US3590100A - Methods of producing and applying textile finishes and finishes produced by such methods - Google Patents
Methods of producing and applying textile finishes and finishes produced by such methods Download PDFInfo
- Publication number
- US3590100A US3590100A US3590100DA US3590100A US 3590100 A US3590100 A US 3590100A US 3590100D A US3590100D A US 3590100DA US 3590100 A US3590100 A US 3590100A
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- United States
- Prior art keywords
- formaldehyde
- finishes
- urea
- reaction
- carbamate
- Prior art date
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/06—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D239/08—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine 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 directly attached in position 2
- C07D239/10—Oxygen or sulfur 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
- C07D233/32—One oxygen atom
-
- 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
-
- 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
-
- 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
-
- 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
- Y10T442/2549—Coating or impregnation is chemically inert or of stated nonreactance
- Y10T442/2574—Acid or alkali resistant
Definitions
- This invention relates to the finishing of fabrics, particularly cotton fabrics and cotton polyester blends so as to make them wrinkle and crush resistant, resistant to scorching and yellowing and capable of being laundered with the use of hypochlorite bleaching and acid sours in the rinse without suffering any deleterious effects, including substantial loss in tensile strength.
- the invention is particularly concerned with such finishes and methods of producing them.
- carbamate finishes are quite volatile and have a tendency to sublime on drying and even in storage. For this reason, they do not lend themselves well to permanent press or delayed curing processes.
- a garment made from uncured fabric treated with a conventional carbamate finish may 3,590,100 Patented June 29, 1971 lose most of its finish by sublimation before the garment is given the final processing.
- An object of the present invention is the provision of finishes which will have all the advantages of carbamate finishes but which will not have any drawbacks of these finishes.
- Another object is to eliminate the disadvantages of excessive formaldehyde and volatility in the processing of carbamate finishes.
- methylol derivatives of ethyl and methyl carbamate will completely volatize when exposed to temperatures of about 200 F. However, when they are further reacted With ethylene or propylene urea between 50%60% of the reaction product does not volatize.
- methylol derivatives of methyl, ethyl, propyl, hydroxy ethyl, methoxy ethyl and butyl carbamate are further reacted with glyoxal and urea, the resulting product does not volatilize even when exposed to temperatures of 300 F. for 30 minutes.
- the amount of formaldehyde may vary from 2 to 2.5 moles, the preferred amount being 2.25 moles.
- the pH must be adjusted to about 10 by the use of an alkali, for example, sodium hydroxide, potassium hydroxide, sodium carbonate, etc.
- Reaction is continued for about 1' /2 hours at 10 pH. It was found to be of importance that the pH should not drop below 9.5.
- the degree of methylolation is usually between and The reaction temperature is about F. to F.
- the resulting product is cooled to 120 F. and pH is adjusted to 4.0 by the use of maleic acid, citric acid, tartaric acid or hydrochloric acid. Maleic acid is preferred.
- the product is held at a pH of 4.0 at 120 F. for about one hour.
- reaction takes place with glyoxal and urea
- the pH is adjusted to from 4 to about 5 with caustic soda solution; the product is heated for 3 to 3%. hours and then cooled. No further adjustment is necessary.
- the free residual formaldehyde amounts to less than 1% and the product does not volatilize even at high temperatures.
- Experimentation with various amounts of glyoxal and urea has indicated that the amount of free formaldehyde decreases if a somewhat larger amount of urea in relation to glyoxal is used, namely for 1 mole glyoxal the urea should preferably be in the range of about 1.3 to 1.4 moles.
- EXAMPLE 1 75 gr. methyl carbamate (1 mole) are reacted with 183 gr. (2.25 moles) of 37% formaldehyde. 0.45 gr. sodium hydroxide are added to adjust the pH to 10.3. The reaction is continued for 1% hours at 158 P. Then the product is cooled to 113 F. About 1 gr. maleic acid is added to adjust the pH to 4.0. At this stage 1.71 moles of formaldehyde have been reacted, leaving 0.54 mole free formaldehyde.
- the resulting product is practically water white. It contains from 0.5% to 1.0% free formaldehyde and it will not volatilize at 300 F. for minutes. It is most effective as a finish for cotton fabrics and cotton polyester blend fabrics.
- EXAMPLE 2 103. gr. (1 mole) propyl carbamate are reacted with 183 gr. (2.25 moles) of 37% formaldehyde. 0.45 gr. sodium hydroxide are added to adjust the pH to 10.3. The reaction is continued for 2 hours at 158 F. Then the product is cooled to 113 F. 1 gr. maleic acid is added to change the pH to 4.0. At this stage 1.75 moles of formaldehyde have been reacted, leaving 0.5 mole of formaldehyde free.
