Process for the preparation of high-solids, low-viscosity latex using selective hydrophilic macro-raft agents

Patent metadata

Field	Value
Publication number	US-12252560-B2
Application number	US-202017603211-A
Country	US
Kind code	B2
Filing date	Apr 14, 2020
Priority date	Apr 16, 2019
Publication date	Mar 18, 2025
Grant date	Mar 18, 2025

Abstract

Processes to prepare aqueous polymer dispersions are provided, as well as compositions thereof, which have high solids content (e.g., 50%) with low viscosity. The process uses a selective hydrophilic macro-RAFT agent of formula (I), and is substantially free of surfactants. This process can be used to make latex polymers with good stability, which can be used widely in coatings (e.g., architectural paints, stone paints, industrial coatings, wood coatings, etc.), adhesives, sealants and mastic compositions.

First claim

What is claimed is:

1. A process for preparing an aqueous polymer dispersion, comprising:
a. providing an initial composition comprising:
i. about 0.5 to about 6 parts of a selective hydrophilic macro-RAFT agent of formula (I); and
ii. about 0.1 to about 30 parts of at least one first monomer;
iii. about 0.05 to about 0.5 parts of a free radical initiator; and
iv. water,

b. reacting the initial composition from step (a) under suitable conditions to generate a seed composition, wherein the seed composition comprises a polymer formed from the selective hydrophilic macro-RAFT agent of formula (I) and the at least one first monomer; and
c. combining the seed composition from step (b) with:
i. about 0.05 to about 0.8 parts of at least one initiator; and
ii. about 0.1 to about 99 parts of at least one second monomer, under conditions suitable for reacting the seed composition with the at least one second monomer to form the aqueous polymer dispersion;

wherein the at least one first monomer and at least one second monomer are different, wherein the first monomer comprises styrene monomers, acrylic monomers, vinyl ester monomers, or mixtures thereof,
wherein the at least one second monomer comprises styrene monomers, acrylic monomers, vinyl ester monomers, or mixtures thereof;
wherein the process is substantially free of surfactants; and
wherein the selective hydrophilic macro-RAFT agent of formula (I) is defined as follows:
(R 11 ) x -Z 11 —C(═S)—Z 12 -[A]-R 12   (I)

wherein:
Z 11 represents C, N, O, S or P,
Z 12 represents S or P,
R 11 and R 12 , which may be identical or different, represent:
an optionally substituted alkyl, acyl, aryl, alkene or alkyne group (i), or
a saturated or unsaturated, optionally substituted or aromatic carbon-based ring (ii), or
a saturated or unsaturated, optionally substituted heterocycle (iii), these groups and rings (i), (ii) and (iii) may be optionally substituted with substituted phenyl groups, substituted aromatic groups or groups: alkoxycarbonyl or aryloxycarbonyl (—COOR), carboxyl (—COOH), acyloxy (—O 2 CR), carbamoyl (—CONR 2 ), cyano (—CN), alkylcarbonyl, alkylarylcarbonyl, arylcarbonyl, arylalkylcarbonyl, phthalimido, maleimido, succinimido, amidino, guanidino, hydroxyl (—OH), amino (—NR 2 ), halogen, allyl, epoxy, alkoxy (—OR), S-alkyl, S-aryl, groups of hydrophilic or ionic nature selected from the group of alkali metal salts of carboxylic acids, alkali metal salts of sulphonic acid, polyalkylene oxide (PEO or PPO) chains and cationic substituents (quaternary ammonium salts),

R represents an alkyl or aryl group,
x corresponds to the valency of Z 11 , or alternatively x is 0, in which case Z 11 represents a phenyl, alkene or alkyne radical, optionally substituted with an optionally substituted alkyl; acyl; aryl; alkene or alkyne group; an optionally substituted, saturated, unsaturated, or aromatic, carbon-based ring; an optionally substituted, saturated or unsaturated heterocycle; alkoxycarbonyl or aryloxycarbonyl (—COOR); carboxyl (COOH); acyloxy (—O 2 CR); carbamoyl (—CONR 2 ); cyano (—CN); alkylcarbonyl; alkylarylcarbonyl; arylcarbonyl; arylalkylcarbonyl; phthalimido; maleimido; succinimido; amidino; guanidino; hydroxyl (—OH); amino (—NR 2 ); halogen; allyl; epoxy; alkoxy (—OR), S-alkyl; S-aryl groups; groups of hydrophilic or ionic nature selected from the group of alkali metal salts of carboxylic acids, alkali metal salts of sulphonic acid, polyalkylene oxide (PEO or PPO) chains and cationic substituents (quaternary ammonium salts); and
A represents a monoblock, diblock or triblock polymer comprising at least a first block which is hydrophilic in nature and an optional second block which is hydrophobic or hydrophilic in nature.

