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US3024080A - 2, 6-dioxaspiro (3, 3)heptane treated cellulose fabric and the production thereof - Google Patents

2, 6-dioxaspiro (3, 3)heptane treated cellulose fabric and the production thereof Download PDF

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Publication number
US3024080A
US3024080A US689788A US68978857A US3024080A US 3024080 A US3024080 A US 3024080A US 689788 A US689788 A US 689788A US 68978857 A US68978857 A US 68978857A US 3024080 A US3024080 A US 3024080A
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fabric
dioxaspiroheptane
dioxaspiro
treated
crease
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US689788A
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Benneville Peter L De
Richard O Steele
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Rohm and Haas Co
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Rohm and Haas Co
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Priority to US689788A priority Critical patent/US3024080A/en
Priority to DER24122A priority patent/DE1080514B/en
Priority to GB31397/58A priority patent/GB889402A/en
Priority to FR776657A priority patent/FR1222474A/en
Priority to CH6501458D priority patent/CH6501458A4/en
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Publication of US3024080A publication Critical patent/US3024080A/en
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    • 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
    • D06M13/10—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 oxygen
    • D06M13/165—Ethers
    • 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
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/08—Oxirane

Definitions

  • this compound will be hereinafter referred to by the shorter term dioxaspiroheptane.
  • the extent of modification by means of this compound may be controlled by variation in the proportion of the dioxaspiroheptane and by variation in the amount of catalyst. employed during the treatment therewith.
  • the treatment with dioxaspiroheptane may be effected most advantageously by means of aqueous solutions thereof in which the dioxaspiroheptane is dissolved at a concentration which may vary from 1 to 30% by weight.
  • concentration is from 5 to 15% to obtain the maximum benefits in crease-proofing and the like.
  • the treatment with dioxaspiroheptane may be carried out in the presence of a catalyst.
  • a catalyst is metal salts of acids having the composition H,(XYb), Where H is hydrogen, a is an integer which depends on the valence of the complex ion and may have a value of 1 to'3, X is a non-metal selected from the group consisting of boron, silicon, sulfur, and chlorine, said non-metal being in a state where its valence is from 3 to 7, Y is fluorine or oxygen, and b is an integer having a value of 4 or 6.
  • the metals of these salts are those of groups lb, II, 1111), IV, and VIII of the periodic table in T.
  • Salts of perchloric and fluoboric acids are very efiicient catalysts, particularly their zinc, lead, copper, and magnesium compounds.
  • Salts of sulfuric acid, such as aluminum and copper sulfate, and of fiuosilicic acid, such as magnesium, zinc, and copper fluosilicates also are active as catalysts.
  • Other acidic compounds, oxalic acid, for example, may also be used as catalysts.
  • the amount of catalyst may vary from about 0.2 to 2% and is preferably in the range of 0.5 to 1% concentration in the aqueous solution of dioxaspiroheptane.
  • the catalyzed solution of dioxaspiroheptane is compatible with solutions or dispersions of most of the common textile finishing agents, such as synthetic polymer latices and aminoplast resins or precondensates, so that they may be applied with the dioxaspiroheptane to produce changes in the hand or other properties of the fabric.
  • common textile finishing agents such as synthetic polymer latices and aminoplast resins or precondensates
  • the aqueous solution containing dioxaspiroheptane and aszaass Patented Mar. 6, 1962 catalyst may be applied to the fabric in any suitable manner such as by spraying or impregnation.
  • the impregnation may be carried out in open width, and the fabric may be handled in any form.
  • the impregnation may be carried out in a tumble wheel, laundry machne, or other suitable equipment.
  • the fabric treated with solution may be dried, such as by air-drying at normal room temperature or by heating in a drying oven at temperatures of F. and up.
