# US 12,000,090 B2 · Treated article, methods of making the treated article, and dispersion for use in making the treated article

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- Number: US 12,000,090 B2
- Document ID: US12000090B2
- Status: Granted
- Kind: B2
- Application number: 17/498,221
- Filed: 2021-10-11
- Published: 2022-06-09
- Granted: 2024-06-04
- Earliest claimed: 2020-12-04
- Assignees: Agc Chemicals Americas, Inc.
- Applicants: Agc Chemicals Americas, Inc.
- Inventors: Tess Duffin Crosetto
- Web page: https://patentgrep.com/patent/US12000090B2

## CPC

- D21H 17/72: {of organic material}
- B05D 7/26: synthetic lacquers or varnishes (B05D7/08, B05D7/16 take precedence)
- D21H 17/14: Carboxylic acids; Derivatives thereof
- D21H 17/34: obtained by reactions only involving carbon-to-carbon unsaturated bonds
- D21H 17/375: {Poly(meth)acrylamide}
- D21H 17/45: Nitrogen-containing groups
- D21H 17/455: {comprising tertiary amine or being at least partially quaternised}
- D21H 17/55: Polyamides; Polyaminoamides; Polyester-amides
- D21H 17/56: Polyamines; Polyimines; Polyester-imides
- D21H 17/60: Waxes
- D21H 19/10: Coatings without pigments (D21H19/66 takes precedence)
- D21H 19/18: comprising waxes
- D21H 19/20: comprising macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- D21H 21/10: Retention agents or drainage improvers
- D21H 21/16: Sizing or water-repelling agents
- D21H: PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- B05D: PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL (conveying articles or workpieces through baths of liquid B65G, e.g. B65G49/02)

## Abstract

A treated article includes fibers, a sizing agent, and a retention aid. The sizing agent includes a wax or a component thereof having an acid value of from 10 mg to 220 mg, KOH/g as measured in accordance with USP 401. The retention aid includes a nitrogen-containing polymer independently selected from the group consisting of (i) a nitrogen-containing polymer of Formula I, (ii) a polyethyleneimine, (iii) a polyaminoamide, (iv) a copolymer formed from the reaction product of epichlorohydrin and dimethylamine, and (v) combinations thereof.

## Claims

### Claim 1

A dispersion for use in a process for making a treated article, the dispersion comprising:
a solvent;
a sizing agent comprising a wax or a component thereof having an acid value of from 10 mg to 220 mg, KOH/g as measured in accordance with USP 401; and
a retention aid comprising a nitrogen-containing polymer of Formula I,
wherein (a), (b), (c), (d), and (e) individually represent the molar percent of each repeating unit included in the nitrogen-containing polymer of Formula I, with each individual molar percent respresented by (a), (b), (c), (d), and (e) ranging from 0 to 100 mol. %, with the sum of (a), (b), (c), (d), and (e) being 100 mol. %,
wherein R0 is independently selected from the group consisting of:
H,
and combinations thereof, and
wherein:
Rz is independently selected from H, —CH3, and combinations thereof,
Rx is independently selected from H, —OH, —COOH, —COOR1, —OCOR1, —R1, —R3OH, —OR1, —NR1R1, —R3NH2, —NH2, —COO(CH2)2N(R1)2, —COO(CH2)2N+(R1)3X−, —COO(CH2)3N+(R1)3X−, and combinations thereof, with the proviso that when Rx is —NH2, Rz is —CH3,
Y is independently selected from H, —OH, —R1, —OR1, —NR1R1, —NH2, and combinations thereof,
Z is independently selected from H, —OH, —C═O, —R1, —OR1, —NR1R1, —NH2 and combinations thereof,
R1 is independently selected from H, a straight chain or branched alkyl or alkenyl containing up to 22 carbons, and combinations thereof,
R2 is independently selected from H, a monosaccharide, an oligosaccharide, polysaccharide moiety, a straight or branched alkyl or alkenyl group up to 22 carbons optionally containing a hydroxyl or aldehyde group, and combinations thereof,
R3 is independently selected from a straight chain or branched alkyl or alkenyl containing up to 22 carbons or combinations thereof,
R4 is independently selected from a straight chain or branched alkyl group containing up to 18 carbons, optionally substituted with a hydroxyl group, and combinations thereof,
R5 is independently selected from H, —OH, —COOH, —COOR1, —OCOR1, —R1, —R1OH, —OR1, —CONH2, —CONHCHOHCHO, —NR1, —NR1R1, —R1NH2, —NH2, and combinations thereof,
A is independently selected from C═O, —CH2, and combinations thereof, and
X− is independently an anion;
wherein the sizing agent is independently selected from a group consisting of a stearate, beeswax, candelilla wax, palmitate, behenate, and combinations thereof.

