WO2002079564A1

WO2002079564A1 - Fabric rinse composition comprising a triazine uv absorber

Info

Publication number: WO2002079564A1
Application number: PCT/EP2002/003008
Authority: WO
Inventors: Robert Hochberg; Hauke Rohwer
Original assignee: Ciba Specialty Chemicals Holding Inc.
Priority date: 2001-03-27
Filing date: 2002-03-19
Publication date: 2002-10-10
Also published as: US20040078901A1; KR20040019284A; CA2438800A1; EP1373630A1; JP2004525275A; BR0208390A; CN1500166A; MXPA03008742A

Abstract

Disclosed is a fabric rinse composition comprising a) 0.1 to 10% by weight of a UV absorber selected from a hydroxyaryl-1, 3, 5- triazine of the formula (I), wherein R1 is hydrogen; c1-c4-Alkoxy; or halogen; R2 is mono-C1-C4 alkylamino; a radical of the formula (I'); X is C2-C4 alkylen; Y1, Y2 independently from each other are C1-C4 alkyl or C1-C4 alkyl which is substituted by halogen, cyano hydroxy or C1-C4 alkoxy; or Y1 and Y2 or Y1 and Y3 together with the nitrogen atom form a 5- to 7- membered heterocycle; Y3 is hydrogene; C1-C4 alkyl; C3-C4 alkenyl; or C1-C4 alkyl, C3-C4 alkenyl which is substituted by cyano, hydroxy, C1-C4 alkoxy, phenyl or C1-C4 alkoxycarbonyl; or Y1, Y2 and Y3 together with the binding nitrogen atom form a pyrrolidine, piperidine or morpholine radical; A is the counter ion; b) 5 to 25% by weight, based on the total weight of the composition of a fabric care ingredient; and c) the remainder being substantially water.

Description

Fabric Rinse Composition comprising a triazine UV absorber

The present invention relates to a composition for the treatment of textiles, in particular to a fabric care composition containing a UV absorber; and to a method of treating textiles with the composition, which method imparts to textile fiber material so treated, in addition to an excellent UV Protecting Factor (UPF), and other desirable properties.

It is known that light radiation of wavelengths 280-400 nm permits tanning of the epidermis. Also known is that rays of wavelengths 280-320 nm (termed UV-B radiation), cause erythemas and skin burning which can inhibit skin tanning.

Radiation of wavelengths 320-400 nm (termed UV-A radiation) is known to induce skin tanning but can also cause skin damage, especially to sensitive skin which is exposed to sunlight for long periods. Examples of such damage include loss of skin elasticity and the appearance of wrinkles, promotion of the onset of erythemal reaction and the inducement of phototoxic or photoallergic reactions.

Any effective protection of the skin from the damaging effects of undue exposure to sunlight clearly needs to include means for absorbing both UV-A and UV-B components of sunlight before they reach the skin surface.

Traditionally, protection of exposed human skin against potential damage by the UV components in sunlight has been effected by directly applying to the skin a preparation containing a UVA. In areas of the world, e.g. Australia and America, which enjoy especially sunny climates, there has been a great increase in the awareness of the potential hazards of undue exposure to sunlight, compounded by fears of the consequences of alleged damage to the ozone layer. Some of the more distressing embodiments of skin damage caused by excessive, unprotected exposure to sunlight are development of melanomas or carcinomas on the skin.

One aspect of the desire to increase the level of skin protection against sunlight has been the consideration of additional measures, over and above the direct protection of the skin. For example, consideration has been given to the provision of protection to skin covered by clothing and thus not directly exposed to sunlight.

Most natural and synthetic textile materials are at least partially permeable to UV components of sunlight. Accordingly, the mere wearing of clothing does not necessarily provide skin beneath the clothing with adequate protection against damage by UV radiation. Although clothing containing a deeply coloured dye and/or having a tight weave texture may provide a reasonable level of protection to skin beneath it, such clothing is not practical in hot sunny climates, from the standpoint of the personal comfort of the wearer.

There is a need, therefore, to provide protection against UV radiation for skin which lies underneath clothing, including lightweight summer clothing, which is undyed or dyed only in pale shades. Depending on the nature of the dyestuff, even skin beneath clothing dyed in some dark shades may also require protection from UV radiation.

Such lightweight summer clothing normally has a density of of less than 200 g/m^ and has a sun protection factor rating between 1 .5 and 20, depending on the type of fiber from which the clothing is manufactured.

