Claims
- 1. A method for producing a betaine-type product which comprises reacting, at a temperature of about 0.degree. C. to about 100.degree. C., 1. acrylic acid with a tertiary amine of the formula ##STR6##wherein R is (C.sub.1 -C.sub.24) alkyl, allyl, benzyl, vinylbenzyl, hydroxyalkyl having 2 to 24 carbon atoms, (C.sub.1 -C.sub.8)-alkyl substituted by an acryloxy, methacryloxy, acrylamido or methacrylamido, alkoxyalkyl having 3 to 24 carbon atoms, or a poly(alkoxy)alkyl group having 2 to 6 oxygen atoms and 2 to 3 carbon atoms in all except one of the terminal alkyl groups, the latter having 1 to 8 carbon atoms; R' is a (C.sub.1 -C.sub.8) alkyl group; R.degree. is a (C.sub.1 -C.sub.8) alkyl group, or R' and R.degree. may be joined together and form with the N atom of the tertiary amine, a ring selected from morpholino, thiomorpholino, N-alkylpiperidino, or piperazino or
- 2.
- 2. acrylic acid with a polymer containing tertiary amine groups, of the formula above where R is (C.sub.1 -C.sub.8) alkyl substituted by acryloxy, methacryloxy, acrylamido or methacrylamido, and R' and R.degree. are as defined above, or
- 3. acrylic acid with a mixture of a tertiary amine as defined in (2) and (b) a polymer of said tertiary amine, the molar ratio of acid to amine in
- the mixtures (1), (2), and (3) being from 0.1:1 to 10:1. 2. A method according to claim 1 in which the molar ratio of acid to amine is about 1:1 to 5:1.
- 3. A method for producing a betaine-type product which comprises reacting, in an aqueous medium at a temperature of about 0.degree. to about 80.degree. C.
- acrylic acid with a tertiary amine of the formula, ##STR7##wherein R is (C.sub.1 -C.sub.24) alkyl, allyl, benzyl, vinylbenzyl, hydroxyalkyl having 2 to 24 carbon atoms, (C.sub.1 -C.sub.8) alkyl substituted by an acryloxy, methacryloxy, acrylamido or methacrylamido, alkoxyalkyl having 3 to 24 carbon atoms, or a poly(alkoxy)alkyl group having 2 to 6 oxygen atoms and 2 to 3 carbon atoms in all except one of the terminal alkyl groups, the latter having 1 to 8 carbon atoms; R' is (C.sub.1 -C.sub.8) alkyl; R.degree. is (C.sub.1 -C.sub.8) alkyl, or R' and R.degree. may be joined together and form with the N atom of the tertiary amine, a ring selected from morpholino, thiomorpholino, N-alkylpiperidino, or piperazino.
- 4. A method for producing a betaine-type product which comprises reacting, in an aqueous medium at a temperature of about 0.degree. to about 80.degree. C.,
- 1. acrylic acid, with a polymer containing tertiary amine groups of the formula ##STR8##wherein R is (C.sub.1 -C.sub.8) alkyl substituted by an acryloxy, methacryloxy, acrylamido or methacrylamido R' and R.degree. are (C.sub.1 -C.sub.8) alkyl, or R' and R.degree. are joined together with the N atom to form morpholino, thiomorpholino, N-alkylpiperidino or piperzino or
- 2. acrylic acid with a mixture of (a) a tertiary amine of the formula as defined above in (1) and (b) a polymer of said teritary amine, the molar ratio of acid to amine being from 0.1 to 10:1.
- 5. A method according to claim 1 in which the reaction is effected at a temperature of about 10.degree. C. to 40.degree. C.
- 6. A method for producing a betaine-type product which comprises reacting, at a temperature of about 0.degree. C. to about 100.degree. C., acrylic acid with a tertiary amine of the formula ##STR9##wherein R is (C.sub.1 -C.sub.24) alkyl, allyl, benzyl, vinylbenzyl, hydroxyalkyl having 2 to 24 carbon atoms, (C.sub.1 -C.sub.8)-alkyl substituted by an acryloxy, methacryloxy, acrylamido or methacrylamido, alkoxyalkyl having 3 to 24 carbon atoms, or poly(alkoxy)alkyl having 2 to 6 oxygen atoms and 2 to 3 carbon atoms in all except one of the terminal alkyl groups, the latter having 1 to 8 carbon atoms; R' is (C.sub.1 -C.sub.8) alkyl; R.degree. is a (C.sub.1 -C.sub.8) alkyl group, or R' and R.degree. may be joined together and form with the N atom of the tertiary amine, a ring selected from morpholino, thiomorpholino, N-alkylpiperidino, or piperazino.
- 7. A method according to claim 1 ##STR10##wherein R is (C.sub.1 -C.sub.8) alkyl substituted by acryloxy, methacryloxy, acrylamido or methacrylamido, R' is (C.sub.1 -C.sub.4) alkyl, and R.degree. is (C.sub.1 -C.sub.4) alkyl.
- 8. A method according to claim 1 in which the tertiary amine is dimethylaminoethyl acrylate dimethylaminoethyl methacrylate, N-dimethylaminoethyl acrylamide or N-dimethylaminoethyl methacrylamide or a polymer containing units thereof.
- 9. A method according to claim 3 in which the reaction is effected at a temperature of about 10.degree. C. to 40.degree. C.
- 10. A method according to claim 3 wherein R is (C.sub.1 -c.sub.8) alkyl substituted by acryloxy, methacryloxy, acrylamido or methacrylamido; R' is (C.sub.1 -C.sub.4) alkyl and R.degree. is (C.sub.1 -C.sub.4) alkyl.
