Classifications

• • D—TEXTILES; PAPER
  • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
  • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
  • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
  • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
  • D06M13/395—Isocyanates
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G18/00—Polymeric products of isocyanates or isothiocyanates
  • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
  • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
  • C08G18/30—Low-molecular-weight compounds
  • C08G18/302—Water
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G18/00—Polymeric products of isocyanates or isothiocyanates
  • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
  • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
  • C08G18/40—High-molecular-weight compounds
  • C08G18/64—Macromolecular compounds not provided for by groups C08G18/42 - C08G18/63
  • C08G18/6415—Macromolecular compounds not provided for by groups C08G18/42 - C08G18/63 having nitrogen
  • C08G18/6446—Proteins and derivatives thereof
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G18/00—Polymeric products of isocyanates or isothiocyanates
  • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
  • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
  • C08G18/703—Isocyanates or isothiocyanates transformed in a latent form by physical means
  • C08G18/705—Dispersions of isocyanates or isothiocyanates in a liquid medium
  • C08G18/706—Dispersions of isocyanates or isothiocyanates in a liquid medium the liquid medium being water
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G18/00—Polymeric products of isocyanates or isothiocyanates
  • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
  • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
  • C08G18/72—Polyisocyanates or polyisothiocyanates
  • C08G18/80—Masked polyisocyanates
  • C08G18/8003—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen
  • C08G18/8006—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32
  • C08G18/8041—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32 with compounds of C08G18/3271
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G18/00—Polymeric products of isocyanates or isothiocyanates
  • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
  • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
  • C08G18/72—Polyisocyanates or polyisothiocyanates
  • C08G18/80—Masked polyisocyanates
  • C08G18/8061—Masked polyisocyanates masked with compounds having only one group containing active hydrogen
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G18/00—Polymeric products of isocyanates or isothiocyanates
  • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
  • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
  • C08G18/72—Polyisocyanates or polyisothiocyanates
  • C08G18/80—Masked polyisocyanates
  • C08G18/8061—Masked polyisocyanates masked with compounds having only one group containing active hydrogen
  • C08G18/8064—Masked polyisocyanates masked with compounds having only one group containing active hydrogen with monohydroxy compounds

Definitions

• the polyisocyanate is a polymethylene polyphenyl isocyanate or a poly(isocyanato phenyl)methane, applied in an organic solvent and the water cure is effected by immersing the treated wool in warm water.
• This invention relates to an improved composition and process for treating wool and more particularly it relates to an improved composition and process for treating wool and similar proteinaceous materials so as to render them substantially shrink proof.
• a further object of the present invention is to provide an improved process for treating wool and other proteinaceous materials so as to render them substantially permanently shrinkproof, which process is easily and economically carried out.
• the present invention includes a process for treating a proteinaceous material which comprises contacting the proteinaceous material with a polymerizable treating solution comprising a polyaryl polyisocyanate containing at least three aryl groups and an average of at least three isocyanate groups, a portion of which isocyanate groups may be modified by-reaction with an alcohol, thioalcohol, organic acid, amine or amide, and, thereafter, curing the thus-contacted materialwith water.
• the proteinaceous materials, such as proteinaceous textiles, treated in accordance with this process are found to be durably shrink resistant, even after repeated washings in hot water. Additionally, the hand or feel of the thus-treated fabric is generally found to be substantially unchanged from that of the untreated material.
• the proteinaceous materials to be treated are proteinaceous textile materials, and particularly proteinaceous textiles which undergo shrinking during normal laundering operations.
• These textile materials may be in various forms, including yard goods, as well as various finished articles, such as articles of clothing, including coats, sweaters, socks, shirts, trousers, skirts, and the like.
• the process of the present invention has been found to be particularly applicable in the treatment of wool. Accordingly, hereinafter, primary reference will be made to wool as being the preferred proteinaceous material.
• the proteinaceous materials treated may be admixed with other non-proteinaceous materials as in various fiber blends with synthetics or other natural fiber materials or they may be in the form of a so-called multiply fabric wherein the proteinaceous fabric is bonded to a fabric of some other material, such as acetate, rayon,
• the material is impregnated with a solution which comprises, as the essential shrinkproofing component, a polyaryl polyisocyanate compound, either as such or modified by reaction with an alcohol, thio alcohol organic acid, amine or amide.
