US3079279A - Blends of imidazolidinones and aminoplasts and method for finishing cellulose containing textile material - Google Patents

Blends of imidazolidinones and aminoplasts and method for finishing cellulose containing textile material Download PDF

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Publication number
US3079279A
US3079279A US8686061A US3079279A US 3079279 A US3079279 A US 3079279A US 8686061 A US8686061 A US 8686061A US 3079279 A US3079279 A US 3079279A
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United States
Prior art keywords
employed
aminoplast
textile
resins
imidazolidinones
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Expired - Lifetime
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English (en)
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Jr William J Van Loo
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Wyeth Holdings LLC
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American Cyanamid Co
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Filing date
Publication date
Priority to NL276154D priority Critical patent/NL276154A/xx
Priority to BE615320D priority patent/BE615320A/xx
Priority to BE615426D priority patent/BE615426A/xx
Priority to NL275872D priority patent/NL275872A/xx
Priority to NL275422D priority patent/NL275422A/xx
Priority to BE614590D priority patent/BE614590A/xx
Priority to FR1317893D priority patent/FR1317893A/fr
Priority to BE614586D priority patent/BE614586A/xx
Priority to US86865A priority patent/US3185539A/en
Application filed by American Cyanamid Co filed Critical American Cyanamid Co
Priority to US86873A priority patent/US3091617A/en
Priority to US8686061 priority patent/US3079279A/en
Priority to FR889602A priority patent/FR1316792A/fr
Priority to FR889603A priority patent/FR1320260A/fr
Priority to FR890830A priority patent/FR1324983A/fr
Application granted granted Critical
Publication of US3079279A publication Critical patent/US3079279A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/39—Aldehyde resins; Ketone resins; Polyacetals
    • D06M15/423—Amino-aldehyde resins
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/30—Oxygen or sulfur atoms
    • C07D233/40—Two or more oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/30—Oxygen or sulfur atoms
    • C07D233/42—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B15/00—Preparation of other cellulose derivatives or modified cellulose, e.g. complexes
    • C08B15/10—Crosslinking of cellulose
    • 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
    • D06M13/402—Amides imides, sulfamic acids
    • D06M13/405—Acylated polyalkylene polyamines
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
    • Y10T428/2913—Rod, strand, filament or fiber
    • Y10T428/2933—Coated or with bond, impregnation or core
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
    • Y10T442/20—Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
    • Y10T442/2369—Coating or impregnation improves elasticity, bendability, resiliency, flexibility, or shape retention of the fabric
    • Y10T442/2393—Coating or impregnation provides crease-resistance or wash and wear characteristics

