METHOD FOR PRODUCTION OF WATER/OIL REPELLENT COMPOSITION AND ARTICLE

• US 20100113665A1
• Filed: 01/06/2010
• Published: 05/06/2010
• Est. Priority Date: 07/11/2007
• Status: Abandoned Application

• Current Assignee: Asahi Glass Company, Limited (AGC, Inc.)
• Original Assignee: Asahi Glass Company, Limited (AGC, Inc.)
• Inventors: HIRONO, Takao, Oomori, Yuuichi, Shimada, Minako, Sugiyama, Kazunori
• Application Number:
  US12/652,785
• Publication Number:
  US 20100113665A1
• Time in Patent Office: Days
• US Class Current: 524/368
• CPC Class Codes: C08F 14/18 Monomers containing fluorine
• CPC Class Codes: C08F 2/04 Polymerisation in solution C08F2/32 takes precedence
• CPC Class Codes: C08F 214/06 Vinyl chloride
• CPC Class Codes: C08F 214/18 Monomers containing fluorine
• CPC Class Codes: C08F 220/1818 C13or longer chain (meth)acrylate, e.g. stearyl (meth)acrylate
• CPC Class Codes: C08F 220/24 containing perhaloalkyl radicals
• CPC Class Codes: C08F 220/36 containing oxygen in addition to the carboxy oxygen , e.g. 2-N-morpholinoethyl (meth)acrylate or 2-isocyanatoethyl (meth)acrylate
• CPC Class Codes: C08F 220/58 containing oxygen in addition to the carbonamido oxygen , e.g. N-methylolacrylamide, N-(meth)acryloylmorpholine
• CPC Class Codes: D06M 15/263 of unsaturated carboxylic acids; Salts or esters thereof
• CPC Class Codes: D06M 15/277 containing fluorine
• CPC Class Codes: D06M 15/3566 containing sulfur
• CPC Class Codes: D06M 2200/11 Oleophobic properties
• CPC Class Codes: D06M 2200/12 Hydrophobic properties

Abstract

To provide a method for producing a water/oil repellent composition which can impart water/oil repellency to a surface of an article and has excellent durability (wash durability and heavy-rain durability) and an article which has water/oil repellency and is less susceptible to deterioration of water/oil repellency when it is washed or in heavy rain.

A method for producing a water/oil repellent composition which comprises polymerizing a monomer component comprising the following monomer (a) in coexistence with the following compound (x) in a medium in the presence of a surfactant and a polymerization initiator: monomer (a) is a compound of the formula (Z—Y)_nX wherein Z is a C_1-20 polyfluoroalkyl group or the like, Y is a bivalent organic group or a single bond, n is 1 or 2, and X is a polymerizable unsaturated group; and the compound (x) is a compound of R^f1—(CH₂)_b-Q-(CH₂)_a—SH, wherein R^f1 is a C_1-30 polyfluoroalkyl group, Q is a bivalent organic group or a single bond, a is an integer of from 1 to 20, and b is an integer of from 0 to 20.

Claims

1. A method for producing a water/oil repellent composition, which comprises polymerizing a monomer component comprising the following monomer (a) in coexistence with the following compound (x) in a medium in the presence of a surfactant and a polymerization initiator:

monomer (a);

a compound of the following formula (1);

(Z—

Y)_nX 

 

(1)

wherein Z is a C_1-20 polyfluoroalkyl group or a group of the following formula (2), Y is a bivalent organic group or a single bond, n is 1 or 2, and X is one of groups of the following formulae (3-1) to (3-5) when n is 1, or one of groups of the following formulae (4-1) to (4-4) when n is 2;

C_iF_2i+1O(CFX¹CF₂O)_jCFX²—

 

 

(2)

wherein i is an integer of from 1 to 6, j is an integer of from 0 to 10, and each of X¹ and X² which are independent of each other, is a fluorine atom or a trifluoromethyl group;

—

CR═

CH₂ 

 

(3-1)

—

C(O)OCR═

CH₂ 

 

(3-2)

—

OC(O)CR═

CH₂ 

 

(3-3)

—

OCH₂-φ

-CR═

CH₂ 

 

(3-4)

—

OCH═

CH₂ 

 

(3-5)

wherein R is a hydrogen atom, a methyl group or a halogen atom, and φ

represents a phenylene group;

—

CH[—

(CH₂)_m—

CR═

CH₂]—

 

 

(4-1)

—

CH[—

(CH₂)_m—

C(O)OCR═

CH₂]—

 

 

(4-2)

—

CH[—

(CH₂)_m—

OC(O)CR═

CH₂]—

 

 

(4-3)

—

OC(O)CH═

CHC(O)O—

 

 

(4-4)

wherein R is a hydrogen atom, a methyl group or a halogen atom, and m is an integer of from 0 to 4;

compound (x);

a compound of the following formula (5);

R^f1—

(CH₂)_b-Q-(CH₂)_a—

SH 

 

(5)

wherein R^f1 is a C_1-30 polyfluoroalkyl group which may have —

O—

, —

OC(O)—

, —

C(O)O—

or —

OH, Q is a bivalent organic group or a single bond, a is an integer of from 1 to 20, and b is an integer of from 0 to 20.

2. The method for producing a water/oil repellent composition according to claim 1, wherein the above Z is a C_1-6 perfluoroalkyl group.

3. The method for producing a water/oil repellent composition according to claim 1, wherein the above Q is —

C(O)O—

, —

OC(O)—

, —

C(O)N(R¹)—

, —

SO₂N(R¹)—

or a single bond, wherein R¹ is a hydrogen atom or a C_1-4 alkyl group.

4. The method for producing a water/oil repellent composition according to claim 1, wherein the above surfactant comprises a nonionic surfactant and a cationic surfactant.

5. The method for producing a water/oil repellent composition according to claim 1, wherein the above polymerization initiator is a radical polymerization initiator.

6. The method for producing a water/oil repellent composition according to claim 1, wherein the above monomer component further contains the following monomer (b):

monomer (b);

a monomer having no polyfluoroalkyl group and having a hydrocarbon group having at least 14 carbon atoms.

7. The method for producing a water/oil repellent composition according to claim 1, wherein the above monomer component further contains the following monomer (c):

monomer (c);

at least one monomer selected from the group consisting of vinyl halide, vinylidene halide and a monomer of the following formula (6);

CH₂═

CR²—

OC(O)R³ 

 

(6)

wherein R² is a hydrogen atom or a methyl group, and R³ is a C_1-8 alkyl group.

8. The method for producing a water/oil repellent composition according to claim 1, wherein the above monomer component further contains the following monomer (d):

monomer (d);

a monomer having no polyfluoroalkyl group and having a crosslinkable functional group.

9. The method for producing a water/oil repellent composition according to claim 1, wherein the proportions of the respective monomers are such that the monomer (a) is from 10 to 100 mass %, the monomer (b) is from 0 to 90 mass %, the monomer (c) is from 0 to 30 mass %, and the monomer (d) is from 0 to 20 mass %, in the monomer component (100 mass %).

10. The method for producing a water/oil repellent composition according to claim 1, wherein the amount of the compound (x) is from 0.1 to 10 parts by mass, the amount of the surfactant is from 1 to 6 parts by mass, and the amount of the polymerization initiator is from 0.1 to 1.0 parts by mass, per 100 parts by mass of the monomer component.

11. An article treated with the water/oil repellent composition produced by the method defined in claim 1.