• a solution which comprises, as the essential shrinkproofing component, a polyaryl polyisocyanate compound, either as such or modified by reaction with an alcohol, thio alcohol organic acid, amine or amide.
• Suitable compounds may be characterized generally as being selected from the .group consisting of and s I N O O N Rm N C 0 CY2 CY2'i- I I I R R n R s I N C 0 NC Rm I 1 Y9 C J l- I R t R wherein n is a number having an average value of at least 1 and is generally from 1 to 4; t is a number from 2 to 4; p is a number from 0 to 2; p is 0 or 1; t-I-p has an average value of at least 3 and is generally from 3 to4; t+p+p' is 4; m is a number from 0 to 1; R is selected from the group consisting of halogen, hydrogen, alkyl and alkoxy; y is selected from the group consisting of hydrogen, alkyl and phenyl; R is selected from the group consisting of OX, SX,
• the shrinkproofing compositions used may be a mixture of one or more of the above compounds or other similar compound which fall within the generic formulas which have been given. Often, such mixtures will be the natural result of the preparation of the compositions, which preparations may give a statistical distribution of the possible products. Such mixtures may be mixtures of various polymethylene polyphenyl isocyanates, mixtures of various poly(isocyanato phenyl)methanes, or mixtures of both polymethylene polyphenyl isocyanates and poly(isocyanatophenyl)methanes.
• the shrinkproofing component as has been described is dispersed or dissolved in a suitable solvent.
• a suitable solvent any solvent, in which the isocyanate material will dissolve without decomposition may be used, in many instances, the aromatic organic solvents, such as benzene, toluene, xylene, and the like, are preferred. Additionally, halogenated aliphatic solvents, such as trichloroethylene, perchloroethylene, carbon tetrachloride, methylene chloride, and the like, have also been found to be extremely useful.
• the solvents may be classified generally as benzene, substituted benzenes containing 1-3 lower alkyl groups of 1-6 carbon atoms each and halogenated lower alkyls containing 1-6 carbon atoms and 1-8 halogens.
• the shrinkproofing component is dispersed or dissolved in the solvent in an amount suflicient to provide the desired resin add-on on the proteinaceous material when the material is impregnated with the solution.
• Concentrations within the range of about 0.5 to about 50% by weight of the solvent composition are typical, but in many instances, higher concentrations are also suitable, up to the maximum solubility of the isocyanate material in the solvent used. Typical of such higher concentrations which may be used are those of 80 to 90% by weight of the solvent composition, or even higher, in those instances where the isocyanate material used is miscible in substantially all proportions with the solvent.
• the polyisocyanate material is dissolved in the solvent in an amount sufiicient to provide the desired concentration in the impregnating solution.
• an unmodified polyisocyanate such as polymethylene polyphenylisocyanate or tris(isocyanatophenyl)methane
• the polyisocyanate material is dissolved in the solvent in an amount sufiicient to provide the desired concentration in the impregnating solution.
• the unmodified polyisocyanate may be dissolved in several times its own weight of solvent and to this mixture the modifying material, such as an alcohol, thioalcohol, organic acid, amine, or amide is added, in an amount sufiicient to react with the unmodified polyisocyanate and effect the modification desired.
• the reaction mixture may also contain a suitable catalyst, such as a polyalkyl amine.
• a suitable catalyst such as a polyalkyl amine.
• the amount of modifying agent added is sufficient to react with from about 5% to about 70% of the isocyanate groups present, and preferably is sufficient to react With from about to 35% of the isocyanate groups.
• the amount of modifier used is such that in the resulting modified isocyanate there are at least two unmodified isocyanate groups.
• reaction is substantially complete, additional solvent may be added to the reaction mixture to obtain the impregnating solution having the desired concentration.
• the modified polyisocyanates may be prepared separately and thereafter dissolved in the solvent in appropriate amounts to form the impregnating solution, as is done with the unmodified polyisocyanate.
• the proteinaceous material such as a wool textile material
• the polymerizable shrinkproofing solution prepared as indicated hereinabove, using any convenient means.
• the wool may be immersed or padded in the treating solution and the fabric then passed through squeeze rolls to remove excess solution.
• the treating solution may be applied to the material by spraying, rather than by immersion.
• Other suitable application techniques as are known to those in the art, may also be used.