The UPF rating of a sun protectant (sun cream or clothing) may be defined as the multiple of the time taken for the average person wearing the sun protectant to suffer sun burning under average exposure to sun. For example, if an average person would normally suffer sun burn after 30 minutes under standard exposure conditions, a sun protectant having an UPF rating of 5 would extend the period of protection from 30 minutes to 2 hours and 30 minutes. For people living in especially sunny climates, where mean sun burn times are minimal, e.g. only 15 minutes for an average fair-skinned person at the hottest time of the day, UPF ratings of about 20 are desired for lightweight clothing.

The selection of a suitable UVA, for use in a method for effecting an increase in the UPF value of a textile fiber material (often referred to as a "UV cutting" treatment method), has to take into account the fact that the treated textile fiber material must satisfy performance criteria in a wide range of areas, such as washfastness, lightfastness and tear resistance, apart from its UPF value.

For example, the currently known non-reactive UVAs generally exhibit an inadequate washfastness when applied to cotton. Consequently, their use in UV cutting applications (and also for the purpose of improving the lightfastness) is limited.

The present invention provides, therefore, as a first aspect, a stable, concentrated fabric rinse composition comprising a) 0.1 to 10, preferably 0.1 to 5% by weight of a UV absorber selected from a hydroxyaryl- 1 ,3,5-triazine of the formula

, wherein

R, is hydrogen; C,-C₄alkyl; C C₄-Alkoxy; or halogen;

R₂ is A^' ;

X is C₂-C₄alkylen;

Y„ Y₂ independently from each other are C,-C₄alkyl or C,-C₄alkyl which is substituted by halogen, cyano hydroxy or C,-C₄alkoxy; or Y, and Y₂ or Y, and Y₃ together with the nitrogen atom form a 5- to 7-membered heterocycle Y₃ is hydrogen; C,-C₄alkyl; C₃-C₄alkenyl; or C,-C₄alkyl, C₃-C₄alkenyl which is substituted by cyano, hydroxy, C,-C₄alkoxy, phenyl or C₁-C₄alkoxycarbonyl; or Y„ Y₂ and Y₃ together with the binding nitrogen atom form a pyrrolidine, piperidine or morpholine radical; A is the counter ion; b) 5 to 25% by weight, based on the total weight of the composition of a fabric care ingredient; and c) the remainder being substantially water.

Preferably in the present composition UV absorbers of formula

(2) , is used, wherein

R, is hydrogen or C^C.alkyl;

R₂ is mono-C,-C₅alkylamino; di-C,-C₅alkylamino; a radical of the formula Y Υ. '

X is C₂-C₄alkylen;

Y„ Y₂ and Y₃ independently from each other are C,-C₃alkyl; and

A is as defined as in formula (1 ).

Preferably, in formula (2)

R, is hydrogen or C,-C₂alkyl;

R₂ is di-C,-C₂alkylamino; N⁺(C,-C₂alkyl)₃-A-; N⁺(C,-C₂alkyl)₂CH₃-A-; and

A is as defined as in formula (1).

A is preferably selected from o ; or I^".

Most preferably, in formula (2)

R₂ is -N(CH₃)₃; -N(C₂H₅)₂; -N⁺(CH₃)₃ A; or -N⁺(C₂H₅)CH₃ A\

Mostly preferred are compounds of formula (2) wherein R, is hydrogen or methyl; is -N(CH₃)₃; -N(C₂H₅)₂; -N⁺(CH₃)₃ A; or -N⁺(C₂H₅)CH₃ A^"; is -CH₂CH₂-; or -CH₂-CH₂-CH₂-; and

The UV absorber used in the present composition readily absorbs UV light, especially in the range I = 300 to 400 nm, and converts the absorbed energy, by a chemical intermediate reaction, into non-interfering, stable compounds or into non-interfering forms of energy. The UV absorber should, of course, be compatible with the rinse cycle fabric softener composition. Preferably, the UV absorber used is one which is capable of being absorbed on to the washed textile article during a rinse cycle fabric softener treatment.

Preferred UV absorbers used in the present composition are listed in Table 1 :

Table 1

Compound of β, β. X Counter ion formula

(l e) H N⁺(C₂H₅)₂CH₃ -(CH₂)₂- r

(If) H N⁺(C₂H₅)₂CH₃ -(CH₂)₂- hydrogensulfate/ methosulfate

0g) H N⁺(CH₃)₃ -(CH₂)₃- hydrogensulfate/ methosulfate

Oh) CH₃ N⁺(CH₃)₃ -(CH₂)₃- hydrogensulfate/ methosulfate

(I I) CH₃ N⁺(C2H5)CH₃ -(CH₂)₂- hydrogensulfate/ methosulfate

The counter-ions hydrogensulfate and methosulfate are formed depending on varying reaction conditions and are present in different weight ratios.

