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Poly(hydroxystyrene) stain resist

a technology of hydroxystyrene and stain resistance, applied in the field of poly(hydroxystyrene) stain resistance, can solve the problems of limited uv stability, limited fastness, limited coffee and mustard stain resistance,

Inactive Publication Date: 2009-10-15
EI DU PONT DE NEMOURS & CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The polymer composition effectively blocks coffee and mustard stains, retains performance through washing, and exhibits superior UV light stability, outperforming commercial products in durability and resistance to red dyes like KOOL-AID.

Problems solved by technology

The properties of many commercial stain blockers are frequently not retained during washing of the substrate treated with said stain blocker, suffer from light fastness limitations, and have marginal resistance to coffee and mustard stains.
Many commercial products when blended with phenol-formaldehyde resins provide better stain blocking and durability, but still provide only limited UV stability (light fastness) and have limited coffee and mustard stain resistance.

Method used

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  • Poly(hydroxystyrene) stain resist
  • Poly(hydroxystyrene) stain resist
  • Poly(hydroxystyrene) stain resist

Examples

Experimental program
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Effect test

example 1

[0134]Into a 500-mL round-bottom flask was added poly(p-hydroxystyrene) (20 g, M.W. 11,200, Triquest LP) and dimethyl formamide (DMF, 160 mL). To the resulting solution was added sulfur trioxide N,N-dimethylformamide complex (SO3.DMF, 12.7 g g, 83.33 mmol). The reaction mixture was heated at 150° C. for 18 h in which time the solution went from yellow to amber. After cooling to room temperature the solvent was removed on a rotary evaporator. The resulting oil was re-evaporated several times from 50 mL methanol. The resulting oil was triturated with diethyl ether until a solid formed. The solid was collected by filtration and dried under vacuum to yield solid 50% sulfonated poly(p-hydroxystyrene), 32.6 g. Elemental analysis: C, 54.78%; H, 6.75%; N, 5.71%; S, 8.37%. A sample for testing was prepared by adding the above solid (15 g) to deionized water (75 mL) and of 1N NaOH (14 mL). This solution was applied to carpet using Test Method 1. The carpet was evaluated for stain resistance u...

example 2

[0135]Into a 500-mL round-bottom flask was added poly(p-hydroxystyrene-t-butylacrylate) polymer (20 g, 61:39; Dupont Electronic Polymers LLP, Lot No# 10020-51-FDP, see Materials) and DMF (120 mL). To the resulting solution was added SO3.DMF (7.6 g) and the resulting solution heated at 150° C. with stirring for 18 h. The reaction mixture was cooled to room temperature and the solvent removed in vacuo to give a brown oil. The oil was added to diethyl ether (200 mL) and stirred for 30 min.; decanting the diethyl ether and repeating the procedure several times caused the polymer to solidify. The solid was dried under high vacuum to give the product, 50% sulfonated poly(p-hydroxystyrene-acrylic acid) (61:39), 28.17 g. 1H and 13C NMR showed that the t-butyl group had been removed in the course of the sulfonation. Elemental analysis: C, 53.66%; H, 7.08%; N, 6.53%; S, 5.62%. A sample for stain blocker testing was prepared by dissolving the above polymer (15 g) in deionized water (50 mL) and...

example 3

[0136]Into a 500-mL round-bottom flask was added poly(p-hydroxystyrene-t-butylacrylate) polymer (20 g, 61:39; Dupont Electronic Polymers LLP, Lot No. 10020-51-FDP, see Materials) and DMF (120 mL). To the resulting solution was added SO3.DMF (3.8 g) and the resulting solution heated under nitrogen to 150° C. with stirring for 18 h. The reaction mixture was cooled to room temperature and the solvent removed in vacuo to give a brown oil. The oil was added to diethyl ether (150 mL) and stirred for 30 min. Decanting the diethyl ether and repeating the procedure several times caused the polymer to solidify.

[0137]The solid was dried under high vacuum to give the product, 25% sulfonated poly(p-hydroxystyrene acrylic acid) (61:39), 26.48 g. 1H and 13C NMR showed that the t-butyl group had been removed in the course of the sulfonation. Elemental analysis: C, 58.42%; H, 7.47%; N, 6.6%; S, 3.09%. A sample for testing was prepared by dissolving the above polymer (15 g) in deionized water (60 mL)...

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Abstract

A composition for use as a stain blocker and a method of treating substrates therewith, said composition comprising a polymer of Formula 1 having the following repeating units in random sequencewhereinR1 is H, methyl or ethyl;R2 and R3 are each independently H, C1 to about C10 alkyl, —COOR4, CONR5R6, or —CN;R4 is M, C1 to about C20 alkyl, or C6 to C10 aryl;R5 and R6 are each independently H, C1 to C10 alkyl, C6 to C10 aryl, or R5 and R6 together with the nitrogen atom form a morpholine, pyrrolidine, or piperidine ring;R7 is a C4 to C8 alkyl group;M is H, an alkali metal or alkali earth metal;h is about 10 to 100 mole %;i is 0 to about 80 mole %;j is 0 to about 60 mole %;k and n are each independently 0 to about 40 mole %; andm is 0.01 to about 0.5;provided that h+i+j+k+n equals 100, andprovided that i+j+k+n is greater than zero, except when h is 100%.

Description

BACKGROUND OF THE INVENTION[0001]The properties of many commercial stain blockers are frequently not retained during washing of the substrate treated with said stain blocker, suffer from light fastness limitations, and have marginal resistance to coffee and mustard stains. Many commercial products when blended with phenol-formaldehyde resins provide better stain blocking and durability, but still provide only limited UV stability (light fastness) and have limited coffee and mustard stain resistance.[0002]Allen, in U.S. Pat. No. 5,574,106, discloses polymers wherein a strong acid-containing monomer, a weak acid-containing monomer, and a neutral aromatic-containing monomer are polymerized. More specifically, Allen describes stain resist compositions formed from (a) from about 8% to about 40% of a styrene, substituted styrene or phenolic monomer free of carboxylic acid groups and strong acid groups, (b) from about 9% to about 20% of an ethylenically unsaturated strong acid monomer havi...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): D06M15/233
CPCD06M15/227D06M15/233D06M15/263D06M15/285D06M15/31C08F8/36C08F112/14C08F8/44C08F212/14C08F2220/1825C08F220/1804C08F112/24C08F212/24
Inventor SHUEY, STEVEN WILLISJACOBSON, STEPHEN ERNESTLANGLEY, MELEA RENAMURPHY, PETER MICHAELSHAH, MUKESH CHIMANLAL
Owner EI DU PONT DE NEMOURS & CO