# US 9,751,972 B2 · Thermally stable biuret and isocyanurate based surface modifying macromolecules and uses thereof

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- Number: US 9,751,972 B2
- Document ID: US9751972B2
- Status: Granted
- Kind: B2
- Application number: 14/188,441
- Filed: 2014-02-24
- Published: 2015-01-22
- Granted: 2017-09-05
- Earliest claimed: 2008-08-28
- Assignees: Interface Biologic Inc.
- Applicants: Interface Biologics Inc.
- Inventors: Sanjoy Mullick; Weilun Chang; Alexandra Piotrowicz; Jeannette Ho; Richard Witmeyer
- Web page: https://patentgrep.com/patent/US9751972B2

## CPC

- C08G 18/714: {containing nitrogen in addition to isocyanate or isothiocyanate nitrogen}
- C08G 18/227: {of antimony, bismuth or arsenic}
- C08G 18/2885: {containing halogen atoms}
- C08G 18/44: Polycarbonates
- C08G 18/6208: {Hydrogenated polymers of conjugated dienes}
- C08G 18/755: {and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate}
- C08G 18/7831: {containing biuret groups}
- C08G 18/791: {containing isocyanurate groups}
- C08G 18/792: {formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates}
- C08G 18/8087: {containing halogen atoms}
- C08L 27/06: Homopolymers or copolymers of vinyl chloride
- C08L 75/04: Polyurethanes
- C08L 77/00: Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain (of polyhydrazides C08L79/06; of polyamideimides or polyamide acids C08L79/08); Compositions of derivatives of such polymers
- C08L 81/06: Polysulfones; Polyethersulfones
- C08L 83/04: Polysiloxanes
- C08L 2205/025: containing two or more polymers of the same hierarchy C08L, and differing only in parameters such as density, comonomer content, molecular weight, structure
- Y10T 428/139: Open-ended, self-supporting conduit, cylinder, or tube-type article
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- Y10T: TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION

## Abstract

The invention relates to surface modifying macromolecules (SMMs) having high degradation temperatures and their use in the manufacture of articles made from base polymers which require high temperature processing. The surface modifier is admixed with the base polymer to impart alcohol and water repellency properties.

## Claims

### Claim 1

An admixture comprising a base polymer and a surface modifier of formula (I) or (II):
wherein
(i) A is a soft segment;
(ii) B is a hard segment, and B′, when present, is a hard segment comprising a urethane; and
(iii) each G is a surface active group comprising polyfluoroalkyl;
(iv) n is an integer from 0 to 10;
wherein said surface modifier has a thermal degradation temperature of at least 290° C. and a theoretical molecular weight of less than 10,000 Daltons;
wherein said admixture is formed by melt-processing said base polymer with said surface modifier; and wherein:
(a) A is diethylene glycol-orthophthalic anhydride polyester, and B is formed from isophorone diisocyanate (IPDI) trimer;
(b) A is polytetramethylene oxide, and B is formed from isophorone diisocyanate (IPDI) trimer;
(c) A is poly(diethylene glycol)adipate, and B is formed from isophorone diisocyanate (IPDI) trimer;
(d) A is poly(hexamethylene carbonate), and B is formed from isophorone diisocyanate (IPDI) trimer;
(e) A is poly(ethyleneglycol)-block-poly(propyleneglycol))-block-poly(ethylene glycol), and B is formed from isophorone diisocyanate (IPDI) trimer;
(f) A is hydrogenated polybutadiene, and B is formed from isophorone diisocyanate (IPDI) trimer;
(g) A is hydrogenated polybutadiene, and B is formed from hexamethylene diisocyanate (HDI) trimer; or
(h) A is hydrogenated polyisoprene, and B is formed from isophorone diisocyanate (IPDI) trimer.

### Claim 2 (depends on 1)

The admixture of claim 1, wherein said surface active group is selected from the group consisting of radicals of the general formula CHmF(3-m)(CF2)rCH2CH2— and CHmF(3-m)(CF2)s(CH2CH2O)χ—, wherein
m is 0, 1, 2, or 3;
χ is an integer between 1-10;
r is an integer between 2-20; and
s is an integer between 1-20.

### Claim 3 (depends on 2)

The admixture of claim 2, wherein m is 0 or 1.

### Claim 4 (depends on 2)

The admixture of claim 2, wherein each surface active group is selected, independently, from the group consisting of (CF3)(CF2)5CH2CH2O—, (CF3)(CF2)7CH2CH2O—, (CF3)(CF2)5CH2CH2O—, CHF2(CF2)3CH2O—, and (CF3)(CF2)2CH2O—.

### Claim 5 (depends on 1)

The admixture of claim 1, wherein A is diethylene glycol-orthophthalic anhydride polyester, and B is formed from isophorone diisocyanate (IPDI) trimer.

### Claim 6 (depends on 1)

The admixture of claim 1, wherein A is polytetramethylene oxide, and B is formed from isophorone diisocyanate (IPDI) trimer.

### Claim 7 (depends on 1)

The admixture of claim 1, wherein A is poly(diethylene glycol)adipate, and B is formed from isophorone diisocyanate (IPDI) trimer.

### Claim 8 (depends on 1)

The admixture of claim 1, wherein A is poly(hexamethylene carbonate), and B is formed from isophorone diisocyanate (IPDI) trimer.

### Claim 9 (depends on 1)

The admixture of claim 1, wherein A is poly(ethyleneglycol)-block-poly(propyleneglycol))-block-poly(ethylene glycol), and B is formed from isophorone diisocyanate (IPDI) trimer.

### Claim 10 (depends on 1)

The admixture of claim 1, wherein A is hydrogenated polybutadiene, and B is formed from isophorone diisocyanate (IPDI) trimer.

### Claim 11 (depends on 1)

The admixture of claim 1, wherein A is hydrogenated polybutadiene, and B is formed from hexamethylene diisocyanate (HDI) trimer.

### Claim 12 (depends on 1)

The admixture of claim 1, wherein A is hydrogenated polyisoprene, and B is formed from isophorone diisocyanate (IPDI) trimer.

### Claim 13

A surface modifier of formula (I) or (II):
wherein
A is formed from 1,12-dodecane diol (DDD),
B is formed from isophorone diisocyanate (IPDI) trimer,
each G is a surface active group comprising polyfluoroalkyl, and
n is an integer from 0 to 10;
wherein said surface modifier has a thermal degradation temperature of at least 270° C. and a theoretical molecular weight of less than 10,000 Daltons.

### Claim 14 (depends on 1)

The admixture of claim 1, wherein said base polymer is selected from polypropylenes, polyethylenes, polyesters, polyurethanes, nylons, polysilicones, polystyrene, poly(methyl methacrylates), polyvinylacetates, polycarbonates, polyacrylonitrile-butadiene), polyvinylchloride (PVC), polysulfones, and polyethersulfones, and blends thereof.

### Claim 15 (depends on 14)

The admixture of claim 14, wherein said base polymer is selected from polyesters.

### Claim 16 (depends on 1)

The admixture of claim 1, wherein said admixture is formed by (i) mixing said base polymer with a surface modifier of claim 1 to form a mixture; and (ii) heating said mixture above 220° C.

### Claim 17 (depends on 1)

An article comprising the admixture of claim 1.

### Claim 18 (depends on 17)

The article of claim 17, wherein said admixture is molded, melt blown, melt spun, or melt extruded.