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US4772716A Expired / Lapsed US ⏱️ 0.0 years remaining

Oxazolidines containing silane groups

Assignee: Novartis Corp
•
Filing: 1987-07-06
•
Granted: 1988-09-20
•
Expires: 2007-07-06
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Abstract

Abstract Compounds of the general formula I ##STR1## in which R 1 is hydrogen, C 1 -C 12 -alkyl, C 5 -C 7 -cycloalkyl, phenyl or benzyl and R 2 is hydrogen or C 1 -C 4 -alkyl, or R 1 and R 2 , together with the C atom to which they are attached, form a 5-membered or 6-membered ring, and R 3 , R 4 , R 5 and R 6 are identical or different and are hydrogen, C 1 -C 12 -alkyl, phenyl which is unsubstituted or monosubstituted to trisubstituted by C 1 -C 4 -alkyl, halogen or C 1 -C 4 -alkoxy, or is a group of the formula --CH 2 OR 7 (II) in which R 7 is C 1 -C 12 -alkyl, phenyl which is unsubstituted or monosubstituted to trisubstituted by C 1 -C 4 -alkyl, halogen or C 1 -C 4 -alkoxy, or is --C(O)--R 8 , and R 8 is C 1 -C 12 -alkyl, and also not more than two of the radicals R 3 , R 4 , R 5 and R 6 are one or two groups of the formula --CH 2 CH 2 Si(OR 9 ) 3 (III), --CH 2 OC(O)CH 2 CH 2 Si(OR 9 ) 3 (IV), --CH 2 O(C m H 2m )Si(OR 9 ) 3 (V) or ##STR2## in which R 9 is C 1 -C 4 -alkyl or phenyl and m is a number from 1 to 8 and r is a number 1 or 2 and t is 0, 1 or 2 and R 1 is as defined above, and, in addition, compounds of the formula I in which R 4 and R 5 together form a group of the formula ##STR3## in which R 9 is as defined above and R 3 and R 6 in this case are hydrogen and n is 1 or 2 and, if n is 1, Z is an organic radical which is derived from a primary amine ZnH 2 and can contain one or two --Si(OR 9 ) 3 groups and, if n is 2, Z is a divalent organic radical derived from a diprimary diamine H 2 NZNH 2 ; subject to the proviso that the compounds of the formula I contain one to three --Si(OR 9 ) 3 groups, are suitable for use as adhesion promoters, particularly for moisture-curing epoxide and polyurethane resins.

Inventors

  • 👤 Rolf Mulhaupt
  • 👤 Hubert Simon

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-05 03:06
CPC Classifications
C; C07; C07F; C07F7/00; C07F7/02; C07F7/08; C07F7/18; C08; C08G; C08G18/00; C08G18/06; C08G18/08; C08G18/10; C07F7/1804; C08K; C08K5/00; C08K5/54

