Oil water and solvent resistant paper by treatment with fluorochemical copolymers
First Claim
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1. A copolymer composition for treating paper and paper products to impart water, oil or grease repellency comprising monomers copolymerized in the following percentages by weight:
- (a) from about 60% to about 90% of at least one monomer of formula I;
space="preserve" listing-type="equation">R.sub.f --Q--A--C(O)--C(R)═
CH.sub.2 IwhereinRf is a straight or branched-chain perfluoroalkyl group containing from 2 to about 20 carbon atoms,R is H or CH3,A is O, S, or N(R'"'"'), wherein R'"'"' is H or an alkyl of from 1 to about 4 carbon atoms,Q is alkylene of 1 to about 15 carbon atoms, hydroxyalkylene of 3 to about 15 carbon atoms, --(Cn H2n)(OCq H2q)m --, --SO2 --NR'"'"'(Cn H2n)--, or --CONR'"'"'(Cn H2n)--, wherein R'"'"' is H or alkyl of from 1 to about 4 carbon atoms, n is 1 to about 15, q is 2 to about 4, and m is 1 to about 15;
(b) from about 10% to about 40% of at least one monomer of formula II;
space="preserve" listing-type="equation">(R.sub.1).sub.2 N--CH.sub.2 CH.sub.2 --O--C (O)--C(R.sub.2)═
CH.sub.2 IIwhereinR1 is an alkyl group containing from 1 to 3 carbon atoms, R2 is H or an alkyl radical of 1 to about 4 carbon atoms, and wherein the nitrogen is from about 40% to 100% salinized; and
,(c) from about 1% to about 7% of at least one monomer of formula III or IV, or a mixture thereof;
##STR4## or
space="preserve" listing-type="equation">Cl--CH.sub.2 --CH(OH)CH.sub.2 --O--C(O)--C(R.sub.4)═
CH.sub.2 IV,whereinR3 and R4 are each independently H or the same or different alkyl radical of 1 to about 4 carbon atoms.
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Abstract
A copolymer composition for treating paper and paper products to impart water, oil or grease repellency comprising monomers copolymerized in the following percentages by weight:
(a) from about 60% to about 90% of at least one monomer of formula I:
R.sub.f -Q-A-C(O)-C(R)═CH.sub.2 I
wherein
Rf is a C2-20 straight or branched-chain perfluoroalkyl group,
R is H or CH3,
A is O, S, or N(R'"'"'), wherein R'"'"' is H or a C1-14 alkyl,
Q is C1-15, alkylene, C3-15 hydroxyalkylene, --(Cn H2n)(OCq H2q)m --, --SO2 --NR'"'"'(Cn H2n)--, or --CONR'"'"'(Cn H2n)--, wherein R'"'"' is H or C1-4 alkyl, n is 1 to 15, q is 2 to 4, and m is 1 to 15;
(b) from about 10% to about 40% of at least one monomer of formula II:
(R.sub.1).sub.2 N--CH.sub.2 CH.sub.2 --O--C(O)--C(R.sub.2)═CH.sub.2 II
wherein R1 is C1-3 alkyl, R2 is H or a C1-4 alkyl radical, and wherein the nitrogen is from about 40% to 100% salinized; and,
(c) from about 1% to about 7% of at least one monomer of formula III or IV, or a mixture thereof: ##STR1## or
Cl--CH.sub.2 --CH(OH)CH.sub.2 --O--C(O)--C(R.sub.4)═CH.sub.2 IV,
wherein
R3 and R4 are each independently H or the same or different C1-4 alkyl radical is disclosed.