  • the drying and curing operations are preferably done with the fabric open and flat, so that it will have a smooth and even appearance when finished.
  • the impregnated fabric, immediately after impregnation and without preliminary low-temperature drying is carried in open width by a tenter frame through a curing oven where it is subjected to temperatures of about 250 F. to about 400 F.
  • the treated fabrics exhibit a high degree of crush resistance and crease recovery with little or no change in the hand or feel of the fabric.
  • the treatment does not discolor the fabric.
  • the treated fabrics have the important advantage that they do not retain chlorine, so that the use of bleaching agents containing chlorine does not cause deterioration either by way of discoloration or loss in tensile strength even when the treated fabrics which have been bleanched are subjected to ironing temperatures.
  • the treated fabrics are also resistant to shrinkage during laundering, and the treatment is very permanent towards laundering, dry-cleaning, and other procedures for cleaning textile fabrics.
  • EXAMPLE 1 A sample of cotton printcloth was saturated with an aqueous solution containing 20% dioxaspiroheptane and 1% zinc perchlorate. It was then put into an oven at C. and baked for 15 minutes. Controls treated with water and 1% zinc perchlorate were similarly prepared.
  • the dioxaspiroheptane-treated fabric was insoluble in cuprammonium hydroxide while the controls dissolved readily.
  • Samples of the treated fabric taken before and after washing were chlorinated in 50 times their weight of a bleach bath containing 0.25% of available chlorine for 15 minutes at room temperature. After being dried, and conditioned, the samples were pressed under an iron at 365 C. for 0.5 minute. Neither sample showed any discoloration or loss of tensile strength after this procedure.
  • EXAMPLE 8 A sample of cotton printcloth was treated with a solution containing 10% of dioxaspiroheptane, 1% of zinc perchlorate, and 4% of a partially condensed urea-formaldehyde resin. The treated fabric was cured for 15 minutes at C. After being conditioned, it had a stiffer, firmer, more resilient hand, and a crease recovery of 137.
  • EXAMPLE 9 A sample of cotton printcloth was treated with a solution containing a mixture of 5% dioxaspiroheptane and 5% dimethylol-N,N-ethyleneurea with 1% zinc fluoborate as a catalyst. The application was made on a textile pad and the impregnated fabric was baked for 1 0 minutes at 150 C. After the fabric was conditioned, its crease recovery angle was 139.
  • the process comprising impregnating a cellulose fabric With an aqueous solution of 2,6-dioxaspiro(3,3)- heptane and a catalyst, and heating the impregnated fabric at a temperature of about 250 to 400 F., until the crease resistance of the fabric is increased.
  • the process comprising impregnating a cellulose fabric With an aqueous solution containing 1 to 30% by weight of 2,6-dioxaspiro(3,3)heptans and 0.2 to 2% of a catalyst and heating the impregnated fabric at a temperature of about 250 to 400 F. until the crease-resistance of the fabric is increased.
  • the process comprising impregnating a cellulose fabric with an aqueous solution containing 1 to 30% by weight of 2,6-dioxaspiro(3,3)heptane and 0.2 to 2% of magnesium fiuoborate, and heating the impregnated fabric 6 at a temperature of about 250 to 400 F. until the crease-resistance of the fabric is increased.
  • the process comprising impregnating a cellulose fabric with an aqueous solution containing 1 to 30% by Weight of 2,6-dioxaspiro(3,3)heptane and 0.2 to 2% of zinc perchlorate and heating the impregnated fabric at a temperature of about 250 to 400 F. until the creaseresistance of the fabric is increased.
  • the process comprising impregnating a cellulose fabric with an aqueous solution containing 1 to 30% by weight of 2,6-dioxaspiro(3,3)heptane and 0.2 to 2% of zinc fiuoborate and heating the impregnated fabric at a temperature of about 250 to 400 F. until the creaseresistance of the fabric is increased.
  • a cellulose fabric having improved crease resistance obtained by the process of claim 1.
  • a cotton fabric having improved crease resistance obtained by the process of claim 5.
  • a regenerated cellulose fabric having improved crease resistance obtained by the process of claim 6.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Chemical Or Physical Treatment Of Fibers (AREA)