Definitions

  • This invention relates to a novel combination or blend of water soluble textile finishing materials, to the process for applying them to textile materials and to the textile materials finished therewith. More particularly, this invention relates to novel blends of imidazolidinones and aminoplast resins having particular utility in the finishing of cellulose containing textile materials and to the cellulose textile materials finished therewith.
  • R may be the same or different and are selected from the group consisting of hydrogen and lower alkyl such as methyl, ethyl, propyl and butyl and X is a member selected from the group consisting of O and S, is combined with an aminoplast resin and ap plied to cellulose containing textile materials in certain proportions, quite surprisingly an increase in wrinkle recovery is obtained with less fiber degradation when scorched subsequent to chlorine bleaching, when com- 3,979,279 Patented Feb. 26, 1953 pared to resin finishes resulting from the use of the individual resins alone.
  • the invention relates to the use of such compositions in the finishing of cellulosic textile materials and to the cellulosic textile materials so finished.
  • aminoplast aldehyde, and in particular formaldehyde, condensation products of polyfunctional compounds characterized by the presence of amino (-NH and imino (:NH) radicals in their molecules.
  • the aminoplast resins employable in the blends of this invention should be characterized by the presence of more than one methy-lol group (the result of condensation between a mole of formaldehyde and a labile hydrogen of an amino or imino radicals) to insure maximum effects in accordance with this invention.
  • cellulose containing textile material fibers, filaments, yarns, fabrics, whether woven or non-woven, knitted, felted or otherwise formed, containing at least 50% of cellulose fiber such as cotton, rayon, linen, hemp, jute or the like.
  • the cellulose fibers may be present in combination with other natural or synthetic fibers, such as wool, silk, acetate, nylon, polyester fibers, acyrlic fibers and the like.
  • the textile material is a formed, woven cotton fabric.
  • Lmidazolidinones having the formula above are prepared by reacting a urea with glyoxal or a substituted glyoxal by procedures to be described later.
  • a particular prefer-red class of imidazolidinones for use in this invention are those having the following general formula where the R values may be the same or different and are selected from the group consisting of hydrogen and lower alkyl such as methyl, ethyl, propyl and butyl and X is a member selected from the group consisting of oxygen and sulfur.
  • ureas which may be used are urea, l-methylurea, l-ethylurea, l-n-propylurea, l-n-butylurea, 1,3 d-imethylurea, 1,3 diethylurea, 1,3 di n propylurea, 1,3-di-n-butylurea, l-methyl-3-ethylurea, 1,3-di-secbutylurea, l-allylurea, 1,3-diallylurea, and the like.
  • glyoxal Illustrative of the glyoxals which may be used are glyoxal, methyl glyoxal, ethyl glyoxal, n-propyl glyoxall, isobutyl glyoxal, dimethyl glyoxal, methyl ethyl glyoxal, ethyl propyl glyoxal, and the like.
  • the ureas and glyoxals are normally reacted in stoichiometric amounts at room temperatures (about 20 to 30 C.) although slight excesses of either of the reactants may be employed.
  • This reaction may be carried out at temperatures from between 0 and (2., though preferably temperatures of about 20 to 70 C. are employed and of course the reaction may be carried out at atmospheric, subatmospheric or superatmospheric pressures for times sufficient to complete the reaction.
  • Completion of the reaction is normally indicated by complete usage of glyoxal as shown by glyoxal determinations in the reaction mixtures.
  • R and R are hydrogen with an appropriate lower alcohol under acidic conditions.
  • Any of the strong acids normally employed in the alkylation or etherification of amide-formaldehyde condensates or aminoplast resins may beemployed.
  • Such acids include the strong mineral acids, such as sulfuric, hydrochloric, nitric and the like. Normally, 'suiiicient acid is employed to produce a pH of below 4.
  • Suitable alcohols may be any of the lower alcohols such as methanol, ethanol, the propanols, the butanols and the like.
  • the reaction with an alcohol is carried out at a temperature of between and 50 C. and preferably at 15 C. to 30 C.
  • the aminoplast resins suitable for use in blend with the imidazolidinones referred to above are principally any of the aminoplast creaseproofin-g resins known to the textile finishing industry.
  • Such resins include the melamine-formaldehyde condensates as probably the single most important group.
  • Suitable melamine-formaldehyde condensates include those having from 1 to 6 moles of combined formaldehyde and from 1 to 6 moles of combined alcohol, such as, for example, methyl, ethyl and the like, although in addition to aliphatic monohydric alcohols, polyhydric alcohols and ether alcohols are also contemplated. Examples of such resins and how they are prepared may be found in US. Patent No. 2,197,357 and US.
  • creaseprooiing resins are fully water soluble and essentially monomeric potentially thermosetting materials.
  • examples of such materials include tris(methoxymethyl) melamine, tris(methoxymethyDdimethylol melamine, hexakis(methoxyrnethyl) melamine and the like.
  • Urea-formaldehyde condensates are contemplated, such as dimethylol urea, alkyla ted dimethylol urea such as methylated dimethylol urea, dimethylol ethylene urea, dimethylol 1,2-propylene urea, dimethylol 1,3-propylene urea and other related homologous compounds. Additionally the formaldehyde condensates of dicy'andiamide, biuret and the like are contemplated, as are the Water soluble formaldehyde condensates of thiobisamides described in US. latent No. 2,887,408.
  • Guanamine-formaldehyde condensates as for example, those described in U.S. Patent No. 2,887,409 including the formaldehyde condensates of methoxyacetoguanaminc, .ethoxyacetoguanamine, tertiary butoxy acetoguanamine andlthc like are contemplated.
  • Urons such as, for example, N,N-bis(methoxymethyl) uron and variousother and closely related compounds such as are described in US. Patent No. 2,373,135 are contemplated. Additionally, tetrahydrotriazohes such as tetrahydro-S-(beta-hydroxyethyl)-- triazone and related compounds that are described in U.S Patent No. 2,304,624 are contemplated.
  • exemplary creaseprooiing resins may be employed singly or in combination with each other and with other creaseproofing resins known to those skilled in the art, in accordance with the present invention.
  • imidazolidinones and the aminoplast resins or mixtures of imidazolidinones and aminoplast resins must be employed in relativearnounts in 100 parts of resin solids of between from about 20 to about 80% of the .imidazolidiuone andfrom about 80 to about 20% of the aminoplast resin.
