US2134001A

US2134001A - Mothproofing agent

Info

Publication number: US2134001A
Authority: US
Inventors: Lindley E Mills; William W Ailen
Original assignee: Dow Chemical Co
Current assignee: Dow Chemical Co
Priority date: 1937-10-16
Filing date: 1937-10-16
Publication date: 1938-10-25
Anticipated expiration: 1955-10-25

Description

Patented 25, 1938 UNITED STATES PAT:

Momnoommmm. v. N Lindley E. Mills and William w. Allen, Midland, Mich., assignors to The Dow Ohemical"Com-' pany, Midland, Mich., a corporation of Michigan No Drawing. Application October- 16, 1 937,: Serial No. 169,470 1 6 Claims. (Q1. 21-5) This invention relates to the protection of fur, hair, feathers, wool, etc., against the attack of moths. It is more particularly concerned with the mothproofing of fabrics.

Some agents heretofore employed for mothproofing are capable of attacking or staining the treated material. Other mothproofing products are highly volatile and impermanent in nature and are soon dissipated by vaporization from the material to which they are applied. Temporary protection has also been afforded by compounds which are soluble in water or soap solutions.

Some protecting agents such as the phenols and mercury and fluorine compounds are irritating to the skin and poisonous to human beings, while other common organic derivatives are objectionable because of their characteristic odor. A further disadvantage in the use of many of the common mothproofing compositions is the fact that the residues deposited in the treated article following evaporation of liquid constituents are crystalline and are soon dusted out of material treated therewith.

Among the objects of this invention is to provide a method for the protection of the aforementioned materials which will (1) give relatively permanent protection therefor against attack by moths, and (2) yield a protected product free from objectionable odor and toxicity to humans. Another object is to provide a composition comprising a volatile organic solvent having dissolved therein a mothproofing material which upon application to material susceptible to attack will prevent destruction thereof by moths without at the same time staining or otherwise injuring the material.

We have discovered that the foregoing advantages can be obtained by employing as mothproofing agents aryloxy alkylols having the formula wherein R represents an alkyl residue and X represents a hydrocarbon substituent containing at least 4 carbon atoms and selected from the group consisting of the alkyl and cycloalkyl radicals. When compounds of the above class, or mixtures thereof, are incorporated with a suitable organic solvent and particularly with a lower aliphatic alcohol, a liquid chlorinated hydrocarbon, or a volatile, highly refined petroleum fraction, and the solution so formed thereafter employed in the mothproofing of woolen fabrics and the like, the articles so treated are not stained or attackedthereby orcaused todevelop any distinctive odor.

Furthermore, these aryloxy alkylols are not appreciably dissipated from the fabric impregnated 5 therewith by contacting such fabric with water,

soap solutions, or petroleum distillate dry-cleaning fluids, or by volatilization or sublimation of the compound.

The aryloxy alkylols are, for the most part, odorless, water-white, viscous likuids. These compounds may he prepared by reacting a suitable phenol with a halo alcohol, e. g., ethylene bromohydrin, propylene chlorhydrin, mono-- chlorobutanol, etc.,- in the presence of a suitable 5 alkali, e. g., NaOH, KOH, etc. 'I'hesecompounds' may be dissolved in suitable solvents inamounts ranging between 1.0 and l0per cent by weight thereof and advantageously employed asmoth-g proofing compositions. We have found that solutions containing between about 3 and about 7- per cent by weight of such compounds'are satisfactory. I

In the numerous tests carried outtoe'stablish the utility of the aryloxy alkylols as mothproofing agents, the larvae of the black carpet beetle (Attagenus piceus) were employed. This insect is a common household pest attacking woolens, furs, and other materials' It is particularly destructive to fabrics used in upholstered furniture and to woolen carpets and rugs. It is more resistant and harder to control than the common case'- making clothes moth or tapestry moth, and con-' centrations of material found suitable for its control on fabrics have been shown to be more than adequate for the control of the latter species.