2. The process according to claim 1 , further wherein the aqueous polymer dispersion is formed using polymerization induced self-assembly of a latex polymer composition.

3. The process according to claim 1 , wherein a latex polymer composition formed in step (c) has a solids content of at least 40%, and a viscosity of less than 4000 cps, wherein the viscosity is determined using a Brookfield Model LVT viscometer at 30 rpm and No. 3 spindle.

4. The process according to claim 1 , wherein the selective hydrophilic macro-RAFT agent is present in an amount of about 0.5 to about 3 parts.

5. The process according to claim 1 , wherein the selective hydrophilic macro-RAFT agent of formula (I) is selected from the group consisting of PAA-Xa, PAM-Xa, PAM-PAA-Xa, and PDMA-Xa.

6. A composition comprising a latex polymer composition made according to the process of claim 1 , wherein the composition is obtained by a free-radical emulsion polymerization process.

7. A composition comprising a latex polymer composition made according to the process of claim 1 , wherein the composition is a coating composition, paint composition, industrial coating, adhesive composition, mastic composition, sealant composition, or wood coating.

8. The composition of claim 6 , comprising a scrub resistance that is at least about five times more than a surfactant-based latex.

9. The composition of claim 6 , comprising adhesion to glass, metal, and combinations thereof.

10. The process according to claim 1 , wherein the at least one first monomer comprises methyl methacrylate/butyl acrylate in a ratio of about 40:60 to about 60:40 .

11. The process according to claim 1 , wherein the at least one first monomer is selected from a butyl acrylate/methyl methacrylate copolymer.

12. The composition according to claim 6 , wherein the seed composition consisting consists of a butyl acrylate/methyl methacrylate copolymer.

13. A process for preparing an aqueous polymer dispersion, comprising:
a. providing an initial composition comprising:
i. about 0.5 to about 6 parts of a selective hydrophilic macro-RAFT agent of formula (I); and
ii. about 0.1 to about 30 parts of at least one first monomer;
iii. about 0.05 to about 0.5 parts of a free radical initiator; and
iv. water,

b. reacting the initial composition from step (a) under suitable conditions to generate a seed composition, wherein the seed composition comprises a polymer formed from the selective hydrophilic macro-RAFT agent of formula (I) and the at least one first monomer; and
c. combining the seed composition from step (b) with:
i. about 0.05 to about 0.8 parts of at least one initiator; and
ii. about 0.1 to about 99 parts of at least one second monomer,

under conditions suitable for reacting the seed composition with the at least one second monomer to form the aqueous polymer dispersion;
wherein the at least one first monomer and at least one second monomer are different, wherein the at least one first monomer is selected from the group consisting of styrene monomers, acrylic monomers, and mixtures thereof;
wherein the at least one second monomer is selected from the group consisting of styrene monomers, acrylic monomers, and mixtures thereof;
wherein the selective hydrophilic macro-RAFT agent of formula (I) is defined as follows:
(R 11 ) x -Z 11 —C(═S)—Z 12 -[A]-R 12   (I)

wherein:
Z 11 represents C, N, O, S or P,
Z 12 represents S or P,
R 11 and R 12 , which may be identical or different, represent:
an optionally substituted alkyl, acyl, aryl, alkene or alkyne group (i), or
a saturated or unsaturated, optionally substituted or aromatic carbon-based ring (ii), or
a saturated or unsaturated, optionally substituted heterocycle (iii), these groups and rings (i), (ii) and (iii) may be optionally substituted with substituted phenyl groups, substituted aromatic groups or groups: alkoxycarbonyl or aryloxycarbonyl (—C

Assignees

• Specialty Operations France

Inventors

• Zhou Lichang
• Lee Dongcheel
• Chen Tiffany
• Trezzi Fabio
• Majmudar Shailesh
• Jamasbi Homayoun
• Tran An
• Dufils Pierre-Emmanuel
• Timbart Laurianne
• Wilson David James
• Kang Changheon

Classifications

• C09D133/12

  Homopolymers or copolymers of methyl methacrylate · CPC title

• C09D5/02

  Emulsion paints {including aerosols} · CPC title

• C08F2438/03

  Use of a di- or tri-thiocarbonylthio compound, e.g. di- or tri-thioester, di- or tri-thiocarbamate, or a xanthate as chain transfer agent, e.g . Reversible Addition Fragmentation chain Transfer [RAFT] or Macromolecular Design via Interchange of Xanthates [MADIX] · CPC title

• C08F220/14

  Methyl esters {, e.g. methyl (meth)acrylate} · CPC title

• C08F218/08

  Vinyl acetate · CPC title