Description

3,624 080 2,6 -DIUXASPIRQ(3,3)HEPTANE TREATED CEL- LULOiiE FABRIC AND THE PRODUCTKQN THEREGF Peter L. De Benneville, Philadelphia, Pa, and Richard 0. Steele, Moerestown, N.J., assignors to Rohm & Haas Company, Philadelphia, Pa, a corporation of Delaware No Drawing. Filed Oct. 14, 1957, Ser. No. 689,788 20 Claims. (Cl. 8-120) reduced shrinkage on Washing so that partial or complete dimensional stabilization may be eifected. The invention also embraces the treated fabrics obtained.
In accordance with the present invention, it has been found that cellulosic fabrics, woven, knitted, or other-,
wise formed, have reduced shrinkage on washing and acquire resistance to creasing and crushing when they are treated with 2,6-dioxaspiro(3,3)heptane of the formula C C H2 H:
For convenience, this compound will be hereinafter referred to by the shorter term dioxaspiroheptane. The extent of modification by means of this compound may be controlled by variation in the proportion of the dioxaspiroheptane and by variation in the amount of catalyst. employed during the treatment therewith.
The treatment with dioxaspiroheptane may be effected most advantageously by means of aqueous solutions thereof in which the dioxaspiroheptane is dissolved at a concentration which may vary from 1 to 30% by weight. Preferably, the concentration is from 5 to 15% to obtain the maximum benefits in crease-proofing and the like.
The treatment with dioxaspiroheptane may be carried out in the presence of a catalyst. We have found that the most effective catalysts are metal salts of acids having the composition H,(XYb), Where H is hydrogen, a is an integer which depends on the valence of the complex ion and may have a value of 1 to'3, X is a non-metal selected from the group consisting of boron, silicon, sulfur, and chlorine, said non-metal being in a state where its valence is from 3 to 7, Y is fluorine or oxygen, and b is an integer having a value of 4 or 6. The metals of these salts are those of groups lb, II, 1111), IV, and VIII of the periodic table in T. Moeller, Inorganic Chemistry, John Wiley 8: Sons, New York, 1952, which have an atomic weight of at least 12. Salts of perchloric and fluoboric acids are very efiicient catalysts, particularly their zinc, lead, copper, and magnesium compounds. Salts of sulfuric acid, such as aluminum and copper sulfate, and of fiuosilicic acid, such as magnesium, zinc, and copper fluosilicates, also are active as catalysts. Other acidic compounds, oxalic acid, for example, may also be used as catalysts.
Conveniently, the amount of catalyst may vary from about 0.2 to 2% and is preferably in the range of 0.5 to 1% concentration in the aqueous solution of dioxaspiroheptane.
The catalyzed solution of dioxaspiroheptane is compatible with solutions or dispersions of most of the common textile finishing agents, such as synthetic polymer latices and aminoplast resins or precondensates, so that they may be applied with the dioxaspiroheptane to produce changes in the hand or other properties of the fabric.
The aqueous solution containing dioxaspiroheptane and aszaass Patented Mar. 6, 1962 catalyst may be applied to the fabric in any suitable manner such as by spraying or impregnation. In general, it is preferable to use some method of impregnation. With .piece goods, this is conveniently carried out with the various machines used for treating fabric in open width, such as pads or jigs. However, it is not required that the impregnation be carried out in open width, and the fabric may be handled in any form. In treating garments or other articles made from cellulosic fabrics, the impregnation may be carried out in a tumble wheel, laundry machne, or other suitable equipment. After application of the solution, it is desirable to remove the excess solution by squeezing the fabric between rollers, or by shaking or centrifuging it, in order to insure a more even treatment. The fabric treated with solution may be dried, such as by air-drying at normal room temperature or by heating in a drying oven at temperatures of F. and up. The drying and curing operations are preferably done with the fabric open and flat, so that it will have a smooth and even appearance when finished. In a preferred embodiment, the impregnated fabric, immediately after impregnation and without preliminary low-temperature drying is carried in open width by a tenter frame through a curing oven where it is subjected to temperatures of about 250 F. to about 400 F. or higher for a period of time ranging from about one minute to about one-half hour or more, the shorter period being employed at the higher temperature and vice versa. Entirely satisfactory results are obtained by heating for ten minutes at about 300 F. This curing operation not only dries the impregnated fabric but apparently causes a reaction between the dioxaspiroheptane and the hydroxyl groups of the cellulose. Presumably, the hydroxyl group of a cellulose molecule causes an opening of the oxide ring and addition to form some such linkage as may be represented by the following formula:
