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US3920644A Expired / Lapsed US ⏱️ 0.0 years remaining

Process for preparing halogen-containing organic isocyanates

Assignee: Kao Corp
•
Filing: 1974-07-12
•
Granted: 1975-11-18
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Expires: 1994-07-12
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Abstract

Abstract A process for preparing halogen-containing organic isocyanates, in which a benzene derivative having a chloromethyl group and an additional benzene-nucleus substituent having a steric interaction with the chloromethyl group and also having a halogen content of at least 80 percent by weight, said substituent being located ortho to the chloromethyl group, and an alkali metal cyanate, are heated at 60* to 190*C, in the presence of an amine compound that does not cause substitution with the chlorine atom of said chloromethyl group.

Inventors

  • 👤 Susumu Handa
  • 👤 Yoshiaki Tanaka
  • 👤 Atsushi Nishibata
  • 👤 Yoshiaki Inamoto

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-27 09:58
CPC Classifications
C; C07; C07C; C07C263/00; C07C263/02; Y; Y10; Y10S; Y10S521/00; Y10S521/902

Claims Analysis

Total Claims: 9
Claim 1
Independent Claim 247 words
A PROCESS FOR PREPARING HALOGEN-CONTAINING ORGANIC ISOCYANATES, WHICH COMPRISES: REACTING AT 60* TO 190*C, A. A BENZYL CHLORIDE DERIVATIVE OR A MIXTURE OF BENZYL CHLORIDE DERIVATIVES HAVING A NUCLEUS-SUBSTITUTED SUBSTITUENT LOCATED ORTHO TO THE CHLOROMELTHYL GROUP, SAID SUBSTITUENT HAVING A STERIC INTERACTION WITH THE CHLOROMETHYL GROUP AND HAVING A HALOGEN CONTENT OF AT LEAST 80 PERCENT BY WEIGHT, PROVIDED THAT SAID SUBSTITUENT IS NOT F FLUORINE ATOM, THE REMAINING CARBON ATOMS OF THE NUCLEUS BEING UNSUBSTITUTED OR SUBSTITUTED BY HAOLGEN, METHYLMONOHALIDES, METHYLIHALIDES, METHYLTRIHALIDES, VINYLDIBROMIDE, OR PHENYL, B. AN ALKALI METAL CYANATE SELECTED FROM THE GROUP CONSISTING OF LITHIUM CYANATE, SODIUM CYANATE, POTASSIUM CYANATE AND MIXTURES THEREOF, THE AMOUNT OF B BEING IN THE RANGE OF FROM 0.5 TO 2.5 MOLES PER MOLE OF CHLORINE ATOM OF THE CHLOROMETHYL GROUP OR GROUPS OF A, IN THE PRESENCE OF C. AT LEAST A CATALYTICALLY EFFECTIVE AMOUNT OF AN AMINE COMPOUND OR MIXTURE OF AMINE COMPOUNDS HAVING A STRUCTURE SUCH THAT IT DOES NOT CAUSE SUBSTITUTION WITH THE CHLORINE ATOM OF THE CHLOROMETHYL GROUP OF A. SAID AMINE COMPOUND BEING SELECTED FROM THE GROUP CONSISTING OF DIPHENYLAMINE, N-CYCLOHEXYLANILINE, TRIPHENYLAMINE, TRIMETHYLAMINE, TRIETHYLAMINE, TRIPROPYLAMINE, TRIBUTYLAMINE, DIMETHYLANILINE, DIETHYLANILE, PYRIDINE, PICOLINE, CORYDINE, QUINOLINE, NMETHYLMORPHOLINE, N-ETHYLMORPHOLINE, N-KPHENYLMORPHOLINE, TRIETHYLENE DIAMINE, N-METHYLPIPERIDINE, N-ETHYLPIPERDINE, N-ETHYLPIPERIDINE, N-PHENYLPIPERIDINE, N,N-DIMETHYLPIPERAZINE, N,N-''DIETHYLPIPERAZINE, DIMETHYL FORMAMIDE, DIETHYL FORMAMIDE, DIMETHYL ACETAMIDE, TETRAMETHYLUREA, N-METHYLPYRROLIDONE, FROMYLMORPLHOLINE, ACETYLMORPHOLINE, FORMLYPIPERIDINE, ACETYLPIPERIDINE, N-METHYL PHTHALIMIDE, AND QUATERNARY AMMONIUM SALTS FORMED FROM THE FOREGOING AMINES, UNTIL A HALOGEN-CONTAINING ORGANIC ISOCYANATE IS FORMED, AND RECOVERING FROM THE REACTION MIXTURE SAID HAOLGEN-CONTAINING ORGANIC ISOCYANATE.
Claim 2
Dependent Claim 247 words
A PROCESS FOR PREPARING HALOGEN-CONTAINING ORGANIC ISOCYANATES, WHICH COMPRISES: REACTING AT 60* TO 190*C, A. A BENZYL CHLORIDE DERIVATIVE OR A MIXTURE OF BENZYL CHLORIDE DERIVATIVES HAVING A NUCLEUS-SUBSTITUTED SUBSTITUENT LOCATED ORTHO TO THE CHLOROMELTHYL GROUP, SAID SUBSTITUENT HAVING A STERIC INTERACTION WITH THE CHLOROMETHYL GROUP AND HAVING A HALOGEN CONTENT OF AT LEAST 80 PERCENT BY WEIGHT, PROVIDED THAT SAID SUBSTITUENT IS NOT F FLUORINE ATOM, THE REMAINING CARBON ATOMS OF THE NUCLEUS BEING UNSUBSTITUTED OR SUBSTITUTED BY