Claims Analysis

Total Claims: 20
Claim 1
Independent Claim 386 words
A compound of the general formula I ##STR44## in which R 1 is hydrogen, C 1 -C 12 -alkyl, C 5 -C 7 -cycloalkyl, phenyl or benzyl and R 2 is hydrogen or C 1 -C 4 -alkyl, or R 1 and R 2 , together with the C atom to which they are attached, form a 5-membered or 6-membered ring, and R 3 , R 4 , R 5 and R 6 are identical or different and are hydrogen, C 1 -C 12 -alkyl, phenyl which is unsubstituted or monosubstituted to trisubstituted by C 1 -C 4 -alkyl, halogen or C 1 -C 4 -alkoxy, or is a group of the formula --CH 2 OR 7 (II) in which R 7 is C 1 -C 12 -alkyl, phenyl which is unsubstituted or monosubstituted to trisubstituted by C 1 -C 4 -alkyl, halogen or C 1 -C 4 -alkoxy, or is --C(O)--R 8 , and R 8 is C 1 -C 12 -alkyl, and also not more than two of the radicals R 3 , R 4 , R 5 and R 6 are one or two groups of the formula --CH 2 CH 2 Si(OR 9 ) 3 (III), --CH 2 OC(O)CH 2 CH 2 Si(OR 9 ) 3 (IV), --CH 2 O(C m H 2m )Si(OR 9 ) 3 (V) or ##STR45## in which R 9 is C 1 -C 4 -alkyl or phenyl and m is a number from 1 to 8 and r is a number 1 or 2 and t is 0, 1 or 2 and R 1 is as defined above, and, in addition, compounds of the formula I in which R 4 and R 5 together form a group of the formula ##STR46## in which R 9 is as defined above and R 3 and R 6 in this case are hydrogen and n is 1 or 2 and, if n is 1, Z is an organic radical which is derived from a primary amine ZNH 2 and can contain one or two --Si(OR 9 ) 3 groups and, if n is 2, Z is a divalent organic radical derived from a diprimary diamine H 2 NZNH 2 ; subject to the proviso that the compounds of the formula I contain one to three --Si(OR 9 ) 3 groups.
Claim 2
Dependent Claim 386 words
A compound of the general formula I ##STR44## in which R 1 is hydrogen, C 1 -C 12 -alkyl, C 5 -C 7 -cycloalkyl, phenyl or benzyl and R 2 is hydrogen or C 1 -C 4 -alkyl, or R 1 and R 2 , together with the C atom to which they are attached, form a 5-membered or 6-membered ring, and R 3 , R 4 , R 5 and R 6 are identical or different and are hydrogen, C 1 -C 12 -alkyl, phenyl which is unsubstituted or monosubstituted to trisubstituted by C 1 -C 4 -alkyl, halogen or C 1 -C 4 -alkoxy, or is a group of the formula --CH 2 OR 7 (II) in which R 7 is C 1 -C 12 -alkyl, phenyl which is unsubstituted or monosubstituted to trisubstituted by C 1 -C 4 -alkyl, halogen or C 1 -C 4 -alkoxy, or is --C(O)--R 8 , and R 8 is C 1 -C 12 -alkyl, and also not more than two of the radicals R 3 , R 4 , R 5 and R 6 are one or two groups of the formula --CH 2 CH 2 Si(OR 9 ) 3 (III), --CH 2 OC(O)CH 2 CH 2 Si(OR 9 ) 3 (IV), --CH 2 O(C m H 2m )Si(OR 9 ) 3 (V) or ##STR45## in which R 9 is C 1 -C 4 -alkyl or phenyl and m is a number from 1 to 8 and r is a number 1 or 2 and t is 0, 1 or 2 and R 1 is as defined above, and, in addition, compounds of the formula I in which R 4 and R 5 together form a group of the formula ##STR46## in which R 9 is as defined above and R 3 and R 6 in this case are hydrogen and n is 1 or 2 and, if n is 1, Z is an organic radical which is derived from a primary amine ZNH 2 and can contain one or two --Si(OR 9 ) 3 groups and, if n is 2, Z is a divalent organic radical derived from a diprimary diamine H 2 NZNH 2 ; subject to the proviso that the compounds of the formula I contain one to three --Si(OR 9 ) 3 groups.
Claim 3
Dependent Claim 52 words
A compound according to claim 1 of the formula I in which, if n is 1, Z is derived from an aliphatic, cycloaliphatic, aliphatic/aromatic, aromatic or heterocyclic primary amine, it being possible for this linear or branched radical Z to contain one or more ester, ether, urethane, thiourethane, aldimine or ketimine groups.
Claim 4
Dependent Claim 52 words