noon: CHZOH where Cel represents a cellulose molecule. The two oxide rings in the dioxaspiroheptane may react with hydroxyl groups on the same cellulose molecule, or on different molecules. It is not intended, however, that the present invention be limited to this theory of operation.
The treated fabrics exhibit a high degree of crush resistance and crease recovery with little or no change in the hand or feel of the fabric. The treatment does not discolor the fabric. In addition, the treated fabrics have the important advantage that they do not retain chlorine, so that the use of bleaching agents containing chlorine does not cause deterioration either by way of discoloration or loss in tensile strength even when the treated fabrics which have been bleanched are subjected to ironing temperatures. The treated fabrics are also resistant to shrinkage during laundering, and the treatment is very permanent towards laundering, dry-cleaning, and other procedures for cleaning textile fabrics.
' The following examples illustrate the present invention, and the parts and percentages therein are byweight unless otherwise noted. The crease recovery values given below were determined by the Shirley Institute procedure (British Standards Handbook No. 11, 1949 ed., page 128).
EXAMPLE 1 A sample of cotton printcloth was saturated with an aqueous solution containing 20% dioxaspiroheptane and 1% zinc perchlorate. It was then put into an oven at C. and baked for 15 minutes. Controls treated with water and 1% zinc perchlorate were similarly prepared.
After being conditioned the samples had the following crease recovery values:
The dioxaspiroheptane-treated fabric was insoluble in cuprammonium hydroxide while the controls dissolved readily.
The durability of the treatment was shown by the following tests. Samples of the dioxaspiroheptane-treated fabric were extracted (1) in boiling water for one hour, (2) in 0.1 N HCl at 80 C. for one hour, and (3) in 0.1 NaOH for 24 hours at 20 C. The extracted samples were still insoluble in cuprammonium hydroxide, and had good crease recovery,v as shown by the following data:
Degrees Water extraction 132 HCl extraction- 125 NaOH extraction 123 EXAMPLE 2 EXAMPLE 3 Samples of cotton printcloth were saturated with 20% aqueous solutions of dioxaspiroheptane containing various amounts of zinc perchlorate catalyst. They were then cured in an oven at 150 C. for 15 minutes. After being conditioned, the samples were tested for crease recovery. The following results were obtained:
Table A Concentration Crease of Zn(OlOi)a recovery (percent) (degrees) EXAMPLE 4 Samples of cotton printcloth were treated with aqueous solutions of dioxaspiroheptane at various concentrations, each solution containing either 0.5% or 1.0% of Zinc perchlorate as catalyst and then baked at 150 C. for 15 minutes. Water and catalyst controls were also prepared. The samples were conditioned and tested for crease recovery with the following results:
Table B Crease recovery (degrees) Concentration of dioxaspiroheptane (percent) 0.5% catalyst 1.0% catalyst EXAMPLE 5 Various types of cotton fabrics were treated by saturation in an aqueous solution containing dioxaspiroheptame and 0.75% of zinc perchlorate. After heating in an oven for 15 minutes at 150 C., the results summarized in the following table were obtained:
Table C Grease recovery angles Fabric Count Water Treated Printcloth x 80 80 125 Broadeloth 120 x 60 123 Muslin 54 x 46 78 99 Lawn 107 X 97 08 128 EXAMPLE 6 A sample of cotton printcloth was impregnated with a solution containing 20% dioxaspiroheptane and 0.75% zinc perchlorate under conditions such that the wet pickup of the fabric was about of its dry weight. The sample was held on a pin-frame at its orginal dimensions and baked for 15 minutes in an oven at 150 C. A watertreated control was also prepared. The two samples were then washed by the procedure given in Method 5550 of the Federal Specification CCC-T-191b. The area shrinkage of the control was 19.7% while that of the treated sample was only 4.6%.
Samples of the treated fabric taken before and after washing were chlorinated in 50 times their weight of a bleach bath containing 0.25% of available chlorine for 15 minutes at room temperature. After being dried, and conditioned, the samples were pressed under an iron at 365 C. for 0.5 minute. Neither sample showed any discoloration or loss of tensile strength after this procedure.