HAOLGEN, METHYLMONOHALIDES, METHYLIHALIDES, METHYLTRIHALIDES, VINYLDIBROMIDE, OR PHENYL, B. AN ALKALI METAL CYANATE SELECTED FROM THE GROUP CONSISTING OF LITHIUM CYANATE, SODIUM CYANATE, POTASSIUM CYANATE AND MIXTURES THEREOF, THE AMOUNT OF B BEING IN THE RANGE OF FROM 0.5 TO 2.5 MOLES PER MOLE OF CHLORINE ATOM OF THE CHLOROMETHYL GROUP OR GROUPS OF A, IN THE PRESENCE OF C. AT LEAST A CATALYTICALLY EFFECTIVE AMOUNT OF AN AMINE COMPOUND OR MIXTURE OF AMINE COMPOUNDS HAVING A STRUCTURE SUCH THAT IT DOES NOT CAUSE SUBSTITUTION WITH THE CHLORINE ATOM OF THE CHLOROMETHYL GROUP OF A. SAID AMINE COMPOUND BEING SELECTED FROM THE GROUP CONSISTING OF DIPHENYLAMINE, N-CYCLOHEXYLANILINE, TRIPHENYLAMINE, TRIMETHYLAMINE, TRIETHYLAMINE, TRIPROPYLAMINE, TRIBUTYLAMINE, DIMETHYLANILINE, DIETHYLANILE, PYRIDINE, PICOLINE, CORYDINE, QUINOLINE, NMETHYLMORPHOLINE, N-ETHYLMORPHOLINE, N-KPHENYLMORPHOLINE, TRIETHYLENE DIAMINE, N-METHYLPIPERIDINE, N-ETHYLPIPERDINE, N-ETHYLPIPERIDINE, N-PHENYLPIPERIDINE, N,N-DIMETHYLPIPERAZINE, N,N-''DIETHYLPIPERAZINE, DIMETHYL FORMAMIDE, DIETHYL FORMAMIDE, DIMETHYL ACETAMIDE, TETRAMETHYLUREA, N-METHYLPYRROLIDONE, FROMYLMORPLHOLINE, ACETYLMORPHOLINE, FORMLYPIPERIDINE, ACETYLPIPERIDINE, N-METHYL PHTHALIMIDE, AND QUATERNARY AMMONIUM SALTS FORMED FROM THE FOREGOING AMINES, UNTIL A HALOGEN-CONTAINING ORGANIC ISOCYANATE IS FORMED, AND RECOVERING FROM THE REACTION MIXTURE SAID HAOLGEN-CONTAINING ORGANIC ISOCYANATE.
Claim 3
Dependent Claim 29 words
A process according to claim 1, in which all nucleus substituents on said benzene derivative or derivatives are selected from the group consisting of halogen, methylmonohalides, methyldihalides and methyltrihalides.
Claim 4
Dependent Claim 21 words
A process according to claim 2, in which the halogen is selected from the group consisting of chlorine, bromine and fluorine.
Claim 5
Dependent Claim 22 words
A process according to claim 3, in which the halogen content of said additional substituent is at least 85 percent by weight.
Claim 6
Dependent Claim 16 words
A process according to claim 3, in which the reaction temperature is from 70* to 160*C.
Claim 7
Dependent Claim 39 words
A process according to claim 3, in which said benzyl chloride derivative or derivatives includes a compound having a single nucleus-substituted chloromethyl group which is transformed by the reaction to an isocyanatomethyl group in the halogencontaining organic isocyanate product.
Claim 8
Dependent Claim 100 words
A process according to claim 3, in which said benzyl chloride derivative or derivatives includes a compound having at least two chloromethyl groups one of which is not ortho to said additional substituent, the chloromethyl group ortho to said additional substituent being transformed by the reaction to an isocyanatomethyl group and the chloromethyl group not ortho to said additional substituent being transformed by the reaction to an isocyanatomethyl group which trimerizes to form an isocyanate ring whereby the halogen-containing organic isocyanate product comprises an isocyanate ring to the nitrogen atoms of which are attached benzyl moieties having isocyanatomethyl groups thereon.
Claim 9
Dependent Claim 27 words
A process according to claim 1 in which said amine compound is selected from the group consisting of dimethyl formamide, tetramethyl urea, N-methyl-pyrrolidone, diethylformamide, acetylpiperidine and N-formylmOrpholine.

References Cited (Backward Citations)

US2866802A Cited
US2866801A Cited
US2866803A Cited
US3017420A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1978-11-17 1979-05-19 1979-11-18 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1982-11-17 1983-05-19 1983-11-18 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1986-11-17 1987-05-19 1987-11-18 $7700.00 Window Closed / Lapsed

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