- Sodium hydroxide is added to set pH at 5.0. 40.7 gr. (0.27 mole) of 40% glyoxal are added along with an amount of urea which may vary from 16.2 gr. (0.27 mole) to 21 gr. (0.35 mole). The reaction is continued for about 2 hours at about 175 F. The resulting product contains 0.5% to 1.0% free formaldehyde, it will not volatilize readily and it produces an excellent finish.
- EXAMPLE 4 119 gr. (1 mole) methoxy ethyl carbamate are reacted with 183 gr. (2.25 moles) of 37% formaldehyde. 1 gr. potassium hydroxide is added to adjust the pH to 10.2. The reaction is continued for 1% hours at F. Then the product is cooled to 113 F. Citric acid is added to set the pH at 4.0. At this stage 1.7 moles of formaldehyde have been reacted, leaving 0.55 mole of free formaldehyde.
- Fabrics which are those finished have excellent crush resistance and dimensional control as well as all other advantageous properties which are at least as good as those imparted to fabrics by prior art carbamate finishes. Furthermore, they have the additional advantages as compared to prior art carbamate finishes, that the amount of free formaldehyde is reduced to a negligible quantity and that the finish is non-volatile. Accordingly, the carbamate finishes of this invention can be used satisfactorily in permanent press processing.
- a finish for textile fabrics comprising a material resulting from a first reaction of one molar part of a carbamate compound selected from the group consisting of methyl carbamate, ethyl carbamate, propyl carbamate, methoxy-ethyl carbamate, hydroxy-ethyl carbamate and butyl carbamate with more than two molar parts of formaldehyde under reaction conditions of elevated temperature and alkaline pH and carrying forward said reaction as far as it will go and thence reacting all of the excess formaldehyde from said first reaction and in the presence of said product of said first reaction in a second reaction with a sufiicient amount of a compound selected from the group consisting of ethylene urea, propylene urea and combined glyoxal and urea at elevated temperatures and at a pH of from 5 to 9 and carrying forward said second reaction as far as it will go.
- a carbamate compound selected from the group consisting of methyl carbamate, ethyl
- a finish for textile fabrics as described in claim 1 the reactant used to react with said excess formaldehyde from said first reaction being combined glyoxal and urea in proportion of one molar part of glyoxal to at least 1.3 molar parts of urea.
Abstract
THE PROCESS OF PRODUCING CARBAMATE FINISHES BY REACTING AMONOCARBAMATE WITH FORMALDEHYDE IS CONTINUED BY REACTING FREE EXCESS FORMALDEHYDE LEFT AFTER THE REACTION WITH ETHYLENE UREA, PROPYLENE UREA OR GLYOXAL AND UREA TO SUBSTANTIALLY REDUCE THE FREE FORMALDEHYDE AND DIMINISH THE VOLATILITY OF THE FINISH.
Description
United States Patent 3,590,100 METHODS OF PRODUCING AND APPLYING TEX- TILE FINISHES AND FINISHES PRODUCED BY SUCH METHODS Herman G. Weiland, Westfield, N.J., assignor to Arkansas Company, Inc., Newark, NJ. No Drawing. Filed Jan. 24, 1967, Ser.- No. 611,268 Int. Cl. C08g 37/32; D06m 13/34 US. Cl. 260-849 3 Claims ABSTRACT OF THE DISCLOSURE The process of producing carbamate finishes by reacting amonocarbamate with formaldehyde is continued by reacting free excess formaldehyde left after the reaction with ethylene urea, propylene urea or glyoxal and urea to substantially reduce the free formaldehyde and diminish the volatility of the finish.
This invention relates to the finishing of fabrics, particularly cotton fabrics and cotton polyester blends so as to make them wrinkle and crush resistant, resistant to scorching and yellowing and capable of being laundered with the use of hypochlorite bleaching and acid sours in the rinse without suffering any deleterious effects, including substantial loss in tensile strength. The invention is particularly concerned with such finishes and methods of producing them.