EXAMPLE 7 Table D Crease recovery (degrees) Time of baking (minutes) 275 F. 300 F. 325 F.
EXAMPLE 8 A sample of cotton printcloth was treated with a solution containing 10% of dioxaspiroheptane, 1% of zinc perchlorate, and 4% of a partially condensed urea-formaldehyde resin. The treated fabric was cured for 15 minutes at C. After being conditioned, it had a stiffer, firmer, more resilient hand, and a crease recovery of 137.
EXAMPLE 9 A sample of cotton printcloth was treated with a solution containing a mixture of 5% dioxaspiroheptane and 5% dimethylol-N,N-ethyleneurea with 1% zinc fluoborate as a catalyst. The application was made on a textile pad and the impregnated fabric was baked for 1 0 minutes at 150 C. After the fabric was conditioned, its crease recovery angle was 139.
We claim:
1. The process comprising impregnating a cellulose fabric With an aqueous solution of 2,6-dioxaspiro(3,3)- heptane and a catalyst, and heating the impregnated fabric at a temperature of about 250 to 400 F., until the crease resistance of the fabric is increased.
2. A process as defined in claim 1 in which the fabric is cotton.
3. A process as defined in claim 1 in which the fabric is regenerated cellulose rayon.
4. The process comprising impregnating a cellulose fabric With an aqueous solution containing 1 to 30% by weight of 2,6-dioxaspiro(3,3)heptans and 0.2 to 2% of a catalyst and heating the impregnated fabric at a temperature of about 250 to 400 F. until the crease-resistance of the fabric is increased.
5. A process as defined in claim 4 in which the fabric is cotton.
6. A process as defined in claim 4 in which the fabric is regenerated cellulose rayon.
7. The process comprising impregnating a cellulose fabric with an aqueous solution containing 1 to 30% by weight of 2,6-dioxaspiro(3,3)heptane and, as a catalyst, 0.2 to 2% of a member selected from the group consisting of aluminum and copper sulfates, oxalic acid, and metal salts of an acid of the formula H (XY where H is hydrogen, a is an integer having a value of 1 to 3, X is a member selected from the group consisting of boron, silicon, sulfur, and chlorine, Y is a member selected from the group consisting of fluorine and oxygen, and b is an integer selected from 4 and 6, said metal having an atomic weight of at least 12 and being selected from the group consisting of those in groups 1b, II, IIIb, IV, and VIII of the periodic table, and heating the impregnated fabric at a temperature of about 250 to 400 F. until the crease-resistance of the fabric is increased.
8. A process according to claim 7 in which the fabric is cotton.
9. A process according to claim 7 in which the fabric is regenerated cellulose rayon.
10. The process comprising impregnating a cellulose fabric with an aqueous solution containing 1 to 30% by weight of 2,6-dioxaspiro(3,3)heptane and 0.2 to 2% of magnesium fiuoborate, and heating the impregnated fabric 6 at a temperature of about 250 to 400 F. until the crease-resistance of the fabric is increased.
11. A process as defined in claim 10 in which the fabric is cotton.
12. A process as defined in claim 10 in which the fabric is regenerated cellulose rayon.
13. The process comprising impregnating a cellulose fabric with an aqueous solution containing 1 to 30% by Weight of 2,6-dioxaspiro(3,3)heptane and 0.2 to 2% of zinc perchlorate and heating the impregnated fabric at a temperature of about 250 to 400 F. until the creaseresistance of the fabric is increased.
14. A process as defined in claim 13 in which the fabric is cotton.
15. A process as defined in claim 13 in which the fabric is regenerated cellulose rayon.
16. The process comprising impregnating a cellulose fabric with an aqueous solution containing 1 to 30% by weight of 2,6-dioxaspiro(3,3)heptane and 0.2 to 2% of zinc fiuoborate and heating the impregnated fabric at a temperature of about 250 to 400 F. until the creaseresistance of the fabric is increased.
17. A process as defined in claim 16 in which the fabric is cotton.
18. A cellulose fabric having improved crease resistance obtained by the process of claim 1.
19. A cotton fabric having improved crease resistance obtained by the process of claim 5.
20. A regenerated cellulose fabric having improved crease resistance obtained by the process of claim 6.
References Cited in the file of this patent UNITED STATES PATENTS 2,752,269 Condo June 26, 1956 2,764,575 Kohler Sept. 25, 1956 2,774,691 Schroeder Dec. 18, 1956 2,794,754 Schroeder June 4, 1957