The compounds of formula (1) are known and may be prepared in the manner, e.g., described in EP-A-0357545.

Fabric softeners (component (b)) suitable for use herein are selected from the following classes of compounds:

(i) Cationic quaternary ammonium salts. The counter ion of such cationic quaternary ammonium salts may be a halide, such as chloride or bromide, methyl sulphate, or other ions well known in the literature. Preferably the counter ion is methyl sulfate or any alkyl sulfate or any halide, methyl sulfate being most preferred for the dryer-added articles of the invention.

Examples of cationic quaternary ammonium salts include but are not limited to:

1 . Acyclic quaternary ammonium salts having at least two C₈ to C₃₀, preferably C₁₂ to C₂₂ alkyl or alkenyl chains, such as: ditallowdimethyl ammonium methylsulfate, di(hydrogenated tallow)dimethyl ammonium methylsulfate, distearyldimethyl ammonium methylsulfate or chloride, dicocodimethyl ammonium methylsulfate and the like. It is especially preferred if the fabric softening compound is a water insoluble quaternary ammonium material which comprises a compound having two C,₂ to C₁₈ alkyl or alkenyl groups connected to the molecule via at least one ester link. It is more preferred if the quaternary ammonium material has two ester links present. An especially preferred ester-linked quaternary ammonium material for use in the invention can be represented by the formula:

wherein each R₃ group is independently selected from C, to C₄ alkyl, hydroxyalkyl or C₂ to C₄ alkenyl groups; T is either o (3a) — o — c — or o

II

(3b) — c — o — and wherein each R₄ group is independently selected from C₈ to C₂₈ alkyl or alkenyl groups; and e is an integer from 0 to 5.

A second preferred type of quaternary ammonium material can be represented by the formula:

wherein R₃, e and R₄ are as defined above.

2. Cyclic quaternary ammonium salts of the imidazolinium type such as di(hydrogenated tallow)dimethyl imidazolinium methylsulfate, 1 -ethylene-bis(2-tallow-1 -methyl) imidazolinium methylsulfate and the like;

3. Diamido quaternary ammonium salts such as: methyl-bis(hydrogenated tallow amidoethyl)-2-hydroxethyl ammonium methyl sulfate, methyl bi(tallowamidoethyl)-2- hydroxypropyl ammonium methylsulfate and the like;

4. Biodegradable quaternary ammonium salts such as N,N-di(tallowoyl-oxy-ethyl)-N,N- dimethyl ammonium methyl sulfate and N,N-di(tallowoyl-oxy-propyl)-N,N-dimethyl ammonium methyl sulfate. Biodegradable quaternary ammonium salts are described, for example, in U.S. Patents 4,1 37,180, 4,767,547 and 4,789,491 incorporated by reference herein.

Preferred biodegradable quaternary ammonium salts include the biodegradable cationic diester compounds as described in U.S. Patent 4,137,180, herein incorporated by reference.

(ii) Tertiary fatty amines having at least one and preferably two C₈-C₃₀, preferably C₁₂-C₂₂ alkyl chains. Examples include hardened tallow-di-methylamine and cyclic amines such as 1 -(hydrogenated tallow)amidoethyl-2-(hydrogenated tallow) imidazoline. Cyclic amines which may be employed for the compositions herein are described in U.S. Patent 4,806,255 incorporated by reference herein.

(iii) Carboxylic acids having 8 to 30 carbons atoms and one carboxylic group per molecule. The alkyl portion has 8 to 30, preferably 12 to 22 carbon atoms. The alkyl portion may be linear or branched, saturated or unsaturated, with linear saturated alkyl preferred. Stearic acid is a preferred fatty acid for use in the composition herein. Examples of these carboxylic acids are commercial grades of stearic acid and palmitic acid, and mixtures thereof which may contain small amounts of other acids.

(iv) Esters of polyhydric alcohols such as sorbitan esters or glycerol stearate. Sorbitan esters are the condensation products of sorbitol or iso-sorbitol with fatty acids such as stearic acid. Preferred sorbitan esters are monoalkyl. A common example of sorbitan ester is SPAN 60 (ICI) which is a mixture of sorbitan and isosorbide stearates.

(v) Fatty alcohols, ethoxylated fatty alcohols, alkylphenols, ethoxylated alkylphenols, ethoxylated fatty amines, ethoxylated monoglycerides and ethoxylated diglycerides.

(vi) Mineral oils, and polyols such as polyethylene glycol.

These softeners are more definitively described in U.S. Patent 4,134,838 the disclosure of which is incorporated by reference herein. Preferred fabric softeners for use herein are acyclic quaternary ammonium salts. Di(hydrogenated)tallowdimethyl ammonium methylsulfate is most widely used for dryer articles of this invention. Mixtures of the above mentioned fabric softeners may also be used.