There are many finishes of this type which are known in prior art, some producing better results than others, some being effective in one way while being deleterious in other respects. A study and testing of various existing finishes has shown that among the most efi'ective ones are the carbamate finishes. They are produced by reacting a monocarbamate, such as methyl carbamate, ethyl carbamate, propyl carbamate, butyl carbamate, methoxyethyl carbamate or hydroxyethyl carbamate with two or more moles of formaldehyde, the reaction taking place in an alkaline aqueous solution at a pH range of 9.5 to 10.5. :For example, dimethylol methyl carbamate is produced in accordance with the following formula showing the approximate molar proportions:
(1 mole) (2.25 Moles) ii") (free) CHaO-CN(CHOH) HOHO (0.8 moles) It is apparent that the reaction producing the methylol derivative does not go to completion and that an excess of formaldehyde remains present in the reaction product.
Practical experience has shown that this excess of formaldehyde consititutes a serious drawback of carbamate finishes which have otherwise good qualities, since they impart dimensional control and excellent wash and wear characteristics and still retain a soft hand, the hand being essentially unchanged. Excess formaldehyde has become a problem in finishing plants Where textiles are being treated with these finishes. In addition, residual amounts of formaldehyde are left in the goods even after drying and curing and can be detected not only in the fabric but sometimes even in the garment made from the fabric.
Another drawback of carbamate finishes is that they are quite volatile and have a tendency to sublime on drying and even in storage. For this reason, they do not lend themselves well to permanent press or delayed curing processes. For example, a garment made from uncured fabric treated with a conventional carbamate finish may 3,590,100 Patented June 29, 1971 lose most of its finish by sublimation before the garment is given the final processing.
An object of the present invention is the provision of finishes which will have all the advantages of carbamate finishes but which will not have any drawbacks of these finishes.
Another object is to eliminate the disadvantages of excessive formaldehyde and volatility in the processing of carbamate finishes.
I Other objects of the present invention will become apparent in the course of the following specification.
In the accomplishment of the objectives of the present invention it was found desirable to continue the reaction which produces the carbamates by further reacting the excess formaldehyde contained in the reaction with ethylene urea, propylene urea or glyoxal and urea.
It should be noted that the methylol derivatives of ethyl and methyl carbamate will completely volatize when exposed to temperatures of about 200 F. However, when they are further reacted With ethylene or propylene urea between 50%60% of the reaction product does not volatize. When methylol derivatives of methyl, ethyl, propyl, hydroxy ethyl, methoxy ethyl and butyl carbamate are further reacted with glyoxal and urea, the resulting product does not volatilize even when exposed to temperatures of 300 F. for 30 minutes.
The formulae are as follows:
(2) Treatment with ethylene urea to produce dimethylol ethylene urea:
(3) Treatment with propylene urea to produce dimethylol propylene urea:
(4) Treatment with glyoxal and urea to produce dihydroxy dirnethylol ethylene urea:
In the initial reaction when formaldehyde is reacted with the carbamate, it was found that the amount of formaldehyde may vary from 2 to 2.5 moles, the preferred amount being 2.25 moles. The pH must be adjusted to about 10 by the use of an alkali, for example, sodium hydroxide, potassium hydroxide, sodium carbonate, etc.
Reaction is continued for about 1' /2 hours at 10 pH. It was found to be of importance that the pH should not drop below 9.5. The degree of methylolation is usually between and The reaction temperature is about F. to F.
The resulting product is cooled to 120 F. and pH is adjusted to 4.0 by the use of maleic acid, citric acid, tartaric acid or hydrochloric acid. Maleic acid is preferred. The product is held at a pH of 4.0 at 120 F. for about one hour.
As far as the subsequent reactions are concerned, if the excess formaldehyde is to be reacted with ethylene urea or propylene urea, pH is adjusted back to 9.5 with sodium hydroxide. Reaction is continued for 2 hours, the product is cooled and is again neutralized to 6.5 pH with a suitable acid, such as maleic acid.
Practical experimentation has shown that in the case of dimethylol methoxy ethyl carbamate the use of propylene urea lowered the free formaldehyde from a range of 6% to between 1.5 %2% of free formaldehyde.
If reaction takes place with glyoxal and urea, the pH is adjusted to from 4 to about 5 with caustic soda solution; the product is heated for 3 to 3%. hours and then cooled. No further adjustment is necessary. At this stage the free residual formaldehyde amounts to less than 1% and the product does not volatilize even at high temperatures. Experimentation with various amounts of glyoxal and urea has indicated that the amount of free formaldehyde decreases if a somewhat larger amount of urea in relation to glyoxal is used, namely for 1 mole glyoxal the urea should preferably be in the range of about 1.3 to 1.4 moles.