A compound according to claim 1 of the formula I in which, if n is 1, Z is derived from an aliphatic, or mixed aliphatic/aromatic, primary amine, this radical Z containing, a total of one or two ester, ether, urethane, thiourethane, aldimine or ketimine groups, or being derived from an aromatic amine.
Claim 5
Dependent Claim 15 words
A compound according to claim 1 of the formula I in which n is 1.
Claim 6
Dependent Claim 26 words
A compound according to claim 1 of the formula I in which n is 1 and Z is a group of the formula --C.sub.m H.sub.2m)Si(OR.sup.9).sub.3 (VIII)
Claim 7
Dependent Claim 74 words
A compound according to claim 1 of the formula I in which n is 1 and Z is a group of the formula --[(R.sup.10)C(R.sup.11)].sub.u --O--R.sup.12 (IX), --(R.sup.10)C(R.sup.11)--C(O)O(CH.sub.2).sub.3 Si(OR.sup.9).sub.3 (X) in which u is 2, 3 or 4 and R 10 and R 11 are hydrogen or methyl and R 12 is a group of the formula ##STR47## in which the symbols m, t, R 1 and R 9 are as defined in claim 1.
Claim 8
Dependent Claim 53 words
A compound according to claim 1 of the formula I in which n is 1 and Z is a group of the formula --[(R.sup.10)C(R.sup.11)].sub.u --OR.sup.7 (XVII) in which u is 2, 3 or 4 and R 10 and R 11 are hydrogen or methyl, and R 7 is as defined in claim 1.
Claim 9
Dependent Claim 15 words
A compound according to claim 1 of the formula I in which n is 2.
Claim 10
Dependent Claim 36 words
A compound according to claim 1 of the formula I in which n is 2 and Z is a divalent aliphatic, cycloaliphatic, aromatic or heterocyclic radical derived from a diprimary diamine H 2 NZNH 2 (VIII).
Claim 11
Dependent Claim 29 words
A compound according to claim 1 of the formula I in which R 1 and R 2 independently of one another are hydrogen or C 1 -C 4 -alkyl.
Claim 12
Dependent Claim 41 words
A compound according to claim 1 of the formula I in which R 3 , R 4 , R 5 and R 6 are hydrogen or C 1 -C 4 -alkyl, and not more than two of these radicals are phenoxymethyl.
Claim 13
Dependent Claim 29 words
A compound according to claim 1 of the formula I in which R 3 and R 6 are hydrogen and R 4 and R 5 are hydrogen or methyl.
Claim 14
Dependent Claim 38 words
A compound according to claim 1 of the formula I in which one of the radicals R 3 , R 4 , R 5 or R 6 is a group of the formulae (III), (IV), (V) or (VI).
Claim 15
Dependent Claim 33 words
A compound according to claim 1 of the formula I in which R 4 and R 5 together are a group of the formula VII, and R 3 and R 6 are hydrogen.
Claim 16
Dependent Claim 23 words
A compound according to claim 1 of the formula I which contains one or two --Si(OR 9 ) 3 groups in its molecule.
Claim 17
Dependent Claim 22 words
A compound according to claim 4 of the formula I which contains an --Si(OR 9 ) 3 group in the substituent Z.
Claim 18
Dependent Claim 46 words
A compound according to claim 4 of the formula I which contains an --Si(OR 9 ) 3 group in the substituent Z and an --Si(OR 9 ) 3 group in one of the radicals R 3 , R 4 , R 5 or R 6 .
Claim 19
Dependent Claim 37 words
A compound according to claim 4 of the formula I which contains one or two --Si(OR 9 ) 3 groups in one of the substituents R 3 , R 4 , R 5 or R 6 .
Claim 20
Dependent Claim 21 words
A compound according to claim 8 of the formula I which contains a total of two --Si(OR 9 ) 3 groups.

References Cited (Backward Citations)

US3274210A Cited
US3743626A Cited
US4028343A Cited
EP0096768A2 Cited
DE3414877A1 Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1991-09-20 1992-03-21 1992-09-20 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1995-09-20 1996-03-21 1996-09-20 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1999-09-20 2000-03-21 2000-09-20 $7700.00 Window Closed / Lapsed

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