# US 10,119,918 B2 · Adjustable Colorimetric Moisture Indicators

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- Number: US 10,119,918 B2
- Document ID: US10119918B2
- Status: Granted
- Kind: B2
- Application number: 14/441,478
- Filed: 2013-11-14
- Published: 2015-10-15
- Granted: 2018-11-06
- Earliest claimed: 2012-11-14
- Assignees: 3M Innovative Properties Company
- Applicants: 3M Innovative Properties Company
- Inventors: Myungchan Kang; Evan Koon Lun Yuuji Hajime
- Web page: https://patentgrep.com/patent/US10119918B2

## CPC

- G01N 21/81: Indicating humidity
- B01J 20/08: comprising aluminium oxide or hydroxide; comprising bauxite
- B01J 20/103: {comprising silica}
- B01J 20/223: {containing metals, e.g. organo-metallic compounds, coordination complexes}
- B01J 20/28016: {Particle form}
- B01J 20/28057: {Surface area, e.g. B.E.T specific surface area}
- B01J 20/3204: {Inorganic carriers, supports or substrates}
- B01J 20/3236: {containing metal, other than zeolites, e.g. oxides, hydroxides, sulphides or salts}
- B01J 20/3248: {the functional group or the linking, spacer or anchoring group as a whole comprising at least one type of heteroatom selected from a nitrogen, oxygen or sulfur, these atoms not being part of the carrier as such}
- G01N 31/222: {for investigating moisture content}
- B01J 2220/49: Materials comprising an indicator, e.g. colour indicator, pH-indicator
- G01N 2021/7793: {Sensor comprising plural indicators}
- G01N: INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES (measuring or testing apparatus or processes other than immunoassay, involving enzymes or microorganisms C12M, C12Q)
- B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS

## Abstract

Compositions are provided comprising: 1) a solid metal oxide support having surface hydroxyl groups; 2) a silyl-containing compound bound to the solid metal oxide support through a silanol bond with the surface hydroxyl groups; and 3) a bis(glyoxime)-transition metal complex bound to the solid metal oxide support. These compositions can be used to make a colorimetric relative humidity-indicating sensor. A method of adjusting the colorimetric response of a moisture-indicating composition and a method of detecting moisture are also provided.

## Claims

### Claim 1

A composition comprising:
a solid metal oxide support having surface hydroxyl groups;
a silyl-containing compound bound to the solid metal oxide support through a silanol bond with the surface hydroxyl groups; and
a bis(glyoxime)-transition metal complex bound to the solid metal oxide support;
wherein the composition is a reversible colorimetric moisture-indicating composition.

### Claim 2 (depends on 1)

The composition of claim 1, wherein the silyl-containing compound is of Formula (I)
R1—Si(R2)3-x(R3)x (I)
wherein
R1 is an alkyl, fluoroalkyl, alkyl substituted with an amino, aryl, aralkyl, or alkaryl group;
each R2 is independently hydroxyl or a hydrolyzable group;
each R3 is independently a non-hydrolyzable group; and
x is an integer equal to 0, 1, or 2.

### Claim 3 (depends on 1)

The composition of claim 1, wherein the silyl-containing compound is of Formula (II)
(R3)x(R2)3-xSi—R4—Si(R2)3-x(R3)x (II)
wherein
R4 is an alkylene, arylene, or a combination thereof;
each R2 is independently hydroxyl or a hydrolyzable group;
each R3 is independently a non-hydrolyzable group; and
x is an integer equal to 0, 1, or 2.

### Claim 4 (depends on 1)

The composition of claim 1, wherein the silyl-containing compound is selected from the group consisting of diethoxydimethylsilane, hexamethyldisilazane, n-octadecyltrichlorosilane, 1H,1H,2H,2H-perfluoroctyldimethylchlorosilane, and (3-aminopropyl)triethoxysilane.

### Claim 5 (depends on 1)

The composition of claim 1, wherein no more than about 50% of surface hydroxyl groups of the support are bound to the silyl-containing compound.

### Claim 6 (depends on 1)

The composition of claim 1, wherein the solid metal oxide support comprises an oxide of aluminum, silicon, or a combination thereof.

### Claim 7 (depends on 1)

The composition of claim 1, wherein the transition metal in the bis(glyoxime)-transition metal complex comprises rhodium, iridium, platinum, palladium, gold, nickel, copper, or a combination thereof.

### Claim 8 (depends on 1)

The composition of claim 1, wherein the bis(glyoxime)-transition metal complex comprises bis(dimethylglyoximato)-nickel(II).

