Alkyloxirane derivative, cosmetic material for hair, hydraulic oil composition, resin composition curable by actinic rays, and oil cleansing agent

Patent metadata

Field	Value
Publication number	US-10995178-B2
Application number	US-201716324229-A
Country	US
Kind code	B2
Filing date	Aug 4, 2017
Priority date	Aug 10, 2016
Publication date	May 4, 2021
Grant date	May 4, 2021

Abstract

An alkyloxirane derivative represented by formula (1), wherein M H and M L calculated from a gel permeation chromatogram satisfy formula (2):

Z—[O-(AO) n -H] x   (1)

where Z represents a residual group of a compound having 1 to 22 carbon atoms and one to six hydroxyl groups and wherein all of the hydroxyl groups are excluded from said compound; x is 1 to 6; and AO represents an oxyalkylene group having 3 carbon atoms; and n is 25 or more;

0.35≤M L /M H ≤0.75  (2)

where M H represents a distance between point O and intersecting point P, and M L represents a distance between point Q and intersecting point P determined from the chromatogram.

First claim

The invention claimed is:

1. An alkyloxirane derivative represented by formula (1) below, wherein M H and M L calculated from a chromatogram obtained by gel permeation chromatography measurement of said alkyloxirane derivative satisfy formula (2) below:
Z—[O-(AO) n -H] x   (1)

in the formula (1),
Z represents a residual group of a compound having a carbon number of 1 to 22 and one to six hydroxyl groups wherein all of said hydroxyl groups are excluded from said compound,
x represents a number of 1 to 6,
AO represents an oxyalkylene group having a carbon number of 3 and
n represents a number of 25 or more;
0.35≤M L /M H ≤0.75  (2)

provided that L is assigned to a length of a perpendicular line from the maximum point K at which an intensity of a refractive index on said chromatogram takes the maximum value to a base line B,
provided that points O and Q are assigned to two points at which said intensity of said refractive index on said chromatogram is L/2, said point O has a shorter elution time and said point Q has a longer elution time, and
provided that P is assigned to an intersecting point where a straight line G connecting said point O and point Q intersects said perpendicular line from said maximum point K to said base line,
M H represents a distance between said point O and said intersecting point P, and
M L represents a distance between said point Q and said intersecting point P,
wherein the alkyloxirane derivative is produced by ring-opening addition polymerization of methyloxirane, wherein the average supply rates of methyloxirane to the reaction mixture are controlled as follows:
V 1 /V 2 =1.1 to 2.0
V 2 /V 3 =1.1 to 1.5

where V 1 represents a rate (supply amount per an unit time) when between 5 to 20 wt % of a total supply amount of methyloxirane is supplied,
V 2 represents a rate when between 20 to 50 wt % of a total supply amount of methyloxirane is supplied, and
V 3 represents a rate when between 50 to 100 wt % of a total supply amount of methyloxirane is supplied.

2. The alkyloxirane derivative of claim 1 , wherein As calculated from said chromatogram satisfies the following formulas (3) and (4):
As=W 1/2 /W 5% z  (3)

0.30≤As≤0.70  (4)

provided that points S and R are assigned to two points at which said intensity of said refractive index on said chromatogram is L/20, said point R has a shorter elution time and said point S has a longer elution time, and
provided that T is assigned to an intersecting point where a straight line H connecting said point R and point S intersects said perpendicular line from said maximum point K to said base line B,
W 1/2 is assigned to a distance between said point R and said intersecting point T, and W 5% is assigned to a distance between said point R and said point S.

3. The alkyloxirane derivative of claim 1 , wherein said alkyloxirane derivative is represented by the following formula (5):
R 1 O-(AO) n -H  (5)

R 1 represents a hydrocarbon group having a carbon number of 1 to 22;
AO represents said oxyalkylene group having a carbon number of 3: and
n represents said number of 25 or more.

4. A hair cosmetic composition comprising said alkyloxirane derivative of claim 1 .

5. A hydraulic oil composition comprising:
an ester compound (A) as follows; and
said alkyloxirane derivative (B) of claim 1 ,
wherein 1.0 to 30.0 mass parts of said alkyloxirane derivative (B) is contained with respect to 100 mass parts of said ester compound (A):
(A) said ester compound of neopentyl polyol having a carbon number of 5 to 10 and an alcohol valence of 3 to 6 and of a fatty acid having a carbon number of 6 to 22.

6. An active energy ray-curable resin composition comprising the following component (A) and component (B), wherein a ratio of a mass of said component (A) with respect to a mass of said component (B) ((A)/(B)) is 1/99 to 30/70,
said component (A):
an urethane compound of a reaction product of said alkyloxirane compound (a1) of claim 1 and of an isocyanate (a2) comprising two or more isocyanate groups in a molecule of said isocyanate;
said component (B):
an urethane (meth)acrylate compound having two or more ethylenically unsaturated groups.

7. An oil cleansing agent comprising:
1 to 20 mass % of a component (a) below;
45 to 90 mass % of a component (b) below; and
5 to 50 mass % of a component (c) below:
(a) said alkyloxirane compound of claim 2 ;
(b) a liquid oily component; and
(c) a surfactant of an ester of a polyvalent alcohol and a fatty acid.

Assignees

• Nof Corp

Inventors

• Hara Yusuke
• Wakita Kazuaki
• Kusumoto Mitsushi
• Nagayama Megumi
• Monjiyama Shunsuke
• Yamanaka Aiko
• Kawamoto Hideki

Classifications

• C08G65/2663 Primary

  Metal cyanide catalysts, i.e. DMC's · CPC title

• A61Q19/10

  Washing or bathing preparations · CPC title

• C08F290/067

  Polyurethanes; Polyureas · CPC title

• C10M145/36

  etherified · CPC title

• C10M105/38

  of polyhydroxy compounds · CPC title