The following examples have been given by way of exemplification only:
EXAMPLE 1 75 gr. methyl carbamate (1 mole) are reacted with 183 gr. (2.25 moles) of 37% formaldehyde. 0.45 gr. sodium hydroxide are added to adjust the pH to 10.3. The reaction is continued for 1% hours at 158 P. Then the product is cooled to 113 F. About 1 gr. maleic acid is added to adjust the pH to 4.0. At this stage 1.71 moles of formaldehyde have been reacted, leaving 0.54 mole free formaldehyde.
Then 40.7 gr. (0.27 mole) 40% glyoxal and 16.2 gr. (0.27 mole) urea are added. The amount of urea may be increased to 0.35 mole. The reaction is continued for 2 hours at 176 F.
The resulting product is practically water white. It contains from 0.5% to 1.0% free formaldehyde and it will not volatilize at 300 F. for minutes. It is most effective as a finish for cotton fabrics and cotton polyester blend fabrics.
EXAMPLE 2 103. gr. (1 mole) propyl carbamate are reacted with 183 gr. (2.25 moles) of 37% formaldehyde. 0.45 gr. sodium hydroxide are added to adjust the pH to 10.3. The reaction is continued for 2 hours at 158 F. Then the product is cooled to 113 F. 1 gr. maleic acid is added to change the pH to 4.0. At this stage 1.75 moles of formaldehyde have been reacted, leaving 0.5 mole of formaldehyde free.
Sodium hydroxide is added to set pH at 5.0. 40.7 gr. (0.27 mole) of 40% glyoxal are added along with an amount of urea which may vary from 16.2 gr. (0.27 mole) to 21 gr. (0.35 mole). The reaction is continued for about 2 hours at about 175 F. The resulting product contains 0.5% to 1.0% free formaldehyde, it will not volatilize readily and it produces an excellent finish.
EXAMPLE 3 89 gr. (1 mole) ethyl carbamate are reacted with 183 gr. (2.25 moles) of 37% formaldehyde. 0.45 gr. sodium hydroxide are added. The reaction is continued for 1% hours at 158 F. Then the product is cooled to 113 F. and citric acid is added to set the pH at 4.0. At this stage 1.8 moles of formaldehyde have been reacted, leaving 0.45 mole of free formaldehyde.
Sodium hydroxide is added to set pH at 5.5. 40.7 gr. (0.27 mole) of 40% glyoxal are added with 16.2 gr. (0.27 mole) urea. The reaction is continued for 2 hours 4 at 175 F. The resulting product contains 0.5% to 1.0% free formaldehyde; it will not volatilize readily and it produces an excellent finish.
EXAMPLE 4 119 gr. (1 mole) methoxy ethyl carbamate are reacted with 183 gr. (2.25 moles) of 37% formaldehyde. 1 gr. potassium hydroxide is added to adjust the pH to 10.2. The reaction is continued for 1% hours at F. Then the product is cooled to 113 F. Citric acid is added to set the pH at 4.0. At this stage 1.7 moles of formaldehyde have been reacted, leaving 0.55 mole of free formaldehyde.
Sodium hydroxide is added to set pH at 5.5. 47 gr. (0.27 mole) of 40% glyoxal are added along with 21.6 gr. (0.36 mole) urea. The reaction is continued for about 2 hours at about F. The resulting product contains 0.5% to 1.0% free formaldehyde; it will not volatilize readily and it produces an excellent finish.
EXAMPLE 5 105 gr. (1 mole) hydroxy ethyl carbamate are reacted with 203 gr. (2.5 moles) of 37% formaldehyde. 1.8 gr. sodium hydroxide are added to adjust the pH to 10.5. The reaction is continued for 1% hours at 158 F. Then the product is cooled to 113 F. Citric acid is added to adjust the pH to 4.0. At this stage approximately 1.8 moles of formaldehyde have been reacted, leaving 0.7 mole of free formaldehyde.
Sodium hydroxide is added to set pH at 5.0. 52.2 gr. (0.35 mole) of 40% glyoxal and 21 gr. (0.35 mole) urea are added. The reaction is continued for 2 hours at 176 F. The resulting product contains 0.5% to 1% free formaldehyde; it will not volatilize readily and it produces an excellent finish.
TREATMENT OF FABRIC All of the above described products are used in essentially the same manner, namely, a bath is prepared containing 10% to 35%, preferably 15% to 25% of the prod net in water and from 1% to 2% of a catalyst which is a metallic salt of a strong acid, such as magnesium chloride, zinc chloride or zinc nitrate. The fabric is conventionally treated in the bath by pad application. Then the fabric is dried at 200 F .-240 F. for 4 to 8 minutes and is cured at 300 F. to 350 F. for 1 to 3 minutes. As already stated, cotton and cotton polyester blend fabrics are particularly suitable for these treatments.
