US4314948A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Preparation of mixtures of 1-monohalogenated isocyanates and 1,2-unsaturated isocyanates
Assignee: BASF SE
•
Filing: 1980-08-05
•
Granted: 1982-02-09
•
Expires: 2000-08-05
Abstract
Abstract 1-Monohalogenated isocyanates, and a process for the preparation of mixtures of 1-monohalogenated isocyanates and 1,2-unsaturated isocyanates by reacting 1-monohalogenated carbamic acid halides or isocyanates with a halogen-free isocyanate or diisocyanate or by reacting 1,2-unsaturated isocyanates with a carbamic acid halide or a bis-carbamic acid halide. The 1,2-unsaturated isocyanates and 1-monohalogenated isocyanates prepared according to the invention are valuable starting materials for the preparation of pest control agents, dyes, drugs, water-repellent textile finishes, detergents, plastics, bleaches and adhesives.
Inventors
- 👤 Karl-Heinz Koenig
- 👤 Karl-Heinz Feuerherd
- 👤 Heinz-Guenter Oeser
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 10:27
CPC Classifications
C; C07; C07C; C07C263/00; C07C263/16
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
116 words
A process for the preparation of a mixture of 1-monohalogenated isocyanates of the formula ##STR9## and 1,2-unsaturated isocyanates of the formula ##STR10## where R 1 , R 2 and R 3 may be identical or different and each is hydrogen, alkyl of 1 to 6 carbon atoms or phenyl, or the pair of radicals R 1 and R 2 together with the two adjacent carbon atoms, or the pair of radicals R 2 and R 3 together with the adjacent carbon atom, can also form members of a 5-membered or 6-membered alicyclic ring, R 1 , R 2 and R 3 in total contain up to 8 carbon atoms, and X is chlorine or bromine, wherein
Claim 2
Dependent Claim
116 words
A process for the preparation of a mixture of 1-monohalogenated isocyanates of the formula ##STR9## and 1,2-unsaturated isocyanates of the formula ##STR10## where R 1 , R 2 and R 3 may be identical or different and each is hydrogen, alkyl of 1 to 6 carbon atoms or phenyl, or the pair of radicals R 1 and R 2 together with the two adjacent carbon atoms, or the pair of radicals R 2 and R 3 together with the adjacent carbon atom, can also form members of a 5-membered or 6-membered alicyclic ring, R 1 , R 2 and R 3 in total contain up to 8 carbon atoms, and X is chlorine or bromine, wherein
Claim 3
Dependent Claim
140 words
(a1) 1-monohalogenated carbamic acid halides of the formula ##STR11## where R 1 , R 2 , R 3 and X have the above meanings, are reacted with a halogen-free isocyanate of the formula R.sup.4 --N═C═O III where R 4 is alkyl, cycloalkyl, aryl, aralkyl or alkylaryl, and/or (a2) with a diisocyanate of the formula O═C═N--R.sup.5 --N═C═O IV where R 5 is alkylene, cycloalkylene, arylene, alkylarylene or arylalkylene, or (b1) 1,2-unsaturated isocyanates Ib are reacted with a 1-halogen-free carbamic acid halide of the formula ##STR12## where R 4 and X have the above meanings and/or (b2) with a bis-carbamic acid halide of the formula ##STR13## where R 5 and X have the above meanings, and/or (b3) with a 1-monohalogenated carbamic acid halide II or (c1) 1-monohalogenated isocyanates Ia are reacted with a halogen-free isocyanate III and/or (c2) with a diisocyanate IV.
Claim 4
Dependent Claim
140 words
(a1) 1-monohalogenated carbamic acid halides of the formula ##STR11## where R 1 , R 2 , R 3 and X have the above meanings, are reacted with a halogen-free isocyanate of the formula R.sup.4 --N═C═O III where R 4 is alkyl, cycloalkyl, aryl, aralkyl or alkylaryl, and/or (a2) with a diisocyanate of the formula O═C═N--R.sup.5 --N═C═O IV where R 5 is alkylene, cycloalkylene, arylene, alkylarylene or arylalkylene, or (b1) 1,2-unsaturated isocyanates Ib are reacted with a 1-halogen-free carbamic acid halide of the formula ##STR12## where R 4 and X have the above meanings and/or (b2) with a bis-carbamic acid halide of the formula ##STR13## where R 5 and X have the above meanings, and/or (b3) with a 1-monohalogenated carbamic acid halide II or (c1) 1-monohalogenated isocyanates Ia are reacted with a halogen-free isocyanate III and/or (c2) with a diisocyanate IV.
Claim 5
Dependent Claim
33 words
A process as claimed in claim 1, wherein the reaction, in the case of process (a1), is carried out with from 15 to 25 moles of compound III per mole of compound II.
Claim 6
Dependent Claim
33 words
A process as claimed in claim 1, wherein the reaction, in the case of process (a2), is carried out with from 3 to 14 moles of compound IV per mole of compound II.
Claim 7
Dependent Claim
33 words
A process as claimed in claim 1, wherein the reaction, in the case of process (b1), is carried out with from 0.5 to 1 mole of compound V per mole of compound Ib.
Claim 8
Dependent Claim
33 words
A process as claimed in claim 1, wherein the reaction, in the case of process (b2), is carried out with from 0.25 to 0.5 mole of compound VI per mole of compound Ib.
Claim 9
Dependent Claim
33 words
A process as claimed in claim 1, wherein the reaction, in the case of process (b3), is carried out with from 0.5 to 1 mole of compound II per mole of compound Ib.
Claim 10
Dependent Claim
33 words
A process as claimed in claim 1, wherein the reaction, in the case of process (c1), is carried out with from 7 to 13 moles of compound III per mole of compound Ia.
Claim 11
Dependent Claim
33 words
A process as claimed in claim 1, wherein the reaction, in the case of process (c2), is carried out with from 1 to 8 moles of compound IV per mole of compound Ia.
Claim 12
Dependent Claim
19 words
A process as claimed in claim 1, wherein the reaction is carried out at from 0° to 150° C.
Claim 13
Dependent Claim
17 words
A process as claimed in claim 1, wherein the reaction time is from 0.1 to 5 hours.
References Cited (Backward Citations)
DE1418666A1
Cited
US3468923A
Cited
US3535360A
Cited
US3437680A
Cited
DE2639931A1
Cited
US4231952A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1985-02-08 | 1985-08-10 | 1986-02-09 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-02-08 | 1989-08-10 | 1990-02-09 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-02-08 | 1993-08-10 | 1994-02-09 | $7700.00 | Window Closed / Lapsed |