Modified polyallylamine and process for producing the same
AssigneeNitto Boseki Co., Ltd.
InventorsMitsumasa Hashimoto, Minoru Takeuchi, Shuichi Kataoka, Kiyohiko Takemoto
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Abstract
The present invention relates to a polyallylamine-based high-molecular-weight polymer which is easily soluble in water and in an organic solvent and gives an excellently stable aqueous solution or organic solvent solution thereof which is suitable for use in the fields of fine chemicals such as the field of inkjet recording, and the polymer is a modified polyallylamine obtained by modifying a copolymer of N,N-dialkylallylamine and allylamine.
Claims10
A modified polyallylamine comprising, as an essential component, a unit of the general formula (M-1),
- wherein each of R1 and R2 is independently an alkyl group having 1 to 4 carbon atoms,
- comprising at least one unit selected from units of the formula (M-2),
- the general formula (M-3),
- wherein R3 is an alkyl group having 1 to 12 carbon atoms or an aryl group having 6 to 12 carbon atoms,
- the general formula (M-4),
- wherein R4 is an alkyl group having 1 to 12 carbon atoms,
- the general formula (M-5),
- wherein R5 is a hydrogen atom or methyl and A is —CONR6R7, —CN or —COOR8, in which each of R6 and R7 is independently a hydrogen atom or an alkyl group having 1 to 8 carbon atoms and optionally containing a hydroxyl group, a keto group, a mono(C1-C4 alkyl) amino group, a di(C1-C4 alkyl) amino group or a tri(C1-C4 alkyl) ammonium group, and R6 and R7 may bond to each other and form a piperidino or morpholino group together with a nitrogen atom, and R8 is an alkyl group having 1 to 8 carbon atoms and optionally containing a hydroxyl group, a keto group, a mono(C1-C4 alkyl) amino group, a di(C1-C4 alkyl) amino group or a tri(C1-C4 alkyl) ammonium group,
- the general formula (M-6),
- wherein R5 and A are as defined above,
- the general formula (M-7),
- wherein B is an alkyl group having 1 to 8 carbon atoms and optionally containing a hydroxyl group, an alkoxyl or alkenyloxy group having 1 to 4 carbon atoms,
- and the general formula (M-8),
- wherein B is as defined as said B,
- and optionally containing a unit of the formula (M-9),
A modified polyallylamine having a structure of the general formula (I),
- wherein each of R1 and R2 is independently an alkyl group having 1 to 4 carbon atoms, X is —CONH2, —COOR3, in which R3 is an alkyl group having 1 to 12 carbon atoms or an aryl group having 6 to 12 carbon atoms, or —COR4, in which R4 is an alkyl group having 1 to 12 carbon atoms, each of p and q is independently an integer of 1 or more, and r is 0 or an integer of 1 or more.
A modified polyallylamine having a structure of the general formula (II),
- wherein each of R1 and R2 is independently an alkyl group having 1 to 4 carbon atoms, Y is —CH2CH(R5)—A, in which R5 is a hydrogen atom or methyl and A is —CONR6R7, —CN or —COOR8, in which each of R6 and R7 is independently a hydrogen atom or an alkyl group having 1 to 8 carbon atoms and optionally containing a hydroxyl group, a keto group, a mono(C1-C4 alkyl) amino group, a di(C1-C4 alkyl) amino group or a tri(C1-C4 alkyl) ammonium group, R6 and R7 may bond to each other to form a piperidino or morpholino group together with a nitrogen atom, and R8 is an alkyl group having 1 to 8 carbon atoms and optionally containing a hydroxyl group, a keto group, a mono(C1-C4 alkyl) amino group, a di(C1-C4 alkyl) amino group or a tri(C1-C4 alkyl group) ammonium group, or —CH2CH(OH)—B, in which B is an alkyl group having 1 to 8 carbon atoms and optionally containing a hydroxyl group or an alkoxyl or alkenyloxy group having 1 to 4 carbon atoms, p is an integer of 1 or more, and each of t, u and v is independently 0 or an integer of 1 or more, provided that at least one of t and u is an integer of 1 or more.