Fabrics which are those finished have excellent crush resistance and dimensional control as well as all other advantageous properties which are at least as good as those imparted to fabrics by prior art carbamate finishes. Furthermore, they have the additional advantages as compared to prior art carbamate finishes, that the amount of free formaldehyde is reduced to a negligible quantity and that the finish is non-volatile. Accordingly, the carbamate finishes of this invention can be used satisfactorily in permanent press processing.
It is apparent that the examples described above have been given solely by way of illustration and not by way of limitation and that they are capable of many variations and modifications within the scope of the present invention. All such variations and modifications are to be included within the scope of the present invention.
What is claimed is:
1. A finish for textile fabrics comprising a material resulting from a first reaction of one molar part of a carbamate compound selected from the group consisting of methyl carbamate, ethyl carbamate, propyl carbamate, methoxy-ethyl carbamate, hydroxy-ethyl carbamate and butyl carbamate with more than two molar parts of formaldehyde under reaction conditions of elevated temperature and alkaline pH and carrying forward said reaction as far as it will go and thence reacting all of the excess formaldehyde from said first reaction and in the presence of said product of said first reaction in a second reaction with a sufiicient amount of a compound selected from the group consisting of ethylene urea, propylene urea and combined glyoxal and urea at elevated temperatures and at a pH of from 5 to 9 and carrying forward said second reaction as far as it will go.
2. A finish for textile fabrics as described in claim 1 the reactant used to react with said excess formaldehyde from said first reaction being combined glyoxal and urea in proportion of one molar part of glyoxal to at least 1.3 molar parts of urea.
3. A textile fabric having the finish of claim 1.
References Cited UNITED STATES PATENTS 2,937,966 5/1960 Updegraif et al. 26029.4 3,052,570 9/1962 Polansky et al 260849 3,211,805 10/1965 Herbes et a1. 260849 3,219,632 11/1965 Frick et a1. 260-29.4
JOAN C. BLEUTGE, Primary Examiner US. Cl. X.R.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US61126867A | 1967-01-24 | 1967-01-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3590100A true US3590100A (en) | 1971-06-29 |
Family
ID=24448345
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US3590100D Expired - Lifetime US3590100A (en) | 1967-01-24 | 1967-01-24 | Methods of producing and applying textile finishes and finishes produced by such methods |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US3590100A (en) |
| BE (1) | BE697759A (en) |
| NL (1) | NL6708395A (en) |
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4039496A (en) * | 1974-09-09 | 1977-08-02 | American Cyanamid Company | Low formaldehyde fully etherified methylolated melamine with urea-formaldehyde-glyoxal as textile resin |
| US4072466A (en) * | 1974-09-09 | 1978-02-07 | American Cyanamid Company | Cellulosic textile treated with low formaldehyde fully etherified methylolated melamine with urea-formaldehyde-glyoxal |
| US4284758A (en) * | 1979-11-08 | 1981-08-18 | Sun Chemical Corp. | Glyoxal/cyclic urea condensates |
| US4285690A (en) * | 1979-11-08 | 1981-08-25 | Sun Chemical Corporation | Novel reactants for crosslinking textile fabrics |
| US4300898A (en) * | 1979-11-08 | 1981-11-17 | Sun Chemical Corporation | Compositions for treating textile fabrics |
| US4331438A (en) * | 1980-11-10 | 1982-05-25 | Basf Wyandotte Corporation | Process for eliminating free formaldehyde in textile materials treated with dimethylolated carbamates |
| US4345063A (en) * | 1979-11-08 | 1982-08-17 | Sun Chemical Corporation | Glyoxal/cyclic urea condensates |
| EP0043036B1 (en) * | 1980-07-02 | 1983-06-29 | Vianova Kunstharz Aktiengesellschaft | Process for reducing the formaldehyde emission in acid-curable paints based on a mixture of a urea resin and an alkyde resin |
