Perfluoroalkyl substituted acrylate monomers and polymers thereof
View Patent ↗Fluoroalkyl amidoalkyl alcohols of the formula are disclosed and their corresponding (meth)acrylate esters. These fluoroalkyl amidoalkyl (meth)acrylate monomers can be copolymerized with a wide variety of conventional ethylenically unsaturated monomers. The resulting copolymers are useful as water, oil- and grease-proofing agents for paper, textiles and hard surfaces such as masonry and wood.
1. A copolymer comprising monomers copolymerized in the following percentages by weight, relative to the total weight of the copolymer:
a) 45–90% by weight of a monomer of formula II
wherein
R F is a straight or branched-chain perfluoroalkyl group containing 4 to 20 carbon atoms,
R 1 is H or CH 3 ,
R 2 is H or an alkyl group with 1 to 4 carbon atoms, and
m and n are, independently of each other, an integer from 2 to 11; and
b) 5–30% by weight of a monomer of formula III
(R 2 ) 2 N—(CH 2 ) k —X 1 —C(═O)—C(R 1 )═CH 2 (III)
in which the nitrogen atom is partially or completely quaternized or in the form of a salt and X 1 is O or N(R 2 ) and wherein
R 1 and R 2 are defined as above, each R 2 is the same or different, and
k is 2 to 4; and
c) 0–10% by weight of at least one copolymerizable nonfluorinated vinyl monomer.
2. A copolymer according to claim 1 , wherein c) is zero.
3. A copolymer according to claim 1 , in which the monomers are copolymerized in the following percentages by weight, relative to the total weight of the copolymers:
a) 65–85% by weight; b) 5–30% by weight and c) 0–10% by weight.
4. A copolymer according to claim 1 , wherein R F is a fully fluorinated, linear carbon chain with an average of about 4 to 16 carbon atoms, R 2 is hydrogen or an alkyl group with 1 to 2 carbon atoms, n is an integer from 5 to 10, and m is an integer from 2 to 6.
5. A copolymer according to claim 1 , in which the monomer of the formula III is selected from the group consisting of N,N-dimethylaminoethyl (meth)acrylate; N,N-diethylaminoethyl (meth)acrylate; N,N-dimethylaminopropyl methacrylamide and N-tert. butylaminoethyl methacrylate and their salts.
6. A copolymer according to claim 1 , in which the copolymerizable nonfluorinated vinyl monomer is selected from the group consisting of styrene, methyl methacrylate, N-methylol acrylamide, 2-hydroxyethyl methacrylate, acrylic acid, glycidyl methacrylate, vinylidene chloride, vinyl acetate, 1-vinyl-2-pyrrolidinone, acrylonitrile, methacrylonitrile, vinyl chloride.