In addition, the composition according to the present invention may also contain a minor proportion of one or more adjuvants. Examples of adjuvants include emulsifiers, perfumes, colouring dyes, opacifiers, fluorescent whitening agents, bactericides, nonionic surfactants, anti-gelling agents such as nitrites or nitrates of alkali metals, especially sodium nitrate, and corrosion inhibitors such as sodium silicate.

The amount of each of these optional adjuvants preferably ranges from 0.05 to 5% by weight of the composition.

A particularly preferred optional adjuvant is a cationic, amphoteric or anionic fluorescent whitening agent as disclosed in EP-A-0,659,877, from page 9 to page 15, line 56.

The present invention also provides, as a third aspect, a method for the treatment of a textile article, in particular to improve its UPF, comprising applying, to a previously washed article, a fabric rinse composition comprising: a) 0.1 to 10, preferably 0.1 to 5% by weight of a UV absorber of formula (1), based on the total weight of the composition; b) 5 to 25%, especially from 10 to 20% by weight, based on the total weight of the composition, of a fabric care ingredient; and c) the remainder being substantially water.

Preferably, the fabric care ingredient is a fabric softener, a stain release or stain repellent ingredient or a water-proofing agent.

A preferred method for the treatment of a textile article, in particular to improve its UPF comprises applying, to the previously washed article, a rinse cycle fabric softener composition comprising: a) 0.05 to 5, preferably 0.1 to 1 .5% by weight of a UV absorber of formula (1), based on the total weight of the composition; b) 5 to 25, preferably 10 to 20% by weight of a cationic fabric softening agent, based on the total weight of the composition; and c) the remainder being substantially water.

The textile article treated according to the method of the present invention may be composed of any of a wide range of types of fiber such as wool, polyamide, cotton, polyester, polyacrylic, silk or any mixture thereof.

The method and composition of the present invention, in addition to providing protection to the skin, also increase the useful life of a textile article treated according to the present invention, for example by preserving its tear strength and/or its lightfastness.

The following Examples further illustrate the present invention.

Example 1 :

5 g of bleached cotton fabric are washed/rinsed in a linitest applying the following conditions:

Main wash:

Detergent dosage: 4 g/l ECE 77 (phosphate containing standard detergent which is free of fluorescent whitening and bleaching gents ) Liquor ratio: 1 :20

Duration: 15 minutes

Temperature: 25°C

Rinsing is carried out with tap water for 30 seconds and the spin dried.

Rinse bath:

Softener dosage: 1 ,66 g/l concentrated Esterquat or 5 g/l diluted DSDMAC

Liquor ration: 1 :40

Duration: 15 minutes

Temperature: 25^CC

The fabric is spin dried at 60°C; 1 and 3 wash cycles

The UPF of the dried softener treated goods are determined.

The UPF is determined by measurement of the UV light transmitted through the textile, using a double grating spectrophotometer fitted with an Ulbricht bowl. Calculation of UPF is conducted as described by B.L.Diffey and J.Robson in ). Soc. Cosm. Chem. 40 (1989), pp.

130-131.

The results are shown in Table 3:

The results in Table 1 and 2 clearly demonstrate the improvement of the UPF values of the cotton substrates treated with rinse compositions according to the present invention.

Claims

1. fabric rinse composition comprising a) 0.1 to 10 % by weight of a UV absorber selected from a hydroxyaryl-1 ,3,5-triazine of the formula

, wherein

R, is hydrogen; C,-C₄alkyl; C,-C₄ -Alkoxy; or halogen;

R₂ is mono-C^C^Ikylamino; di-C^-C^alkylamino; a radical of the formula ^Y N,₊ ^Y3 γ_

X is C₂-C₄alkylen;

Y Y₂ independently from each other are C C₄alkyl or C,-C₄alkyl which is substituted by halogen, cyano hydroxy or C,-C₄alkoxy; or Y, and Y₂ or Y, and Y₃ together with the nitrogen atom form a 5- to 7-membered heterocycle; Y₃ is hydrogen; C C₄alkyl; C₃-C₄alkenyl; or C,-C₄alkyl, C₃-C₄alkenyl which is substituted by cyano, hydroxy, C,-C₄alkoxy, phenyl or C,-C₄alkoxycarbonyl; or Y„ Y₂ and Y₃ together with the binding nitrogen atom form a pyrrolidine, piperidine or morpholine radical; A is the counter ion; b) 5 to 25% by weight, based on the total weight of the composition of a fabric care ingredient; and c) the remainder being substantially water.