• the proteinaceous materials After the proteinaceous materials have been impregnated with the solution, they are preferably dried so as to remove the solvent from the material. Desirably, the impregnation is carried out so that the treated proteinaceous material has a resin add-on within the range of about 1 to about by weight of the material.
• the treating solution is maintained at a temperature within the range of about 10 centigrade to the boiling point of the solvent used, e.g., centigrade for perchloroethylene, and preferably is Within the range of about 20 centigrade to about 30 centigrade during the impregnation step.
• the impregnated material is dried, preferably in an oven, at a temperature within the range of about 20 centigrade to the boiling point of the solvent used, 'with temperatures within the range of about 65 centigrade to about centigrade being preferred.
• the thus-treated fabric is then cured in water.
• the treated proteinaceous material is preferably immersed in water and maintained in the water until the curing is complete.
• the time to effect the desired cure of the polyisocyanate material with which the proteinaceous textile is impregnated varies with the temperature at which the cure is effected. Accordingly, it is desirable that the water used is at an elevated temperature, temperatures within the range of about 40 centigrade to about 100 centigrade being typical, with temperatures within the range of about 80 centigrade to about 94 centigrade being preferred, When carrying out the water cure at these temperatures, curing times within the range of about 1 hour to about 1 minute are typical, with times of 30 minutes to 2 minutes being preferred.
• the Water cure of the polyisocyanate impregnant may be carried out at room temperature, i.e., about 20 centigrade. Under such conditions, the curing time may be as long as several days, e.g., 48 hours. There is, however, some indication that the full shrinkproofing effectiveness of the polyisocyanate compositions may not be attained when the water cure is carried out under these low temperature conditions. Moreover, it has been found that low temperature curing techniques, and particularly those carried out below about 75 centigrade, may not impart to the treated fabric the desired degree of durability to dry cleaning solvents, such as trichloroethylene.
• the water cure of the polyisocyanate impregnant may be effected by substantially saturating the impregnated proteinaceous material with water and thereafter, completing the polymerization or cure of the polyisocyanate by heating the water wet, substantially saturated material at an elevated temperature.
• curing temperatures within the range of about 66 centigrade to about 177 centigrade for periods of about 30 minutes to about 1 minute are typical, with temperatures within the range of about 107 to about centigrade for periods of 10 minutes to about 3 minutes being preferred.
• the material is then dried to remove any water which may remain.
• the later described curing process i.e., water impregnation of the treated fabric, followed by heating at an elevated temperature, the curing and drying of the fabric is effected substantially simultaneously.
• the water used to carry out the polymerization or cure of the polyisocyanate impregnant in the textile material is desirably slightly alkaline.
• Typical pH values for the curing water are within the range of about 7.5 to 9. Where the pH of the curing water is below these values, it may be adjusted by adding thereto an alkaline material, such as an alkali metal bicarbonate.
• the curing water may also contain small amounts of a suitable wetting agent, to insure more thorough and rapid wetting of the impregnated material.
• Typical wetting agents which may be used are nonionics, such as the polyalkylene ethers and anionics such as alkyl aryl sulfonates and sulfates. These materials are typically present in amounts within the range up to about 1% by weight of the treating water, amounts within the range of about 0.05 to about 0.2% being preferred.
• the process of the present invention may be carried out on proteinaceous materials in various forms, including yard goods, finished articles, such as sweaters and the like, as well as on the unspun fiber or the yarn itself.
• proteinaceous textile materials such as wool
• the shrink resistance is retained by the treated fabric even after numerous washings in hot water and that the hand and feel of the treated materials are not substantially different from those of untreated material.
• the shrinkproof finish is durable to dry cleaning and is found to impart dimensional stability to the fabric. It also facilitates dying and improves dye fastness.
• a textile treating solution was prepared by dissolving a commercial polymethylene polyphenylisocyanate having a viscosity of 250 centipoises at 25 centigrade and an NCO equivalent weight of 133.5 in benzene to form a solvent solution containing about 7% by weight of the polyisocyanate. Wool fabric was padded through this solution so as to impregnate the fabric and thereafter, the fabric was dried in an oven at a temperature of about 40 C. The treated wool was then immersed in water, which was at a temperature of about 60 C.
• Example 2 The procedure of Example 1 was repeated with the exception that the solvent solution prepared was a trichlo- 12 roethylene solution containing 4% by weight of the po yisocyanate. The fabric treated with this solution had a resin add-on of 6.7% and gave an area shrinkage of only 3.2% after being subjected to the cure conditions and to the 5 hour wash, as in Example 1.