  • imidazolidinone to aminoplast constitutes the range on a Weight basis in which the effects of the novel-'- blend of this invention are demonstrable.
  • novel resinous composition of this invention containing the imidazolidinones and aminoplasts in the aboveclescribed relative proportions may be applied to cellulosic textile materials by any of the conventional techniques such as immersion, padding, spraying and the like followed Where necessary by squeezing, hydroextraction or similar processes in order to aifix the desired amount of solids on the fabric.
  • the method of application should be such that from about 1 to about 25% and in some instances higher amounts of the product of this invention based on the weight of the fabric are deposited thereon. Within certain limits, the amount of agent applied depends upon the particular type of fabric being treated. Thus, when treating fabric consisting of fibrous cellulosic materials, the concentration of the order of about 1 to 25% and more particularly from 3 to 10% solids, based on the dry weight of the fabric, may be employed.
  • the catalyst or accelerator employed is an acidic type catalyst and may be a free acid, acid salt, alkanolamine salt, metal salt and the like of the type well known to thosein the textile finishing art.
  • concentration of catalyst employed may range from about 0.1 to about 25% .or'
  • the material is subject to drying and curingoperations in order to eifec't Wrinkle resistance and shrinkage control thereon.
  • the drying and curing operation may be carried out in a single step or in separate steps.
  • the temperatures at which the drying and curing operations are eifected vary widely and are influenced to some extent by the type of catalyst employed. Normally, the range of temperature extends from about F. to about 450 F. or even higher.' Generally speaking, the time of the drying and/or curing operation is inversely proportional to the temperatures employed and of course is influenced by whether or not separate or combined drying and curing steps are employed.
  • a time of from about one minute to about 10 minutes may be employed at temperatures from 450 to- 250 F., respectively.
  • curing times of the order of 5 minutes to about /4 minute at a temperature of from between 250 and 450 F., respectively have been successfully employed.
  • resins referred to hereinafter as A through F correspond as set forth below to the following materials:
  • the prepared solutions numbered 1 through 11 were applied to unmercerized 80 x 80 cotton percale by padding 36 x 16 inch swatches through a two roll micro-set padder approximating 85% wet pick-up on the fabric, equal to 5% resin solids on the weight of the fabric (owi).
  • Scorched tensile strength tests were performed initially and also after five sodium hypochlorite washes in accordance with the American Association of Textile Chemists and Colorists Tentative Test Method 92-1958. Results are also shown in Table I.
  • thermosetting resinous components may be employed as Well as various thermo-plastic textile finishing resinous compositions of the type normally employed to modify hand and the like.
  • additional materials may be employed as enhance softnesstullness, firmness, draping qualities, water repellency, fire retardance and the like, as well known to "those skilled in the art of textile finishing, without departing-from the spirit and scope of this invention.
  • composition comprising a compound of the formula:
  • R-N-GN-R1 R4 G B2 0B3 where X is a member selected from th group consisting of O and S, the Rs are selected from the group consisting ofhydrogen, methyl, ethyl, propyl and butyl and an iamin'oplast, said compound and said aminoplast being present in said composition in relative amounts by weight of from 4:1 to 1:4, respectively.
  • X is a member selected from the group consisting of O and S
  • the Rs are selected from the group consisting of hydrogen, methyl, ethyl, propyl and butyl and an aminoplast, said compound and said aminoplast being present in said solution in relative amounts by weight of from 4:1 to 1:4, respectively.
  • a method for finishing cellulose containing textile materials to impart wrinkle resistance with minimum loss in tensile strength which comprises applying thereto a composition comprising a compound of the formula:
  • X is a member selected from the group consisting of O and S
  • the Rs are selected from the group consisting of hydrogen, methyl, ethyl, propyl and'butyl, an aminoplast and a curing accelerator for said compound and said aminoplast, and thereafter subjecting the material to heat to cure said composition to a water insoluble state, said compound and said aminoplast being present in said composition in relative amounts by Weight of from 4:1 to 1:4, respectively.
  • a method for finishing cellulose containing textile material which comprises applying thereto a composition comprising a compound of the formula:
  • X is a member selected from the group consisting of O and S
  • the Rs are selected from the group consisting of hydrogen, methyl, ethyl, propyl and butyl
  • an aminoplast and a curing accelerator for said compound and said aminoplast said compoundand said aminoplast being applied in an amount of between 1% and 15% based on the dry weight'of the textile material and thereafter subjecting the material to heat to cure said composition to a water insoluble state, said compound and said aminoplast being present in said composition in relative amounts by weight of from 411 to 1:4, respectively.
  • Cellulose containing textile material characterized by Wrinkle resistance and minimum tensile strength loss when scorched subsequent to chlorine bleaching having thereon and cured to a'water insoluble state a composition comprising a compound of theformula:
  • X is a member selected from the group consisting of O and S
  • the Rs are selected from the group consisting of'hydrogen, methyl, ethyl, propyl and butyl and an aminoplast, said compound and said aminoplast being present in said composition in relative amounts by weight of from 4:1 to 1:4, respectively.
  • R4C-(EB5 where X is a member selected from the group consisting of O and S, the Rs are selected from the group consisting of hydrogen, methyL'ethyl, propyl and butyl and an aminoplast, said compound and saidaminoplast being present in said composition in relative amounts by weight of from 4:1 to 1:4, respectively.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Textile Engineering (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • Materials Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
US8686061 1961-02-03 1961-02-03 Blends of imidazolidinones and aminoplasts and method for finishing cellulose containing textile material Expired - Lifetime US3079279A (en)