### Claim 2 (depends on 1)

The dispersion as set forth in claim 1 wherein the retention aid is the nitrogen-containing polymer of Formula I and the combined molar percent of (c) and (d) is less than 5 mol. %.

### Claim 3 (depends on 2)

The dispersion as set forth in claim 2 wherein R0 is independently selected from the group consisting of H,
and combinations thereof.

### Claim 4 (depends on 3)

The dispersion as set forth in claim 3 wherein R0 is independently selected from the group consisting of H,
and combinations thereof.

### Claim 5 (depends on 1)

The dispersion as set forth in claim 1 wherein the retention aid is the nitrogen-containing polymer of Formula I and the combined molar percent of (a), (b), and (e) is 100 mol. % such that the nitrogen-containing polymer is expressed according to Formula II
with each individual molar percent respresented by (a), (b), (c), (d), and (e) ranging from 0 to 100 mol. %, with the sum of (a), (b), (c), (d), and (e) being 100 mol. %.

### Claim 6 (depends on 5)

The dispersion as set forth in claim 5 wherein the retention aid is independently selected from the group consisting of:
i. the nitrogen-containing polymer of Formula II with the combined molar percent of (b) and (e) being 100 mol. %, and R0 is independently selected from the group consisting of H,
and combinations thereof;
ii. the nitrogen-containing polymer of Formula II with the molar percent of (a) being 100 mol. % and Rx is —R3NH2; and
iii. the nitrogen-containing polymer of Formula II with the molar percent of (b) being 100 mol. %, and R0 independently selected from the group consisting of H,
and combinations thereof.

### Claim 7 (depends on 6)

The dispersion as set forth in claim 6 wherein the retention aid is independently selected from the group consisting of:
i. the nitrogen-containing polymer of Formula II as further defined according to Formula IIa:
ii. the nitrogen-containing polymer of Formula II as further defined according to Formula IIb:
and
iii. the nitrogen-containing polymer of Formula II as further defined according to Formula IIc:
wherein the (a), (b1), (b2), (b3), and (e) represent the molar percent of the individual repeating unit;
wherein each of (b1), (b2), and (e) are present in Formula Ila and the sum of (b1), (b2), and (e) is 100 mol. %,;
wherein (a) is 100 mol. % in Formula IIb, and;
wherein each of (b1), (b2), and (b3) are present in Formula IIc and the sum of (b1), (b2), and (b3) is 100 mol. %.

### Claim 8 (depends on 7)

The dispersion as set forth in claim 7 wherein the retention aid is the nitrogen-containing polymer of Formula IIa.

### Claim 9 (depends on 1)

The dispersion as set forth in claim 1 wherein the nitrogen-containing polymer has a charge density of >+0.1 meq/g at a pH of 7.

### Claim 10 (depends on 1)

The dispersion as set forth in claim 1 wherein the sizing agent has an acid value of from 150 to 220, mg KOH/g.

### Claim 11 (depends on 7)

The dispersion as set forth in claim 7 wherein the sizing agent is stearic acid.

### Claim 12 (depends on 1)

The dispersion as set forth in claim 1 wherein the sizing agent is beeswax.

### Claim 13 (depends on 1)

The dispersion as set forth in claim 1 wherein the sizing agent is present in an amount of from 10 to 50 parts by weight and the retention aid is present in an amount of from 0.1 to 12 parts by weight, each based on 100 parts by weight of the dispersion.

### Claim 14 (depends on 1)

The dispersion as set forth in claim 1 further comprising a reaction product of the retention aid and sizing agent.

### Claim 15 (depends on 1)

A fiber slurry comprising:
the dispersion as set forth in claim 1;
fibers; and
a second solvent that is the same as or different than the solvent of the dispersion.

### Claim 16 (depends on 1)

A method of preparing the dispersion as set forth in of claim 1 comprising:
combining the solvent, the sizing agent, and the retention aid.

