Water dispersion type water and oil repellent composition

• US 6,376,592 B1
• Filed: 08/12/1999
• Issued: 04/23/2002
• Est. Priority Date: 08/24/1998
• Status: Expired due to Term

• Current Assignee: Asahi Glass Company, Limited (AGC, Inc.)
• Original Assignee: Asahi Glass Company, Limited (AGC, Inc.)
• Inventors: Shimada, Toyomichi, Maekawa, Takashige
• Primary Examiner(s): SERGENT, RABON A
• Application Number:
  US09/372,607
• Time in Patent Office: 985 Days
• Field of Search: 811/564, 811/567, 819/2, 428/374, 428/375, 428/378, 428/423.1, 524/507, 524/544, 524/589, 524/591, 524/839, 524/805, 524/457-728, 524/197, 524/198, 524/200, 526/242, 526/301, 526/312, 528/45, 528/70, 525/124
• US Class Current: 524/457
• CPC Class Codes: C08G 18/283 Compounds containing ether groups, e.g. oxyalkylated monohydroxy compounds
• CPC Class Codes: C08G 18/706 the liquid medium being water
• CPC Class Codes: C08G 18/8077 Oximes
• CPC Class Codes: C08G 18/8116 esters of acrylic or alkylacrylic acid having only one isocyanate or isothiocyanate group
• CPC Class Codes: Y10T 428/2931 Fibers or filaments nonconcentric [e.g., side-by-side or eccentric, etc.]
• CPC Class Codes: Y10T 428/2933 Coated or with bond, impregnation or core
• CPC Class Codes: Y10T 428/2938 Coating on discrete and individual rods, strands or filaments
• CPC Class Codes: Y10T 428/31551 Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]

Abstract

A water dispersion type water and oil repellent composition obtained by polymerizing the following polymerizable monomer mixture (b) in the presence of a compound (a) having a blocked isocyanate group and no polymerizable unsaturated group:

(b) a mixture comprising a polymerizable monomer having a polyfluoroalkyl group and a polymerizable monomer having no polyfluoroalkyl group.

Claims

1. A water and oil repellent composition, obtained by polymerizing a polymerizable monomer mixture (b) in the presence of a compound (a) having a blocked isocyanate group and no polymerizable unsaturated group;

wherein said composition is contained in a dispersion in water;

wherein said monomer mixture (b) comprises;

an unsaturated polymerizable monomer having a polyfluoroalkyl group R^f and an unsaturated polymerizable monomer having no polyfluoroalkyl group;

wherein said unsaturated polymerizable monomer having a polyfluoroalkyl group R^f is represented by formula (1)

2. The water and oil repellent composition according to claim 1, wherein R¹ of formula (I) is a bivalent group selected from the group consisting of a —

(CH₂)_n+p—

group, a —

(CH₂)_nCOONR′

(CH₂)_p—

group, a —

(CH₂)_nCONR′

(CH₂)_p—

group, a —

(CH₂)_nSO₂NR′

(CH₂)_p—

group, and a —

(CH₂)_nNHCONR′

(CH₂)_p—

group,

wherein

R′

=a C_1-4 alkyl group or a hydrogen atom; and

n and p≧

0, with

n+p=2 to 22.

3. The water and oil repellent composition according to claim 1, wherein R¹ of formula (I) is a bivalent group selected from the group consisting of a —

(CH₂)_n+p—

group, a —

(CH₂)_nCONR′

(CH₂)_p—

group, and a —

(CH₂)_nSO₂NR′

(CH₂)_p—

group,

wherein

p≧

2, and

n+p=2 to 6.

4. The water and oil repellant composition according to claim 1, wherein X of formula (I) is selected from the group consisting of an alkenyl group, vinyl ether group, vinyl ester group, a (meth)acryl group and a styryl group.

5. The water and oil repellent composition according to claim 1, wherein said compound (a) is selected from the group consisting of blocked tolylene diisocyanate, a blocked diphenyl methane diisocyanate, a blocked naphthalene-1,5-diisocyanate, a blocked xylylene diisocyanate, a blocked hexamethylene diisocyanate, a blocked 4,4-dicyclohexylmethane diisocyanate, a blocked norbornane diisocyanate, and a blocked isophorone diisocyanate.

6. The water and oil repellent composition according to claim 5, wherein said compound (a) is modified with allophanate, isocyanurate or carbodiimide.

7. The water and oil repellent composition according to claim 1, wherein said isocyanate group of said compound (a) is blocked with an oxime, an alcohol, a phenol, a lactam, a N-hydroxyphthalimide, a succinimide, an imidazole, or an ethylacetoacetate.

8. The water and oil repellent composition according to claim 7, wherein said oxime is acetone oxime or methyl ethyl ketoxime.

9. The water and oil repellent composition according to claim 7, wherein said alcohol is 2-ethyl-hexanol, 2-methoxy-1-propanol or 3-methyl-2-penten-4-yne-1-ol.

10. The water and oil repellent composition according to claim 7, wherein said phenol is phenol or 2,4-dimethylphenol.

11. The water and oil repellent composition according to claim 7, wherein said lactam is ε

-caprolactam or pyrrolidinone.

12. The water and oil repellent composition according to claim 1, wherein an amount of said compound (a) is 0.01 to 0.5 times the weight of said monomer mixture (b).

13. The water and oil repellent composition according to claim 1, wherein said unsaturated polymerizable monomer having no polyfluoroalkyl group has a functional group which is reactive with an isocyanate group.

14. The water and oil repellent composition according to claim 13, wherein said functional group reactive with an isocyanate group is selected from the group consisting of an amino group, a hydroxyl group, and a carbamoyl group.

15. The water and oil repellent composition according to claim 1, wherein said unsaturated polymerizable monomer having no polyfluoroalkyl group has a functional group which reacts with said compound (a) or adheres to a surface of a fiber.

16. The water and oil repellent composition according to claim 15, wherein said functional group is selected from the group consisting of an epoxy group, a halogen atom, a blocked isocyanate group, an alkoxy silyl group, a hydroxy silyl group, an N-methylol group, an N-alkoxy group and an imino group.

17. The water and oil repellent composition according to claim 1, wherein an amount of said monomer having polyfluoroalkyl group R^f is 65-99% by weight per 100% by weight of the monomer mixture (b).

18. The water and oil repellent composition according to claim 1, wherein an amount of said monomer having no polyfluoroalkyl group is 1-35% by weight per 100% by weight of the monomer mixture (b).

19. The water and oil repellent composition according to claim 1, wherein said monomer having no polyfluoroalkyl group is selected from the group consisting of a (meth)acrylate, a (meth)acrylamide, an olefin, a vinyl ether, a vinyl ester, a fumarate, a maleate, and mixtures thereof.

20. A fiber treated with the water and oil repellent composition according to claim 1.