purification using a polymeric flocculant |
| EP0398022A1 (en) * | 1989-04-20 | 1990-11-22 | Chemische Fabrik Stockhausen GmbH | Method for the separation of oil in water emulsions |
| EP0428970A1 (en) * | 1989-11-21 | 1991-05-29 | BASF Aktiengesellschaft | Process for preparing aqueous solutions or suspensions of quaternization products of tertiary aminoalkylesters or tertiary aminoalkylamides of acrylic or methacrylic acid, for instance of dimethylaminoethyl-acrylate-methochloride |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6203856B1 (en) | 1993-03-06 | 2001-03-20 | Huels Aktiengesellschaft | Process for the preparation of antimicrobial plastics |
| EP0862858A1 (en) * | 1997-03-06 | 1998-09-09 | Hüls Aktiengesellschaft | Process for preparing antimicrobial plastics |
| EP0862859A1 (en) * | 1997-03-06 | 1998-09-09 | Hüls Aktiengesellschaft | Process for preparing antimicrobial plastics |
| US5967714A (en) * | 1997-03-06 | 1999-10-19 | Huels Aktiengesellschaft | Process for the preparation of antimicrobial plastics |
| US6096800A (en) * | 1997-03-06 | 2000-08-01 | Huels Aktiengesellschaft | Process for the preparation of antimicrobial plastics |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2707288B1 (en) | 1995-09-01 |
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