2. A composition according to claim 1 of formula

(2) , wherein

R, is hydrogen or C,-C₅alkyl;

Y Y

R₂ is mono-C^C^Ikyla ino; di-C C₅alkylamino; a radical of the formula ¹ N⁺" ³ A^' ,

Y₂

X is C₂-C₄alkylen;

Y„ Y₂ and Y₃ independently from each other are Chal y!; and

A is as defined as in claim 1 .

3. A composition according to claim 1 or 2 wherein R, is hydrogen or C,-C₂alkyl.

4. A composition according to any one of claims 1 to 3 wherein

R₂ is di-C,-C₂alkylamino; N⁺(C,-C₂alkyl)₃-A-; N⁺(C,-C₂alkyl)₂CH₃-A^"; and

A is as defined as in claim 1.

5. A composition according to claim 4 wherein

R₂ is -N(CH₃)₃; -N(C₂H₅)₂; -N⁺(CH₃)₃ A; or -N⁺(C₂H₅)CH₃ A^".

6. A composition according to any one of claims 2 to 5 wherein

R, is hydrogen or methyl;

R₂ is -N(CH₃)₃; -N(C₂H_S)₂; -N⁺(CH₃)₃ A^'; or -N⁺(C₂H₅)CH₃ A^";

X is -CH₂CH₂-; or -CH₂-CH₂-CH₂-; and

7. A composition according to any of the preceding claims wherein

O^" O^"

A is selected from o=s=o ; o=s=o ; or I^".

OH H,C— O

8. A composition according to any of the preceding claims in which the fabric care ingredient is selected from cationic quaternary ammonium salts, tertiary fatty amines having at least one C₈-C_3Q alkyl chain, carboxylic acids having 8 to 30 carbons atoms and one carboxylic group per molecule, esters of polyhydric alcohols, fatty alcohols, ethoxylated fatty alcohols, alkyphenols, ethoxylated alkyphenols, ethoxylated fatty amines, ethoxylated monoglycerides and ethoxylated diglycerides.

9. A composition according to claim 8, wherein cationic quaternary ammonium salt fabric softener is selected from acyclic quaternary ammonium salts having at least two C₈ to C₃₀ alkyl or alkenyl chains , cyclic quaternary ammonium salts, diamido quaternary ammonium salts and biodegradable quaternary ammonium salts.

10. A composition according to claim 9, wherein acyclic quaternary ammonium salts correspond to formula

II

1 1. A composition according to claim 9, wherein acyclic quaternary ammonium salts correspond to formula

P C— R„

(4) (R₃)₃N — (CH₂)_β — OH , wherein

CH-0-C-R₄ O

each R₃ group is independently selected from C, to C₄ alkyl, hydroxyalkyl or C₂ to C₄ alkenyl groups; and each R₄ group is independently selected from C₈ to C₂₈ alkyl or alkenyl groups; and e is an integer from O to 5.

12. A composition according to claim 10, wherein the acyclic quaternary ammonium salt is di-(palmcarboxyethyl)-hydroxyethyl-methylammonium-methosulfate.

13. A composition according to claim 10, wherein the acyclic quaternary ammonium salt is selected from ditallowdimethyl ammonium methylsulfate, di(hydrogenated tallow)dimethyl ammonium methylsulfate, distearyldimethyl ammonium methylsulfate or chloride and dicocodimethyl ammonium methylsulfate.

14. A composition according to claim 8 or 9, in which the biodegradable quaternary ammonium salts are selected from N,N-di(tallowoyl-oxy-ethyl)-N,N-dimethyl ammonium methyl sulfate and N,N-di(tallowoyl-oxy-propyl)-N,N-dimethyl ammonium methyl sulfate.

15. A composition according to any of the preceding claims which also contains an adjuvant selected from an emulsifier, perfume, colouring dye, opacifier, fluorescent whitening agent, bactericide, nonionic surfactant, anti-gelling agent and corrosion inhibitor.

16. A method for the treatment of a textile article, comprising applying, to a previously washed article, a fabric rinse composition comprising a) 0.1 to 10% by weight of a UV absorber of formula (1 ), based on the total weight of the composition; b) 5 to 25% by weight, based on the total weight of the composition, of a fabric care ingredient; and c) the remainder being substantially water.

17. A method according to claim 18 in which the textile article treated is composed of wool, polyamide, cotton, polyester, polyacrylic, silk or any mixture thereof.

18. A method according to claim 18 or 19 in which the UPF value of the treated textile article is improved.

19. A method according to claim 18 or 19 in which the tear strength and/or the lightfastness of the treated textile article is improved.