A process for producing a modified polyallylamine of the general formula (I-1), which comprises reacting a cyanic acid with a copolymer of N,N-dialkylallylamine and an allylamine, represented by the general formula (III),
- wherein each of R1 and R2 is independently an alkyl group having 1 to 4 carbon atoms and each of p and w is independently an integer of 1 or more,
- to produce the modified polyallylamine of the general formula (I-1),
- wherein q is an integer of 1 or more, r is 0 or an integer of 1 or more and R1, R2 and p are as defined above.
A process for producing a modified polyallylamine of the general formula (I-2), which comprises reacting an alkoxycarbonylation agent having 1 to 12 carbon atoms or an aryloxycarbonylation agent having 6 to 12 carbon atoms with a copolymer of N,N-dialkylallylamine and an allylamine, represented by the general formula (III),
- wherein each of R1 and R2 is independently an alkyl group having 1 to 4 carbon atoms and each of p and w is independently an integer of 1 or more,
- to produce the modified polyallylamine of the general formula (I-2),
- wherein R3 is an alkyl group having 1 to 12 carbon atoms or an aryl group having 6 to 12 carbon atoms, q is an integer of 1 or more, r is 0 or an integer of 1 or more, and R1, R2 and p are as defined above.
A process for producing a modified polyallylamine of the general formula (I-3), which comprises reacting an acylation agent having 1 to 12 carbon atoms with a copolymer of N,N-dialkylallylamine and an allylamine, represented by the general formula (III),
- wherein each of R1 and R2 is independently an alkyl group having 1 to 4 carbon atoms and each of p and w is independently an integer of 1 or more,
- to produce the modified polyallylamine of the general formula (I-3),
- wherein R4 is an alkyl group having 1 to 12 carbon atoms, q is an integer of 1 or more, r is 0 or an integer of 1 or more, and R1, R2 and p are as defined above.
A process for producing a modified polyallylamine of the general formula (II-1), which comprises reacting an acryl compound of the general formula (V),
- CH2═C(R6)—A (V)
- wherein R5 is a hydrogen atom or methyl and A is —CONR6R7, —CN or —COOR8, in which each of R6 and R7 is independently a hydrogen atom or an alkyl group having 1 to 8 carbon atoms and optionally containing a hydroxyl group, a keto group, a mono(C1-C4 alkyl) amino group, a di(C1-C4 alkyl) amino group or a tri(C1-C4 alkyl) ammonium group and R6 and R7 may bond to each other and form a piperidino or morpholino group together with a nitrogen atom, and R8 is an alkyl group having 1 to 8 carbon atoms and optionally containing a hydroxyl group, a keto group, a mono(C1-C4 alkyl) amino group, a di(C1-C4 alkyl) amino group or a tri(C1-C4 alkyl) ammonium group, with a copolymer of N,N-dialkylallylamine and an allylamine, represented by the general formula (III),
- wherein each of R1 and R2 is independently an alkyl group having 1 to 4 carbon atoms and each of p and w is independently an integer of 1 or more, to produce the modified polyallylamine of the general formula (II-1),
- wherein Y1 is a —CH2CH(R5)—A, each of t, u and v is independently 0 or an integer of 1 or more, provided that at least one of t and u is an integer of 1 or more, and R1, R2, R5, A and p are as defined above.
A process for producing a modified polyallylamine of the general formula (II-2), which comprises reacting an epoxy compound of the general formula (VI),
- wherein B is an alkyl group having 1 to 8 carbon atoms and optionally containing a hydroxyl group, an alkoxyl or alkenyloxy group having 1 to 4 carbon atoms, with a copolymer of N,N-dialkylallylamine and an allylamine, represented by the general formula (III),
- wherein each of R1 and R2 is independently an alkyl group having 1 to 4 carbon atoms and each of p and w is independently an integer of 1 or more,
- to produce the modified polyallylamine of the general formula (II-2),
- wherein Y2 is a CH2CH(OH)—B, each of t, u and v is independently an integer of 1 or more, provided that at least one of t and u is an integer of 1 or more, and R1, R2, B and p are as defined above.
Dependencies are inferred from the claim text.