Claims (1)

1. THE PROCESS COMPRISING IMPREGNATING A CELLULOSE FABRIC WITH AN AQUEOUS SOLUTION OF 2,6-DIOXASPIRO (3,3)HEPTANE AND A CATALYST, AND HEATING THE IMPREGNATED FABRIC AT A TEMPERATURE OF ABOUT 250* TO 400*F., UNTIL THE CREASE RESISTANCE OF THE FABRIC IS INCREASED.
US689788A 1957-10-14 1957-10-14 2, 6-dioxaspiro (3, 3)heptane treated cellulose fabric and the production thereof Expired - Lifetime US3024080A (en)

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Application Number Priority Date Filing Date Title
US689788A US3024080A (en) 1957-10-14 1957-10-14 2, 6-dioxaspiro (3, 3)heptane treated cellulose fabric and the production thereof
DER24122A DE1080514B (en) 1957-10-14 1958-09-30 Process to increase the elasticity of cellulose-containing fabrics
GB31397/58A GB889402A (en) 1957-10-14 1958-10-01 Treatment of cellulosic fabrics and the fabrics thereby obtained
FR776657A FR1222474A (en) 1957-10-14 1958-10-14 Treatment for cellulosic tissue
CH6501458D CH6501458A4 (en) 1957-10-14 1959-10-01 Process for treating cellulosic fabrics to reduce their resistance to creasing

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3097050A (en) * 1959-12-28 1963-07-09 Rohm & Haas Process of creaseproofing cellulose fabrics with 2, 6-dioxaspiro (3, 3) heaptane and ormaldehyde and fabrics produced thereby
US3239303A (en) * 1959-02-13 1966-03-08 Rohm & Haas Process for the treatment of textiles and the textiles obtained

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2900198A1 (en) * 1979-01-04 1980-07-17 Bosch Gmbh Robert CENTRIFUGAL SPEED REGULATOR FOR INJECTION INTERNAL COMBUSTION ENGINES, IN PARTICULAR IDLE SPEED REGULATOR FOR VEHICLE DIESEL ENGINES

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2752269A (en) * 1951-12-01 1956-06-26 Shell Dev Treatment of textile materials
US2764575A (en) * 1951-10-08 1956-09-25 Henkel & Cie Gmbh Synthetic resins from oxacyclobutane compounds and dicarboxylic acids
US2774691A (en) * 1954-09-21 1956-12-18 Shell Dev Treatment of textile materials and product
US2794754A (en) * 1956-04-30 1957-06-04 Shell Dev Treatment of textile materials

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2764575A (en) * 1951-10-08 1956-09-25 Henkel & Cie Gmbh Synthetic resins from oxacyclobutane compounds and dicarboxylic acids
US2752269A (en) * 1951-12-01 1956-06-26 Shell Dev Treatment of textile materials
US2774691A (en) * 1954-09-21 1956-12-18 Shell Dev Treatment of textile materials and product
US2794754A (en) * 1956-04-30 1957-06-04 Shell Dev Treatment of textile materials

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3239303A (en) * 1959-02-13 1966-03-08 Rohm & Haas Process for the treatment of textiles and the textiles obtained
US3097050A (en) * 1959-12-28 1963-07-09 Rohm & Haas Process of creaseproofing cellulose fabrics with 2, 6-dioxaspiro (3, 3) heaptane and ormaldehyde and fabrics produced thereby

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DE1080514B (en) 1960-04-28
FR1222474A (en) 1960-06-10
CH6501458A4 (en) 1962-08-31

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