62 Citations
9 Claims
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1. A copolymer composition for treating paper and paper products to impart water, oil or grease repellency comprising monomers copolymerized in the following percentages by weight:
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(a) from about 60% to about 90% of at least one monomer of formula I;
space="preserve" listing-type="equation">R.sub.f --Q--A--C(O)--C(R)═
CH.sub.2 Iwherein Rf is a straight or branched-chain perfluoroalkyl group containing from 2 to about 20 carbon atoms, R is H or CH3, A is O, S, or N(R'"'"'), wherein R'"'"' is H or an alkyl of from 1 to about 4 carbon atoms, Q is alkylene of 1 to about 15 carbon atoms, hydroxyalkylene of 3 to about 15 carbon atoms, --(Cn H2n)(OCq H2q)m --, --SO2 --NR'"'"'(Cn H2n)--, or --CONR'"'"'(Cn H2n)--, wherein R'"'"' is H or alkyl of from 1 to about 4 carbon atoms, n is 1 to about 15, q is 2 to about 4, and m is 1 to about 15; (b) from about 10% to about 40% of at least one monomer of formula II;
space="preserve" listing-type="equation">(R.sub.1).sub.2 N--CH.sub.2 CH.sub.2 --O--C (O)--C(R.sub.2)═
CH.sub.2 IIwherein R1 is an alkyl group containing from 1 to 3 carbon atoms, R2 is H or an alkyl radical of 1 to about 4 carbon atoms, and wherein the nitrogen is from about 40% to 100% salinized; and
,(c) from about 1% to about 7% of at least one monomer of formula III or IV, or a mixture thereof;
##STR4## or
space="preserve" listing-type="equation">Cl--CH.sub.2 --CH(OH)CH.sub.2 --O--C(O)--C(R.sub.4)═
CH.sub.2 IV,wherein R3 and R4 are each independently H or the same or different alkyl radical of 1 to about 4 carbon atoms. - View Dependent Claims (2, 3, 4)
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5. A method of treating paper or paper products to impart water, oil or grease repellency comprising application to the surface of the paper or paper product, or addition to the pulp prior to paper or paper product formation, of an effective amount of a composition comprising monomers copolymerized in the following percentages by weight:
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(a) from about 60% to about 90% of at least one monomer of formula I;
space="preserve" listing-type="equation">R.sub.f --Q--A--C (O)--C(R)═
CH.sub.2 Iwherein Rf is a straight or branched-chain perfluoroalkyl group containing from 2 to about 20 carbon atoms, R is H or CH3, A is O, S, or N(R'"'"'), wherein R'"'"' is H or an alkyl of from 1 to about 4 carbom atoms, Q is alkylene of 1 to about 15 carbon atoms, hydroxyalkylene of 3 to about 15 carbon atoms, --(Cn H2n)(OCq H2q)m --, --SO2 --NR'"'"'(Cn H2n)--, or --CONR'"'"'(Cn H2n)--, wherein R'"'"' is H or alkyl of from 1 to about 4 carbon atoms, n is 1 to about 15, q is 2 to about 4, and m is 1 to about 15; (b) from about 10% to about 40% of at least one monomer of formula II;
space="preserve" listing-type="equation">(R.sub.1).sub.2 N--CH.sub.2 CH.sub.2 --O--C(O)--C(R.sub.2)═
CH.sub.2 IIwherein R1 is an alkyl group containing from 1 to 3 carbon atoms, R2 is H or an alkyl radical of 1 to about 4 carbon atoms, and wherein the nitrogen is from about 40% to 100% salinized; and
,(c) from about 1% to about 7% of at least one monomer of formula III or IV, or a mixture thereof;
##STR5## or
space="preserve" listing-type="equation">Cl--CH.sub.2 --CH(OH)CH.sub.2 --O--C(O)--C(R.sub.4)═
CH.sub.2IV,wherein R3 and R4 are each independently H or the same or different alkyl radical of 1 to about 4 carbon atoms. - View Dependent Claims (6, 7)
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8. A paper or paper product which has been treated with a composition comprising monomers copolymerized in the following percentages by weight:
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(a) from about 60% to about 90% of at least one monomer of formula I;
space="preserve" listing-type="equation">R.sub.f --Q--A--C(O)--C(R)═
CH.sub.2 Iwherein Rf is a straight or branched-chain perfluoroalkyl group containing from 2 to about 20 carbon atoms, R is H or CH3, A is O, S, or N(R'"'"'), wherein R'"'"' is H or an alkyl of from 1 to about 4 carbom atoms, Q is alkylene of 1 to about 15 carbon atoms, hydroxyalkylene of 3 to 15 carbon atoms, --(Cn H2n)(OCq H2q)m --, --SO2 --NR'"'"'(Cn H2n)--, or --CONR'"'"'(Cn H2n)--, wherein R'"'"' is H or an alkyl of from 1 to about 4 carbon atoms, n is 1 to about 15, q is 2 to about 4, and m is 1 to about 15; (b) from about 10% to about 40% of at least one monomer monomers of formula II;
space="preserve" listing-type="equation">(R.sub.1).sub.2 N--CH.sub.2 CH.sub.2 --O--C(O)--C(R.sub.2)═
CH.sub.2 IIwherein R1 is an alkyl group containing from 1 to 3 carbons, R2 is H or an alkyl radical of 1 to about 4 carbon atoms, and wherein the nitrogen is from about 40% to 100% salinized; and
,(c) from about 1% to about 7% of at least one monomer of formula III or IV, or a mixture thereof;
##STR6## or
space="preserve" listing-type="equation">Cl--CH.sub.2 --CH(OH)CH.sub.2 --O--C(O)--C(R.sub.4)═
CH.sub.2IV,wherein R3 and R4 are each independently H or the same or different alkyl radical of 1 to about 4 carbon atoms. - View Dependent Claims (9)
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Current AssigneeThe Chemours Company FC, LLC (The Chemours Company)
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Original AssigneeE. I. du Pont de Nemours and Company (Corteva, Inc.)
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InventorsFitzgerald, John J.
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Primary Examiner(s)Schofer, Joseph L.
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Assistant Examiner(s)Cheng, Wu C.
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Application NumberUS08/631,594Time in Patent Office543 DaysField of Search526/273, 526/245, 526/288, 526/310, 526/328.5US Class Current526/273CPC Class CodesC08F 220/24 containing perhaloalkyl rad...D21H 17/34 obtained by reactions only ...D21H 21/16 Sizing or water-repelling a...D21H 27/10 Packing paper packaging mat...