Priority Applications (14)

Application Number Priority Date Filing Date Title
BE615426D BE615426A (en, 2012) 1961-02-03
BE615320D BE615320A (en, 2012) 1961-02-03
NL275422D NL275422A (en, 2012) 1961-02-03
BE614590D BE614590A (en, 2012) 1961-02-03
FR1317893D FR1317893A (en, 2012) 1961-02-03
BE614586D BE614586A (en, 2012) 1961-02-03
NL276154D NL276154A (en, 2012) 1961-02-03
NL275872D NL275872A (en, 2012) 1961-02-03
US86865A US3185539A (en) 1961-02-03 1961-02-03 Process of treating cellulose textiles with certain alkylenebis(n-carboxamides) and products produced therefrom
US86873A US3091617A (en) 1961-02-03 1961-02-03 Process for preparing 4, 5-dialkoxy-1, 3-dialkyl-2-imidazolidinones
US8686061 US3079279A (en) 1961-02-03 1961-02-03 Blends of imidazolidinones and aminoplasts and method for finishing cellulose containing textile material
FR889602A FR1316792A (fr) 1961-02-03 1962-03-01 Perfectionnements concernant la préparation de composés hétérocycliques
FR889603A FR1320260A (fr) 1961-02-03 1962-03-01 Agents de finissage de textiles
FR890830A FR1324983A (fr) 1961-02-03 1962-03-13 Nouveaux agents de finissage de textiles

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US8686061 US3079279A (en) 1961-02-03 1961-02-03 Blends of imidazolidinones and aminoplasts and method for finishing cellulose containing textile material

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US3079279A true US3079279A (en) 1963-02-26

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US (1) US3079279A (en, 2012)
BE (4) BE614590A (en, 2012)
FR (1) FR1317893A (en, 2012)
NL (3) NL276154A (en, 2012)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3260565A (en) * 1961-02-03 1966-07-12 American Cyanamid Co Novel imidazolidinones and their use as textile finishing agents
US3376101A (en) * 1963-10-22 1968-04-02 Agriculture Usa Process of modifying cellulosic textiles with glyoxal-biscarbamate reaction products
US3377249A (en) * 1966-08-04 1968-04-09 Deering Milliken Res Corp Soil release of polyester containing textiles through treatment with aminoplast resins in conjunction with acrylic emulsion polymers containing at least 20% acid calculated as acrylic acid
US3442905A (en) * 1966-09-08 1969-05-06 American Cyanamid Co N-methylol-n'-substituted-4,5-dihydroxy-2-imidazolidinones
US3472867A (en) * 1966-02-20 1969-10-14 Us Navy 4,5-dihydroxy,4,5-dimethoxy and 4,5-diethoxy 2-nitriminoimidazolidines
US3899469A (en) * 1967-10-24 1975-08-12 Ciba Geigy Ag Process for the manufacture of new condensates
US3911181A (en) * 1968-09-27 1975-10-07 American Cyanamid Co Permanent press textile finish
US4295846A (en) * 1980-03-18 1981-10-20 Basf Aktiengesellschaft Process for the production of formaldehyde-free finishing agents for cellulosic textiles and the use of such agents
US6103898A (en) * 1997-10-02 2000-08-15 Basf Aktiengesellschaft Preparation of cyclic urea derivatives
US6265589B1 (en) * 1996-12-30 2001-07-24 Basf Aktiengesellschaft Mixtures of alkylated methylolated 4,5-dihydroxy-imidazolidin-2-ones