| US4847143A (en) * | 1985-06-04 | 1989-07-11 | Sumitomo Chemical Company, Limited | Binder composition and nonwoven fabrics and impregnated papers using the same |
| US5143954A (en) * | 1990-11-27 | 1992-09-01 | Rohm And Haas Company | Low-formaldehyde, self-crosslinking polymer latex composition |
| US5951715A (en) * | 1998-09-24 | 1999-09-14 | National Starch And Chemical Investment Holding Corporation | Polysaccharide aldehydes and acetals as permanent press agents for textiles |
| US6380353B1 (en) | 1998-04-02 | 2002-04-30 | Basf Aktiengesellschaft | Method for reducing the C1-C2-aldehyde content formed from compounds with -CH2-CHR-O-or-CH(OH)-groups |
| EP3085724A1 (en) | 2015-04-24 | 2016-10-26 | Cavenaghi SPA | Foundry binder system with a low formaldehyde content and process for obtaining it |
| US10745556B1 (en) * | 2020-01-17 | 2020-08-18 | Chang Chun Plastics Co., Ltd. | Amino resin composition and varnish, coating layer, and product comprising the same |
-
1967
- 1967-01-24 US US3590100D patent/US3590100A/en not_active Expired - Lifetime
- 1967-04-28 BE BE697759D patent/BE697759A/xx unknown
- 1967-06-16 NL NL6708395A patent/NL6708395A/xx unknown
Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4039496A (en) * | 1974-09-09 | 1977-08-02 | American Cyanamid Company | Low formaldehyde fully etherified methylolated melamine with urea-formaldehyde-glyoxal as textile resin |
| US4072466A (en) * | 1974-09-09 | 1978-02-07 | American Cyanamid Company | Cellulosic textile treated with low formaldehyde fully etherified methylolated melamine with urea-formaldehyde-glyoxal |
| US4284758A (en) * | 1979-11-08 | 1981-08-18 | Sun Chemical Corp. | Glyoxal/cyclic urea condensates |
| US4285690A (en) * | 1979-11-08 | 1981-08-25 | Sun Chemical Corporation | Novel reactants for crosslinking textile fabrics |
| US4300898A (en) * | 1979-11-08 | 1981-11-17 | Sun Chemical Corporation | Compositions for treating textile fabrics |
| US4345063A (en) * | 1979-11-08 | 1982-08-17 | Sun Chemical Corporation | Glyoxal/cyclic urea condensates |
| EP0043036B1 (en) * | 1980-07-02 | 1983-06-29 | Vianova Kunstharz Aktiengesellschaft | Process for reducing the formaldehyde emission in acid-curable paints based on a mixture of a urea resin and an alkyde resin |
| US4331438A (en) * | 1980-11-10 | 1982-05-25 | Basf Wyandotte Corporation | Process for eliminating free formaldehyde in textile materials treated with dimethylolated carbamates |
| US4847143A (en) * | 1985-06-04 | 1989-07-11 | Sumitomo Chemical Company, Limited | Binder composition and nonwoven fabrics and impregnated papers using the same |
| US5143954A (en) * | 1990-11-27 | 1992-09-01 | Rohm And Haas Company | Low-formaldehyde, self-crosslinking polymer latex composition |
| US6380353B1 (en) | 1998-04-02 | 2002-04-30 | Basf Aktiengesellschaft | Method for reducing the C1-C2-aldehyde content formed from compounds with -CH2-CHR-O-or-CH(OH)-groups |
| US5951715A (en) * | 1998-09-24 | 1999-09-14 | National Starch And Chemical Investment Holding Corporation | Polysaccharide aldehydes and acetals as permanent press agents for textiles |
| EP3085724A1 (en) | 2015-04-24 | 2016-10-26 | Cavenaghi SPA | Foundry binder system with a low formaldehyde content and process for obtaining it |
| EP3530685A1 (en) | 2015-04-24 | 2019-08-28 | Cavenaghi SPA | Foundry binder system with a low formaldehyde content and process for obtaining it |
| US10745556B1 (en) * | 2020-01-17 | 2020-08-18 | Chang Chun Plastics Co., Ltd. | Amino resin composition and varnish, coating layer, and product comprising the same |
| CN111732700A (en) * | 2020-01-17 | 2020-10-02 | 长春人造树脂厂股份有限公司 | Amino resin composition, and varnish, coating and product containing amino resin composition |
Also Published As
| Publication number | Publication date |
|---|---|
| BE697759A (en) | 1967-10-30 |
| NL6708395A (en) | 1968-07-25 |
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| Date | Code | Title | Description |
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| AS | Assignment |
Owner name: SANDOZ, INC., 59 ROUTE 10, EAST HANOVER, NJ 07936 Free format text: ASSIGNMENT OF ASSIGNORS INTEREST. EFFECTIVE DATE;ASSIGNOR:ARKANSAS COMPANY, INC.;REEL/FRAME:004209/0628 Effective date: 19840104 |