The following examples are illustrative of certain modes in which our invention may be. applied, but are not to be construed as limiting the same. 0

Example 1 A number of samples of white wool mohair cloth were saturated with solutions of 4-tertiarybutyl phenoxy ethanol in a volatile, highly refined petroleum distillate, thereafter pressed to remove excesses of the treating fluid, and allowed to dry. On each of a number of these samples five larvae of the black carpet beetle were placed and the sample folded over the larvae. These infested cloth samples were placed in a closed cardboard box and examined from time to time to determine the amount of feeding or other attack directly attributable to the beetle larvae. Simultaneous tests were made with larvae upon untreated samples of the mohair, both control and test samples being thereafter incubated at temperatures of 85-90 F. and at a relative humidity of 70-75 per cent. Examination of incubated samples impregnated with a 3 per cent 4-tertiary-butyl phenoxy ethanol solution showed that after three weeks there had been no feeding by the larvae. An average of two larvae were dead on each of the impregnated samples. In the case of the samples originally impregnated with a 5 per cent solution of the treating compound, there was no feeding by the larvae after three weeks incubation and an average of between 2 and 3 of the larvae were'dead on each test sample. The untreated controls showed a slight feeding by the larvae after one week, moderate feeding after two weeks, and heavy feeding at the end of three weeks incubation. Tests carried out over the same period upon mohair treated by immersion in the petroleum distillate alone showed moderate feeding by the larvae after one week, moderate feeding after two weeks, and heavy feeding at the end of a three-week period.

Example 2 Example 3 Dried samples of the impregnated woolen mohair were thoroughly washed in a 0.5 per cent solution of Ivory soap in water at a temperature of 40 C. After 20 minutes contact with'the soap solution, these test samples were rinsed in running water, and dried. It was found that upon infestation with the carpet beetle and two weeks incubation the samples originally impregnated with 5 per cent of i-tertiary-butyi phenoxy ethanol were substantially free from injury.

In the foregoing examples no staining of the impregnated cloth was observed and the fabric itself was not damaged by the aryloxy alkylol compound. The impregnated cloth in each instance was odorless, and even after prolonged weathering showed no discoloration. The preservative showed no tendency to crystallize out or to volatilize, from the fabric nor was the fabric greasy or oily to the touch.

Among other aryloxy alnlol compounds which may be similarly employed for the protection of fabrics and the like against attack by moths are: 2-tertiary-butyl phenoxy ethanol, 3-tertiaryamyl phenoxy ethanol, 4-normal-butyl phenoxyethanol, 3-secondary-amyl phenoxy ethanol, 4- secondary-butyl phenoxy propanol,- il-normal-amyl phenoxy propanol, 2-normal-hen1 phenoxy propanol, i-tertiary-butyl phenoxy butanol, 2-cyclohexyl phenoxy ethanol, i-cyclohexyl phenoxy ethanol, 2-cyclopentyl phenoxy ethanol, 3-cyclohexyl phenoxy propanol, i-cyclohex'yl phenoxy propanol, 2-cyclohexyl phenoxy butanol, etc.

Other solvents for the aryloxy alblols, forming solutions which may be employed as drycleaning agents, are liquid halogenated hydrocarbon compounds such as carbon tetrachloride, chloroform, ethylene chloride, trichloro-ethylene, chlorobenzene, and the like; hydrocarbon compounds, such as benzene, the lower paramn hydrocarbons, toluene, and the like; and the alcohols, such as ethyl and methyl alcohol, etc. Per, fumes, coloring agents, and the like, may be incorporated in the mothprooflng fluid, if desired.

When the aryloxy alkylcl compound is dissolved in a water-immiscible solvent, such composition may be employed as an emulsion with a soap or other wetting or emulsifying agent and water. Any of the cleansing agents and detergents common to the cleaning art may then be employed in conjunction therewith.

We claim:

1. A process for mothprooflng woolen fabrics and other materials subject to attack by moths which comprises treating such material with an aryloxy alkylol compound having the formula wherein R represents an alkyl residue and X represents a hydrocarbon substituent containing at least 4 carbon atoms and selected from the group consisting of the alkyl and cycloalkyl radicals.

2. A process for mothprooflng woolen fabrics and other materials subject to attack by moths which comprises treating such material with 4- tertiary-butyl phenom ethanol.

3. A process for mothprooflng woolen fabrics and other materials subject to attack by moths which comprises treating such materials with a composition comprising a-tertiary-butyl phenoxy ethanol dissolved in an organic solvent.

4. A process for mothprooflng woolen fabrics and other materials subject to attack by moths which comprises treating such materials with a composition comprising i-tertiary-butyl phenom ethanol dissolved in a light petroleum distillate.

5. A composition consisting of material liable to attack by moths having incorporated therein an aryloxy alkylol compound having the formula wherein R represents an alLvl residue and X represents a hydrocarbon substltuent containing at least 4 carbon atoms and selected from the group consisting of the alkyl and cylcloalkyl radicals.

6. A composition consisting of material liable to attack by moths having incorporated therein 4-tertiary-butyl phenoxy ethanol.

WILLIAM W. ALLEN.