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Cycloaminals and a process for their preparation

Assignee: Bayer AG
•
Filing: 1978-08-21
•
Granted: 1983-09-13
•
Expires: 1998-08-21
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Abstract

Abstract The present invention is concerned with a new class of compounds prepared by reacting cyclic aminals of the formula ##STR1## with polyisocyanates of the formula R 5 (NCO) m+n to yield ##STR2## and with this process for obtaining said compounds, as well as the use of such compounds in polyurethane chemistry. If such compounds are free of isocyanates (n=0) they are useful as latent cross-linkers or hardeners activatable by heat or moisture. If such compounds carry free isocyanate groups (n=1 or 2) there are useful as synthetic resin precursors. In the above formulae m represents an integer of from 1 to 3, and n represents 0, 1 or 2, and the sum of m+n is 2 or 3, R 1 represents an aliphatic hydrocarbon group which is optionally cyano-substituted and which has from 1 to 6 carbon atoms, a cycloaliphatic hydrocarbon group having from 5-10 carbon atoms or an araliphatic hydrocarbon group having from 7-10 carbon atoms; R 2 represents a divalent aliphatic hydrocarbon group having from 2 to 6 carbon atoms, at least two carbon atoms being situated between the two nitrogen atoms; R 3 and R 4 are identical or different and represent hydrogen, aliphatic hydrocarbon groups having from 1 to 18 carbon atoms, cycloaliphatic hydrocarbon groups having from 5 to 10 carbon atoms or aromatic hydrocarbon groups having from 6 to 10 carbon atoms, or the two groups R 3 and R 4 together with the carbon atom of the heterocyclic ring may also form a 5-membered or 6-membered cycloaliphatic ring; and R 5 represents an (m+n)-valent group such as that which can be obtained by the removal of m+n isocyanate groups from an (m+n)-valent polyisocyanate.

Inventors

  • 👤 Manfred Hajek
  • 👤 Kuno Wagner
  • 👤 Walter Uerdingen
  • 👤 Wolfgang Wellner

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-05 17:01
CPC Classifications
C; C07; C07D; C07D239/00; C07D239/02; C07D239/04; C07D233/00; C07D233/02; C08; C08G; C08G18/00; C08G18/06; C08G18/70; C08G18/72; C08G18/80; C08G18/8061; C08G18/807; C08G18/808

Claims Analysis

Total Claims: 9
Claim 1
Independent Claim 190 words
Compounds corresponding to the following formula: ##STR19## wherein m represents an integer of from 1 to 3 and n represents 0, 1 or 2 and the sum of m+n is 2 or 3; R 1 represents an aliphatic hydrocarbon group which is optionally cyano-substituted and which has from 1 to 6 carbon atoms, a cycloaliphatic hydrocarbon group having from 5 to 10 carbon atoms or an araliphatic hydrocarbon group having from 7 to 10 carbon atoms; R 2 represents a divalent aliphatic hydrocarbon group having from 2 to 6 carbon atoms, at least two carbon atoms being arranged between the two nitrogen atoms; R 3 and R 4 are identical or different and represent hydrogen, aliphatic hydrocarbon groups having from 1 to 18 carbon atoms, cycloaliphatic hydrocarbon groups having from 5 to 10 carbon atoms or aromatic hydrocarbon groups having from 6 to 10 carbon atoms or the two groups R 3 and R 4 together with the carbon atom of the heterocyclic ring may form a 5-membered or 6-membered cycloaliphatic ring; R 5 represents the (m+n)-valent group obtained by the removal of m+n isocyanate groups from an (m+n)-valent polyisocyanate.
Claim 2
Dependent Claim 190 words
Compounds corresponding to the following formula: ##STR19## wherein m represents an integer of from 1 to 3 and n represents 0, 1 or 2 and the sum of m+n is 2 or 3; R 1 represents an aliphatic hydrocarbon group which is optionally cyano-substituted and which has from 1 to 6 carbon atoms, a cycloaliphatic hydrocarbon group having from 5 to 10 carbon atoms or an araliphatic hydrocarbon group having from 7 to 10 carbon atoms; R 2 represents a divalent aliphatic hydrocarbon group having from 2 to 6 carbon atoms, at least two carbon atoms being arranged between the two nitrogen atoms; R 3 and R 4 are identical or different and represent hydrogen, aliphatic hydrocarbon groups having from 1 to 18 carbon atoms, cycloaliphatic hydrocarbon groups having from 5 to 10 carbon atoms or aromatic hydrocarbon groups having from 6 to 10 carbon atoms or the two groups R 3 and R 4 together with the carbon atom of the heterocyclic ring may form a 5-membered or 6-membered cycloaliphatic ring; R 5 represents the (m+n)-valent group obtained by the removal of m+n isocyanate groups from an (m+n)-valent polyisocyanate.
Claim 3
Dependent Claim 56 words
A process for the preparation of compounds according to claim 1, wherein the cyclic aminals corresponding to the following formula: ##STR20## are reacted with polyisocyanates corresponding to the formula: R.sub.5 (NCO).sub.m+n wherein R 1 , R 2 , R 3 , R 4 , R 5 , m and n are defined as in claim 1.
Claim 4
Dependent Claim 127 words
The compounds of claim 1 wherein R 1 represents an aliphatic hydrocarbon group having from 1 to 3 carbon atoms which, if it has at least two carbon atoms, may have a cyano substituent in the 2-position, or it represents a cyclohexyl group, R 2 represents a dimethylene or trimethylene group, R 3 and R 4 represent, independently of each other, hydrogen, an aliphatic hydrocarbon group having from 1 to 3 carbon atoms, or, together with the carbon atom of the heterocyclic ring, a cyclohexyl group, R 5 represents the divalent group obtained by the removal of the isocyanate groups from hexamethylene diisocyanate, 2,4- and/or 2,6-diisocyanatotoluene, 4,4'-diisocyanatodiphenylmethane or 1-isocyanato-3,3,5-trimethyl-5-isocyanatomethyl-cyclohexane, n represents 0 or 1, and m represents 1 or 2, and the sum of n+m is 2.
Claim 5
Dependent Claim 70 words
A process for the preparation of the cycloaminals of claim 1 comprising reacting a cyclic aminal of the formula: ##STR21## wherein R 1 , R 2 , R 3 and R 4 are as defined in claim 3 with an isocyanate selected from the group consisting of 2,4- and/or 2,6-diisocyanatotoluene, 4,4'-diisocyanatodiphenyl methane and 1-isocyanato-3,3,5-trimethyl-5-isocyanato methyl cyclohexane at about 10° to 80° C. with subsequent separation of any unreacted cyclic aminal.
Claim 6
Dependent Claim 24 words
The process of claim 2 wherein the polyisocyanate is the reaction product of a monomeric diisocyanate and a deficient amount of a dihydroxy polyol.
Claim 7
Dependent Claim 12 words
The process of claim 2 wherein an excess of polyisocyanate is used.
Claim 8
Dependent Claim 14 words
The process of claim 2 wherein less than an equivalent of polyisocyanate is used.
Claim 9
Dependent Claim 16 words
The process of claim 2 wherein the cyclic aminal to isocyanate group ratio is about 1:1.

References Cited (Backward Citations)

US3661923A Cited
US3743626A Cited
US3864335A Cited
US3591590A Cited
US3778439A Cited
US3723454A Cited
US4002601A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1986-09-12 1987-03-14 1987-09-13 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1990-09-12 1991-03-14 1991-09-13 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1994-09-12 1995-03-14 1995-09-13 $7700.00 Window Closed / Lapsed

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