IP Library Granted Patent US 8,729,210
Granted Patent B2
US 8,729,210 · App. 12/837,536 · Granted May 20, 2014

Prepolymers based on di- or polyisocyanates and formamide-terminated low molecular weight compounds, processes for preparing the same and uses thereof

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Quick Facts
Patent No.
US 8,729,210
App. No.
12/837,536
Granted
May 20, 2014
Kind
B2
Abstract

Prepolymers, which are accessible from formamides of low molecular weight di- or triamines (formamide-terminated low molecular weight compounds) and di- or polyisocyanates, of the general formula (II): X—[—N(CHO)—CO—NH—R 1 —NCO] n   (II) wherein X represents a linear or branched aliphatic, cycloaliphatic, heterocyclic and/or aromatic structural unit having 2 to 40 carbon atoms, and which is optionally further substituted and/or optionally comprises one or more heteroatoms, wherein R 1 represents an organic radical which may optionally contain one or more heteroatoms and which may further contain one or more additional free isocyanate groups and/or one or more urethane, biuret, carbodiimide, isocyanurate, allophanate, iminooxadiazinedione and/or uretdione structural units, and wherein n≧2; processes for making the same; compositions containing the same; and uses thereof.

Claims (15)

1. A prepolymer of the general formula (II):

X—[—N(CHO)—CO—NH—R 1 —NCO] n   (II)

wherein X represents a linear or branched aliphatic, cycloaliphatic, heterocyclic and/or aromatic structural unit having 2 to 20 carbon atoms, which is free of polyether structural units and which is optionally further substituted and/or optionally comprises one or more heteroatoms; wherein R 1 represents an organic radical which may optionally contain one or more heteroatoms and which may further contain one or more additional free isocyanate groups and/or one or more urethane, biuret, carbodiimide, isocyanurate, allophanate, iminooxadiazinedione and/or uretdione structural units; and wherein n≧2.

2. The prepolymer according to claim 1 , wherein R 1 represents an aliphatic hydrocarbon radical having 4 to 36 carbon atoms, a cycloaliphatic hydrocarbon radical having 6 to 15 carbon atoms, an aromatic hydrocarbon radical having 6 to 15 carbon atoms or an araliphatic hydrocarbon radical having 7 to 15 carbon atoms which may optionally contain one or more heteroatoms and which may further contain one or more additional free isocyanate groups and/or one or more urethane, biuret, carbodiimide, isocyanurate, allophanate, iminooxadiazinedione and/or uretdione structural units.

3. The prepolymer according to claim 1 , wherein X represents a structural unit derived from a polyamine X(NH 2 ) n , wherein n≧2, selected from the group consisting of ethylenediamine, 1,2-propylenediamine, 1,3-propylenediamine, 1,4-butanediamine, neopentanediamine, 1,5-diamino-2-methylpentane, 2-butyl-2-ethyl-1,5-pentanediamine, 1,6-hexamethylenediamine, 2,5-diamino-2,5-dimethylhexane, 2,2,4- and/or 2,4,4-trimethyl-1,6-diaminohexane, 1,8-diaminooctane, 1,11-diaminoundecane, 1,12-diaminododecane, 4-aminomethyl-1,8-octanediamine (triaminononane), diethylenetriamine, triethylenetetramine, 1-amino-3,3,5-trimethyl-5-aminomethyl-cyclohexane, TCD-diamine, 1,4-cyclohexanediamine, 2,4- and/or 2,6-hexahydrotoluoylenediamine, isopropyl-2,4-diaminocyclohexane and/or isopropyl-2,6-diaminocyclohexane, tricyclodecanebis(methylamine), 1,3-bis-(aminomethyl)-cyclohexane, 2,4′- and/or 4,4′-diaminodicyclohexylmethane, 3,3′-dimethyl-4,4′-diaminodicyclohexylmethane, isomeric diaminodicyclohexylmethanes containing a methyl group as a substituent on the nucleus, 3(4)-aminomethyl-1-methylcyclohexyl-amine, 1,3-diaminobenzene, 1,4-diaminobenzene, 2,4- and 2,6-diaminotoluene, 1,3-bis-(aminomethyl)-benzene, 3,5-diethyltoluene-2,4-diamine, m-xylylenediamine, 4,6-dimethyl-1,3-benzenedimethanamine, 4,4′- and/or 2,4′- and/or 2,2′-methylenebisbenzenamine, dimer fatty acid diamines, bis-(3-aminopropyl)-methylamine, 4,9-dioxadodecane-1,12-diamine, 4,7,10-trioxamidecane-1,13-diamine, diamines containing alkoxysilane groups and Michael adducts prepared by reaction of bifunctional primary amines with compounds containing unsaturated groups.

4. A process for preparing a prepolymer of the general formula (II):

X—[—N(CHO)—CO—NH—R 1 —NCO] n   (II)

the process comprising providing a di- or polyisocyanate, providing a formamide-terminated low molecular weight compound, and reacting the di- or polyisocyanate with the formamide-terminated low molecular weight compound; wherein X represents a linear or branched aliphatic, cycloaliphatic, heterocyclic and/or aromatic structural unit having 2 to 20 carbon atoms, which is free of polyether structural units and which is optionally further substituted and/or optionally comprises one or more heteroatoms; wherein R 1 represents an organic radical which may optionally contain one or more heteroatoms and which may further contain one or more additional free isocyanate groups and/or one or more urethane, biuret, carbodiimide, isocyanurate, allophanate, iminooxadiazinedione and/or uretdione structural units; and wherein n≧2.

5. The process according to claim 4 , wherein the process further comprises separating excess di- or polyisocyanate from the prepolymer.

6. The process according to claim 4 , wherein the formamide-terminated low molecular weight compound has the general formula (III):

X—[—NH(CHO)] n   (III)

wherein X and n are as defined, and wherein one mole of the formamide-terminated low molecular weight compound is reacted with n to 10(n) moles of the di- or polyisocyanate.

7. The process according to claim 6 , wherein the process further comprises separating excess di- or polyisocyanate from the prepolymer.

8. A composition comprising a prepolymer according to claim 1 and one or more additional components selected from adhesive, lacquer, and sealant reactants, auxiliaries and additives.

9. A method for preparing a composition selected from the group consisting of adhesives, lacquers, and sealants, the method comprising providing a prepolymer according to claim 1 , and reacting or blending the prepolymer with one or more additional components selected from adhesive, lacquer, and sealant reactants, auxiliaries and additives.

Assignments (3)
CORRECTIVE ASSIGNMENT TO CORRECT THE ASSIGNOR NAME PREVIOUSLY RECORDED ON REEL 038301 FRAME 0001. ASSIGNOR(S) HEREBY CONFIRMS THE CHANGE OF NAME FROM BAYER MATERIALSCIENCE AG TO COVESTRO DEUTSCHLAND AG. Recorded Jun 13, 2016
From: BAYER MATERIALSCIENCE AG
To: COVESTRO DEUTSCHLAND AG
Reel/Frame 038966/0865 →
CHANGE OF NAME Recorded Mar 30, 2016
From: COVESTRO DEUTSCHLAND AG
To: COVESTRO DEUTSCHLAND AG
Reel/Frame 038301/0001 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 16, 2010
From: BLUM, HARALD, DR.; PEIFFER, EVELYN, DR.; LEIMENSTOLL, MARC, DR.
To: BAYER MATERIALSCIENCE AG
Reel/Frame 024694/0924 →