### Claim 17 (depends on 1)

A method of making a treated article, the method comprising:
forming an article from a fiber slurry, with the article having a top surface and a bottom surface; and
applying the dispersion of claim 1 to at least one surface of the article to form the treated article.

### Claim 18

A dispersion for use in a process of making a treated article, the dispersion comprising:
a solvent;
a sizing agent present in an amount of from 10 to 50 parts by weight based on 100 parts by weight of the dispersion, with the sizing agent comprising a wax or the component thereof independently selected from a group consisting of a stearate, beeswax, candelilla wax, palmitate, behenate, and combinations thereof, with the wax or component thereof having an acid value of from 10 mg to 220 mg, KOH/g as measured in accordance with USP 401; and
a retention aid present in an amount of from 0.1 to 12 parts by weight based on 100 parts by weight of the dispersion, with the retention aid selected from the group consisting of,
i. a nitrogen-containing according to Formula IIa:
ii. a nitrogen-containing polymer according to Formula IIb:
iii. a nitrogen-containing polymer according to Formula IIc:
and
iv. combinations thereof,
wherein the (a), (b1), (b2), (b3), and (e) represent the molar percent of the individual repeating unit;
wherein each of (b1), (b2), and (e) are present in Formula Ila and the sum of (b1), (b2), and (e) is 100 mol. %,;
wherein (a) is 100 mol. % in Formula IIb; and
wherein each of (b1), (b2), and (b3) are present in Formula IIc and the sum of (b1), (b2), and (b3) is 100 mol. %.

### Claim 19

A dispersion for use in a process for making a treated article, the dispersion comprising:
a solvent;
a sizing agent comprising a wax or a component thereof having an acid value of from 10 mg to 220 mg, KOH/g as measured in accordance with USP 401; and
a retention aid comprising a nitrogen-containing polymer of Formula I,
wherein (a), (b), (c), (d), and (e) individually represent the molar percent of each repeating unit included in the nitrogen-containing polymer of Formula I, with each individual molar percent respresented by (a), (b), (c), (d), and (e) ranging from 0 to 100 mol. %, with the sum of (a), (b), (c), (d), and (e) being 100 mol. %,
wherein R0 is independently selected from the group consisting of:
H,
and combinations thereof, and
wherein:
Rz is independently selected from H, —CH3, and combinations thereof,
Rx is independently selected from H, —OH, —COOH, —COOR1, —OCOR1, —R1, —R3OH, —OR1, —NR1R1, —R3NH2, —NH2, —COO(CH2)2N(R1)2, —COO(CH2)2N+(R1)3X−, —COO(CH2)3N+(R1)3X−, and combinations thereof, with the proviso that when Rx is —NH2, Rz is —CH3,
Y is independently selected from H, —OH, —R1, —OR1, —NR1R1, —NH2, and combinations thereof,
Z is independently selected from H, —OH, —C═O, —R1, —OR1, —NR1R1, —NH2 and combinations thereof,
R1 is independently selected from H, a straight chain or branched alkyl or alkenyl containing up to 22 carbons, and combinations thereof,
R2 is independently selected from H, a monosaccharide, an oligosaccharide, polysaccharide moiety, a straight or branched alkyl or alkenyl group up to 22 carbons optionally containing a hydroxyl or aldehyde group, and combinations thereof,
R3 is independently selected from a straight chain or branched alkyl or alkenyl containing up to 22 carbons or combinations thereof,
R4 is independently selected from a straight chain or branched alkyl group containing up to 18 carbons, optionally substituted with a hydroxyl group, and combinations thereof,
R5 is independently selected from H, —OH, —COOH, —COOR1, —OCOR1, —R1, —R1OH, —OR1, —CONH2, —CONHCHOHCHO, —NR1, —NR1R1, —R1NH2, —NH2, and combinations thereof,
A is independently selected from C═O, —CH2, and combinations thereof, and
X− is independently an anion;
wherein the nitrogen-containing polymer has a charge density of >+0.1 meq/g at a pH of 7.

### Claim 20 (depends on 19)

The dispersion as set forth in claim 19 wherein the sizing agent is stearic acid.

### Claim 21 (depends on 19)

A method of preparing the dispersion as set forth in claim 19 comprising: combining the solvent, the sizing agent, and the retention aid.