• the solvent solution prepared was a trichlo- 12 roethylene solution containing 4% by weight of the po yisocyanate.
• the fabric treated with this solution had a resin add-on of 6.7% and gave an area shrinkage of only 3.2% after being subjected to the cure conditions and to the 5 hour wash, as in Example 1.
• Example 3 The procedure of Example 1 was repeated with the exception that the treating solutions used were benzene solutions containing 1, 4, and 7% by weight respectively, of tris(isocyanatophenyl)methane.
• the fabrics treated with these solutions had resin add-ons of 3.0, 6.4 and 11.6% respectively, and gave area shrinkages after the five hour washing of 3.2, 2.0 and 2.3%, respectively.
• a textile treating composition was prepared by dissolving 50 parts of the polymethylene polyphenylisocyanate, as used in Example 1, in parts of toluene. To this solution were added 20 parts of l-octadecanol, and 0.5 parts of triethylamino catalyst. The resulting solution was stirred for a period of about 30 minutes while the temperature was maintained below about 40 centigrade. At the end of this time, it was found that all of the alcohol had reacted with the isocyanate to form an alcohol substituted polyisocyanate containing 0.2 moles of alcohol per mole equivalent of NCO group.
• Example 2 Thereafter, additional toluene was added to the reaction product to obtain a diluted treating solution containing about 6% by weight of the alcohol substituted polyisocyanate.
• This treating solution was padded onto a wool fabric, as in Example 1, and the treated fabric was dried.
• This material was then immersed in water at room temperature, the water containing 0.1% sodium bicarbonate and 0.1% of the nonionic wetting agent of Example 1.
• a wet pickup on the treated fabric of about 100% was obtained and the Wet fabric was then heated for five minutes at a temperature of about Centigrade to effect curing and drying of the fabric and obtain a resin add-on of 3.7%.
• the fabric was washed for five hours at 60 centigrade, and dried as in Example 1, and at the end of this time the area shrinkage of the fabric was found to be 1.3% and the fabric had a Gurley stiffness value of 33 milligrams.
• EXAMPLE 5 Additional treating solutions were formulated, using the procedure of Example 4 with the exception that five, fifteen and thirty parts by weight of the alcohol were used.
• the resulting alcohol substituted polyisocyanates formed contained 0.05, 0.15 and 0.30 mole of alcohol per mole equivalent of NCO.
• Wool fabric was treated with impregnating solutions containing 6% of these products and the treated fabric was cured and washed, as in Example 4.
• the area shrinkages obtained were 2.8%, 2.1% and 1.0%, respectively and the Gurley stiffness values were 46, 36 and 31 milligrams, respectively.
• Example 6 The procedure of Example 4 was repeated with the exception that the alcohol used was l-octanol in an amount of 9.6 parts by weight.
• the resulting alcohol modified polyisocyanate contained 0.2 mol of alcohol per mol equivalent of NCO. After curing and washing the treated wool fabric as in Example 4, the area shrinkage obtained was 4.53%.
• EXAMPLE 7 The procedure of Example 4 is repeated with treating solutions prepared by using the modifiers and polyisocyanates in the amounts shown in the following table. In each instance, the reaction temperatures and catalyst amounts are varied as necessary to obtain the indicated reaction products. With all of these treating solutions, the wool treated had an area shrinkage of less than about 10%. It is to be noted that in Section II of the table, the
• poly'isocyanate used is a 20% by weight solution of the isocyanate:
• J 1-1icosano1 30 tris(Isocyanatophenyl)methane. 185 1 K--- p-hydroxyphenylethanoL. do 920 0. 2 L. l-pentanethiol 11 .do 368 0. 5 M -Hydroxyphenyltetradecanoic acid. 7 ..do 19 2 N giphenyl amine 2 .do 184 0. 1 O. Licosanyl amine 3 do 46 0. 4 P N-phenyl benzamide 2 .do 28 0. 67 Q N-decyl dodecamide 3. 5 do 37 0. 5
• EXAMPLE 8 EXAMPLE 11 The procedure of Example 1 was repeated using a treating solution containing 4. 0% by weight of the polymethylene polyphenylisocyanate, as described in Example 1 and benzene. The treating solution was applied to a pair of worsted wool trousers which, after curing as in Example 1, were given five home launderings. The percentages of linear shrinkage which resulted from these washings, measured at the length of the leg, and the waist, and the width at the crotch, were 0.7, 2.5, and 0, respectively.