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1237102B (de) * 1963-08-31 1967-03-23 Basf Ag Verfahren zur Herstellung von N, N'-(1, 2-Dihydroxyaethylen)-bis-carbonsaeureamiden durch Umsetzung von ungesaettigten Carbonsaeureamiden mit Glyoxal

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2339203A (en) * 1941-08-30 1944-01-11 American Cyanamid Co Treatment of cellulosic textile material
US2602018A (en) * 1949-11-22 1952-07-01 Beer Leo Monomethylol dimethyl hydantoin and dimethylol urea to shrinkproof and creaseproof cellulose fabrics
US2613210A (en) * 1950-09-13 1952-10-07 Rohm & Haas Methylene-bis-2-imidazolidones
US2876062A (en) * 1953-09-03 1959-03-03 Phrix Werke Ag Process of crease-proofing cellulose fibers and fabrics by applying ureaformaldehyde-glyoxal reaction products

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2339203A (en) * 1941-08-30 1944-01-11 American Cyanamid Co Treatment of cellulosic textile material
US2602018A (en) * 1949-11-22 1952-07-01 Beer Leo Monomethylol dimethyl hydantoin and dimethylol urea to shrinkproof and creaseproof cellulose fabrics
US2613210A (en) * 1950-09-13 1952-10-07 Rohm & Haas Methylene-bis-2-imidazolidones
US2876062A (en) * 1953-09-03 1959-03-03 Phrix Werke Ag Process of crease-proofing cellulose fibers and fabrics by applying ureaformaldehyde-glyoxal reaction products

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3260565A (en) * 1961-02-03 1966-07-12 American Cyanamid Co Novel imidazolidinones and their use as textile finishing agents
US3376101A (en) * 1963-10-22 1968-04-02 Agriculture Usa Process of modifying cellulosic textiles with glyoxal-biscarbamate reaction products
US3472867A (en) * 1966-02-20 1969-10-14 Us Navy 4,5-dihydroxy,4,5-dimethoxy and 4,5-diethoxy 2-nitriminoimidazolidines
US3377249A (en) * 1966-08-04 1968-04-09 Deering Milliken Res Corp Soil release of polyester containing textiles through treatment with aminoplast resins in conjunction with acrylic emulsion polymers containing at least 20% acid calculated as acrylic acid
US3442905A (en) * 1966-09-08 1969-05-06 American Cyanamid Co N-methylol-n'-substituted-4,5-dihydroxy-2-imidazolidinones
US3488701A (en) * 1966-09-08 1970-01-06 American Cyanamid Co Use of n-methylol-n'-substituted-4,5-dihydroxy - 2-imidazolidinones as textile finishing agents
US3899469A (en) * 1967-10-24 1975-08-12 Ciba Geigy Ag Process for the manufacture of new condensates
US3911181A (en) * 1968-09-27 1975-10-07 American Cyanamid Co Permanent press textile finish
US4295846A (en) * 1980-03-18 1981-10-20 Basf Aktiengesellschaft Process for the production of formaldehyde-free finishing agents for cellulosic textiles and the use of such agents
US6265589B1 (en) * 1996-12-30 2001-07-24 Basf Aktiengesellschaft Mixtures of alkylated methylolated 4,5-dihydroxy-imidazolidin-2-ones
US6103898A (en) * 1997-10-02 2000-08-15 Basf Aktiengesellschaft Preparation of cyclic urea derivatives

Also Published As

Publication number Publication date
BE614590A (en, 2012) 1900-01-01
BE615320A (en, 2012) 1900-01-01
NL275422A (en, 2012) 1900-01-01
BE615426A (en, 2012) 1900-01-01
BE614586A (en, 2012) 1900-01-01
FR1317893A (en, 2012) 1963-05-08
NL275872A (en, 2012) 1900-01-01
NL276154A (en, 2012) 1900-01-01

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