- 11. A method according to claim 3 wherein the tertiary amine is dimethylaminoethyl acrylate, dimethylaminoethyl methacrylate, N-dimethylaminoethyl acrylamide or N-dimethylaminoethyl methacrylamide or a polymer containing said amines.
- 12. A process according to claim 3 for preparing a betaine-type product having the formula ##STR11##which comprises reacting acrylic acid with .beta.-N, N-dimethylaminoethyl methacrylate at 25.degree. C.
- 13. A method for producing a betaine-type product which comprises reacting, in an aqueous medium at a temperature of about 0.degree. to about 80.degree. C., a lower alkyl ester of acrylic acid with a tertiary aliphatic amine of the formula ##STR12##wherein R is (C.sub.1 -C.sub.24) alkyl, allyl, benzyl, vinylbenzyl, hydroxyalkyl having 2 to 24 carbon atoms, a (C.sub.1 -C.sub.8) alkyl substituted by an acryloxy, methacryloxy, acrylamido or methacrylamido group, alkoxyalkyl having 3 to 24 carbon atoms in all except one of the terminal alkyl groups, the latter having 1 to 8 carbon atoms; R' is (C.sub.1 -C.sub.8) alkyl; R.degree. is (C.sub.1 -C.sub.8) alkyl, or R' and R.degree. may be joined together and form with the N atom of the tertiary amine, a ring selected from morpholino, thiomorpholino, N-alkylpiperidino, or piperazino.
- 14. A method according to claim 13 wherein R is (C.sub.1 -C.sub.8) alkyl substituted by acryloxy, methacryloxy, acrylamido or methacrylamido the molar ratio of acid to amine being from 0:1 to 10:1.
- 15. A method according to claim 13 wherein R is (C.sub.1 -C.sub.8) alkyl substituted by an acryloxy, methacryloxy, acrylamido or methacrylamido; R' is (C.sub.1 -C.sub.4) alkyl, and R.degree. is (C.sub.1 -C.sub.4) alkyl.
- 16. A method according to claim 13 wherein the tertiary amine is dimethylaminoethyl acrylate, dimethylaminoethyl methacrylate, N-dimethylaminoethyl acrylamide or N-dimethylaminoethyl methacrylamide or a polymer containing units thereof.
- 17. A method according to claum 13 in which the reaction is conducted at a temperature in the range of from about 10.degree. C. to 40.degree. C.
- 18. A method according to claim 13 wherein R is (C.sub.1 -C.sub.24) alkyl, allyl, benzyl, vinylbenzyl, hydroxyalkyl having 2 to 24 carbon atoms, alkoxyalkyl having 3 to 24 carbon atoms, or poly (alkoxy)alkyl having 2 to 6 oxygen atoms and 2 to 3 carbon atoms in all except one of the terminal alkyl groups, the latter having 1 to 8 carbon atoms; R' is (C.sub.1 -C.sub.8) alkyl; R.degree. is (C.sub.1 -C.sub.8) alkyl, or R' and R.degree. are joined together and form, with the N atom of the tertiary amine, a ring selected from morpholino, thiomorpholino, N-alkylpiperidino, or piperazino.
- 19. A method for producing a betaine-type product which comprises reacting at a temperature of about 0.degree.-100.degree. C., a mixture of acrylic acid with a polymer of tertiary aliphatic amine groups of the formula: ##STR13##wherein R is allyl, vinylbenzyl, or (C.sub.1 -C.sub.8) alkyl substituted by an acryloxy, methacryloxy, acrylamido or methacrylamido; R' is (C.sub.1 -C.sub.8) alkyl; R.degree. is (C.sub.1 -C.sub.8) alkyl or R' and R.degree. may be joined together and form with the N atom of the tertiary amine, a ring selected from morpholino, thiomorpholino, N-alkylpiperidino, or piperazino.
- 20. A method according to claim 19 in which the reaction is effected at a temperature of about 10.degree. C. to 40.degree. C.
- 21. A method according to claim 3 wherein R is (C.sub.1 -C.sub.8) alkyl substituted by acryloxy, methacryloxy acrylamido or methacrylamido; R' is (C.sub.1 -C.sub.4) alkyl and R.degree. is (C.sub.1 -C.sub.4) alkyl.
- 22. The method of claim 3 in which a polymer of a tertiary aliphatic amine groups of the formula: ##STR14##wherein R is allyl, vinylbenzyl, or (C.sub.1 -C.sub.8) alkyl substituted by an acryloxy, methacryloxy, acrylamido or methacrylamido; R' is (C.sub.1 -C.sub.8) alkyl; R.degree. is (C.sub.1 -C.sub.8) alkyl or R' and R.degree. may be joined together and form with the N atom of the tertiary amine, a ring selected from morpholino, thiomorpholino, N-alkylpipereidino, or piperazino, is present during the reaction of the acrylic acid and the tertiary amine.
- 23. The method of claim 13 in which a polymer of a tertiary amine of the formula: ##STR15##wheren R is allyl, vinylbenzyl, or (C.sub.1 -C.sub.8) alkyl substituted by an acryloxy, methacryloxy, acrylamido or methacrylamido; R' is (C.sub.1 -C.sub.8) alkyl; R.degree. is (C.sub.1 -C.sub.8) alkyl or R' and R.degree. may be joined together and form with the N atom of the tertiary amine, a ring selected from morpholino, thiomorpholino, N-alkylpiperidino, or piperazino, is present during the reaction of the acrylic acid and the tertiary amine.
Parent Case Info
This is a continuation-in-part of our copending application Ser. No. 856,822, filed Sept. 10, 1969, U.S. Pat. No. 3,689,470.
US Referenced Citations (1)
Number |
Name |
Date |
Kind |
2777872 |
Shacklett |
Jan 1957 |
|
Foreign Referenced Citations (1)
Number |
Date |
Country |
1,487,622 |
Jun 1967 |
FR |