(Poly)alkylene glycol-containing compound

Patent metadata

Field	Value
Publication number	US-12018121-B2
Application number	US-201917299233-A
Country	US
Kind code	B2
Filing date	Dec 5, 2019
Priority date	Dec 5, 2018
Publication date	Jun 25, 2024
Grant date	Jun 25, 2024

Abstract

The present invention provides a (poly)alkylene glycol-containing compound having higher detergency for composite stains of hydrophilic stains and hydrophobic stains than conventional (poly)alkylene glycol-containing compounds. The present invention relates to a (poly)alkylene glycol-containing compound including: a hydrophobic structural moiety (A); a (poly)alkylene glycol moiety (B); and one lactam ring-containing structural unit (C), in its structure, the hydrophobic structural moiety (A) being present in a proportion of 2.5 to 60% by mass in 100% by mass of the (poly)alkylene glycol-containing compound.

First claim

The invention claimed is:

1. A polyalkylene glycol-containing compound comprising:
a hydrophobic structural moiety (A);
a polyalkylene glycol moiety (B); and
one lactam ring-containing structural unit (C), in its structure,
wherein the polyalkylene glycol-containing compound is represented by the following formula (2):

wherein R 5 is a hydrocarbon group having a carbon number of 4 or greater and optionally containing at least one heteroatom; R 8 is a hydrogen atom or a hydrocarbon group having a carbon number smaller than that of R 5 and optionally containing at least one heteroatom; R 6 is a structure represented by the following formula (4) or (4′);

wherein x is 0, y is 0 or 1, and z is a number of 0 to 5; R 7 s are the same as or different from each other and are each a C2-C20 alkylene group; X 2 is direct bond, an ester group, an ether group, a carbonyl group, a carbonate group, or a group represented by the following formula (10):

wherein Z 1 and Z 2 are each a hydrogen atom or hydroxy group, with one of Z 1 or Z 2 being a hydrogen atom and the other being a hydroxy group; X 3 is a urethane group, an ester group, an ether group, a carbonyl group, a carbonate group, an isocyanate group or an amide group; n2 is a number of 5 to 100; and w2 is a number of 1 to 3,
wherein the at least one heteroatom in each of R 5 and R 8 is a nitrogen atom, a sulfur atom, a phosphorus atom, or a halogen atom,
a proportion of a total mass of R 8 other than a hydrogen atom and R 5 is 2.5 to 60% by mass in 100% by mass of the polyalkylene glycol-containing compound.

2. The polyalkylene glycol-containing compound according to claim 1 ,
wherein the lactam ring is a pyrrolidone ring.

3. The polyalkylene glycol-containing compound according to claim 1 ,
wherein the polyalkylene glycol-containing compound contains the hydrophobic structural moiety (A), the lactam ring-containing structural unit (C), and the polyalkylene glycol moiety (B) in the stated order.

4. The polyalkylene glycol-containing compound according to claim 1 ,
wherein the polyalkylene glycol-containing compound contains the hydrophobic structural moiety (A), the polyalkylene glycol moiety (B), and the lactam ring-containing structural unit (C) in the stated order.

5. The polyalkylene glycol-containing compound according to claim 1 ,
wherein the polyalkylene glycol-containing compound contains hydrophobic groups at an end of a polyalkylene glycol chain and an end other than the end of a polyalkylene glycol chain.

6. The polyalkylene glycol-containing compound according to claim 1 ,
wherein the hydrophobic structural moiety (A) is a structure derived from at least one selected from the group consisting of an acyclic hydrocarbon compound, a cyclic saturated hydrocarbon compound, and an aromatic compound each optionally containing a heteroatom.

7. The polyalkylene glycol-containing compound according to claim 1 ,
wherein R 5 is at least one selected from the group consisting of a C4-C50 aliphatic alkyl group, a C4-C50 alicyclic alkyl group, a C4-C50 alkenyl group, a C4-C50 alkynyl group, and a C6-C50 aryl group each optionally containing a heteroatom.

8. The polyalkylene glycol-containing compound according to claim 1 ,
wherein R 8 is a C1-C3 alkyl group or a hydrogen atom.