• EXAMPLE 9 The procedure of the preceding example was repeated using a treating solution containing 3% by weight of the polymethylene polyphenyl isocyanate and benzene. This treating solution was applied to a -wool knit sweater and the thus-applied polyisocyanate material was cured, using the procedure of Example 1. After ten home washings, the sweater showed the following linear shrinkages:
• Example 10 The procedure of Example 1 was repeated, using two treating solutions, one containing 3.7% by weight of the polymethylene polyphenylisocyanate and the second containing 2.4% by weight of the polymethylene polyphenylisocyanate.
• the first solution was used to treat a 55-45 percent blend of Dacron 1 polyester fiber and wool while the second was used to treat a 70-30 percent blend of wool and nylon.
• both of the treated fabrics were washed for 5 hours at degrees centigrade. Following these washings, it was found that the area shrinkage of the Dacron polyester fiber-wool 1 Registered trademark of E. I. du Pont de Nemours.
• Example 2 Using the procedure and treating solution of Example 1, a number of Wool fabric samples were impregnated and were then cured, using diiferent water temperatures and immersion times. Thereafter, the cured samples were extracted for 30 minutes in boiling trichloroethylene and then were washed for 10 hours at 60 degrees centigrade. Using this procedure, the following area shrinkages were obtained in these samples:
• Example 13 The procedure of Example 1 was repeated using different isocyanate materials at varying concentrations. These materials are similar to isocyanate materials of the present invention and are included to show the improvement obtained by the use of the materials of the present invention, containing at least two NCO groups. In each instance, the wool fabric impregnated with these treating solutions was cured and dried, and the area shrinkage was determined,
• the results oband X is selected from the group consisting of hydrogen, alkyl, alkylphenol, alkylphenoxyalkoxy and phenyl;
• a method of shrinkproofing a proteinaceous textile material which comprises (a) contacting the proteinaceous material to be treated with a polymerizable treating solution comprising a polyaryl polyisocyanate having the formula:
• R LR In R (I) Hm O NCO NGRm l YIYDI c R .i. i R' (II) wherein n is a number having an average value of at least 1 and is generally from 1 to 4; t is a number from 2 to 4; p is a number from 0 to 2; p is 0 to 1; t+p has an average value of at least 3 and is generally from 3 to 4; t+p+p' is 4; m is 0 or 1; R is selected from the group consisting of halogen, hydrogen, alkyl and alkoxy; Y is selected from the group consisting of hydrogen, alkyl and phenyl; R is selected from the group consisting of OX, SX, X,
• n is a number having an average value of at least 1 and is generally from 1 to 4; t is a number from 2 to 4; p is a number from 0 to 2; p is 0 or 1; t+p has an average 17 value of at least 3 and is generally from 3 to 4; t+p+p' is 4; m is 0 to 1; R is selected from the group consisting of halogen, hydrogen, alkyl and alkoxy; Y is selected from the group consisting of hydrogen, alkyl and phenyl; R is selected from the group consisting of OX, SX, X,
• t and XCN and X is selected from the group consisting of hydrogen, alkyl, alkylphenol, alkylphenoxyalkoxy and phenyl; which polyaryl polyisocyanate has been cured with water.

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• Chemical & Material Sciences (AREA)
• Health & Medical Sciences (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Medicinal Chemistry (AREA)
• Polymers & Plastics (AREA)
• Organic Chemistry (AREA)
• Engineering & Computer Science (AREA)
• Textile Engineering (AREA)
• Dispersion Chemistry (AREA)
• Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
• Polyurethanes Or Polyureas (AREA)

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Cited By (2)

• 1965
  • 1965-11-26 US US510028A patent/US3552910A/en not_active Expired - Lifetime
• 1966
  • 1966-11-24 GB GB52582/66A patent/GB1172384A/en not_active Expired
  • 1966-11-25 DE DE19661619079 patent/DE1619079A1/de active Pending
  • 1966-11-25 FI FI663131A patent/FI45467C/fi active
  • 1966-11-28 BE BE690306D patent/BE690306A/xx unknown
  • 1966-11-28 NL NL6616735A patent/NL6616735A/xx unknown

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