### Claim 9 (depends on 1)

The composition of claim 1, wherein the composition quantitatively changes optical spectrum at relative humidities ranging from about 50% to about 90% relative humidity at 25° C.

### Claim 10

A colorimetric relative humidity-indicating sensor comprising:
a reversible colorimetric moisture-indicating composition comprising
a solid metal oxide support having surface hydroxyl groups;
a silyl-containing compound bound to the solid metal oxide support through a silanol bond with the surface hydroxyl groups; and
a bis(glyoxime)-transition metal complex bound to the solid metal oxide support; and
wherein the optical spectrum of the sensor changes quantitatively according to the relative humidity within the environment within which the sensor is placed.

### Claim 11 (depends on 10)

The sensor of claim 10, wherein the silyl-containing compound is of Formula (I)
R1—Si(R2)3-x(R3)x (I)
wherein
R1 is an alkyl, fluoroalkyl, alkyl substituted with an amino, aryl, aralkyl, or alkaryl group;
each R2 is independently hydroxyl or a hydrolyzable group;
each R3 is independently a non-hydrolyzable group; and
x is an integer equal to 0, 1, or 2.

### Claim 12 (depends on 10)

The sensor of claim 10, wherein the silyl-containing compound is of Formula (II)
(R3)x(R2)3-xSi—R4—Si(R2)3-x(R3)x (II)
wherein
R4 is an alkylene, arylene, or a combination thereof;
each R2 is independently hydroxyl or a hydrolyzable group;
each R3 is independently a non-hydrolyzable group; and
x is an integer equal to 0, 1, or 2.

### Claim 13 (depends on 10)

The sensor of claim 10, wherein no more than about 50% of surface hydroxyl groups of the support are bound to the silyl-containing compound.

### Claim 14 (depends on 10)

The sensor of claim 10, wherein the solid metal oxide support comprises an oxide of aluminum, silicon, or a combination thereof.

### Claim 15 (depends on 10)

The sensor of claim 10, wherein the bis(glyoxime)-transition metal complex comprises bis(dimethylglyoximato)-nickel (II).

### Claim 16 (depends on 10)

The sensor of claim 10, wherein the sensor quantitatively changes optical spectrum at relative humidities ranging from about 50% to about 90% relative humidity at 25° C.

### Claim 17 (depends on 10)

The sensor of claim 10, wherein the sensor quantitatively changes optical spectrum at relative humidities ranging from about 60% to about 80% relative humidity at 25° C.

### Claim 18

A method of adjusting the colorimetric response of a moisture-indicating composition comprising:
modifying the surface of a solid metal oxide support having surface hydroxyl groups by reacting the surface hydroxyl groups of the solid metal oxide support with a silyl-containing compound to create a modified solid metal oxide support; and
bonding a bis(glyoxime)-transition metal complex to the modified solid metal oxide support to create a reversible colorimetric moisture-indicating composition.

### Claim 19 (depends on 18)

The method of claim 18, wherein the silyl-containing compound is of Formula (I)
R1—Si(R2)3-x(R3)x (I)
wherein
R1 is an alkyl, fluoroalkyl, alkyl substituted with an amino, aryl, aralkyl, or alkaryl group;
each R2 is independently hydroxyl or a hydrolyzable group;
each R3 is independently a non-hydrolyzable group; and
x is an integer equal to 0, 1, or 2.

### Claim 20 (depends on 18)

The method of claim 18, wherein the silyl-containing compound is of Formula (II)
(R3)x(R2)3-xSi—R4—Si(R2)3-x(R3)x (II)
wherein
R4 is an alkylene, arylene, or a combination thereof;
each R2 is independently hydroxyl or a hydrolyzable group;
each R3 is independently a non-hydrolyzable group; and
x is an integer equal to 0, 1, or 2.

### Claim 21 (depends on 18)

The method of claim 18, wherein no more than about 50% of surface hydroxyl groups of the support are bound to the silyl-containing compound.

### Claim 22 (depends on 18)

The method of claim 18, wherein the solid metal oxide support comprises an oxide of aluminum, silicon, or a combination thereof.

### Claim 23 (depends on 18)

The method of claim 18, wherein the bis(glyoxime)-transition metal complex comprises bis(dimethylglyoximato)-nickel (II).

### Claim 24 (depends on 18)

The method of claim 18, wherein the moisture-indicating composition quantitatively changes optical spectrum at relative humidities ranging from about 50% to about 90% relative humidity at 25° C.

### Claim 25 (depends on 18)

The method of claim 18, wherein the moisture-indicating composition quantitatively changes optical spectrum at relative humidities ranging from about 60% to about 80% relative humidity at 25° C.