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US 2011/0253309 A1Published application
Aldimine and composition containing aldimine
AssigneeSika Technology AG
InventorUrs BURCKHARDT
Life of this patent
Estimating the term…
Abstract
Aldimines of Formula (I), which can be used as latent curing agents in curing compositions, for example, in moisture-curing polyurethane compositions that have isocyanate groups. The aldimines are compounds that can be liquid at room temperature, can have a hardly noticeable aldehyde odor before, during and after hydrolysis, and can have a long shelf life. An aldehyde in polyurethane compositions that is released during hydrolysis has only a slight softening effect and can exhibit very little tendency to migrate or exude.
Claims24
An aldimine of Formula (I)
- wherein
- Y represents O or S;
- A either
- represents the (n+m)-value radical of an amine after removal of n primary amino groups and m HX groups,
- or together with R7 represents an (n+2*m)-value hydrocarbon radical with 3 to 20 C atoms, which optionally contains at least one heteroatom;
- R1 and R2 either
- independently of one another in each case represents a monovalent hydrocarbon radical with 1 to 12 C atoms,
- or together represent a divalent hydrocarbon radical with 4 to 12 C atoms, which is part of an optionally substituted, carbocyclic ring with 5 to 8 C atoms;
- R3 stands for a hydrogen atom or an alkyl, cycloalkyl, arylalkyl or alkoxycarbonyl radical with 1 to 12 C atoms;
- R4 and R5 either
- together represent a divalent radical with 2 to 10 C atoms that optionally has oxygen or sulfur atoms and that is part of an optionally substituted, 5- or 6- or 7-membered ring,
- or
- R4 represents an alkyl, cycloalkyl, arylalkyl or acyl radical with 1 to 10 C atoms, and
- R5 represents a hydrogen atom or for a monovalent radical with 1 to 20 C atoms selected from the group consisting of an alkyl, cycloalkyl, arylalkyl, aryl radical, —OR5′, —SR5′ and —NR5′R5″,
- wherein R5′ and R5″ either in each case represents a hydrocarbon radical or together represent an alkylene radical, which is part of a 5-, 6- or 7-membered ring;
- X represents O or S or N—R6 or N—R7,
- wherein R6
- either
- represents a monovalent hydrocarbon radical with 1 to 20 C atoms, which has optionally at least one carboxylic acid ester, nitrile, nitro, phosphonic acid ester, sulfone or sulfonic acid ester group,
- or represents a substituent of Formula (II),
- wherein
- p stands for 0 or for an integer from 1 to 10,000, and
- B stands for a (p+1)-value hydrocarbon radical, which optionally contains ether-oxygen, tertiary amine-nitrogen, hydroxyl groups, secondary amino groups or mercapto groups;
- and
- R7 together with A stands for an (n+2*m)-value hydrocarbon radical with 3 to 20 C atoms, which optionally contains at least one heteroatom;
- n stands for 1 or 2 or 3 or 4, and
- m stands for 0 or 1 or 2 or 3 or 4,
- provided that m+n stands for 2 or 3 or 4 or 5.
25 more elements
A single-component, moisture-curing composition, comprising
- a) at least one polyisocyanate P, and
- b) at least one aldimine of Formula (I b)
- wherein
- t represents 2 or 3;
- A2 represents a radical of an amine B2 after removal of t primary amino groups, provided that the aldimine of Formula (I b) does not have any active hydrogen,
- Y represents O or S;
- R1 and R2 either
- independently of one another in each case represents a monovalent hydrocarbon radical with 1 to 12 C atoms,
- or together represent a divalent hydrocarbon radical with 4 to 12 C atoms, which is part of an optionally substituted, carbocyclic ring with 5 to 8 C atoms;
- R3 stands for a hydrogen atom or an alkyl, cycloalkyl, arylalkyl or alkoxycarbonyl radical with 1 to 12 C atoms;
- R4 and R5 either
- together represent a divalent radical with 2 to 10 C atoms that optionally has oxygen or sulfur atoms and that is part of an optionally substituted, 5- or 6- or 7-membered ring,
- or
- R4 represents an alkyl, cycloalkyl, arylalkyl or acyl radical with 1 to 10 C atoms, and
- R5 represents a hydrogen atom or for a monovalent radical with 1 to 20 C atoms selected from the group consisting of an alkyl, cycloalkyl, arylalkyl, aryl radical, —OR5′, —SR5′ and —NR5′R5″,
- wherein R5′ and R5″ either in each case represents a hydrocarbon radical or together represent an alkylene radical, which is part of a 5-, 6- or 7-membered ring;
- and/or at least one addition product AV of Formula (XII)
- wherein Q represents a radical of a (u+v) polyisocyanate P that has isocyanate groups after removal of all isocyanate groups;
- u represents 0 or 1 or 2 or 3,
- v represents 1 or 2 or 3 or 4,
- provided that (u+v) represents 2 or 3 or 4,
- A1 either
- represents a divalent hydrocarbon radical with 2 to 20 C atoms, which optionally contains at least one heteroatom,
- or
- together with R9 represents a trivalent hydrocarbon radical with 3 to 20 C atoms, which optionally contains at least one heteroatom,
- X1 represents O or S or N—R8 or N—R9,
- wherein R8
- either
- represents a monovalent hydrocarbon radical with 1 to 20 C atoms, which optionally has at least one carboxylic acid ester, nitrile, nitro, phosphonic acid ester, sulfone or sulfonic acid ester group,
- or represents a substituent of Formula (II a),
- wherein B1 stands for a divalent hydrocarbon radical with 2 to 12 C atoms that optionally has ether-oxygen or tertiary amine-nitrogen;
- and
- R9 together with A1 represents a trivalent hydrocarbon radical with 3 to 20 C atoms, which optionally contains at least one heteroatom;
- provided that A1 does not have any active hydrogen
- Y represents O or S;
- R1 and R2 either
- independently of one another in each case represents a monovalent hydrocarbon radical with 1 to 12 C atoms,
- or together represent a divalent hydrocarbon radical with 4 to 12 C atoms, which is part of an optionally substituted, carbocyclic ring with 5 to 8 C atoms;
- R3 stands for a hydrogen atom or an alkyl, cycloalkyl, arylalkyl or alkoxycarbonyl radical with 1 to 12 C atoms;
- R4 and R5 either
- together represent a divalent radical with 2 to 10 C atoms that optionally has oxygen or sulfur atoms and that is part of an optionally substituted, 5- or 6- or 7-membered ring,
- or
- R4 represents an alkyl, cycloalkyl, arylalkyl or acyl radical with 1 to 10 C atoms, and
- R5 represents a hydrogen atom or for a monovalent radical with 1 to 20 C atoms selected from the group consisting of an alkyl, cycloalkyl, arylalkyl, aryl radical, —OR5′, —SR5′ and —NR5′R5″,
- wherein R5′ and R5″ either in each case represents a hydrocarbon radical or together represent an alkylene radical, which is part of a 5-, 6- or 7-membered ring.
42 more elements
Dependencies are inferred from the claim text.