9. The polyalkylene glycol-containing compound according to claim 1 ,
wherein n2 is 5 to 80.

10. The polyalkylene glycol-containing compound according to claim 1 ,
wherein the lactam ring containing structural unit (C) is present in a proportion of 1 to 50% by mass in 100% by mass of the polyalkylene glycol-containing compound.

11. The polyalkylene glycol-containing compound according to claim 1 ,
wherein the polyalkylene glycol moiety (B) is present in a proportion of 5 to 95% by mass in 100% by mass of the polyalkylene glycol-containing compound.

12. The polyalkylene glycol-containing compound according to claim 1 ,
wherein the polyalkylene glycol-containing compound has a number average molecular weight of 500 to 100000.

13. A method of producing the polyalkylene glycol-containing compound according to claim 1 , the method comprising any one of the following (i) to (iii):
(i) reacting a compound represented by the following formula (11):

wherein R 13 is a hydrogen atom or a C2-C10 organic group containing a reactive functional group and w3 is a number of 1 to 3,

with a compound represented by the following formula (15);

wherein R 1 is at least one selected from the group consisting of aliphatic alkyl groups having 4 to 50 carbon atoms, cycloaliphatic alkyl groups having 4 to 50 carbon atoms, alkenyl alkynyl groups having 4 to 50 carbon atoms, alkynyl groups having 4 to 50 carbon atoms, and aryl groups having 6 to 50 carbon atoms, which optionally have at least one heteroatom; R 2 s are the same as or different from each other and are each a C2-C20 alkylene group; and X 1′ is a hydrogen atom or a C1-C10 organic group containing a reactive functional group,
wherein the at least one heteroatom in R 1 is a nitrogen atom, a sulfur atom, a phosphorus atom, or a halogen atom; n1 is a number of 5 to 100;
(ii) a first step of reacting a compound represented by the above formula (11) with a compound represented by the following formula (18):
X 3′ —(R 7 O)n2-R 8′   (18)

wherein R 8′ is a hydrogen atom or a hydrocarbon group optionally containing at least one heteroatom and having a carbon number smaller than that of R 5 in the formula (2); R 7 s are the same as or different from each other and are each a C2-C20 alkylene group; X 3′ is a hydrogen atom or a reactive functional group; and n2 are the same as or different from each other and is a number of 5 to 100,
wherein the at least one heteroatom in R 8 is a nitrogen atom, a sulfur atom, a phosphorus atom, or a halogen atom;

and a second step of reacting the resulting reaction product in the first step with a compound represented by the following formula (19):
R 1 —X 2′   (19)

wherein R 1 is at least one selected from the group consisting of aliphatic alkyl groups having 4 to 50 carbon atoms, cycloaliphatic alkyl groups having 4 to 50 carbon atoms, alkenyl groups having 4 to 50 carbon atoms, alkynyl groups having 4 to 50 carbon atoms, and aryl groups having 6 to 50 carbon atoms, which optionally have at least one heteroatom and X 2′ is a reactive functional group,
wherein the at least one heteroatom in R 1 is a nitrogen atom, a sulfur atom, a phosphorus atom, or a halogen atom; and
(iii) a first step of reacting a compound represented by the above formula (19) with a compound represented by the above formula (11) and a second step of reacting the reaction product obtained in the first step with an alkylene oxide.

14. A composition comprising:
the polyalkylene glycol-containing compound according to claim 1 ; and
a different component other than the polyalkylene glycol-containing compound,
the polyalkylene glycol-containing compound being present in a proportion of 1 to 99% by mass in 100% by mass of the com

Assignees

• Nippon Catalytic Chem Ind

Inventors

• Michitaka Daisuke
• KANAO Ryusuke
• Nishikawa Tsuyoshi

Classifications

• C11D1/72

  Ethers of polyoxyalkylene glycols · CPC title

• C08G65/263

  containing heterocyclic amine groups · CPC title

• C08G65/33327

  cyclic · CPC title

• C08G65/2633

  the other compounds containing amide groups · CPC title

• C11D3/3776

  Heterocyclic compounds, e.g. lactam · CPC title