Curable fluorocopolymer formed from tetrafluoropropene

a fluoropolymer and copolymer technology, applied in the direction of coatings, etc., can solve the problems of environmental problems, affecting the economics of coatings, and difficult use of such fluoropolymers in coatings, and achieve the effect of economic shipping to users

Inactive Publication Date: 2021-03-25
HONEYWELL INT INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0009]In accordance with a third aspect of the present invention, a product containing the curable fluorocopolymer has a solvent content of 15-50%, and preferably, 15-25%, so as to provide a concentrated product which is economical to ship to the user of the product.

Problems solved by technology

Unfortunately, the use of such fluoropolymers in coatings is difficult owing to their poor solubility in industrial solvents—such as xylene and butyl acetate—which are typically used in the coating industry.
Instead, more exotic solvents must often be used, which not only affect the economics of a coating, but can also present environmental issues owing to, e.g., potential toxicity of the exotic solvents.
Furthermore, polymerization of fluorinated polymers presents a number of challenges, e.g., as detailed in prior application Ser. No. 13 / 645,437 (now U.S. Patent Publication No. 2013 / 0090439 A1), incorporated herein by reference.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

example 1

[0021]19.0 g of butyl acetate, 9.5 g of ethyl vinyl ether, 20.8 g of VEOVA-9, 8.0 g of hydroxybutyl vinyl ether, and 0.62 g of tert-butyl peroxypivalate were charged into a 300 ml stainless steel autoclave equipped with a stirrer. The mixture was solidified with liquid nitrogen, and deaerated to remove the dissolved air. Then, 50 g of 1,3,3,3-tetrafluoro-propene was added to the mixture, and the mixture was gradually heated to 65° C. in an autoclave. The mixture was stirred for 18 hours. After the autoclave was cooled to room temperature, the unreacted monomers were purged and the autoclave was opened. Excess solvent was removed via evaporation.

[0022]Yield 92%; Tg (glass transition temperature) of final copolymer=15° C.; Mn=7348; Mw=13789; Mw / Mn=1.87; final polymer concentration=74.7%; viscosity<500 cps.

example 2

[0023]20.0 g of butyl acetate, 9.1 g of ethyl vinyl ether, 6.0 g of vinyl acetate, 6.7 g of hydroxybutyl vinyl ether, and 0.4 g. of tert-Butyl peroxypivalate were charged into a 300 ml stainless steel autoclave equipped with a stirrer. The mixture was solidified with liquid nitrogen, and deaerated to remove the dissolved air. Then, 40 g of 2,3,3,3-tetrafluoro-propene was added to the mixture, and the mixture was gradually heated to 65° C. in an autoclave. The mixture was stirred for 18 hours. After the autoclave was cooled to room temperature, the unreacted monomers were purged and the autoclave was opened. Excess solvent was removed via evaporation.

[0024]Yield 91%; Tg of final copolymer=11° C.; Mn=5314; Mw=12646; Mw / Mn=2.38; final polymer concentration=73.8%; viscosity<600 cps.

example 3

[0025]20.0 g of butyl acetate, 8.0 g of ethyl vinyl ether, 17.4 g of VEOVA-9, 6.7 g. of hydroxybutyl vinyl ether, and 0.63 g. of tert-butyl peroxypivalate were charged into a 300 ml stainless steel autoclave equipped with a stirrer. The mixture was solidified with liquid nitrogen, and deaerated to remove the dissolved air. Then, 60 g of 1,3,3,3-tetrafluoro-propene was added to the mixture, and the mixture was gradually heated to 65° C. in an autoclave. The mixture was stirred for 18 hours. After the autoclave was cooled to room temperature, the unreacted monomers were purged and the autoclave was opened. Excess solvent was removed via evaporation.

[0026]Yield 93%; Tg of final copolymer=32° C.; Mn=7136; Mw=24103; Mw / Mn=3.37; final polymer concentration=81.1%; viscosity<700 cps.

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Abstract

The present invention is directed to partially fluorinated copolymers and the production thereof. More specifically, the copolymers, which are preferably produced by a solution polymerization process, preferably have at least three units, the first unit selected from 2,3,3,3-tetrafluoropropene and 1,3,3,3-tetrafluoropropene, the second unit having a polymerized monomer selected from the vinyl esters and vinyl ethers, and the third unit having a polymerized monomer derived from a hydroxyl group-containing vinyl ether. The resulting copolymer is environmentally friendly, has favorable molecular weight characteristics, and may be shipped economically in high concentration.

Description

CROSS-REFERENCE TO RELATED APPLICATIONS[0001]The present application is a Continuation of co-pending U.S. patent application Ser. No. 16 / 220,189 filed Dec. 14, 2018, which is a Continuation of U.S. patent application Ser. No. 15 / 477,645 filed Apr. 3, 2017, now U.S. Pat. No. 10,189,918 as granted on Jan. 29, 2019, which is a Continuation of U.S. patent application Ser. No. 14 / 463,747 filed Aug. 20, 2014, now U.S. Pat. No. 9,624,325 as granted on Apr. 18, 2017, which claims the benefit of U.S. Provisional Patent Application Ser. No. 61 / 894,146, filed Oct. 22, 2013, the disclosures of which are hereby incorporated herein by reference. U.S. Provisional Patent Application Ser. No. 61 / 894,146 is related to U.S. patent application Ser. No. 13 / 645,444, filed on Oct. 4, 2012, U.S. patent application Ser. No. 13 / 645,437, filed on Oct. 4, 2012, U.S. Provisional Patent Application Ser. No. 61 / 543,780, filed on Oct. 5, 2011, and U.S. Provisional Patent Application Ser. No. 61 / 543,714, filed on O...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C08F14/18C08F4/76C08F214/18C09D127/12
CPCC08F14/185C08F4/76C08F14/18C09D127/12C08F214/186C08F214/188C08F214/18C08F216/14C08F216/1416C08F218/08
Inventor JIANG, WANCHAOFENG, SHIJUNZHANG, SIYUANLIN, YUNPOSS, ANDREW J.
Owner HONEYWELL INT INC
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